JP3153822B2 - Medications used to promote blood circulation - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel medicine used for promoting blood circulation, and more particularly, to a method for promoting blood circulation containing a compound having an aconitine-type chemical structure or a salt thereof as an active ingredient. It relates to a medicine to be used.

[0002]

2. Description of the Related Art The causes of poor blood circulation include blood congestion due to chronic heart failure, stiffening and narrowing of blood vessel lumen due to arteriosclerosis, formation of blood clots, and contraction of blood vessels due to intrinsic or extrinsic sympathetic nerve excitation. However, poor blood circulation may be of unknown cause. Poor blood circulation may cause peripheral organs to have reduced function, dysfunction, or necrosis, cold limbs, pain, necrosis, or reduced memory and thinking in the central nervous system. However, there is no drug provided for relieving and eliminating these symptoms.

[0003]

DISCLOSURE OF THE INVENTION The present inventor has found that a compound having an aconitine-type chemical structure has a strong blood flow increasing effect in the course of various studies on a drug for promoting blood circulation.
However, it is known that aconitine, hypoconitine, mesaconitine and jesaconitine, which are typical compounds of the aconitine type alkaloids, have extremely high toxicity. Therefore, as a result of searching for a compound having a low-toxicity aconitine-type chemical structure that has a blood circulation promoting action and can be used as a medicine, the compound represented by the general formula (I) has an excellent blood circulation promoting action. Low toxicity
It has been found that it can be used as a medicament.

The present invention has been made based on such findings. That is, the present invention provides a compound represented by the general formula (I):

Embedded image [Wherein, R ₁ and R ₂ are each (i) a hydrogen atom, or (ii) a saturated alkyl or an unsaturated alkyl having or not having a substituent, or (iii) a substituent. whether the with or without an aliphatic or aromatic acyl, or a (iv) substituted or without aralkyl, R ₃ is a hydrogen atom or a hydroxyl group or an aliphatic acyloxy or aromatic acyloxy R ₄ is a hydrogen atom or a hydroxyl group, R ₅ is a hydrogen atom or a hydroxyl group or a lower alkoxy or an aliphatic acyloxy, and R ₆ is a hydrogen atom or a hydroxyl group, or forms a carbonyl group together with the carbon atom at position 15. R ₇ is a hydrogen atom or methyl or aliphatic acyl or aromatic acyl. Wherein a) R ₁ is benzoyl or anisoyl;
₂ is ethyl, R ₃ and R ₆ are hydroxyl groups, R ₅
Is an acetyloxy group, and when R ₇ is methyl, R ₄ is a hydrogen atom. B) R ₁ is benzoyl, R ₂ and R ₇ are methyl, and R ₃ is a hydrogen atom or a hydroxyl group. And when R ₅ is an acetyloxy group and R ₆ is a hydroxyl group, R ₄ is a hydrogen atom.] The compound having an aconitine-type chemical structure represented by the formula: The present invention provides a medicine used for the above.

[0005] The compound represented by the above formula (I) can be isolated from aconite or one which has been detoxified by heat treatment of aconite, for example, from processed bushes subjected to pressure and heat treatment in an autoclave. . For example, a methanol extract of aconite or processed bush is acidified with hydrochloric acid or the like, and after washing with an appropriate solvent such as chloroform,
The aqueous layer made basic with ammonia or the like is extracted using an organic solvent such as chloroform, and the resulting extract is subjected to alumina column chromatography, silica gel column chromatography, or thin flake chromatography, etc. For example, it can be purified and isolated using a methanol / chloroform solvent. Further, aconitine represented by the following formula (II), mesaconitine represented by the following formula (III), hypaconitine represented by the following formula (IV), gesaconitine represented by the following formula (V), and the following formula (VI) ), 14-0-benzoylaconine represented by the following formula (VII), 14-0-benzoylhypaconin represented by the following formula (VIII), 14- represented by (IX)
Aconitine-type alkaloids described in the literature such as 0-anisoylaconine, neolin represented by the following formula (X), pyroaconitins represented by the following formula (XI) and 16-epipyroaconitine are used as starting materials. Carrying out a deoxygenation reaction at the 3-, 8-, 13- or 15-position, or at its nitrogen atom or at its 1, 3-, 8-, 14- or 15-position;
It can be produced by substituting the substituent bonded to the position with various other substituents, and further performing a reaction by combining them.

[0006]

Embedded image R ₁ , R ₂ , R ₃ in each of the formulas (II) to (X),
R ₄ , R ₅ , R ₆ , and R ₇ are as shown in the following table.

[0007]

Embedded image (R ₁ is CH ₃ or C ₂ H ₅ and R ₂ is OH or H
And R ₃ is Bz or An.

The above-described deoxygenation reaction can be carried out by using an ion reaction, a radical reaction, a reduction reaction, or the like, which is usually used in a chemical reaction, or a combination thereof.

The above-mentioned ionic reaction can be carried out by dissolving the corresponding compound in a solvent using a dehydrating agent such as sulfuric acid or thionyl chloride as a solvent, and heating and refluxing the solution. In the corresponding compound, in the presence of imidazole, sodium hydride and the like, carbon disulfide and methyl iodide are stirred or heated to reflux under appropriate temperature conditions, and reacted.
It can be carried out by adding a tributyltin hydride or the like to the corresponding compound in a solvent such as benzene and stirring the mixture at room temperature or under reflux with heating.

The radical reaction can be carried out, for example, by dissolving the corresponding compound using water and hexamethyltriamide phosphate as a solvent and irradiating a low-pressure mercury lamp at room temperature or under cooling. Also, for example, a hydroxyl group of a corresponding compound such as oxalyl chloride is used as an active substituent, and a radical generating reagent such as αα′-azoisobutyronitrile and a reducing agent such as tributyltin hydride are used in a solvent such as benzene. And add
It can be carried out by heating under reflux or stirring at room temperature.

In the reduction reaction, for example, a corresponding compound is dissolved in a solvent such as ethanol or acetic acid, and catalytic hydrogenation is carried out at room temperature or under heating using platinum oxide, palladium carbon or Raney nickel as a catalyst. Can be performed. In the above-described deoxygenation reaction, the hydroxyl group is converted into a ketone using an oxidizing agent, for example, sodium dichromate, etc., and is converted to thioketal or hydrazone using ethanedithiol or p-toluenesulfonylhydrazine. After that, the corresponding compound is reduced with an organic metal reducing agent, such as lithium aluminum hydride and its alkoxy derivative, at room temperature, or under heating or cooling, using ether or tetrahydrofuran as a solvent. It can be carried out.

To replace a substituent bonded to a nitrogen atom with another substituent, first, the corresponding compound is dissolved in a suitable solvent,
For example, in acetone, a suitable oxidizing agent, for example, potassium permanganate is reacted to give an N-dealkylated product, and the obtained N-dealkylated product is reacted with another alkylating agent, acylating agent, etc. This can be done by reacting a compound, an alkyl halide, an aralkyl halide or the like.

In order to acylate or alkylate the hydroxyl group, the corresponding compound is combined with an acid chloride, a halogen compound or the like which is usually used when esterifying or etherifying the hydroxyl group, in a suitable solvent such as pyridine. It can be performed by reacting.

In order to substitute an acyl group existing in the form of an ester bond with another acyl group or an alkyl group, the ester group is deesterified by a hydrolysis reaction, for example, alkali hydrolysis.
After the formation of the hydroxyl group, the acylation or alkylation of the hydroxyl group can be carried out, or the ester itself can be stirred using a fatty acid or alcohol as a solvent under an appropriate temperature condition.

Further, in order to obtain the compound represented by the above formula (I), the above respective reactions can be combined in various ways.

The production examples of the compound represented by the above formula (I) are described below. The physical property values and analytical data of the compounds obtained in each Example are listed after the description of the Examples. The pharmacological action, toxicity, etc. of the compounds are shown in Tables 1 to 3 below.

Example 1 72 mg of LiAlH ₄ and 0.23 mg of methanol
A THF solution containing 60 ml of pyrogesaconitine was added to a solution of LiAl (OCH ₃ ) ₃ H in tetrahydrofuran (THF) at −70 ° C., stirred at this temperature for about 1 hour, and further at room temperature for 1 hour. Stir. After completion of the reaction, wet-THF was added to the reaction solution at 0 ° C.
The precipitate is filtered. The filtrate is concentrated to dryness under reduced pressure to obtain 45.6 mg of 8-deoxyaconine. 45 mg of 8-deoxyaconin is dissolved in a mixed solution of 5 ml of pyridine and 1 ml of methylene chloride, and 15 μl of p-anisoyl chloride is added at −70 ° C. The temperature is increased from -70 ° C to -5 ° C over 2 hours while stirring the reaction. Thereafter, ice water was added to the reaction solution, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and chloroform was added in an amount of 30 ml.
Extract three times with l. The chloroform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: 5% methanol / ammonia-saturated chloroform) to separate and purify, and then 8-deoxy-14-0-anisoylaconine 37 was obtained.
mg.

Example 2 100 mg of gesaconitine was dissolved in 1.5 ml of thionyl chloride, and the mixture was refluxed for 3 hours. After cooling, thionyl chloride is distilled off under reduced pressure. Ice water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted three times with 30 ml of chloroform. The roloform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ammonia-saturated ether: n-hexane = 4: 1), separated and purified to obtain 72.3 mg of anhydrogesaconitine. Next, 70 mg of anhydrogesaconitine is dissolved in 10 ml of ethanol, 33 mg of platinum oxide is added, and the mixture is vigorously stirred under a hydrogen stream for 1.5 hours. After the completion of the reaction, the catalyst is filtered, and the filtrate is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ammonia-saturated ether: n-hexane =
4: 1), followed by separation and purification to obtain 37 mg of 3-deoxygesaconitine.

Example 3 50 mg of 3-deoxygesaconitine was dissolved in a mixture of 2 ml of dioxane and 2 ml of water, and the mixture was heated under reflux for 4 hours. After cooling, the solvent is distilled off under reduced pressure. The residue was subjected to thin-layer chromatography (eluent: 5% methanol / ammonia-saturated chloroform), separated and purified to obtain 3-deoxy-14-0-anisoylaconine (38 mg).

Example 4 100 mg of 3-deoxygesaconitine is heated at 180 ° C. for 30 minutes under reduced pressure (1-2 mmHg). The reaction product is subjected to silica gel column chromatography (eluent: 5% methanol / chloroform) to separate and purify, to obtain 60 mg of 3-deoxypyrrogessaconitine. The procedure of Example 1 was repeated, except that 60 mg of 3-deoxypyrrogesaconitine was used instead of pyrogenesaconitine in Example 1, and 32 mg of 3,8-dideoxy-14-0-anisoylaconine was obtained. .

Example 5 150 mg of gesaconitine was dissolved in 10 ml of pyridine, and 0.5 ml of trifluoromethanesulfonic anhydride was added at 0 ° C., followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into ice water to make the mixture alkaline, and then extracted three times with 50 ml of chloroform. The chloroform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ammonia-saturated ether:
n-hexane = 4: 1) to separate and purify
98 mg of 0-trifluoromethanesulfonyl-anhydrogesaconitine are obtained. Next, 13-0-trifluoromethanesulfonyl-anhydrogesaconitine 90
is dissolved in 100 ml of a mixture of hexamethylphosphoric triamide and water (95: 5) and irradiated with a low-pressure mercury lamp at 2537 ° C. for 1 hour at 0 ° C. in a nitrogen stream. After completion of the reaction, the reaction solution is diluted with 5 times the volume of water to make it alkaline with ammonia, and then extracted three times with 500 ml of ether. The ether layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ammonia-saturated ether: n-hexane = 4: 1), separated and purified to obtain 41 mg of 13-deoxyanhydrogesaconitine. Next, 13-
40 mg of deoxyanhydrogesaconitine is dissolved in 7 ml of ethanol, 15 mg of platinum oxide is added, and the mixture is vigorously stirred under a hydrogen stream for 1.5 hours. After the completion of the reaction, the catalyst is filtered, and the filtrate is concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent: ammonia-saturated ether: n-hexane = 4: 1).
23 mg of 3,13-dideoxygesaconitine are obtained.

Example 6 The procedure of Example 3 was repeated except that 30 mg of 3,13-dideoxygesaconitine was used in place of 3-deoxygesaconitine. 22 mg of -14-0-anisoylaconine are obtained.

Example 7 The procedure of Example 4 was repeated except that 100 mg of 3,13-dideoxygesaconitine was used in place of 3-deoxygesaconitine. Pilosesaconitine 62
mg. Next, 3,13-dideoxypyrogesaconitine 6
Using the same procedure as in Example 1 except for using 0 mg,
48 mg of 3,8,13-trideoxyaconine are obtained.
Next, instead of 8-deoxyaconine of Example 1,
The same operation as in Example 1 was carried out except that 45 mg of 3,8,13-trideoxyaconine was used.
-Trideoxy 14-0-anisoylaconine 31 mg
Get

Example 8 The procedure of Example 1 was repeated, except that 20 μl of benzoyl chloride was used instead of p-anisoyl chloride of Example 1, except that 8-deoxy-14-0-
32 mg of benzoyl aconine are obtained.

Example 9 Aconitine was used in place of jessaconitine in Example 2, and 100 mg of aconitine was used.
The same operation as described above was performed, and 3-deoxyaconitine 35 mg
Get.

Example 10 Instead of 3-deoxygesaconitine in Example 3, 3-deoxyaconitine 50 was used.
The same operation as in Example 3 was carried out except for using mg to obtain 40.2 mg of 3-deoxy-14-0-benzoylaconine.

Example 11 The same operation as in Example 4 was carried out except that 100 mg of 3-deoxyaconitine was used instead of 3-deoxygesaconitine in Example 4, to obtain 68 mg of 3-deoxypyroaconitine. . Next, instead of the pyrogenesaconitine of Example 1, 3
-Using the same procedure as in Example 1 except for using 60 mg of deoxypyroaconitine, 49.5 mg of 3,8-dideoxyaconine was obtained. Next, instead of 8-deoxyaconine of Example 1, 3,8-dideoxyaconine 45
The same operation as in Example 1 was carried out except for using 20 mg of benzoyl chloride in place of p-anisoyl chloride to obtain 35 mg of 3,8-dideoxy-14-0-benzoylaconine.

Example 12 The same operation as in Example 5 was carried out except that 150 mg of aconitine was used in place of jessaconitine in Example 5, to obtain 25 mg of 3,13-dideoxyaconitine.

Example 13 The procedure of Example 3 was repeated, except that 30 mg of 3,13-dideoxyaconitine was used in place of 3-deoxygesaconitine in Example 3, except that 3,13-dideoxy-conitine was used. 18 mg of 14-0-benzoyl aconine are obtained.

Example 14 The same operation as in Example 4 was carried out except that 100 mg of 3,13-dideoxyaconitine was used instead of 3-deoxygesaconitine in Example 4, and 3,13-dideoxypyroaconitine was obtained. 60.5m
g. Next, instead of the pyrogenesaconitine of Example 1, 3,13-dideoxypyroaconitine 60 m
g, and the other operations were the same as in Example 1, and 3, 8,
50.6 mg of 13-trideoxyaconin are obtained. Next, instead of 8-oxyaconine of Example 1, 3,
45 mg of 8,13-trideoxyaconine was used, and 20 μl of benzoyl chloride was used instead of p-anisoyl chloride.
The same operation as in Example 1 was performed except for using l, and
33.2 mg of 8,13-trideoxy-14-0-benzoyl aconine are obtained.

[Example 15] Using 60 mg of pyromesaconitine in place of pyrogenesaconitine in Example 1,
Otherwise by performing the same operations as in Example 1, 47.2 mg of 8-deoxymesaconin is obtained. Next, in Example 1, 8-
8-deoxymesaconin 4 instead of deoxyaconin
Using 5 g, and using 20 μl of benzoyl chloride in place of p-anisoyl chloride, the same operation as in Example 1 is carried out, except that 34.8 mg of 8-deoxy-14-0-benzoylmesaconin is obtained.

Example 16 In place of the use of pyrogenesaconitine in Example 1, 60 mg of pyrohypaconitine was used.
Otherwise by performing the same operations as in Example 1, 46.6 mg of 3,8-dideoxymesaconin is obtained. Next, the same operation as in Example 1 was carried out except that 45 mg of 3,8-dideoxymesaconin was used instead of 8-deoxyaconine of Example 1 and 20 μl of benzoyl chloride was used instead of p-anisoyl chloride. To give 3,8-dideoxy-14
36.3 mg of-0-benzoylmesaconin are obtained.

Example 17 The procedure of Example 5 was repeated, except that 150 mg of mesaconitine was used in place of jessaconitine, to obtain 23 mg of 3,13-dideoxymesaconitine.

Example 18 The procedure of Example 3 was repeated, except that 30 mg of 3,13-dideoxymesaconitine was used in place of 3-deoxygesaconitine in Example 3, except that 3,13-dideoxymesaconitine was used. 16.8 mg of -14-0-benzoylmesaconin are obtained.

Example 19 The procedure of Example 4 was repeated except that 100 mg of 3,13-dideoxymesaconitine was used instead of 3-deoxygesaconitine. Mesaconitine 61.
Obtain 2 mg. Next, 3,13-dideoxypyrromesaconitine was used instead of pyrogenesaconitine in Example 1.
Using the same procedure as in Example 1 except for using 60 mg,
3,8,13-Trideoxymesaconin 48.7mg
Get. Next, instead of 8-deoxyaconin of Example 1, 3,8,13-trideoxymesaconin 45 m
g, and using 20 μl of benzoyl chloride in place of p-anisoyl chloride, except for the same operation as in Example 1 to obtain 31.5 mg of 3,8,13-trideoxy-14-0-benzoylmesaconin. .

Example 20 Using 60 mg of pyromesaconitine in place of pyrogenesaconitine in Example 1,
Otherwise by performing the same operations as in Example 1, 47.2 mg of 8-deoxymesaconin is obtained. Next, 8 of Example 1
-Using the same procedure as in Example 1 except for using 45 mg of 8-deoxymesaconin instead of deoxyaconin,
8-deoxy-14-0-anisoylmesaconin 32.
Obtain 5 mg.

Example 21 50 mg of hypoconitine was dissolved in a mixture of 2 ml of a 5% aqueous sodium hydroxide solution and 5 ml of methanol, and the mixture was heated under reflux for 3 hours. After cooling, the reaction solution was extracted three times with 10 ml of methylene chloride, the methylene chloride layers were combined, washed with water and dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: 15% methanol /
Ammonia-saturated chloroform) to separate, purify,
28.6 mg of 3-deoxymesaconin are obtained. 25 mg of 3-deoxymesaconin is dissolved in a mixed solution of 3 ml of pyridine and 1 ml of methylene chloride, and 10 μl of p-anisoyl chloride is added at −70 ° C. The temperature is increased from -70 ° C to -5 ° C over 2 hours while stirring the reaction. Thereafter, ice water was added to the reaction solution, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and chloroform
Extract three times with l. The chloroform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: 5% methanol / ammonia-saturated chloroform) to separate and purify 3-deoxy-14-0-anisoylmesaconin 1
8.7 mg are obtained.

Example 22 In place of the use of pyrojesaconitine in Example 1, 60 mg of pyrohypaconitine was used.
Otherwise by performing the same operations as in Example 1, 46 mg of 3,8-dideoxymesaconin is obtained. Next, in Example 21-3
-Using the same operation as in Example 21 except that 25 mg of 3,8-dideoxymesaconin was used instead of deoxymesaconin, 17.5 mg of 3,8-dideoxy-14-0-anisoylmesaconin was obtained.

Example 23 In place of hypoconitine in Example 21, 3,13-dideoxymesaconitine 50 m
g, and performing the same operations as in Example 21 except for using 3,
26.3 mg of 13-dideoxymesaconin are obtained. Next, the same operation as in Example 21 was carried out except that 25 mg of 3,13-dideoxymesaconin was used instead of 3-deoxymesaconin in Example 21, to obtain 3,13-dideoxy-14-0-anisoyyl. 17.3 mg of mesaconin are obtained.

Example 24 The procedure of Example 4 was repeated except that 100 mg of 3,13-dideoxymesaconitine was used in place of the 3-deoxygesaconitine of Example 4. Mesaconitine 6
3.7 mg are obtained. Next, 3,8,13-trideoxymesaconin was used in the same manner as in Example 1 except that 60 mg of 3,13-dideoxypyrromesaconitine was used in place of pyrogenesaconitine in Example 1. 5m
g. Next, 3,8,13-trideoxy-mesaconine was replaced with 25 mg of 3,8,13-trideoxymesaconin in the same manner as in Example 21 except that 3,8,13-trideoxy-mesaconin was used. 16.7 g of 14-0-anisoyl mesaconine are obtained.

Example 25 The same procedure as in Example 21 was repeated, except that 50 mg of mesaconitine was used instead of hypaconitine in Example 21, to obtain 30 mg of 14-0-benzoylmesaconin. Next, the same operation as in Example 21 was carried out except that 25 mg of 14-0-benzoylmesaconin was used instead of 3-deoxymesaconin of Example 21, and 15.5 mg of 14-0-anisoylmesaconin.
Get.

Example 26 72 mg of LiAlH ₄ and 0.23 ml of methanol
A THF solution containing 60 mg of 16-epipyrogesaconitine was added to a tetrahydrofuran (THF) solution of LiAl (OCH ₃ ) ₃ H prepared at −70 ° C.,
After stirring at this temperature for about 1 hour, the mixture is further stirred at room temperature for 1 hour. After completion of the reaction, wet-THF is added to the reaction solution at 0 ° C., and the precipitate is filtered. The filtrate is concentrated to dryness under reduced pressure to obtain 45.2 mg of 16-epi-8-deoxyaconin. 45 mg of 16-epi-8-deoxyaconine was dissolved in a mixture of 5 ml of pyridine and 1 ml of methylene chloride, and -7
Under 0 ° C. conditions, 15 μl of p-anisoyl chloride are added.
The temperature is increased from -70 ° C to -5 ° C over 2 hours while stirring the reaction. Thereafter, ice water was added to the reaction solution, and 5
The mixture is made alkaline with a 10% aqueous sodium hydrogen carbonate solution and extracted three times with 30 ml of chloroform. The chloroform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent:
5% methanol / ammonia-saturated chloroform), followed by separation and purification, to give 16-epi-8-deoxy-14.
35 mg of 0-anisoylaconine are obtained.

Example 27 150 mg of 3-deoxygesaconitine was heated under reduced pressure (1-2 mmHg) at 180 ° C. for 30 minutes. The reaction product was subjected to silica gel column chromatography (eluent: 5% methanol / chloroform), separated and purified, and 16-epi-3-deoxypyrrojesaconitine 6 was purified.
Obtain 3 mg. The procedure of Example 26 was repeated, except that 16-epi-3-deoxypyrrogesaconitine was used instead of 16-epipyrogesaconitine in Example 26. 14-0
-35 mg of anisoyl aconin are obtained.

Example 28 16-Epi-3 was obtained in the same manner as in Example 27 except that 150 mg of 3,13-dideoxyjesaconitine was used in place of 3-deoxyjesaconitine in Example 27. , 13-dideoxypyrogesaconitine 61.7 mg. Next, Example 26
16-epi-3,13-dideoxypyrogesaconitine instead of 16-epipyrogesaconitine
Other than that, the same operation as in Example 26 was performed, and
Epi-3,8,13-trideoxyaconin 50.1m
g. Next, instead of 16-epi-8-deoxyaconine of Example 26, 16-epi-3,8,13-
45 mg of trideoxyaconine was used, and the other was used in Example 26.
The same operation as described above was carried out, and 29.7 m of 16-epi-3,8,13-trideoxy-14-0-anisoylaconine was obtained.
g.

Example 29 In place of p-anisoyl chloride in Example 26, 20 μl of benzoyl chloride was used.
Otherwise, the same operations as in Example 26 were carried out, and 16-epi-8-
33.2 mg of deoxy-14-0-benzoyl aconine
Get.

Example 30 The procedure of Example 27 was repeated, except that 150 mg of 3-deoxyaconitine was used instead of 3-deoxygesaconitine. Aconitine 6
6.5 mg are obtained. Next, the same operation as in Example 26 was performed, except that 60 mg of 16-epi-3-deoxypyroaconitine was used instead of 16-epipyrogesaconitine in Example 26, and 16-epi-3,8 was used. -47.2 mg of dideoxyaconine are obtained. Next, 16 of Example 26
45 mg of 16-epi-3,8-dideoxyaconine was used in place of epi-8-deoxyaconin, and 20 μl of benzoyl chloride was used in place of p-anisoyl chloride.
Otherwise, the same operation as in Example 26 was performed, and
36.2 mg of epi-3,8-dideoxy-14-0-benzoylaconine are obtained.

Example 31 The same procedure as in Example 27 was repeated, except that 150 mg of 3,13-dideoxyaconitine was used instead of 3-deoxygesaconitine in Example 27. -61.2 mg of dideoxypyroconitine are obtained. Next, 16 of Example 26
-16-epi-3, instead of epipyrogesaconitine
Using the same procedure as in Example 26 except for using 60 mg of 13-dideoxypyroaconitine, 16-epi-3,
This gives 51.7 mg of 8,13-trideoxyaconine.
Next, 45 mg of 16-epi-3,8,13-trideoxyaconine was used in place of 16-epi-8-deoxyaconine in Example 26, and 20 μl of benzoyl chloride was used instead of p-anisoyl chloride. Otherwise, the same operation as in Example 26 was performed, and 16-epi-3, 8,
13-trideoxy-14.0-benzoyl aconine 3
0.5 mg is obtained.

Example 32 16-epipyromesaconitine was replaced with 16-epipyromesaconitine in 60 mg of Example 26, and the same operation as in Example 26 was carried out except for 16-epipyrosesaconitine. Deoxymesaconin 46.1
mg. Next, the 16-epi-8-
The same operation as in Example 26 was carried out except that 45 mg of 16-epi-8-5 oxymesaconine was used in place of deoxyaconin, and 20 μl of benzoyl chloride in place of p-anisoyl chloride. 34.8 mg of -deoxy-14-0-benzoylmesaconin are obtained.

Example 33 The same operation as in Example 26 was carried out except that 60-mg of 16-epipyrohypaconitine was used instead of 16-epipyrogesaconitine in Example 26, and 16-Epi-3 was used. , 8-dideoxymesaconin 4
5.8 mg are obtained. Next, the 16-epi-
16-epi-3,8- instead of 8-deoxyaconine
Using 45 mg of dideoxymesaconin, p-chloride was further added.
The same operation as in Example 26 was performed, except that 20 μl of benzoyl chloride was used instead of anisoyl, to obtain 35.7 mg of 16-epi-3,8-dideoxy-14-0-benzoylmesaconin.

Example 34 The same operation as in Example 27 was carried out except that 150 mg of 3,13-dideoxymesaconitine was used in place of 3-deoxygesaconitine in Example 27, and the same procedure as in Example 27 was carried out. 63.5 mg of 13-dideoxypyrromesaconitine are obtained. Next, Example 26
Of 16-epi-3,8,13-triene was performed in the same manner as in Example 26 except that 60 mg of 16-epi-3,13-dideoxypyrromesaconitine was used instead of 16-epipyrogesaconitine. Deoxymesaconin 49.3
mg. Next, instead of 16-epi-8-deoxyaconine of Example 26, 16-epi-3,8,13
16-epi-3,8,13-Trideoxy-14-using 45 mg of trideoxymesaconin and further using 20 μl of benzoyl chloride in place of p-anisoyl chloride, except that 30.5 mg of 0-benzoylmesaconine are obtained.

Example 35 16-Epipyromesaconitine was replaced with 16-Epipyromesaconitine 60 mg in Example 26, and the same operation as in Example 26 was carried out, except that 16-Epi-8-cone. Deoxymesaconin 45.3
mg. Next, the 16-epi-8 of the twenty-sixth embodiment
-The same operation as in Example 26 was carried out except that 45 mg of 16-epi-8-deoxymesaconin was used instead of deoxyaconin, and 16-epi-8-deoxy-14-0-
30.4 mg of anisoyl mesaconine are obtained.

Example 36 The procedure of Example 26 was repeated, except that 60 mg of 16-epipyrohypaconitine was used instead of 16-epi-pyrogesaconitine. 45 mg of 3,8-dideoxymesaconin are obtained. Next, 16-epi-3,8-dideoxymesaconine was used in place of 3-deoxymesaconine in Example 21 and 25 mg of the other steps were carried out in the same manner as in Example 21 to obtain 16-epi-3,8-. Dideoxy-14-0
-19.3 mg of anisoyl mesaconine are obtained.

Example 37 The same operation as in Example 27 was carried out except that 150 mg of 3,13-dideoxymesaconitine was used instead of 3-deoxygesaconitine in Example 27, and 16-epi-3, 62.1 mg of 13-dideoxypyrromesaconitine are obtained. Next, instead of 16-epipyrogesaconitine in Example 26, 16-epi-
Using the same procedure as in Example 26 except that 60 mg of 3,13-dideoxypyrromesaconitine was used, 31.2 m of 16-epi-3,8,13-trideoxymesaconin was used.
g. Next, 16-epi-3,8,13-trideoxymesaconin was used in place of 3-deoxymesaconin of Example 21 in an amount of 25 mg. 15.3 mg of 3,8,13-trideoxy-14-0-anisoylmesaconine are obtained.

Example 38 Pyrogesaconitine 70 was used instead of 60 mg of pyrogenicesaconitine of Example 1.
The same procedure as in Example 1 was carried out except for using mg to obtain 53 mg of 8-deoxyaconin. 8-deoxyaconine
50 mg was dissolved in 1 ml of pyridine, and 3,4,5-chloride was dissolved.
30 mg of trimethoxybenzoyl is added and stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure.
The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 28 mg of 8-deoxy-14-0-trimethylgalloylaconin was added.
Get.

Example 39 Chloride 3,4 of Example 38
3,4-chloride instead of 5-trimethoxybenzoyl
Example 38 used 25 mg of dimethoxybenzoyl and others
By the same operation as described above, 24 mg of 8-deoxy-14-0-veratroyl aconin is obtained.

Example 40 The chloride 3,3 of Example 38
Instead of 4,5-trimethoxybenzoyl, p-chloride
The same procedures as in Example 38 were carried out except using 20 mg of chlorobenzoyl to obtain 23 mg of 8-deoxy-14-0-p-chlorobenzoylaconine.

Example 41 Chloride 3,3 of Example 38
Instead of 4,5-trimethoxybenzoyl, m-chloride
Using 20 mg of chlorobenzoyl and operating in the same manner as in Example 38 except for the above, 20 mg of 8-deoxy-14-0-m-chlorobenzoylaconine is obtained.

Example 42 Chloride 3,4 of Example 38
Instead of 5-trimethoxybenzoyl, use 50 μl of α-methyl- (4- (α-methylacetic acid) -phenyl) -acetyl chloride, and operate in the same manner as in Example 38 except for 8-deoxy-14. -0-α-methyl- (4
22 mg of-([alpha] -methylacetyquaside) -phenyl) -acetylaconine are obtained.

Example 43 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. Dissolve 15 mg of 8-deoxyaconin in 1 ml of dioxane, add 15 mg of sodium hydride and stir at room temperature for 10 minutes. 0.1 ml of methyl iodide is added to the reaction solution and stirred for 2 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia saturated chloroform) to give 8-deoxy-
12 mg of 14-0-methylaconin are obtained.

Example 44 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. 30 mg of 8-deoxyaconine is dissolved in 2 ml of 1,2-dimethoxyethane, 60 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 50 μl of benzyl chloride is added to the reaction solution, and the mixture is refluxed for 3 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The cocoloform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to obtain 19 mg of 8-deoxy-14-0-benzylaconine.

Example 45 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. 17 mg of 8-deoxyaconine is dissolved in 2 ml of 1,2-dimethoxyethane, 50 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 0.5 ml of crotyl chloride is added to the reaction solution, and the mixture is refluxed for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5
% Methanol / ammonia-saturated chloroform) to give 12 mg of 8-deoxy-14-0-crotyl aconin.

Example 46 The chloride 3,3 of Example 38
O- chloride instead of 4,5-trimethoxybenzoyl
The same procedures as in Example 38 were carried out except using 20 mg of chlorobenzoyl to obtain 23 mg of 8-deoxy-14-0-o-chlorobenzoylaconine.

Example 47 Chloride 3,4 of Example 38
The same procedure as in Example 38 was repeated, except that 20 mg of m-anisoyl chloride was used instead of 5-trimethoxybenzoyl, to obtain 21 mg of 8-deoxy-14-0-m-anisoylaconine.

Example 48 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. 50 mg of 8-deoxyaconin and 20 mg of p-toluenesulfonic acid are dissolved in 1.5 ml of acetic anhydride and stirred at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (ammonia saturated ether) to obtain 35 mg of 8-deoxy-14-0-acetylaconine.

Example 49 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. 30 mg of 8-deoxyaconine was dissolved in 3.6 ml of 1,2-dimethoxyethane, and 90 mg of sodium hydride was added.
Stir for 0 minutes. 0.9 ml of 1-bromide-4-methylpentane is added to the reaction solution, and the mixture is heated under reflux for 30 minutes. After the completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 8-deoxy-14-0- (4-methylpentyl).
15 mg of aconine are obtained.

Example 50 The same operation as in Example 1 was performed.
8-Deoxy-14-0-anisoylaconine is obtained.
8-deoxy-14-0-anisoylaconine 660 m
was dissolved in 66 ml of acetone, and 25 ml of an aqueous potassium permanganate solution (887 mg / 25 ml of water) was added to this solution.
And potassium carbonate aqueous solution (556 mg / water 4.5 ml)
Add 4.5 ml and stir at room temperature for 30 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure until the smell of acetone disappeared, and 33 ml of 2N sulfuric acid and sodium thiosulfate aqueous solution (887 mg / water 22 m
l) Add 22 ml and wash with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified to obtain 649 mg of N-desethyl-8-deoxy-14-0-anisoylaconine.

Example 51 The same procedure as in Example 50 was performed to obtain N-desethyl-8-deoxy-14-0-anisoylaconine. N-desethyl-8-deoxy-
50 mg of 14-0-anisoylaconine was added to methanol /
Dissolve in 2 ml of an ether (1: 1) mixture, add 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide, and add
Heat to reflux for hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol /
Ammonia-saturated chloroform) to separate and purify
N-desethyl-N-amyl-8-deoxy-14-0
-28 mg of anisoyl aconin are obtained.

Example 52 Instead of n-amyl iodide of Example 51, 0.5 ml of n-propyl iodide was used.
Otherwise operating as in Example 51, N-desethyl-N-
26 mg of propyl-8-deoxy-14-0-anisoylaconine are obtained.

Example 53 In place of n-amyl iodide of Example 51, 0.5 m of 1-bromo-4-methylpentane was used.
l-N-desethyl-N-4-methylpentyl-8-deoxy-14
32 mg of 0-anisoylaconine are obtained.

Example 54 The same procedure as in Example 50 was carried out to obtain N-desethyl-8-deoxy-14-0-anisoylaconine. N-desethyl-8-deoxy-
50 mg of 14-0-anisoylaconine was added to methanol 1
Then, 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of acetyl chloride are added, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-acetyl-8-deoxy-1 was purified.
32 mg of 4-0-anisoylaconine are obtained.

Example 55 N-desethyl-N-benzoyl-8-deoxy-14-0 was prepared in the same manner as in Example 54 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 54. -Anisoyl aconin 28
mg.

Example 56 The same procedure as in Example 26 was repeated except that 80 mg of 16-epi-pyrogesaconitine was used in place of 60 mg of 16-epi-pyrogesaconitine in Example 26.
In the same manner as in the above, 60 mg of 16-epi-8-deoxyaconine is obtained. 16-epi-deoxyaconine 60m
g was dissolved in 1 ml of pyridine, 30 mg of 3,4,5-trimethoxybenzoyl chloride was added, and the mixture was stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 16-epi-8-
Deoxy-14-0-trimethylgalloylaconin 26
mg.

Example 57 The chloride 3,4 of Example 56
3,4-chloride instead of 5-trimethoxybenzoyl
25 mg of dimethoxybenzoyl was used.
16-epi-8-deoxy-14-0
-23 mg of veratroyl aconin are obtained.

Example 58 Chloride 3,4 of Example 56
The procedure of Example 56 was repeated, except that 20 mg of p-chlorobenzoyl chloride was used instead of 5-trimethoxybenzoyl, and 22 mg of 16-epi-8-deoxy-14-0-p-chlorobenzoylaconine was added. obtain.

Example 59 The chloride 3,4 of Example 56
The procedure of Example 56 was repeated, except that 20 mg of m-chlorobenzoyl chloride was used instead of 5-trimethoxybenzoyl, and 21 mg of 16-epi-8-deoxy-14-0-m-chlorobenzoylaconine was obtained. .

Example 60 Chloride 3,4 of Example 56
Instead of 5-trimethoxybenzoyl, 50 μl of α-methyl- (4- (α-methylacetic acid) -phenyl) -acetyl chloride was used. -Deoxy-14-0-α-
22 mg of methyl- (4-([alpha] -methylacetic acid) -phenyl) -acetylaconin are obtained.

Example 61 Instead of 60 mg of 16-epi-pyrogesaconitine in Example 26, 16-epi-
Example 2 Using 80 mg of pyrogenesaconitine and the others in Example 26
The same operation as described above is performed to obtain 60 mg of 16-epi-8-deoxyaconine. 15 mg of 16-epi-8-deoxyaconine is dissolved in 1 ml of dioxane, 15 mg of sodium hydride is added, and the mixture is stirred at room temperature for 10 minutes. 0.1 ml of methyl iodide is added to the reaction solution and stirred for 2 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia saturated chloroform) to give 16-epi-8-
11 mg of deoxy-14-0-methylaconine are obtained.

Example 62 16-Epi-pyrogesaconitine in Example 26 was replaced with 60 mg of 16-epi-
Example 2 Using 80 mg of pyrogenesaconitine and the others in Example 26
16-Epi-8-deoxyaconine
Obtain 60 mg. 16-epi-8-deoxyaconin 3
0 mg is dissolved in 2 ml of 1,2-dimethoxyethane, 60 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 50 μl of benzyl chloride was added to the reaction solution,
Heat to reflux for hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to obtain 18 mg of 16-epi-8-deoxy-14-0-benzylaconine.

Example 63 16-Epi-pyrogesaconitine of Example 26 was replaced with 60 mg of 16-epi-pyrogesaconitine
Example 2 Using 80 mg of pyrogenesaconitine and the others in Example 26
The same operation as described above is performed to obtain 16-epi-8-deoxyaconine. 17 mg of 16-epi-8-deoxyaconine is dissolved in 2 ml of 1,2-dimethoxyethane, 50 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 0.5 ml of crotyl chloride is added to the reaction solution, and the mixture is refluxed for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol /
Separation and purification with ammonia-saturated chloroform), 16
-Epi-8-deoxy-14-0-crotyl aconin 1
Obtain 2 mg.

Example 64 The chloride 3,3 of Example 56
O- chloride instead of 4,5-trimethoxybenzoyl
Using 20 mg of chloronbenzoyl and operating as in Example 56 except for using 20 mg of chloronbenzoyl, 16-epi-8-deoxy-14-0-
22 mg of o-chlorobenzoyl aconine are obtained.

Example 65 The chloride of Example 56
Instead of 4,5-trimethoxybenzoyl, m-chloride
Using 20 mg of anisoyl, otherwise following the procedure of Example 56 to obtain 20 mg of 16-epi-8-deoxy-14-0-m-anisoylaconine.

Example 66 The same procedure as in Example 26 was carried out to obtain 16-epi-8-deoxy-14-0-anisoylaconine. 16-epi-8-deoxy-14-0
-Dissolve 660 mg of anisoyl aconin in 66 ml of acetone, and add an aqueous solution of potassium permanganate (88
25 mg of 7 mg / water and 4.5 ml of an aqueous potassium carbonate solution (556 mg / 4.5 ml of water) are added, and the mixture is stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure until the acetone odor disappeared, and 33 ml of 2N sulfuric acid and 22 ml of sodium thiosulfate aqueous solution (887 mg / water 22 ml) were added to the residual solution in advance.
Wash with methylene chloride. Water layer with sodium carbonate
Adjust to H8-9 and extract with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and 16-epi-N-desethyl-8-deoxy-14.
640 mg of-0-anisoylaconine are obtained.

Example 67 The same operation as in Example 66 was carried out except that 16-epi-N-desethyl-8-deoxy-14 was used.
-O-Anisoyl aconine is obtained. 50 mg of 16-epi-N-desethyl-8-deoxy-14-0-anisoylaconine 2m mixed with methanol / ether (1: 1)
and 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide are added, and the mixture is refluxed for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform).
, And separated and purified, and 16-epi-N-desethyl-
25 mg of N-amyl-8-deoxy-14-0-anisoylaconine are obtained.

Example 68 The same operation as in Example 66 was carried out except that 16-epi-N-desethyl-8-deoxy-14 was used.
-O-Anisoyl aconine is obtained. In place of N-desethyl-8-deoxy-14-0-anisoylaconine of Example 52, 50 mg of 16-epi-N-desethyl-8-deoxy-14-0-anisoylaconine was used, and the others were carried out. Operating as in Example 52, 28 mg of 16-epi-N-desethyl-N-propyl-8-deoxy-14-0-anisoylaconine are obtained.

Example 69 In place of n-amyl iodide of Example 68, 1-bromo-4-methylpentane 0.5
Using the same procedure as in Example 68 but using 16-epi-N-desethyl-N- (4-methyl) pentyl-8.
30 mg of -deoxy-14-0-anisoylaconine are obtained.

Example 70 The same operation as in Example 66 was carried out except that 16-epi-N-desethyl-8-deoxy-14 was used.
-To obtain anisoyl aconin; 16-epi-N-desethyl-8-deoxy-in place of N-desethyl-8-deoxy-14-0-anisoylaconine of Example 54
Using the same procedure as in Example 54 except that 50 mg of 14-anisoylaconon was used, 16-epi-N-desethyl-N
29 mg of -acetyl-8-deoxy-14-0-anisoylaconine are obtained.

Example 71 The procedure of Example 70 was repeated, except that 20 μl of benzoyl chloride was used in place of the acetyl chloride of Example 70, except that 16-epi-N-desethyl-N
27 mg of -benzoyl-8-deoxy-14-0-anisoylaconine are obtained.

[Example 72] In place of benzyl chloride of Example 44, 50 µl of p-methoxybenzyl chloride was used.
Otherwise operating in the same manner as in Example 44, 8-deoxy-14-
17 mg of 0-p-methoxybenzylaconine are obtained.

Example 73 1-Bromide-4 of Example 49
Instead of -methylpentane, -n-amyl iodide.
Using 5 ml and operating in the same manner as in Example 49, 16 mg of 8-deoxy-14-0-amyl aconin is obtained.

Example 74 The procedure of Example 41 was repeated, except that 20 mg of m-bromobenzoyl chloride was used instead of m-chlorobenzoyl chloride of Example 41.
Obtain 19 mg of 8-deoxy-14-0-m-bromobenzoylaconine.

Example 75 The procedure of Example 41 was repeated, except that 20 mg of m-fluorobenzoyl chloride was used instead of m-chlorobenzoyl chloride of Example 41.
21 mg of 8-deoxy-14-0-m-fluorobenzoylaconine are obtained.

Example 76 The same operation as in Example 4 was carried out except that 100 mg of 3,13-dideoxygesaconitine was used in place of 3-deoxygesaconitine in Example 4, and 3,13-dideoxydisaconitine was used. 62 mg of pyrogenesaconitine are obtained. Next, 3,13-
The same operation as in Example 1 was performed except for using 60 mg of dideoxypyrogesaconitine, to obtain 48 mg of 3,8,13-trideoxyaconin. 30 mg of 3,8,13-trideoxyaconine is dissolved in 1 ml of pyridine, 30 mg of 3,4-dimethoxybenzoyl chloride is added, and the mixture is stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, and 5%
After making the solution alkaline with an aqueous solution of sodium hydrogen carbonate, the solution is extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified to give 3,8,13-trideoxy-1.
19 mg of 4-0-veratroyl aconin are obtained.

Example 77 The same operation as in Example 76 was carried out to obtain 3,8,13-trideoxyaconine. 3,
30 mg of 8,13-trideoxyaconine and 20 mg of p-toluenesulfonic acid are dissolved in 1.5 ml of acetic anhydride and stirred at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, and extracted with chloroform.
The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether).
31 mg of 8,13-trideoxy-14-0-acetylaconine are obtained.

Example 78 Chloride-3,4 of Example 76
The procedure of Example 76 was repeated, except that 30 mg of -m-chlorobenzoyl chloride was used instead of -dimethoxybenzoyl, to give 20 mg of 3,8,13-trideoxy-14-0-m-chlorobenzoylaconine.

Example 79 The same operation as in Example 76 was carried out to obtain 3,8,13-trideoxyaconine. 3,
Dissolve 30 mg of 8,13-trideoxyaconin in 2 ml of 1,2-dimethoxyethane, and add 60 mg of sodium hydride.
mg and stirred at room temperature for 30 minutes. 50 μl of benzyl chloride is added to the reaction solution, and the mixture is heated under reflux for 3 hours. After the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 3,8,13-trideoxy-14.
15 mg of 0-benzylaconine are obtained.

Example 80 The same operation as in Example 76 was carried out to obtain 3,8,13-trideoxyaconine. 3,
Dissolve 30 mg of 8,13-trideoxyaconin in 3.6 ml of 1,2-dimethoxyethane, add 90 mg of sodium hydride and stir at room temperature for 30 minutes. 0.9 ml of 1-bromo-4-methylpentane was added to the reaction solution,
Heat to reflux for 30 minutes. After the completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 3,8,13-trideoxy-14-0- (4-methylpentyl) aconine 1.
Obtain 4 mg.

Example 81 The same operation as in Example 76 was carried out to obtain 3,8,13-trideoxyaconine. 3,
Dissolve 30 mg of 8,13-trideoxyaconin in 4 ml of 1,2-dimethoxyethane and add 50 ml of sodium hydride.
mg and stirred at room temperature for 30 minutes. 0.8 ml of crotyl chloride is added to the reaction solution, and the mixture is heated under reflux for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to obtain 15 mg of 3,8,13-trideoxy-14-0-crotyl aconin.

Example 82 The same operation as in Example 4 was carried out to give 3,8-dideoxy-
14-0-Anisoyl aconine is obtained. The same operation as in Example 94 was performed, except that 140 mg of 3,8-dideoxy-14-0-anisoylaconine was used instead of 3,13-dideoxy-14-0-anisoylaconine in Example 94. , 62 mg of 3,8-dideoxyaconin. 50 mg of 3,8-dideoxyaconin was added to 1 m of pyridine.
l, 30 mg of 3,4-dimexibenzoyl chloride
And stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. After washing the chloroform layer with water and drying over sodium sulfate,
Concentrate to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified to obtain 3,8-dideoxy-14-0-veratroyl aconin (22 mg).

Example 83 The procedure of Example 82 was repeated to obtain 3,8-dideoxyaconine. In place of 8-deoxyaconine in Example 48, 50 mg of 3,8-dideoxyaconine was used, and the other procedures were the same as in Example 48, to obtain 37 mg of 3,8-dideoxy-14-0-acetylaconine. obtain.

Example 84 The 3,4-chloride of Example 82
The procedure of Example 82 was repeated, except that 28 mg of m-clobenzoyl chloride was used instead of dimethoxybenzoyl, and 23 mg of 3,8-dideoxy-14-0-m-chlorobenzoylaconine was obtained.

Example 85 By the same procedure as in Example 82, 3,8-dideoxyaconine was obtained. Instead of 3,8,13-trideoxyaconine of Example 79,
Example 7: 30 mg of 8-dideoxyaconin was used.
The same operation as in 9 was performed to obtain 18 mg of 3,8-dideoxy-14-0-benzylaconine.

Example 86 The procedure of Example 82 is repeated to obtain 3,8-dideoxyaconine. Instead of 3,8,13-trideoxyaconine of Example 80, 3,
Example 8 used 30 mg of 8-dideoxyaconin, and
0, the same procedure as in 3,8-dideoxy-14-0-
17 mg of (4-methyl) pentylaconin are obtained.

Example 87 The same operation as in Example 82 was carried out to obtain 3,8-dideoxyaconine. Instead of 3,8,13-trideoxyaconine in Example 8, 3,3
The procedure of Example 81 was repeated, except that 30 mg of 8-dideoxyaconin was used, and 3,8-dideoxy-14-0-
17 mg of crotyl aconin are obtained.

Example 88 Aconitine was used in the same manner as in Example 94 except that 70 mg of aconitine was used in place of 3,13-dideoxy-14-0-anisoylaconine of Example 94.
g. Instead of 3,8,13-trideoxyaconine of Example 76, 30 mg of aconine was used.
And the same procedure as in 14-0-Veratroyl aconin 1
8 mg are obtained.

Example 89 The same procedure as in Example 88 was carried out to obtain aconine. The same operation as in Example 77 was carried out except that 30 mg of aconine was used instead of 3,8,13-trideoxyaconine of Example 77, to obtain 28 mg of 14-0-acetylaconine.

Example 90 The same procedure as in Example 88 was carried out to obtain aconine. The same operation as in Example 78 was carried out except that aconine (30 mg) was used instead of 3,8,13-trideoxyaconine of Example 78, to obtain 21 mg of 14-0-m-chlorobenzoylaconine.

Example 91 The same procedure as in Example 88 was carried out to obtain aconine. The same procedure as in Example 79 was repeated, except that 30 mg of aconine was used instead of 3,8,13-trideoxyaconine in Example 79, to obtain 20 mg of 14-0-benzylaconine.

Example 92 The same procedure as in Example 88 was carried out to obtain aconine. Instead of 3,8,13-trideoxyaconine of Example 80, 30 mg of aconine was used, and the other operations were performed in the same manner as in Example 80 to obtain 14-0- (4-
20 mg of methyl) pentylaconine are obtained.

Example 93 The same procedure as in Example 88 was carried out to obtain aconine. The same procedure as in Example 81 was repeated, except that 30 mg of aconine was used instead of 3,8,13-trideoxyaconine of Example 81, to obtain 13 mg of 14-0-crotyl aconine.

Example 94 The same operation as in Example 6 was carried out, except that 3,13-dideoxy-1 was used.
4-Anisoyl aconine is obtained. 3,13-dideoxy-14-anisoylaconine 7
0 mg was dissolved in 5 ml of methanol, 1 ml of 5% potassium hydroxide was added, and the mixture was heated under reflux for 3 hours. After methanol in the reaction solution was distilled off under reduced pressure, 5 ml of water was added, and the mixture was extracted three times with 10 ml of methylene chloride. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to thin-layer chromatography (eluent: 10% methanol / ammonia-saturated chloroform), separated and purified to obtain 30,13-dideoxyaconin (30 mg). 30 mg of 3,13-dideoxyaconin was added to pyridine 1
Dissolve in 3, ml of 3,4-dimethoxybenzoyl chloride 30
mg and stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine is distilled off under reduced pressure, water is added to the residue, the mixture is made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 3,13-dideoxy-14-0.
-18 mg of veratroyl aconin are obtained.

Example 95 The same procedure as in Example 94 was carried out to obtain 3,13-dideoxyaconine. 3,
30 mg of 13-dideoxyaconine and 20 mg of p-toluenesulfonic acid are dissolved in 1.5 ml of acetic anhydride and stirred at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether) to give 3,13-
31 mg of dideoxy-14-0-acetylaconin are obtained.

[Example 96] Chloride-3,4 of Example 94
The same procedure as in Example 94 was repeated, except that 30 mg of -m-chlorobenzoyl chloride was used instead of -dimethoxybenzoyl, to obtain 15 mg of 3,13-dideoxy-14-0-m-chlorobenzoylaconine.

Example 97 By the same procedure as in Example 94, 3,13-dideoxyaconine was obtained. 3,
30 mg of 13-dideoxyaconine is dissolved in 2 ml of 1,2-dimethoxyethane, 60 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 50 μl of benzyl chloride is added to the reaction solution, and the mixture is refluxed for 3 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated by silica gel column chromatography (ammonia-saturated chloroform).
Purification gives 16 mg of 3,13-dideoxy-14-0-benzylaconine.

Example 98 By the same procedure as in Example 94, 3,13-dideoxyaconine was obtained. 3,
Dissolve 30 mg of 13-dideoxyaconin in 3.6 ml of 1,2-dimethoxyethane and add 90 m of sodium hydride.
g and stirred at room temperature for 30 minutes. 1
-Add 0.9 ml of 4-methylpentane bromide and heat to reflux for 30 minutes. After the reaction, pour the reaction solution into ice water,
Extract with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 3,13-dideoxy-14.
15 mg of -0- (4-methylpentyl) aconine are obtained.

Example 99 The same operation as in Example 94 was carried out to obtain 3,13-dideoxyaconine. 3,
30 mg of 13 dideoxyaconine is dissolved in 4 ml of 1,2-dimethoxyethane, 50 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 0.8 ml of crotyl chloride is added to the reaction solution, and the mixture is heated under reflux for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. After washing the chloroform layer with water and drying over sodium sulfate,
Concentrate to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia saturated chloroform) to give 3,13-dideoxy-1.
17 mg of 4-0-crotyl aconin are obtained.

Example 100 The same operation as in Example 3 was carried out to obtain 3-deoxy-14-anisoylaconine. Instead of 3,13-dideoxy-14-0-anisoylaconine of Example 94, 3
Using 70 mg of -deoxy-4-anisoylaconine;
Otherwise operate as in Example 94 to obtain 35 mg of 3-deoxyaconin. In the same manner as in Example 94, except that 30 mg of 3-deoxyaconine was used instead of 3,13-dideoxyaconine in Example 94, 3-deoxy-14-0-
20 mg of veratroyl aconin are obtained.

Example 101 The same operation as in Example 100 was carried out to obtain 3-deoxyaconine. 30 mg of 3-deoxyaconine and 20 mg of p-toluenesulfonic acid are dissolved in 1.5 ml of acetic anhydride and stirred at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether) to give 3-deoxy-14-O-
22 mg of acetylaconine are obtained.

Example 102 Chlorination of Example 100
Instead of 3,4-dimethoxybenzoyl, -m- chloride
Using 30 mg of chlorobenzoyl and operating in the same manner as in Example 100 except for using 30 mg of chlorobenzoyl, 17 mg of 3-deoxy-14-0-m-chlorobenzoylaconine is obtained.

Example 103 The same operation as in Example 100 was carried out to obtain 3-deoxyaconine. 30 mg of 3-deoxyaconine was dissolved in 2 ml of 1,2-dimethoxyethane, and 60 mg of sodium hydride was added.
Stir for minutes. 50 μl of benzyl chloride is added to the reaction solution, and the mixture is heated under reflux for an hour. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to obtain 14 mg of 3-deoxy-14-0-benzylaconine.

Example 104 The same operation as in Example 100 was carried out to obtain 3-deoxyaconine. 30 mg of 3-deoxyaconine was added to 3.6 ml of 1,2-dimethoxyethane.
, 90 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 0.9 ml of 1-bromide-4-methylpentane is added to the reaction solution, and the mixture is heated under reflux for 30 minutes. After the completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to obtain 16 mg of 3-deoxy-14-0- (4-methylpentyl) aconine.

Example 105 The same operation as in Example 100 was carried out to obtain 3-deoxyaconine. 30 mg of 3-deoxyaconine was dissolved in 4 ml of 1,2-dimethoxyethane, 50 mg of sodium hydride was added, and the solution was added at room temperature.
Stir for 0 minutes. 0.8 m of crotyl chloride was added to this reaction solution.
and heat to reflux for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to obtain 15 mg of 3-deoxy-14-0-crotyl aconine.

Example 106 The same operation as in Example 26 was carried out to obtain 16-epi-8-deoxyaconine. 16-epi-8 instead of 8-deoxyaconine of Example 72
Using the same procedure as in Example 72, except using 30 mg of deoxyaconine, treating 16-epi-8-deoxy-14-0-
15 mg of p-methoxybenzylaconine are obtained.

Example 107 The same operation as in Example 26 was carried out to obtain 16-epi-8-deoxyaconine. 16-epi-8 instead of 8-deoxyaconine in Example 73
-Using 30 mg of deoxyaconin, and operating in the same manner as in Example 73 except for using 16 mg of 16-epi-8-deoxy-14-0-
15 mg of amyl aconin are obtained.

Example 108 16-Epi-3 was obtained in the same manner as in Example 27, except that 150 mg of 3,13-dideoxyjesaconitine was used instead of 3-deoxyjesaconitine in Example 27. , 13-dideoxypyrrogessaconitine 61.7m
g. Next, 16-epi-3,13-dideoxypyrrojesaconitine was used in place of 16 epipyrrojesaconitine in Example 26, and the same operation as in Example 26 was carried out except for the above, to obtain 16-epi-3 , 8,13-Trideoxyaconine, 50.1 mg. 16-epi-3,8,13-trideoxyaconin 3
0 mg is dissolved in 1 ml of pyridine, 30 mg of 3,4-dimethoxybenzoyl chloride is added, and the mixture is stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 16-epi-3,8,
19 mg of 13-trideoxy-14-0-veratroyl aconin are obtained.

Example 109 Chlorination of Example 108
Instead of 3,4-dimethoxybenzoyl, -m- chloride
The procedure of Example 108 was repeated, except that 30 mg of chlorobenzoyl was used, and 21 mg of 16-epi-3,8,13-trideoxy-14-0-m-chlorobenzoylaconine was used.
Get.

Example 110 The same operation as in Example 108 is performed to obtain 16-epi-3,8,13-trideoxyaconine. 3,8,13-Trideoxyaconine 30
mg was dissolved in 2 ml of 1,2-dimethoxyethane, 60 mg of sodium hydride was added, and the mixture was stirred at room temperature for 30 minutes. 50 μl of benzyl chloride is added to the reaction solution, and the mixture is refluxed for 3 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 16-epi-3,8,
13-trideoxy-14-0-benzylaconine 16
mg.

Example 111 By following the same procedure as in Example 108, 16-epi-3,8,13-trideoxyaconine is obtained. 30 mg of 16-epi-3,8,13-trideoxyaconine was dissolved in 4 ml of 1,2-dimethoxyethane, and 50 mg of sodium hydride was added.
Stir for 0 minutes. 0.8 m of crotyl chloride was added to this reaction solution.
and heat to reflux for 30 minutes. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is separated and purified by silica gel column chromatography (5% methanol / ammonia saturated chloroform) to obtain 16 mg of 16-epi-3,8,13-trideoxy-14-0-crotyl aconin.

Example 112 The same operation as in Example 27 was performed, except that 3-deoxyaconitine was used in place of 3-deoxydisaconitine in Example 27, and 150-mg of 16-epi-3-deoxypyrroone was used. 66.5 mg of aconitine are obtained. Next, instead of 16-epipyrrogessaconitine in Example 26, 1
Using the same procedure as in Example 26 except that 60 mg of 6-epi-3-deoxypyroaconitine is used, 47.2 mg of 16-epi-3,8-dideoxyaconine is obtained. 40 mg of 16-epi-3,8-dideoxyaconine is dissolved in 1 ml of pyridine, 30 mg of 3,4-dimethoxybenzoyl chloride is added, and the mixture is stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, and water was added to the residue.
After making it alkaline with 5% sodium hydrogen carbonate aqueous solution,
Extract with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is subjected to silica gel column chromatography (ammonia saturated ether), separated and purified to obtain 20 mg of 16-epi-3,8-dideoxy 14-0-veratroyl aconin.

Example 113 The chloride 3,3 of Example 112
The procedure of Example 112 was repeated, except that 28 mg of m-chlorobenzoyl chloride was used instead of 4-dimethoxybenzoyl, and 16-epi-3,8-dideoxy-14-0 was used.
22 mg of -m-chlorobenzoylaconine are obtained.

Example 114 By following the same procedure as in Example 112, 16-epi-3,8-dideoxyaconine is obtained. In place of 3,8,13-trideoxyaconine of Example 79, 30 mg of 16-epi-3,8-dideoxyaconine was used, and the other procedures were the same as in Example 79.
-19 mg of epi-3,8-dideoxy-14-0-benzylaconine are obtained.

Example 115 By following the same procedure as in Example 112, 16-epi-3,8-dideoxyaconine is obtained. In place of 3,8,13-trideoxyaconine of Example 81, 30 mg of 16-epi-3,8-dideoxyaconine was used.
15 mg of epi-3,8-dideoxy-14-0-crotyl aconin are obtained.

Example 116 The same operation as in Example 4 was carried out to obtain 3,8-dideoxy-14-0-anisoylaconine. 660 mg of 3,8-dideoxy-14-0-anisoylaconine was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / water 2) was added to the solution.
5 ml) and an aqueous potassium carbonate solution (556 mg)
(4.5 ml of water / 4.5 ml of water) and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure until there was no smell of acetone, and the solution was cooled to a residual solution in advance.
33 ml of N sulfuric acid and an aqueous solution of sodium thiosulfate (88
(7 mg / water 22 ml), and wash with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified to obtain 630 mg of N-desethyl-3,8-dideoxy-14-0-anisoylaconine.

Example 117 The same procedure as in Example 116 was carried out except that N-desethyl-3,8-dideoxy-14-0 was used.
-To obtain anisoyl aconin; N-desethyl-3,8
-Dideoxy-14-0-anisoylaconine 50mg
Was dissolved in 2 ml of a methanol / ether (1: 1) mixture, 65 mg of calcium carbonate and 0.1 ml of n-amyl iodide were added.
Add 2 ml and heat to reflux for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform) to separate and purify, and N-desethyl-N-amyl-3,
8-dideoxy-14-O-anisoylaconine 25m
g.

Example 118 n-iodide of Example 117
-Using 0.5 ml of n-propyl iodide instead of amyl and operating in the same manner as in Example 117, except that 22 mg of N-desethyl-N-propyl-3,8-dideoxy-14-0-anisoylaconine was used. Get.

[Example 119] n-iodide of Example 117
1-bromide-4-methylpentane instead of amyl
Using the same procedure as in Example 117 except for using 5 ml, N-
31 mg of desethyl-N-4-methylpentyl-3,8-dideoxy-14-0-anisoylaconine are obtained.

Example 120 The same procedures as in Example 116 were carried out except that N-desethyl-3,8-dideoxy-14-0 was used.
-To obtain anisoyl aconin; N-desethyl-3,8
-Dideoxy-14-0-anisoylaconine 50mg
Is dissolved in 1 ml of methanol, 50 mg of potassium carbonate,
0.1 ml of water and 20 μl of acetyl chloride are added, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify, and N-desethyl-N-acetyl-
3,8-dideoxy-14-0-anisoylaconine 3
0 mg is obtained.

Example 121 N-desethyl-N-benzoyl-3,8-dideoxy-14 was prepared in the same manner as in Example 120 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 120. 25 mg of-0-anisoylaconine are obtained.

Example 122 The procedure of Example 7 was repeated to obtain 3,8,13-trideoxy-14-0-anisoylaconine. 3,8,13-trideoxy-14
660 mg of-0-anisoylaconine is added to 66 m of acetone.
The resulting solution is added with 25 ml of an aqueous solution of potassium permanganate (887 mg / 25 ml of water) and 4.5 ml of an aqueous solution of potassium carbonate (556 mg / 4.5 ml of water), and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution is concentrated under reduced pressure until the acetone odor disappears, 33 ml of 2N sulfuric acid and 22 ml of a sodium thiosulfate aqueous solution (887 mg / 22 ml of water) are added to the remaining solution, and the mixture is washed with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure.
The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified to obtain 620 mg of N-desethyl-3,8,13-trideoxy-14-0-anisoylaconine.

Example 123 The same procedure as in Example 122 was repeated, except that N-desethyl-3,8,13-trideoxy-
14-0-Anisoyl aconine is obtained. 50 mg of N-desethyl-3,8,13-trideoxy-14-0-anisoylaconine was dissolved in 2 ml of a methanol / ether (1: 1) mixture, and 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide were added. Heat to reflux for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to Ricagel column chromatography (5% methanol / ammonia-saturated chlororum), separated and purified, and N-desethyl-N-amyl-3,8,13-trideoxy-14-0-anisoylaconine 21 mg was used. Get.

[Example 124] n-iodide of Example 123
N-desethyl-N-propyl-3,8,13-trideoxy-14-substituted in the same manner as in Example 123 except that 0.5 ml of n-propyl iodide was used instead of amyl.
20 mg of 0-anisoylaconine are obtained.

Example 125 n-iodide of Example 123
1-bromide-4-methylpentane instead of amyl
Using the same procedure as in Example 123, except using 5 ml, N-
Desethyl-N-4-methylpentyl-3,8,13-
Trideoxy-14-0-anisoylaconine 31mg
Get.

Example 126 The same procedure as in Example 122 was repeated, except that N-desethyl-3,8,13-trideoxy-
14-0-Anisoyl aconine is obtained. Dissolve 50 mg of N-desethyl-3,8,13-trideoxy-14-0-anisoylaconine in 1 ml of methanol, and add 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of acetyl chloride.
and stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was concentrated to dryness under reduced pressure, and the residue was concentrated in 20 ml of chloroform.
, And the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify, and N, desethyl-N
-Acetyl-3,8,13-trideoxy-14-0-
28 mg of anisoyl aconin are obtained.

Example 127 N-Desethyl-N-benzoyl-3,8,13-trideoxy was obtained in the same manner as in Example 126 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 126. 25 mg of -14-0-anisoylaconine are obtained.

Example 128 Aconitine was used in the same manner as in Example 94 except that 70 mg of aconitine was used in place of 3,13-dideoxy-14-0-anisoylaconine in Example 94.
g. Aconine (45 mg) is dissolved in a mixture of pyridine (5 ml) and methylene chloride (1 ml), and p-anisoyl chloride (18 μl) is added at −70 ° C. The temperature is increased from -70 ° C to -5 ° C over 2 hours while stirring the reaction. Thereafter, ice water is added to the reaction solution, the mixture is made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted three times with 30 ml of chloroform. The chloroform layers are combined, washed with water and dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: 5% methanol /
Ammonia-saturated chloroform) to separate, purify,
38 mg of 14-anisoyl aconin are obtained. 14-0-
660 mg of anisoyl aconine was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887
(25 mg / water 25 ml) and 4.5 ml of an aqueous potassium carbonate solution (556 mg / 4.5 ml of water) are added, followed by stirring at room temperature for 30 minutes. After completion of the reaction, the reaction mixture is concentrated under reduced pressure until the smell of acetone disappears, and 33 ml of 2N sulfuric acid and 22 ml of a sodium thiolutate aqueous solution (887 mg / 22 ml of water), which have been cooled in advance, are added to the remaining liquid, followed by washing with methylene chloride. The aqueous layer is pH 8 with sodium carbonate
Adjust to ~ 9 and extract with methylene chloride. The methylene chloride eyebrows are dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify.
N-desethyl-14-0-anisoyl aconine 640
mg.

Example 129 The same operation as in Example 128 is performed to obtain N-desethyl-14-0-anisoylaconine. 50 mg of N-desethyl-14-0-anisoylaconine mixed with methanol / ether (1: 1) 2
of calcium carbonate 65 mg and n-iodide
Add 0.2 ml of amyl and heat to reflux for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified to obtain 29 mg of N-desethyl-N-amyl-14-0-anisoylaconine.

[Example 130] n-iodide of Example 129
-Using 0.5 ml of n-propyl iodide instead of amyl, and operating in the same manner as in Example 129 except for using 23 ml of N-desethyl-N-propyl-14-0-anisoylaconine.
g.

Example 131 n-iodide of Example 129
1-bromide-4-methylpentane instead of amyl
The procedure of Example 51 is repeated except for using 5 ml to obtain 30 mg of N-desethyl-N-4-methylpentyl-14-0-anisoylaconine.

Example 132 The procedure of Example 128 was repeated to obtain N-desethyl-14-0-anisoylaconine. 50 mg of N-desethyl-14-0-anisoylaconine was dissolved in 1 ml of methanol. Then, 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of acetyl chloride are added, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified to obtain 31 mg of N-desethyl-N-acetyl-14-0-anisoylaconine.

Example 133 The procedure of Example 132 was repeated, except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 132. The procedure of Example 132 was repeated, except that N-desethyl-N-benzoyl-14-0-anisoyl alcohol was used. 25 mg of nin are obtained.

Example 134 The same operation as in Example 3 was carried out to obtain 3-deoxy-14-0-anisoylaconine. 3-deoxy-14-0-anisoylaconine 66
0 mg was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / 25 ml of water) 25 was added to this solution.
ml and an aqueous potassium carbonate solution (556 mg / 4.5 m water)
l) Add 4.5 ml and stir at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure until the smell of acetone disappeared.
l and an aqueous solution of sodium thiosulfate (887 mg / water 2
2 ml) and add 22 ml, and wash with methylene chloride.
The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. After drying the methylene chloride layer with sodium sulfate,
Concentrate to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified to obtain 600 mg of N-desethyl-3-deoxy-14-0-anisoylaconine.

Example 135 The procedure of Example 134 is repeated to obtain N-desethyl-3-deoxy-14-0-anisoylaconine. 50 mg of N-desethyl-3-deoxy-14-0-anisoylaconine was dissolved in 2 ml of a methanol / ether (1: 1) mixture, 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide were added, and the mixture was heated under reflux for 2 hours. I do. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified, and N-desethyl-N-amyl-3-deoxy-14 was purified.
25 mg of-0-anisoylaconine are obtained.

[Example 136] n-iodide of Example 135
-Using 0.5 ml of n-propyl iodide instead of amyl and operating in the same manner as in Example 135, except that 22 mg of N-desethyl-N-propyl-3-deoxy-14-0-anisoylaconine is obtained. .

Example 137 The n-iodide of Example 135
1-bromide-4-methylpentane instead of amyl
Using the same procedure as in Example 135 except for using 5 ml, N-
Desethyl-N-4-methylpentyl-3-deoxy-
30 mg of 14-0-anisoylaconine are obtained.

Example 138 The procedure of Example 134 is repeated to obtain N-desethyl-3-deoxy-14-0-anisoylaconine. 50 mg of N-desethyl-3-deoxy-14-0-anisoylaconine was dissolved in 1 ml of methanol, and 50 mg of potassium carbonate and 0.1 ml of water were dissolved.
And 20 μl of acetyl chloride, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified, and N-desethyl-N-acetyl-3-deoxy-1 was purified.
30 mg of 4-0-anisoylaconon are obtained.

Example 139 N-desethyl-N-benzoyl-3-deoxy-14-0 was prepared in the same manner as in Example 138 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 138. 24 mg of -7 nisoyl aconin are obtained.

Example 140 By the same procedure as in Example 6, 3,13-dideoxy-14-0-anisoylaconine was obtained. 660 mg of 3,13-dideoxy-14-0-anisoylaconine was dissolved in 66 ml of acetone,
An aqueous solution of potassium permanganate (887 mg /
25 ml of water and an aqueous solution of potassium carbonate (556)
(4.5 ml of water / 4.5 ml of water).
Stir for minutes. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure until the smell of acetone disappeared.
(87 mg / water 22 ml) and wash with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified to obtain 611 mg of N-desethyl-3,13-dideoxy-14-0-anisoylaconine.

Example 141 The same procedure as in Example 140 was carried out, except that N-desethyl-3,13-dideoxy-14 was obtained.
0-Anisoyl aconine is obtained. N-desethyl-3,
13-dideoxy-14-0-anisoylaconine 50
is dissolved in 2 ml of a mixed solution of methanol / ether (1: 1), 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide are added, and the mixture is heated under reflux for 2 hours. After the reaction,
The insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform, separated and purified), and N-desethyl-N-amyl-3,
13-dideoxy-14-0-anisoylaconine 22
mg.

Example 142 n-iodide of Example 141
-Using 0.5 ml of n-propyl iodide instead of amyl and operating in the same manner as in Example 141 except that 26 mg of N-desethyl-N-propyl-3,13-dideoxy-14-0-anisoylaconine was used. Get.

[Example 143] n-iodide of Example 141
1-bromide-4-methylpentane instead of amyl
Using the same procedure as in Example 141, except using 5 ml, N-
30 mg of desethyl-N-4-methylpentyl-3,13-dideoxy-14-0-anisoylaconine are obtained.

[Example 144] The same procedure as in Example 140 was repeated, except that N-desethyl-3,13-dideoxy-14- was obtained.
0-Anisoyl aconine is obtained. N-desethyl-3,
13-dideoxy-14-0-anisoylaconine 50
mg in 1 ml of methanol.
g, 0.1 ml of water and 20 μl of acetyl chloride, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-acetyl-
31 mg of 3,13-dideoxy-14-0-anisoylaconine are obtained.

Example 145 N-desethyl-N-benzoyl-3,13-dideoxy-14 was prepared in the same manner as in Example 144 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 144. 28 mg of-0-anisoylaconine are obtained.

Example 146 The same procedure as in Example 27 is performed to obtain 16-epi-3,8-dideoxy-14-0-anisoylaconine. 660 mg of 16-epi-3,8-dideoxy-14-0-anisoylaconine is dissolved in 66 ml of acetone, and 25 ml of an aqueous solution of potassium permanganate (887 mg / 25 ml of water) and an aqueous solution of potassium carbonate (556 mg / water 4. 5 ml) 4.5 ml
And stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure until the smell of acetone disappeared, and 33 ml of 2N sulfuric acid and 22 ml of a sodium thiosulfate aqueous solution (887 mg / water 22 ml) cooled in advance to the residual liquid.
And washed with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-16-epi-3,8-
Dideoxy-14-0-anisoylaconine 615mg
Get.

Example 147 The procedure of Example 146 is repeated to obtain N-desethyl-16-epi-3,8-deoxy-14-0-anisoylaconine. 50 mg of N-desethyl-16-epi-3,8-dideoxy-14-0-anisoylaconin was added to methanol / ether (1:
1) Dissolve in 2 ml of the mixture, add 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide, and heat to reflux for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-amyl-16-epi-3,8-dideoxy-14 was purified.
21 mg of -0-anisoylaconine are obtained.

[Example 148] n-iodide of Example 147
N-desethyl-N-propyl-16-epi-3,8-dideoxy-1 was prepared in the same manner as in Example 147 except that 0.5 ml of n-propyl iodide was used instead of amyl.
23 mg of 4-0-anisoylaconine are obtained.

[Example 149] n-iodide of Example 147
1-bromide-4-methylpentane instead of amyl
The same operation as in Example 147 was carried out except that 5 ml was used.
Desethyl-N-4-methylpentyl-16-epi-
3,8-dideoxy-14-0-anisoylaconine 2
Get 9mg

Example 150 The same procedure as in Example 146 was carried out to obtain N-desethyl-16-epi-3,8-dideoxy-14-0-anisoylaconine. Dissolve 50 mg of N-desethyl-16-epi-3,8-dideoxy-14-0-anisoylaconine in 1 ml of methanol, add 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of acetyl chloride, and stir at room temperature for 1 hour. I do. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-acetyl-16-epi-3,8-dideoxy-14-0-anisoyl alcohol was purified. 31 mg of nin are obtained.

Example 151 N-desethyl-N-benzoyl-16-epi-3,8 was prepared in the same manner as in Example 120 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 150. -Dideoxy-14-0
-22 mg of anisoyl aconin are obtained.

Example 152 The same procedures as in Example 28 were carried out except that 16-epi-3,8,13-trideoxy-14-0 was used.
-To obtain anisoyl aconin; 16-epi-3,8,1
3-Trideoxy-14-0-anisoylaconine 66
0 mg was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / 25 ml of water) 2 was added to this solution.
5 ml and an aqueous potassium carbonate solution (556 mg / water 4.5)
ml) and stirred at room temperature for 30 minutes.
After the completion of the reaction, the reaction solution was concentrated under reduced pressure until the acetone odor disappeared, and 2N sulfuric acid 33 previously cooled was added to the remaining solution.
ml and an aqueous solution of sodium thiosulfate (887 mg / water 2
2 ml) and add 22 ml, and wash with methylene chloride.
The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. After drying the methylene chloride eyebrows with Glauber's salt,
Concentrate to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify the residue.
-615 mg of epi-3,8,13-trideoxy-14-0-anisoylaconine are obtained.

Example 153 The procedure of Example 152 is repeated to obtain N-desethyl-16-epi-3,8,13-trideoxy-14-0-anisoylaconine. N
Dissolve 50 mg of -desethyl-16-epi-3,8,13-trideoxy-14-0-anisoylaconine in 2 ml of a methanol / ether (1: 1) mixture, and obtain 65 mg of calcium carbonate and 0.2 ml of n-amyl iodide. And heat to reflux for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-amyl-16epi-3,
21 mg of 8,13-trideoxy-14-0-anisoylaconine are obtained.

Example 154 The n-iodide of Example 153
N-desethyl-N-propyl-16-epi-3,8,13-trideoxy-14 was prepared in the same manner as in Example 153 except that 0.5 ml of n-propyl iodide was used instead of amyl. 20 mg of 0-anisoylaconine are obtained.

Example 155 n-iodide of Example 153
1-bromide-4-methylpentane instead of amyl
Using 5 ml, operating in the same manner as in Example 153,
Desethyl-N-4-methylpentyl-16-epi-
29 mg of 3,8,13-trideoxy-14-0-anisoylaconine are obtained.

Example 156 The procedure of Example 152 is repeated to obtain N-desethyl-16-epi-3,8,13-trideoxy-14-0-anisoylaconine. N
Dissolve 50 mg of desethyl-16-epi-3,8,13-trideoxy-14-0-anisoylaconine in 1 ml of methanol, and add 50 mg of potassium carbonate and 0.1 m of water.
and 20 μl of acetyl chloride, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform) to separate and
Purified, N-desethyl-N-acetyl-16-epi-
25 mg of 3,8,13-trideoxy-14-0-anisoylaconine are obtained.

Example 157 N-desethyl-N-benzoyl-16-epi-3,8 was prepared in the same manner as in Example 126 except that 20 μl of benzoyl chloride was used instead of acetyl chloride of Example 156. , 13-Trideoxy-
22 mg of 14-0-anisoylaconin are obtained.

Example 158 70 mg of pyrogesaconitine was dissolved in 5 ml of a 90% aqueous methanol solution, 15 mg of potassium carbonate was added, and the mixture was stirred at room temperature for 40 hours. After methanol in the reaction solution was distilled off under reduced pressure, 5 ml of water was added, and the mixture was extracted three times with 10 ml of methylene chloride. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to thin layer chromatography (eluent: 1
0% methanol / ammonia-saturated chloroform), separated and purified, and 30 mg of 16-epi-pyroaconin was added.
Get. 30 mg of 16-epi-pyroaconin is added to 1 ml of pyridine
And added with 20 mg of m-chlorobenzoyl chloride,
Stir at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue is subjected to silica gel column chromatography (ammonia saturated ether), separated and purified to obtain 14-0-m-chlorobenzoyl-16-epi-pyroaconine (12 mg).

Example 159 The same procedure as in Example 158 was carried out to obtain 16-epi-pyroaconine. 30 mg of 16-epi-pyroaconin and p-toluenesulfonic acid 2
Dissolve 0 mg in 1.5 ml of acetic anhydride and stir at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, the chloroform layer extracted with chloroform was washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure. Harden. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether) to give 14-0-acetyl-16.
-11 mg of epi-pyroaconin are obtained.

Example 160 By following the same procedure as in Example 158, 16-epi-pyroaconine is obtained. Dissolve 30 mg of 16-epi-pyroaconin in 1 ml of dioxane,
Add 15 mg of sodium hydride and stir at room temperature for 10 minutes. 0.1 ml of methyl iodide is added to the reaction solution and stirred for 2 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia saturated chloroform).
14-0-methyl-16-epi-pyroaconine 10 mg
Get.

Example 161 Pyrogesaconitine (660 mg) was dissolved in acetone (66 ml), and a potassium permanganate aqueous solution (88
25 ml of 7 mg / 25 ml of water) and 4.5 ml of an aqueous potassium carbonate solution (556 mg / 4.5 ml of water) are added, and the mixture is stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution is concentrated under reduced pressure until the acetone odor disappears, 33 ml of 2N sulfuric acid and 22 ml of a sodium thiosulfate aqueous solution (887 mg / 22 ml of water) are added to the remaining solution, and the mixture is washed with methylene chloride. The aqueous layer is pH 8 with sodium carbonate
Adjust to ~ 9 and extract with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify.
-N-desethyl-16-epi-pyrogesaconitine 4
Obtain 80 mg. N-desethyl-16-epi-pyrogesaconitine 5
0 mg was dissolved in 1 ml of methanol, and potassium carbonate 50
mg, 0.1 ml of water and 20 μl of benzoyl chloride, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, the chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified to obtain 20 mg of N-desethyl-N-benzoyl-16-epi-pyrogesaconitine.

Example 162 The procedure of Example 161 was repeated to obtain N-desethyl-16-epi-pyrrojesaconitine. N-desethylpyrogesaconitine 50m
g was dissolved in 2 ml of a methanol / ether (1: 1) mixed solution, 65 mg of calcium carbonate and 0.5 ml of n-propyl iodide were added, and the mixture was heated under reflux for 2 hours. After the reaction,
The insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify, and N-desethyl-N-propyl-
28 mg of 16-epi-pyrogesaconitine are obtained.

Example 163 N-desethyl-N-acetyl-16-epi-pyrogesaconitine was prepared in the same manner as in Example 162 except that 20 μl of anisoyl chloride was used instead of benzoyl chloride of Example 161. 22 mg are obtained.

Example 164 The procedure of Example 2 was repeated, except that 100 mg of pyrogenesaconitine was used instead of gesaconitine in Example 2, except that 35 mg of 3-deoxypyrrojesaconitine was obtained.
35 mg of 3-deoxypyrogesaconitine is dissolved in 3 ml of a 90% aqueous methanol solution, 10 mg of potassium carbonate is added, and the mixture is stirred at room temperature for 40 hours. After methanol in the reaction solution was distilled off under reduced pressure, 5 ml of water was added, and methylene chloride was added.
Extract three times with ml. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to thin-layer chromatography (eluent: 10% methanol / ammonia-saturated chloroform), separated and purified to obtain 20 mg of 3-deoxy-16-epi-pyroaconin. 20 mg of 3-deoxy-16-epi-pyroaconin was dissolved in 1 ml of pyridine, and 20 ml of chlorobenzoyl chloride was dissolved.
g and stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, water was added to the residue, the mixture was made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether),
Separation and purification yield 10 mg of 3-deoxy-14-0-m-chlorobenzoyl-16-epi-pyroaconine.

Example 165 The same procedure as in Example 164 was performed to obtain 3-deoxy-16-epi-pyroaconine. 20 mg of 3-deoxy-16-epi-pyroaconin
And 20 mg of p-toluenesulfonic acid in 1.5 ml of acetic anhydride.
Dissolve in the solution and stir at room temperature for 1 hour. After the reaction,
Acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, and the mixture was made alkaline with 5% sodium hydrogen carbonate and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether) to give 3-deoxy-14-0-acetyl-16-epi-
10 mg of piroaconin are obtained.

Example 166 The same operation as in Example 164 was performed to obtain 3-deoxy-16-epi-pyroaconine. 20 mg of 3-deoxy-16-epi-pyroaconin
Is dissolved in 1 ml of dioxane and sodium hydride 15m
g and stirred at room temperature for 10 minutes. 0.1 ml of methyl iodide is added to the reaction solution and stirred for 2 hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. After washing the chloroform layer with water and drying over sodium sulfate,
Concentrate to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to give 3-deoxy-14-0-
10 mg of methyl-16-epi-pyroaconin are obtained.

Example 167 The procedure of Example 2 was repeated, except that 300 mg of pyrogenesaconitine was used in place of jessaconitine in Example 2, except that 100 mg of 3-deoxypyrrojesaconitine was obtained. Dissolve 300 mg of 3-deoxypyrogesaconitine in 66 ml of acetone, and add 25 ml of an aqueous potassium permanganate solution (887 mg / 25 ml of water) and 4.5 m of an aqueous potassium carbonate solution (556 mg / 4.5 ml of water).
and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure until the smell of acetone disappeared, and the residue was cooled to 33 ml of 2N sulfuric acid and 22 ml of an aqueous sodium thiosulfate solution (887 mg / water 22 ml).
Add 1 and wash with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified, and N-desethyl-3-deoxy-16 was purified.
-Obtain 250 mg of epi-pyrogesaconitine. 50 mg of N-desethyl-3-deoxy-16-epi-pyrogesaconitine is dissolved in 1 ml of methanol, 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of benzoyl chloride are added, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution is concentrated to dryness under reduced pressure, the residue is dissolved in 20 ml of chloroform, chloroform eyebrows are washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-N-benzoyl-3-deoxy-16-epi-epi-
20 mg of pyrogenesaconitine are obtained.

Example 168 The same procedure as in Example 167 was carried out to obtain N-desethyl-3-deoxy-16-epi-pyrogesaconitine. 50 mg of N-desethyl-3-deoxy-16-epi-pyrogesaconitine is dissolved in 2 ml of a methanol / ether (1: 1) mixture, 65 mg of calcium carbonate and 0.5 ml of n-propyl iodide are added, and the mixture is heated under reflux for 2 hours. I do. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform) to separate and
Purification gives 28 mg of N-desethyl-N-propyl-3-deoxy-16-epi-pyrogesaconitine,

Example 169 The procedure of Example 167 was repeated, except that 20 μl of anisoyl chloride was used instead of benzoyl chloride. 20 mg of pyrogenesaconitine are obtained.

Example 170 The procedure of Example 5 was repeated, except that 100 mg of pyrogenesaconitine was used in place of jessaconitine in Example 5, except that 35 mg of 3,13-dideoxypyrrogesaconitin was used.
Get. 3,13-dideoxypyrrogessaconitine 35
mg was dissolved in a 90% aqueous methanol solution 31, 10 mg of potassium carbonate was added, and the mixture was stirred at room temperature for 40 hours. After methanol in the reaction solution was distilled off under reduced pressure, 5 ml of water was added, and the mixture was extracted three times with 10 ml of methylene chloride. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to thin layer chromatography (eluent: 10% methanol / ammonia saturated chloroform), separated and purified to obtain 3,13-dideoxy-16-epi-pyroaconine (20 mg). 3,13-dideoxy-16-epi-pyroaconin 2
0 mg is dissolved in 1 ml of pyridine, 20 mg of m-chlorobenzoyl chloride is added, and the mixture is stirred at 80 ° C. for 4 hours. After completion of the reaction, pyridine was distilled off under reduced pressure, and water was added to the residue.
The mixture is made alkaline with a 5% aqueous sodium hydrogen carbonate solution and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 3,13-dideoxy-14-
10 mg of 0-m-chlorobenzoyl-16-epi-pyroaconine are obtained.

Example 171 The same operation as in Example 170 was carried out to obtain 3,13-dideoxy-16-epi-pyroaconine. 3,13-dideoxy-16-epi-pyroaconine 20 mg and p-toluenesulfonic acid 20 mg
Is dissolved in 1.5 ml of acetic anhydride and stirred at room temperature for 1 hour. After completion of the reaction, acetic anhydride was distilled off under reduced pressure, ice water was added to the residue, the mixture was made alkaline with 5% sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia saturated ether) to give 3,13-dideoxy-1.
4-0-acetyl-16-epi-pyroaconin 10 mg
Get.

Example 172 The same operation as in Example 170 was carried out to obtain 3,13-dideoxy-16-epi-pyroaconine. Dissolve 20 mg of 3,13-dideoxy-16-epi-pyroaconine in 1 ml of dioxane, add 15 mg of sodium hydride and stir at room temperature for 10 minutes. 0.1 ml of methyl iodide was added to the reaction solution, and 2
Stir for hours. After completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol /
Separation and purification with ammonia-saturated chloroform)
10 mg of 13-dideoxy-14-0-methyl-16-epi-pyroaconine are obtained.

Example 173 The procedure of Example 5 was repeated, except that 300 mg of pyrogesaconitine was used instead of jessaconitine in Example 5, except that 100 mg of 3,13-dideoxypyrrojesaconitine was used.
g. 3,13-dideoxypyrogesaconitin 1
Was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / 25 ml of water) 2 was added to this solution.
5 ml and an aqueous potassium carbonate solution (556 mg / water 4.5)
ml) and stirred at room temperature for 30 minutes.
After the completion of the reaction, the reaction solution was concentrated under reduced pressure until the acetone odor disappeared, and 2N sulfuric acid 33 previously cooled was added to the remaining solution.
ml and an aqueous solution of sodium thiosulfate (887 mg / water 2
2 ml) and add 22 ml, and wash with methylene chloride.
The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. After drying the methylene chloride layer with sodium sulfate,
Concentrate to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified, and N-desethyl-3,1 was purified.
3-dideoxy-16-epi-pyrogesaconitine 60
mg. 50 mg of N-desethyl-3,13-dideoxy-16-epi-pyrogesaconitine is dissolved in 1 ml of methanol, 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of benzoyl chloride are added, and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was concentrated to dryness under reduced pressure, the residue was dissolved in 20 ml of chloroform, and the chloroform layer was washed with water.
After drying with sodium sulfate, the mixture is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify,
Desethyl-N-benzoyl-3,13-dideoxy-
20 mg of 16-epi-pyrogesaconitine are obtained.

Example 174 The same operation as in Example 173 was carried out, except that N-desethyl-3,13-dideoxy-16 was obtained.
-To obtain epi-pyrogesaconitine. N-desnitil-
50 mg of 3,13-dideoxy-16-epi-pyrogesaconitine was mixed with methanol / ether (1: 1) 2m.
and 65 mg of calcium carbonate and 0.5 ml of n-propyl iodide are added, and the mixture is refluxed for 2 hours. After completion of the reaction, insolubles in the reaction solution are removed by filtration, and the reaction solution is concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia saturated chloroform), separated and purified to obtain 28 mg of N-desethyl-N-propyl-3,13-dideoxy-16-epi-pyrogesaconitine. .

Example 175 N-desethyl-N-acetyl-3,13-dideoxy-16 was used in the same manner as in Example 173 except that 20 μl of acetyl chloride was used instead of benzoyl chloride of Example 173. 20 mg of epi-pyrogesaconitine are obtained.

Example 176 The procedure of Example 50 was repeated to obtain N-desethyl-8-deoxy-14-0-anisoylaconine. N-desethyl-8-deoxy-
50 mg of 14-0-anisoylaconine was added to methanol 1
in 50 ml of potassium carbonate, 0.1 ml of water and 2-methyl-tetrahiro-2-furoyl chloride 20.
Add μl and stir at room temperature for 1 hour. After completion of the reaction, the reaction solvent was distilled off under reduced pressure, the residue was dissolved in 20 ml of chloroform, and the chloroform layer was washed with 5% hydrochloric acid and water.
It is dried over sodium sulfate and concentrated to dryness under reduced pressure. Next, the residue was dissolved in 1.5 ml of tetrahydrofuran, and this solution was
In advance, add 20 mg of lithium aluminum hydride to 0.1 mg.
It is added while cooling to a solution suspended in 7 ml of tetrahydrofuran, and the mixture is heated under reflux for 2 hours. After completion of the reaction, 0.1 ml of water is added to the reaction solution, followed by filtration. The filtrate is concentrated to dryness under reduced pressure, the residue is dissolved in 1 ml of pyridine, 20 μl of p-anisoyl chloride is added, and the mixture is stirred at room temperature for 4 hours. After completion of the reaction, pyridine in the reaction solution was distilled off under reduced pressure, water was added, and the mixture was made alkaline with 5% sodium hydrogen carbonate.
Extract with chloroform. The chloroform layer is washed with saturated saline, dried over sodium sulfate, and distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform).
-Desethyl-N- (2-methyltetrahydrofurfuryl) -8-deoxy-14-0-anisoylaconine 2
Obtain 1 mg.

Example 177 The same procedures as in Example 116 were carried out except that N-desethyl-3,8-dideoxy-14-0 was used.
-To obtain anisoyl aconin; N-desethyl-3,8-dideoxy-14 in place of N-desethyl-8-deoxy-14-0-anisoylaconine of Example 176
Using the same procedures as in Example 176 but using 50 mg of -0-anisoylaconine, N-desethyl-N- (2
-Methyltetrahydrofurfuryl) -3,8-dideoxy-14-0-anisoylaconine 20m is obtained.

Example 178 The same procedure as in Example 122 was repeated, except that N-desethyl-3,8,13-trideoxy-
14-0-Anisoyl aconine is obtained. The procedure of Example 176 was repeated, except that 50 mg of N-desethyl-3,8,13-trideoxy-14-0-anisoylaconine was used instead of N-desethyl-8-deoxy-14-0-anisoylaconine. The same operation as in Example 176 was carried out, and N-desethyl-N- (2-methyltetrahydrofurfuryl)-
18 mg of 3,8,13-trideoxy-14-0-anisoylaconine are obtained.

Example 179 The same operation as in Example 128 was carried out to obtain N-desethyl-14-0-anisoylaconine. Instead of N-desethyl-8-deoxy-14-0-anisoylaconine in Example 176, 50 mg of N-desethyl-14-0-anisoylaconine was used,
Otherwise, performing the same operation as in Example 176, N-desethyl-N- (2-methyltetrahydrofurfuryl) -14-
21 mg of 0-anisoylaconine are obtained.

Example 180 The same procedure as in Example 134 was carried out to obtain N-desethyl-3-deoxy-14-0-anisoylaconine. As in Example 176, except that 50 mg of N-desethyl-3-deoxy-14-0-anisoylaconine was used in place of N-desethyl-8-deoxy-14-0-anisoylaconine in Example 176. To obtain 20 mg of N-desethyl-N- (2-methyltetrahydrofurfuryl) -3-deoxy-14-0-anisoylaconine.

Example 181 The same procedure as in Example 140 was carried out except that N-desethyl-3-13-dideoxy-14 was used.
0-Anisoyl aconine is obtained. Instead of N-desethyl-8-deoxy-14-0-anisoylaconine of Example 176, N-desethyl-3,13-dideoxy-
Using the same procedure as in Example 176 except that 50 mg of 14-0-anisoylaconine was used, N-desethyl-N-
22 mg of (2-methyltetrahydrofurfuryl) -3,13-dideoxy-14-0-anisoylaconine are obtained.

Example 182 The same procedure as in Example 66 was repeated, except that N-desethyl-16-epi-8-deoxy-14 was obtained.
-O-Anisoyl aconine is obtained. N- of Example 176
Using N-desethyl-16-epi-8-deoxy-14-0-anisoylaconine instead of desethyl-8-deoxy-14-0-anisoylaconine,
Otherwise by performing the same operations as in Example 176, N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-
Epi-8-deoxy-14-0-anisoylaconine 2
Obtain 3 mg.

Example 183 The same procedure as in Example 146 was carried out to obtain N-desethyl-16-epi-3,8-dideoxy-14-0-anisoylaconine. Example 17
6 in place of N-desethyl-8-deoxy-14-0-anisoylaconine instead of N-desethyl-16-epi-
3,8-dideoxy-14-0-anisoylaconine 5
Using the same procedure as in Example 176, except using 0 mg,
N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-3,8-dideoxy-14-0-
19 mg of anisoyl aconin are obtained.

Example 184 The same procedure as in Example 152 was carried out to obtain N-desethyl-16-epi-3,8,13-trideoxy-14-0-anisoylaconine. Example 176 N-desethyl-8-deoxy-14-0
N-desethyl-16 instead of anisoylaconine
Using the same procedure as in Example 176 except that 50 mg of -epi-3,8,13-trideoxy-14-0-anisoylaconine was used, desethyl-N- (2-methyltetrahydrofurfuryl) -16- 17 mg of epi-3,8,13-trideoxy-14-0-anisoylaconine are obtained.

[Example 185] Jesaconitine 100m
g and 6 mg of imidazole in dry tetrahydrofuran 1
Dissolve in 2 ml, add 210 m
g at 0 ° C. and stir at room temperature. After 30 minutes, 2.4 ml of carbon disulfide and 1.8 ml of methyl iodide were added,
Heat to reflux for 1.5 hours. After cooling, the reaction solution is poured into ice water and extracted three times with 30 ml of chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5
g, ammonia-saturated ether: hexane = 3: 2) to obtain 98 mg of gesaconitine 3,13,15-trithiocarbonate. Next, 30 mg of gesaconitine 3,13,15-trithiocarbonate was dissolved in 1 ml of dry benzene, and a solution of 0.2 ml of tributyltin hydride dissolved in 0.5 ml of dry benzene was added to this solution, and the mixture was heated under reflux for 4 hours. . After cooling, benzene in the reaction solution was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography (5 g, ammonia-saturated ether: hexane = 3: 2) to give 3,13,15-trideoxy. 25 mg of gesaconitine are obtained.

Example 186 Mesaconitine 100 mg
2 ml of pyridine and 8 ml of acetic anhydride are added to the mixture, and the mixture is stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction solution is poured into ice water (30 ml), made alkaline with concentrated aqueous ammonia, and extracted three times with 50 ml of ether. Next, the ether layers are combined, washed twice with 20 ml of water, and the ether is distilled off under reduced pressure. The obtained residue is separated and purified using thin layer chromatography to obtain 3-0-acetylmesaconitine (yield: about 92%). Next, 50 mg of this compound is mixed and dissolved together with pyridine (0.18 ml) and linoleic acid (620 mg), and the mixture is heated and stirred at 70 ° C. for 4 hours. The reaction solution is diluted with ethyl acetate (50 ml), washed with water, dried over sodium sulfate, and then the solvent is distilled off under reduced pressure. The residue was subjected to neutral alumina column chromatography (Al ₂ O ₃ , activity II
I, 10 g, benzene-chloroform = 3: 1) to give 3-0-acetyl-8-0-linoleoyl-14.
Obtain 0-benzoylmesaconin. (75% yield)

Example 187 The procedure of Example 186 was repeated, except that palmitic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 186.
This gives -0-acetyl-8-0-palmitoyl-14-0-benzoylmesaconin. (Yield 73%)

Example 188 The procedure of Example 186 was repeated, except that oleic acid (620 g) was used instead of linoleic acid (620 mg) used in Example 186.
This gives 0-acetyl-8-0-oleoyl-14-0-benzoylmesaconine. (76% yield)

Example 189 The procedure of Example 186 was repeated, except that stearic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 186.
This gives -0-acetyl-8-0-stearoyl-14-0-benzoylmesaconin. (Yield 71%)

Example 190 The procedure of Example 186 was repeated, except that linoleic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 186.
This gives -0-acetyl-8-0-linolenoyl-14-0-benzoylmesaconin. (Yield 73%)

Example 191 The procedure of Example 186 was repeated, except that lauric acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 186.
-Acetyl-8-0-lauroyl-14-0-benzoylmesaconine is obtained. (76% yield)

[Example 192] 2 ml of pyridine and 8 ml of acetic anhydride were added to 100 mg of aconitine, and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction solution was washed with ice water (3.
0 ml), made alkaline with concentrated aqueous ammonia, and extracted three times with 50 ml of ether. Next, the ether layers are combined, washed twice with 20 ml of water, and the ether is distilled off under reduced pressure. The obtained residue is separated and purified using thin-layer chromatography to obtain 3-0-acetylaconitine (yield: about 91%). Next, 50 mg of this compound is mixed and dissolved with pyridine (0.18 ml) and linoleic acid (620 mg), and the mixture is heated and stirred at 70 ° C. for 4 hours. The reaction solution is diluted with ethyl acetate (50 ml), washed with water, dried over sodium sulfate, and then the solvent is distilled off under reduced pressure. The residue was subjected to neutral alumina column chromatography (Al ₂ O ₃ , activity III, 10
g, purified with benzene-chloroform = 3: 1).
0-Acetyl-8-0-linoleoyl-14-0-benzoylaconine is obtained. (Yield 73%)

Example 193 The procedure of Example 192 was repeated, except that palmitic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 192.
This gives -0-acetyl-8-0-palmitoyl-14-benzoylaconine. (Yield 73%)

Example 194 The procedure of Example 192 was repeated, except that oleic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 192.
This gives -0-acetyl-8-0-oleoyl-14-0-benzoylaconine. (Yield 72%)

Example 195 The procedure of Example 192 was repeated, except that stearic acid (620 mg) was used instead of linoleic acid (620 mg) used in Example 192.
This gives -0-acetyl-8-0-stearoyl-14-0-benzoylaconine. (Yield 71%)

Example 196 The procedure of Example 192 was repeated, except that linoleic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 192.
Obtain -0-acetyl-8-0-linolenoyl-14-0-benzoylaconine. (75% yield)

Example 197 The same procedure as in Example 192 was repeated except that lauric acid (620 mg) was used instead of linoleic acid (620 mg) used in Example 192.
This gives -0-acetyl-8-0-lauroyl-14-0-benzoylaconine. (75% yield)

[Example 198] Jesaconitine 100 m
2 ml of pyridine and 8 ml of acetic anhydride are added to g, and the mixture is stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction solution is poured into ice water (30 ml), made alkaline with concentrated aqueous ammonia, and extracted three times with 50 ml of ether. Next, the ether layers are combined, washed twice with 20 ml of water, and the ether is distilled off under reduced pressure. The obtained residue is separated and purified using thin layer chromatography to obtain 3-0-acetylgesaconitine (yield: about 92%). Next, 50 mg of this compound was added to pyridine (0.18 ml) and linoleic acid (620 mg).
The mixture is mixed and dissolved with heating and stirred at 70 ° C. for 4 hours. The reaction solution is diluted with ethyl acetate (50 ml), washed with water, dried over sodium sulfate, and then the solvent is distilled off under reduced pressure. The residue was subjected to neutral alumina column chromatography (Al ₂ O ₃ , activity II
I, 10 g, benzene-chloroform = 3: 1) to give 3-0-acetyl-8-0-linoleoyl-14.
0-Anisoyl aconine is obtained. (Yield 71%)

Example 199 The procedure of Example 198 was repeated, except that palmitic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 198.
This gives -0-acetyl-8-0-palmitoyl-14-0-anisoylaconine. (70% yield)

Example 200 The procedure of Example 198 was repeated, except that oleic acid (620 mg) was used instead of linoleic acid (620 mg) used in Example 198.
This gives -0-acetyl-8-0-oleoyl-14-0-anisoylaconine. (Yield 72%)

Example 201 The procedure of Example 198 was repeated, except that stearic acid (620 mg) was used instead of linoleic acid (620 mg) used in Example 198.
This gives -0-acetyl-8-0-stearoyl-14-0-anisoylaconine. (Yield 72%)

Example 202 The procedure of Example 198 was repeated, except that linolenic acid (620 mg) was used in place of the linoleic acid (620 mg) used in Example 198.
This gives -0-acetyl-8-0-linolenoyl-14-0-anisoylaconine. (70% yield)

Example 203 The procedure of Example 198 was repeated, except that lauric acid (620 mg) was used instead of linoleic acid (620 mg) used in Example 198.
This gives -0-acetyl-8-0-lauroyl-14-0-anisoylaconine. (Yield 73%)

Example 204 Jesaconitine 25 mg
To pyridine (0.09 ml), linoleic acid (300 m
g) and dissolve together, and heat and stir at 70 ° C for 4 hours. The reaction solution was diluted with ethyl acetate (25 ml), washed with water,
Glauber's salt is dried, and the solvent is distilled off under reduced pressure. The residue was subjected to neutral alumina column chromatography (Al ₂ O ₃ , activity III, 10 g, benzene-chloroform = 3: 1).
To obtain 8-0-linoleoyl-14-0-anisoylaconine. (80% yield)

Example 205 The procedure of Example 204 was repeated, except that palmitic acid (300 mg) was used instead of linoleic acid (300 mg) used in Example 204.
This gives -0-palmitoyl-14-0-anisoylaconine. (Yield 82%)

Example 206 The procedure of Example 204 was repeated, except that oleic acid (300 mg) was used instead of linoleic acid (300 mg) used in Example 204.
This gives -0-oleoyl-14-0-anisoylaconine. (78% yield)

Example 207 The procedure of Example 204 was repeated, except that stearic acid (300 mg) was used instead of linoleic acid (300 mg) used in Example 204.
This gives -0-stearoyl-14-0-anisoylaconine. (83% yield)

Example 208 The procedure of Example 204 was repeated, except that linolenic acid (300 mg) was used instead of linoleic acid (300 mg) used in Example 204.
-O-linolenoyl-14-0, anisoylaconine is obtained. (80% yield)

Example 209 The procedure of Example 204 was repeated, except that lauric acid (300 mg) was used instead of linoleic acid (300 mg) used in Example 204.
This gives -0-lauroyl-14-0-anisoylaconine. (Yield 85%)

Example 210 26 mg of mesaconitine was dissolved in 0.5 ml of pyridine, and 0.04 ml of benzoyl chloride was added, followed by heating at 80 ° C. for 30 minutes with stirring. Thereafter, 30 ml of chloroform is added to the reaction solution. The chloroform layer is washed with 5% aqueous ammonia (20 ml) and water (20 ml), dried over calcium chloride and evaporated to dryness under reduced pressure. The residue was separated and purified by thin-layer chromatography (solvent, 28% aqueous ammonia saturated with ether: hexane = 5: 1) to give 3-0-
Benzoyl mesaconitine is obtained (76.9% yield).

Example 211 The procedure of Example 210 was repeated, except that aconitine (25 mg) was used instead of mesaconitine used in Example 210, to obtain 3-0-bensoyl aconitine (yield 81%). .8%).

Example 212 Instead of mesaconitine used in Example 210, gesaconitine (27 m
g) and the other steps were the same as in Example 210, and 3-0
-To obtain benzoylgesaconitine (yield 85.0)
%).

Example 213 22 mg of mesaconitine was dissolved in 0.5 ml of pyridine, and 20 mg of p-anisoyl chloride was added, followed by heating at 80 ° C. for 1 hour with stirring. Thereafter, 30 ml of chloroform is added to the reaction solution. The chloroform layer is washed with 5% aqueous ammonia (20 ml) and water (20 ml), dried over calcium chloride and evaporated to dryness under reduced pressure. The residue was separated and purified by thin-layer chromatography (solvent, 28% aqueous ammonia saturated ether: hexane = 5: 1).
-Anisoyl mesaconitine is obtained (81.8% yield).

Example 214 The procedure of Example 213 was repeated, except that aconitine (25 mg) was used instead of mesaconitine used in Example 213, to obtain 3-0-anisoyl aconitine (yield: 82. 5%).

[Example 215] Instead of the mesaconitine used in Example 213, gesaconitine (27 m
g) and the other steps were the same as in Example 213, and 3-0
-Anisoyl gesaconitine is obtained (79% yield).

Example 216 Aconitine (180 mg) was dissolved in methanol (30 ml), and the mixture was stirred at an oil bath temperature of 60 to 70 ° C. for 30 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to give 8-0.
-Methyl-14-0-benzoylaconine 127.6m
g (72% yield).

[Example 217] Aconitine (103 mg) was dissolved in ethanol (10 ml), and the mixture was stirred at an oil bath temperature of 70 to 80 ° C for 64 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to give 8-0.
-Ethyl-14-0 benzoyl aconine 71.6 mg
(71% yield).

Example 218 8 ml of pyridine and 30 ml of acetic anhydride were added to 331 mg of aconitine, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform (50 ml).
After washing with an aqueous solution of HCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to obtain 300.9 mg of 3-0-acetylaconitine (85.3% yield). 3-0-acetylaconitine 10
0.5 mg was dissolved in 10 ml of methanol, and the oil bath temperature was 7
Stir at 0-80 ° C for 87 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia in ether) to give 3-0-acetyl-8-0-methyl-14-0-benzoyl alcohol. 75 mg of nin (73% yield) are obtained.

[Example 219] Instead of methanol (10 ml) used in Example 218, ethanol (1 ml) was used.
The same procedure as in Example 218 was carried out except for using 0 ml.
71 mg (72% yield) of 0-acetyl-8-0-ethyl-14-0-benzoylaconine are obtained.

Example 220 To 331 mg of aconitine, 8 ml of pyridine and 30 ml of acetic anhydride were added, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform (50 ml).
After washing with an aqueous solution of HCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia) to obtain 300.9 mg of 3-0-acetylaconitine (yield: 85.3%).
The mixture was heated under reflux for 4 hours in 10 ml of a mixture of dioxane and water (1: 1). After completion of the reaction, the solvent is distilled off under reduced pressure.
The obtained residue is separated and purified by column chromatography or thin-layer chromatography (solvent: saturated aqueous ammonia in ether) to obtain 78 mg (83% yield) of 3-0-acetyl-14-0-benzoylaconine.

Example 221 Mesaconitine 300 mg
Was dissolved in 180 ml of methanol, and the oil bath temperature was 60-70.
Stir for 168 hours at ° C. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether).
-0-methyl-14-0-benzoylmesaconin 280
mg (97.6% yield).

Example 222 Mesaconitine 300 mg
Was dissolved in 18 oml of ethanol, and the oil bath temperature was 60-70.
Stir at 240C for 240 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether).
-0-ethyl-14-0-benzoylmesaconine 285
mg (97% yield).

Example 223 Mesaconitine 408 mg
8 ml of pyridine and 30 ml of acetic anhydride were added to the mixture at room temperature.
Stir for hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform (50 ml).
After washing with an aqueous solution of aHCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to obtain 400.6 mg of 3-0-acetylmesaconitine. (Yield 95%). 131.0 mg of 3-0-acetylmesaconitine is dissolved in 10 ml of methanol, and the mixture is stirred at an oil bath temperature of 70-80 ° C for 39 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to obtain 3-0-acetyl-8-0-methyl-14.
87.9 mg of-0-benzoylmesaconin (yield 70
%).

Example 224 Mesaconitine 408 mg
8 ml of pyridine and 30 ml of acetic anhydride were added to the mixture at room temperature.
Stir for hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in 50 ml of chloroform.
After washing with an aqueous solution of aHCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia) to obtain 400.6 mg of 3-0-acetylmesaconitine. (Yield 95%). 136.0 mg of 3-0-acetylmesaconitine is dissolved in 10 ml of ethanol and stirred at an oil bath temperature of 70-80 ° C for 87 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia ether) to give 3-0-acetyl-8-0-ethyl-14.
98.2 mg of 0-benzoylmesaconine (74% yield)
Get.

Example 225 Mesaconitine 408 mg
8 ml of pyridine and 30 ml of acetic anhydride were added to the mixture at room temperature.
Stir for hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in 50 ml of chloroform.
After washing with an aqueous solution of aHCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia) to obtain 400.6 mg of 3-0-acetylmesaconitine. (Yield 95%). 100 mg of 3-0-acetylmesaconitine is heated under reflux for 4 hours in 10 ml of a dioxane-water (1: 1) mixture. After completion of the reaction, the solvent is distilled off under reduced pressure. The obtained residue is subjected to column chromatography or thin-layer chromatography (solvent: aqueous ammonia saturated ether).
To obtain 37.8 mg (83% yield) of 3-0-acetyl-14-0-benzoylmesaconine.

[Example 226] Jesaconitine 100 m
g in 30 ml of methanol.
Stir at 72 ° C. for 72 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether).
-0-methyl-14-0-anisoyl aconine 84.5
mg (81% yield).

[Example 227] Jesaconitine 100m
g was dissolved in 30 ml of ethanol, and the oil bath temperature was 60-70.
Stir at 120 ° C. for 120 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether).
-0-ethyl-14-0-anisoyl aconine 73.5
mg (72% yield).

Example 228 Jesaconitin 404
To the mg, 8 ml of pyridine and 30 ml of acetic anhydride are added, and the mixture is stirred at room temperature for 16 hours. The reaction solution was concentrated to dryness under reduced pressure, the residue was dissolved in 50 ml of chloroform, and the chloroform layer was concentrated in 5 ml.
% NaHCO ₃ aqueous solution, then washed with water, dried over sodium sulfate and distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia in ether) to give 3-0-acetylgesaconitine 411.
7 mg are obtained (95.8% yield). Dissolve 3-0 mg of 3-0-acetylgesaconitine in 10 ml of methanol and stir at an oil bath temperature of 60-70 ° C for 44 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia in ether), and purified 3-0-acetyl-8-0-methyl-14-0-anisoyl alcohol. 72.3 mg of nin (yield 7
3%).

[Example 229] Jesaconitine 404m
g of pyridine and 8 ml of acetic anhydride.
Stir for 6 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform (50 ml).
NaHCO ₃ aqueous solution, then washed with water, dried over sodium sulfate,
Evaporate under reduced pressure. The residue was separated by silica gel column chromatography (solvent: aqueous ammonia saturated ether),
Purified, 3-0-acetyl gesaconitine 411.7m
g (95.8% yield). 114.9 mg of 3-0-acetylgesaconitine is dissolved in 10 ml of ethanol, and the mixture is stirred at an oil bath temperature of 60 to 70 ° C for 114 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia) to give 3-0-acetyl-8-0-ethyl-14-0-anisoyl. 80.5 mg of aconine (yield 7
2%).

[Example 230] Jesaconitine 404m
g of pyridine and 8 ml of acetic anhydride.
Stir for 6 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform (50 ml).
NaHCO ₃ aqueous solution, then washed with water, dried over sodium sulfate,
Evaporate under reduced pressure. The residue was separated by silica gel column chromatography (solvent: aqueous ammonia saturated ether),
Purified, 3-0-acetyl gesaconitine 411.7m
g (95.8% yield). 100 mg of 3-0-acetylgesaconitine in dioxane-water (1: 1) mixture 1
Heat to reflux in 0 ml for 4 hours. After completion of the reaction, the solvent is distilled off under reduced pressure. The obtained residue was separated and purified by column chromatography or thin-layer chromatography (solvent: aqueous ammonia saturated ether) to give 3-0-acetyl-14-0-.
79.9 mg (85% yield) of anisoyl aconin are obtained.

Example 231 Hypaconitine (55 mg) was dissolved in methanol (5 ml).
Stir for 2 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure,
The residue was subjected to silica gel column chromatography (solvent:
Separation and purification with aqueous ammonia saturated ether: hexane = 4: 1) to obtain 35.8 mg (yield: 75%) of 8-0 methyl-14-0-benzoylhypaconin.

[Example 232] 55 mg of hypoconitine was dissolved in 10 ml of nitranol, and the mixture was stirred at an oil bath temperature of 70 to 80 ° C for 72 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether: hexane = 4: 1) to give 8-0 ethyl-14-0-benzoylhypaco. 35.2 mg (68% yield) of nin are obtained.

Example 233 Aconitine (100 mg) was dissolved in amyl alcohol (30 ml) and the oil bath temperature was adjusted to 60 to 7
Stir at 0 ° C. for 240 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: saturated aqueous ammonia with ether) to give 8-0-amyl-14-0-benzoylaconine.
3 mg (71% yield) are obtained.

Example 234 8 ml of pyridine and 30 ml of acetic anhydride were added to 331 mg of aconitine, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in 50 ml of chloroform.
After washing with an aqueous solution of HCO _{3 and} then with water, it is dried over sodium sulfate and evaporated under reduced pressure. The residue is separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to obtain 300.9 mg of 3-0-acetylaconitine (85.3% yield). 3-0-acetylaconitine 10
Dissolve 0 mg in 10 ml of amyl alcohol and stir at an oil bath temperature of 70-80 ° C for 240 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (solvent: aqueous ammonia saturated ether) to give 3-0-acetyl-8-0-amyl-14.
78.3 mg of 0-benzoyl aconine are obtained (yield 73%).

Example 235 8-0-Amyl-14-0-benzoyl mesacoine was prepared in the same manner as in Example 233 except that aconitine (100 mg) used in Example 233 was replaced with mesaconitine (100 mg). 76.2 mg (73% yield) of nin are obtained.

[Example 236] Mesaconitine (408 mg) was used in place of aconitine (331 mg) used in Example 234, and the other steps were carried out in the same manner as in Example 234, except that 3-0-acetyl-8-0-amyl- was used. 75.0 mg (72% yield) of 14-0-benzoylmesaconin are obtained.

[Example 237] 8-0-Amyl-14-0-anisoyl was prepared in the same manner as in Example 233 except that gesaconitine (100 mg) was used in place of aconitine (100 mg) used in Example 233. 78.3 mg of aconine (75% yield) are obtained.

Example 238 Jesaconitine (404 mg) was used in place of aconitine (331 mg) used in Example 234, and the other steps were carried out in the same manner as in Example 234, except that 3-0-acetyl-8-0-amyl- was used. 14-0-
74.0 mg (71% yield) of anisoyl aconin are obtained.

Example 239 The same procedure as in Example 233 was repeated except that hypoconitine (100 mg) was used in place of aconitine (100 mg) used in Example 233. 73.2 mg of paconin (70% yield) are obtained.

Example 240 100 g of methanol was added to 5 g of raw abalone, and the mixture was refluxed for about 100 hours. Then, the extract is filtered, and the filtrate is distilled off under reduced pressure. The residue obtained is dissolved in 50 ml of a 5% aqueous hydrochloric acid solution and partitioned with 80 ml of hexane. Next, p is added to this 5% hydrochloric acid aqueous solution.
10% aqueous ammonia is added until H is about 9, and the aqueous layer is extracted three times with 100 ml of chloroform. The chloroform layer is dried over sodium sulfate and distilled off under reduced pressure to obtain about 80 mg of a residue. This residue is dissolved in 10 ml of acetonitrile to obtain a sample solution. For 10 μl of this sample solution, high performance liquid chromatography (HPLC) under the following conditions:
80-methyl-14-0-benzoyl aconine, 8-0
-Methyl-14-0-benzoylmesaconine, 8-0-
Methyl-14-0-anisoylaconine, and 8-0
-Methyl-14-0-benzoylhypaconin can be analyzed and collected. (HPLC analysis conditions) Mobile phase: 0.05 M phosphate buffer (pH 2.5): tetrahydrofuran: acetonitrile (80: 14: 6) Flow rate: 1.0 ml / min Detection wavelength: 247 nm Column: Chemcosorb ODS-H (4 .6x
(150 mm) (HPLC preparative conditions) Mobile phase: methanol: water: chloroform: triethylamine (80: 20: 2: 0.1) Flow rate: 10 ml / min Detection wavelength: 247 nm Column: Inertosyl ODS (22.5 × 250 mm)

Example 241 The procedure of Example 240 was repeated, except that ethanol (100 ml) was used in place of methanol (100 ml) used in Example 240, except that 8-0-ethyl-14-0-benzoylaconine was used. , 8
-0-ethyl-14-0-benzoylmesaconine, 8-
0-ethyl-14-0-anisoylaconine and 8-
0-ethyl-14-0-benzoylhypaconin can be analyzed and fractionated.

[Example 242] Aconitine 80 mg
A 0 ml Meyer wall is uniformly deposited and heated at 200 ° C. for 30 minutes under reduced pressure (1-1.5 mmHg). After cooling, it was dissolved in chloroform, and p-TLC (pre
Separation by (parametric TLC) (ammonia saturated chloroform / ammonia saturated ether = 1: 1)
Purification yields 15 mg of 16-epi-pyroaconitine and 12 mg of pyroaconitine.

Example 243 The procedure of Example 242 was repeated, except that 100 mg of mesaconitine was used instead of aconitine. The procedure of Example 242 was repeated to obtain 25 mg of 16-epi-pyrromesaconitine and 20 mg of pyromesaconitine.

Example 244 The procedure of Example 242 was repeated, except that 200 mg of hyaconitine was used instead of aconitine, to obtain 28 mg of 16-epi-pyrohypaconitine and 19 mg of pyrohypaconitine.

Example 245 The procedure of Example 242 was repeated, except that 100 mg of gesaconitine was used instead of aconitine, to obtain 28 mg of 16-epi-pyrodiesaconitine and 25 mg of pyrojesaconitine.

[Example 246] 500 g of a sticky cake was subjected to pressurization and heat treatment in an autoclave at 110 ° C for 40 minutes, dried, pulverized, and extracted five times with methanol 11. The methanol extract is evaporated to dryness, dissolved in 300 ml of 5% hydrochloric acid, and washed once with 200 ml of hexane. The hydrochloric acid layer is adjusted to pH 9 with aqueous ammonia, and 300 ml of chloroform is added.
Extract three times. The chloroform layer was concentrated to dryness under reduced pressure, and then separated and purified repeatedly using silica gel column chromatography (chloroform, 5% methanol / chloroform system).
6-epi-pyroaconitine, pyroaconitine, 16-epi-pyrromesaconitine, pyromesaconitine, 16-epi-pyrohypaconitine, pyrohypaconitine, 16-epi-
Pyrogessaconitine and pyroguesaconitine can be obtained. In addition, these compounds were separated using a liquid chromatography method under the following conditions to collect a crude fraction of the above compound,
It can also be obtained by separation and purification by silica gel column chromatography. Conditions for liquid chromatography method Column: Inertosyl ODS (20 × 250 mm) Mobile phase: 0.05 M phosphorous salt buffer (pH 2.35)
Tetrahydrofuran acetonitrile (80:15:
5) Flow rate: 10 ml / min.

Example 247 Aconitine (100 mg) was refluxed for 4 hours in 20 ml of a mixture of dioxane / water (1: 1). After completion of the reaction, the solvent is distilled off under reduced pressure. The residue was subjected to thin-layer chromatography (eluent: 3% methanol / ammonia-saturated chloroform), separated and purified to obtain 14-0-benzoylaconine (75 mg).

Example 248 The procedure of Example 247 was repeated, except that 100 mg of mesaconitine was used instead of aconitine, to obtain 73 mg of 14-0-benzoylmesaconin.

Example 249 The procedure of Example 247 was repeated, except that 100 mg of hypoconitine was used instead of aconitine, to obtain 70 mg of 14-0-benzoylhypaconin.

Example 250 The procedure of Example 247 was repeated except that 100 mg of gesaconitine was used instead of aconitine to obtain 74 mg of 14-0-anisoylaconine.

[Example 251] 4 kg of fresh carrots were extracted by heating and refluxing three times with methanol 41 for 30 minutes. The extract is concentrated to dryness, suspended in 0.5 ml of 0.1N hydrochloric acid, and washed twice with chloroform 11. The aqueous layer is adjusted to about pH 14 with aqueous ammonia, and extracted three times with 1.5 l of chloroform. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to alumina column chromatography and eluted with chloroform. The eluate was concentrated to dryness under reduced pressure, and the residue was subjected to silica gel column chromatography, washed with chloroform, and 5% methanol /
Elute with chloroform and 7.5% methanol / chloroform. After the eluate was concentrated and dried under reduced pressure, the residue was subjected to Sephadex G-15 column chromatography, and eluted with water. The eluate was concentrated and dried under reduced pressure.
Recrystallization from ethanol gives 100 mg of neolin.

Example 252 40 mg of neolin was added to 0.2 ml of trifluoroacetic acid and 21.7 m of benzoyl chloride.
g, and stirred at 80 ° C. for 6 hours. The reaction solution is poured into water, made alkaline with 10% aqueous ammonia, and extracted with chloroform. After the extract was concentrated and dried under reduced pressure, the residue was subjected to silica gel column chromatography (separation liquid: 5% methanol / ammonia saturated chloroform), separated and purified to obtain 11 mg of 14-0-benzoylneoline.

Example 253 The procedure of Example 252 was repeated, except that 9 ml of acetic acid was used instead of 21.7 mg of benzoyl chloride, to obtain 10 mg of 14-0-acetylneoline.

[Example 254] 70 mg of mesaconitine was dissolved in 5 ml of methanol, and 1 ml of 5% potassium hydroxide was dissolved.
And heat to reflux for 3 hours. After methanol in the reaction solution was distilled off under reduced pressure, 5 ml of water was added, and methylene chloride was added.
Extract three times with ml. The extract is dried over sodium sulfate and concentrated to dryness under reduced pressure. Thin layer chromatography of the residue (eluent: 10% methanol / ammonia saturated chloroform)
Then, separation and purification are performed to obtain 30 mg of mesaconin.
Mesaconin 3 in place of 30 mg of aconin of Example 90
Using the same procedure as in Example 90 except that 0 mg was used and 30 mg of p-chlorobenzoyl chloride was used instead of 30 mg of m-chlorobenzoyl chloride, 20 mg of 14-0-p-chlorobenzoylmesaconin was obtained.

Example 255 The procedure of Example 90 was repeated, except that 30 mg of p-chlorobenzoyl chloride was used instead of 30 mg of m-chlorobenzoyl chloride. Nin 21mg
Get.

Example 256 14-0-p-Fluorobenzoyl alcohol was prepared in the same manner as in Example 90 except that 30 mg of p-fluorobenzoyl chloride was used in place of 30 mg of m-chlorobenzoyl chloride in Example 90. Nin 19m
g.

Example 257 The procedure of Example 90 was repeated, except that 30 mg of p-bromobenzoyl chloride was used instead of 30 mg of m-chlorobenzoyl chloride. Nin 20mg
Get.

Example 258 The same procedure as in Example 88 was carried out to obtain 70 mg of aconine. Aconine (70 mg) is dissolved in pyridine (1.2 ml), p-chlorobenzoyl chloride (0.09 ml) is added at −18 ° C., and the mixture is stirred for 10 minutes.
The reaction mixture is subjected to silica gel column chromatography (30
g), chloroform (30 ml), 5% methanol / chloroform (30 ml), 10% methanol / chloroform (30 ml), 15% methanol / chloroform (30 ml), 20% methanol / chloroform (3 ml)
0 ml). The eluates of 10% methanol / chloroform and 15% methanol / chloroform are combined and concentrated to dryness under reduced pressure. The residue was dissolved in 3 ml of ammonia-saturated chloroform, and separated by silica gel column chromatography (30 g) (separated liquid: ammonia-saturated chloroform) to obtain 32 mg of 3,14-di-p-chlorobenzoylaconine.

Example 259 The same procedure as in Example 90 was repeated, except that 30 mg of p-chlorobenzoyl chloride was used instead of 30 mg of m-chlorobenzoyl chloride in Example 90. 21 mg are obtained. 21 mg of 14-p-chlorobenzoyl aconine was dissolved in 3 ml of acetone, and 1 ml of an aqueous solution of potassium permanganate (887 mg / 25 ml of water) and 0.2 ml of an aqueous solution of potassium carbonate (556 mg / 4.5 ml of water) were added to this solution.
and stirred at room temperature for 30 minutes. After the completion of the reaction, the reaction solution was concentrated under reduced pressure until the smell of acetone disappeared, and 1.3 ml of 2N sulfuric acid and 1.3 ml of an aqueous sodium thiosulfate solution (887 mg / 22 ml of water) previously cooled to a residual solution were added.
Add 1 and wash with methylene chloride. The aqueous layer is adjusted to pH 8-9 with sodium carbonate and extracted with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5
% Methanol / ammonia saturated chloroform)
Separated and purified, N-desethyl-8-deoxy-14-0
-15 mg of anisoyl aconin are obtained.

Example 260 8 mg of neoline was dissolved in 1 ml of pyridine, and 0.2 ml of acetic anhydride was added thereto.
Leave at room temperature for 30 minutes. 20 ml of water and 10 ml of 1N sodium carbonate were added to the reaction solution, and ether 30 m
Extract three times with l. After the extract was concentrated to dryness, the residue was subjected to silica gel column chromatography (7 g), and a chloroform / methanol mixed solution (99.5: 0.
5) After washing with 30 ml, elute with 30 ml of a chloroform / methanol mixture (98: 2) and concentrate the eluate to dryness to obtain 8 mg of 1,14-diacetylneoline.

Example 261 4 mg of neoline was dissolved in 1 ml of pyridine, 18 mg of benzoyl chloride was added, and the mixture was allowed to stand at room temperature for 15 minutes. 20 m of water in the reaction solution
1 and 10 ml of 1N sodium carbonate are added, and the mixture is extracted three times with 30 ml of ether. After concentrating the extract to dryness,
The residue was subjected to silica gel column chromatography (7 g).
And a chloroform / methanol mixture (99.5:
0.5) After washing with 30 ml, elution was carried out with 30 ml of a chloroform / methanol mixed solution (98: 2), and the eluate was concentrated to dryness, and 4.5 ml of 1,14-dibenzoylneoline.
g.

Example 262 The same procedure as in Example 88 was carried out to obtain 70 mg of aconine. Dissolve 30 mg of aconine in 1 ml of pyridine and add 3-chloropropionyl chloride 1
Add 8 mg and stir at 80 ° C. for 4 hours. After the reaction,
Pyridine is distilled off under reduced pressure, water is added to the residue, the mixture is made alkaline with a 5% aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified to obtain 18 mg of 14-0- (3-chloropropionyl) aconine.

Example 263 The same procedure as in Example 88 was carried out to obtain 70 mg of aconine. 30 mg of aconine is dissolved in 3.6 ml of 1,2-dimethoxyethane, 90 mg of sodium hydride is added, and the mixture is stirred at room temperature for 30 minutes. 0.7 m of 4-chloro-1-butanol was added to the reaction solution.
and heat to reflux for 30 minutes. After the completion of the reaction, the reaction solution is poured into ice water and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 14-0-
17 mg of (4-hydroxybutyl) aconine are obtained.

Example 264 In place of 4-chloro-1-butanol of Example 263, 1 ml of 4-bromo-1-methylcyclohexane (mixture of cis- and trans-forms) was used.
And operating the same as in Example 263 except for using 14-0-
19 mg of (4-methyl-cyclohexyl) aconine are obtained.

[Example 265] 660 mg of 14-0-benzoyl aconine was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / water 25) was added to this solution.
ml) and an aqueous potassium carbonate solution (556 mg /
(4.5 ml of water) and add 4.5 ml and stir at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure until the smell of acetone disappeared, and 2N previously cooled to a residual liquid.
33 ml of sulfuric acid and sodium thiosulfate aqueous solution (887 m
g / water 22 ml) and wash with methylene chloride. Adjust the aqueous layer to pH 8-9 with sodium carbonate,
Extract with methylene chloride. The methylene chloride layer is dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform), separated and purified to obtain 610 mg of N-desethyl-14-0-benzoylaconine. N
-Desethyl-14-0-benzoylaconine 50mg
Is dissolved in 1 ml of methanol, 50 mg of potassium carbonate,
0.1 ml of water and 50 mg of p-anisoyl chloride are added,
Stir at room temperature for 1 hour. After completion of the reaction, the reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in 20 ml of chloroform.
The chloroform layer is washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify, and N-desethyl-N- (p
-Anisoyl) -14-0-benzoylaconine 30 m
g.

Example 266 The p-chloride of Example 265
3-chloropropionyl chloride instead of anisoyl
Using the same procedure as in Example 265, except using 03 ml, N
-Desethyl-N- (3-chloropropionyl) -14
27 mg of -0-benzoylaconine are obtained.

Example 267 n-Amyl iodide was prepared by substituting 50 mg of N-desethyl-14-0-benzoylaconine for N-desethyl-8-deoxy-14-0-anisoylaconine in Example 51. And using the same procedure as in Example 51 except for using 0.6 ml of crotyl chloride, to obtain 29 mg of N-desethyl-N-crotyl-14-0-benzoylaconine.

Example 268 The procedure of Example 51 was repeated, except that 50 mg of N-desethyl-14-0-benzoylaconine was used in place of N-desethyl-8-deoxy-14-0-anisoylaconine. Instead of amyl, 0.9 ml of 4-bromo-1-methylcyclohexane (mixture of cis-form and trans-form) was used, and the other operations were carried out as in Example 51, except that N-desethyl-N- (4-methyl-cyclohexyl) ) -14-0-Benzoylaconine 26 mg are obtained.

Example 269 The procedure of Example 51 was repeated, except that 50 mg of N-desethyl-14-0-benzoylaconine was used instead of N-desethyl-8-deoxy-14-0-anisoylaconine. 0.6 ml of 4-chloro-1-butanol was used instead of amyl.
The same operation as in 1 was performed to obtain 25 mg of N-desethyl-N- (4-hydroxybutyl) -14-0-benzoylaconine.

(1) Physical properties and analytical data of 8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate It is soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.91) (H of anisoyl group) 6.93 (2H, d, J = 8.91) (same as above) 4.43 (1H, d, J = 4. 95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.11 (3H, t, J = 6.93) (N -H) of methyl group of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of carbonyl of anisoyl group) 163.6,131.8,122.2,113.7
(C of anisoyl group) 94.3, 85.2, 83.7, 80.2, 77.4
75.1, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.9,56.1 (16,1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 55.4 (C of the methoxy group of the anisoyl group) 49.1 (C of the methylene of the N-ethyl group) 13.4 (Methyl of the N-ethyl group) C) 6) Mass spectrum analysis m / Z 617 (M ⁺ )

(2) 3,13-dideoxy-14-O-
Physical properties and analytical data of anisoyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis 3450, 1715 cm ^-1 shows maximum absorption 3) Ultraviolet absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.96 (2H, d, J = 8.0) (H of anisoyl group) 6.92 (2H, d) 5.03 (1H, d, J = 4.55) (βH at position 14) 3.86 (3H, s) (H of methoxy group of anisoyl group) 60 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.17 (3H) , S) (same as above) 1.09 (3H, t, J = 6.97) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. (Δ, ppm). 166.0 (C of carbonyl of anisoyl group) 163.4,131.9,122.1,113.6
(C of anisoyl group) 89.5, 85.1, 83.6, 82.0, 80.0,
79.7, 78.6, (16, 1, 6, 15, 18, 1
4,8th C) 59.1,58.1,57.9,56.1 (18,1
6,5.4, C of the methoxy group bonded to the 1 position) 55.4 (C of the methoxy group of the anisoyl group) 48.5 (C of the methylene of the N-ethyl group) 13.4 (C of the methylene of the N-ethyl group) C) 6) Mass spectrum analysis m / Z597 (M ⁺ )

(3) 3,8,13-Trideoxy-14
-O-Anisoyl aconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 5.01 (1H, t, J = 4. 53) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.60 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 1.10 (3H, t, J = 6.95) (N -H of methyl group of ethyl group) 5) 13C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.5, 131.6, 122.1, 113.8 (C of anisoyl group) 93.2, 85.1, 84.6, 80.1, 79. 9,
72.0 (C at positions 16,1,6,18,14,15) 59.1,58.3,58.0,56.1 (16,1
55.3 (C of the methoxy group of the anisoyl group) 49.1 (C of the methylene group of the N-ethyl group) 13.4 (C of the methylene group of the N-ethyl group) C) 6) Mass spectrum analysis m / z 585 (M ⁺ )

(4) Physical property values and analytical data of 3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.91) (H of anisoyl group) 6.92 (2H, d, J = 8.91) (same as above) 4.45 (1H, d, J = 4.91) 95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.18 (3H, s) (same as above) 1.10 (3H, t, J = 6.95) (N -H) of methyl group of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.5,131.7,122.2,113.8 (C of anisoyl group) 94.4,85.3,84.3,80.2,80. 0,
75.0, 72.5, (16, 1, 6, 18, 14, 1
C at 3 and 15) 61.8, 59.1, 57.9, 56.1 (16, 1
C, the methoxy group bonded to the 8, 6, 1-position) 55.4 (C, the methoxy group of the anisoyl group) 49.1 (C, the methylene of the N-ethyl group) 13.4 (the methyl of the N-ethyl group) C) 6) Mass spectrum analysis m / z 601 (M ⁺ )

(5) Physical property values and analytical data of 3-deoxygesaconitine 1) Properties and solubility Colorless crystals having a melting point of 175 to 176 ° C, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethylsulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.97 (2H, d, J = 8.0) (H of anisoyl group) 6.92 (2H, d, J = 8.0) (same as above) 4.83 (1H, d, J = 5. 0) (βH at position 14) 3.88 (3H, s) (H of the methoxy group of the anisoyl group) 3.74 (3H, s) (H of the methoxy group at the 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.17 (3H, s) (same as above) 1.43 (3H, s) (methyl group of acetyl group at 8-position) H) 1.08 (3H, t, J = 7.0) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) ). 172.4 (C of carbonyl of acetyl group) 165.8 (C of carbonyl of anisoyl group) 163.4, 131.6, 122.3, 113.8
(C of anisoyl group) 92.1, 90.2, 85.2, 83.3, 80.3,
78.8, 78.7, 74.2 (8, 16, 1, 6, 1
8, 15, 14, 13th C) 61.1, 59.1, 58.0, 56.2 (16, 1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 55.5 (C of the methoxy group of the anisoyl group) 49.1 (C of the methylene of the N-ethyl group) 13.4 (Methyl of the N-ethyl group) C) 21.5 (methyl C of acetyl group) 6) Mass spectrum analysis m / z 657 (M ⁺ )

(6) Physical properties and analytical data of 3,13-dideoxygesaconitine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.97 (2H, d, J = 8.0) (H of anisoyl group) 6.92 (2H, d, J = 8.0) (same as above) 5.04 (1H, t, J = 4. 52) (βH at position 14) 3.87 (3H, s) (H of the methoxy group of the anisoyl group) 3.60 (3H, s) (H of the methoxy group at the 1,6, 16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.17 (3H, s) (same as above) 1.43 (3H, s) (methyl group of acetyl group at 8-position) H) 1.07 (3H, t, J = 7.0) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) ). 172.4 (C of carbonyl at the 8-position acetyl group) o (carbonyl C of anisoyl group) 163.5, 131.5, 122.2, 113.8 (C of anisoyl group) 92.0, 89.3, 85.1, 83.6, 80.1,
76.3, 75.4, (8, 16, 1, 6, 18, 1
C at 4, 15th position) 59.1, 58.2, 58.0, 56.0 (18, 1
65.4, C of the methoxy group bonded to the 1 position) 55.4 (C of the methoxy group of the anisoyl group) 49.0 (C of the methylene of the N-ethyl group) 13.4 (C of the methylene of the N-ethyl group) C) 21.5 (C of methyl of acetyl group) 6) Mass spectrum analysis m / z 641 (M ⁺ )

(7) Physical property value and analysis data of 3-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate , Soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis Shows absorption maximum at 3450, 1710 cm ^-1 3) Ultraviolet absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, d, J = 8.9) (H of anisoyl group) 6.89 (2H, d, J = 8.9) (same as above) 4.97 (1H, d, J = 5. 27) (βH at position 14) 3.85 (3H, s) (H of methoxy group of anisoyl group) 3.70 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.17 (3H, s) (same as above) 1.08 (3H, t, J = 7.0) (N -H) of methyl group of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of the carbonyl of anisoyl group) 163.5, 131.8, 122.1, 113.6 (C of the anisoyl group) 90.7, 85.3, 83.3, 81.9, 80. 2,
79.5, 78.7, 74.8 (16, 1, 6, 15,
18, 14, 8, 13th position C) 60.9, 59.1, 58.0, 56.2 (16, 1
C, the methoxy group bonded to the 8,6,1-position) 55.4 (C, the methoxy group of the anisoyl group) 48.4 (C, the methylene of the N-ethyl group) 13.4 (the methyl of the N-ethyl group) C) 6) Mass spectrum analysis m / z 613 (M ⁺ )

(8) Physical property values and analytical data of 3-deoxy-14-O-benzoylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.18 (5H, m) (H of benzoyl group) 4.85 (1H, d, J = 4.50) (βH at position 14) 3.71 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.24 (6H, s) (same as above) 3.14 (3H, s) (same as above) 1.08 (3H, t, J = 7.02) (same as above) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl group of N-ethyl group The following signals are shown (δ, ppm). 165.9 (C of carbonyl of benzoyl group) 133.1, 129.9, 129.5, 128.5 (C of benzoyl group) 90.6, 85.4, 83.2, 81.6, 80. 2,
79.4, 78.7, 74.0 (16, 1, 6, 15,
C, 18,14,8,13) 60.9,59.1,57.8,56.0 (16,1
8,6,1-position bonded methoxy group C), 49.0 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) Mass spectrum analysis m / z 587 (M ⁺ )

(9) 3,13-dideoxy-14-O-
Benzoyl aconine properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water is there. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.38-8.14 (5H, m) (H of benzoyl group) 5.04 (1H, t, J) = 4.50) (βH at position 14) 3.52 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 3.28 (3H, s) (as above) 3.26 ( 3H, s) (same as above) 3.17 (3H, s) (same as above) 1.07 (3H, t, J = 7.0) (H of methyl group of N-ethyl group) 5) ¹³ C nucleus Magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 166.0 (C of benzoyl group carbonyl) 133.1, 130.0, 129.5, 128.5 (C of benzoyl group) 89.3, 85.3, 83.2, 81.8, 80.3,
79.3, 78.5 (16, 1, 6, 15, 18, 1
4,8, C) 59.0,57.9,57.6,56.0 (18,1
C, derived from a methoxy group bonded to the 6,6,1 position) 49.1 (C of N-ethyl group of methylene) 13.4 (C of N-ethyl group of methyl) 6) Mass spectrum analysis m / z 571 (M ⁺ )

(10) Physical property values and analytical data of 8-deoxy-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40.8.12 (5H, m) (H of benzoyl group) 4.47 (1H, d, J = 4.97) (βH at position 14) 3.68 (3H, s) (1, 6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.07 (3H, t, J = 7.0) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of carbonyl of benzoyl group) 133.2, 130.0, 129.6, 128.6 (C of benzoyl group) 94.2, 85.2, 83.7, 80.1, 77. 5,
75.2, 72.4, 71.9 (16, 6, 1, 1
4,18,13,15,3rd position C) 60.9,59.0,57.9,56.1 (16,1
Methoxy group C bonded to the 8,6,1 position 49.0 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) mass spectrometry m / z 587 ( M ⁺ )

(11) 3,8-dideoxy-14-O-
Physical property values and analytical data of benzoyl aconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.15 (5H, m) (H of benzoyl group) 4.48 (1H, d, J = 4,98) (βH at position 14) 3.72 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.29 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.08 (3H, t, J = 6.98) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of carbonyl of benzoyl group) 133.1, 130.0, 129.6, 128.6 (C of benzoyl group) 94.2, 85.2, 84.3, 80.2, 80. 0,
72.5 (C at positions 16, 16, 6, 18, 14, 15) 60.9, 59.0, 57.9, 56.1 (16, 1
C, the methoxy group bonded to the 8,6,1 position 49.0 (C of the methylene of the N-ethyl group) 13.5 (C of the methyl of the N-ethyl group) 6) Mass spectrum analysis m / z 571 ( M ⁺ )

(12) 3,8,13-Trideoxy-1
Physical properties and analytical data of 4-O-benzoylaconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.38-8.15 (5H, m) (H of benzoyl group) 5.02 (1H, t, J = 4.49) (βH at position 14) 3.52 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.07 (3H, t, J = 6.98) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl of benzoyl group) 133.1, 130.0, 129.7, 128.6 (C of benzoyl group) 93.2, 85.2, 84.5, 80.2, 79. 9,
72.0 (C at positions 16,1,6,18,14,15) 59.2,57.9,57.6,56.0 (18,1
6,6,1 bonded to C-position of methoxy group 49.1 (N-ethyl group of methylene C) 13.4 (N-ethyl group of methyl C) 6) mass spectrometry m / z 555 ( M ⁺ )

(13) Physical property values and analytical data of 3-deoxyaconitine 1) Properties and solubility Colorless crystals having a melting point of 178 to 180 ° C, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide Soluble in water, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.18 (5H, m) (H of benzoyl group) 4.86 (1H, d, J = 4.50) (βH at position 14) 3.72 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.24 (6H, s) (same as above) 3.14 (3H, s) (same as above) 1.36 (3H, s) (methyl at the 8-position acetyl group) H) 1.06 (3H, t, J = 7.0) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 172.2 (C of carbonyl of acetyl group at position 8) 165.9 (C of carbonyl of benzoyl group) 133.1, 129.9, 129.5, 128.5 (C of benzoyl group) 92.0, 90 .2, 85.2, 83.3, 80.2,
79.0, 78.8, 74.0 (8, 16, 1, 6, 1
8, 15, 14, 13th C) 60.9, 59.0, 57.9, 56.0 (16, 1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 49.1 (C of N-ethyl group of methylene) 13.4 (C of N-ethyl group of methyl) 21.3 (Methyl group of acetyl group) C) 6) Mass spectrum analysis m / z 629 (M ⁺ )

(14) Physical properties and analytical data of 3,13-dideoxyaconitine 1) Properties and solubility Colorless crystals having a melting point of 165 to 166 ° C, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, It is soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.38-8.14 (5H, m) (H of benzoyl group) 5.05 (1H, t, J = 4.50) (βH at position 14) 3.52 (3H, s) (1, 6 3,28 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.18 (3H, s) (same as above) 1.43 (3H, s) (H of methyl group of acetyl group at the 8-position) 1.06 (3H, t, J = 7.0) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 172.2 (C of carbonyl of acetyl group at 8-position) 166.0 (C of carbonyl of benzoyl group) 133.1, 130.0, 129.5, 128.5 (C of benzoyl group) 92.1, 89 .2, 85.2, 83.6, 80.2,
76.2, 75.4 (8, 16, 1, 6, 18, 14,
15th place C) 59.0, 57.9, 57.6, 56.0 (18, 1
6,6,1-position bonded methoxy group C) 49.2 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 21.4 (8-position acetyl group methyl) Group C) 6) Mass spectrum analysis m / z 613 (M ⁺ )

(15) Physical property values and analytical data of 8-deoxy-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.40-8.08 (5H, m) (H of benzoyl group) 4.50 (1H, d, J) = 4.98) (βH at position 14) 3.60 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 3.29 (6H, s) (as above) 3.17 ( 3H, s) (same as above) 2.36 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.7 (C of benzoyl group) 132.9, 129.3, 128.3 (C of benzoyl group) 94.1, 85.2, 83.7, 80.1, 77.5
74.0, 72.5 (16, 6, 1, 14, 18, 1
30.7 position C) 60.7, 58.8, 57.8, 55.8 (16, 1
C) 42,3 (C of N-methyl group) 6) Mass spectrum analysis m / z 589 (M ⁺ )

(16) 3,13-dideoxy-14-O
-Physical property value and analytical data of benzoylmesaconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.41-8.22 (5H, m) (H of benzoyl group) 5.03 (1H, t, J = 4.28) (βH at position 14) 3.53 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.17 (3H, s) (same as above) 2.35 (3H, s) (H of the N-methyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of benzoyl group) 133,1,129.7,128.5 (C of benzoyl group) 89.4,85.3,83.2,81.7,80.2,
79.2, 78.5 (16, 1, 6, 15, 18, 1
4,8, C) 59.1, 58.0, 57.6, 56.3 (18, 1
C, derived from a methoxy group bonded to the 6,6,1-position) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 557 (M ⁺ )

(17) Physical properties and analytical data of 3,13-dideoxymesaconitine 1) Properties and solubility Colorless crystals having a melting point of 159-161 ° C, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.20 (5H, m) (H of benzoyl group) 5.05 (1H, t, J = 4.30) (βH at position 14) 3.52 (3H, s) (1, 6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.18 (3H, s) (same as above) 2.35 (3H, s) (H of the N-methyl group) ) 1.43 (3H, s) (H of methyl group at acetyl group at position 8) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 172.2 (C of carbonyl of acetyl group at position 8) 166.0 (C of carbonyl of benzoyl group) 133.0, 129.6, 128.5, (C of benzoyl group) 92.0, 89.2 85.1, 83.6, 80.1,
76.3, 75.5 (8, 16, 1, 6, 18, 14,
15th place C) 59.0, 57.9, 57.6, 56.4 (18, 1
6,6,1 bonded to the methoxy group at position 1) 42.6 (N-methyl group, C) 21.4 (acetyl group, methyl C) 6) Mass spectrometry m / z 599 (M ⁺ )

(18) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O-benzoylmesaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.41-8.22 (5H, m) (H of benzoyl group) 5.02 (1H, t, J = 4.28) (βH at position 14) 3.53 (3H, s) (1,6 , H of a methoxy group at positions 16 and 18) 3.29 (6H, s) (same as above) 3.18 (3H, s,) (same as above) 2.34 (3H, s) (same as above) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of benzoyl group) 133.0, 129.6, 128.3 (C of benzoyl group) 93.1, 85.3, 84.4, 80.3, 80.0,
72.1 (C at positions 16,1,6,18,14,15) 59.0,58.0,57.7,56.5 (18,1
6,6,1 position of methoxy group bonded to C) 42.3 (N-methyl group of C) 6) mass spectrum analysis m / z 557 (M ⁺ )

(19) 3,8-dideoxy-14-O-
Physical property values and analytical data of benzoylmesaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.41-8.05 (5H, m) (H of benzoyl group) 4.48 (1H, d, J = 4.98) (βH at position 14) 3.69 (3H, s) (1,6 , H of a methoxy group at positions 16 and 18) 3.30 (6H, s) (same as above) 3.16 (3H, s) (same as above) 2.35 (3H, s) (H of an N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of benzoyl group) 133.0, 129.5, 128.3, (C of benzoyl group) 94.2, 85.2, 84.2, 80.2, 80.0,
74.0, 72.6 (16, 1, 6, 18, 14, 1
30.8 C) 60.8, 58.9, 57.7, 55.6 (16, 1
C) 42.5 (C of N-methyl group) 6) Mass spectrum analysis m / z 573 (M ⁺ )

(20) Physical property values and analytical data of 14-O-anisoylmesaconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, d, J = 8.90) (H of anisoyl group) 6.89 (2H, d, J = 8.90) (same as above) 4.96 (1H, d, J = 5.90) 30) (βH at position 14) 3.85 (3H, s) (H of methoxy group of anisoyl group) 3.70 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.24 (3H, s) (same as above) 2.35 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group carbonyl) 163.5,131.8, 122.1, 113.5 (C of anisoyl group) 90.6, 83.6, 82.5, 81.8, 79. 3,
78.8, 77.4, 74.8, 71.9 (16, 6,
1, 15, 14, 8, 18, 13, 3rd position C) 60.9, 59.1, 58.0, 55.7 (16, 1
C derived from the methoxy group bonded to the 8,6,1 position) 55.4 (C of the methoxy group of the anisoyl group) 42.3 (C of the N-methyl group) 6) Mass spectrum analysis m / z 615 (M ⁺ )

(21) Physical properties and analytical data of 8-deoxy-14-O-anisoylmesaconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate , Soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.91) (H of anisoyl group) 6.93 (2H, d, J = 8.91) (same as above) 4.46 (1H, d, J = 4. 95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 2.34 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group carbonyl) 163.5,131.8,122.1,113.8 (C of anisoyl group) 94.2,85.3,83.7,80.2,77. 8,
75.0, 72.6, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,58.0,56.0 (16,1
C, a methoxy group bonded to the 8, 6, 1-position) 55.4 (C, a methoxy group of anisoyl group) 42.4 (C, a N-methyl group) 6) Mass spectrometry m / z 603 (M ⁺ )

(22) Physical property values and analytical data of 3-deoxy-14-O-anisoylmessaconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate It is soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, d, J = 8.90) (H of anisoyl group) 6.89 (2H, d, J = 8.90) (Id.) 4.96 (1H, d, J = 5.90) 25) (βH at position 14) 3.85 (3H, s) (H of methoxy group of anisoyl group) 3.72 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 2.34 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group carbonyl) 163.5, 131.8, 122.1, 113.6 (C of anisoyl group) 90.7, 85.2, 83.1, 81.4, 80. 2,
79.4, 78.7, 75.3 (16, 1, 6, 15,
18, 14, 8, 13th position C) 60.9, 59.1, 58.0, 56.2 (16, 1
C, a methoxy group bonded to the 8, 6, 1-position) 55.4 (C, a methoxy group of anisoyl group) 42.3 (C, a N-methyl group) 6) Mass spectrum analysis m / z 599 (M ⁺ )

(23) 3,8-dideoxy-14-O-
Physical Properties and Analytical Data of Anisoyl Mesaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.99 (2H, d, J = 8.90) (H of anisoyl group) 6.92 (2H, d) 4.47 (1H, d, J = 4.95) (βH at position 14) 3.88 (3H, s) (H of the methoxy group of anisoyl group) 70 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.16 (3H) 2.34 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.5,131.8,122.2,113.8 (C of anisoyl group) 94.1,85.2,84.3,80.1,80. 0,
74.3, 72.7 (16, 1, 6, 18, 14, 1
C at position 3,15) 61.7, 59.0, 57.9, 56.1 (16, 1
C, a methoxy group bonded to the 8, 6, 1-position) 55.4 (C, a methoxy group of anisoyl group) 42.4, (C of an N-methyl group) 6) Mass spectrometry m / z 587 (M ⁺ )

(24) 3,13-dideoxy-14-O
-Physical properties and analytical data of Anisoyl Mesaconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.95 (2H, d, J = 8.10) (H of anisoyl group) 6.92 (2H, d, J = 8.10) (same as above) 5.02 (1H, t, J = 4. 55) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.60 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 2.33 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (anisoyl group carbonyl C) 163.4,131.9,122.1,113.5 (anisoyl group C) 89.4,85.3,83.4,81.6,80. 1,
79.3, 78.7 (16, 1, 6, 15, 18, 1
4,8th C) 59.2,58.1,57.9,56.0 (18,1
C, derived from a methoxy group bonded to the 6,6,1-position) 55.4 (C of anisoyl group methoxy group) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 583 (M ⁺ )

(25) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O-anisoylmesaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.90) (H of anisoyl group) 6.93 (2H, d, J = 8.90) (same as above) 5.01 (1H, t, J = 4. 50) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 3.60 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 2.34 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.4, 131.5, 122.1, 113.8 (C of anisoyl group) 93.3, 85.3, 84.5, 80.3, 80. 1,
72.2 (C at positions 16,1,6,18,14,15) 59.2,58.0,57.8,56.1 (16,1
C, a methoxy group bonded to the 8, 6, 1-position) 55.3 (C, a methoxy group of anisoyl group) 42.3, (C of an N-methyl group) 6) Mass spectrum analysis m / z 571 (M ⁺ )

(26) 16-epi-8-deoxy-14
-O-Anisoyl aconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.91) (H of anisoyl group) 6.93 (2H, d, J = 8.91) (same as above) 4.68 (1H, d, J = 4. 95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.13 (3H, t, J = 6.93) (N -H) of methyl group of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.9 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 91.3, 85.2, 83.7, 79.2, 77. 4,
75.9, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 62.2,59.1,57.9,56.1 (16,1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 55.4 (C of the methoxy group of the anisoyl group) 49.1 (C of the methylene of the N-ethyl group) 13.4 (Methyl of the N-ethyl group) C) 6) Mass spectrum analysis m / z 617 (M ⁺ )

(27) Physical property values and analytical data of 16-epi-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, Soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2E, d, J = 8.91) (H of anisoyl group) 6.92 (2H, d, J = 8.91) (same as above) 4.68 (1H, d, J = 4. 95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.86 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s.) (Same as above) 3.18 (3H, s) (same as above) 1.11 (3H, t, J = 6.95) ( H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.9 (C of anisoyl group) 163.5,131.7,122.2,113.8 (C of anisoyl group) 91.4,85.3,84.2,80.2,79. 0,
75.8, 72.4, (16, 1, 6, 18, 14, 1
C at positions 3 and 15) 61.2, 59.1, 57.9, 56.1 (16, 1
C, the methoxy group bonded to the 8, 6, 1-position) 55.4 (C, the methoxy group of the anisoyl group) 49.1 (C, the methylene of the N-ethyl group) 13.4 (the methyl of the N-ethyl group) C) 6) Mass spectrum analysis m / z 601 (M ⁺ )

(28) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 5.26 (1H, t, J = 4. 53) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 1.10 (3H, t, J = 6.95) (N -H) of methyl group of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of anisoyl group carbonyl) 163.5, 13L6, 122.1, 113.8 (C of anisoyl group) 90.2, 85.1, 84.5, 79.9, 78.9,
72.0 (C at 16,1,6,18,14,15th position) 59.5,58.3,58.0,56.1 (16,1
55.3 (C of the methoxy group of the anisoyl group) 49.1 (C of the methylene group of the N-ethyl group) 13.4 (C of the methylene group of the N-ethyl group) C) 6) Mass spectrum analysis m / z 585 (M ⁺ )

(29) 16-epi-8-deoxy-14
-O-Benzoyl aconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.12 (5H, m) (H of benzoyl group) 4.72 (1H, d, J = 4.97) (βH at position 14) 3.85 (3H, s) (1, 6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.09 (3H, t, J = 7.0) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.8 (C of benzoyl group) 133.2, 130.0, 129.6, 128.6 (C of benzoyl group) 91.2, 85.2, 83.7, 79.1, 77. 5,
76.2, 72.4, 71.9 (16, 6, 1, 1
4,18,13,15,3rd position C) 61.3,59.0,57.9,56.1 (16,1
Methoxy group C bonded to the 8,6,1 position 49.0 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) mass spectrometry m / z 587 ( M ⁺ )

(30) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.40-8.15 (5H, m) (H of benzoyl group) 4.73 (1H, d, J = 4.98) (βH at position 14) 3.87 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.29 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.10 (3H, t, J = 6.98) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.9 (C of carbonyl of benzoyl group) 133.1, 130.0, 129.6, 128.6 (C of benzoyl group) 91.2, 85.2, 84.2, 80.2, 79. 0,
72.6 (C at positions 16,1,6,18,14,15) 61.2,59.0,57.9,56.1 (16,1
C, the methoxy group bonded to the 8,6,1 position 49.0 (C of the methylene of the N-ethyl group) 13.5 (C of the methyl of the N-ethyl group) 6) Mass spectrum analysis m / z 571 ( M ⁺ )

(31) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform and benzene It is soluble in ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.38-8.15 (5H, m) (H of benzoyl group) 5.25 (lH, t, J = 4.49) (βH at position 14) 3.69 (3H, s) (1,6 , H of the methoxy group at positions 16 and 18) 3.28 (6H, s) (same as above) 3.18 (3H, s) (same as above) 1.09 (3H, t, J = 6.98) (same as above) H) of methyl group of N-ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of carbonyl of benzoyl group) 133.1, 130.0, 129.7, 128.6 (C of benzoyl group) 90.3, 85.2, 84.4, 80.2, 78. 9,
72.3 (C at positions 16, 16, 6, 18, 14, 15) 59.6, 57.9, 57.6, 56.0 (18, 1
6,6,1 bonded to C-position of methoxy group 49.1 (N-ethyl group of methylene C) 13.4 (N-ethyl group of methyl C) 6) mass spectrometry m / z 555 ( M ⁺ )

(32) 16-epi-8-deoxy-14
Physical properties and analytical data of -O-benzoylmesaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.40-8.08 (5H, m) (H of benzoyl group) 4.74 (1H, d, J) = 4.98) (βH at position 14) 3.17 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 3.29 (6H, s) (as above) 3.17 ( 3H, s) (same as above) 2.38 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.8 (C of benzoyl group) 132.9, 129.3, 128.3 (C of benzoyl group) 91.0, 85.2, 83.7, 79.1, 77.5
74.8, 72.5 (16, 6, 1, 14, 18, 18, 1)
31.1, C) 61.1, 58.8, 57.8, 55.8 (16, 1
C) 42.3 (C of N-ethyl group) 6) Mass spectrum analysis m / z 589 (M ⁺ )

(33) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform and benzene It is soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.41-8.22 (5H, m) (H of benzoyl group) 5.27 (1H, t, J) = 4.28) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1,6,16 and 18) 3.29 (6H, s) (as above) 3.18 ( 3H, s) (same as above) 2.36 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 165.0 (C of benzoyl group) 133.0, 129.6, 128.3 (C of benzoyl group) 90.1, 85.3, 84.4, 80.3, 79.0,
72.1 (C at positions 16,1,6,18,14,15) 59.5,58.0,57.7,56.5 (18,1
6,6,1 position of methoxy group bonded to C) 42.3 (N-methyl group of C) 6) mass spectrum analysis m / z 557 (M ⁺ )

(34) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-benzoylmesaconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol It is soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.41-8.05 (5H, m) (H of benzoyl group) 4.73 (1H, d, J = 4.98) (βH at position 14) 3.86 (3H, s) (1, 6 , H of a methoxy group at positions 16 and 18) 3.30 (6H, s) (same as above) 3.16 (3H, s) (same as above) 2.37 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 165.0 (C of carbonyl of benzoyl group) 133.0, 129.5, 128.3, (C of benzoyl group) 91.0, 85.2, 84.2, 80.2, 79.0,
75.0, 72.6 (16, 1, 6, 18, 14, 1
C at positions 3 and 15) 61.2, 58.9, 57.7, 55.6 (16, 1
C) 42.5 (C of N-methyl group) 6) Mass spectrum analysis m / z 573 (M ⁺ )

(35) 16-epi-8-deoxy-14
-O-Anisoyl Mesaconin Physical Properties and Analytical Data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.91) (H of anisoyl group) 6.93 (2H, d, J = 8.91) (same as above) 4.71 (1H, d, J = 4.91) 95) (βH at position 14) 3.87 (3H, s) (H of the methoxy group of the anisoyl group) 3.84 (3H, s) (H of the methoxy group at the 1,6,16 and 18 positions) 31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 2.35 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of anisoyl group) 163.5, 131.8, 122.1, 113.8 (C of anisoyl group) 91.1, 85.3, 83.7, 79.2, 77. 8,
75.8, 72.6, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 62.2,59.1,58.0,56.0 (16,1
C, a methoxy group bonded to the 8, 6, 1-position) 55.4 (C, a methoxy group of anisoyl group) 42.4 (C, a N-methyl group) 6) Mass spectrometry m / z 603 (M ⁺ )

(36) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-anisoylmesaconin 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, Soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.90) (H of anisoyl group) 6.92 (2H, d, J = 8.90) (same as above) 4.72 (1H, d, J = 4.90) 95) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 3.84 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.16 (3H, s) (same as above) 2.35 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of anisoyl group) 163.5, 131.8, 122.2, 113.8 (C of anisoyl group) 91.0, 85.2, 84.3, 80.1, 79. 0,
75.1, 72.7 (16, 1, 6, 18, 14, 1
C at position 3,15) 62.1, 59.0, 57.9, 56.1 (16, 1
C, a methoxy group bonded to the 8, 6, 1-position) 55.4 (C, a methoxy group of anisoyl group) 42.4, (C of an N-methyl group) 6) Mass spectrometry m / z 587 (M ⁺ )

(37) Physical property values and analytical data of 16-epi-3,8,13-trideoxy-14-O-anisoylmessaconin 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.90) (H of anisoinole group) 6.93 (2H, d, J = 8.90) (same as above) 5.25 (1H, t, J = 4. 50) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 3.77 (3H, s) (H of methoxy group at 1,6,16 and 18) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.16 (3H, s) (same as above) 2.35 (3H, s) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.1 (C of anisoyl group) 163.4, 131.5, 122.1, 113.8 (C of anisoyl group) 90.3, 85.3, 84.5, 80.3, 79. 1,
72.2 (C at positions 16, 16, 6, 18, 14, 15) 59.6, 58.0, 57.8, 56.1 (16, 1
C, a methoxy group bonded to the 8, 6, 1-position) 55.3 (C, a methoxy group of anisoyl group) 42.3, (C of an N-methyl group) 6) Mass spectrum analysis m / z 571 (M ⁺ )

(38) Physical properties and analytical data of 8-deoxy-14-O-trimethylgalloylaconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetic acid Soluble in ethyl, pyridine and dimethyl sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.35 (2H, s) (H of trimethylgalloyl group) 5.03 (1H, d, J = 4) (0.7 Hz) (βH at position 14) 3.88 (9H, s) (H of methoxy group of trimethylgalloyl group) 3.53 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.30 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.12 (3H, t, J = 7.0 Hz) ) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of trimethylgalloyl group) 124.3, 107.5, 145.2, 133.8 (C of trimethylgalloyl group) 94.1, 85.2, 83.7, 80. 3,77.5,
75.2, 72.4, 72.0 (16, 6, 1, 14,
C at positions 18, 13, 15, and 3) 61.9, 59.3, 58.0, 55.9 (16, 1
C derived from the methoxy group bonded to the 8,6,1 position) 55.9 (C of the methoxy group of the trimethylgalloyl group) 49.0 (C of the methylene of the N-ethyl group) 13.5 (N-ethyl group 6) Mass spectrometry m / z 677 (M ⁺ ) 7) Elemental analysis C ₃₅ H ₅₁ NO ₁₂ , Calculated C: 62.02, H:
7.58, N: 2.07 Found C: 62.18, H: 7.69, N: 2.05

(39) Physical property values and analytical data of 8-deoxy-14-O-veratroyl aconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate , Soluble in pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV-1 absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.87-7.68 (3H, m) (H of veratroyl group) 5.06 (1H, d, J = 4.6 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group Methoxy group H) 3.54 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.12 (3H, t, J = 7.0 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl of veratroyl group) 122.5, 110.5, 153.1, 148.1, 1
12.3 (C of veratroyl group) 94.2, 85.0, 83.7, 80.4, 77.4,
75.3, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.9,56.0 (16,1
55.8 (C of the methoxy group of the veratroyl group) 49.1 (C of the methylene of the N-ethyl group) 13.4 (C of the methylene group of the N-ethyl group) C) 6) Mass spectrum analysis m / z 647 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₉ NO ₁₁ , Calculated C: 63.
04, H: 7.62, N: 2.16 Found C: 63.21, H: 7.58, N = 2.05

(40) Physical properties and analytical data of 8-deoxy-14-O-p-chlorobenzoyl aconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.97 (2H, d, J = 8.8 Hz) (H of p-chlorobenzoyl group) 7.43 (2H, d, J = 8.8 Hz) (same as above) 4.90 (1H, d, J) = 4.8 Hz) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (ibid) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.14 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic field Resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 165.2 (C of carbonyl of p-chlorobenzoyl group) 131.1, 128.8, 128.1, 139.6 (p
-C of the chlorobenzoyl group 94.1,85.0,8
3.6, 80.7, 77.3, 75.0, 72.4, 7
1.9 (16, 6, 1, 14, 18, 13, 15, 3rd-position C 61.7, 59.1, 57.8, 56.0 (16, 1
8, 6, 1-position methoxy group C) 49.0 (N-
C methylene ethyl) 13.3 (C) 6 of methyl N- ethyl) mass spectroscopy ^{m / Z 621,623 (M +)} 7) Elemental analysis _{C 32 H 44 NO 3 Cl 7} , Calculated C: 61.78,
H: 7.13, N: 2.25 measured value
C: 61.93, H: 7.30, N: 2.11

(41) Physical property values and analytical data of 8-deoxy-14-O-m-chlorobenzoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by adding ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 8.02-7.35 (5H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 5.1 Hz) (βH at position 14) 3.71 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 165.0 (C of m-chlorobenzoyl group carbonyl) 131.6, 133.0, 129.7, 134.5, 1
27.8 (C of m-chlorobenzoyl group) 94.1, 85.1, 83.6, 80.9, 77.3
75.0, 72.4, 71.9 (16, 6, 1, 14
18,1
C, 3,15,3) 61.5,59.1,57.8,56.1 (16,8,
6, C 19.0 of methoxy group at position 1 (C of N-ethyl methylene) 13.3 (C of N-ethyl methyl) 6) Mass spectrum analysis m / z 621,623 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₄ NO ₃ Cl, calculated C: 61.78,
H: 7.13, N: 2.25 Found C: 61.75, H: 7.23, N: 2.16

(42) Physical properties and analytical data of 8-deoxy-14-O-α-methyl- (4- (α-methylacetic aced) -phenyl) acetylaconin 1) Properties and solubility Amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis: The following signals are shown (δ, ppm) 7.30 (4H, s) (H of benzene ring) 4.91 (1H, d, J = 4. 7 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.45 (3H, s) (same as above) 3.30 (3H, s) 3.29 (3H, s) (same as above) 3.63 (2H, q, J = 7.0 Hz) (H of methyl of α-methylacetyl and α-methylacetic acid) 42 (6H, d, J = 7.0 Hz) (H 1.11 (3H, t, J = 7.0 Hz) of methyl of a-methylacetyl and a-methylacetylacid) (methyl of N-ethyl) ^{H) 5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ shows the analysis following signals (Δ, ppm). 180.5 (C of carboxyl) 166.0 (C of carbonyl) 140.4, 139.3, 128.2, 127.0 (C of benzene ring) 60.4, 60.2 (α-methylacetyl and C) of methine of α-methyl acetic acid) 18.2, 18.1 (C of methine of α-methyl acetyl and a-methyl acetyl acid) 94.5, 85.0, 83.7, 80.4 , 77.5,
75.3, 72.4, 72.0 (16, 6, 1, 1
4,18,13,15,3rd position C) 61.9,59.2,58.0,56.1 (16,
8, 6, 1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.2 (N-ethyl methyl C) 6) Mass spectrometry m / z 687 (M ⁺ ) 7 ) elemental analysis C ₃₇ H ₅₃ NO _11, calculated value C: 64.61, H:
7.77, N: 2.04 Found C: 64.68, H: 7.76, N: 2.18

(43) Physical property values and analytical data of 8-deoxy-14-O-methylaconine 1) Properties and solubility Colorless, non-contained powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.62 (3H, s) (H of the methoxy group at positions 1, 6, 16, 18 and 14) 3.39 (3H, s) (same as above) 3.38 (3H, s) (same as above) 3 .31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 4) ^13C nucleus Magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 93.4, 84.7, 83.5, 81.3, 77.5,
77.2, 72.4, 72.0 (16, 6, 1, 14,
18, 13, 15, 15, 3rd position C) 60.6, 59.2, 58.3, 58.1, 56.0
(C of methoxy group at positions 16, 18, 6, 1, 14) 49.4 (C of N-ethyl methylene) 14.1 (C of N-ethyl methyl) 5) Mass spectrum analysis m / z 497 (M ⁺ ) 6) Elemental analysis C ₂₆ H ₄₃ NO ₈ , calculated C: 62.75, H:
8.71, N: 2.8 Actual value C: 62.55, H: 8.86, N: 2.6

(44) Physical Properties and Analytical Data of 8-Deoxy-14-O-benzylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethyl sulfoxide and insoluble in hexane water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.48 (2H, s) (H of methylene of benzyl group) 3.64 (3H, s) (methoxy at positions 1, 6, 16 and 18) Group H) 3.30 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.08 (3H, t, J = 7.0 Hz) (H of methyl N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 126.5, 127.0, 128.3, 141.5
(C of benzyl group) 64.1 (C of benzyl group of methylene) 93.6,84.5,83.1,81.2,77.4
77.3, 72.4, 72.1 (16, 6, 1, 1
4,18,13,15,3rd position C) 60.3,59.1,58.1,56.0 (16,1
8,6,1-position methoxy group C) 49.5 (N-ethyl methylene C) 14.0 (N-ethyl methyl C) 6) Mass spectrometry m / z 573 (M ⁺ ) 7 ) Elemental analysis C ₃₂ H ₄₇ NO ₈ , calculated C: 66.99, H:
8.26, N: 2.25 Found C: 67.12, H: 8.37, N: 2.45

(45) Physical properties and analytical data of 8-deoxy-14-O-crotyl aconin 1) Properties and solubility A colorless, non-crystalline powder, which was obtained from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethylsulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 5.70 (2H, m) (H of double bond of crotyl group) 4.10 (2H, m) (H of methylene of crotyl group) 3.68 (3H, s) (1,6,16 and 18) 3.40 (3H, s) (same as above) 3.27 (6H, s) (same as above) 1.70 (3H, d, J = 6.3 Hz) (crotyl group methyl) H) 1.12 (3H, t, J = 7.3 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 130.8, 123.7 (C of double bond of crotyl group) 93.4, 84.6, 83.5, 81.2, 77.5
77.2, 72.4, 72.0 (16, 6, 1, 1
4,18,13,15,3rd position C) 60.5,59.1,58.0,55.5 (16,1
8,6,1 position methoxy group C) 49.5 (N-ethyl methylene C) 13.9 (N-ethyl methyl C) 12.7 (crotyl group methyl group C) 5) Mass spectrum analysis m / z 537 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₈ , calculated value C: 64.78, H:
8.81, N: 2.6 Actual value C: 65.01, H: 8.93, N: 2.47

(46) Physical properties and analysis data of 8-deoxy-14-O-o-chlorobenzoyl aconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00-7.45 (5H, m) (H of o-chlorobenzoyl group) 4.91 (1H, d, J = 4.8 Hz) (βH at position 14) 3.70 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of carbonyl of o-chlorobenzoyl group) 129.9, 136.0, 128.7, 133.8 1
26.3 (C of o-chlorobenzoyl group) 94.1, 85.0, 83.5, 80.8, 77.3
75.1, 72.5, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.7,59.1,57.9,56.0 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) 6) Mass spectrometry m / z 621,623 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₄ NOCl, calculated C: 61.78, H:
7.13, N: 2.25 Found C: 61.86, H: 7.40, N: 2.18

(47) Physical property values and analytical data of 8-deoxy-14-O-m-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.64-7.26 (5H, m) (H of m-anisoyl group) 4.92 (1H, d) , J = 4.6 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy of m-anisoyl group) 3.87 (3H, s) (methoxy at positions 1, 6, 16 and 18) Group H) 3.71 (3H, s) (same as above) 3.30 (6H, s) (same as above) 1.18 (3H, t, J = 7.0 Hz) (H of methyl N-ethyl) 5) 13C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of m-anisoyl group carbonyl) 131.2, 121.4, 129.5, 118.3, 1
58.9, 115.2 (C of m-anisoyl group) 94.3, 85.1, 83.7, 80.2, 77.5.
75.3, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3 position) 55.4 (C of methoxy group of m-anisoyl group) 61.6,59.1,58.0,56.1 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) 6) mass spectrometry m / z 617 (M ⁺ ) 7 ) elemental analysis C ₃₃ H ₄₇ NO _10, calculated value C: 64.16, H:
7.67, N: 2.27 Found C: 64.19, H:
7.62, N: 2.20

(48) Physical property values and analytical data of 8-deoxy-14-O-acetylaconine 1) Properties and solubility Colorless prism crystals having a melting point of 105 to 107 °, ether, chloroform, benzene, ethanol, Methanol, ethyl acetate, pyridine, dimethyl sulfoxide
It is soluble and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 4.97 (1 H, d, J = 5.0 Hz) (βH at position 14) 3.65 (3H, s) (positions 1, 6, 16 and 18) 3.37 (3H, s) (same as above) 3.28 (6H, s) (same as above) 2.05 (3H, s) (methyl H of acetyl group) 1.10 ( 3H, t, J = 7 Hz) (H of methyl of N-ethyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 171.4 (C of carbonyl of acetyl group) 94.3, 85.1, 83 .7,80.2,76.6,
75.3, 72.4, 72.0 (16, 6, 1, 14,
18,13,15,3rd position C) 61.6,59.0,57.9,56.0 (16,1
8,6,1 position methoxy C) 49.1 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) 21.5 (acetyl methyl methyl C) 5) Mass spectrum Analysis m / z 525 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₉ , calculated C: 61.70, H: 8.
25, N: 2.66 Actual value: C: 61.56, H: 8.31, N: 2.54

(49) 8-Deoxy-14-O- (4-
Physical properties and analytical data of methyl) pentylaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.40 (3H, s) (ibid.) 27 (6H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of methyl in N-ethyl) 1.02 (6H, d, J = 7.0 Hz) (4- H) 3) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl of methylpentyl group 93.4, 84.6, 83.3, 81.0, 77.4
77.2, 72.4, 71.9 (16, 6, 1, 14,
C, 18,13,15,3) 60.5,59.1,58.0,55.5 (16,1
Methoxy group C at 8,6,1 position 49.3 (N-ethyl methylene C) 13.9 (N-ethyl methyl C) 21.3 (4-methylpentyl methyl C) 4 ) mass spectrometry 567 ^(M +) 5) elemental analysis C ₃₁ H ₅₃ NO _8, calculated C: 65.58, H:
9.41, N: 2.47 Found C: 65.43, H: 9.65, N: 2.36

(50) N-desethyl-8-deoxy-
Physical property value and analytical data of 14-O-anisoylaconine 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (Id.) 4.95 (1H, d, J = 5. 0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (Δ, ppm). 166.0 (C of carbonyl of anisoyl group) 163.5,131.8,113.7,122.1.
(C of anisoyl group) 94.3, 85.2, 83.7, 80.2, 77.4
75.1, 72.4, 72.0 (16, 6, 1, 1
4,18,13,15,3rd position C) 61.9,59.0,57.9,56.1 (16,1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 55.4 (C of the methoxy group of the anisoyl group) 6) Mass spectrum analysis m / z 589 (M ⁺ ) 7) Elemental analysis C ₃₁ H ₄₃ NO ₁₀ , Calculated value C: 63.14, H:
7.35, N: 2.38 Found C: 63.39, H: 7.33, N: 2.02

(51) N-desethyl-N-amyl-8
Physical properties and analytical data of -deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder that can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 4.95 (1H, d, J = 5. 0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.70 (3H, s) (H of methoxy group at 1, 6, 16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 0.98 (3H, t, J = 7.0 Hz) ( H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl N-amyl. The following signals are shown (δ, ppm). 166.0 (C of carbonyl of anisoyl group) 163.8, 131.8, 113.5, 122.2
(C of anisoyl group) 94.3, 85.3, 83.6, 80.0, 77.6,
75.1, 72.5, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.8,56.0 (16,1
C, derived from a methoxy group bonded to the 8,6,1 position) 55.4 (C of methoxy of anisoyl group) 13.1 (C of N-amyl methyl) 6) Mass spectrum analysis m / z 659 (M ⁺ 7) Elemental analysis C ₃₆ H ₅₃ NO ₁₀ , Calculated C: 65.53, H:
8.10, N: 2.12 Found C: 65.81, H: 8.09, N: 2.18

(52) N-desethyl-N-propyl-
Physical properties and analytical data of 8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. Soluble, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d) 4.93 (1H, d, J = 5.o) (βH at position 14) 3.87 (3H, s) (H of the methoxy group of the anisoyl group) 69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.24 (3H) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signal (δ 165.9 (C of carbonyl of anisoyl group) 163.6, 131.8, 122.2, 11 .7
(C of anisoyl group) 94.3, 85.3, 83.7, 80.2, 77.5,
75.0, 72.3, 71.9 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.8,56.1 (16,1
C, derived from a methoxy group bonded to the 8,6,1 position) 55.4 (C of methoxy of anisoyl group) 13.1 (C of methyl of N-propyl) 6) Mass spectrum analysis m / z 631 (M ⁺ ) 7) elemental analysis C ₃₄ H ₄₉ NO _10, calculated value C: 64.64, H:
7.82, N: 2.22 actual value: C: 64.85, H: 7.66, N: 2.01

(53) Physical Properties and Analytical Data of N-Desethyl-N- (4-methyl) pentyl-8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.94 (1H, d, J = 5. 0) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 29 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.02 (6H, d, J = 7.0 Hz) (N H) of methyl of-(4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group carbonyl) 163.6, 131.7, 113.4, 122.1 (C of anisoyl group) 94.5, 85.3, 83.5, 80.0, 77. 6,
75.0, 72.5, 71.9 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.8,56.0 (16,1
C derived from the methoxy group bonded to the 8,6,1 position) 55.4 (Methoxy C of anisoyl group) 21.5 (Methyl C of N- (4-methyl) pentyl) 6) Mass spectrum analysis m / z 673 (M ⁺ ) 7) Elemental analysis C ₃₇ H ₅₅ NO ₁₀ , Calculated C: 65.95, H:
8.23, N: 2.08 Found C: 66.17, H: 8.29, N: 2.05

(54) N-desethyl-N-acetyl-
Physical properties and analytical data of 8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. Soluble, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.93 (1H, d, J = 5. 0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.34 (3H, s) (methyl of N-acetyl group) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.8 (C of N-acetyl carbonyl) 165.9 (C of carbonyl of anisoyl group) 163.6, 131.8, 113.7, 122.2 (C of anisoyl group) 94.3, 83. 7, 80.2, 79.9, 77.4,
75.1, 72.4, 72.0 (16, 6, 14, 1, 1,
C, 18,13,15,3) 61.8,59.1,57.9,56.1 (16,1
C derived from a methoxy group bonded to the 8,6,1 position) 55.4 (C of anisoyl group methoxy) 22.4 (C of N-acetyl group methyl) 6) Mass spectrum analysis m / z 631 (M ⁺ ) 7) Elemental analysis C ₃₃ H ₄₅ NO ₁₁ , Calculated C: 62.74, H:
7.18, N: 2.22 Found C: 62.62, H: 7.10, N: 2.18

(55) Physical properties and analytical data of N-desethyl-N-benzoyl-8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.82 to 7.10 (5H, m) (C of N-benzoyl group) 7.99 (2H, d) , J = 8.9 Hz) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 4.95 (1H, d, J = 5.0) (βH at position 14) ) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.70 (3H, s) (H of methoxy group at 1, 6, 16 and 18 positions) 3.31 (3H, s) ( 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 165.9, 165.7 (C of N-benzoyl group) 163.7, 131.7, 113.6, 122 .1 (C of anisoyl group) 133.9 133,5 128.6, 128.6,
128.2, 127.6 (C of benzoyl group)
4,83.7,80.1,79.8,77.5,75.
1,72.4,71.9 (16,6,14,1,18,
13,15,3rd position C) 61.8,59.1,57.8,56.0 (16,1
C, derived from a methoxy group bonded to the 8, 6, 1-position) 55.4 (C of methoxy of anisoyl group) 6) Mass spectrum analysis m / z 693 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₇ NO ₁₁ , Calculated value C: 65.79, H:
6.83, N: 2.02 Found C: 65.91, H: 6.79, N: 2.15

(56) 16-epi-8-deoxy-14
Physical properties and analytical data of -O-trimethylgalloylaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide And is insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 1) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.35 (2H, s) (H of trimethylgalloyl group) 5.03 (1H, d, J = 4.7 Hz)) (βH at position 14) 3.88 (9H, s) (trimethylgalloyl group) Methoxy H) 3.75 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.30 (3H, s) (same as above) Top) 3.26 (3H, s) (same as above) 1.12 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 165.9 (C of trimethylgalloyl group) 124.3, 107.5, 145.2, 133.8 (C of trimethylgalloyl group) 91.1, 85.2, 83.7, 80. 3,77.5,
75.2, 72.4, 72.0 (16, 6, 1, 14,
C at position 18, 13, 15, 3) 55.9 (C of methoxy group of trimethylgalloyl group) 61.9, 59.3, 58.0, 56.1 (16, 1)
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) Mass spectrometry m / z 677 (M ⁺ )

(57) 16-epi-8-deoxy-14
Physical properties and analytical data of -O-veratroyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane Insoluble in water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.87-7.68 (3H, m) (H of veratroyl group) 5.06 (1H, d, J = 4.6 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group Methoxy H) 3.76 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3,29 (3H, s) (same as above) ) 3.26 (3H, s) (same as above) 1.12 (3H, t, J = 7.0Hz) ( methyl of N- ethyl group ^{H) 5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl of veratroyl group) 122.5, 110.5, 153.1, 148.1, 1
12.3 (C of veratroyl group) 91.2, 85.0, 83.7, 80.4, 77.4,
75.3, 72.4, 72.0 (16, 6, 1, 14,
C at position 18, 13, 15, and 3) 55.8 (C of methoxy group of veratroyl group) 61.8, 59.1, 57.9, 56.0, (16, 1)
8,6,1-position methoxy group C) 49.1 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) mass spectrometry m / z 647 (M ⁺ )

(58) 16-epi-8-deoxy-14
Physical properties and analytical data of -Op-chlorobenzoylaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.91 (2H, d, J = 8.9) (H of p-chlorobenzoyl group) 7.38 (2H, d, J = 8.9) (same as above) 5.10 (1H, d, J) = 4.8 Hz) (βH at position 14) 3.85 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.43 (3H, s) (same as above) 3.36 ( 6H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. (Δ, ppm). 165.0 (C of carbonyl of p-chlorobenzoyl group) 130.5, 130.7, 128.7, 139.6 (p
C) 91.1, 84.8, 83.5, 80.7, 77.3
75.2, 73.0, 72.1 (16, 6, 1, 1
4,18,13,15,3rd position C) 62.2,59.2,58.0,56.0 (16,1
8,6,1-position methoxy group C) 49.2 (N-ethyl group methylene C) 13.3 (N-ethyl group methyl C) 6) Mass spectrum analysis m / z 621,623 ( M ⁺ )

(59) 16-epi-8-deoxy-14
-O-m-chlorobenzoyl aconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.30 (5H, m) (H of m-chlorobenzoyl group) 5.05 (1H, d, J = 4.7 Hz) (βH at position 14) 3.86 (3H, s) ( 1.32 (3H, s) (same as above) 3.30 (6H, s) (same as above) 1.12 (3H, t, J = 7. 0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.2 (C of carbonyl of m-chlorobenzoyl group) 131.6, 129.8, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 91.4, 84.9, 83.4, 80.6, 77.2.
75.3, 73.0, 72.1 (16, 6, 1, 14,
C, 18,13,15,3rd position) 62.2,59.2,58.1,56.0 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl group methylene C) 13.3 (N-ethyl group methyl C) 6) mass spectrometry m / z 621,623 ( M ⁺ )

(60) 16-epi-8-deoxy-14
-O-α-methyl- (4- (α-methylacetic acid) phenyl) acetylaconin physical property values and analytical data 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol It is soluble in methanol, ethyl acetate, pyridine and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.30 (4H, s) (H of propionyl group) 4.91 (1H, d, J = 4.7 Hz)) (βH at position 14) 3.86 (3H, s) (1, 6, 16 and H of the methoxy group at position 18) 3.45 (3H, s) (same as above) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.63 (2H, s) q, J = 7.0 Hz) (H of propionyl group methine) 1.42 (6H, d, J = 7.0 Hz) (propionyl group methyl H) 1.11 (3H, t, J = 7.0 Hz) 0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 180.5 (C of the carboxyl of the propionyl group) 166.0 (C of the carbonyl of the propionyl group) 140.4, 139.3, 128.2, 127.0 (C of the propionyl group) 60.4, 60.2 (C of propionyl group methine) 18.2, 18.1 (C of propionyl group methyl) 90.5, 85.0, 83.7, 80.4, 77.5,
75.3, 72.4, 72.0 (16, 6, 1, 14,
C at position 18, 13, 15, 15) 61.9, 59.2, 58.0, 56.1 (16, 1
8,6,1-position methoxy group C) 49.0 (N-ethyl group, methylene C) 13.2 (N-ethyl group, methyl C) 6) Mass spectrum analysis m / z 687 (M ⁺ )

(61) 16-epi-8-deoxy-14
-O-Methylaconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16, 14, and 18) 3.39 (3H, s) (same as above) 3.38 (3H, s) (same as above) 3 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 90.3, 84.7, 83.5, 81.3, 77.5,
77.2, 72.4, 72.0 (16, 6, 14, 1
8, 13, 15, 3rd position C) 60.6, 59.2, 58.3, 58.1, 56.0
(C at 4th position of 18, 18, 14, 6, 1 (C of N-ethyl group methylene) 14.1 (C of N-ethyl group methyl) 5) Mass spectrum analysis m / z 497 (M ⁺ )

(62) 16-epi-8-deoxy-14
-O-benzylaconine physical properties and analytical data 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane. , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.48 (2H, s) (H of methylene of benzyl group) 3.80 (3H, s) (methoxy group at 1, 6, 16 and 18 positions) H) 3.30 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.08 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 126.5, 127.0, 128.3, 141.5
(C of benzyl group) 64.1 (C of benzyl group methylene) 90.5, 84.5, 83.1, 81.2, 77.4
77.3, 72.4, 72.1 (16, 6, 1, 14,
C, 18,13,15,3) 60.3,59.1,58.1,56.0 (16,1
8,6,1-position methoxy group C) 49.5 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 6) Mass spectrometry m / z 573 (M ⁺ )

(63) 16-epi-8-deoxy-14
-O-crotyl aconin physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.70 (2H, m) (H of crotyl double bond) 4.10 (2H, m) (H of methylene of crotyl group) 3.82 (3H, s) (1,6,16 and 18) 3.40 (3H, s) (same as above) 3.27 (6H, s) (same as above) 1.70 (3H, d, J = 6.3 Hz) (methyl of crotyl group) H) 0.88 (3H, t, J = 7.3 Hz) (H of methyl of N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). . 130.8, 123.7 (C of crotyl group double bond) 90.4, 84.6, 83.5, 81.2, 77.5
77.2, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 60.5,59.1,58.0,55.5 (16,1
Methoxy group C at 8,6,1 position 49.5 (N-ethyl group methylene C) 13.9 (N-ethyl group methyl C) 12.7 (crotyl group methyl group C) 5) Mass spectrum analysis m / z 537 (M ⁺ )

(64) 16-epi-8-deoxy-14
-O-Chlorobenzoyl aconine physical properties and analytical data 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00-7.45 (5H, m) (H of o-chlorobenzoyl group) 5.02 (1H, d, J = 4.8 Hz) (βH at position 14) 3.85 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.45 (3H, s) (same as above) 3.40 (6H, s) (same as above) 0.88 (3H, t, J = 7. 0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl of o-chlorobenzoyl group) 129.9, 136.0, 128.7, 133.8, 1
26.3 (C of o-chlorobenzoyl group) 90.3, 84.9, 83.5, 80.4, 77.3
75.1, 72.6, 72.0 (16, 6, 1, 14,
C, 18,13,15,3) 61.8,59.1,57.9,56.0 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) mass spectrometry m / z 621,623 ( M ⁺ )

(65) 16-epi-8-deoxy-14
-O-m-Anisoyl aconin physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.64-7.26 (m, 5H) (H of m-anisoyl group) 4.92 (1H, d, J = 4.6 Hz) (βH at position 14) 3.71 (3H, s) (1) 3.30 (6H, s) (same as above) 3.89 (3H, s) (same as above) 3.91 (3H, s) (m-anisoyl group) 1.18 (3H, t, J = 7.0 Hz) (H of methyl N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ , Ppm). 165.0 (C of m-anisoyl group carbonyl) 131.2, 121.4, 129.5, 118.3, 1
58.9, 115.2 (C of m-anisoyl group) 90.2, 85.1, 83.7, 80.2, 77.5,
75.3, 72.4, 72.0 (16, 6, 1, 14,
C, 18,13,15,3 position) 55.4 (methoxy C of m-anisoyl group) 61.6,59.1,58.0,56.1 (16,1
8,6,1 position methoxy group C) 49.1 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) mass spectrometry m / z 617 (M ⁺ )

(66) 16-epi-N-desethyl-8
Physical properties and analytical data of -deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder that can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisosoyl group) 6.94 (2H, d, J = 8.9 Hz) (same as above) 5.15 (1H, d, J = 5. OHz) (βH at position 14) 3.84 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (ibid) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 166.0 (C of anisoyl group) 163.5, 131.8, 113.7, 122.1 (C of anisoyl group) 91.2, 85.1, 83.7, 80.2, 77. 4,
75.9, 72.4, 72.0 (16, 6, 1, 14,
C at position 18, 13, 15, and 3) 55.4 (C of methoxy of anisoyl group) 62.2, 59.0, 57.9, 56.1 (16, 1
C) of the methoxy group at the 8,6,1 position 6) Mass spectrometry m / z 573 (M ⁺ )

(67) 16-epi-N-desethyl-N
Physical properties and analytical data of -amyl-8-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.93 (2H, d, J = 8.9 Hz) (same as above) 5.14 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.83 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (N- Amyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.8, 113.5, 122.2 (C of anisoyl group) 91.2, 85.3, 83.6, 80.0, 77. 6,
76.0, 72.5, 72.0 (16, 6, 1, 14,
C, 18,13,15,3 position) 55.4 (methoxy C of anisoyl group) 62.2,59.1,57.8,56.0 (16,1
8,6,1-position methoxy group C) 13.1 (N-amyl methyl C) 6) mass spectrometry m / z 671 (M ⁺ )

(68) 16-epi-N-desethyl-N
-Propyl-8-deoxy-14-O-anisoylaconine physical property values and analytical data 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.94 (2H, d, J = 8.9 Hz) (same as above) 5.12 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.10 (3H, t, J = 7.0 Hz) (N- H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of propyl methyl. The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 91.2, 85.2, 83.7, 80.2, 77. 5,
76.0, 72.3, 71.9 (16, 6, 1, 14,
C, 18,13,15,3 position) 55.4 (methoxy C of anisoyl group) 62.2,59.1,57.9,56.1 (16,1
8,6,1 position methoxy group C) 13.0 (N-propyl methyl C) 6) mass spectrometry m / z 643 (M ⁺ )

(69) 16-epi-N-desethyl-N
-(4-methyl) pentyl-8-deoxy-14-O-
Physical properties and analytical data of anisoyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.94 (2H, d, J = 8.9 Hz) (same as above) 5.12 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (N- (H) of methyl of (4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 166.0 (C of anisoyl group carbonyl) 163.9, 131.7, 122.1, H3.4 (anisoyl group C) 91.3, 85.2, 83.5. 0.0,77.6,
76.0, 72.5, 71.9 (16, 6, 1, 14,
C, 18,13,15,3 position) 55.4 (methoxy C of anisoyl group) 62.2,59.1,57.8,56.0 (16,1
M, z 685 (M ⁺ ) 6) Mass spectrum analysis

(70) 16-epi-N-desethyl-N
-Acetyl-8-deoxy-14-O-anisoylaconine physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.94 (2H, d, J = 8.9 Hz) (same as above) 5.15 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy group H of anisoyl group) 2.34 (3H, s) (methyl of N-acetyl group) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.9 (C of carboxyl of N-acetyl group) 165.9 (C of carbonyl of anisoyl group) 163.6, 131.8, 113.7, 122.2 (C of anisoyl group) 91.2, 83, 7, 80.2, 79.8, 77.5,
76.0, 72.4, 72.0 (16, 6, 14, 1, 1
C, 18,13,15,3) 62.2,59.1,57.9,56.1 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 22.4 (N-acetyl methyl C) 6) mass spectrometry m / z 643 (M ⁺ )

(71) 16-epi-N-desethyl-N
-Benzoyl-8-deoxy-14-O-anisoylaconine physical properties and analytical data 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.82 to 7.10 (5H, m) (H of benzoyl group) 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.93 (2H, d, J = 8. 5.14 (1H, d, J = 5.0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9, 165.7 (C of carbonyl) 163.7, 131.7, 113.6, 122.1 (C of anisoyl group) 133.9, 133.5, 128.6, 128.2, 1
27.6 (C of benzoyl group) 91.3, 83.7, 80.1, 79.9, 77.5,
76.0, 72.4, 71.9 (16, 6, 14, 1, 1)
C, 18,13,15,3) 62.2,59.1,57.8,56.0 (16,1
8,6,1-position methoxy C) 55.4 (methoxy of anisoyl group) 6) mass spectrometry m / z 705 (M ⁺ )

(72) Physical properties and analytical data of 8-deoxy-14-OP-methoxybenzylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol It is soluble in ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.10 (2H, d, J = 8.9 Hz) (H of benzene ring of p-methoxybenzyl group) 6.73 (2H, d, J = 8.9 Hz) (same as above) 3.65 (3H) , S) (H of the methoxy group at positions 1, 6, 16 and 18) 3.39 (3H, s) (same as above) 3.31 (3H, s) (same as above) 3.28 (3H, s) (Same as above) 3.91 (3H, s) (H of methoxy group of p-methoxybenzyl group) 4.45 (2H, s) (H of methylene of p-methoxybenzyl group) 1.09 (3H, t) , J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 133.6, 128.2, 113.8, 157.7
(C of p-methoxybenzyl group) 64.0 (C of methylene of p-methoxybenzyl group) 93.7, 84.4, 83.2, 81.0, 77.4
77.2, 72.3, 72.0 (16, 6, 14, 1
C, 8,13,15,3) 60.2,59.1,58.1,56.0 (16,1
8,6,1-position methoxy group C) 55.8 (p-methoxybenzyl group methoxy group C) 49.4 (N-ethyl methylene C) 14.0 (N-ethyl methyl C) ) 6) mass spectroscopy ^{m / z 603 (M +)} 7) elemental analysis C ₃₃ H ₄₉ NO _9, calculated C: 65.65, H: 8.
18, N: 2.32 Actual value: C: 65.73, H: 8.29, N: 2.12

(73) Physical properties and analytical data of 8-deoxy-14-O-amyl aconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine It is soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.64 (3H, s) (H of the methoxy group at positions 1, 6, 16, and 18) 3.33 (3H, s) (same as above) 3.31 (3H, s) (same as above) 0.92 (3H, tJ = 7.4 Hz) (N-ethyl methyl H) 0.90 (3H, t, J = 10.1 Hz) (amyl group methyl) H) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of the group The following signals are shown (δ, ppm). 93.5, 84.6, 83.5, 81.2, 77.5,
77.2, 72.5, 72.1 (16, 6, 14, 1
C, 8,13,15,3) 60.5,59.1,58.0,55.6 (16,1
8,6,1-position methoxy group C) 49.4 (N-ethyl methylene C) 14.0 (N-ethyl methyl C) 13.5 (amyl methyl C) 5) Mass Spectrum analysis m / z 553 (M ⁺ ) 6) Elemental analysis C ₃₀ H ₅₁ NO ₈ , calculated value C: 65.07, H:
9.28, N: 2.53 Found C: 64.99, H: 9.35, N: 2.49

(74) Physical property values and analytical data of 8-deoxy-14-O-m-bromobenzoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1723 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 8.18-7.34 (4H, m) (H of m-bromobenzoyl group) 5.00 (1 H, d, J = 5.0 Hz) (14) ΒH at position 3.71 (3H, s) (H at 1, 6, 16 and 18-position methoxy groups) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.27 (3H, s) (same as above) 1.13 (3H, t, J = 7.1 Hz) (H of methyl in N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next The signal is shown (δ, ppm). 165.0 (C of m-bromobenzoyl carbonyl) 136.4, 136.1, 132.0, 130.1, 1
28.3,122.6 (C of m-bromobenzoyl) 94.1,85.1,83.5,81.0,77.2
75.1, 72.4, 71.9 (16, 6, 1, 14,
18,13,15,3 position C) 59.2,59.0,56.1 (C of methoxy group at 16,18,6,1 position) 49.2 (C of N-ethyl methylene) 13 .3 (of methyl N- ethyl C) 6) mass spectroscopy ^{m / z 665 (M +)} , 667 (M +) 7) elemental analysis C ₃₂ H ₄₄ NO _9, calculated C: 57.66, H :
6.65, N: 2.10 Found C: 57.48, H: 6.91, N: 2.00

(75) Physical property values and analytical data of 8-deoxy-14-O-m-fluorobenzoylaconin 1) Properties and solubility A colorless non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1725 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 7.95 to 7.40 (4H, m) (H of m-fluorobenzoyl group) 5.01 (1H, d, J = 5.1 Hz) (14) ΒH) 3.94 (3H, s) (H of 1,6,16 and 18-position methoxy groups) 3.32 (3H, s) (same as above) 3.31 (3H, s) (same as above) 3.19 (3H, s) (Id.) 1.26 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 164. 4 (C of m-fluorobenzoyl carbonyl) 160.5, 130.3, 130.2, 125.6, 1
20.5, 116.7 (C of m-fluorobenzoyl) 93.9, 84.9, 83.7, 80.6, 77.2.
75.0, 72.0, 71.8 (16, 6, 1, 14,
C, 18,13,15,3) 59.2,58.1,57.7,56.2 (16,1
8,6,1-position methoxy group C) 49.4 (N-ethyl methylene C) 12.8 (N-ethyl methyl C) 6) Mass spectrometry m / z 605 (M ⁺ ) 7 ) Elemental analysis C ₃₂ H ₄₄ NO ₉ , calculated C: 63.46, H:
7.32, N: 2.31 Found C: 63.41, H: 7.29, N: 2.41

(76) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O-veratroyl aconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.88-7.68 (3H, m) (H of veratroyl group) 5.20 (1H, t, J = 4.6 Hz) (βH at position 14) 3.92 (6H, s) (of veratroyl group) H of a methoxy group) 3.36 (3H, s) (H of a methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) ( 3.26 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 166.0 (C of vercarbonyl group carbonyl) 122.5, 110.5, 153.1, 148.2, 1
12.3 (C of veratroyl group) 93.0, 86.0, 85.1, 81.9, 78.4,
72.4 (C at position 16, 16, 6, 18, 14, 15) 55.8 (C of methoxy group of veratroyl group) 59.1, 58.7, 57.9, 56.0 (18, 1
6,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 6) Mass spectrometry m / z 615 (M ⁺ ) 7 ) Elemental analysis C ₃₄ H ₄₉ NO ₉ , calculated C: 66.32, H:
8.02, N: 2.27 Found C: 66.51, H: 7.96, N: 2.36

(77) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O-acetylaconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 5.05 (1 H, t, J = 5.0 Hz) (βH at position 14) 3.36 (3H, s) (positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.23 (3H, s) (same as above) 2.03 (3H, s) (H of methyl of acetyl group) 1.10 (3H, t, J = 7 Hz)) (H of methyl of N-ethyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signal is shown (δ , Ppm). 171.5 (C of carbonyl of acetyl group) 93.0, 86.0, 85.1, 81.7, 77.4,
72.4 (C at positions 16,1,6,18,14,15) 59.2,58.8,57.7,56.1 (18,1
6,6,1-position methoxy group C) 49.1 (N-ethyl ethylene C) 13.4 (N-ethyl methyl C) 21.4 (acetyl group methyl C) 5) Mass Spectrum analysis m / z 493 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₇ , calculated value C: 65.69, H: 8.
78, N: 2.84 Found C: 65.81, H: 8.67, N: 2.63

(78) 3,8,13-Trideoxy-1
Physical properties and analytical data of 4-O-m-chlorobenzoylaconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide And is insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.78-7.30 (5H, m) (H of m-chlorobenzoyl group) 5.06 (1H, tJ = 4.7 Hz) (βH at position 14) 3.51 (3H, s) (H at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3.28 (3H, s) s) (same as above) 3.25 (3H, s) (same as above) 1.12 (3H, t, J = 7.0 Hz) (H of methyl in N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) analysis shows the following signals (δ, ppm): 165.0 (C of carbonyl of m-chlorobenzoyl group) 131.6, 130.0, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 93.1, 86.0, 85.3, 82.0, 78.
3), 72.5 (C at positions 16, 16, 6, 18, 14, 15) 59.0, 58.7, 58.0, 56.0 (18, 1
6,6,1 position methoxy C) 49.2 (N-ethyl methylene C) 13.1 (N-ethyl methyl group C) 6) Mass spectrometry m / z 589, 591 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₄ NO ₇ Cl, calculated C: 65.13,
H: 7.51, N: 2.37 Found C: 65.41, H: 7.66, N: 2.1
4

(79) 3,8,13-Trideoxy-1
Physical property values and analytical data of 4-O-benzylaconine , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.29 (5H, s) (H of benzyl group) 4.48 (2H, s) (H of methylene of benzyl group) 3.47 (3H, s) (Methoxy group at 1,6,16 and 18th position) H) 3.31 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.09 (3H, t, J = 7.0 Hz) 5) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) analysis shows the following signals (δ, ppm): 126.3, 127.3, 128.0, 141.8 (C of benzyl group) 64.3 (C of methylene of benzyl group) 92.5, 86.1, 84.3, 82.0, 81. 1,
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.2, 58.0, 57.2, 56.0 (16, 6,
18,1 position C) 49.2 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 6) Mass spectrometry m / z 541 (M ⁺ ) 7) Elemental analysis C ₃₂ H ₄₇ NO ₆ , Calculated C: 70.95, H:
8.74, N: 2.5 Actual value C: 70.77, H: 8.84, N: 2.6

(80) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O- (4-methyl) pentylaconin 1) Property and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble and insoluble in hexane and water. 2) ¹ H Nuclear Magnetic Resonance Spectrum (CDCl ₃ ) analysis 3.50 (3H, s) (H of 1,6,16 and 18-position methoxy group) 3.37 (3H, s) (same as above) 3.28 (6H, s) (same as above) 1.10 (6H, t, J = 7.0 Hz) (methyl H of 4-methylpentyl) 3) ₁₃ C nucleus Magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 92.4, 86.0, 83.2, 80.3, 77.3
73.0 (C at position 16, 16, 6, 18, 14, 15) 59.2, 58.7, 57.9, 56.0 (18, 1
6,6,1-position C) 49.0 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 21.2 (4-methylpentyl methyl C) 4) Mass spectrum Analysis m / z 535 (M ⁺ ) 5) Elemental analysis C ₃₁ H ₅₃ NO ₆ , calculated C: 69.50, H:
9.97, N: 2.61 Found C: 69.76, H: 10.05, N: 2.4
6

(81) 3,8,13-Trideoxy-1
Physical property value and analytical data of 4-O-crotyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ₁ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.72 (2H, m) (H of crotyl group double bond) 4.08 (2H, m) (H of methylene of crotyl group) 3.51 (3H, s) (1, 6, 16 and 18) 3.40 (3H, s) (same as above) 3.28 (6H, s) (same as above) 1.71 (3H, d, J = 6.3 Hz) (methyl of crotyl group) H) 0.91 (3H, t, J = 7.3 Hz) (H of methyl N-ethyl) 4) ₁₃ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 130.8, 123.8 (C of double bond of crotyl group) 92.3, 86.2, 84.6, 81.5, 81.3
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.0, 58.1, 57.8, 55.8 (18, 6,
16, 1-position methoxy C) 49.4 (N-ethyl methylene C) 13.9 (N-ethyl methyl C) 12.6 (crotyl methyl C) 5) Mass spectrum Analysis m / z 505 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₆ , Calculated C: 68.88, H:
9.37, N: 2.7 Found C: 68.91, H: 9.36, N: 2.6

(82) 3,8-dideoxy-14-O-
Veratroyl aconin physical properties and analytical data 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.69-7.67 (3H, m) (H of veratroyl group) 5.07 (1H, d, J = 4.6 Hz) (β at position 14
H) 3.92 (6H, s) (H of methoxy group of veratroyl group) 3.53, 3.32, 3.29, 3.26 (each3
H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of carbonyl of veratroyl group) 122.6, 110.5, 153.1, 148.1, 1
12.3 (C of veratroyl group) 94.1, 86.0, 85.1, 80.3, 81.9,
75.3, 72, 4 (16, 1, 6, 14, 18, 1
(C at 3,15 position) 55.8 (C of methoxy of veratroyl group) 61.8, 59.0, 58.0, 56.0 (16, 1
M, z 631 (M ⁺ ) 7 C) 8,9,1-Methoxy group C) 49.0 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 6) Mass spectrum analysis ) Elemental analysis C ₃₄ H ₄₅ NO ₁₀ , Calculated C: 64.64, H:
7.82, N: 2.22 Found C: 64.83, H: 8.01, N: 2.08

(83) 3,8-dideoxy-14-O-
Physical properties and analytical data of acetylaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 4.95 (1 H, d, J = 5.0 Hz) (βH at position 14) 3.65 (3H, s) (positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (6H, s) (same as above) 2.06 (H of acetyl group methyl) 1.10 (3H, t, J) = 7.0 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 171.5 (C of carbonyl of acetyl group) 94.1, 85.4, 83.3, 80.2, 77.3
75.3, 72.4 (16, 1, 6, 18, 14, 1
C in position 3,15) 61.6,59.0,57.9,56.0 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) 21.6 (acetyl group methyl C) 5) Mass Spectrum analysis m / z 509 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₈ , calculated value C: 63.63, H: 8.
50, N: 2.75 Found C: 63.39, H: 8.71, N: 2.54

(84) 3,8-dideoxy-14-O-
Physical properties and analytical data of m-chlorobenzoyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.30 (5H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 4.7 Hz) (βH at position 14) 3.70 (3H, s) ( H of the methoxy group at the 1,6,16,18-position 3.32 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of carbonyl of m-chlorobenzoyl group) 131.5, 129.9, 129.5, 135, 0, 1
28.4 (C of m-chlorobenzoyl group) 94.4, 86.2, 85.0, 82.5, 80.3,
75.3, 72.6 (16, 1, 6, 18, 14, 1
31.8, C) 61.8, 59.1 58.1, 56.0 (16, 1
8,6,1-position methoxy group C) 49.1 (N-ethyl methylene C) 13.2 (N-ethyl methyl C) 6) Mass spectrometry m / z 605,607 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₄ NO ₈ Cl, calculated C: 63.41, H:
7.32, N: 2.31 Found C: 63.66, H: 7.51, N: 2.25

(85) 3,8-dideoxy-14-O-
Physical property values and analytical data of benzylaconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.47 (2H, s) (H of methylene of benzyl group) 3.65 (3H, s) (methoxy H at positions 1, 6, 16 and 18) 3.31 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.08 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (β, ppm). 126.3, 127.2, 128.3, 141.6
(C of benzyl group) 64.2 (C of benzyl group of methylene) 93.5,86.1,84.3,81.9,81.1,
77.3, 72.4 (16, 1, 6, 18, 14, 1
(C in 3,15th position) 60.2,59.1,58.0,56.0 (16,1
8,6,1-position methoxy group C) 49.2 (N-ethyl methylene C) 13.0 (N-ethyl methyl C) 6) Mass spectrometry m / z 557 (M ⁺ ) 7 ) Elemental analysis C ₃₂ H ₄₇ NO ₇ , calculated C: 68.91, H:
8.49, N: 2.51 Found C: 69.14, H: 8.69, N: 2.55

(86) 3,8-dideoxy-14-O-
Physical property value and analytical data of (4-methyl) pentylaconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 3.68 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.37 (3H, s) (ibid.) 28 (6H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 1.02 (6H, d, J = 7.0 Hz) (4- H) 3) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl of methylpentyl shows the following signals (δ, ppm) 93.4, 85.3, 83.2, 80.3, 77.4.
75.5, 72.4 (16, 1, 6, 18, 14, 1
30.3, C) 60.3, 59.0, 58.2, 56.0 (16, 1
Methoxy group C at 8,6,1 position 49.3 (N-ethyl methylene C) 13.8 (N-ethyl methyl C) 21.2 (4-methylpentyl methyl C) 4 ) Mass spectrometry m / z 551 (M ⁺ ) 5) Elemental analysis C ₃₁ H ₅₃ N ₇ , Calculated C: 67.48, H: 9.
68, N: 2.54 actual value: C: 67.21, H: 9.76, N: 2.22

(87) 3,8-dideoxy-14-O-
Physical property value and analytical data of crotyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water . 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.71 (2H, m) (H of the double bond of the crotyl group) 4.09 (2H, m) (H of the methylene of the crotyl group) 3.69 (3H, s) (1, 6, 16 and 18) 3.40 (3H, s) (same as above) 3.27 (6H, s) (same as above) 1.70 (3H, d, J = 6.3 Hz) (methyl of crotyl group) H) 0.89 (3H, t, J = 7.3 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 130.8, 123.7 (C of double bond of crotyl group) 93.5, 86.2, 84.6, 81.6, 81.3.
77.2, 72.4 (16, 1, 6, 18, 14, 1
39.5 position C) 49.5 (N-ethyl methylene C) 14.0 (N-ethyl methyl C) 12.7 (crotyl methyl C) 60.5, 59.0 , 58.1, 55.8 (16, 1
C) 8,8,1-position methoxy group C) 5) Mass spectrum analysis m / z 521 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₇ , Calculated C: 66.77, H:
9.08, N: 2.68 Found C: 66.91, H: 9.21, N: 2.55

(88) Physical properties and analytical data of 14-O-veratroyl aconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.89-7.68 (3H, m) (H of veratroyl group) 4.97 (1H, d, J = 5.0 Hz) (βH at position 14) 3.92 (6H, s) (of veratroyl group) Methoxy group H) 3.71 (3H, s) (methoxy group H at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) Top) 3.25 (3H, s) (same as above) 1.10 (3H, tJ = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next (Δ, ppm). 166.0 (C of the carbonyl of the veratroyl group) 122.5, 110.6, 153.1, 148.3, 1
12.3 (C of veratroyl group) 90.8, 83.5, 82.4, 81.9, 79.5
78.6, 77.3, 74.8, 71.9 (16, 6,
1,15,14,8,18,13,3-position C) 55.8 (verotroyl group methoxy group C) 60.9,59.1,58.0,55.6 (16,1
M, z 663 (M ⁺ ) 7) C (8,6,1-position methoxy group) 48.4 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) ) Elemental analysis C ₃₄ H ₄₉ NO ₁₂ , calculated C: 61.52, H:
7.44, N: 2.11 Found C: 61.80, H: 7.56, N: 2.09

(89) Physical properties and analytical data of 14-O-acetylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide Soluble in water, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.95 (1H, d, J = 4.8 Hz) (βH at position 14) 3.71 (6H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s 3.29 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.01 (3H, s) (H of methyl of acetyl group) 1.10 (3H) , TJ = 7.0 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 171.5 (C of carbonyl of acetyl group) 90.7, 83.5, 82.4, 79.9, 79.5
78.6, 77.3, 74.8, 71.9 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,58.0,55.6 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.3 (N-ethyl methyl C) 21.5 (acetyl methyl methyl C) 5) Mass Spectrum analysis m / z 541 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₁₀ , calculated value C: 59.87, H:
8.00, N: 2.59 Actual value: C: 60.05, H: 8.08, N: 2.44

(90) Physical properties and analytical data of 14-Om-chlorobenzoyl aconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.31 (5H, m) (H of m-chlorobenzoyl group) 4.89 (1H, d, J = 5.0 Hz) (βH at position 14) 3.71 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.24 (3H, s) (same as above) 1.02 (3H, tJ = 7.0 Hz) (H of methyl in N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 166.0 (C of carbonyl of m-chlorobenzoyl group) 131 .5,130.0,129.5,135.1,1
28.3 (C of m-chlorobenzoyl group) 90.7, 83.4, 82.3, 82.0, 79.4
78.6, 77.3, 74.7, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,57.9,55.6 (16,8,
6, methoxy group C at position 1) 48.8 (N-ethyl methylene C) 13.0 (N-ethyl methyl C) 6) Mass spectrometry m / z 637, 639 (M ⁺ ) 7 ) elemental analysis C ₃₂ H ₄₄ NO ₁₀ Cl, calculated C: 60.23,
H: 0.95, N: 2.19 Found C: 60.33, H: 7.11, N: 1.97

(91) Physical properties and analytical data of 14-O-benzylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide Soluble in water, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.50 (2H, s) (H of methylene of benzyl group) 3.70 (3H, s) (methoxy group at positions 1, 6, 16 and 18) H) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.09 (3H, t, J = 7) .0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 126.7, 127.0, 128.6, 141.7 (benzyl group C) 64.0 (benzyl group methylene C) 90.8, 83.4, 82.1, 81.9, 79. 5,
78.8, 77.3, 74.6, 71.9 (16, 6,
1, 15, 14, 8, 18, 13, 3rd position C) 60.9, 59.1, 57.9, 55.6 (16, 1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 6) Mass spectrometry m / z 589 (M ⁺ ) 7 ) Elemental analysis C ₃₂ H ₄₇ NO ₉ , calculated C: 65.17, H:
8.03, N: 2.38 Found C: 64.92, H: 7.97, N: 2.18

(92) Physical property values and analytical data of 14-O- (4-methyl) pentylaconine 1) Properties and solubility Colorless, non-solid powder, ether, chloroform, benzene, ethanol, methanol, acetic acid Soluble in ethyl, pyridine and dimethyl sulfoxide, insoluble in hexane and water. 2) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.70 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.09 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 1.02 (6H, d, J = 7.0 Hz) (4-methyl H) 3) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of pentyl methyl. The following signals are shown (δ, ppm). 90.8, 83.4, 82.1, 81.9, 79.5
78.9, 77.4, 74.5, 72.0 (16, 6,
1, 15, 14, 8, 18, 13, 3rd position C) 60.8, 59.0, 58.0, 55.5 (16, 1
8,6,1 position methoxy group C) 49.0 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 21.1 (4-methylpentyl methyl C) 4 ) mass spectrometry ^{m / z 583 (M +)} 5) elemental analysis C ₃₁ H ₅₃ NO _9, calculated C: 63.78, H:
9.15, N: 2.40 Found C: 63.61, H: 9.02, N: 2.36

(93) Physical properties and analytical data of 14-O-crotyl aconin 1) Properties and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.68 (2H, m) (H of the double bond of the crotyl group) 4.10 (2H, m) (H of the methylene of the crotyl group) 3.70 (3H, s) (1, 6, 16 and 18) 3.35 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.70 (3H, d) , J = 6.3 Hz) (H of crotyl group methyl) 0.90 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 130.7, 123.5 (C of crotyl group double bond) 90.7, 83.5, 82.3, 82.0, 79.4
78.8, 77.5, 74.6, 72.0 (16, 6,
1, 15, 14, 8, 18, 13, 3rd position C) 60.8, 59.0, 58.1, 55.6 (16, 1
Methoxy group C at 8,6,1 position 49.1 (N-ethyl methylene C) 13.9 (N-ethyl methyl C) 12.9 (crotyl group methyl group C) 5) Mass spectrum analysis m / z 553 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₉ , Calculated C: 62.91, H:
8.56, N: 2.53 Observed value C: 63.14, H: 8.44, N: 2.37

(94) 3,13-dideoxy-14-O
-Physical properties and analytical data of veratroyl aconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.89-7.70 (3H, m) (H of veratroyl group) 5.03 (1H, t, J = 4.8 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group H) 3.58 (3H, s) (H at positions 1, 6, 16 and 18) 3.29 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.21 (same as above) 3H, s) (Id.) 1.10 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown ( δ, ppm). 166.0 (C of carbonyl of veratroyl group) 122.7, 110.4, 153.2, 148.111
2.4 (C of veratroyl group) 89.7, 85.2, 83.6, 81.7, 79.9,
78.6, 77.5 (16, 1, 6, 18, 15, 8,
C at position 14) 55.8 (C of methoxy group of veratroyl group) 59.1, 57.9, 57.6, 55.6 (18, 1
6,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.2 (N-ethyl methyl C) 6) Mass spectrometry m / z 631 (M ⁺ ) 7 ) elemental analysis C ₃₄ H ₄₉ NO _10, calculated value C: 64.64, H:
7.82, N: 2.22 Found C: 64.45, H: 7.93, N: 2.21

(95) 3,13-dideoxy-14-O
-Physical property value and analytical data of acetylaconine Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.93 (1H, t, J = 4.8 Hz) (βH at position 14) 3.59 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) 3.27 (3H, s) (same as above) 3.21 (3H, s) (same as above) 2.02 (3H, s) (methyl H of acetyl group) 1.10 (3H) , T, J = 7.0 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 171.4 (C of carbonyl of acetyl group) 89.8, 85.2. 83.6, 81.7, 79.9,
78.6, 77.5 (16, 1, 6, 18, 15, 8,
14th C) 59.2, 57.8, 57.6, 55.5 (18, 1
6,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.2 (N-ethyl methyl C) 21.4 (acetyl group methyl C) 5) Mass Spectrum analysis m / z 509 (M ⁺ ) 6) elemental analysis C ₂₇ H ₄₃ NO ₈ , calculated value C: 63.63, H:
8.50, N: 2.7 Found C: 63.81, H: 8.65, N: 2.6

(96) 3,13-diteoxy-14-O
-Physical properties and analytical data of m-chlorobenzoyl aconine 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.95-7.28 (5H, m) (H of m-chlorobenzoyl) 5.01 (1H, t, J = 4.9 Hz) (βH at position 14) 3.59 (3H, s) (1 , H of the methoxy group at positions 6, 16, and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.21 (3H, s) (same as above) 1 .12 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.5 (carbonyl C of m-chlorobenzoyl group) 131.4, 130.0, 129.5, 135.1, 1
28.4 (C of m-chlorobenzoyl group) 89.6, 85.0, 83.6, 81.8, 80.0,
78.5, 77.5 (16, 1, 6, 18, 15, 8,
14th place C) 59.0, 57.8, 57.6, 55.6, (18,
16,6,1-position methoxy C) 49.1 (N-ethyl methylene C) 13.0 (N-ethyl methyl C) 6) Mass spectrometry m / z 605,607 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₄ NO ₈ Cl, calculated C: 63.41,
H: 7.32, N: 2.31 Actual value: C: 63.28, H: 7.55, N: 2.15

(97) 3,13-dideoxy-14-O
-Physical properties and analytical data of benzyl aconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.50 (2H, s) (H of methylene of benzyl group) 3.61 (3H, s) (methoxy group at position 1, 6, 16 and 18) H) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.09 (3H, t, J = 7) 0.0 Hz) (H of methyl N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 126.7, 127.0, 128.6, 141.6 (benzyl group C) 64.1 (benzyl group methylene C) 89.8, 85.3, 83.7, 81.8, 79. 7,
78.5, 77.4 (16, 1, 6, 18, 15, 8,
14th place C) 59.3, 58.0 57.6, 55.5 (18, 1
6,6,1 position methoxy C) 49.3 (N-ethyl methylene C) 14.0 (N-ethyl methyl C) 6) Mass spectrometry m / z 557 (M ⁺ ) 7) Elemental analysis: C ₃₂ H ₄₇ NO ₇ , calculated: C: 68.91, H:
8.49, N: 2.51 Found C: 68.76, H: 8.58, N: 2.42

(98) 3,13, dideoxy-14-O
Physical properties and analytical data of-(4-methyl) pentylaconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.61 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of methyl group of N-ethyl group) 1.02 (6H, t, J = 7.0 Hz) (4 -H) of methyl of methylpentyl 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 89.7, 85.2, 83.5, 81.7, 79.8,
78.6, 77.3 (16, 1, 6, 18, 15, 8,
14th place C) 59.3, 58.0, 57.6, 55.4 (18, 1
6,3,1 position methoxy group C) 49.3 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 21.3 (4-methylpentyl methyl) C) 5) mass spectrometry ^{m / z 551 (M +)} 6) elemental analysis C ₃₁ H ₅₃ NO _7, calculated C: 67.48, H:
9.68, N: 2.54 Found C: 67.66, H: 9.81, N: 2.32

(99) 3,13-dideoxy-14-O
-Physical properties and analytical data of crotyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, insoluble in hexane and water is there. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.68 (2H, m) (H of crotyl group double bond) 4.09 (2H, m) (H of methylene of crotyl group) 3.58 (3H, s) (1,6,16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.23 (3H, s) (same as above) 1.72 (3H, d) , J = 6.3 Hz) (H of methyl of crotyl group) 0.90 (3H, t, J = 7.0 Hz) (H of methyl group of N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 130.8, 123.6 (C of double bond of crotyl group) 89.7, 85.0, 83.5, 81.5, 79.8,
78.7, 77.5 (16, 1, 6, 18, 15, 8,
14th place C) 59.1, 58.1, 57.7, 55.6 (18, 1
6,2,1 position methoxy group C) 49.2 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 12.8 (crotyl group methyl C) 5) mass spectrometry ^{m / z 521 (M +)} 6) elemental analysis C ₂₉ H ₄₇ NO _7, calculated C: 66.77, H:
9.08, N: 2.68 Found C: 66.91, H: 9.15, N: 2.81

(100) Physical properties and analytical data of 3-deoxy-14-O-veratroyl aconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate , Soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.88-7.68 (3H, m) (H of veratroyl group) 4.98 (1H, d, J = 4.7 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group Methoxy group H) 3.70 (3H, s) (methoxy group H at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) Top) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃₎ ) Analysis The following signals are shown (δ, ppm). 165.9 (C of vercarbonyl group) 122.5, 110.5, 153.1 148.2, 1
12.3 (C of veratroyl group) 90.8, 85.2, 83.6, 81.9, 81.7,
79.5, 78.6, 74.8 (16, 1, 6, 1
5,5.8,14,8,13-position C) 55.8 (verotroyl group methoxy group C) 60.9,59.1,58.0,55.7 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.2 (N-ethyl group methyl C) 6) Mass spectrometry m / z 647 (M ⁺ 7) Elemental analysis C ₃₄ H ₄₉ NO ₁₁ , Calculated C: 63.04, H:
7.62, N: 2.16 Found C: 63.22, H: 7.59, N: 2.13

(101) Physical Properties and Analytical Data of 3-Deoxy-14-O-acetylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.96 (1H, d, J = 4.8 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) 3.29 (3H, s) (same as above) 3.24 (3H, s) (same as above) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 171.6 (C of carbonyl of acetyl group) 90.8, 85.2, 83.3, 81.8, 81.6,
79.5, 78.6, 74.8 (16, 1, 6, 15,
C, 18,14,8,13) 60.9,59.0,58.1,55.6 (16,1
8,6,1 position methoxy group C) 49.0 (N-ethyl group methylene C) 13.2 (N-ethyl group methyl C) 21.5 (acetyl group methyl C) 5 ) Mass spectrum analysis m / z 525 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₃ , calculated C: 61.70, H:
8.25, N: 2.66 Found: C: 61.79, H: 8.18, N: 2.48

(102) 3-Deoxy-14-Om-
Physical property values and analytical data of chlorobenzoyl aconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.30 (5H, m) (H of m-chlorobenzoyl group) 4.87 (1H, d, J = 5.0 Hz) (βH at position 14) 3.71 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.3 (C of carbonyl of m-chlorobenzoyl group) 131.5, 129.9, 129.4, 135.1, 1
28.4 (C of m-chlorobenzoyl group) 90.7, 85.2, 83.6, 82.0, 81.6
79.5, 78.6, 74.8 (16, 1, 6, 15,
C at positions 18, 14, 8, 13) 60.9, 59.2, 58.1, 55.6 (16, 1
Methoxy group C at 8,6,1 position) 49.1 (N-ethyl group methylene C) 13.0 (N-ethyl group methyl C) 6) mass spectrometry m / z 621,623 (M ⁺⁾ 7) elemental analysis C ₃₂ H ₄₄ NO ₃ Cl, calculated C: 61.78, H:
7.13, N: 2.25 Found C: 6
1.91, H: 7.32, N: 2.28

(103) Physical property values and analytical data of 3-deoxy-14-O-benzylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate It is soluble in pyridine, dimethylsulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ₁ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.49 (2H, s) (H of methylene of benzyl group) 3.70 (3H, s) (methoxy group at positions 1, 6, 16 and 18) H) 3.31 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.27 (3H, s) (same as above) 1.10 (3H, t, J = 7) 0.0 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 126.6, 127.0, 128.5, 141.7 (C of benzyl group) 64.0 (C of benzyl group of methylene) 90.8, 85.3, 83.7, 81.8, 81. 6,
79.5, 78.6, 74.9 (16, 1, 6, 15,
C at the position of 18, 14, 8, 13) 60.7, 59.1, 58.0, 55.6, (16, 1
8,6,1-position methoxy group C) 49.4 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 6) Mass spectrometry m / z 573 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₇ NO _8, calc c: 66.99, H:
8.26, N: 2.44 Found C: 67.15, H: 8.41, N: 2.38

(104) 3-Deoxy-14-O- (4
-Methyl) pentylaconine physical properties and analytical data 1) Properties and solubility A colorless, amorphous powder that is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethylsulfoxide and hexane. 2) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.71 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.09 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl group) 1.02 (6H, d, J = 7.0 Hz) (4 -H) of methyl of methylpentyl) 3) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 90.7, 85.4, 83.7, 81.7, 81.5,
79.2, 78.5, 74.8 (16, 1, 6, 15,
C at the position of 18, 14, 8, 13) 60.8, 59.1, 58.0, 55.5, (16, 1
8,6,1-position methoxy group C) 49.4 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 21.0 (4-methylpentyl methyl group C) ) 4) mass spectroscopy ^{m / z 567 (M +)} 5) elemental analysis C ₃₁ H ₅₃ NO _8, calculated C: 65.58, H:
9.41, N: 2.47 Found C: 65.61, H: 9.53, N: 2.38

(105) Physical property values and analytical data of 3-deoxy-14-O-crotyl aconine 1) Properties and solubility A colorless non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, It is soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.69 (2H, m) (H of double bond of crotyl group) 4.10 (2H, m) (H of methylene of crotyl group) 3.68 (3H, s) (1,6,16 and 18) 3.40 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.71 (3H, d) , J = 6.3 Hz) (H of crotyl group methyl) 0.89 (3H, t, J = 7.0 Hz) (H of N-ethyl group methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃₎ ) Analysis Shows the following signals (δ, ppm). 130.8, 123.6 (C of crotyl group double bond) 90.6, 85.0, 83.5, 82.0, 81.7,
79.5, 78.6, 74.8 (16, 1, 6, 15,
C at positions 18, 14, 8, 13) 60.9, 59.2, 57.9, 55.7, (16, 1
8,3,1-position methoxy group C) 49.3 (N-ethyl group methylene C) 13.9 (N-ethyl group methyl C) 12.7 (crotyl group methyl group C) ) 5) mass spectrometry ^{m / z 537 (M +)} 6) elemental analysis C ₂₉ H ₄₇ NO _8, calculated C: 64.78, H:
8.81, N: 2.60 Actual value: C = 64.51, H: 8.66, N: 2.39

(106) 16-epi-8-deoxy-1
Physical property value and analytical data of 4-O- (p-methoxy) benzylaconine 1) Property and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. Soluble, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.10 (2H, d, J = 8.9 Hz) (H of p-methoxybenzyl group) 6.71 (2H, d, J = 8.9 Hz) (same as above) 3.82 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.39 (3H, s) (same as above) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.91 (3H, s) (H of methoxy of benzyl group) 4.45 (2H, s) (H of methylene of benzyl group) 1.09 (3H, t, J = 7.0 Hz) (N-ethyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signal (δ, ppm): 133.6, 128.2, 113.8, 157.7 (benzyl group C) 64.0 (benzyl group methylene C) 90.3, 84.4, 83.2, 81.0, 77. 4,
77.2, 72.3, 72.0 (16, 6, 14, 1
C, 8,13,15,3) 60.2,59.1,58.1,56.0 (16,1
8,6,1-position methoxy group C) 55.8 (p-methoxybenzyl group methoxy group C) 49.4 (N-ethyl group methylene group C) 14.0 (N-ethyl group methyl group C) C) 6) Mass spectrum analysis m / z 603 (M ⁺ )

(107) 16-epi-8-deoxy-1
Physical property value and analytical data of 4-O-amyl aconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.82 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.33 (3H, s) (same as above) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 0.92 (3H, t, J = 7.4 Hz) (H of N-ethyl group methyl) 0.90 (3H, t, J = 10.1 Hz) (amyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 90.2, 84.6, 83.5, 81.2, 77.5,
77.2, 72.5, 72.1 (16, 6, 14, 1
C, 8,13,15,3) 60.5,59.1,58.0,55.6 (16,1
8,6,1-position methoxy group C) 49.4 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 13.5 (amyl group methyl group C) 5) Mass spectrum analysis m / z 553 (M ⁺ )

(108) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-veratroyl aconin 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.88-7.68 (3H, m) (H of veratroyl group) 5.20 (1H, t, J = 4.6 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group H of methoxy) 3.56 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of N-ethyl group methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of vercarbonyl group carbonyl) 122.5, 110.5, 153.1, 148.2, 1
12.3 (C of veratroyl group) 90.2, 86.0, 85.1, 81.9, 78.4,
72.4 (C at positions 16,1,6,18,14,15) 55.8 (C of methoxy of veratroyl group) 59.1,58.7,57.9,56.0 (18,1
6,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) Mass spectrometry m / z 615 (M ⁺ )

(109) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-m-chlorobenzoylaconine 1) Properties and solubility A colorless non-crystalline powder, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.30 (5H, m) (H of m-chlorobenzoyl group) 5.06 (1H, t, J = 4.7 Hz) (βH at position 14) 3.75 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.12 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of carbonyl of m-chlorobenzoyl group) 131.6, 130.0, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 90.1, 86.0, 85.3, 82.0, 78.3,
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.0, 58.7, 58.0, 56.0 (18, 1
6,6,1-position methoxy group C) 49.2 (N-ethyl group methylene C) 13.1 (N-ethyl group methyl C) 6) Mass spectrum analysis m / z 589, 591 ( M ⁺ )

(110) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform and benzene It is soluble in ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.29 (5H, s) (H of benzyl group) 4.48 (2H, s) (H of methylene of benzyl group) 3.68 (3H, s) (methoxy group at position 1, 6, 16 and 18) H) 3.31 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.09 (3H, t, J = 7.0 Hz) 5) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) analysis shows the following signals (δ, ppm): 126.3, 127.3, 128.0, 141.8 (benzyl group C) 64.3 (benzyl group methylene C) 90.0, 86.1, 84.3, 82.0, 81. 1,
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.2, 58.0, 57.2, 56.0 (18, 6,
16,1 position methoxy group C) 49.2 (N-ethyl group methylene C) 13.1 (N-ethyl group methyl C) 6) Mass spectrometry m / z 541 (M ⁺ )

(111) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-crotyl aconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol It is soluble in methanol, ethyl acetate, pyridine and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.72 (2H, m) (H of the double bond of the crotyl group) 4.08 (2H, m) (H of the methylene of the crotyl group) 3.73 (3H, s) (1, 6, 16 and 18) 3.40 (3H, s) (same as above) 3.28 (6H, s) (same as above) 1.71 (3H, d, J = 6.3 Hz) (methyl of crotyl group) H) 0.91 (3H, t, J = 7.3 Hz) (H of methyl of N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). . 130.8, 123.8 (C of double bond of crotyl group) 90.1, 86.2, 84.6, 81.5, 81.3
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.0, 58.1, 57.8, 55.8 (18, 6,
16, 1-position methoxy group C) 49.4 (N-ethyl group methylene C) 13.9 (N-ethyl group methyl C) 12.6 (crotyl group methyl group C) 5 ) Mass spectrum analysis m / z 505 (M ⁺ )

(112) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-veratroyl aconin 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, Soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 6.69-7.67 (3H, m) (H of veratroyl group) 5.07 (1H, d, J = 4.6 Hz) (βH at position 14) 3.92 (6H, s) (veratroyl group Methoxy H) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of N-ethyl group methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of veratroyl group carbonyl) 122.6, 110.5, 153.1, 148.1, 1
12.3 (C of veratroyl group) 90.1, 86.0, 85.1, 80.3, 81.9,
75.3, 72.4 (16, 1, 6, 14, 18, 1
(C at 3,15 position) 55.8 (C of methoxy group of veratroyl group) 61.8, 59.0, 58.0, 56.0 (16, 1)
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) Mass spectrometry m / z 631 (M ⁺ )

(113) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-m-chlorobenzoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 1) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98-7.30 (5H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 4.7 Hz) (βH at position 14) 3.85 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.11 (3H, t, J = 7.0 Hz) (H of methyl in N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.1 (C of carbonyl of m-chlorobenzoyl group) 131.5, 129.9, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 90.4, 86.2, 85.0, 82.5, 80.3,
75.3, 72.6 (16, 1, 6, 18, 14, 1
C in position 3,15) 61.8,59.1,58.1,56.0 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl group methylene C) 13.2 (N-ethyl group methyl C) 6) Mass spectrometry m / z 605,607 ( M ⁺ )

(114) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-benzylaconine 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol It is soluble in methanol, ethyl acetate, pyridine and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.28 (5H, s) (H of benzyl group) 4.47 (2H, s) (H of methylene of benzyl group) 3.83 (3H, s) (methoxy group at position 1, 6, 16 and 18) H) 3.31 (6H, s) (same as above) 3.28 (3H, s) (same as above) 1.08 (3H, t, J = 7.0 Hz) 5) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 126.3, 127.2, 128.3, 141.6 (benzyl group C) 64.2 (benzyl group methylene C) 90.0, 86.1, 84.3, 81.9, 81.9. 1,
77.3, 72.4 (16, 1, 6, 18, 14, 1
C at position 3,15) 60.2,59.1,58.0,56.0 (16,1
8,6,1-position methoxy group C) 49.2 (N-ethyl group methylene C) 13.0 (N-ethyl group methyl C) 6) Mass spectrometry m / 1 557 (M ⁺ )

(115) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-crotyl aconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol It is soluble in ethyl acetate, pyridine, and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.71 (2H, m) (H of the double bond of the crotyl group) 4.09 (2H, m) (H of the methylene of the crotyl group) 3.82 (3H, s) (1, 6, 16 and 18) 3.40 (3H, s) (same as above) 3.27 (6H, s) (same as above) 1.70 (3H, d, J = 6.3 Hz) (methyl of crotyl group) H) 0.89 (3H, t, J = 7.3 Hz) (H of N-ethyl group methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). . 130.8, 123.7 (C of the double bond of the crotyl group) 90.2, 86.2, 84.6, 81.6, 81.3.
77.2, 72.4 (16, 1, 6, 18, 14, 1
39.5 position C) 49.5 (N-ethyl group methylene C) 14.0 (N-ethyl group methyl C) 12.7 (crotyl group methyl group C) 60.5,59 0.0, 58.0, 55.8 (16, 1
C) of the methoxy group at the 8,6,1-position 5) Mass spectrometry m / z 521 (M ⁺ )

(116) Physical properties and analytical data of N-desethyl-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, Soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.95 (2H, d, J = 8.9 Hz) (same as above) 4.95 (1H, d, J = 5. 0 Hz)) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (Δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.4, 113.5, 122.2 (C of anisoyl group) 94.4, 86.2, 85.0, 82.5, 80. 1,
75.0, 72.3, (16, 1, 6, 18, 14, 1
C at position 3,15) 61.9, 59.1, 58.0, 56.0 (16, 1
8,6,1-position C of methoxy group) 55.4 (C of anisoyl group methoxy) 6) Mass spectrum analysis m / z 573 (M ⁺ ) 7) Elemental analysis C ₃₁ H ₄₃ NO ₉ , calculated value C : 64.9, H: 7.5
5, N: 2.44 Actual value: C: 64.85, H: 7.41, N: 2.22

(117) N-desethyl-N-amyl-
Physical property value and analytical data of 3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.93 (2H, d, J = 8.9 Hz) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (6H, s) (H of methoxy group at anisoyl group) 3.69 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 0.99 (3H, t, J = 7.0 Hz) (N− H) 5) ₁₃ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of the methyl of the amyl group. The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.8, 113.6, 122.1 (C of anisoyl group) 94.2, 86.0, 85.1, 82.3, 80. 2,
75.1, 72.4 (16, 1, 6, 18, 14, 1
(C at 3,15 position) 55.4 (C of methoxy group of anisoyl group) 61.8, 59.1, 57.8, 56.0, (16, 1)
8,6,1-position methoxy group C) 13.1 (N-amyl group methyl C) 6) Mass spectrometry m / z 643 (M ⁺ )

(118) Physical property values and analytical data of N-desethyl-N-propyl-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder containing ether, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ³ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.94 (2H, d, J = 8.9 Hz) (same as above) 4.94 (1H, d, J = 5. 0 Hz)) (βH at position 14) 3.69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) s) (same as above) 3.24 (3H, s) (same as above) 3.87 (3H, s) (H of methyl of anisoyl group) 1.10 (3H, t, J = 7.0 Hz) (propyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm). 165.9 (C of anisoyl group carboxyl) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 94.3, 86.2, 85.0, 82.1, 80. 1,
75.3, 72.2 (16, 1, 6, 18, 14, 1
C at 3 and 15) 61.8, 59.0, 58.0, 56.0 (16, 1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) mass spectrometry m / z 615 (M ⁺ ) 7) elemental analysis C ₃ H ₄₉ NO _9, calculated C: 66.32, H: 8.0
2, N: 2.27 Found C: 66.45, H: 7.98, N: 2.20

(119) Physical properties and analytical data of N-desethyl-N- (4-methylpentyl) -3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline It is a powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.94 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.88 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.02 (6H, d, J = 7.0 Hz) (N− (H of methyl of 4-methylpentyl) 5) 13 C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.9, 131.7, 113.4, 122.1 (C of anisoyl group) 94.3, 86.1, 85.0, 82.2, 80. 1,
75.1, 72.3 (16, 1, 6, 18, 14, 1
C at 3 and 15) 61.8, 59.0, 57.9, 56.0 (16, 1
C, 55.4 of methoxy group at 8,6,1 position (C of methoxy of anisoyl group) 21.5 (C of methyl of N- (4-methylpentyl)) 6) Mass spectrum analysis m / z 657 (M ⁺ ) 7) Elemental analysis C ₃₇ H ₅₅ NO ₉ , calculated C: 67.55, H: 8.
43, N: 2.13 Found C: 67.38, H: 8.29, N: 226

(120) Physical property values and analytical data of N-desethyl-N-acetyl-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder containing ether, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 4.95 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 3.69 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.30 (3H, s) (H of methyl of N-acetyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 171.0 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 163.7, 131.6, 113.5, 122.1 (C of anisoyl group) 94.4, 85.0 , 82.5, 82.3, 80.2,
75.1, 72.3 (16, 6, 18, 1, 14, 1
C at position 3,15) 61.9, 59.1, 58.0, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N acetyl group methyl C) 6) Mass spectrometry m / z 615 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₅ NO _10, calculated value C: 64.37, H:
7.37, N: 2.27 Found: C: 64.52, H: 7.16, N: 2.25

(121) Physical property values and analytical data of N-desethyl-N-benzoyl-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder containing ether, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.81, 7.09 (5H, m) (H of benzoyl group) 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8. 9) (same as above) 4.93 (1H, d, J = 5.0 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8, 166.0 (C of carbonyl) 163.8, 131.7, 113.6, 122.0 (C of anisoyl group) 133.9, 133.4, 128.6, 128.2, 1
27.6 (C of benzoyl group) 94.3, 85.0, 82.4, 82.0, 80.3,
75.0, 72.5 (16, 6, 18, 1, 14, 1
C at 3 and 15) 61.8, 59.1, 57.8, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 677 (M ⁺ ) 7) elemental analysis C ³⁸ H ₄₇ NO ₁₀ , calculated value C : 67.34, H:
6.99, N: 2.07 Found C: 67.46, H: 7.08, N: 2.01

(122) N-desethyl-3,8,13
-Physical properties and analytical data of -trideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder that can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis Shows absorption maximum at 1715 cm ^-1 3) Ultraviolet absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d) , J = 8.9) (same as above) 5.08 (1H, t, J = 4.8 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 3.70 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9, 166.0 (C of carbonyl) 163.7, 131.6, 113.4, 122.2 (C of anisoyl group) 94.5, 86.3, 84.9, 82.5, 80 .2,
72.5 (C at position 16, 16, 6, 18, 14, 15) 59.1, 58.7, 57.9, 56.0 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrum analysis m / z 557 (M ⁺ ) 7) elemental analysis C ₃₁ H ⁴³ NO ₈ , calculated value C : 66.77, H: 7.
77, N: 2.51 Found C: 66.70, H: 7.64, N: 2.48

(123) N-desethyl-N-amyl-
Physical property values and analytical data of 3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d) , J = 8.9) (same as above) 5.09 (1H, t, J = 4.8 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 3.69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) s) (same as above) 0.98 (3H, t, J = 7.0 Hz) (H of N-amyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm). 166.0 (C of carbonyl) 163.7, 131.8, 113.6, 122.1 (C of anisoyl group) 94.1, 85.9, 85.1, 82.3, 80.2,
72.3 (C at 16,1,6,18,14,15th position) 59.2,58.8,57.9,56.0 (18,1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.2 (N-amyl methyl C) 6) Mass spectrometry m / z 627 (M ⁺ ) 7) Elemental analysis C ₃₆ H ₅₃ NO ₈ , Calculated value C: 68.87, H: 8.
51, N: 2.23, measured C: 68.92, H: 8.50, N: 2.18

(124) Physical properties and analytical data of N-desethyl-N-propyl-3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.06 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl) ₃ ) Analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 94.3, 86.2, 85.1, 82.0, 80.1,
72.1 (C at positions 16,1,6,18,14,15) 59.2,58.8,57.9,56.0 (18,1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-amyl methyl C) 6) Mass spectrometry m / z 599 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₅ NO ₈ , calculated value C: 68.09, H: 8.
23, N: 2.34 Actual value: C: 68.17, H: 8.35, N: 2.30

(125) N-desethyl-N- (4-methyl) pentyl-3,8,13-trideoxy-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.95 (2H, d, J = 8.9 Hz) (same as above) 5.10 (1H, t, J = 4. 8 Hz)) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) s) (same as above) 3.25 (3H, s) (same as above) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (N -5) ¹³ C nuclear magnetic resonance spectrum (CDCl ³ ) analysis of methyl of -4-methylpentyl. The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.7, 113.4, 122.0 (C of anisoyl group) 94.3, 86.1, 85.0, 82.2, 80. 1,
72.5 (C at positions 16,1,6,18,14,15) 59.3,58.8,57.9,56.0 (18,1
C, 6,6- and 1-methoxy group) 55.4 (M, anisoyl group C) 21.5 (M, C of N-4-methylpentyl) 6) Mass spectrometry m / z 641 (M ⁺ ) 7) elemental analysis C ₃₇ H ₅₅ NO _8, calculated C: 69.24, H: 8.
64N: 2.18 found C: 69.46, H: 8.53, N: 2.09

(126) Physical properties and analytical data of N-desethyl-N-acetyl-3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.08 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.30 (3H, s) (H of methyl of N-acetyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.9 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 163.7, 131.6, 113.4, 122.2 (C of anisoyl group) 94.5, 84.9 , 82.5, 81.9, 80.2,
72.4 (C at positions 16, 6, 18, 1, 14, 15) 59.1, 58.7, 57.9, 56.0 (18, 1
C, 6,6- and 1-position methoxy group) 55.4 (Methoxy C of anisoyl group) 21.0 (C of N-acetyl methyl) 6) Mass spectrometry m / z 599 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₅ NO _9, calculated C: 66.09, H: 7.
56, N: 2.34 Actual value: C: 65.87, H: 7.43, N: 2.28

(127) Physical property values and analytical data of N-desethyl-N-benzoyl-3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDC ₃ ) analysis The following signals are shown (δ, ppm). 7.82, 7.09 (5H, m) (H of benzoyl group) 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d, J = 8. 9) (same as above) 5.06 (1H, t, J = 4.8 Hz) (βH at position 14) 3.88 (3H, s) (methoxy H of anisoyl group) 3.69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0, 165.8 (C of carbonyl) 163.8, 131.7, 113.6, 122.0 (C of anisoyl group) 133.9, 133.4, 128.6, 128.2 (benzoyl Group C) 94.2, 85.0, 82.4, 81.8, 80.3,
72.6 (C at positions 16, 6, 18, 1, 14, 15) 59.2, 58.8, 57.9, 56.0 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 661 (M ⁺ ) 7) elemental analysis C ₃₈ H ₄₇ NO ₉ , calculated value C : 68.97, H: 7.
16, N: 2.1 found C: 69.11, H: 7.02, N: 2.3

(128) Physical property values and analytical data of N-desethyl-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate , Soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 166.0 (C of carbonyl) 163.6, 131.8, 113.7, 122.2 (C of anisoyl group) 90.8, 83.6, 82.4, 81.9, 79.5
78.6, 77.3, 74.7, 72.0 (16, 6,
1, 15, 14, 8, 18, 13, 3rd position C) 60.9, 59.1, 58.0, 55.6 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 605 (M ⁺ ) 7) elemental analysis C ₃₁ H ₄₃ NO ₁₁ , calculated value C : 61.47, H:
7.16, N: 2.31 Found C: 61.45, H: 7.02, N: 2.28

(129) N-desethyl-N-amyl-
Physical property value and analytical data of 14-O-anisoylaconine 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 4.98 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18) 3.30 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 0.98 (3H, t, J = 7.0 Hz) (N− Amyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl) 163.9, 131.7, 113.4, 122.1 (C of anisoyl group) 91.1, 83.5, 82.5, 81.9, 79.6, 79.6
78.6, 77.3, 74.8, 71.9 (16, 6,
1,15,14,8,18,13,3rd position C) 61.9,59.0,57.8,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.1 (N-amyl methyl C) 6) Mass spectrometry m / z 675 (M ⁺ ) 7) Elemental analysis: C ₃₆ H ₅₃ NO ₁₁ , calculated: C: 63.98, H:
7.90, N: 2.07 Found C: 64.10, H: 8.08, N: 2.03

(130) Physical Properties and Analytical Data of N-Desethyl-N-propyl-14-O-anisoylaconine 1) Properties and Solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.69 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (N− H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of propyl methyl The following signals are shown (δ, ppm). 166.0 (C of carbonyl) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 90.8, 83.6, 82.3, 81.8, 79.5
78.6, 77.3, 74.8, 71.9 (16, 6,
1,15,14,8,18,13,3rd position C) 61.8,59.1,58.0,56,1 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) Mass spectrometry m / z 647 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₃ NO ¹¹ , Calculated C: 63.04, H:
7.62, N: 2.16 Found C: 62.98, H: 7.66, N: 2.15

(131) Physical properties and analytical data of N-desethyl-N- (4-methyl) pentyl-14-O-anisoylaconine 1) Properties and solubility It is soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (N- (H) of methyl of (4-methylpentyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl) 163.9, 131.7, 113.4, 122.1 (C of anisoyl group) 90.8, 83.5, 82.4, 81.8, 79.5
78.6, 77.3, 74.8, 71.9 (16, 6,
1,15,14,8,18,13,3rd position C) 61.8,59.1,57.8,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.5 (N- (4-methylpentyl) methyl C) 6) mass spectrometry m / z 689 ( M ⁺⁾ 7) elemental analysis C ₃₇ H ₅₅ NO _11, calculated value C: 64.42, H:
8.04, N: 2.03 Found C: 64.55, H: 8.16, N: 2.11

(132) Physical property values and analytical data of N-desethyl-N-acetyl-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ₁ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.70 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 2.32 (3H, s) (H of methyl N-acetyl) 5) ¹ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.8 (C of acetyl group carbonyl) 166.0 (C of anisoyl group carbonyl) 163.6, 131.8, 113.7, 122.2 (C of anisoyl group) 90.8, 83.6 , 81.9, 79.8, 79.5,
78.6, 77.3, 74.8, 71.9 (16, 6,
15,1,14,8,18,13,3rd position C) 60.9,59.1,58.0,55.6 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.1 (N-acetyl methyl C) 6) Mass spectrometry m / z 647 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₅ NO _12, calculated value C: 61.19, H:
7.00, N: 2.16 Found C: 61.26, H: 7.21, N: 2.21

(133) Physical Properties and Analytical Data of N-Desethyl-N-benzoyl-14-O-anisoylaconine Soluble in methanol, ethyl acetate, pyridine, dimethylsulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.82 to 7.10 (5H, m) (H of benzoyl group) 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8. 9) (Id.) 4.97 (1H, d, J = 5.0 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0, 165.7 (C of carbonyl) 163.7, 131.7, 113.5, 122.1 (C of anisoyl group) 134.0, 133.6, 128.7, 128.2, 1
27.6 (C of benzoyl group) 91.0, 83.5, 81.9, 79.9, 79.6,
78.6, 77.3, 74.8, 71.9 (16,
6,15,1,14,8,18,13,3rd position C) 61.8,59.1,57.8,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrum analysis m / z 709 (M ⁺ ) 7) elemental analysis C ₃₈ H ₄₇ NO ₁₂ , calculated value C : 64.30, H:
6.67, N: 1.97 Found C: 63.19, H: 6.62, N: 2.08

(134) Physical Properties and Analytical Data of N-Desethyl-3-deoxy-14-O-anisoylaconine 1) Properties and Solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.95 (2H, d, J = 8.9 Hz) (same as above) 4.97 (1H, d, J = 5. 0 Hz)) (βH at position 14) 3.69 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (Δ, ppm). 166.0 (C of anisoyl group) 163.7, 131.6, 113.5, 122.1 (C of anisoyl group) 90.7, 85.3, 83.6, 81.2, 80. 0,
79.5, 78, 6, 75.0 (16, 1, 6, 18,
(C at 15, 14, 8, 13th position) 61.9, 59.1, 58.0, 56.0 (16, 1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 589 (M ⁺ ) 7) elemental analysis C ₃₁ H ₄₃ NO ₁₀ , calculated value C : 63.14, H:
7.35, N 2.38 Found C: 63.31, H: 7.26, N: 2.31

(135) N-desethyl-N-amyl-
Physical property value and analytical data of 3-deoxy-14-O-anisoylaconine 1) Property and solubility A colorless non-crystalline powder, which can be used in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine and dimethyl sulfoxide. Soluble, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.93 (2H, d, J = 8.9 Hz) (same as above) 4.98 (1H, d, J = 5. 0 Hz)) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.27 (3H, s) s) (same as above) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 0.99 (3H, t, J = 7.0 Hz) (N -H) of amyl methyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.8, 113.6, 122.1 (C of anisoyl group) 90.8, 85.4, 83.5, 81.0, 80. 0,
79.4, 78.6, 75.0 (16, 1, 6, 18,
(C at 15, 14, 8, 13th position) 61.8, 59.1, 57.8, 56.0 (16, 1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 13.1 (N-amyl methyl C) 6) mass spectrometry m / z 659 (M ⁺ ) 7) Elemental analysis: C ₃₆ H ₅₃ NO ₁₀ , calculated: C: 65.53, H:
8.10, N: 2.12 Found C: 65.44, H: 8.15, N: 2.10

(136) Physical property values and analytical data of N-desethyl-N-propyl-3-deoxy-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder containing ether, chloroform, It is soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, and dimethyl sulfoxide, and is insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.98 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (N− H) 5) ₁₃ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl propyl group The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 90.8, 85.4, 83.3, 81.0, 79. 9,
79.5, 78.6, 75.0 (16, 1, 6, 18,
C at position 15, 14, 8, 13) 61.7, 59.0, 58.0, 56.1 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) mass spectrometry m / z 631 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₉ NO _10, calculated value C: 64.64, H:
7.82, N: 2.22 Found C: 64.73, H: 7.66, N: 2.18

(137) Physical Properties and Analytical Data of N-Desethyl-N- (4-methyl) pentyl-3-deoxy-14-O-anisoylaconine 1) Properties and Solubility A colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.97 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.88 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.01 (6H, t, J = 7.0 Hz) (N- (H) of methyl of (4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.9, 131.7, 113.4, 122.1 (C of anisoyl group) 90.7, 85.5, 83.5, 81.0, 79. 9,
79.5, 78.6, 75.0 (16, 1, 6, 18,
(C at 15, 14, 8, 13th position) 61.8, 59.0, 58.0, 56.1 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.5 (N- (4-methyl) pentyl methyl C) 6) mass spectrometry m / z 673 ( M ⁺⁾ 7) elemental analysis C ₃₇ H ₅₅ NO _10, calculated value C: 65.95, H:
8.23, N: 2.08 Found C: 66.10, H: 8.18, N: 1.96

(138) Physical property values and analytical data of N-desethyl-N-acetyl-3-deoxy-14-O-anisoylaconine 1) Properties and solubility Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 4.97 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.69 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.31 (3H, s) (H of methyl of N-acetyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.8 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 163.7, 131.6, 113.5, 122.1 (C of anisoyl group) 90.7, 83.6 , 82.0, 81.2, 80.0,
79.5, 78.6, 75.0 (16, 6, 1, 18,
(C at 15, 14, 8, 13th position) 61.9, 59.1, 58.0, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (3H, s) (acetyl group methyl C) 6) Mass spectrometry m / z 631 (M ⁺ ) 7) Elemental analysis C ₃₃ H ₄₅ NO ₁₁ , Calculated C: 62.74, H:
7.18, N: 2.22 actual value C: 62.91, H: 7.22, N: 2.36

(139) Physical Properties and Analytical Data of N-Desethyl-N-benzoyl-3-deoxy-14-O-anisoylaconine 1) Properties and solubility Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.81 to 7.09 (5H, m) (H of benzoyl group) 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8. 9) (same as above) 4.96 (1H, d, J = 5.0 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 166.0, 165.8 (C of carbonyl) 163.8, 131.7, 113.6, 122.0 (C of anisoyl group) 133.9, 133.4, 128.6, 128.2, 1
27.6 (C of benzoyl group) 90.7, 83.6, 82.0, 81.0, 79.9,
79.5, 78.6, 75.0 (16, 6, 1, 18,
(C at 15, 14, 8, 13th position) 61.8, 59.1, 57.8, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 693 (M ⁺ ) 7) elemental analysis C ₃₈ H ₄₇ NO ₁₁ , calculated value C : 65.79, H:
6.83, N: 2.02 Found C: 65.81, H: 6.91, N: 2.15

(140) Physical properties and analytical data of N-desethyl-3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, Soluble in ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.05 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.70 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 166.0 (C of anisoyl group) 163.7, 131.6, 122.1, 113.3 (C of anisoyl group) 89.7, 83.6, 82.3, 81.7, 79. 9,
78.6, 77.4 (16, 6, 1, 18, 15, 8,
14th place C) 59.1, 57.9, 57.6, 55.9 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 557 (M ⁺ ) 7) elemental analysis C ₃₁ H ₄₃ NO ₉ , calculated value C : 64.98, H: 7.
55, N: 2.44 Found: C: 65.02, H: 7.68, N: 2.35

(141) N-desethyl-N-amyl-
Physical properties and analytical data of 3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 5.8 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.67 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.27 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (N- H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of amyl methyl. The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.7, 131.8, 113.6, 122.1 (C of anisoyl group) 89.8, 85.3, 83.5, 81.5, 81.6, 79. 9,
78.6, 77.4 (16, 1, 6, 18, 15, 8,
14th C) 59.1, 57.9, 57.5, 55.9 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.2 (N-amyl methyl C) 6) mass spectrometry m / z 643 (M ⁺ ) 7) Elemental analysis: C ₃₆ H ₅₃ NO ₉ , calculated: C: 67.16, H: 8.
30, N: 2.18 found C: 67.33, H: 8.18, N: 2.07

(142) Physical properties and analytical data of N-desethyl-N-propyl-3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.09 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.67 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl) ₃ ) Analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 113.7, 122.2 (C of anisoyl group) 89.8, 85.3, 83.4, 81.4, 79. 8,
78.6, 77.4 (16, 1, 6, 18, 15, 8,
14th place C) 59.1, 57.9, 57.5, 55.6 (18, 1
6,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) Mass spectrometry m / z 615 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₃ NO _9, calculated C: 66.32, H: 8.
02, N: 2.27 Found C: 66.46, H: 8.14, N: 2.33

(143) Physical properties and analytical data of N-desethyl-N- (4-methyl) pentyl-3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline It is a powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.10 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.68 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) ) (Same as above) 3.24 (3H, s) (same as above) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (N- (H) of methyl of (4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.9, 131.8, 113.4, 122.0 (C of anisoyl group) 89.8, 85.2, 83.4, 81.5, 79. 9,
78.6, 77.4 (16, 1, 6, 18, 15, 8,
14th C) 59.1, 57.9, 57.5, 55.9 (18, 1
6,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.5 (N- (4-methyl) pentyl methyl C) 6) Mass spectrometry m / z 657 ( M ⁺⁾ 7) elemental analysis C ₃₇ H ₅₅ NO _9, calculated C: 67.55, H: 8.
43, N: 2.13 Found C: 67.58, H: 8.49, N: 2.02

(144) Physical properties and analytical data of N-desethyl-N-acetyl-3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.95 (2H, d, J = 8.9 Hz) (same as above) 5.05 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 2.30 (3H, s) (H of methyl N-acetyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm) 170.8 (C of acetyl group carbonyl) 166.0 (C of anisoyl group carbonyl) 163.7, 131 6,122.1,113.3 (C of anisoyl group) 89.7,83.6,8 2.0, 81.7, 79.9,
78.6, 77.4 (16, 6, 1, 18, 15, 8,
14th place C) 59.1, 57.9, 57.6, 55.9 (18, 1
6,5.4, C of methoxy group at position 1) 55.4 (C of methoxy of anisoyl group) 21.0 (C of N-acetyl methyl) 6) Mass spectrometry m / z 615 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₅ NO _10, calculated value C: 64.37, H:
7.37, N: 2.27 Found: C: 64.09, H: 7.56, N: 2.16

(145) Physical properties and analytical data of N-desethyl-N-benzoyl-3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility It is soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.82, 7.09 (5H, m) (H of benzoyl group) 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d, J = 8. 9) (Same as above) 5.06 (1H, t, J = 4.8 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 3.68 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0, 165.8 (C of carbonyl) 163.8, 131.7, 122.0, 113.6 (C of anisoyl group) 133.9, 133.5, 128.6, 128.2 (benzoyl Group C) 89.8, 83.5, 82.0, 81.6, 79.9,
78.6, 77.4 (16, 6, 1, 18, 15, 8,
14th place C) 59.1, 57.9, 57, 6, 55.9 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrum analysis m / z 677 (M ⁺ ) 7) elemental analysis C ₃₈ H ₄₇ NO ₁₀ , calculated value C : 67.34, H:
6.99, N: 2.07 Found C: 67.52, H: 7.20, N: 2.13

(146) N-desethyl-16-epi-
Physical property value and analytical data of 3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 89) (H of anisoyl group) 6.95 (2H, d, J = 89) (same as above) 5.14 (1H, d, J = 5.0 Hz) (14) ΒH) 3.87 (3H, s) (methoxy H of anisoyl group) 3.84 (3H, s) (H of methoxy group at 1, 6, 16 and 18) 3.30 (3H, s) ) (Same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group carbonyl) 163,8,131.4,113.5,122.2 (C of anisoyl group) 91.2,86.2,85.0,82.5,80. 1,
76.0, 72.3 (16, 1, 6, 18, 14, 1
C at 3 and 15) 62.2, 59.1, 58.0, 56.0 (16, 1
M, z 557 (M ⁺ )

(147) N-desethyl-N-amyl-
Physical property value and analytical data of 16-epi-3,8-dideoxy-14-O-anisoylaconine 1) Property and solubility Colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate It is soluble in pyridine, dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 5.14 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.83 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 0.99 (3H, t, J = 7.0 Hz) (N− Amyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.8, 113.6, 122.1 (C of anisoyl group) 91.2, 86.0, 85.1, 82.3, 80. 2,
76.0, 72.4 (16, 1, 6, 18, 14, 1
C at position 3,15) 62.2,59.1,57.8,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.1 (3H, t, J = 7.0 Hz) (N-amyl methyl C) 6) Mass spectrum Analysis m / z 655 (M ⁺ )

(148) Physical properties and analytical data of N-desethyl-N-propyl-16-epi-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.13 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.83 (3H, s) (H at methoxy group at 1,6,16 and 18 position) 3.30 (3H, s) (same as above) 3.29 (3H, s) (same as above) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (N− H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl propyl. The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 91.3, 86.2, 85.0, 82.1, 80. 1,
76.1, 72.2 (16, 1, 6, 18, 14, 1
C, 3,15) 62.1,59.0,58.0,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) Mass spectrometry m / z 627 (M ⁺ )

(149) N-desethyl-N- (4-methyl) pentyl-16-epi-3,8-dideoxy-1
Physical property value and analytical data of 4-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.12 (1H, t, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3, 27 (3H, s) 3.25 (3H, s) (same as above) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (N- H) of methyl of (4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 166.0 (C of anisoyl group carbonyl) 163.9, 131.7, 113.4, 122.1 (C of anisoyl group) 91.3, 86.1, 86.0, 82.2, 8 0.1,
76.1, 72.3 (16, 1, 6, 18, 14, 1
C at position 3,15) 62.2,59.0,57.9,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.5 (N- (4-methyl) pentyl methyl C) 6) mass spectrometry m / z 669 ( M ⁺ )

(150) Physical properties and analytical data of N-desethyl-N-acetyl-16-epi-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol)

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.14 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group at anisoyl group) 3.84 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.28 (3H, s) (same as above) 3.25 (3H, s) (same as above) 2.30 (3H, s) (H of methyl of N-acetyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.8 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 163.7, 131.6, 113.5, 122.1 (C of anisoyl group) 91.2, 85.0 , 82.5, 82.0, 80.2,
76.1, 72.3 (16, 6, 18, 1, 14, 1
C at 3 and 15) 62.2, 59.1, 58.0, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N-acetyl methyl C) 6) mass spectrometry m / z 615 (M ⁺ )

(151) Physical property values and analytical data of N-desethyl-N-benzoyl-16-epi-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder It is soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.81 to 7.09 (5H, m) (H of benzoyl group) 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8. 9) (Same as above) 5.14 (1H, d, J = 5.0 HZ) (βH at position 14) 3.83 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0, 165.8 (C of carbonyl) 163.8, 131.7, 113.6, 122.0 (C of anisoyl group) 133.9, 133.4, 128.6, 128.2, 1
27.6 (C of benzoyl group) 91.3, 85.0, 83.4, 82.0, 80.3,
76.0, 72.5 (16, 6, 18, 1, 14, 1
C at position 3,15) 62.2,59.1,57.8,56.0 (16,1
M, z 678 (M ⁺ )

(152) N-desethyl-16-epi-
Physical property values and analytical data of 3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.96 (2H, d, J = 8.9 Hz) (same as above) 5.20 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.82 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, pm). 165.9 (C of anisoyl group) 163.7, 131.6, 113.4, 122.2 (C of anisoyl group) 91.2, 86.3, 84.9, 82.5, 80. 2,
72.5 (C at 16,1,6,18,14,15th position) 60.1,58.7,57.9,56.0 (18,1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) mass spectrometry m / z 541 (M ⁺ )

(153) N-desethyl-N-amyl-
16-epi-3,8,13-trideoxy-14-O-
Physical properties and analytical data of anisoyl aconin 1) Properties and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.93 (2H, d, J = 8.9) (same as above) 5.20 (1H, t, J = 5. 0 Hz) (βH at position 14) 3,87 (3H, s) (H of methoxy group of anisoyl group) 3.84 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 3.31 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 0.98 (3H, t, J = 7.0 Hz) (N− Amyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.7, 131.8, 122.1, 113.6 (C of anisoyl group) 91.4, 85.9, 85.1, 82.3, 80. 2,
72.3 (C at positions 16,1,6,18,14,15) 60.2,58.8,57.9,56.0 (18,1
6,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 13.2 (N-amyl methyl C) 6) Mass spectrometry m / z 639 (M ⁺ )

(154) N-desethyl-N-propyl-16-epi-3,8,13-trideoxy-14-O
-Physical properties and analytical data of anisoyl aconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.19 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.83 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl) ₃ ) Analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 91.4, 86.2, 85.1, 82.0, 80. 1,
72.1 (C at positions 16,1,6,18,14,15) 60.1,58.8,57.9,56.0 (18,1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) mass spectrometry m / z 611 (M ⁺ )

(155) Physical property values and analytical data of N-desethyl-N- (4-methyl) pentyl-16-epi-3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and dissolution Colorless, non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.25 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 3.84 (3H, s) (H of methoxy group at 1,6,16 and 18 positions) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.02 (6H, d, J = 7.0 Hz) (N- (H) of methyl of (4-methyl) pentyl 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.8, 131.7, 113.4, 122.0 (C of anisoyl group) 91.3, 86.1, 85.0, 82.2, 80. 1,
72.5 (C at positions 16, 16, 6, 18, 14, 15) 60.0, 58.8, 57.9, 56.0 (18, 1
C, 6,6-methoxy group C) 55.4 (M, anisoyl group methoxy group) 21.5 (N- (4-methyl) pentyl, methyl group C) 6) Mass spectrum analysis m / z 653 ( M ⁺ )

(156) N-desethyl-N-acetyl-16-epi-3,8,13-trideoxy-14-O
-Physical properties and analytical data of anisoyl aconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, water Insoluble in 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.19 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.82 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (same as above) 3.28 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 2.28 (3H, s) (H of methyl N-acetyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (8, ppm). 171.8 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 163.7, 131.6, 113.4, 122.2 (C of anisoyl group) 91.2, 84.9 , 82.5, 82.0, 80.2,
72.4 (C at positions 16, 6, 18, 1, 14, 15) 60.1, 58.7, 57.9, 56.0 (18, 1
6,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N-acetyl methyl C) 6) mass spectrometry m / z 611 (M ⁺ )

(157) N-desethyl-N-benzoyl-16-epi-3,8,13-trideoxy-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.82 to 7.09 (5H, m) (H of benzoyl group) 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d, J = 8. 9) (Id.) 5.21 (1H, t, J = 4.8 Hz) (βH at position 14) 3.88 (3H, s) (methoxy H of anisoyl group) 3.83 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.24 (3H, s) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0, 165.8 (C of carbonyl) 163.8, 131.7, 113.6, 122.0 (C of anisoyl group) 133.9, 133.4, 128.6, 128.2, 1
27.6 (C of benzoyl group) 91.3, 85.0, 82.4, 82.0, 80.3,
72.6 (C at positions 16, 6, 18, 1, 14, 15) 60.2, 58.8, 57.9, 56.0 (18, 1
6,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) Mass spectrum analysis m / z 662 (M ⁺ )

(158) Physical property values and analytical data of 16-epi-14-O-m-chlorobenzoyl-pyroaconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, Soluble in ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.98 to 7.30 (5H, m) (H of m-chlorobenzoyl group) 5.40 (1H, d, J = 5.0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3 .28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 5) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 165.0 (C of carbonyl of m-chlorobenzoyl group) 131.6, 129.8, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 86.1,84.1,83.6,78.3,77.4
76.8, 71.9 (16, 6, 1, 14, 13, 1
8,3rd C) 62.3,59.2,57.8,56.1 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 6) Mass spectrometry m / z 619,621 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₂ NO ₉ Cl, calculated C: 61.98, H:
6.83, N: 2.26 Found C: 62.05, H: 6.91, N: 2.05

(159) Physical properties and analytical data of 16-epi-14-O-acetyl-pyroaconine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.24 (1H, t, J = 5.0 Hz) (βH at position 14) 3.81 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, s) ) (Same as above) 3.25 (6H, s) (same as above) 1.03 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 2.04 (3H, s) (acetyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 211.5 (C of carbonyl at position 15) 171.3 (C of carbonyl of acetyl group) 86.1, 84.0, 83.5, 78.3, 77.5,
76.8, 71.9 (16, 6, 1, 14, 13, 1
8,3,3 C) 62.4,59.1,57.8,56.1 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 21.4 (acetyl group methyl C) 5) mass Spectrum analysis m / z 523 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₁ NO ₉ , calculated value C: 61.93, H: 7.
89, N: 2.67 Found: C: 61.88, H: 7.77, N: 2.4

(160) Physical properties and analytical data of 16-epi-14-O-methyl-pyroaconine 1) Properties and dissolution A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.82 (3H, s) (H of methoxy group at positions 1, 6, 16, 18 and 14) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3 .26 (3H, s) (same as above) 3.38 (3H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 4) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 86.2,84.1,83.6,81.3,77.5
76.8, 71.9 (16, 6, 1, 14, 13, 1
8,3rd position C) 62.4,59.1,58.1,57.8,56.1
(C of methoxy group at positions 16, 18, 14, 6, 1) 49.1 (C of N-ethyl methylene) 13.4 (C of N-ethyl methyl) 5) Mass spectrum analysis m / z 495 (M ⁺ ) 6) Elemental analysis C ₂₆ H ₄₁ NO ₈ , calculated C: 63.01, H: 8.
34, N: 2.83 Found: C: 63.20, H: 8.33, N: 2.61

(161) Physical property values and analytical data of N-desethyl-N-benzoyl-16-epi-pyrogesaconitine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.93 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 7.82 to 7.10 (5H, m) (H of benzoyl group) 5.39 (1H, d, J = 5.0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3 3.30 (3H, s) (same as above) 3.26 (6H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃₎ ) Analysis Shows the following signals (δ, ppm). 211.6 (carbonyl C at position 15) 166.0, 165.7 (carbonyl C) 86.1, 84.1, 80.0, 78.2, 77.5
76.7, 72.0 (16, 6, 1, 14, 13, 1
8,3rd C) 62.3,59.2,57.8,56.1 (16,1
85.4, 131.8, 121.6, 113.8 (C of anisoyl group) 135.4, 129. 8, 129.5, 128.3 (C of benzoyl group) 6) Mass spectrum analysis m / z 691 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₅ NO ₁₁ , Calculated value C: 65.98, H:
6.56, N = 2.02 found C = 66.17, H: 6.34 N: 1.98

(162) Physical property values and analytical data of N-desethyl-N-propyl-16-epi-pyrogesaconitine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by adding ether, chloroform, benzene, ethanol, Soluble in methanol, ethyl acetate, pyridine, dimethylsulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.94 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.40 (1H, t, J = 5. 0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.26 (6H, s) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic field Resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 166.0 (C of carbonyl of anisoyl group) 164.0, 131.9, 121.5, 113.7 (C of anisoyl group) 86.1, 84.0 , 83.6, 78.1, 77.4,
76.6, 71.9 (16, 6, 1, 14, 13, 1
C, 8,3) 62.3,59.3,57.8,56.1 (16,1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) Mass spectrometry m / z 629 (M ⁺ ) 7) Elemental analysis: C ₃₄ H ₄₇ NO ₁₀ , calculated value: C: 64.85, H:
7.52, N: 2.2 actual value C: 65.03, H: 7, 49, N: 2.1

(163) Physical Properties and Analytical Data of N-Desethyl-N-acetyl-16-epi-pyrrojesaconitine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, It is soluble in methanol, ethyl acetate, pyridine, and dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.95 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.40 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.81 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.26 (6H, s) 2.30 (3H, s) (methyl H of acetyl group) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 170.8 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 164.0, 131.8, 121.6, 113, 8 (Anisoyl Group C) 86.1, 84.0, 80.0, 78.0, 77.5,
76.6, 71.9 (16, 6, 1, 14, 13, 1
C, 8,3) 62.3,59.3,57.9,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.1 (N-acetyl methyl C) 6) Mass spectrometry m / z 629 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₃ NO _11, calculated value C: 62.94, H:
6.88, N: 2.22 actual value: C: 63.18, H: 7.01, N: 2.05

(164) 3-Deoxy-16-epi-1
4-O-m-chlorobenzoyl-pyroaconine physical properties and analytical data 1) Properties and solubility Colorless, non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide And is insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) 7.97 to 7.30 (5H, m) (H of m-chlorobenzoyl group) 5.39 (1H, d, J = 5.0 Hz) (βH at position 14) 3.81 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3 .27 (3H, s) (same as above) 3,25 (3H, s) (same as above) 1.04 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 5) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 165.1 (C of carbonyl of m-chlorobenzoyl group) 131.8, 129.7, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 86.2, 85.0, 83.7, 80.2, 78.4,
77.4, (C at position 16, 16, 6, 18, 14, 13) 62.3, 59.2, 57.8, 56.0 (16, 1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.5 (N-ethyl methyl C) 6) Mass spectrum analysis m / z 603,605 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₂ NO ₈ Cl, calculated C: 63.62,
H: 7.01, N: 2.32 Actual value: C: 63.41, H: 6.94, N: 2.22

(165) 3-Deoxy-16-epi-1
Physical property values and analytical data of 4-O-acetyl-pyroaconin 1) Properties and solubility A colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.20 (1H, d, J = 5.0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) ) (Same as above) 3.24 (6H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 2.05 (3H, s) (acetyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 211.6 (C of carbonyl at position 15) 171.2 (C of carbonyl of acetyl group) 86.3, 85.1, 83.5, 80.3, 78.4
77.2 (C at positions 16, 16, 6, 18, 14, 13) 62.4, 59.1, 57.9, 56.0 (16, 1
8,6,1 position methoxy group C) 49.1 (N-ethyl methylene C) 13.2 (N-ethyl methyl C) 21.4 (acetyl group methyl C) 5) mass Spectrum analysis m / z 507 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₁ NO ₈ , calculated value C: 63.89, H: 8.
14, N: 2.76 Found C: 64.11, H: 8.36, N: 2.51

(166) 3-Deoxy-16-epi-1
Physical property value and analytical data of 4-O-methyl-pyroaconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and hexane , Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711 cm ^-1 . 3 ¹ H nuclear magnetic resonance spectrum (CDCl ₃₎ shows the analysis following signals (δ, ppm). 3.81 (3H, s) (H of the methoxy group at positions 1, 6, 16, 18 and 14) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3 .26 (3H, s) (same as above) 3.38 (3H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 4) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 86.2, 85.1, 83.6, 80.2, 78.5
77.3, (C at positions 16,1,6,18,14,13) 62.5,59.1,58.1,57.8,56.0
(C of methoxy group at positions 16, 18, 14, 6, 1) 49.1 (C of N-ethyl methylene) 13.3 (C of N-ethyl methyl) 5) Mass spectrum analysis m / z 479 (M ⁺ ) 6) Elemental analysis C ₂₆ H ₄₁ NO ₇ , calculated C: 65. H, H: 8.
62, N: 2.92, measured C: 65.30, H: 8.51, N: 3.01

(167) Physical Properties and Analytical Data of N-desethyl-N-benzoyl-3-deoxy-16-epi-pyrrojesaconitine 1) Properties and solubility A colorless non-crystalline powder containing ether, chloroform, Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.93 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 7.82 to 7.09 (5H, m) (H of benzoyl group) 5.40 (1H, d, J = 5.0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3 , 30 (3H, s) (same as above) 3.26 (6H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃₎ ) Analysis The following signals are shown (δ, ppm). 211.6 (carbonyl C at position 15) 166.0, 165.7 (carbonyl C) 86.1, 83.5, 82.0, 80.3, 78.2
77.5 (C at positions 16, 6, 1, 18, 14, 13) 62.3, 59.2, 57.8, 56.0 (16, 1
85.4, 131.8, 121.6, 113.8 (C of anisoyl group) 135.4, 129. 8, 129.5, 128.3 (C of benzoyl group) 6) Mass spectrum analysis m / z 675 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₅ NO ₁₀ , calculated value C: 67.54, H:
6.71, N: 2.07 Found C: 67.66, H: 6.52, N: 1.95

(168) Physical Properties and Analytical Data of N-Desethyl-N-propyl-3-deoxy-16-epi-pyrogesaconitine 1) Properties and solubility It is soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.94 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.40 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.80 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.26 (6H, s) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic field Resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 166.0 (C of carbonyl of anisoyl group) 164.0, 131.9, 121.5, 113.7 (C of anisoyl group) 86.2, 85.1 , 83.5, 80.2, 78.2,
77.4 (C at positions 16,1,6,18,14,13) 62,3,59.4,57.9,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) Mass spectrometry m / z 613 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₇ NO ₉ , calculated value C: 66.54, H:
7.72, N: 2.28 Found C: 66.74, H: 7.65, N: 2.20

(169) Physical property values and analytical data of N-desethyl-N-acetyl-3-deoxy-16-epi-pyrogesaconitine 1) Properties and solubility Soluble in benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1654 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.95 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d, J = 8.9) (same as above) 5.41 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.81 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.26 (3H, s) 3.25 (3H, s) (same as above) 2.32 (3H, s) (methyl H of acetyl group) 3.87 (3H, s) (methoxy H of anisoyl group) 5 ) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.5 (C of the carbonyl at position 15) 171.4 (C of the carbonyl of acetyl group) 166.0 (C of the carbonyl of anisoyl group) 164.1, 131.8, 121.6, 113.8 (Anisoyl Group C) 86.2, 83.4, 82.0, 80.3, 78.2,
77.3 (C at position 16, 16, 1, 18, 14, 13) 62.3, 59.4, 57.9, 56.0 (16, 1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.1 (N-acetyl methyl C) 6) Mass spectral analysis m / z 613 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₃ NO _10, calculated value C: 64.59, H:
7.06, N: 2.28 Found C: 64.41, H: 7.00, N: 2.35

(170) 3,13-dideoxy-16-
Physical property values and analytical data of epi-14-O-m-chlorobenzoyl-pyroaconin 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 to 7.35 (5H, m) (H of m-chlorobenzoyl group) 5.50 (1H, d, J = 5.0 Hz) (βH at position 14) 3.63 (3H, s) ( H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3.25 (3H, s) (same as above) 1.04 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 165.0 (C of carbonyl of m-chlorobenzoyl group) 131.8, 129.7, 129.5, 135.0, 1
28.4 (C of m-chlorobenzoyl group) 85.2, 85.0, 83.7, 80.2, 78.4
(C at 16,1,6,18,14th position) 61.1,59.2,57.8,56.0 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 6) Mass spectrometry m / z 587,589 (M ⁺ ) 7) elemental analysis C ₃₂ H ₄₂ NO ₇ Cl, calculated C: 65.35,
H: 7.20, N: 2.38 Found: C: 65.51, H: 7.25, N: 2.09

(171) 3,13-dideoxy-16-
Physical property value and analytical data of epi-14-O-acetyl-pyroaconine 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 5.38 (1H, t, J = 5.0 Hz) (βH at position 14) 3.65 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) 3.25 (6H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (H of N-ethyl methyl) 2.05 (3H, s) (acetyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signal (δ, ppm) 211.6 (C of carbonyl at position 15) 171.2 (C of carbonyl of acetyl group) ) 85.3, 85.1, 83.5, 80.3, 78.4
(C at 16, 16, 6, 18, 14th position) 61.4, 59.1, 57.9, 56.0 (16, 1
8,6,1-position methoxy group C) 49.1 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 21.4 (acetyl group methyl C) 5) Mass Spectrum analysis m / z 491 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₁ NO ₇ , calculated value C: 65.96, H:
8.41, N: 2.85 Found C: 66.26, H: 8.55, N: 2.97

(172) 3,13-dideoxy-16-
Physical property value and analytical data of epi-14-O-methyl-pyroaconin 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide. Insoluble in hexane and water. 2) shows a maximum absorption in the infrared absorption spectrum (KBr) analysis 1711cm ^-1 1. ) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.66 (3H, s) (H of methoxy group at positions 1, 6, 16, 18, and 14) 3.30 (3H, s) (same as above) 3.27 (3H, s) (same as above) 3 3.26 (3H, s) (same as above) 3.38 (3H, s) (same as above) 1.05 (3H, t, J = 7.0 Hz) (N-ethyl methyl H) 4) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 85.2, 85.0, 83.6, 80.2, 78.6
(C at 16, 16, 6, 18, 14th position) 61.3, 59.1, 58.1, 57.8, 56.0
(C of methoxy group at positions 16, 18, 14, 6, 1) 49.0 (C of N-ethyl methylene) 13.2 (C of N-ethyl methyl) 5) Mass spectrum analysis m / z 463 (M ⁺ ) 6) Elemental analysis C ₂₆ H ₄₁ NO ₆ , Calculated C: 67.36, H:
8.91, N: 3.02 actual value C: 67.41, H: 9.02, N: 2.89

(173) Physical property values and analytical data of N-desnityl-N-benzoyl-3,13-dideoxy-16-epi-pyrogesaconitine 1) Properties and solubility A colorless non-crystalline powder containing ether, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1711, 1653 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.94 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 7.82 to 7.10 (5H, m) ) (H of benzoyl group) 5.45 (1H, t, J = 5.0 Hz) (βH at position 14) 3.65 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.25 (6H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl) ₃ ) Analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 166.0, 165.7 (C of carbonyl) 85.4, 83.5, 82.0, 80.2, 78.2
(C at 16, 16, 1, 18, 14th position) 61.2, 59.0, 57.8, 56.0 (16, 1
85.4, 131.8, 121.6, 113.8 (C of anisoyl group) 135.4, 129. 8, 129.5, 128.3 (C of benzoyl group) 6) Mass spectrum analysis m / z 659 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₅ NO ₉ , calculated value C: 69.18, H:
6.87, N: 2.12 Found C: 69.20, H: 6.69, N: 2.01

(174) Physical property values and analytical data of N-desethyl-N-propyl-3,13-dideoxy-16-epi-pyrogesaconitine 1) Properties and solubility A colorless non-crystalline powder containing ether, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.94 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.46 (1H, t, J = 5. 0 Hz) (βH at position 14) 3.64 (3H, s) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (as above) 3.26 (6H, s) 1.10 (3H, t, J = 7.0 Hz) (H of N-propyl methyl) 3.87 (3H, s) (methoxy H of anisoyl group) 5) ¹³ C nuclear magnetic field Resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.6 (C of carbonyl at position 15) 166.0 (C of carbonyl of anisoyl group) 164.0, 131.9, 121.5, 113.8 (C of anisoyl group) 85.4, 85.1 , 83.5, 80.0, 78.4
(C at 16, 16, 6, 18, 14th position) 61.3, 59.5, 57.9, 56.0 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 13.0 (N-propyl methyl C) 6) mass spectrometry m / z 597 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₇ NO ₈ , Calculated C: 68.32, H:
7.93, N: 2.34 Found: C: 68.01, H: 8.16, N: 2.16

(175) Physical property values and analytical data of N-desethyl-N-acetyl-3,13-dideoxy-16-epi-pyrogesaconitine 1) Properties and solubility A colorless non-crystalline powder, Soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1654 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, d, J = 8.9) (H of anisoyl group) 6.96 (2H, d, J = 8.9) (same as above) 5.46 (1H, t, J = 5. 0 Hz) (βH at position 14) 3.64 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.26 (3H, s) 3.25 (3H, s) (same as above) 2.30 (3H, s) (methyl H of acetyl group) 3.87 (3H, s) (methoxy H of anisoyl group) 5 ) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.5 (C of carbonyl at position 15) 171.4 (C of carbonyl of acetyl group) 166.0 (C of carbonyl of anisoyl group) 164.1, 131.8, 121.6, 113.8 (Anisoyl Group C) 85.4, 83.4, 82.0, 80.2, 78.0
(C at positions 16, 6, 1, 18, and 14) 61.3, 59.4, 57.9, 56.0 (16, 1
8,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.1 (N-acetyl methyl C) 6) mass spectrometry m / z 597 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₃ NO _9, calculated C: 66.31, H:
7.25, N: 2.34 measured C: 66.51, H: 7.20, N: 2.28

(176) N-desethyl-N- (2-methyltetrahydrofurfuryl) -8-deoxy-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.98 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.93 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of anisoyl group) 163.7, 131.8, 121.1, 113.8 (C of anisoyl group) 94.2, 85.0, 83.7, 80.2, 77. 5,
75.1, 72.3, 72.0 (16, 6, 1, 14,
18,13,15,3rd position C) 61.9,59.0,57.9,56.0 (16,1
8,6,1-position methoxy group C) 55.4 (methoxy of anisoyl group) 21.5 (methyl C of 2-methyltetrahydrofurfuryl) 6) mass spectrometry m / z 687 (M ⁺ 7) Elemental analysis C ₃₇ H ₅₃ NO ₁₁ , Calculated C: 64.61, H:
7.77, N: 2.04 Found C: 64.48, H: 7.69, N: 2.11

(177) N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,8-dideoxy-
Physical property value and analytical data of 14-O-anisoylaconine 1) Property and solubility Colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, Insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.95 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.23 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.7, 131.8, 122.2, 113.7 (C of anisoyl group) 94.3, 86.0, 85.1, 82.1, 80. 0,
75.3, 72.1, 72.0 (16, 6, 1, 18,
C at position 14, 13, 15) 61.7, 59.0, 58.0, 56.0 (16, 1
8,6,1-position C of methoxy group) 55.4 (methoxy C of anisoyl group) 21.5 (methyl C of 2-methyltetrahydrofurfuryl) 6) Mass spectrum analysis m / z 671 (M ⁺ ) 7) elemental analysis C ₃₇ H ₅₃ NO _10, calculated value C: 66.15, H:
7.95, N: 2.08 Found C: 65.89, H: 7.72, N: 1.98

(178) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless Is a non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.97 (2H, d, J = 8.9) (same as above) 5.06 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, s) (ibid) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.51 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 94.3, 86.2, 85.1, 82.0, 80. 0,
72.1 (C at positions 16,1,6,18,14,15) 59.3,58.8,57.9,56.0 (18,1
C, 6,6-methoxy position C) 55.4 (Methoxy C, anisoyl group) 21.5 (Methyl C, 2-methyltetrahydrofurfuryl) 6) Mass spectrometry m / z 655 (M ⁺ ) 7) elemental analysis C ₃₇ H ₅₃ NO _9, calculated C: 67.76, H:
8.15, N: 2.14 Found C: 67.91, H: 8.13, N: 2.05

(179) Physical Properties and Analytical Data of N-Desethyl-N- (2-methyltetrahydrofurfuryl) -14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether It is soluble in chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 4.96 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.69 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (ibid) 3.29 (3H, s 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.51 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6,131.7,122.1,113.8 (C of anisoyl group) 90.8,83.6,82.3,81.8,79. 5,
78.5, 77.2, 74.8, 72.0 (16, 6,
1,5,14,8,18,13,3rd position C) 61.8,59.1,58.0,56.1 (16,1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.6 (2-methyltetrahydrofurfuryl methyl C) 6) mass spectral analysis m / z 703 (M ⁺ ) 7) elemental analysis C ₃₇ H ₅₃ NO _12, calculated value C: 63.14, H:
7.59, N: 1.99 Found: C: 63.02, H: 7.65, N: 2.08

(180) N-desethyl-N- (2-methyltetrahydrofurfuryl) -3-deoxy-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility Colorless amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, hexane, Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 4.98 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.70 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.27 (3H, s) 3.25 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of anisoyl group) 163.6, 131.8, 122.1, 113.8 (C of anisoyl group) 90.8, 85.4, 83.3, 81.0, 79, 9,
79.5, 78.6, 75.0 (16, 1, 6, 18,
13, 15, 14, 8, 13th position C) 61.7, 59.0, 58.0, 56.1 (16, 1
8,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.4 (2-methyltetrahydrofurfuryl methyl C) 6) mass spectrometry m / z 687 (M ⁺ 7) Elemental analysis C ₃₇ H ₅₃ NO ₁₁ , Calculated C: 64.61, H:
7.77, N: 2.04 Found: C: 64.43, H: 7.92, N: 1.87

(181) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,13-dideoxy-14-O-anisoylaconine 1) Properties and solubility It is a crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethylsulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.08 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.67 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 89.8, 85.3, 83.4, 81.4, 81.4, 79. 8,
78.6, 77.4 (16, 1, 6, 18, 15, 8,
14th C) 59.1, 57.9, 57.5, 55.9 (18, 1
6,5.4, C of methoxy group at position 1) 55.4 (C of methoxy of anisoyl group) 21.5 (C of methyl of 2-methyltetrahydrofurfuryl) 6) Mass spectrometry 1 / z 671 (M ⁺ ) 7) elemental analysis C ₃₇ H ₅₃ NO _10, calculated value C: 66.15, H:
7.95, N: 2.08 Found C: 66.01, H: 8.16, N: 1.99

(182) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-8-deoxy-14-O-anisoylaconine 1) Properties and solubility Amorphous powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.12 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 122.2, 113.8 (C of anisoyl group) 91.2, 85.1, 83.6, 80.2, 77. 5,
76.0, 72.3, 71.9 (16, 6, 1, 14,
C, 18,13,15,3) 62.2,59.1,57.9,56.1 (16,1
8,6,1-position methoxy group C) 55.4 (methoxy of anisoyl group) 21.5 (methyl C of 2-methyltetrahydrofurfuryl) 6) mass spectrometry m / z 687 (M ⁺ )

(183) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -16epi-3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility It is a colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.94 (2H, d, J = 8.9) (same as above) 5.14 (1H, d, J = 5. 0 Hz) (βH at position 14) 3.84 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.51 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 122.1, 113.8 (C of anisoyl group) 91.3, 86.2, 85.0, 82.1, 80. 1,
76, 1, 77.2 (16, 1, 6, 15, 18, 1
C at positions 4, 13, 15) 62.1, 59.0, 58.0, 56.0 (16, 1
8,6,1-position C of methoxy group) 55.4 (methoxy C of anisoyl group) 21.5 (methyl C of 2-methyltetrahydrofurfuryl) 6) Mass spectrum analysis m / z 671 (M ⁺ )

(184) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility Colorless Is a non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, d, J = 8.9) (H of anisoyl group) 6.95 (2H, d, J = 8.9) (same as above) 5.19 (1H, t, J = 4. 8 Hz) (βH at position 14) 3.83 (3H, s) (H of methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, s) (same as above) 3.29 (3H, s) 3.24 (3H, s) (same as above) 3.87 (3H, s) (methoxy H of anisoyl group) 1.52 (3H, s) (methyl H of tetrahydrofurfuryl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of anisoyl group) 163.6, 131.8, 122.2, 113.7 (C of anisoyl group) 91.4, 86.2, 85.1, 82.0, 80. 1,
72.1 (C at positions 16,1,6,18,14,15) 60.1,58.8,57.9,56.0 (18,1
C, 6,6-methoxy position C) 55.4 (Methoxy C, anisoyl group) 21.5 (Methyl C, 2-methyltetrahydrofurfuryl) 6) Mass spectrometry m / z 655 (M ⁺ )

(185) Physical properties and analytical data of 3,13,15-trideoxygesaconitin 1) Properties and solubility Colorless needles having a melting point of 153-154 ° C, ether, chloroform, benzene, ethanol, methanol It is soluble in ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1713 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, d, J = 8.9 Hz) (H of anisoyl group) 6.90 (2H, d, J = 8.9 Hz) (same as above) 5.04 (1H, t, J = 4.0 Hz). 5 Hz) (βH at position 14) 3.85 (3H, s) (H of methoxy group at anisoyl group) 3.37 (3H, s) (H at methoxy group at 1,6,16 and 18 positions) 3.28 (3H, s) (same as above) 3.26 (3H, s) (same as above) 3.17 (3H, s) (same as above) 1.08 (3H, t, J = 7.1 Hz) (N− 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 169.8 (C of carbonyl of acetyl group) 166.2 (C of carbonyl of anisoyl group) 163.5, 131.8, 123.0, 113.7 (C of anisoyl group) 85.9, 85.1 , 83.5, 82.9, 80.4,
75.4 (C at 8,1,16,6,18,14th position) 59.1,57.8,56.6,56.0 (18,1
6. Methoxy group C at 6, 6, 1-position) 55.4 (Methoxy group C of anisoyl group) 49.0 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 21. 8 (C 6 of methyl of acetyl group) mass spectrum analysis m / z 627 (M ⁺ ) 7) high-resolution mass spectrum analysis calculated value 627.3407 (C ₃₅ H ₄₉ NO ₉ ),
Measured value 627.3394

(186) Physical Properties and Analytical Data of 3-O-acetyl-8-O-linoleoyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ¹⁸ = +1.31 (CHCl ₃ , c = 1.
47) 3) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 5.35 (4H, multiplet) (linoleic acid residue) 4.85 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.44 (2H, multiplet) (H at 15th position, OH at 15th position) 4 0.06 (1H, doublet, J = 6.93 Hz) (H at 6-position) 3.73 (3H, singlet) (H at 1,6,16 and 18-position methoxy group) 3.26 ( 3H, unit weight line) (same as above) 3.19 (6H, unit weight line) (same as above) 2.35 (3H, unit weight line) (H of N-CH ₃₎ 2.06 (3H, unit weight Line) (H of 3-acetyl group) 0.89 (3H, singlet, J = 7.60 Hz) (H of linoleic acid terminal methyl) 6) ¹³ C nuclear magnetic resonance spectrum (CDC l ₃₎ shows the analysis following signals (δ ppm). 174.9 (C of carbonyl group derived from linoleic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.3, 90.1, 83.3, 81.9, 78.8,
74.0, 71.4, 71.2, (8, 16, 6, 1,
14,15,13,18,3rd position C) 61.0,58.7,58,4,56.6 (1
C) 42.5 (C of N—CH ₃ ) 21.1 (C of methyl group of acetyl group bonded to 3 position) 7) EI-mass spectrum analysis _{^{m / z 613 (M + -C}} 18 H 32 O 2), 582
_{^{(M + -C 18 H 32 O}} 2 -CH 3 OH) 8) FD- Mass spectrometry m / z 893 ^(M +)

(187) Physical property values and analytical data of 3-O-acetyl-8-O-palmitoyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm) 8.02-8.04 (2H, multiplet) (H of benzoyl group) 7.40-7.55 (3H) 4.86 (1H, double line, J = 4.96 Hz) (14th H) 4.44 (2H, multiple line) (15th H, 15th OH) 4.05 (1H, doublet, J = 6.93 Hz) (H at 6th position) 3.74 (3H, singlet) (H2 at 1,6,16 and 18th methoxy group) 3.26 (3H, unit weight line) (same as above) 3.20 (6H, unit weight line) (same as above) 2.35 (3H, unit weight line) (H of N-CH ₃₎ 2.06 (3H, single heavy lines) (3-position acetyl group H) 0.97 (3H, triplet, J = 7.59Hz) (H palmitic acid residues terminal methyl) ^{5) 13} The analysis following signals nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from palmitic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.9, 128.5, 129.9
(C of benzoyl group) 91.3, 90.1, 83.3
81.9, 78.8, 74.0, 71.4, 71.2,
(C at 8,16,6,1,14,15,13,18,3rd position) 61.0,58.7,58.4,56.6 (16,1
8,6,1 position of the methoxy group bonded to the 1 position 42.5 (C of N-CH ₃ ) 21.1 (C of the methyl group of the acetyl group bonded to the 3 position) 6) EI-mass spectrum analysis m _{^{/ z 613 (M + -C 16}} H 32 O 2), 582
_{^{(M + -C 16 H 32 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 869 ^(M +)

(188) Physical properties and analytical data of 3-O-acetyl-8-O-oleoyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ¹⁸ = + 11.0 (CHCl ₃ , c = 0.
49) 3) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.02-8.04 (2H, multiplet) (H of benzoyl group) 7.40-7.55 (3H, multiplet) (same as above) 5.25 (2H, multiplet) (oleic acid residue) 4.86 (1H, doublet, J = 4.96 Hz) (H at 14th position) 4.44 (2H, multiplet) (H at 15th position, OH at 15th position) 4 .05 (1H, doublet, J = 6.93 Hz) (H at position 6) 3.74 (3H, singlet) (H at 1,6,16 and 18 position methoxy group) 3. 26 (3H, unit weight line) (Same as above) 3.20 (6H, unit weight line) (Same as above) 2.35 (3H, unit weight line) (H of _{N-CH 3) 2.06 (3H} , (Single bar) (H at 3-position acetyl group) 0.96 (3H, triplet, J = 7.59 Hz) (H at terminal methyl of oleic acid residue) 6) of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ ppm). 175.0 (C of carbonyl group derived from oleic acid residue at position 8) 170.2 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.3, 90.1, 83.3, 82.0, 78.8,
74.0, 71.3, 71.2, (8, 16, 6, 1,
C at positions 14, 15, 13, 18, and 3) 61.1, 58.7, 58.4, 56.6 (16, 1
8,6,1-position of methoxy group C) 42.5 (C of N-CH ₃ ) 21.1 (3-point methyl group of acetyl group) 7) EI-mass spectrum analysis m _{^{/ z 613 (M + -C 18}} H 34 O 2), 582
_{^{(M + -C 18 H 34 O}} 2 -CH 3 OH) 8) FD- Mass spectrometry m / z 895 ^(M +)

(189) Physical properties and analytical data of 3-O-acetyl-8-O-stearoyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.55 (3H, multiplet) (same as above) 4.85 (1H, doublet, J = 4. 96Hz) (14th H) 4,44 (2H, multiple lines) (15th H, 15th OH) 4.06 (1H, doublet, J = 6.93Hz) (6th H) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 26 (3H, unit weight line) (Same as above) 3.19 (6H, unit weight line) (Same as above) 2.35 (3H, unit weight line) (H of _{N-CH 3) 2.06 (3H} , (Single bar) (H at 3-position acetyl group) 0.96 (3H, triplet, J = 7.59 Hz) (H at stearic acid terminal methyl) 5) of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis shows the following signal (δ ppm) 174.9 (C of carbonyl group derived from 8-position stearic acid residue) 170.2 (C of carbonyl group derived from 3-acetyl group) 165.9 (14th position C) 133.1, 129.6, 128.5, 129.9 of carbonyl group derived from benzoyl group
(C of benzoyl group) 91.3, 90.1, 83.3, 82.0, 78.9,
74.0, 71.4, 71.2, (8, 16, 6, 1,
C at positions 14, 15, 13, 18, and 3) 61, 1, 58.7, 58.4, 56.6 (16, 1
8,6,1 position of the methoxy group bonded to the 1 position 42.5 (C of N-CH ₃ ) 21.1 (C of the methyl group of the acetyl group bonded to the 3 position) 6) EI-mass spectrum analysis m _{^{/ z 613 (M + -C 16}} H 36 O 2), 582
_{^{(M + -C 18 H 36 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 897 ^(M +)

(190) Physical properties and analytical data of 3-O-acetyl-8-O-linolenoyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) [α] _D ²¹ = +23.6 (CHCl ₃ , c = 0.
44) 3) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 5.30 (6H, multiplet) (linolenic acid residue) 4.85 (1H, doublet, J = 4.95 Hz) (H at position 14) 4.44 (2H, multiplet) (H at position 15, OH at position 15) 4.06 (1H, doublet, J = 6.93 Hz) (H at 6th position) 3.73 (3H, singlet) (H at 1,6,16 and 18th methoxy group) 3. 26 (3H, unit weight line) (Same as above) 3.19 (6H, unit weight line) (Same as above) 2.35 (3H, unit weight line) (H of _{N-CH 3) 2.06 (3H} , (Single bar) (H of 3-acetyl group) 0.96 (3H, triplet, J = 7.59 Hz) (H of methyl at the end of linolenic acid residue) 6) of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ ppm). 175.0 (C of carbonyl group derived from linolenic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.9, 129.6, 128.5
(C of bezoyl group) 91.3, 90.1, 83.3, 82.0, 78.8,
74.0, 71.4, 71.2, (8, 16, 6, 1,
C at positions 14, 15, 13, 18, and 3) 61.1, 58.7, 58.4, 56.6 (16, 1
8,6,1-position of methoxy group C) 42.5 (C of N-CH ₃ ) 21.1 (3-point methyl group of acetyl group) 7) EI-mass spectrum analysis m _{^{/ z 613 (M + -C 18}} H 30 O 2), 582
_{^{(M + -C 18 H 30 O}} 2 -CH 3 OH) 8) FD- Mass spectrometry m / z 891 ^(M +)

(191) Physical property values and analytical data of 3-O-acetyl-8-O-lauroyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 4.85 (1H, doublet, J = 4. 96 Hz) (14th H) 4.44 (2H, multiple line) (15th H, 15th OH) 4.06 (1H, doublet, J = 6.93 Hz) (6th H) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 26 (3H, unit weight line) (Same as above) 3.19 (6H, unit weight line) (Same as above) 2.35 (3H, unit weight line) (H of _{N-CH 3) 2.06 (3H} , (Single bar) (H of acetyl group at position 3) 0.96 (3H, triplet, J = 7.59 Hz) (H of methyl at lauric acid terminal) 5) of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis shows the following signal (δ ppm) 175.0 (C of carbonyl group derived from lauric acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C C) 133.1, 129.9, 129, 6,128.5 of carbonyl group derived from benzoyl group
(C of benzoyl group) 91.3, 90.1, 83.3
81.9, 78.8, 74.0, 71.4, 71.2,
(C at 8,16,6,1,14,15,13,18,3rd position) 61.0,58.7,58.4,56.6 (16,1
8,6,1 position of methoxy group bonded to position 1) 42.5 (C of N-CH ₃ ) 21.1 (C of position of methyl group of acetyl group bonded to position 3) 6) EI-mass spectrum analysis m / Z 613 (M ⁺ -C ₁₂ H ₂₄ O ₂ , 582 (M
_{^{+ -C 12 H 24 O 2 -CH}} 3 OH) 7) FD- Mass spectrometry m / z 813 ^(M +)

(192) Physical properties and analytical data of 3-O-acetyl-8-O-linoleoyl-14-O-benzoylaconine Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ¹⁸ = -4.35 (CHCl ₃ , c = 1.
47) 3) Infrared absorption spectrum (CDCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 5.35 (4H, multiplet) (linoleic acid residue) 4.85 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.46 (2H, multiplet) (H at 15th position, OH at 15th position) 4 0.07 (1H, doublet, J = 6.95 Hz) (H at position 6) 3.74 (3H, singlet) (H at 1,6,16 and 18th methoxy group) 3.20 ( 3H, unit weight line) (same as above) 3.19 (6H, unit weight line) (same as above) 1.12 (3H, triplet, J = 7.0 Hz) (methyl group _N-CH 2 _{CH 3} H) 2.07 (3H, singlet) (H of 3-acetyl group) 0.97 (3H, triplet, J = 7.59 Hz) (H of linoleic acid residue terminal methyl) ) Shows signals for analysis the following ¹³ C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 174.9 (C of carbonyl group derived from linoleic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.5, 90.1, 83.5, 81.9, 78.8,
74.0, 71.4, (8, 16, 6, 1, 14, 1
C, 6,13,18,3) 60.6,58.7,58.4,56.3 (16,1
8,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 7} ) EI Mass spectrometry m / z 627 (M ⁺ -C ₁₈ H ₃₂ O ₂ ), 596
_{^{(M + -C 18 H 32 O}} 2 -CH 3 OH) 8) FD- Mass spectrometry m / z907 ^(M +)

(193) Physical Properties and Analytical Data of 3-O-acetyl-8-O-palmitoyl-14-O-benzoylaconine 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CDCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 4.85 (1H, doublet, J = 4. 95 Hz) (14th H) 4.46 (2H, multiplet) (15th H, 15th OH) 4.07 (1H, doublet, J = 6.95 Hz) (6th H) 3.74 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.20 (3H, singlet) (same as above) 3.19 (6H, singlet) ( same as above) 2.07 (3H, unit weight line) (H at the 3-position acetyl group) 1.12 (3H, triplet, J = 7.0Hz) (H methyl group _N-CH 2 -CH ₃₎ 0.96 analysis of the (3H, triplet, J = 7.59Hz) (H palmitic acid residues terminal methyl) ^{5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ Shows the signal ([delta] ppm). 174.9 (C of carbovol group derived from palmitic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.5, 90.1, 83.5, 81.9, 78.8,
74.0, 71.4, (8, 16, 6, 1, 14, 1
C, 6,13,18,3) 60.6,58.7,58.4,56.3 (16,1
8,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 6} ) EI Mass spectrometry m / z 627 (M ⁺ -C ₁₆ H ₃₂ O ₂ ), 596
_{^{(M + -C 16 H 32 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 883 ^(M +)

(194) Physical properties and analytical data of 3-O-acetyl-8-O-oleoyl-14-O-benzoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃₎ shows a maximum absorption in the analysis 3500,2940,1720cm ^-1 1. 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 5.25 (2H, multiplet) (oleic acid residue) 4.85 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.46 (2H, multiplet) (H at 15th position, OH at 15th position) 4.07 (1H, doublet, J = 6.95 Hz) (H at position 6) 3.74 (3H, singlet) (H at 1,6,16 and 18 methoxy groups) 3. 20 (3H, singlet) (same as above) 3.19 (6H, singlet) (same as above) 2.07 (3H, singlet) (H of 3-acetyl group) 1.12 (H, singlet) triplet, J = 7.0Hz) (H methyl group _{N-CH 2 CH 3) 0.96} (3H, triplet, J = 7.59Hz) (H oleic acid residue terminal methylation) 5) Analysis of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) shows the following signal (δ ppm) 174.9 (C of carbonyl group derived from oleic acid residue at position 8) 170.1 (carbonyl derived from acetyl group at position 3) Group C) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133.1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.5, 90.1, 83.5, 81.9, 78.8,
74.0, 71.4, (8, 16, 6, 1, 14, 1
C, 6,13,18,3) 60.6,58.7,58.4,56.3 (16,1
8,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 6} ) EI Mass spectrometry m / z 627 (M ⁺ -C ₁₈ H ₃₄ O ₂ ), 596
_{^{(M + -C 18 H 34 O}} 2) -CH 3 OH) 7) FD- Mass spectrometry m / z 909 ^(M +)

(195) Physical Properties and Analytical Data of 3-O-acetyl-8-O-stearoyl-14-O-benzoylaconine 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃₎ shows a maximum absorption in the analysis 3500,2940,1720cm ^-1 1. 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 4.85 (1H, doublet, J = 4. 95 Hz) (14th H) 4.46 (2H, multiplet) (15th H, 15th OH) 4.07 (1H, doublet, J = 6.95 Hz) (6th H) 3.74 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.20 (3H, singlet) (same as above) 3.19 (6H, singlet) ( Same as above) 2.07 (3H, singlet,) (H of 3-acetyl group) 1.12 (3H, triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.96 analysis following (3H, triplet, J = 7.59Hz) (H stearic acid residue terminal methyl) ^{5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ Shows the signal ([delta] ppm). 174.9 (C of carbonyl group derived from stearic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.5, 90.1, 83.5, 81.9, 78.8,
74.0, 71, 4, (8, 16, 6, 1, 14, 1
C, 6,13,18,3) 60.6,58.7,58.4,56.3 (16,1
8,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 6} ) EI - mass spectrometry _{m / z 627 (M-C} 18 H 36 O 2), 596 (M
_{-C 18 H 36 O 2) -CH} 3 OH) 7) FD- Mass spectrometry m / z 911 ^(M +)

(196) Physical properties and analytical data of 3-O-acetyl-8-O-linolenoyl-14-O-benzoylaconine 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 5.30 (6H, multiplet) (linolenic acid residue) 4.85 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.46 (2H, multiplet) (H at 15th position, OH at 15th position) 4.07 (1H, doublet, J = 6.95 Hz) (H at position 6) 3.74 (3H, singlet) (H at 1,6,16 and 18 methoxy groups) 3. 20 (3H, singlet) (same as above) 3.19 (6H, singlet) (same as above) 2.07 (3H, singlet) (H of 3-position acetyl group) 1.12 (3H, same as above) Triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.96 (3H, triplet, J = 7.59 Hz) (H of methyl at the end of linolenic acid residue) 5) ¹³ Analysis of C nuclear magnetic resonance spectrum (CDCl ₃ ) The following signals are shown (δ ppm). 174.9 (C of carbonyl group derived from linolenic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9 (C of benzoyl group) 91.5, 90.1, 83.5, 81.9, 78.8,
74.0, 71.4, (8, 16, 6, 1, 14, 1
C, 6,13,18,3) 60.6,58.7,58.4,56.3 (16,1
8,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 6} ) EI Mass spectrometry m / z 627 (M ⁺ -C ₁₈ H ₃₀ O ₂ ), 596
_{^{(M + -C 18 H 30 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 905 ^(M +)

(197) Physical properties and analytical data of 3-O-acetyl-8-O-lauroyl-14-O-benzoylaconine 1) Properties and solubility: A colorless oily compound containing ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 8.01-8.04 (2H, multiplet) (H of benzoyl group) 7.41-7.56 (3H, multiplet) (same as above) 4.85 (1H, doublet, J = 4. 95 Hz) (14th H) 4.46 (2H, multiplet) (15th H, 15th OH) 4.07 (1H, doublet, J = 6.95 Hz) (6th H) 3.74 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 20 (3H, singlet) (same as above) 3.19 (6H, singlet) (same as above) 2.07 (3H, singlet) (H of 3-acetyl group) 1.12 (3H, same as above) Triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.96 (3H, triplet, J = 7.59 Hz) (H of lauric acid residue terminal methyl) 5) Analysis of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) The following signals are shown (δ ppm). 174.9 (C of carbonyl group derived from lauric acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.9 (C of carbonyl group derived from benzoyl group at position 14) 133 .1, 129.6, 128.5, 129.9
(C of benzoyl group) 91.5, 90.1, 83.5,
81.9, 78.8, 74.0, 71.4, (8, 1
6,6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,
18,6,1-position bound C methoxy groups) 21.1 (C methyl group acetyl group attached to the 3-position) 13.3 (C methyl group _{N-CH 2 CH 3) 6} ) EI Mass spectrometry m / z 627 (M ⁺ -C ₁₂ H ₂₄ O ₂ ), 596
_{^{(M + -C 12 H 24 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 827 ^(M +)

(198) Physical property values and analytical data of 3-O-acetyl-8-O-linoleoyl-14-O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ¹⁸ = +24.3 (CHCl ₃ , c = 1.
06) 3) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, doublet, J = 8.90 Hz) (same as above) 5.35 (4H, multiplet) ) (H at the double bond of the linoleic acid residue) 4.84 (1H, doublet, J = 4.95 Hz) (H at the 14th position) 4.46 (1H, multiplet, J = 5. 28 Hz, J = 2.96 Hz) 15th-position β-H) 4.08 (1H, double line, J = 6.59 Hz) (6th-position β-H) 3.84 (3H, singlet) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.24 (3H, singlet) (same as above) 19 (3H, singlet) (same as above) 3.18 (3H, singlet) (same as above) 2.06 (3H, singlet) (H of 3-acetyl group) 1.10 (3H, singlet) Triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.97 (3H, triplet, J = 7.59 Hz) (H of terminal methyl group of linoleic acid residue) 6 ) Analysis of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) The following signals are shown (δ ppm). 174.9 (C of carbonyl group derived from linoleic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 .6,113.7,163.4,122.2
(C derived from anisoyl group) 91.5, 90.2, 83.5, 81.9, 78.5,
78.8, 74.0, 71.4, 71.4 (8, 16,
6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
C, the methoxy group bonded to the 8, 6, 1 position) 55.3 (C, the methoxy group of the anisoyl group) 21.1 (C, the methyl group of the acetyl group bonded to the 3 position) 13.3 (N-CH ₂ C methyl group CH ₃₎ 7) EI- mass spectrometry _{^{m / z 657 (M + -C}} 18 H 32 O 2), 626
_{^{(M + -C 18 H 32 O}} 2 -CH 3 OH) 8) FD- Mass spectrometry m / z 937 ^(M +)

(199) Physical Properties and Analytical Data of 3-O-acetyl-8-O-palmitoyl-14-O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CDCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th position β-H) 4.46 (1H, multiple lines, J = 5.28 Hz, J = 2.96 Hz) (15th position β-H) 4.08 (1H) , Doublet, J = 6.59 Hz) (β-H at position 6) 3.84 (3H, singlet) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (1 , H of the methoxy group at positions 6, 16, and 18) 3.24 (3H, singlet) (same as above) 3.19 (3H, singlet) (same as above) 3.18 (3H, singlet) ) (same as above) 2.06 (3H, unit weight line) (the 3-position acetyl group H) 1.10 (3H, triplet, J = 7.0Hz) (N- CH 2 CH 3 H-methyl group 0.97 (3H, triplet, J = 7.59Hz) shows the analysis following signals (in palmitic acid residues terminal methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 174.9 (C of carbonyl group derived from palmitic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 .6,113.7,163.4,122.2
(C of anisoyl group) 91.5, 90.2, 83.5, 81.9, 78.5,
78.8, 74.0, 71.4, 71.4 (8, 16,
6,1,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
55.3 (C of methoxy group of anisoyl group) 51.1 (C of methoxy group of anisoyl group) 21.1 (C of methyl group of acetyl group bonded to 3 position) 13.3 (N-CH ₂ CH ₃ of C methyl group) 6) EI- mass spectrometry _{^{m / z 657 (M + -C}} 16 H 32 O 2), 626
_{^{(M + -C 16 H 32 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 913 ^(M +)

(200) Physical properties and analytical data of 3-O-acetyl-8-O-oleoyl-14-O-anisoylaconine 1) Properties and solubility A colorless oily compound containing ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, doublet, J = 8.90 Hz) (same as above) 5.25 (2H, multiplet) ) (H of double bond derived from oleic acid residue) 4.84 (1H, doublet, J = 4.95 Hz) (β-H at position 14) 4.46 (1H, multiplet, J = 5) .28 Hz, J = 2.96 Hz) (β-H at position 15) 4.08 (1H, double line, J = 6.59 Hz) (β-H at position 6) 3.84 (3H, singlet) ) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.24 (3H, singlet) (same as above) 3 .19 (3H, singlet) (same as above) 3.18 (3H, singlet) (same as above) 2.06 (3H, singlet) (H of 3-position acetyl group) 1.10 (3 H, triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.97 (3H, triplet, J = 7.59 Hz) (H of methyl at the terminal methyl of oleic acid residue) 5 ) Analysis of ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) The following signals are shown (δ ppm). 174.9 (C of carbonyl group derived from oleic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 .6,113.7,163.4,122.2
(C derived from anisoyl group) 91.5, 90.2, 83.5, 81.9, 78.5,
78.8, 74.0, 71.4, 71.4 (8, 16,
6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
55.3 (C of methoxy group of anisoyl group) 51.1 (C of methoxy group of anisoyl group) 21.1 (C of methyl group of acetyl group bonded to 3 position) 13.3 (N-CH ₂ CH C) 6 methyl group of ₃₎ EI- mass spectrometry _{^{m / z 657 (M + -C}} 18 H 34 O 2), 626
_{^{(M + -C 18 H 34 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 939 ^(M +)

(201) Physical property values and analytical data of 3-O-acetyl-8-O-stearoyl-14-O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th position β-H) 4.46 (1H, multiple lines, J = 5.28 Hz, J = 2.96 Hz) (15th position β-H) 4.08 (1H) , Doublet, J = 6.59 Hz) (β-H at position 6) 3.84 (3H, singlet) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (1 , H of the methoxy group at positions 6, 16, and 18) 3.24 (3H, singlet) (same as above) 3.19 (3H, singlet) (same as above) 3.18 (3H, singlet) ) (same as above) 2.06 (3H, unit weight line) (the 3-position acetyl group H) 1.10 (3H, triplet, J = 7.0Hz) (N- CH 2 CH 3 H-methyl group 0.97 (3H, triplet, J = 7.59Hz) shows the analysis following signals (stearic acid residue terminal methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 174.9 (C of carbonyl group derived from stearic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 .6,113.7,163.4,122.2
(C derived from anisoyl group) 91.5, 90.2, 83.5, 81.9, 78, 5,
78.8, 74.0, 71.4, 71.4 (8, 16,
6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
55.3 (C of methoxy group of anisoyl group) 51.1 (C of methoxy group of anisoyl group) 21.1 (C of methyl group of acetyl group bonded to 3 position) 13.3 (N-CH ₂ CH C) 6 methyl group of ₃₎ EI- mass spectrometry _{^{m / z 657 (M + -C}} 18 H 36 O 2), 626
_{^{(M + -C 18 H 36 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 941 ^(M +)

(202) Physical Properties and Analytical Data of 3-O-Acetyl-8-O-linolenoyl-14-O-anisoylaconine , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, doublet, J = 8.90 Hz) (same as above) 5.30 (6H, multiplex) Line) (H 4.84 of double bond derived from linolenic acid residue (1H, double line, J = 4.95 Hz) (β-H at position 14) 4.46 (1H, multiple line, J = 5) .28 Hz, J = 2.96 Hz) (β-H at position 15) 4.08 (1H, double line, J = 6.59 Hz) (β-H at position 6) 3.84 (3H, singlet) ) (H of the methoxy group of the anisoyl group) 3.73 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.24 (3H, singlet) (same as above) 3 .19 (3H, singlet) (same as above) 3.18 (3H, singlet) (same as above) 2.06 (3H, singlet) (H of 3-acetyl group) 1.10 (3H) ,three Doublet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.97 (3H, triplet, J = 7.59 Hz) (H of methyl at the end of linolenic acid residue) 5) ¹³ Analysis of C nuclear magnetic resonance spectrum (CDCl ₃ ) The following signals are shown (δ ppm). 174.9 (C of carbonyl group derived from linolenic acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 6,113.7,163.4,122.2 (C derived from anisoyl group) 91.5,90.2,83.5,81.9,78.5,
78.8, 74.0, 71.4, 71.4 (8, 16,
6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
55.3 (C of methoxy group of anisoyl group) 51.1 (C of methoxy group of anisoyl group) 21.1 (C of methyl group of acetyl group bonded to 3 position) 13.3 (N-CH ₂ ) C of methyl group of CH ₃ 6) EI-mass spectrometry m / z 657 (M ⁺ -C ₁₈ H ₃₀ O ₂ ), 626
_{^{(M + -C 18 H 30 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 935 ^(M +)

(203) Physical properties and analytical data of 3-O-acetyl-8-O-lauroyl-14-O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol , Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1720 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.91 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th position β-H) 4.46 (1H, multiple lines, J = 5.28 Hz, J = 2.96 Hz) (15th position β-H) 4.08 (1H) , Doublet, J = 6.59 Hz) (β-H at position 6) 3.84 (3H, singlet) (methoxy group H of anisoyl group) 3.73 (3H, singlet) (1 3.24 (3H, singlet) (same as above) 3.19 (3H, singlet) (same as above) 3.18 (3H, singlet) ) (same as above) 2.06 (3H, unit weight line) (the 3-position acetyl group H) 1.10 (3H, triplet, J = 7.0Hz) (N- CH 2 CH 3 H-methyl group 0.97 (3H, triplet, J = 7.59Hz) shows the analysis following signals (lauric acid residue terminal methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 174.9 (C of carbonyl group derived from lauric acid residue at position 8) 170.1 (C of carbonyl group derived from acetyl group at position 3) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 131 6,113.7,163.4,122.2 (C derived from anisoyl group) 91.5,90.2,83.5,81.9,78.5,
78.8, 74.0, 71.4, 71, 4 (8, 1
6,6,1,14,15,13,18,3rd position C) 60.6,58.7,58.4,56.3 (16,1
55.3 (C of methoxy group of anisoyl group) 51.1 (C of methoxy group of anisoyl group) 21.1 (C of methyl group of acetyl group bonded to 3 position) 13.3 (N-CH ₂ C methyl group CH ₃₎ 6) EI- mass spectrometry _{^{m / z 657 (M + C}} 12 H 24 O 2), 626 (M
_{^{+ -C 12 H 24 O 2 -CH}} 3 OH) 7) FD- Mass spectrometry m / z 857 ^(M +)

(204) 8-O-linoleoyl-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ²³ = + 9.24 (CHCl ₃ , c = 1.
32) 3) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 92 (2H, doublet, J = 8.90 Hz) (same as above) 5.36 (4H, multiplet) (H of double bond of linoleic acid residue) 4.84 (1H, doublet, J = 4.95 Hz) (14th H) 4.48 (1H, multiple line, J = 5.29 Hz, J = 2.96 Hz) (15th H) 4.06 (1H, double line, J = 6.59 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (methoxy at 1,6,16 and 18) Base H) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1.10 (same as above) 3H, triplet, J = 7.0Hz) (H methyl group _{N-CH 2 CH 3) 0.97} (3H, triplet, J = 7.6Hz) (linoleic acid residues terminal methyl H) ⁶⁾ shows the analysis following signals ¹³ C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from linoleic acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5, 131.7, 122.2, 113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82, 3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 1
6,6,1,14,15,13,18,3rd position C) 60.9,58,7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 7} ) EI- mass spectrometry m _{^{/ z 615 (M + -C 18}} H 32 O 2), 584
_{^{(M + -C 18 H 32 O}} 2) -CH 3 OH) 8) FD- Mass spectrometry m / z 895 ^(M +)

(205) 8.0-O-palmitoyl-1
Physical property values and analytical data of 4-O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.92 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th H) 4.48 (1H, multiple line, J = 5.29 Hz, J = 2.96 Hz) (15th H) 4.06 (1H, double line) , J = 6.59 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (1,6,16 and 18) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1 .10 (3H, triplet, J = 7.0Hz) (H methyl group _{N-CH 2 CH 3) 0.96} (3H, triplet, J = 7.6Hz) (palmitic acid The analysis following signal group terminated methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from palmitic acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5,131.7,122.2,113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82.3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 16,
6,1,14,15,13,18,3rd position C) 60.9,58.7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 6} ) EI- mass spectrometry m _{^{/ z 615 (M + -C 16}} H 32 O 2), 584
(M ⁺ -C ₁₆ H ₃₂ O ₂ -CH ₃ OH) 7) FD-mass spectrum analysis m / z 871 (M ⁺ )

(206) 8-O-Oleoyl-14-O
-Physical properties and analytical data of anisoyl aconin 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm) 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.92 (2H, Double line, J = 8.90 Hz) (Same as above) 5.36 (2H, multiple line) (H of double bond of oleic acid residue) 4.84 (1H, double line, J = 4.95 Hz) ) (14th position H) 4.48 (1H, multiple line, J = 5.29 Hz, J = 2.96 Hz) (15th position) 4.06 (1H, double line, J = 6.59 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (H of methoxy group at 1,6,16 and 18) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1.10 (3H, triplet, J = 7.0 Hz) (H of methyl group of N-CH ₂ CH ₃ ) 0.96 (3H, triplet, J = 7.6 Hz) (terminal of oleic acid residue) Analysis of H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) of methyl The following signals are shown (δ ppm). 175.0 (C of carbonyl group derived from oleic acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5, 131.7, 122.2, 113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82.3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 1
6,6,1,14,15,13,18,3rd position C) 60.9,58.7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 6} ) EI- mass spectrometry m _{^{/ z 615 (M + -C 18}} H 34 O 2), 584
_{^{(M + -C 18 H 34 O}} 2 CH 3 OH) 7) FD- Mass spectrometry m / z 897 ^(M +)

(207) 8-O-stear oil-14-
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.92 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th H) 4.48 (1H, multiple line, J = 5.29 Hz, J = 2.96 Hz) (15th H) 4.06 (1H, double line) , J = 6.59 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (1,6,16 and 18) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1 .10 (3H, triplet, J = 7.0Hz) (H methyl group _{N-CH 2 CH 3) 0.96} (3H, triplet, J = 7.6Hz) (stearate The analysis following signal group terminated methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from stearic acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5, 131.7, 122.2, 113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82.3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 16,
6,1,14,15,13,18,3rd position C) 60.9,58.7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 6} ) EI- mass spectrometry m _{^{/ z 615 (M + -C 18}} H 36 O 2), 584
_{^{(M + -C 18 H 36 O}} 2 -CH 3 OH) 7) FD- Mass spectrometry m / z 899 ^(M +)

(208) 8-O-linolenoyl-14
Physical property values and analytical data of O-anisoylaconine 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CDCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.92 (2H, doublet, J = 8.90 Hz) (same as above) 5.36 (6H, multiplet) ) (H of the double bond of the linolenic acid residue) 4.84 (1H, doublet, J = 4.95 Hz) (H at position 14) 4.48 (1H, multiplet, J = 5.29 Hz, J = 2.96 Hz) (H at 15th position) 4.06 (1H, doublet, J = 6.59 Hz) (H at 6th position) 3.85 (3H, singlet) (methoxy group of anisoyl group) H) 3.75 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) line) (same as above) 3.15 (3H, unit weight line) (same as above) 1.10 (3H, triplet, J = 7.0Hz) (N- CH 2 CH 3 H-methyl group 0.96 (3H, triplet, J = 7.6 Hz) shows an analysis following signals (linolenic acid residue terminal methyl ^{H) 5) 13} C nuclear magnetic resonance spectrum _{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from linolenic acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5, 131.7, 122.2, 113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82.3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 1
6,6,1,14,15,13,18,3rd position C) 60.9,58.7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 6} ) EI- mass spectrometry m _{^{/ z 615 (M + C 18}} H 30 O 2), 584 (M
_{^{+ -C 18 H 30 O 2 -CH}} 3 OH) 7) FD- Mass spectrometry m / z 893 ^(M +)

(209) 8-O-lauroyl-14-O
-Physical properties and analytical data of anisoyl aconin 1) Properties and solubility A colorless oily compound, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3500, 2940 and 1715 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ ppm). 7.97 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.92 (2H, double line, J = 8.90 Hz) (same as above) 4.84 (1H, double) Line, J = 4.95 Hz) (14th H) 4.48 (1H, multiple line, J = 5.29 Hz, J = 2.96 Hz) (15th H) 4.06 (1H, double line) , J = 6.59 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (1,6,16 and 18) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1 .10 (3H, triplet, J = 7.0Hz) (H methyl group _{N-CH 2 -CH 3) 0.96} (3H, triplet, J = 7.6Hz) (lauric acid Shows a partial prayer next signal at a terminal of the group methyl H) 5) @ 13 C nuclear magnetic resonance spectrum ^{(CDCl 3) (δ ppm)} . 175.0 (C of carbonyl group derived from lauric acid residue at position 8) 165.6 (C of carbonyl group derived from anisoyl group at position 14) 163.5, 131.7, 122.2, 113.8
(C of anisoyl group) 91.7, 90.0, 83.3, 82.3, 78.9,
78.5, 76.7, 74.0, 71.1 (8, 16,
6,1,14,15,13,18,3rd position C) 60.9,58.7,58.2,56.3 (16,1
C methoxy group attached at position 8,6,1) 55.4 (C methoxy group anisoyl group) 14.2 (C methyl group _{N-CH 2 CH 3) 6} ) EI- mass spectrometry m _{^{/ z 615 (M + -C 12}} H 24 O 2), 584
_{^{(M + -C 12 H 24O 2}} -CH 3 OH) 7) FD- Mass spectrometry m / z 815 ^(M +)

(210) Physical property values and analytical data of 3-O-benzoyl mesaconitine 1) Properties and solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) [α] ¹⁸ = + 6.36 (CHCl ₃ , C = 1.1
0) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3470, 2900 and 1705 cm ^-1 . 4) UV absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (δ, ppm) are shown. 7.42-8.0
5 (10H, m) H of the benzoyl group bonded to the 3-position and 14-position 5.17 (1H, multiplet, J = 11.87 Hz, 5.93 Hz) (H at the 3-position) 4.89 (1H, Double line, J = 4.95 Hz) (14th H) 4.48 (1H, multiple line, J = 5.28 Hz, 2.97 Hz) (15th H) 4.11 (1H, double line) , J = 6.93 Hz) (H at position 6) 3.74 (3H, singlet) (H of methoxy group bonded at positions 1, 6, 16 and 18) 3.28 (3H, singlet. ) (same as above) 3.21 (3H, unit weight line) (same as above) 3.12 (3H, unit weight line) (same as above) 2.41 (3H, unit weight line) (N-CH ₃ in H ) 1.40 (3H, H) ⁶ methyl group of acetyl group attached to a single heavy line) (# ^{8) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ analysis 172 3 (C of carbonyl group derived from acetyl group bonded to position 8) 165.4 (C of carbonyl group derived from benzoyl group bonded to position 14) 166.0 (carbonyl derived from benzoyl group bonded to position 3) C) 133.1, 132.7, 130.5, 129.8, 1
29.5, 129.4, 128.8, 128.3 (C 91.7, 90.1, 83.3, 82.0, 78.7, derived from a benzoyl group bonded to the 3- and 14-positions)
74.1, 71.8, 71.5 (8, 16, 1, 6,
C at positions 14, 15, 13, 3, and 18) 61.0, 58.7, 58.3, 56.6 (16, 1
Methoxy group attached at position 8,6,1 C) 42.5 (C methyl group C) 21.3 (acetyl group N-CH ₃ group) 7) FD-mass spectrometry m / z = 735 (M ⁺ )

(211) Physical property values and analytical data of 3-O-benzoylaconitine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) [α] _D ¹⁸ = + 4.69 (C: 0.98, CHC
l ₃ ) 3) Infrared absorption spectrum (KBr) analysis Shows absorption maximum at 3460, 2900, 1705 cm ^-1 4) Ultraviolet absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (δ, ppm) are shown. 7.42-8.05 (10H, multiplet) (H of benzoyl group bonded to the 3rd and 14th positions) 5.19 (1H, multiplet, J = 12.0Hz, 5.94Hz) (3rd position H) 4.89 (1H, double line, J = 4.9 Hz) (H at 14th) 4.48 (1H, multiple lines, J = 5.28 Hz, 2.96 Hz) (H at 15th) 4.12 (1H, doublet, J = 6.93 Hz) (H at position 6) 3.75 (3H, singlet) (H3 of the methoxy group bound at positions 1, 6, 16 and 18) .26 (3H, singlet) (same as above) 3.21 (3H, singlet) (same as above) 3.12 (3H, singlet) (same as above) 1.40 (3H, singles) ) (8-methyl group of acetyl group attached to position H) 1.15 (3H, triplet, J = 6.95 Hz) (methyl group N- ethyl group H) ^{6) 13} C nuclear Air resonance spectrum (CDCl ₃₎ (C of a carbonyl group derived from a benzoyl group bound to 14-position) 165.5 (C of a carbonyl group derived from the acetyl group bonded to the 8-position) analysis 172.3 166.0 (3-position 133.1, 132.7, 130.5, 129.8, 1 of a carbonyl group derived from a benzoyl group bonded to
29.5, 129.4, 128.8, 128.3 (3
C) 91.9, 90.1, 83.4, 81.9, 78.7,
74.1, 72.0, 71.6 (8, 16, 1, 6,
C at positions 14, 15, 13, 3, and 18) 61.0, 58.9, 58.7, 56.6 (16, 1
Methoxy group C bonded at 8, 6, 1 position) 21.3 (acetyl group methyl group C) 13.4 (N. ethyl group methyl group C) 7) FD-mass spectrum analysis m / z = 749 (M ⁺ )

(212) Physical property values and analytical data of 3-O-benzoyl jesaconitine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) [α] _D ¹⁸ = 13.1 (C = 0.61, CHC
l ₃ ) 3) Infrared absorption spectrum (KBr) analysis Shows absorption maximum at 3450, 2900, 1703 cm ^-1 4) Ultraviolet absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (6 ppm) are shown. 7.43-8.05 (5H, multiplet) (H 7.99 of benzoyl group bonded at position 3 (2H, doublet, J = 8.91 Hz) (H of anisoyl group bonded at position 14) 6.94 (2H, double line, J = 8.91 Hz) (same as above) 5.19 (1H, multiple line, J = 12.2 Hz, 5.35 Hz) (3rd place H) 4.86 ( 1H, double line, J = 5.28 Hz) (14th H) 4.48 (1H, multiple line, J = 5.11 Hz, 2.96 Hz) (15th H) 4.12 (1H, 2H) Heavy line, J = 6.93 Hz) (H at position 6) 3.87 (3H, singlet) (H of methoxy group of anisoyl group) 3.74 (3H, singlet) (1,6,16) And H of the methoxy group bonded to position 18) 3.26 (3H, singlet) (same as above) 3.24 (3H, singlet) (same as above) 3.12 (same as above) H, singlet) (same as above) 1.44 (3H, singlet) (H of methyl group of acetyl group bonded to 8-position) 1.15 (3H, triplet J = 6.95 Hz) (N -H of methyl group of ethyl group) 6) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 172.4 (C of carbonyl group derived from acetyl group bonded to 8-position) 165.5 (Anisoyl bonded to 14-position Group of carbonyl group derived from group) 165.7 (C of carbonyl group derived from benzoyl group bonded to position 3) 122.6, 131.6, 113.8, 163.4 (C of anisoyl group) 132. 7, 130.6, 129.4, 128.8 (C derived from benzoyl group) 91.9, 90.1, 83.5, 81.9, 78.7,
78.5, 74.1, 72.0, 71.6 (8, 1
6,1,6,14,15,13,3,18 C) 6
1.0, 58.7, 58.3, 56.3 (16, 18,
6, C of the methoxy group bonded to the 1-position) 55.4 (C of the methoxy group of the anisoyl group) 21.4 (C of the methyl group of the acetyl group) 7) FD-mass spectrum analysis m / z = 779 (M ⁺ )

(213) Physical Properties and Analytical Data of 3-O-Anisoyl Mesaconitine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) [α] _D ¹⁸ = + 7.6 ° (C = 0.5, CHCl
₃ ) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3480, 2920 and 1705 cm ^-1 . 4) UV absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (δ, ppm) are shown. 7.43-8.05 (5H, multiplet) H of a benzoyl group bonded to position 14 8.00 (2H, doublet, J = 8.91 Hz) (H of anisoyl group bonded to position 3) 6 .93 (2H, double line, J = 8.91 Hz) (same as above) 5.14 (1H, multiple line, J = 12.2 Hz, 5.35 Hz) (third-order H) 4.89 (1H, Double line, J = 5.28 Hz) (14th H) 4.48 (1H, multiple line, J = 5.11 Hz, 2.96 Hz) (15th H) 4.11 (1H, double line) , J = 6.93 Hz) (H at position 6) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.74 (3H, singlet) (1,6,16 and 18) 3.28 (3H, singlet) (same as above) 3.21 (3H, singlet) (same as above) 3.11 (3) , Unit weight line) (Same as above) 2.41 (3H, unit weight line) (the N- methyl H) 1.40 (3H, single heavy line) (the methyl group of acetyl group H) ^{6) 13} C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 172.3 (C of carbonyl group derived from acetyl group bonded to position 8) 165.3 (C of carbonyl group derived from benzoyl group bonded to position 14) 166.0 (3 C) 122.9, 131.4, 113.5, 163.4 (C derived from anisoyl group) 133.1, 129.8, 129.5, 128.5 (C derived from benzoyl group) 91.7, 90.1, 83.3, 82.0, 78.7,
74.1, 71.6, 71.4 (8, 16, 1, 6,
C at positions 14, 15, 13, 3, and 18) 61.0, 58.7, 58.3, 56.6 (16, 1
C, the methoxy group bonded to the 8, 6, 1-position) 55.4 (C, the methoxy group of the anisoyl group) 21.3 (C, the methyl group of the acetyl group) 42.5, (C of the N-methyl group) 7 ) FD-mass spectrometry m / z = 765 (M ⁺ )

(214) Physical Properties and Analytical Data of 3-O-Anisoylaconitine 1) Properties and solubility A colorless non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, Soluble in dimethyl sulfoxide, insoluble in hexane and water. 2) [α] _D ¹⁸ = + 4.08 (C = 1.03, CHC
l ₃ ) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450, 2930 and 1703 cm ⁻¹ . 4) UV absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (δ, ppm) are shown. 7.43-8.05 (5H, multiplet) (H of benzoyl group attached at position 14) 8.00 (2H, doublet, J = 8.91 Hz) (H of anisoyl group attached at position 3) 6.94 (2H, double line, J = 8.91 Hz) (same as above) 5.15 (1H, multiple line, J = 12.3 Hz, 5.61 Hz) (third-order H) 4.89 ( 1H, double line, J = 5.28 Hz) (14th H) 4.48 (1H, multiple line, J = 5.11 Hz, 2.96 Hz) (15th H) 4.11 (1H, 2H) Heavy line, J = 6.93 Hz) (H at position 6) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.74 (3H, singlet) (1,6,16) And H of the methoxy group bonded to position 18) 3.26 (3H, singlet) (same as above) 3.21 (3H, singlet) (same as above) 3.12 (same as above) 1.40 (3H, singlet) (H of methyl group of acetyl group bonded to the 8-position) 1.15 (3H, triplet, J = 6.95 Hz) H) 6) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of methyl group of N-ethyl group 172.3 (C of carbonyl group derived from acetyl group bonded to 8-position) 165.2 (bonded to 14-position Carbonyl group derived from benzoyl group C) 166.0 (C derived from anisoyl group bonded to the 3-position) 123.0, 131.4, 113.5, 163.2 (C derived from anisoyl group) 133 , 1,129.8,129.5,128.5 (C derived from benzoyl group) 91.9,90.1,83.5,82.0,78.7,
74.1, 71.6 (8, 16, 1, 6, 14, 15,
(C at positions 13, 3, 18) 61.0, 58.7, 58.3, 56.3 (16, 1
C) of methoxy group bonded to 8, 6, 1 position 55.4 (C of methoxy group of anisoyl group) 21.3 (C of methyl group of acetyl group) 7) FD-mass spectrum analysis m / z = 779 (M)

(215) Physical property values and analytical data of 3-O-anisoylsesaconitine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, It is soluble in pyridine and dimethylsulfoxide and insoluble in hexane and water. 2) [α] _D ¹⁸ = + 24.0 (C = 0.3, CHCl
₃ ) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3470, 2910 and 1705 cm ^-1 . 4) UV absorption spectrum (EtOH) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals (δ, ppm) are shown. 7.99 (4H, doublet, J = 8.91 Hz) (H of the anisoyl group bonded to the 3,14 position) 6.94 (4H, doublet, J = 8.91 Hz) (Id.) 5.17 (1H, multiple line, J = 12.1 Hz, 5.35 Hz) (3rd place H) 4.86 (1H, doublet, J = 5.28 Hz) (14th place H) 4.48 (1H, double line, J = 5.11 Hz, 2.96 Hz) (H at 15th position) 4.12 (1H, double line, J = 6.93 Hz) (H at 6th position) 3.86 (6H) , Singlet) (H of the methoxy group of the anisoyl group) 3.74 (3H, singlet) (H of the methoxy group bonded to the 1,6,16 and 18-positions) 3.26 (3H, singlet) 3.21 (3H, singlet) (same as above) 3.12 (3H, singlet) (same as above) 1.44 (3H, singlet) (bonded to position 8) Acetyl methyl group of H) 1.14 in (3H, triplet, J = 6.95Hz) (methyl group N- ethyl group ^{H) 6) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ analysis 172. 3 (C of carbonyl group derived from acetyl group bonded to 8-position) 165.2 (C of carbonyl group derived from anisoyl group bonded to 3-, 14-position) 165.6 (same as above)
113.5, 113.8, 123.1, 123.3, 1
31.4, 131.6, 163.2, 163.4 (C derived from anisoyl group) 91.9, 90.1, 83.5, 82.0, 78.7,
78.5, 74.1, 71.6 (8, 16, 1, 6,
(C at positions 14, 15, 13, 3, and 18) 61.0, 58.7, 58.3, 56.4 (16, 1
55.4 (of methoxy group of anisoyl group) 51.3 (of methoxy group of anisoyl group) 21.3 (C of methyl group of acetyl group) 7) FD-mass spectrum analysis m / z = 809 ( M ⁺ )

(216) Physical property values and analytical data of 8-O-methyl-14-O-benzoylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was formed of ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3420 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.43 (5H, multiplet) (H of benzoyl group) 4.86 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.60 (1H, doublet) , J = 5.60 Hz) (H at position 15) 4.07 (1H, double line, J = 6.27 Hz) (H at position 6) 3.76 (3H, singlet) (1,6,8) , H of the methoxy group at positions 16 and 18) 3.31 (3H, singlet) (same as above) 3.29 (6H, singlet) (same as above) 3.16 (3H, singlet) (same as above) 1.16 (3H, triplet, J = 6.93 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.0, 129.6, 128.3 (C of benzoyl group) 93.2, 83.0, 82.4, 82 , 1,79.2
77.2, 74.6, 71.3 (16, 6, 1, 8, 1
4,15,18,13,3rd position C) 62.3,59.0,58.5,55.7 (16,1
8,9,1 of the methoxy group bonded to 1,6,1 49.9 (C of the methoxy group bonded to the 8-position) 49.0 (C, of the methylene group of N-ethyl group) 13.0 (of the methylene group of N-ethyl group) C) 6) EI-mass spectrum analysis m / z 617 (M ⁺ )

(217) Physical property values and analytical data of 8-O-ethyl-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3400 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.83 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.56 (1H, doublet) , J = 5.93 Hz) (H at 15th) 4.09 (1H, double line, J = 6.59 Hz) (H at 6th) 3.75 (3H, singlet) (1,6,16) And H of the methoxy group at position 18) 3.31 (3H, singlet) (same as above) 3.27 (6H, singlet) (same as above) 1.13 (3H, triplet, J = 7.26 Hz) (H of methyl group of N-ethyl group) 0.59 (3H, triplet, J = 6.29 Hz) (H of methyl group of ethoxy group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.2, 129.6, 128.3 (C of benzoyl group) 93.2, 83.3, 82.3, 82 .2,79.4,
76.8, 74.7, 71.5 (16, 6, 1, 8,
14, 15, 18, 13, 3rd position C) 62, 3, 59.0, 58.5, 55.7 (16, 1
C, the methoxy group bonded to 8, 6, 1) 57.2 (C, the methylene group of the ethoxy group bonded to the 8-position) 48.9 (C, the methylene group of the N-ethyl group) 15.3 (the 8-position 13.1 (C of the methyl group of the N-ethyl group) 6) EI-mass spectrum analysis m / z 631 (M ⁺ )

(218) Physical properties and analytical data of 3-O-acetyl-8-O-methyl-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder of ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3400 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06.7.42 (5H, multiplet) (H of benzoyl group) 5.00 (1H, multiplet) (H at 3rd position) 4.84 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.57 (1H, doublet, J = 5.60 Hz) (H at 15th) 4.07 (1H, doublet, J = 6.27 Hz) (H at 6th) 3.75 (3H, singlet) (H of methoxy group at positions 1, 6, 8, 16, and 18) 3.30 (3H, singlet) (same as above) 3.27 (3H, singlet) ( 3.23 (3H, singlet) (same as above) 3.14 (3H, -I line) (same as above) 2.08 (3H, singlet) (methyl group of acetyl group bonded to the 3-position) of H) 1.16 (3H, triplet, J = 6.93Hz) (methyl group N- ethyl group ^{H) 5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ Shows signals for 析次 (δ, ppm). 170.0 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132.7, 130.1, 129.6, 128.3 (benzoyl C) 93.2, 83.0, 82.3, 81.9, 79.2
78.3, 77.0, 74.1, 71.7 (16, 6,
1,8,14,15,18,13,3rd position C) 62.3,59.0,58.5,55.7 (16,1
4,9.8 (C of the methoxy group bonded to the position 8) 49.8 (C of the methoxy group bonded to the position 8) 49.0 (C of the methylene group of the N-ethyl group) 21.2 (bonded to the position 3) 13.2 (C of N-ethyl methyl group) 6) EI-mass spectrometry m / z 659 (M ⁺ )

(219) Physical property values and analytical data of 3-O-acetyl-8-O-ethyl-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder of ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4,97 (1H, multiplet) (H at 3rd position) 4.82 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.53 (1H, doublet, J = 5.94 Hz) (H at 15th) 4.18 (1H, doublet, J = 6.59 Hz) (H at 6th) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.22 (3H, singlet) (same as above) 2.07 (3H, singlet) (H of methyl group of acetyl group bonded to the 3-position) 1.11 (3H, triplet, J = 7.09 Hz) ) (N-ethyl-H methyl group groups) 0.58 (3H, H methyl group triplet, J = 6,76Hz) (ethoxy group attached to the 8-position) ^{5) 1} C nuclear magnetic resonance spectrum (CDCl ₃₎ shows the analysis following signals (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132.7, 130.3, 129.6, 128.2 (benzoyl Group C) 93.6, 83.4, 82.3, 82.0, 79.5
78.5, 77.0, 74.8, 71.5 (16, 6,
1,8,14,15,18,13,3rd position C) 62.3,60.9,58.7,56.4 (16,1
Methoxy group C bonded to 8,6,1) 57.1 (ethoxy group methylene group C bonded to position 8) 49.1 (N-ethyl group methylene group C) 21.2 (position 3) 15.3 (C of methyl group of ethoxy group bonded to 8-position) 13.5 (C of methyl group of N-ethyl group) 6) EI-mass spectrum analysis m / Z 673 (M ⁺ )

(220) 3-O-acetyl-14-O-
Physical properties and analytical data of benzoyl aconine 1) Properties and solubility It is a colorless non-crystalline powder, soluble in ether, chloroform, benzene, ethanol, methanol, ethanol, ethyl acetate, pyridine, dimethyl sulfoxide, and in hexane and water. Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.98 (1H, multiplet) (H at 3rd position) 4.80 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.53 (1H, doublet, J = 5.94 Hz) (H at 15th) 4.18 (1H, doublet, J = 6.59 Hz) (H at 6th) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16, and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) ) 3.22 (3H, singlet) (same as above) 2.07 (3H, singlet) (H of methyl group of acetyl group bonded to 3-position) 1.11 (3H, triplet, J = 7. 09 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132, 7, 130.3, 129.6, 128.2 (benzoyl C) 90.7, 83.5, 82.4, 81.3, 79.5
78.5, 77.3, 74.8, 71.5 (16, 6,
1,15,14,8,18,13,3rd position C) 62.0,59.9,58.7,56.2 (16,1
8,9.1, C of a methoxy group bonded to 1,6,1 49.1 (C of a methylene group of an N-ethyl group) 21.2 (C of a methyl group of an acetyl group bonded to the 3-position) 13.5 (N- C) 6) EI-mass spectrum analysis m / z 645 (M ⁺ )

(221) Physical property values and analytical data of 8-O-methyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.10-7.45 (5H, multiplet) (H of benzoyl group) 4.48 (1H, doublet, J = 4.50 Hz) (H at 14th position) 4.06 (1H, doublet) , J = 6.27 Hz) (H at position 6) 3.64 (3H, singlet) (H at 1,6,8,16, and 18-position methoxy groups) 3.30 (6H, singlet) ( 3.29 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 2.37 (3H, singlet) (H of N-methyl group) 5) ¹³ C Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.1, 129.6, 128.3 (C of benzoyl group) 93.4, 83.1, 82.6, 82 .1,79.4,
77.5, 74.3, 71.4 (16, 6, 1, 8,
(C at 14, 15, 18, 13, 3rd position) 62.3, 59.1, 58.5, 56.3 (16, 1
C, the methoxy group bonded to 8, 6, 1) 49.7 (C, the methoxy group bonded to the 8-position) 42.4 (C, the N-methyl group) 6) EI-mass spectrum analysis m / z 603 ( M ⁺ ) 7) Elemental analysis Calculated C, 53.22; H, 6.70; N, 1.94.
_{(C 32 H 45 NO 10 ·} HClO 4 · H 2 O) Found C, 53.54; H, 6.62; N, 1.6

(222) Physical property values and analytical data of 8-O-ethyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.08-7.27 (5H, multiplet) (H of benzoyl group) 4.81 (1H, doublet, J = 4.70Hz) (H at 14th position) 4.54 (1H, doublet) , J = 6.10 HZ) (H at 15th position) 4.08 (1H, double line, J = 7.60 Hz) (H at 6th position) 3.73 (3H, singlet) (1,6,16) , And H of the methoxy group at position 18) 3.31 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 2 .34 (3H, singlet) (H of N-methyl group) 0.57 (3H, triplet, J = 6.00 Hz) (H of methyl group of ethoxy group bonded to the 8-position) 5) ¹³ C nucleus Magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.3, 129.6, 128.3
(C of benzoyl group) 93.4, 83.3, 82.7, 82.0, 79.4
78.3, 76.4, 74.7, 71.3 (16, 6,
1,8,14,15,18,13,3rd position C) 62.4,59.1,58.6,56.3 (16,1
C, a methoxy group bonded to 8, 6, 1) 57.1 (C, a methylene group of an ethoxy group bonded to the 8-position) 42.5 (C, a N-methyl group) 15.3 (C bonded to the 8-position C) 6) EI-mass spectrum analysis m / z 617 (M ⁺ ) 7) High-resolution mass spectrum analysis Calculated value: 617.320 (C ₃₃ H ₄₇ NO ₁₀ ) Actual value: 617.3321

(223) Physical properties and analytical data of 3-O-acetyl-8-O-methyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless, non-crystalline powder of ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3420 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.02-7.45 (5H, multiplet) (H of benzoyl group) 4.97 (1H, multiplet) (H at 3rd position) 4.85 (1H, doublet, J = 4.28 Hz) (H at 14th) 4.56 (1H, doublet, J = 5.90 Hz) (H at 15th) 4.16 (1H, doublet, J = 5.93HZ) (H at 6th) 3.74 (3H, -doublet) (H of methoxy group at 1,6,8,16, and 18 positions) 3.31 (3H, singlet) (same as above) 3.29 (3H, singlet) (Same as above) 3.23 (3H, singlet) (same as above) 3.14 (3H, singlet) (same as above) 2.09 (6H, singlet) (at H and 3rd position of N-methyl group) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis of the methyl group of the bound acetyl group. The following signals are shown (δ, ppm). 170.2 (C of carbonyl group of acetyl group bonded to 3-position) 166.2 (C of carbonyl group derived from benzoyl group at 14-position) 132.8, 13o. 2,129.7,128.3
(C of benzoyl group) 93.3, 83.0, 82.2, 81.9, 79.2
77.6, 77.0, 74.8, 71.5 (16, 6,
1,8,14,15,18,13,3rd position C) 62.2,58.8,56.6,50.1 (16,1
4,9.8 (C of methoxy group bonded to position 8) 49.8 (C of methoxy group bonded to position 8) 42.7 (C of N-methyl group) 21.2 (C, of acetyl group bonded to position 3) C) of methyl group 6) EI-mass spectrum analysis m / z 645 (M ⁺ )

(224) Physical properties and analytical data of 3-O-acetyl-8-O-ethyl-14-O-benzozomesaconin 1) Properties and solubility A colorless amorphous powder of ether, chloroform, Benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.96 (1H, multiplet) (C at position 3) 4.82 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.54 (1H, doublet, J = 5.94 Hz) (H at 15th) 4.14 (1H, doublet, J = 6.92 Hz) (H at 6th) 3.74 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.22 (3H, singlet) (same as above) 2.08 (6H, singlet) (H of methyl group of acetyl group and H of N-methyl group bonded to the 3-position) 0.57 (3H , triplet, J = 6.92Hz) (methyl group of ethoxy groups attached to the 8-position ^{H) 5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ analysis following sheet Shows a null (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132.8, 129.6, 128.2 (C of the benzoyl group) 93.3, 82.0, 79.3, 78.3, 77.0,
74.6, 71.4 (16, 6, 1, 8, 14, 15,
62.1, 58.8, 56.6 (C of methoxy group bonded to 16, 18, 6, 1) 57.1 (Methylene group of ethoxy group bonded to 8 position) C) 42.6 (C of N-methyl group) 21.2 (C of methyl group of acetyl group bonded to position 3) 15.2 (C of methyl group of ethoxy group bonded to position 8) 6) EI-mass spectrum analysis m / z 659 (M ^<+> )

(225) 3-O-acetyl-14-O-
Physical property values and analytical data of benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone, nityl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3420 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.43 (5H, multiplet) (H of benzoyl group) 4.96 (1H, multiplet) (H at 3rd position) 4.86 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.60 (1H, doublet, J = 5.60 Hz) (H at 15th) 4.07 (1H, doublet, J = 6.27 Hz) (H at 6th) 3.76 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) (same as above) 3.29 (6H, singlet) (same as above) 2.09 (6H, singlet) (H of acetyl group and H of N-methyl group bonded to 3-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) . 170.2 (carbonyl group C of acetyl group bonded to position 3) 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.0, 129.6, 128.3 (benzoyl group C) 91.0, 83.0, 82.4, 82.5, 79.3
77.2, 74.6, 71.3 (16, 6, 1, 15,
C at position 14, 8, 18, 13, 3) 62.3, 59.0, 58.5, 55.7 (16, 1
82.7 (C of the methyl group of the N-ethyl group) 21.3 (C of the methyl group of the acetyl group bonded to the 3-position) 6) EI-mass spectrum Analysis m / z 631 (M ⁺ )

(226) Physical property values and analysis data of 8-O-methyl-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, Acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) [α] _D ²⁴ = + 7.5 ° (c = 0.93, ethanol) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, double line, J = 8.90 Hz) (same as above) 4.55 (1H, double line) Line, J = 6.00 Hz) (H at position 14) 3.87 (3H, singlet) (H of methoxy group of anisoyl group) 3.64 (3H, singlet) (1,6,16,8 and H of the methoxy group at position 18) 3.31 (3H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 1.13 (3H, triplet, J = 7.26 Hz) (H of methyl group of N-ethyl group) 6) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 165.7 (C of carbonyl group derived from anisoyl group at position 14) 163.2, 131.6, 122.4, 113.5 (C of anisoyl group) 93.3, 83.1, 82.2, 82 .2,79.4,
76.9, 74.7, 71.5 (16, 6, 1, 8, 1
4,15,18,13,3rd position C) 62.3,59.0,58.4,55.6 (16,1
55.3 (C of anisoyl group methoxy group) 49.8 (C of methoxy group bonded to 8-position) 48.8 (of methylene group of N-ethyl group) C) 13.0 (C of methyl group of N-ethyl group) 7) EI-mass spectrum analysis m / z 647 (M ⁺ ) 8) High-resolution mass spectrum analysis Calculated value: 647.330 (C ₃₄ H ₄₉ NO) ₁₁ ),
Obtained: 647.328

(227) Physical properties and analytical data of 8-O-ethyl-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) [α] _D ²⁴ = + 5.8 ° (c = 1.80, ethanol) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1720 cm ⁻¹ . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, double line, J = 8.90 Hz) (same as above) 4.60 (1H, double) Line, J = 6.00 Hz) (H at position 14) 3.88 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (positions 1, 6, 16 and 18) 3.33 (3H, singlet) (same as above) 3.28 (6H, singlet) (same as above) 1.11 (3H, triplet, J = 7.00 Hz) (N- H of methyl group of ethyl group) 0.64 (3H, triplet, J = 6.00 Hz) (H of methyl group of ethoxy group bonded to the 8-position) 6) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.8 (C of carbonyl group derived from anisoyl group at position 14) 163.1, 131.6, 122.7, 113.6 (C of anisoyl group) 93.3, 83.4, 82.5, 82 .1,79.2
77.3, 74.2, 71.6 (16, 6, 1, 8,
(C at 14, 15, 18, 13, 3rd position) 62.3, 59.0, 58.5, 55.8 (16, 1
55.3 (C of anisoyl group methoxy group) 57.1 (C of ethoxy group methylene group bonded at the 8-position) 48.8 (of N-ethyl group) Methylene group C) 15.3 (methyl group C of ethoxy group bonded to the 8-position) 13.0 (methyl group C of N-ethyl group) 7) EI-mass spectrum analysis m / z 661 (M ⁺ ) 8) high resolution mass spectrum _{calcd: 661.349 (C 35 H 51 NO} 11),
Obtained value: 661.346

(228) Physical properties and analytical data of 3-O-acetyl-8-O-methyl-14-O-anisoylaconine 1) Properties and solubility A colorless, non-crystalline powder of ether, chloroform, benzene , Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, doublet, J = 8.90 Hz) (same as above) 4.95 (1H, multiplet) (H in 3rd place) 4.81 (1H, doublet, J = 4.95 Hz) (H in 14th place) 4.53 (1H, doublet, J = 5.94 Hz) (H in 15th place) 4.11 (1H, doublet, J = 6.60 Hz) (H at position 6) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.71 (3H, singlet) (H of the methoxy group at positions 1, 6, 16, 8 and 18) 3.30 (3H, singlet) (same as above) 3.25 (3H, singlet) (same as above) 3.22 (3H, singlet) 3.13 (3H, singlet) (same as above) 2.07 (3H, singlet) (H of methyl group of acetyl group bonded to the 3-position) 1.1 1 (3H, triplet, J = 7.26 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.3 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.0 (C of the carbonyl group derived from the anisoyl group at the 14-position) 163.2, 131.8, 122.8, 113.6 (Anisoyl Group C) 93.6, 83.3, 82.2, 79.2, 77.8,
77.0, 74.9, 71.3 (16, 6, 1, 8, 1
4,15,18,13,3-position C) 62.4,58.8,55.4 (C of methoxy group bonded to 16,18,6.1) 55.4 (C of anisoyl group methoxy group) 49.8 (C of the methoxy group bonded to the 8-position) 49.2 (C of the methylene group of the N-ethyl group) 21.3 (C of the methyl group of the acetyl group bonded to the 3-position) 13.5 ( methyl group of N- ethyl group C) 6) EI- mass spectrometry ^{m / z 689 (M +)} 7) high resolution mass spectrum _{calcd: 689.402 (C 36 H 51 NO} 12), found: 689.339

(229) Physical property values and analytical data of 3-O-acetyl-8-O-ethyl-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder of ether, chloroform, benzene , Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1705 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, double line, J = 8.90 Hz) (same as above) 4.96 (1H, multiple line) ) (3rd H) 4.81 (1H, doublet, J = 4.95 Hz) (14th H) 4.53 (1H, doublet, J = 5.94 Hz) (15th H) 4.11 (1H, doublet, J = 6.60 Hz) (H at position 6) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.22 (3H, singlet) (Id.) 2.08 (3H, singlet) (H of methyl group of acetyl group bonded to the 3-position) 1.13 (3H, triplet, J = 7.26 Hz) (N- H of methyl group of ethyl group) 0.64 (3H, triplet, J = 7.26 Hz) (H of methyl group of ethoxy group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.0 (C of the carbonyl group derived from the anisoyl group at the 14-position) 163.2, 131.7, 122.8, 113.6 (Anisoyl C) 93.5, 83.3, 82.1, 79.1, 78.3
77.0, 74.8, 71.7 (16, 6, 1, 8, 1
4,15,18,13,3 position C) 62.2,58.7,55.4 (C of methoxy group bonded to 16,18,6.1) 56.4 (C of methoxy group of anisoyl group) C) 57.1 (C of the methylene group of the ethoxy group bonded to the 8-position) 49.2 (C of the methylene group of the N-ethyl group) 21.2 (C of the methyl group of the acetyl group bonded to the 3-position) 15.4 (C of methyl group of ethoxy group bonded to 8-position) 13.3 (C of methyl group of N-ethyl group) 6) EI-mass spectrum analysis m / z 703 (M ⁺ ) 7) High resolution Mass spectrum analysis Calculated: 703.418 (C ₃₇ H ₅₃ NO ₁₂ ), found: 703.359

(230) 3-O-acetyl-14-O-
Physical Properties and Analytical Data of Anisoyl Aconin 1) Properties and Solubility A colorless non-crystalline powder containing ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3420 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, double line, J = 8.9 Hz) (H of anisoyl group) 6.89 (2H, double line, J = 8.9 Hz) (same as above) 4.97 (1H, double line) Line, J = 4.95 Hz) (H at 14th) 4.55 (1H, doublet, J = 5.60 Hz) (H at 15th) 4.07 (1H, doublet, J = 6. 27 Hz) (H at position 6) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.70 (3H, singlet) (Methoxy group of 1,6,8,16 and 18) H) 3.31 (3H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 3.24 (3H, singlet) (same as above) 1.16 (3H, triplet, same as above) J = 6.93 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, p pm). 170.3 (C of the carbonyl group of the acetyl group bonded to the 3-position) 165.9 (C of the carbonyl group derived from the anisoyl group at the 14-position) 163.5, 131.8, 122.1, 113.6 (Anisoyl C) 90.7, 83.5, 82.4, 81.9, 79.5
78.6, 77.3, 78.8, 71.3 (16, 6,
1,15,14,8,18,13,3 position C) 62.3,58.7,55.4 (C of methoxy group bonded to 16,18,6.1) 56.4 (Anisoyl group 49.0 (C of the methylene group of the N-ethyl group) 21.1 (C of the methyl group of the acetyl group bonded to the 3-position) 13.0 (C of the methyl group of the N-ethyl group) 6) EI-mass spectrometry m / z 675 (M ^<+> )

(231) Physical property values and analytical data of 8-O-methyl-14-O-benzoylhypaconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1710 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.10-7.45 (5H, multiplet) (H of benzoyl group) 4.70 (1H, doublet, J = 4.50 Hz) (H at 14th position) 4.54 (1H, doublet) , J = 5.93 Hz) (H at 15th position) 4.06 (1H, double line, J = 6.70 Hz) (H at 6th position) 3.64 (3H, singlet) (1,6,8) Methoxy groups H at positions 16 and 18) 3.30 (6H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 3.15 (3H, singlet) (same as above) 2 .37 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.1, 129.6, 128.3 (C of benzoyl group) 93.4, 83.1, 82.6, 82 .1,79.4,
77.5, 74.3 (16, 6, 18, 14, 15, 1
C, 8,13) 62.3,59.1,58.5,56.3 (16,1
C, a methoxy group bonded to the 8, 6, 1 position) 49.9 (C, a methoxy group bonded to the 8 position) 42.4 (C, an N-methyl group) 6) EI-mass spectrum analysis m / z 587 ( M ⁺ )

(232) Physical property values and analytical data of 8-O-ethyl-14-O-benzoylhypaconin 1) Properties and solubility A colorless non-crystalline powder, which is ether, chloroform, benzene, ethanol, methanol, acetone. ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.07-7.26 (5H, multiplet) (H of benzoyl group) 4.82 (1H, doublet, J = 4.50 Hz) (H at 14th position) 4.55 (1H, doublet) , J = 5.93 Hz) (H at 15th position) 4.08 (1H, double line, J = 6.70 Hz) (H at 6th position) 3.73 (3H, singlet) (1,6,16) And methoxy group H at position 18) 3.28 (6H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 2.34 (3H, singlet) (H of N-methyl group) ) 0.58 (1H, triplet, J = 6.00 Hz) (C of ethoxy group of the ethoxy group bonded to the 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis , Ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.3, 129.6, 128.3 (C of benzoyl group) 93.5, 83.2, 82.6, 81 .9, 79.4,
78.3, 76.4, 74.7 (16, 6, 18, 1
C at 4,15,13th position) 62.4,59.1,58.6,56.3 (16,1
C, a methoxy group bonded to the 8, 6, 1 position) 57.2 (methylene group, C, an ethoxy group bonded to the 8 position) 42.5 (C, an N-methyl group) 15.3 (a ethoxy group bonded to the 8 position) 6) EI-mass spectrometry m / z 599 (M ⁺ )

(233) Physical property values and analytical data of 8-O-amyl-14-O-benzoyl aconine 1) Properties and solubility A colorless non-crystalline powder, which was obtained by ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis 3400, showing maximum absorption at 1715 cm ^-1 3) Ultraviolet absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.83 (1H, doublet, J = 4.95 Hz) (H at 14th position) 4.56 (1H, doublet) , J = 5.93 Hz) (H at 15th) 4.09 (1H, double line, J = 6.59 Hz) (H at 6th) 3.75 (3H, singlet) (1,6,16) And H of the methoxy group at position 18) 3.31 (3H, singlet) (same as above) 3.27 (6H, singlet) (same as above) 1.13 (3H, triplet, J = 7.26 Hz) (H of methyl group of N-ethyl group) 0.57 (3H, triplet, J = 6.29 Hz) (C of methyl group of amyl group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis The following signals are shown (δ, ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.2, 129.6, 128.3 (C of benzoyl group) 93.2, 83.3, 82.3, 82 .2,79.4,
76.8, 74.7, 71.5 (16, 6, 1, 8,
14, 15, 18, 13, 3rd position C) 62.3, 59.0, 58.5, 55.7 (16, 1
57.5 (C of amyl group of methylene group bonded to position 8) 48.9 (C of N-ethyl group of methylene group) 15.0 (position of 8) 13.1 (C of methyl group of N-ethyl group) 6) EI-mass spectrum analysis m / z 675 (M ⁺ )

(234) Physical properties and analytical data of 3-O-acetyl-8-O-amyl-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder of ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.97 (1H, multiplet) (H at 3rd position) 4.82 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.53 (1H, doublet, J = 5.94 Hz) (H at 15th) 4.18 (1H, doublet, J = 6.59 Hz) (H at 6th) 3.73 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.22 (3H, singlet) (same as above) 2.07 (3H, singlet) (H of methyl group of acetyl group bonded to the 3-position) 1.11 (3H, triplet, J = 7.09 Hz) ) (H of methyl group of N-ethyl group) 0.55 (3H, triplet, J = 6.76 Hz) (H of methyl group of amyl group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132.7, 130.3, 129.6, 128.2 (benzoyl Group C) 93.6, 83, 4, 82.3, 82.0, 79.5
78.5, 77.0, 74.8, 71.5 (16,
6,1,8,14,15,18,13,3rd position C) 62.3,60.9,58.7,56.4 (16,1
Methoxy group C bonded to 8,6,1) 57.0 (amyl group methylene group C bonded to position 8) 49.1 (N-ethyl group methylene group C) 21.2 (position 3 15.0 (C of the methyl group of an amyl group bonded to the 8-position) 13.5 (C of the methyl group of an N-ethyl group) 6) EI-mass spectrum analysis m / Z 717 (M ⁺ )

(235) Physical Properties and Analytical Data of 8-O-Amyl-14-O-benzoylmesaconin 1) Properties and Solubility A colorless, non-crystalline powder, which was prepared from ether, chloroform, benzene, ethanol, methanol, acetone, Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.08-7.27 (5H, multiplet) (H of benzoyl group) 4.81 (1H, doublet, J = 4.70Hz) (H at 14th position) 4.54 (1H, doublet) , J = 6.10 Hz) (H at 15th) 4.08 (1H, double line, J = 7.60 Hz) (H at 6th) 3.73 (3H, singlet) (1,6,16) And H of the methoxy group at position 18) 3.31 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 34 (3H, singlet) (H of N-methyl group) 0.55 (3H, triplet, J = 6.00 Hz) (H of amyl methyl group bonded to the 8-position) 5) ¹³ C nucleus Magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.3, 129.6, 128.3 (C of benzoyl group) 93.4, 83.3, 82.7, 82 0.0, 79.4,
78.3, 76.4, 74.7, 71.3 (16, 6,
1,8,14,15,18,13,3rd position C) 62.4,59.1,58.6,56.3 (16,1
Methoxy group C bonded to 8,6,1) 57.0 (amyl group methylene group C bonded to position 8) 42.5 (N-methyl group C) 15.1 (bonded to position 8) C) 6) EI-mass spectrum analysis m / z 661 (M ⁺ )

(236) Physical properties and analytical data of 3-O-acetyl-8-O-amyl-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder of ether, chloroform, benzene, Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.06-7.41 (5H, multiplet) (H of benzoyl group) 4.96 (1H, multiplet) (C at position 3) 4.82 (1H, doublet, J = 4.95 Hz) (H at 14th) 4.54 (1H, doublet, J = 5.94 Hz) (H at 15th) 4.14 (1H, doublet, J = 6.92 Hz) (H at 6th) 3.74 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.22 (3H, singlet) (same as above) 2.08 (6H, singlet) (H of methyl group of acetyl group and H of N-methyl group bonded to the 3-position) 0.55 (3H, triplet) line, J = 6.92Hz) (H of methylation group amyl group attached to the 8-position) ^{5) 13} C nuclear magnetic resonance spectrum (CDCl ₃₎ analysis following signaling Shows the Le (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.2 (C of the carbonyl group derived from the benzoyl group at the 14-position) 132.8, 129.6, 128.2 (C of the benzoyl group) 93.3, 82.0, 79.3, 78.3, 77.0,
74.6, 71.4 (16, 6, 1, 8, 14, 15,
62.1, 58.8, 56.6 (C of methoxy group bonded to 16, 18, 6, 1) 57.0 (Methylene group of amyl group bonded to 8 position) C) 42.6 (C of N-methyl group) 21.2 (C of methyl group of acetyl group bonded to the 3-position) 15.2 (C of amino group of amyl group bonded to the 8-position) 6) EI-mass spectrum analysis m / z 703 (M ⁺ )

(237) Physical property values and analytical data of 8-O-amyl-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, double line, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, double line, J = 8.90 Hz) (same as above) 4.60 (1H, double) Line, J = 6.00 Hz) (H at position 14) 3.88 (3H, singlet) (H of methoxy group of anisoyl group) 3.75 (3H, singlet) (positions 1, 6, 16 and 18) 3.33 (3H, singlet) (same as above) 3.28 (6H, singlet) (same as above) 1.11 (3H, triplet, J = 7.00 Hz) (N- H of methyl group of ethyl group) 0.54 (3H, triplet, J = 6.00 Hz) (H of methyl group of amyl group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis shows the following signals (δ, ppm). 165.8 (C of carbonyl group derived from anisoyl group at position 14) 163.1, 131.6, 122.7, 113.6 (C of anisoyl group) 93.3, 83.4, 82.5, 82 .1,79.2
77.3, 74.2, 71.6 (16, 6, 1, 8, 1
4,15,18,13,3rd position C) 62.3,59.0,58.5,55.8 (16,1
55.3 (C of anisoyl group methoxy group) 57.1 (C of an amyl group methylene group bonded to the 8-position) 48.8 (C of the methylene group bonded to the 8-position) Methylene group C) 15.3 (amyl group methyl group C bonded to the 8-position) 13.0 (N-ethyl group methyl group C) 6) EI-mass spectrum analysis m / z 705 (M ⁺ )

(238) Physical property values and analytical data of 3-O-acetyl-8-O-amyl-14-O-anisoylaconine 1) Properties and solubility A colorless amorphous powder of ether, chloroform and benzene , Ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1705 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H NMR spectrum (CDCl ₃ ): The following signals are shown (δ, ppm). 7.99 (2H, doublet, J = 8.90 Hz) (H of anisoyl group) 6.93 (2H, doublet, J = 8.90 Hz) (same as above) 4.96 (1H, multiplet) (H in 3rd place) 4.81 (1H, doublet, J = 4.95 Hz) (H in 14th place) 4.53 (1H, doublet, J = 5.94 Hz) (H in 15th place) 4.11 (1H, doublet, J = 6.60 Hz) (H at position 6) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.73 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 3.22 (3H, singlet) (Id.) 2.08 (3H, singlet) (H of methyl group of acetyl group bonded to the 3-position) 1.13 (3H, triplet, J = 7.26 Hz) (N- H of methyl group of ethyl group) 0.55 (3H, triplet, J = 7.26 Hz) (H of methyl group of amyl group bonded to 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.2 (C of the carbonyl group of the acetyl group bonded to the 3-position) 166.0 (C of the carbonyl group derived from the anisoyl group at the 14-position) 163.2, 131.7, 122.8, 113.6 (Anisoyl C) 93.5, 83.3, 82.1, 79.1, 78.3
77.0, 74.8, 71.7 (16, 6, 1, 8, 1
4,15,18,13,3 position C) 62.2,58.7,55.4 (C of methoxy group bonded to 16,18,6.1) 56.4 (of methoxy group of anisoyl group) C) 57.1 (C of the methylene group of the ethoxy group bonded to the 8-position) 49.2 (C of the methylene group of the N-ethyl group) 21.2 (C of the methyl group of the acetyl group bonded to the 3-position) 15.1 (C of the methyl group of the amyl group bonded to the 8-position) 13.3 (C of the methyl group of the N-ethyl group) 6) EI-mass spectrum analysis m / z 733 (M ⁺ )

(239) Physical property values and analytical data of 8-O-amyl-14-O-benzoylhypaconin 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, acetone ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.07-7.26 (5H, multiplet) (H of benzoyl group) 4.82 (1H, doublet, J = 4.50 Hz) (H at 14th position) 4.55 (1H, doublet) , J = 5.93 Hz) (H at 15th position) 4.08 (1H, double line, J = 6.70 Hz) (H at 6th position) 3.73 (3H, singlet) (1,6,16) And methoxy group H at position 18) 3.28 (6H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 2.34 (3H, singlet) (H of N-methyl group) ) 0.55 (1H, triplet, J = 6.00 Hz) (C of the ethoxy group of the amyl group bonded to the 8-position) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. , Ppm). 166.1 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.3, 129.6, 128.3 (C of benzoyl group) 93.5, 83.2, 82.6, 81 .9, 79.4,
78.3, 76.4, 74.7 (16, 6, 18, 1
C at 4,15,18,13) 62.4,59.1,58.6,56.3 (16,1
Methoxy group C bonded to the 8,6,1 position) 57.0 (methylene group C of the amyl group bonded to the 8 position) 42.5 (C of the N-methyl group) 15.0 (amyl bonded to the 8 position Methyl group C) 6) EI-mass spectrum analysis m / z 643 (M ⁺ )

(240) Physical property values and analytical data of 16-epi-pyroaconitine 1) Solubility Soluble in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl sulfoxide, and dissolved in hexane and water. Insoluble. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 to 7.94 (2H, multiplet) (H of benzoyl group) 7.53 to 7.35 (3H, multiplet) (same as above) 5.44 (1H, doublet, J = 4. 93 Hz) (β-H at position 14) 3.81 (3H, singlet) (H of α-methoxy group at position 16) 3.32 (3H, singlet) (methoxy at positions 1,6 and 18) H) 3.28 (3H, singlet) (same as above) 3.25 (3H, singlet) (same as above) 1.03 (3H, triplet, J = 7.00 Hz) (methyl of N-ethyl group) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.7 (C of carbonyl group at position 15) 165.9 (C of carbonyl of benzoyl group) 133.2, 129.8 (2C), 129.6, 12
8.6 (2C) (C of benzoyl group) 86.2, 84.0, 83.6, 78.6, 77.2,
77.0, 71.7 (16, 6, 1, 14, 18, 1
3,3 position C) 49.0 (N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) EI-mass spectrometry m / z 585 (M ⁺ ) 7) [Α] _D ²⁵ = -64.3． (c = 0.23, ethanol)

(241) Physical properties and analytical data of pyroaconitine 1) Solubility Soluble in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.97 to 7.94 (2H, multiplet) (H of benzoyl group) 7.53 to 7.30 (3H, multiplet) (same as above) 5.18 (1H, doublet, J = 3. 97 Hz) (β-H at position 14) 3.64 (3H, singlet) (H of β-methoxy group at position 16) 3.30 (3H, singlet) (methoxy at positions 1,6 and 18) H) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 1.03 (3H, triplet, J = 7.0 Hz) (methyl of N-ethyl group) H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.8 (C of carbonyl group at position 15) 166.9 (C of carbonyl of benzoyl group) 133.0, 129.7 (2C), 129.6, 12
8.5 (2c) (C of besozoyl group) 89.2, 84.0, 83.5, 79.5, 77.2,
77.0, 71.4 (16, 6, 1, 14, 18, 1
3,3 position C) 49.0 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) EI-mass spectrometry m / z 585 (M ⁺ ) 7) [Α] _D ²⁵ = + 21.8 ゜ (c = 0.22, ethanol)

(242) Physical properties and analytical data of 16-epi-pyrromesaconitine 1) Solubility Soluble in ether, chloroform, benzene, ethanol, methanol, acetone, nityl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.10 to 8.02 (2H, multiplet) (H of benzoyl group) 7.58 to 7.40 (3H, multiplet) (same as above) 5.44 (1H, doublet, J = 4. 92 Hz) (β-H at position 14) 3.79 (3H, singlet) (H of α-methoxy group at position 16) 3.27 (3H, singlet) (methoxy at positions 1,6 and 18) H) 3.19 (6H, singlet) (same as above) 2.35 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. (Δ, ppm). 211.8 (C of carbonyl group at position 15) 166.0 (C of carbonyl of benzoyl group) 133.0, 129.8 (2C), 129.5, 12
8.5 (2C) (C of benzoyl group) 86.2, 84.0, 83.5, 78.6, 77.2,
77.0, 71.6 (16, 6, 1, 14, 18, 1
3,3 position C) 42.4 (N-methyl group C) 6) EI-mass spectrum analysis m / z 571 (M ⁺ ) 7) [α] _D ²⁵ = −79.5． (c = 0) .44, ethanol)

(243) Physical properties and data of pyromesaconitine 1) Solubility It is soluble in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.10 to 8.02 (2H, multiplet) (H of benzoyl group) 7.58 to 7.40 (3H, multiplet) (same as above) 5.20 (1H, doublet, J = 4. 0 Hz) (β-H at position 14) 3.62 (3H, singlet) (H of β-methoxy group at position 16) 3.26 (3H, singlet) (methoxy at positions 1,6 and 18 H) 3.20 (6H, singlet) (same as above) 2.35 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. (Δ, ppm). 211.7 (C of carbonyl group at position 15) 165.9 (C of carbonyl of benzoyl group) 133.0, 129.7 (2c), 129.4, 12
8.5 (2C) (C of benzoyl group) 89.3, 84.1, 83.6, 78.7, 77.1,
77.0, 71.5 (16, 6, 1, 14, 18, 1
3) C) 42.5 (C of N-methyl group) 6) EI-mass spectrum analysis m / z 571 (M ⁺ ) 7) [α] = + 15.4１５ (c = 0.48, ethanol )

(244) Physical properties and analytical data of 16-epi-pyrohypaconitine 1) Solubility Soluble in ether, chloroform, benzene, ethanol, methanol, acetone, nityl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water It is. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.10 to 7.26 (5H, multiplet) (H of benzoyl group) 5.44 (1H, doublet, J = 4.91 Hz) (β-H at position 14) 3.81 (3H, singlet) 1.) (H of α-methoxy group at position 16) 3.34 (6H, singlet) (H of methoxy group at positions 1, 6, and 18) 3.18 (3H, singlet) (same as above) 35 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.8 (C of carbonyl group at position 15) 166.0 (C of carbonyl of benzoyl group) 133.2, 129.6, 128.6 (2C), 12
9.9 (2C) (C of benzoyl group) 86.3, 86.0, 84.0, 81.4, 78.9,
77.0 (C at 16,1,6,18,14,13 position) 42.6 (C of N-methyl group) 6) EI-mass spectrum analysis m / z 555 (M ⁺ ) 7) [α] _D ²⁵ = −65.0 ° (c = 0.18, ethanol)

(245) Physical property values and analytical data of pyrohypaconitine 1) Solubility Soluble in ether, chloroform, benzene, ethanol, methanol, acetone, nitrile acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.08 to 7.25 (5H, multiplet) (benzoyl group H) 5.20 (1H, doublet, J = 4.0 Hz) (14-position β-H) 3.64 (3H, singlet) 1.) (H of β-methoxy group at position 16) 3.34 (6H, singlet) (H of methoxy group at positions 1, 6, and 18) 3.18 (3H, singlet) (ibid.) 35 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.7 (C of carbonyl group at position 15) 166.1 (C of carbonyl of benzoyl group) 133.2, 129.9 (2C), 129.6, 12
8.6 (2C) (C of benzoyl group) 89.3, 85.9, 84.0, 81.4, 78.9,
77.0 (C at 16,1,6,18,14,13 position) 42.6 (C of N-methyl group) 6) EI-mass spectrum analysis m / z 555 (M ⁺ ) 7) [α] _D ²⁵ = + 15.6 ゜ (c = 0.18, ethanol)

(246) Physical properties and analytical data of 16-epi-pyrogesaconitine 1) Properties and solubility Colorless needles of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3456 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.93 (2H, doublet, J = 8.91) (H of anisoyl group) 6.94 (2H, doublet, J = 8.91) (same as above) 5.39 (1H, doublet) Line, J = 4.95 Hz) (β-H at position 14) 3.87 (3H, singlet) (H of methoxy group of anisoyl group) 3.80 (3H, singlet) (α-methoxy at position 16) H) 3.30 (3H, singlet) (H of methoxy group at positions 1, 6 and 18) 3.26 (6H, singlet) (same as above) 1.05 (3H, triplet, J = 7.25 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 211.7 (C of carbonyl group at position 15) 165.8 (C of carbonyl group of anisoyl group) 164.0, 131.7 (2c), 121.6, 11
3.8 (2C) (C of anisoyl group) 86.1, 84.0, 83.6, 78.3, 77.4,
77.0, 71.9 (16, 6, 1, 14, 18, 1
3,3 position C) 49.1 (N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) EI-mass spectrometry m / z 615 (M ⁺ ) 7) [Α] _D ²⁵ = -58.9 ゜ (c = 0.55, ethanol)

(247) Physical Properties and Analytical Data of Pyrogesaconitine 1) Properties and Solubility A colorless, non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3484, 1711 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.92 (2H, doublet, J = 8.91) (H of anisoyl group) 6.94 (2H, doublet, J = 8.91) (same as above) 5.14 (1H, doublet) Line, J = 3.96 Hz) (β-H at position 14) 3.86 (3H, singlet) (H of methoxy group of anisoyl group) 3.63 (3H, singlet) (β-methoxy at position 16) H) 3.30 (3H, singlet) (H of methoxy group at positions 1, 6 and 18) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) Top) 1.03 (3H, triplet, J = 7.25 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm) . 211.9 (C of carbonyl group at position 15) 166.8 (C of carbonyl of anisoyl group) 163.6, 131.9 (2C), 121.9, 11
3.7 (2C) (C of anisoyl group) 89.2,84.1,83.5,79.2,77.4
76.6, 71.5 (16, 6, 1, 14, 18, 1
C at position 3,3) 49.1 (C of methylene of N-ethyl group) 13.3 (C of methyl of N-ethyl group) 6) EI-mass spectrum analysis m / z 615 (M ⁺ ) 7) [Α] _D ²⁵ = + 20.5 ゜ (c = 0.43, ethanol)

(248) Physical Properties and Analytical Data of 14-O-Benzoylaconine 1) Properties and Solubility A colorless, non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99-8.07 (5H, m) (H of benzoyl group) 4.98 (1H, doublet, J = 5.1 Hz) (H at 14th position) 3.72 (3H, singlet) ( 3.46 (3H, singlet) (same as above) 3.36 (3H, singlet) (same as above) 3.28 (3H, singlet) (H of the methoxy group at positions 1, 6, 16, and 18) 1.41 (3H, triplet, J = 7.00 Hz) (H of methyl group of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. ppm). 166.3 (C of carbonyl group derived from benzoyl group) 130.0, 129.9 (2C), 128.3 (2
C), 132.8 (C of benzoyl group) 91.0, 82.8, 81.8, 81.5, 79.9,
78.3, 77.4, 74.771.0 (16, 1,
6,15,14,8,18,13,3rd position C) 61.0,59.0,57.8,55.3 (16,6,
18,1 (C of the methoxy group bonded to 1) 49.2 (C of the methylene group of the N-ethyl group) 12.4 (C of the methyl group of the N-ethyl group) 6) EI-mass spectrum analysis m / z 603 (M ⁺ )

(249) Physical Properties and Analytical Data of 14-O-Benzoyl Mesaconin 1) Properties and Solubility A colorless non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr): The maximum absorption is shown at 3500 and 1717 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.01-8.04 (2H, m) (H of benzoyl group) 7.40-7.59 (3H, m) (same as above) 4.96 (1H, multiplet) (H at third position) 5 .01 (1H, double line, J = 5.0 Hz) (14th H) 4.55 (1H, double line, J = 5.0 Hz) (15th H) 4.09 (1H, 2H) Doublet, J = 6.9 Hz) (H at position 6) 3.69 (3H, singlet) (H at 1,6,16 and 18th methoxy groups) 3.31 (3H, singlet) Top) 3.30 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 2.37 (3H, singlet) (H of methyl of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.8, 130.1, 129.6, 128.3 (C of benzoyl group) 93.2, 82.1, 82.5, 78 .2,79.5,
79.0, 77.3, 74.6, 70.4 (16, 6,
1,8,14,15,18,13,3rd position C) 61.5,59.0,58.6,55.5 (16,1
8,6,1 bonded methoxy group C) 42.6 (N-methyl group methyl C) 6) EI-mass spectrum analysis m / z 603 (M ⁺ )

(250) Physical Properties and Analytical Data of 14-O-Benzoylhypaconin 1) Properties and Solubility A colorless non-crystalline powder of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3440 and 1725 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.02-8.05 (2H, multiplet) (H of benzoyl group) 7.42-7.60 (3H, multiplet) (same as above) 5.04 (1H, doublet, J = 5. 0 Hz) (14th place H) 4.54 (1H, double line, J = 5.3 Hz) (15th place) 4.04 (1H, double line, J = 6.9 Hz) (6th place H) 3.69 (3H, singlet) (methoxy group H at positions 1, 6, 16 and 18) 3.33 (3H, singlet) (same as above) 3.30 (3H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 2.37 (3H, singlet) (H of N-methyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown ( δ, ppm). 166.2 (C of carbonyl group derived from benzoyl group at position 14) 132.9, 130.3, 129.7, 128.3 (C of benzoyl group) 93.4, 82.6, 83.0, 78 6,79.5,
79.4, 79.0, 74.6 (16, 6, 1, 8,
C at positions 14, 15, 18, and 13) 61.4, 59.4, 58.9, 55.9 (16, 1
C, a methoxy group bonded to the 8,6,1-position) 57.0 (methylene group C, an amyl group bonded to the 8-position) 42.5 (C, an N-methyl group) 6) EI-mass spectrum analysis m / z 573 (M ⁺ )

(251) Physical Properties and Analytical Data of 14-O-Anisoyl Aconine 1) Solubility Colorless, melting point: 183-184 ° C as crystals, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine , Soluble in dimethylsulfoxide and insoluble in hexane and water. 2) [α] _D ¹⁹ = + 10.8 ゜ (CHCl ₃ , c = 1
00) 3) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3450, 2950, and 1740 cm ^-1 . 4) UV absorption spectrum (ethanol) analysis

Embedded image 5) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.96 (2H, double line, J = 8.9 Hz) (H of anisoyl group) 6.89 (2H, double line, J = 8.9 Hz) (same as above) 4.97 (1H, double line) Line, J = 5.27 Hz) (β-H at position 14) 4.51 (1H, multiple line) (H at position 15) 4.09 (1H, doublet, J = 6.26 Hz) (position 6 H) 3.85 (3H, singlet) (H of methoxy group of anisoyl group) 3.70 (3H, singlet) (H of methoxy group at 1,6,16 and 18 positions) 3.31 (3H 3.29 (3H, singlet) (same as above) 3.24 (3H, singlet) (same as above) 1.09 (3H, triplet, J = 6.92 Hz) (same as above) H) of methyl of N-ethyl group 6) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of carbonyl of anisoyl group) 165.3, 131.8, 122.1, 113.6
(C of anisoyl group) 78.6, 90.7, 83.5, 82.4, 79.5,
81.9, 74.8, 77.3, 71.9 (8, 16,
6,1,14,15,13,18,3 position C) 49.1 (N-ethyl group methylene C) 12.5 (N-ethyl group methyl C) 7) EI-mass spectrum analysis m / z 633 (M ⁺ )

(252) Physical properties and analytical data of neoline 1) Solubility A colorless needle-like crystal having a melting point of 158 to 163 ° C, which can be used in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine and dimethyl sulfoxide. It is soluble, hardly soluble in hexane, and insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.21 (1H, triplet, J = 4.8 Hz) (14th H) 4.16 (1H, doublet, J = 6.6 Hz) 3.66 (1H, triplet, J = 3. 0 Hz) 3.63 (1H, doublet, J = 8.1 Hz) 3.33 (3H, singlet) (H of methoxy group) 3.33 (3H, singlet) (same as above) 3.32 ( 3H, singlet) (same as above) 1.13 (3H, triplet, J = 7.2 Hz) (H of methyl of N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (Δ, ppm). 83.0, 81.6, 80.1, 75.9, 74.1,
72.1, 63.8 (6, 16, 18, 14, 8, 1,
C at position 17) 59.1,57.8,56.2 (C at methoxy group) 56.9 (C at position 19) 48.2 (C at methylene at N-ethyl group) 12.9 (N- C) 5) EI-mass spectrum analysis m / z 437 (M ^<+> )

(253) Physical property values and analytical data of 14-O-acetylneoline 1) Solubility A colorless powder which is soluble in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine and dimethyl sulfoxide. , Hardly soluble in hexane and insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3580, 1720 and 1270 cm ⁻¹ . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.86 (1H, triplet, J = 4.6 Hz) (14th H) 4.11 (1H, doublet, J = 6.4 Hz) 3.63 (1H, doublet, J = 8) .1 Hz) 3.34 (3H, singlet) (H of methoxy group) 3.33 (3H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 3.26 (1H, singlet) Double line, J = 8.1 Hz) 2.06 (3H, singlet) (H of acetyl group methyl) 1.14 (3H, triplet, J = 7.2 Hz) (N-ethyl group methyl) H) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.4 (C of carbonyl of acetyl group) 83.3, 81.9, 80.2, 77.2, 74.7,
72.1, 63.4 (6, 16, 18, 14, 8, 1,
C at position 17) 59.2, 58.0, 56.1 (C of methoxy group) 57.0 (C at position 19) 48.4 (C of methylene of N-ethyl group) 21.3 (acetyl group 13.0 (methyl C of N-ethyl group) 5) EI-mass spectrometry m / z 479 (M ⁺ )

(254) Physical property values and analytical data of 14-O-benzoylneoline 1) Solubility A colorless powder which is soluble in ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine and dimethyl sulfoxide. , Hardly soluble in hexane and insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis 3580, 1720, 1605, 1505, 1270c
m ^-1 shows the absorption maximum. 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.80-8.03 (3H, multiplet) (H of benzoyl group) 7.32-7.59 (2H, multiplet) (same as above) 5.18 (1H, triplet, J = 5.0 Hz) ) (H at position 14) 4.14 (1H, doublet, J = 7.0 Hz) 3.35 (6H, singlet) (H of methoxy group) 3.26 (3H, singlet) (same as above) ) 3.63 (1H, doublet, J = 8.0 Hz) 3.26 (1H, doublet, J = 8.0 Hz) 1.14 (3H, triplet) (H of methyl in N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of carbonyl of benzoyl group) 132.9, 130.1, 129.5, 128.4
(C of benzoyl group) 83.3, 81, 9, 80.0, 76.9, 74.8,
72.0, 63.3 (6, 16, 18, 14, 8, 1,
C at position 17) 59.1, 57.9, 56.0 (C at methoxy group) 56.9 (C at position 19) 48.2 (C at methylene at N-ethyl group) 13.0 (N- 6) EI-mass spectrometry m / z 541 (M ⁺ )

(255) Physical property values and analysis data of 14-Op-chlorobenzoylmesaconin 1) Solubility Colorless, odorless powder as ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, doublet, J = 8.8 Hz) (H of p-chlorobenzoyl group) 7.43 (2H, doublet, J = 8.8 Hz) (same as above) 4.95 (1H) , Doublet, J = 5.4 Hz) (β-H at position 14) 3.70 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, singlet) Line) (same as above) 3.29 (3H, singlet) (same as above) 3.24 (3H, singlet) (same as above) 2.38 (3H, singlet) (H of N-methyl group) 5 ) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis. The following signals are shown (δ, ppm). 165.4 (C of carbonyl of p-chlorobenzoyl group) 140.0, 131.8, 129.1, 128.4
(C of p-chlorobenzoyl group) 90.2, 82.9, 81.9, 81.7, 79.4
78.3, 77.0, 74.4, 71.8 (16, 1,
15,14,8,18,13th position C) 60.5,59.3,58.2,55.9 (16,1
C) 42.7 (C of N-methyl group) 6) EI-mass spectrum analysis m / z 623, 625 (M ⁺ )

(256) Physical property values and analytical data of 14-Op-chlorobenzoylaconine 1) Solubility Colorless, odorless needle-like crystals having a melting point of 221 to 222 ° C, ether, chloroform, benzene, ethanol, methanol, It is soluble in acetone, ethyl acetate, pyridine, dimethyl sulfoxide, and insoluble in hexane and water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.99 (2H, doublet, J = 8.9 Hz) (H of p-chlorobenzoyl group) 7.40 (2H, doublet, J = 8.9 Hz) (same as above) 4.97 (1H) , Doublet, J = 5.4 Hz) (β-H at position 14) 3.71 (3H, singlet) (H 2 of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) Line) (same as above) 3.30 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 1.10 (3H, triplet, J = 7.0) (N− Ethyl methyl H) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis shows the following signals (δ, ppm): 165.3 (C of carbonyl of p-chlorobenzoyl group) 139.6, 131.1, 128, 8, 128.2
(C of p-chlorobenzoyl group) 90.7, 83.0, 82.4, 81.8, 79.9,
78.5, 77.1, 74.6, 71.6 (16,
6,1,15,14,8,18,13,3rd position C) 60.8,59.1,58.0,55.7 (16,1
8,6,1-position methoxy group H) 48.9 (N-ethyl methylene C) 13.0 (N-ethyl methyl C) 6) EI-mass spectrometry m / z 637,639 ( M ⁺ )

(257) Physical property values and analytical data of 14-p-fluorobenzoyl aconine 1) Properties and solubility A colorless, odorless powder was used as ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1725 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (2H, doublet, J = 8.91) (H of p-fluorobenzoyl group) 7.42 (2H, doublet, J = 8.91) (same as above) 5.02 (1H) , Doublet, J = 5.2 Hz) (β-H at position 14) 3.76 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.33 (3H, singlet) (Same as above) 3.31 (3H, singlet) (same as above) 3.23 (3H, singlet) (same as above) 1.15 (3H, triplet, J = 7.2 Hz) (N− H) of methyl of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 164.8 (C of carbonyl of p-fluorobenzoyl group) 160.1, 131.0, 126.5, 124.8
(C of p-fluorobenzoyl group) 90.5, 82.8, 82.4, 81.6, 79.5
78.6, 76.9, 74.4, 71.4 (16, 6,
1,15,14,8,18,13,3-position C) 49.0 (N-ethyl group methylene C) 13.1 (N-ethyl group methyl C) 6) EI-mass spectrum analysis m / z 621 (M ⁺ )

(258) Physical property values and analytical data of 14-Op-bromobenzoylaconine 1) Properties and solubility A colorless, non-crystalline powder, which was formed of ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, and ethyl acetate.
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1723 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.04 (2H, doublet, J = 8.9) (H of p-bromobenzoyl group) 7.42 (2H, doublet, J = 8.9) (same as above) 5.04 (1H) , Doublet, J = 5.4 Hz) (β-H at position 14) 3.72 (3H, singlet) (H of methoxy groups at positions 1, 6, 16 and 18) 3.30 (3H, singlet) Line) (same as above) 3.29 (3H, singlet) (same as above) 3.27 (3H, singlet) (same as above) 1.13 (3H, triplet, J = 7.2 Hz) (N− H) of methyl of ethyl group 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.0 (C of carbonyl group of p-bromobenzoyl group) 140.1, 131.4, 129.2, 128.6
(C of p-bromobenzoyl group) 90.5, 83.2, 82.5, 81.7, 80.1,
78.4, 77.0, 74.7, 71.6 (16,
6,1,15,14,8,18,13,3rd position C) 59.6,59.0,57.8,55.6 (16,1
8,6,1-position methoxy group C) 49.1 (N-ethyl group methylene C) 13.3 (N-ethyl group methyl C) 6) EI-mass spectrum analysis m / z 681, 683 (M ⁺ )

(259) Physical property values and analytical data of 3,14-di-Op-chlorobenzoyl aconine 1) Properties and solubility A colorless non-crystalline powder, which is ether, chloroform, benzene, ethanol, methanol, acetone. ,Ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3500 and 1715 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00 (4H, doublet, J = 7.0) (H of p-chlorobenzoyl group) 7.43 (4H, doublet, J = 7.0) (same as above) 5.18 (1H) , Double doublet, J = 12.1, 5.4 Hz) (β-H at position 13) 4.96 (1H, doublet, J = 5.4 Hz) (β-H at position 14) 3.70 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.32 (3H, singlet) (same as above) 3.30 (3H, singlet) (same as above) 3.24 (3H, singlet) (ibid.) 1.12 (3H, triplet, J = 7.0 Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) Analysis shows the following signals (δ, ppm). 165.4 (C of carbonyl group of two p-chlorobenzoyl groups) 139.7, 131.1, 128.8, 128.3 (2
C) of 9 p-chlorobenzoyl groups 90.6, 83.0, 82.5, 81.7, 80.0,
78.4, 77.0, 74.5, 71.8 (16,
6,1,15,14,8,18,13,3rd position C) 60.8,59.0,58.1,55.6 (16,1
8,6,1-position methoxy group C) 48.8 (N-ethyl group, methylene C) 13.1 (N-ethyl group, methyl C) 6) EI mass spectrometry m / z 775 , 777,779 (M ⁺ )

(260) N-desethyl-14-Op
-Physical properties and analytical data of chlorobenzoyl aconine 1) Solubility Colorless, odorless powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.02 (2H, doublet, J = 8.9 Hz) (H of p-chlorobenzoyl group) 7.47 (2H, doublet, J = 8.9 Hz) (same as above) 5.01 (1H) , Doublet, J = 5.2 Hz) (β-H at position 14) 3.71 (3H, singlet) (H of methoxy groups at positions 1, 6, 16 and 18) 3.31 (3H, singlet) Line) (same as above) 3.30 (3H, singlet) (same as above) 3.25 (3H, singlet) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown. (Δ, ppm). 165.2 (C of carbonyl of p-chlorobenzoyl group) 139.8, 131.6, 129.0, 128.2
(C of p-chlorobenzoyl group) 90.9, 83.1, 82.5, 81.6, 79.8,
78.6, 77.0, 74.4, 71.5 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59,0,57.8,55.6 (16,1
C) of the methoxy group at the 8,6,1 position 6) EI-mass spectrum analysis m / z 609,611 (M ⁺ )

(261) Physical properties and analytical data of 1,14-di-O-acetylneoline 1) Solubility Colorless powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl sulfoxide Soluble in water, hardly soluble in hexane, and insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3580 and 1720 cm ⁻¹ . 3)
¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.86 (1H, triplet, J = 4.6 Hz) (14th H) 4.30 (1H, triplet, J = 3.1 Hz) (1st H) 4.11 (1H, double Line, J = 6.4 Hz) 3.63 (1H, double line, J = 8.1 Hz) 3.34 (3H, singlet) (methoxy group H) 3.33 (3H, singlet) (same as above) Top) 3.27 (3H, singlet) (same as above) 3.26 (1H, doublet, J = 8.1 Hz) 2.06 (3H, singlet) (H of acetyl group methyl) 02 (3H, singlet) (same as above) 1.14 (3H, triplet, J = 7.2 Hz)) (H of methyl in N-ethyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.4 (C of carbonyl of acetyl group) 170.1 (Id.) 83.2, 82.0, 80.2, 77.3, 74.7,
74.0, 63.5 (6, 16, 18, 14, 8, 1, 1)
C at position 17) 59.1, 58.2, 56.1 (C at methoxy group) 57.0 (C at position 19) 48.3 (C at methylene at N-ethyl group) 21.3, 21. 5 (methyl C of acetyl group) 13.0 (methyl C of N-ethyl group) 5) EI-mass spectrum analysis m / z 521 (M ⁺ )

(262) Physical property values and analytical data of 1,14-di-O-benzoylneoline 1) Solubility Colorless powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl sulfoxide Soluble in water, hardly soluble in hexane, and insoluble in water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis 3580, 1720, 1710, 1605, 1585,
The absorption maximum is shown at 1275 cm ⁻¹ . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.78 to 8.16 (6H, multiplet) (H of benzoyl group) 7.37 to 7.64 (4H, multiplet) (ibid.) 4.98-5.27 (2H, multiplet) ( H at position 1,14) 4.21 (1H, doublet, J = 7.0 Hz) (H at position 6) 3.36 (3H, singlet) (H at methoxy group) 3.33 (3H, 3.10 (3H, singlet) (same as above) 1.21 (3H, triplet, J = 7.0 Hz) (N-ethyl methyl H) 5) ¹³ C nuclear magnetic field The signals following the resonance spectrum (CDCl ₃ ) are shown (δ, ppm). 166.2 (C of carbonyl of benzoyl group) 166.0 (same as above) 133.1, 133.0, 130.2, 130.1, 1
29.6, 129.4, 128.5, 128.4 (C of benzoyl group) 83.4, 81.8, 80.2, 76.9, 74, 9,
74.0, 63.3 (6, 16, 18, 14, 8, 1,
C at position 17) 59.2, 57.8, 56.1 (C of methoxy group) 56.9 (C at position 19) 48.3 (C of methylene of N-ethyl group) 13.0 (N- C) 6) EI-mass spectrum analysis m / z 645 (M ⁺ )

(263) Physical properties and analytical data of 14-O- (3-chloropropionyl) -aconine 1) Solubility A colorless powder, ether, chloroform, benzene, ethanol, methanol, acetone, ethyl acetate, pyridine, dimethyl Soluble in sulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 1715 cm ⁻¹ . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 4.83 (1H, doublet, J = 5.0 Hz) (H at position 14) 3.70 (3H, singlet) (methoxy H at 1,6,16 and 18) 3.31 (3H , Singlet) (same as above) 3.30 (3H, singlet) (same as above) 3.25 (3H, singlet) (same as above) 4.10 (2H, triplet, J = 7.2 Hz) (same as above) H of methylene of 3-chloropropionyl) 3.47 (2H, triplet, J = 7.2 Hz) (same as above) 1.10 (3H triplet, J = 7.0 Hz) (methyl of N-ethyl) H) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 170.2 (C of carbonyl of 3-chloropropionyl) 90.8, 83.4, 82.3, 79.8, 79.5
78.6, 77.3, 74.8, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,58.0,55.6 (16,1
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.3 (N-ethyl group methyl C) 5) EI-mass spectrum analysis m / z 589, 591 (M ⁺ )

(264) Physical property values and analytical data of 14-O- (4-hydroxybutyl) -aconine 1) Solubility A colorless powder as ether, chloroform, benzene, ethanol, methanol acetone, ethyl acetate, pyridine,
Soluble in dimethylsulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3260 cm ⁻¹ . 3) ¹ H NMR spectrum (CDCl ₃ ): The following signals are shown (δ, ppm). 3.64 (3H, singlet) (H of methoxy at positions 1, 6, 16 and 18) 3.33 (3H, singlet) (same as above) 3.31 (3H, singlet) (same as above) 3 .28 (3H, singlet) (Id.) 1.10 (3H, triplet, J = 7.0 Hz) (H of N-ethyl methyl) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 90.7, 83.5, 82.1, 82.0, 79.5
78.8, 77.3, 74.5, 72.0 (16,
6,1,15,14,8,18,13,3-position C) 62.7,61.3 (4-hydroxybutyl methylene C) 60.9,59.1,57.9,55 .5 (16, 1
8,6,1-position methoxy group C) 49.1 (N-ethyl group methylene C) 13.2 (N-ethyl group methyl C) 5) EI-mass spectrometry m / z 571 ( M ⁺ )

(265) Physical property values and analytical data of 14-O- (4-methylcyclohexyl) -aconine 1) Solubility Colorless powdered ether, chloroform, benzene, ethanol, methanol acetone, ethyl acetate, pyridine,
Soluble in dimethylsulfoxide, insoluble in hexane and water. 2) Infrared absorption spectrum (CHCl ₃ ) analysis The absorption maximum is shown at 3300 cm ⁻¹ . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 3.70 (3H, singlet) (methoxy H at positions 1, 6, 16 and 18) 3.32 (3H, singlet) (same as above) 3.30 (3H, singlet) (same as above) 3 1.26 (3H, triplet, J = 7.0 Hz) (N-ethyl methyl H) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm). 90.6, 83.2, 82.1, 81.9, 79.5
78.9, 77.4, 74.5, 71.9 (16,
6,1,15,14,8,18,13,3-position C) 70.4,66.4 (1 of 4-methylcyclohexyl group)
C) 60.9, 59.1, 57.9, 55.6 (16, 1
8,6,1-position methoxy group C) 49.0 (N-ethyl group methylene C) 13.0 (N-ethyl group methyl C) 23.1 (4-methylcyclohexyl group methyl) C) 18.8 (ibid.) 5) EI-mass spectrum analysis m / z 595 (M ⁺ )

(266) Physical Properties and Analytical Data of N-Desethyl-N- (p-anisoyl) -14-O-benzoylaconine 1) Solubility Colorless, odorless powder, ether, chloroform, benzene, ethanol, methanol , Acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) UV absorption spectrum (ethanol) analysis

Embedded image 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 7.90 (2H, doublet, J = 8.9 Hz) (H of p-anisoyl group) 6.88 (2H, doublet, J = 8.9 Hz) (same as above) 7.82-7. 10 (5H, multiplet) (H of benzoyl group) 3.89 (3H, singlet) (H of 1,6,1618 and methoxy group of anisoyl group) 3.72 (3H, singlet) ( 3.30 (3H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) (same as above) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.3 (C of carbonyl of p-anisoyl group) 166.0 (C of carbonyl of benzoyl group) 164.0, 131.8, 126.1, 113.8 (p
-C of the anisoyl group 133.1, 129.7, 129.6, 128.4
(C of benzoyl group) 90.9, 83.0, 81.9, 81.8, 79.6
78.5, 77.2, 74.6, 72.0 (16,
6,1,15,14,8,18,13,3-position C) 60.9,59.1,57.9,55.4,55.1
(C at the methoxy group of the 16,18,6,1-position and anisoyl group) 6) EI-mass spectrum analysis m / z 733 (M ⁺ )

(267) Physical Properties and Analytical Data of N-Desethyl-N- (3-chloropropionyl) -14-O-benzoylaconine 1) Solubility Colorless, odorless powder, ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 and 1655 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.04-7.37 (5H, multiplet) (H of benzoyl group) 5.00 (1H, doublet, J = 5.0 Hz) (H at 14th position) 3.72 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.25 (3H, singlet) (Id.) 4.10 (2H, triplet, J = 7.0 Hz) (H of methylene of 3-chloropropionyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis , Ppm). 172.0 (C of carbonyl of 3-chloropropionyl group) 166.0 (C of carbonyl of benzoyl group) 133.1, 129.8, 129.7, 128.3 (C of benzoyl group) 90.7, 83.1, 82.0, 81.8, 79.5,
78.6, 77.3, 74.7, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,58.0,55.4 (16,1
C) of methoxy group at 8, 6 and 1 position 6) EI-mass spectrum analysis m / z 665,667 (M ⁺ )

(268) Physical Properties and Analytical Data of N-Desethyl-N-crotyl-14-O-benzoylaconine 1) Solubility Colorless, odorless powder as ether, chloroform, benzene, ethanol, methanol, acetone, acetic acid ethyl,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1720 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.00-7.20 (5H, multiplet) (H of benzoyl group) 5.01 (1H, doublet, J = 5.0 Hz) (H at 14th position) 3.72 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) (same as above) 3.28 (3H, singlet) (same as above) 3.25 (3H, singlet) (Same as above) 5.70 (2J, multiplet) (H binding to carbon of double bond of crotyl group) 1.68 (3H, doublet, J = 6.2 Hz) (H of methyl of crotyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 165.9 (C of carbonyl of benzoyl group) 133.2, 129.8, 129.6, 128.4 (C of benzoyl group) 131.2, 122.6 (C of double bond of crotyl group) 90 .7, 83.3, 82.1, 81.9, 79.5
78.6, 77.3, 74.7, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,58.0,55.4 (16,1
C) of methoxy group at 8, 6 and 1 position 13.0 (C of crotyl group methyl) 6) EI-mass spectrometry m / z 629 (M ⁺ )

(269) Physical Properties and Analytical Data of N-Desethyl-N- (4-methylcyclohexyl) -14-O-benzoylaconine 1) Solubility A colorless, odorless powder with ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.04-7.35 (5H, multiplet) (H of benzoyl group) 5.01 (1H, doublet, J = 5.0 Hz) (H at 14th position) 3.70 (3H, singlet) (H of the methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) (same as above) 3.28 (6H, singlet) (same as above) 4) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) analysis shows the following signals (δ, ppm): 166.0 (C of benzoyl group) 133.1, 129.7, 129.6, 128.3 (C of benzoyl group) 90.6, 83.4, 82.3, 82.0, 79. 4,
78.6, 77.3, 74.7, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.0,58.0,55.5 (16,1
18. M, C of methoxy group at 8, 6 and 1 position 58.6 (C of 1 position of 4-methylcyclohexyl group) 53.2 (Id.) 23.0 (C of methyl of 4-methylcyclohexyl group) 3 (same as above) 5) EI-mass spectrum analysis m / z 671 (M ⁺ )

(270) Physical property values and analytical data of N-desethyl-N- (4-hydroxybutyl) -14-O-benzoylaconine 1) Solubility A colorless, odorless powder which was prepared by using ether, chloroform, benzene, ethanol, Methanol, acetone, ethyl acetate,
Soluble in pyridine and dimethyl sulfoxide, hexane,
Insoluble in water. 2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1710 cm ^-1 . 3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 8.02-7.10 (5H, multiplet) (H of benzoyl group) 5.02 (1H, doublet, J = 4.9 Hz) (H at 14th position) 3.71 (3H, singlet) (H of methoxy group at positions 1, 6, 16 and 18) 3.31 (3H, singlet) (same as above) 3.29 (3H, singlet) (same as above) 3.26 (3H, singlet) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm). 166.0 (C of benzoyl group) 133.2, 129.8, 129.5, 128.3 (C of benzoyl group) 90.8, 83.4, 82.3, 82.0, 79. 4,
78.6, 77.3, 74.7, 72.0 (16,
6,1,15,14,8,18,13,3rd position C) 60.9,59.1,57.9,55.6 (16,1
C, 6 and 6 of the methoxy group at position 6, 6 and 6 (C at position 4 of the 4-hydroxybutyl group) 5) EI-mass spectrometry m / z 64
7 (M ⁺ )

Experimental examples on the pharmacological action and acute toxicity of the compound represented by the above formula (I) are shown below. [Experimental Example 1] (Blood flow increasing effect) In the experiment, a Std: ddY male mouse (20 to 25 g) was used.
Was used as 5 animals per group. Animals are at room temperature 24-25 ° C,
The animals were housed under free access to water, water, and 12-hour light / dark conditions. The test drug was dissolved in dimethyl sulfoxide before use. The mouse was used on the day before the test in which the back was depilated with a depilatory cream. After the mouse was anesthetized with urethane, a laser Doppler blood flow meter (ALF)
21, manufactured by Advance Co., Ltd.) and the blood flow before drug administration was measured. Next, 0.05 ml of the drug dissolved in dimethyl sulfoxide was administered into the tail vein of the mouse, and 10 minutes later, the blood flow (ml / min / 1
00g). The results were shown by the cumulative blood flow increased from 10 minutes to 25 minutes after the drug administration, compared to the blood flow before the drug administration. The negative control group received only the dimethyl sulfoxide solution. The significant difference test of the drug administration group by the comparison between groups was performed by Student's t-test. Table 1 shows the results. As shown in Table 1, all the compounds according to the present invention showed P <
A significant blood flow promoting effect of 0.05 was observed.

[Experimental Example 2] (Acute toxicity) In the experiment, std: ddY male mouse (20 to 25 g) was used.
It was used. Test drug was calculated _{LD 50} value on the basis of the Litchfield-Wilcoxon method from a lethal number of 72 hours after subcutaneous administration. Table 2 shows the results. As shown in Table 2, the compounds according to the present invention were found to be less toxic than mesaconitine, aconitine, hypoconitine and jesaconitine.

As described above, it has been found that the compound represented by the formula (I) has lower toxicity than mesaconitine, aconitine, hypoconitine and jesaconitine, and has a strong blood circulation promoting action.

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

The clinical dose of the blood circulation-promoting agent according to the present invention is 1 to 1000 for the compound of formula (I).
An amount of mg / day is preferred. The preparation according to the present invention is prepared in a desired dosage form by a conventional method using a commonly used preparation carrier or excipient, and is used. In addition, the compound of the present invention can be used as any required salt in order to achieve a pharmaceutical effect or to facilitate formulation.

Tablets, powders, granules, capsules and the like for oral administration include conventional excipients such as calcium carbonate, magnesium carbonate, calcium phosphate, corn starch, potato starch, sugar, lactose, talc, and the like.
It may contain magnesium stearate, gum arabic and the like. Tablets may be coated by known methods. Oral liquid preparations include aqueous or oily suspensions, solutions,
Syrups, elixirs and others may be used.

In the preparation for injection, the compound represented by the above formula (I) may be used in the form of a salt, and the dissolution form at the time of use is preferable. It may also contain various formulating agents such as suspending agents, stabilizers or dispersants, and sterile distilled water, essential oils such as peanut oil, corn oil or non-aqueous solvents, polyethylene glycol, polypropylene glycol and the like. It may be contained.

Formulations for rectal administration are provided in the form of suppository compositions and are well known in the art for pharmaceutical carriers such as polyethylene glycol, lanolin,
Coconut oil and the like may be contained.

Formulations for topical application may be provided in the form of ointments, plasters, or cataplasms and may be formulated with carriers well known in the art, such as petrolatum, paraffin, Lanolin hydrous, plastibase, kaolin, bentonite, talc, aluminum silicate, propylene glycol, sorbitol, hydrophilic petrolatum, macrogol, wax, resin, purified lanolin, rubber, glycerin, gelatin, polyacrylic acid, polyacrylate, polyvinyl It may contain alcohol, polyvinylpyrrolidone, polyethylene oxide and the like.

[Formulation Example 1] Soft blue based on the above Formulation Example 1 was produced using 14-0-benzoylneoline as the compound of the formula (I) in the above Formulation Example, and blood flow was measured using an adult male as a subject. The test conditions are shown below.

[0590] The subject was placed in a supine position, a probe of a laser Doppler blood flow meter (ALF21, manufactured by Advance Co.) was attached to the back of the hand, and the blood flow before applying the ointment was measured for about 30 minutes. Next, around the probe attached, the above 14
An ointment containing -0-benzoylneoline as an active ingredient was applied, and the blood flow was measured for about 1 hour. The results were shown as the minimum blood flow and the maximum blood flow for 30 minutes before ointment application and 15 minutes to 1 hour after application. Table 3 shows the results
Shown in

[0591]

──────────────────────────────────────────────────続 き Continued on the front page (58) Fields investigated (Int. Cl. ⁷ , DB name) A61K 31/435 A61P 9/00 C07D 221/22 BIOSIS (STN) CA (STN) MEDLINE (STN) REGISTRY (STN )

Claims (1)

(57) [Claims] 1. A compound of the general formula (I) [Wherein, R ₁ and R ₂ are each (i) a hydrogen atom, or (ii) a saturated alkyl or an unsaturated alkyl having or not having a substituent, or (iii) a substituent. whether the with or without an aliphatic or aromatic acyl, or a (iv) substituted or without aralkyl, R ₃ is a hydrogen atom or a hydroxyl group or an aliphatic acyloxy or aromatic acyloxy R ₄ is a hydrogen atom or a hydroxyl group, R ₅ is a hydrogen atom or a hydroxyl group or a lower alkoxy or an aliphatic acyloxy, and R ₆ is a hydrogen atom or a hydroxyl group, or forms a carbonyl group together with the carbon atom at position 15. R ₇ is a hydrogen atom or methyl or aliphatic acyl or aromatic acyl. Wherein a) R ₁ is benzoyl or anisoyl;
₂ is ethyl, R ₃ and R ₆ are hydroxyl groups, R ₅
Is an acetyloxy group, and when R ₇ is methyl, R ₄ is a hydrogen atom. B) R ₁ is benzoyl, R ₂ and R ₇ are methyl, and R ₃ is a hydrogen atom or a hydroxyl group. And when R ₅ is an acetyloxy group and R ₆ is a hydroxyl group, R ₄ is a hydrogen atom.] The compound having an aconitine-type chemical structure represented by the formula: Medication to use for.