JP3037991B2 - New aconitine compounds and analgesic / anti-inflammatory agents - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a novel aconitine compound and an analgesic / anti-inflammatory agent.

More specifically, the present invention relates to the general formula [Wherein, R ₁ is (i) a saturated alkyl or unsaturated alkyl having or without a substituent, or (ii) an aliphatic or aromatic acyl having or not having a substituent. Or (iii) aralkyl with or without a substituent, and R ₂ is (i) saturated or unsaturated alkyl or hydrogen with or without a substituent, or (ii) R) is an aliphatic or aromatic acyl with or without a substituent, or (iii) an aralkyl with or without a substituent, and R _{3 and} R ₄ are each hydrogen or a hydroxyl group; ₅ is hydrogen and R ₆ is a hydroxyl group. Aconitine-based compound represented by the formula:
The present invention also relates to an analgesic / anti-inflammatory agent containing the aconitine compound represented by the above general formula (I) as an active ingredient.

(Background technology)

It has already been reported that aconitine alkaloid substances contained in tuberous roots of Aconitum plants have a strong analgesic action and anti-inflammatory action. However, aconitine alkaloids were considered to be highly toxic and therefore have a narrow safety margin.

[Disclosure of the Invention]

The present inventors have conducted various studies to obtain a novel aconitine alkaloid derivative which retains the analgesic / anti-inflammatory action of an aconitine alkaloid substance and has low toxicity, and as a result of the present invention, the compound represented by the general formula (I) ) Was successfully provided. In addition, the present inventors have found that the compound represented by the general formula (I) has strong analgesic / anti-inflammatory activity, and has lower toxicity than mesaconitine, aconitine, hypoconitine and jesaconitine.

The present invention has been made based on such findings. Accordingly, the present invention provides a novel compound represented by the general formula (I), and further provides an analgesic / anti-inflammatory agent containing the compound represented by the general formula (I) as an active ingredient. Is what you do.

The compound represented by the above formula (I) according to the present invention includes aconitine represented by the following formula (III), mesaconitine represented by the following formula (IV), hypoconitine represented by the following formula (V), Jesaconitine represented by the following formula (VI), 14-benzoylmesaconitine represented by the following formula (VII), 14-benzoylaconine represented by the following formula (VIII), represented by the following formula (IX) 14-benzoylhypaconin, 14-anisoyl aconin represented by the following formula (X),
Starting from aconitine-type alkaloids described in the literature such as pyroaconitines and epipyroaconitines represented by I), and performing a deoxygenation reaction at the 3-, 8- or 13-positions, or a nitrogen atom or 14-position thereof Can be produced by substituting various substituents for the substituents bonded to, and further performing a reaction of a combination thereof.

R ₁ , R ₂ , R ₃ , R ₄ and R _{5 in the} formulas (III) to (X) are as shown in the following table.

[R ₁ is CH ₃ or C ₂ H ₅ , R ₂ is OH or H, R ₃ is B
z or An] The above-described deoxygenation reaction can be performed by using an ion reaction, a radical reaction, a reduction reaction, or the like usually used in a chemical reaction, or a combination thereof. The ionic reaction can be performed, for example, by heating to reflux using a dehydrating agent such as sulfuric acid or thionyl chloride as a solvent, and in a suitable solvent, for example, tetrahydrofuran, in the presence of imidazole, sodium hydride, and the like. , Carbon disulfide and methyl iodide are stirred or heated to reflux under an appropriate temperature condition, and reacted to form a thioacylated product.Further, tributyltin hydride or the like is added in a solvent such as benzene, and the mixture is heated to room temperature or heated to reflux. And can be performed by stirring. In the reaction for replacing the substituent bonded to the nitrogen atom, first, a compound represented by each of the formulas III to XI is reacted with a suitable oxidizing agent such as potassium permanganate in an appropriate solvent such as acetone.
An N-dealkylated product is obtained. The reaction can be carried out by reacting the obtained N-dealkylated product with an alkylating agent, an acylating agent and the like, for example, an acid chloride, an alkyl halide or an aralkyl halide. In the reaction for replacing the substituent bonded to the 14-position, first, the substituent present in the form of an ester bond at the 14-position is de-esterified by a hydrolysis reaction, for example, alkali hydrolysis to form a hydroxyl group. In a suitable solvent, the acid chloride used when esterifying or etherifying the hydroxyl group, a halogen compound, etc., and the 14-position deesterified product obtained as described above,
For example, the reaction can be carried out in pyridine. The radical reaction can be carried out, for example, by irradiating a low-pressure mercury lamp at room temperature or under cooling using water and hexamethyltriamide phosphate as a solvent, and for example, active substitution of a hydroxyl group with oxalyl chloride or the like. A radical generating reagent in a solvent such as benzene,
For example, αα′-azoisobutyronitrile and the like, and a reducing agent,
For example, the reaction can be carried out by adding tributyltin hydride or the like and heating to reflux or stirring at room temperature. The reduction reaction can be performed, for example, by catalytic hydrogenation at room temperature or under heating in a solvent such as ethanol or acetic acid using platinum oxide, palladium carbon, Raney nickel or the like as a catalyst. In the above-described deoxygenation reaction, the hydroxyl group is converted to a ketone using an oxidizing agent, for example, sodium dichromate, etc., and is then converted to a thioketal or hydrazone by adding ethanedithiol or p-toluenesulfonylhydrazine.
Using ether or tetrahydrofuran as a solvent,
The reduction can be performed by using an organometallic reducing agent such as lithium aluminum hydride and its alkoxy derivative at room temperature, under heating or under cooling. Furthermore, the compound represented by the formula (I) can be obtained by variously combining the above reactions. Hereinafter, production examples of the compound represented by the formula (I) will be described. The physical property values and analytical data of the compounds obtained in each Example are listed after the description of the Examples. Also,
The pharmacological action, toxicity, etc. of the compound are listed in Tables 1 to 3 below.

Example 1 LiAl prepared from 72 mg of LiAlH ₄ and 0.23 ml of methanol
To a solution of (OCH ₃ ) ₃ H in tetrahydrofuran (THF), a THF solution containing 60 mg of pyrogesaconitine is added at -70 ° C, and the mixture is stirred at this temperature for about 1 hour and further 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,
45.6 mg of 8-deoxyaconin are obtained.

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 raised from -70 ° C to 70 ° 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 and purify 8-deoxy-14-O.
-37 mg of anisoyl aconin are obtained.

[Example 2] Instead of 3-deoxygesaconitine in Example 3,
The same operation as in Example 3 was carried out except that 100 mg of 3,13-dideoxyjesaconitine was used to obtain 62 mg of 3,13-dideoxypyrogesaconitine. Next, 3,8,13-trideoxyaconine was used in the same manner as in Example 1 except that 60 mg of 3,13-dideoxypyrrojesaconitine was used in place of the pyrogenesaconitine of Example 1. Obtain 48 mg. Next, instead of 8-deoxyaconine of Example 1, 3,
Example 13 used 45 mg of 8,13-trideoxyaconin, and
And the same operation as in 3,8,13-Trideoxy-14.
31 mg of -O-anisoylaconin are obtained.

Example 3 100 mg of 3-deoxygesaconitine was placed under reduced pressure (1-2 mm).
Hg) Heat at 180 ° C for 30 minutes. The reaction product is subjected to silica gel column chromatography (eluent: 5% methanol / chloroform) to separate and purify, thereby obtaining 60 mg of 3-deoxypyrogesaconitine.

The procedure of Example 1 was repeated, except that 60 mg of 3-deoxypyrrogesaconitine and 45 mg of 3,8-dideoxyaconine were used in place of the pyrogenesaconitine of Example 1.
32 mg of 8-dideoxy-14-O-anisoylaconine are obtained.

Example 4 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 the same operation as in Example 1 was carried out to give 8-deoxy-14-O-benzoylaconine 32 mg.
Get.

[Example 5] Instead of 3-deoxygesaconitine in Example 3, 100 mg of 3-deoxyaconitine was used, and the other operations were carried out exactly as in Example 3, to obtain 68 mg of 3-deoxypyroacoreconitine. Next, 3-deoxypyroaconitine was used in place of pyrogenesaconitine in Example 1, and the same operation as in Example 1 was carried out except for 60 mg.
49.5 mg of dideoxyaconitine are obtained. Next, Example 1
In place of 8-deoxyaconitine, 45 mg of 3,8-dideoxyaconitine was used, and 20 μl of benzoyl chloride was used in place of p-anisoyl chloride.
The same operation as in 3,8-dideoxy-14-O
-35 mg of benzoyl aconine are obtained.

[Example 6] Instead of 3-deoxygesaconitine in Example 3,
The same operation as in Example 3 was carried out except that 100 mg of 3,13-dideoxyaconitine was used to obtain 60.5 mg of 3,13-dideoxypyroaconitine. Next, 3,13-dideoxypyroaconitine 60 was used in place of pyrogenesaconitine in Example 1.
The same operation as in Example 1 was performed except for using mg, and
50.6 mg of 8,13-trideoxyaconine are obtained. Next, 45 mg of 3,8,13-trideoxyaconine was used in place of 8-deoxyaconine in Example 1, and 20 μl of benzoyl chloride was used in place of p-anisoyl chloride. The same operation as described above was carried out to obtain 3,3.2 mg of 3,8,13-trideoxy-14-O-benzoylaconine.

Example 7 The procedure of Example 1 was repeated except that 60 mg of pyromesaconitine was used in place of pyrogenesaconitine, and 47.2 mg of 8-deoxymesaconin was obtained. next,
The same operation as in Example 1 was carried out except that 45 mg of 8-deoxymethaconine was used in place of 8-deoxyaconine in Example 1 and 20 μl of benzoyl chloride was used in place of p-anisoyl chloride. -Deoxy-14-O-
34.8 mg of benzoylmesaconine are obtained.

Example 8 Instead of 3-deoxygesaconitine in Example 3,
The same operation as in Example 3 was carried out except that 100 mg of 3,13-dideoxymesaconitine was used to obtain 61.2 mg of 3,13-dideoxypyromesaconitine. Next, 3,8,13-trideoxymesaconin 48.7 mg 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. get mg. Next, instead of 8-deoxyaconine of Example 1, 3,
The same operation as in Example 1 was carried out except that 45 mg of 8,13-trideoxymesaconine was used, and 20 μl of benzoyl chloride was used instead of p-anisoyl chloride, and 3,8,13-
31.5 mg of trideoxy-14-O-benzoylmesaconin are obtained.

Example 9 The procedure of Example 1 was repeated, except that 60 mg of pyrohypaconitine was used in place of pyrogenesaconitine in Example 1, and 46.6 mg of 3,8-dideoxymesaconin was obtained. Next, instead of 8-deoxyaconine of Example 1, 3,8
Using exactly 45 mg of dideoxymesaconin and 20 μl of benzoyl chloride in place of p-anisoyl chloride, the same procedure as in Example 1 was followed, except that 3,8-dideoxy-14-O-benzoylmesaconin 36.3 was used. get mg.

Example 10 The procedure of Example 1 was repeated except that 60 mg of pyromesaconitine was used in place of pyroguesaconitine to obtain 47.2 mg of 8-deoxymesaconin. next,
The procedure of Example 1 was repeated, except that 45 mg of 8-deoxymesaconine was used instead of 8-deoxyaconine in Example 1, to obtain 32.5 mg of 8-deoxy-14-O-anisoylmesaconin. .

Example 11 The procedure of Example 1 was repeated, except that 60 mg of pyrohypaconitine was used in place of pyrojesaconitine in Example 1, and 46 mg of 3,8-dideoxymesaconin was obtained. Next, 25 mg of 3,8-dideoxymesaconin is dissolved in a mixture 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 raised from -70 ° C to 70 ° 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 10 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 is subjected to silica gel column chromatography (eluent: 5% methanol / ammonia-saturated chloroform) to separate and purify, thereby obtaining 17.5 mg of 3,8-dideoxy-14-O-anisoylmesaconin.

Example 12 Instead of 3-deoxygesaconitine in Example 3
The procedure of Example 3 was repeated except for using 100 mg of 3,13-dideoxymesaconitine to obtain 63.7 mg of 3,13-dideoxypyromesaconitine. Next, the same operation as in Example 1 was performed except that 3,13-dideoxypyrromesaconitine was used in place of pyrogenesaconitine in Example 1, and 3,8,13-trideoxymesaconin 31.5% was used. get mg.

Next, in place of 3,8-dideoxymesaconine in Example 11, 25 mg of 3,8,13-trideoxymesaconin was used, and the same operation as in Example 11 was carried out, except for 3,8,13. 16.7 mg of -trideoxy-14-O-anisoylmesaconin are obtained.

Example 13 LiAl prepared from 72 mg of LiAlH ₄ and 0.23 ml of methanol
To a solution of (OCH ₃ ) ₃ H in tetrahydrofuran (THF), a THF solution containing 16 mg of 16-epipyrogesaconitine was added at -70 ° C, and the mixture was stirred at this temperature for about 1 hour and further at room temperature for 1 hour. I do. After completion of the reaction, wet-THF was 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 added to 5 ml of pyridine.
And 1 ml of methylene chloride, and add 15 μl of p-anisoyl chloride 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 and purify, thereby obtaining 35 mg of 16-epi-8-deoxy-14-O-anisoylaconine.

Example 14 150 mg of 3-deoxygesaconitine was placed under reduced pressure (1-2 mm).
Hg) Heat at 180 ° C for 30 minutes. The reaction product is subjected to silica gel column chromatography (eluent: 5% methanol / chloroform) to separate and purify, thereby obtaining 63 mg of 16-epi-3-deoxypyrogesaconitine.

Instead of 16-epipyrogesaconitine in Example 13
Using the same procedure as in Example 13 except that 60 mg of 16-epi-3-deoxypyrrojesaconitine was used, 16-epi-3,8
35 mg of -dideoxy-14-O-anisoylaconine are obtained.

Example 15 Instead of 3-deoxygesaconitine in Example 14
The same operation as in Example 14 was carried out except that 150 mg of 3,13-dideoxyjesaconitine was used to obtain 61.7 mg of 16-epi-3,13-dideoxypyrogesaconitine. Next, using 16-epi-3,13-dideoxypyrogesaconitine instead of 16-epipyrogesaconitine in Example 13, 60 mg
Otherwise, the same operation as in Example 13 was performed, and 16-epi-3,
50.1 mg of 8,13-trideoxyaconin are obtained. Next, instead of 16-epi-8-deoxyaconine of Example 13,
Using 45 mg of 16-epi-3,8,13-trideoxyaconine,
Otherwise, the same operation as in Example 13 was performed, and 16-epi-3,
8,13-trideoxy 14-O-anisoylaconine 29.7mg
Get.

Example 16 16-epi-8-deoxy-14-O-benzoyl alcohol was used in the same manner as in Example 13 except that 20 μl of benzoyl chloride was used in place of p-anisoyl chloride of Example 13. 33.2 mg of nin are obtained.

Example 17 Instead of 3-deoxygesaconitine in Example 14, 150 mg of 3-deoxyaconitine was used.
By performing exactly the same operation as in 4, 46.5 mg of 16-epi-3-deoxypyroaconitine is obtained. Next, 16- of Example 13
The procedure of Example 13 was repeated except that 60 mg of 16-epi-3-deoxypyroaconitine was used instead of epipyrrogesaconitine, to obtain 47.2 mg of 16-epi-3,8-dideoxyaconitine. Next, 16-epi-8 of Example 13 was used.
16-epi-3,8-dideoxyaconitine was used in place of deoxyaconitine, and 45 μl of benzoyl chloride was used in place of p-anisoyl chloride. 36.2 mg of epi-3,8-dideoxy-14-O-benzoylaconine are obtained.

Example 18 Instead of 3-deoxygesaconitine in Example 14
Example 3 used 150 mg of 3,13-dideoxyaconitine, and
Perform exactly the same operation as in 4, to obtain 61.2 mg of 16-epi-3,13-dideoxypyroaconitine. Next, in Example 13
16-epi-3,13 instead of 16-epipyrogesaconitine
-Using dideoxypyroaconitine 60 mg, otherwise using Example 13
The same operation as described above was carried out to obtain 51.7 mg of 16-epi-3,8,13-trideoxyaconin. Next, 16- of Example 13
Instead of epi-8-deoxyaconin, 16-epi-3,
Using 45 mg of 8,13-trideoxyaconin,
The procedure of Example 13 was repeated, except that 20 μl of benzoyl chloride was used instead of anisoyl, to obtain 16-epi-3,8,13-trideoxy-14-O-benzoylaconine.
Obtain 30.5 mg.

Example 19 Instead of 16-Epipyrogesaconitine in Example 13
Using 16 mg of 16-epipyromesaconitine, otherwise using Example 13
The same operation as described above was carried out to obtain 46.1 mg of 16-epi-8-deoxymesaconin. Next, 16-epi-8 of Example 13 was used.
Using 45 mg of 16-epi-8-deoxymetaconin in place of deoxyaconine and 20 μl of benzoyl chloride in place of p-anisoyl chloride;
The same operation as described above was carried out to obtain 16-epi-8-deoxy-14.
34.8 mg of -O-benzoylmesaconin are obtained.

Example 20 Instead of 3-deoxygesaconitine in Example 14
The same operation as in Example 14 was carried out except for using 150 mg of 3,13-dideoxymesaconitine to obtain 63.5 mg of 16-epi-3,13-dideoxypyrromesaconitine. Next, Example 13
16-epipyrogesaconitine in place of 16-epi-
Using the same procedure as in Example 13 except that 60 mg of 3,13-dideoxypyrromesaconitine was used, 16-epi-3,8,13-
49.3 mg of trideoxymesaconin are obtained. Next, Example 13
Instead of the 16-epi-8-deoxyaconine of
Using 45 mg of epi-3,8,13-trideoxymesaconin, and further adding 20 μl of benzoyl chloride instead of p-anisoyl chloride
Using l, otherwise perform the same operation as in Example 13,
30.5 mg of 16-epi-3,8,13-trideoxy-14-O-benzoylmesaconin are obtained.

Example 21 Instead of 16-Epipyrogesaconitine in Example 13
Using 16 mg of 16-epipyrohypaconitine, otherwise using Example 13
The same operation as described above was carried out to obtain 45.8 mg of 16-epi-3,8-dideoxymesaconin. Next, 45 mg of 16-epi-3,8-dideoxymesaconin was used in place of 16-epi-8-deoxyaconine in Example 13, and 20 μl of benzoyl chloride was used in place of p-anisoyl chloride. Performs exactly the same operation as in Example 13 to obtain 35.7 mg of 16-epi-3,8-dideoxy-14-O-benzoylmesaconine.

Example 22 Instead of 16-epipyrogesaconitine in Example 13
Using 16 mg of 16-epipyromesaconitine, otherwise using Example 13
The same operation as described above was carried out to obtain 45.3 mg of 16-epi-8-deoxymesaconin. Next, 16-epi-8 of Example 13 was used.
16-epi-8-deoxy-14-O-anisoyl mesaconine 30.4 was used in the same manner as in Example 13 except that 45 mg of 16-epi-8-deoxymesaconine was used instead of deoxyaconine. get mg.

Example 23 16-Epipyrohypaconitine was used in place of 16-Epi-pyrrojesaconitine in Example 13, and the others were the same as in Example 13.
The same operation as described above was carried out to obtain 45 mg of 16-epi-3,8-dideoxymesaconin. Next, 25-mg of 16-epi-3,8-dideoxymesaconin was used in place of 3,8-dideoxymesaconin of Example 11, except that the same operation as in Example 11 was carried out. This gives 19.3 mg of, 8-dideoxy-14-O-anisoylmesaconin.

Example 24 Instead of 3-deoxygesaconitine in Example 14
Using exactly the same procedure as in Example 14 except that 150 mg of 3,13-dideoxymesaconitine was used, 62.1 mg of 16-epi-3,13-dideoxypyromesaconitine was obtained. Next, Example 13
16-epipyrogesaconitine in place of 16-epi-
Using the same procedure as in Example 13 except that 60 mg of 3,13-dideoxypyrromesaconitine was used, 16-epi-3,8,13-
31.2 mg of trideoxymesaconin are obtained. Next, Example 11
Instead of the 3,8-dideoxymesaconine of
Using exactly 3,8,13-trideoxymesaconin 25 mg, and otherwise performing the same operation as in Example 11, 16-epi-3,8,13-trideoxy-14-O-anisoylmesaconin 15.3 mg was used. obtain.

Example 25 The procedure of Example 1 was repeated, except that 70 mg of pyrogenesaconitine was used instead of 60 mg of pyrogenesaconitine, except that the procedure of Example 1 was repeated to obtain 53 mg of 8-deoxyaconin. 50 mg of 8-deoxyaconin was dissolved in 1 ml of pyridine, and 3,4,5-chloride was dissolved.
Add 30 mg of trideoxybenzoyl and 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 was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 8-deoxy-14 was purified.
28 mg of -O-trimethylgalloylaconin are obtained.

(Example 26) Instead of 3,4,5-trimethoxybenzoyl chloride of Example 25, using 25 mg of 3,4-dimethoxybenzoyl chloride,
Otherwise, operating exactly as in Example 25, 8-deoxy-14-
24 mg of O-veratroyl aconin are obtained.

Example 27 The procedure of Example 25 was repeated, except that 20 mg of p-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride of Example 25. Op
23 mg of chlorobenzoyl aconine are obtained.

Example 28 The procedure of Example 25 was repeated, except that 20 mg of m-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride of Example 25. O-m
-Obtain 20 mg of chlorobenzoyl aconine.

[Example 29] In place of 3,4,5-trimethoxybenzoyl chloride of Example 25, α-methyl- (4- (α-methylacetic acid) -phenyl) -acetyl chloride 50 µl was used. Operating exactly as in Example 25, 8-deoxy-14-O
22 mg of-[alpha] -methyl- (4-([alpha] -methylacetic acid) -phenyl) -acetolaconia are obtained.

Example 30 The same operation as in Example 1 is performed to obtain 8-deoxyaconine. 15 mg of 8-deoxyaconin in 1 ml of dioxane
Is dissolved, 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).
12 mg of 8-deoxy-14-O-methylaconine are obtained.

Example 31 The same operation as in Example 1 is performed to obtain 8-deoxyaconine. Dissolve 30 mg of 8-deoxyaconin in 2 ml of 1,2-dimethoxyethane, add 60 mg of sodium hydride,
Stir for 30 minutes at room temperature. Benzyl chloride is added to the reaction solution.
Add 50 μl and heat to reflux 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).
19 mg of -deoxy-14-O-benzylaconine are obtained.

Example 32 The same operation as in Example 1 is performed to obtain 8-deoxyaconine. 17 mg of 8-deoxyaconine was dissolved in 2 ml of 1,2-dimethoxyethane, and 50 mg of sodium hydride was added.
Stir for 30 minutes at room temperature. Add crotyl chloride to the reaction solution.
Add 0.5 ml and heat to reflux 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 is separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to obtain 12 mg of 8-deoxy-14-O-crotyl aconin.

Example 33 The procedure of Example 25 was repeated, except that 20 mg of o-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride of Example 25. 23 mg of O-chlorobenzoyl aconine are obtained.

Example 34 In place of 3,4,5-trimethoxybenzoyl chloride in Example 25, 20 mg of m-anisoyl chloride was used.
The same operation as described above was carried out to obtain 21 mg of 8-deoxy-14-O-m-anisoylaconine.

Example 35 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. 8-Deoxyaconine (50 mg) and p-toluenesulfonic acid (20 mg) were dissolved in acetic anhydride (1.5 mgl) and dissolved at room temperature.
Stir for hours. 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 8-deoxy-
35 mg of 14-O-acetylaconin are obtained.

Example 36 The same operation as in Example 1 was carried out to obtain 8-deoxyaconine. Dissolve 30 mg of 8-deoxyaconin in 3.6 ml of 1,2-dimethylethane, add 90 mg of sodium hydride,
Stir for 30 minutes at room temperature. The reaction solution was added with 1-bromide-4-
Add 0.9 ml of methylpentane 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 8-deoxy-14-O- (4-methylpentyl).
15 mg of aconine is obtained.

Example 37 The same operation as in Example 1 was carried out, except that 8-deoxy-14-O
-To obtain anisoyl aconin; 8-deoxy-14-O-
Dissolve 660 mg of anisoyl aconin in 66 ml of acetone, and add potassium permanganate aqueous solution (887 mg / water 25 ml) to this solution.
25 ml and 4.5 ml of an aqueous potassium carbonate solution (55.6 mg / 45 ml of water) are added, and the mixture is stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture is concentrated under reduced pressure until the acetone odor disappears, 33 ml of 2N sulfuric acid and 22 ml of sodium thiosulfate aqueous solution (887 mg / 22 ml of water) are added to the residue, and the mixture is washed with methylene chloride. The aqueous layer is adjusted 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 649 mg of N-desethyl-8-deoxy-14-O-anisoylaconine.

Example 38 The same operation as in Example 37 was carried out, except that N-desethyl-8-
Deoxy-14-O-anisoylaconine is obtained. N-desethyl-8-deoxy-14-O-anisoylaconine
Dissolve 2mg of 50mg methanol / ether (1: 1) mixture,
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), separated and purified, and N-desethyl-N-amyl-8-deoxy-14 was purified.
28 mg of -O-anisoylaconine are obtained.

Example 39 The procedure of Example 38 was repeated, except that 0.5 ml of n-propyl iodide was used in place of the n-amyl iodide of Example 38, except that N-desethyl-N-propyl-8-deoxy was used. −14
26 mg of -O-anisoylaconine are obtained.

Example 40 1-bromide-4 in place of n-amyl iodide of Example 38
N-desethyl-N-methylpentyl-8 was prepared in the same manner as in Example 38 except that 0.5 ml of methylpentane was used.
32 mg of -deoxy-14-O-anisoylaconine are obtained.

Example 41 The same operation as in Example 37 was carried out, except that N-desethyl-8-
Deoxy-14-O-anisoylaconine is obtained. N-desethyl-8-deoxy-14-O-anisoylaconine
Dissolve 50mg in 1ml of methanol, potassium carbonate 50mg, water
Add 0.1 ml and 20 μl of acetyl chloride and stir 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-8-deoxy-
32 mg of 14-O-anisoylaconine are obtained.

(Example 42) Instead of acetyl chloride of Example 41, benzoyl chloride was used.
Using 20 μl, operating in exactly the same manner as in Example 41,
Desethyl-N-benzoyl-8-deoxy-14-O-
28 mg of anisoyl aconin are obtained.

Example 43 The procedure of Example 13 was repeated, except that 80 mg of 16-epi-pyrogesaconitine was used in place of 60 mg of 16-epi-pyrogesaconitine. -60 mg of deoxyaconine are obtained. 60 mg of 16-epi-8-deoxyaconine is dissolved in 1 ml of pyridine, 30 mg of 3,4,5-trimethoxybenzoyl 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 was subjected to silica gel column chromatography (ammonia saturated ether), separated and purified, and 16-epi-8-deoxy-14 was purified.
26 mg of -O-trimethylgalloylaconin are obtained.

(Example 44) Instead of 3,4,5-trimethoxybenzoyl chloride of Example 43, using 25 mg of 3,4-dimethoxybenzoyl chloride,
Otherwise, operating exactly as in Example 43, 23 mg of 16-epi-8-deoxy-14-O-veratroyl aconin are obtained.

Example 45 The procedure of Example 43 was repeated, except that 20 mg of p-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride of Example 43. Deoxy-
22 mg of 14-Op-chlorobenzoyl aconine are obtained.

Example 46 The procedure of Example 43 was repeated, except that 20 mg of m-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride. Deoxy-
21 mg of 14-O-m-chlorobenzoyl aconine are obtained.

[Example 47] In place of 3,4,5-trimethoxybenzoyl chloride in Example 43, α-methyl- (4- (α-methylaceticaside) -phenyl) -acetyl 50 μl was used. By exactly the same operation as in Example 43, 22 mg of 16-epi-8-deoxy-14-O-α-methyl- (4- (α-methylacetylic acid) -phenyl) -acetylaconine is obtained.

Example 48 The same procedure as in Example 13 was repeated, except that 80 mg of 16-epi-pyrogesaconitine was used in place of 60 mg of 16-epi-pyrogesaconitine in Example 13, except that 16-epi-8 was used. -60 mg of deoxyaconine are obtained. Dissolve 15 mg of 16-epi-8-deoxyaconin in 1 ml of dioxane and add 15 m of sodium hydride.
Add g, bring to room temperature and stir 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-deoxy-14-.
11 mg of O-methylaconine are obtained.

Example 49 The same procedure as in Example 13 was repeated except that 80 mg of 16-epi-pyrogesaconitine was used in place of 60 mg of 16-epi-pyrogesaconitine in Example 13, and 16-epi-8 was used. -60 mg of deoxyaconine are obtained. 30 mg of 16-epi-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 heated under reflux 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 subjected to silica gel column chromatography (ammonia-saturated chloroform)
Separation and purification in 16-epi-8-deoxy-14-O-
18 mg of benzylaconine are obtained.

Example 50 16-epi-pyrogesaconitine was replaced with 60 mg of 16-epi-pyrrogesaconitine in Example 13 except that 80-mg was used. Obtaining deoxyaconine; 16-epi-8-deoxyaconine 17
mg was dissolved in 2 ml of 1,2-dimethoxyethane, 50 mg of sodium hydride was added, and the mixture was stirred at room temperature for 30 minutes. 0.5 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 12 mg of 16-epi-8-deoxy-14-O-crotyl aconine.

Example 51 The procedure of Example 43 was repeated, except that 20 mg of o-chlorobenzoyl chloride was used instead of 3,4,5-trimethoxybenzoyl chloride of Example 43. Deoxy-
22 mg of 14-OO-chlorobenzoyl aconine are obtained.

Example 52 Instead of 3,4,5-trimethoxybenzoyl chloride of Example 43, 20 mg of m-anisoyl chloride was used.
The procedure was identical to that for 16-epi-8-deoxy-14-O.
20 mg of m-anisoylaconine are obtained.

Example 53 The same procedure as in Example 13 is carried out to obtain 16-epi-8-deoxy-14-O-anisoylaconine. 16-Epi-8
-Deoxy-14-O-anisoylaconine (660 mg) was dissolved in acetone (66 ml), and potassium permanganate aqueous solution (887 mg / water 25 ml) (25 ml) and potassium carbonate aqueous solution (5
(5.6 mg / 45 ml of water) and add 4.5 ml, and stir 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 residual liquid was cooled in advance with 2N sulfuric acid 33.
ml and sodium thiosulfate aqueous solution (887mg / water 22ml) 22ml
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)
Separation and purification give 640 mg of 16-epi-N-desethyl-8-deoxy-14-O-anisoylaconine.

[Example 54] By exactly the same operation as in Example 53, 16-epi-N-desethyl-8-deoxy-14-O-anisoylaconine is obtained. 16-epi-N-desethyl-8-deoxy-14-O
-50 mg of anisoyl aconin in methanol / ether (1:
1) Dissolve in 2 ml of the mixture, and add 65 mg of calcium carbonate 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, and 25 mg of 16-epi-N-desethyl-N-amyl-8-deoxy-14-O-anisoylaconine. Get.

Example 55 The same procedure as in Example 53 is carried out to obtain 16-epi-N-desethyl-8-deoxy-14-O-anisoylaconine. N-desethyl-8-deoxy-14-O of Example 39
-50 mg of 16-epi-N-desethyl-8-deoxy-14-O-anisoylaconine instead of anisoylaconine
And operating exactly as in Example 39, except that
N-desethyl-N-propyl-8-deoxy-14-O
28 mg of anisoyl aconin are obtained.

Example 56 Instead of n-amyl iodide of Example 55, 1-bromide-
Using exactly the same procedure as in Example 55 except for using 0.5 ml of 4-methylpentane, the procedure was repeated except that 16-epi-N-desethyl-N- (4-
30 mg of (methyl) pentyl-8-deoxy-14-O-anisoylaconine are obtained.

Example 57 The same procedure as in Example 53 is carried out to obtain 16-epi-N-desethyl-8-deoxy-14-anisoylaconine.
Instead of N-desethyl-8-deoxy-14-O-anisoylaconine of Example 41, 50 mg of 16-epi-N-desethyl-8-deoxy-14-anisoylaconine was used,
Otherwise operating exactly as in Example 41, 29 mg of 16-epi-N-desethyl-N-acetyl-8-deoxy-14-O-anisoylaconine are obtained.

Example 58 Benzoyl chloride 20 in place of acetyl chloride of Example 57
Using the same procedure as in Example 57 but using 16 μl of 16-epi-N-desethyl-N-benzoyl-8-deoxy-
27 mg of 14-O-anisoylaconin are obtained.

Example 59 The same procedure as in Example 31 was repeated, except that 50 μl of p-methoxybenzyl chloride was used instead of benzyl chloride of Example 31, to obtain 17 mg of 8-deoxy-14-Op-methoxybenzylaconine. Get.

Example 60 The procedure of Example 36 was repeated, except that 0.5 ml of n-amyl iodide was used instead of 1-brom-4-methylpentane of Example 36. 16 mg of -O-amyl aconin are obtained.

Example 61 Instead of -m-chlorobenzoyl chloride of Example 28,
Using 20 mg of m-bromobenzoyl chloride, otherwise
By exactly the same procedure as described above, 19 mg of 8-deoxy-14-O-m-bromobenzoylaconine was obtained.

Example 62 Instead of -m-chlorobenzoyl chloride of Example 28,
Using 20 mg of m-fluorobenzoyl chloride;
Operating exactly as in 28, 21 mg of 8-deoxy-14-O-m-fluorobenzoylaconine are obtained.

Example 63 Instead of 3-deoxygesaconitine in Example 3
The same operation as in Example 3 was carried out except that 100 mg of 3,13-dideoxyjesaconitine was used to obtain 62 mg of 3,13-dideoxypyrogesaconitine. Next, 3,8,13-trideoxyaconine was used in the same manner as in Example 1 except that 60 mg of 3,13-dideoxypyrrojesaconitine was used in place of the pyrogenesaconitine of Example 1. Obtain 48 mg.

30 mg of 3,8,13-trideoxyaconin was dissolved in 1 ml of pyridine, and 30 mg of 3,4-dimethoxybenzoyl chloride was added thereto.
Stir at 0 ° 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,
3,8,13-trideoxy-14-O-veratroyl aconine
Obtain 19 mg.

[Example 64] By exactly the same operation as in Example 63, 3,8,13-trideoxyaconine is obtained. 3,8,13-Trideoxyaconine 30mg
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).
3,8,13-Trideoxy-14-O-acetylaconine 31 mg
Get.

Example 65 3,8,13-Trideoxy was prepared in the same manner as in Example 63 except that 30 mg of m-chlorobenzoyl chloride was used in place of the 3,4-dimethoxybenzoyl chloride of Example 63. −14
2.0 mg of -O-m-chlorobenzoylaconine are obtained.

Example 66 The procedure of Example 63 is repeated to obtain 3,8,13-trideoxyaconine. 3,8,13-Trideoxyaconine 30mg
Is dissolved in 1,2-dimethoxyethane (2 ml), sodium hydride (60 mg) 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 heated under reflux 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 is separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to obtain 3,8,13-trideoxy-14-O-benzylaconine (15 mg).

[Example 67] By exactly the same operation as in Example 63, 3,8,13-trideoxyaconine is obtained. 3,8,13-Trideoxyaconine 30mg
Was dissolved in 3.6 ml of 1,2-dimethoxyethane, 90 mg of sodium hydride was added, and the mixture was stirred at room temperature for 30 minutes. 0.9 ml of 1-bromo-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 3,8,13-trideoxy-14-O
14 mg of-(4-methylpentyl) aconin are obtained.

Example 68 The procedure of Example 63 is repeated to obtain 3,8,13-trideoxyaconine. 3,8,13-Trideoxyaconine 30mg
Is dissolved in 1,2-dimethoxyethane (4 ml), sodium hydride (50 mg) 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 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 is separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to obtain 3,8,13-trideoxy-14-O-crotyl aconin (15 mg).

Example 69 The same operation as in Example 3 is performed to obtain 3,8-dideoxy-14-O-anisoylaconine. 140 mg of 3,8-dideoxy-14-O-anisoylaconine was added to 5 ml of methanol.
And 1 ml of 5% potassium hydroxide is added, and the mixture is refluxed for 3 hours. After distilling off the methanol in the reaction solution under reduced pressure,
5 ml of water is added, and the mixture is 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) to separate and purify.
62 mg of 8-dideoxyaconin are obtained.

Dissolve 50 mg of 3,8-dideoxyaconin in 1 ml of pyridine, add 30 mg of 3,4-dimethoxybenzoyl chloride, and add
And stir 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), and separated and purified.
22 mg of -dideoxy-14-O-veratroyl aconin are obtained.

Example 70 The same operation as in Example 69 is performed to obtain 3,8-dideoxyaconine. The procedure of Example 35 was repeated, except that 50 mg of 3,8-dideoxyaconine was used instead of 8-deoxyaconine in Example 35, and 3,8-dideoxy-14-O-
37 mg of acetylaconin are obtained.

[Example 71] Instead of 3,4-dimethoxybenzoyl chloride of Example 69, 28-mg-chlorobenzoyl chloride was used, and the other procedures were carried out exactly as in Example 69, to give 3,8-dideoxy-14-. O-
23 mg of m-chlorobenzoylaconine are obtained.

Example 72 The same procedure as in Example 69 is carried out to obtain 3,8-dideoxyaconine. Instead of 3,8,13-trideoxyaconine of Example 66, using 30 mg of 3,8-dideoxyaconine,
Otherwise, operating exactly as in Example 66, 3,8-dideoxy-1
18 mg of 4-O-benzylaconine are obtained.

Example 73 The same procedure as in Example 69 is performed to obtain 3,8-dideoxyaconine. Instead of 3,8,13-trideoxyaconine in Example 67, using 30 mg of 3,8-dideoxyaconine,
Otherwise, operating exactly as in Example 67, 3,8-dideoxy-1
17 mg of 4-O- (4-methyl) pentylaconine are obtained.

[Example 74] By operating exactly as in Example 69, 3,8-dideoxyaconine is obtained. Instead of 3,8,13-trideoxyaconine of Example 68, using 30 mg of 3,8-dideoxyaconine,
Otherwise operating exactly as in Example 68, but with 3,8-dideoxy-1
17 mg of 4-O-crotyl aconin are obtained.

[Example 75] 16-epi-8-deoxyaconine is obtained in exactly the same manner as in Example 13. Using 30 mg of 16-epi-8-deoxyaconine instead of 8-deoxyaconine in Example 59,
Otherwise operate exactly as in Example 59 to obtain 15 mg of 16-epi-8-deoxy-14-Op-methoxybenzylaconine.

Example 76 The procedure of Example 13 is repeated to obtain 16-epi-8-deoxyaconine. Substituting 30 mg of 16-epi-8-deoxyaconin for the 8-deoxyaconin of Example 60,
Otherwise operate exactly as in Example 60 to obtain 15 mg of 16-epi-8-deoxy-14-O-amyl aconin.

Example 77 Instead of 3-deoxygesaconitine in Example 14
The same operation as in Example 14 was carried out except that 150 mg of 3,13-dideoxyjesaconitine was used to obtain 61.7 mg of 16-epi-3,13-dideoxypyrogesaconitine. Next, using 16-epi-3,13-dideoxypyrogesaconitine instead of 16-epipyrogesaconitine in Example 13, 60 mg
Otherwise, the same operation as in Example 13 was performed, and 16-epi-3,
50.1 mg of 8,13-trideoxyaconin are obtained.

Dissolve 30 mg of 16-epi-3,8,13-trideoxyaconine in 1 ml of pyridine and 30 mg of 3,4-dimethoxybenzoyl 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. 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).
Purification gives 19 mg of 16-epi-3,8,13-trideoxy-14-O-veratroyl aconin.

Example 78 The procedure of Example 77 was repeated, except that 30 mg of m-chlorobenzoyl chloride was used in place of the 3,4-dimethoxybenzoyl chloride of Example 77, except that 16-epi-3,8 was used. , 13-Trideoxy-14-O-m-chlorobenzoylaconine 2.1 mg
Get.

Example 79 The same procedure as in Example 77 was carried out, except that 16-epi-3,8,13-
Obtain trideoxyaconine. 30 mg of 16-epi-3,8,13-trideoxyaconine 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,
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 was separated and purified by silica gel column chromatography (ammonia-saturated chloroform) to give 16-epi-3,8,13-
16 mg of trideoxy-14-O-benzylaconine are obtained.

Example 80 The same operation as in Example 77 was carried out, except that 16-epi-3,8,13-
Obtain trideoxyaconine. 30 mg of 16-epi-3,8,13-trideoxyaconine 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 was added to the reaction solution, and 30
Heat to reflux for 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 separated and purified by silica gel column chromatography (5% methanol / ammonia-saturated chloroform).
-16 mg of epi-3,8,13-trideoxy-14-O-crotyl aconin are obtained.

Example 81 Instead of 3-deoxygesaconitine in Example 14, 150 mg of 3,13-deoxyaconitine was used, and the other operations were carried out in exactly the same manner as in Example 14 to obtain 16-epi-3-deoxypyrroconitine. 66.5 mg of aconitine are obtained. Next, 16 of Example 13
16-epi-3- instead of epipyrogesaconitine
Except that 60 mg of deoxypyroaconitine is used, the procedure is exactly the same as that of Example 13 to obtain 47.2 mg of 16-epi-3,8-dideoxyaconine.

16-epi-3,8-dideoxyaconine 40 mg was added to pyridine 1
The mixture was dissolved in ml, and 3,4-dimethoxybenzoyl chloride (30 mg) was added, followed by stirring 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 20 mg of 16-epi-3,8-dideoxy-14-O-veratroyl aconin.

Example 82 The procedure of Example 81 was repeated, except that 28 mg of -m-chlorobenzoyl chloride was used instead of 3,4-dimethoxybenzoyl chloride of Example 81. 2.2 mg of dideoxy-14-O-m-chlorobenzoylaconine are obtained.

[Example 83] By exactly the same operation as in Example 81, 16-epi-3,8-dideoxyaconine is obtained. Instead of 3,8,13-trideoxyaconine of Example 66, 30 mg of 16-epi-3,8-dideoxyaconine was used, and the other procedure was carried out exactly as in Example 66, except that 116-epi-3 19 mg of, 8-dideoxy-14-O-benzylaconine are obtained.

[Example 84] By exactly the same operation as in Example 81, 16-epi-3,8-dideoxyaconine is obtained. Instead of 3,8,13-trideoxyaconine of Example 68, 30 mg of 16-epi-3,8-dideoxyaconine was used. 15 mg of, 8-dideoxy-14-O-crotyl aconin are obtained.

Example 85 The procedure of Example 3 was repeated, except that 3,8-dideoxy-14 was used.
-O-Anisoyl aconine is obtained. 3,8-dideoxy-1
660 mg of 4-O-anisoylaconine was dissolved in 66 ml of acetone, and an aqueous solution of potassium permanganate (887 mg / water) was added to this solution.
25ml) 25ml and aqueous potassium carbonate solution (55.6mg / water 45ml)
Add 4.5 ml and stir at room temperature for 30 minutes. After the reaction,
The reaction solution was concentrated under reduced pressure until the acetone odor disappeared.
33 ml of 2N sulfuric acid and 22 ml of sodium thiosulfate aqueous solution (887 mg / water 22 ml) cooled in advance are added to the remaining liquid, 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 630 mg of N-desethyl-3,8-dideoxy-14-O-anisoylaconine.

Example 86 The same operation as in Example 85 was carried out, except that N-desethyl-3,8
-Dideoxy-14-O-anisoylaconine is obtained. N
Dissolve 50 mg of -desethyl-3,8-dideoxy-14-O-anisoylaconin in 2 ml of a methanol / ether (1: 1) mixture, and obtain 65 mg of calcium carbonate and 0.2 m of n-amyl iodide.
Add l 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)
Separation and purification give 25 mg of N-desethyl-N-amyl-3,8-dideoxy-14-O-anisoylaconine.

Example 87 N-desethyl-N-propyl-3,8 was operated in the same manner as in Example 86 except that 0.5 ml of n-propyl iodide was used in place of n-amyl iodide of Example 86. 22 mg of -dideoxy-14-O-anisoylaconine are obtained.

Example 88 1-Bromide-4 in place of n-amyl iodide of Example 86
-Using 0.5 ml of methylpentane and operating in exactly the same manner as in Example 86 except that 31 mg of N-desethyl-N-4-methylpentyl-3,8-dideoxy-14-O-anisoylaconine was used.
Get.

Example 89 The same operation as in Example 85 was carried out, except that N-desethyl-3,8
-Dideoxy-14-O-anisoylaconine is obtained. N
Dissolve 50 mg of desethyl-3,8-dideoxy-14-O-anisoylaconine in 1 ml of methanol and add potassium carbonate 5
0 mg, 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, N-desethyl-N-acetyl-3,8-
30 mg of dideoxy-14-O-anisoylaconine are obtained.

Example 90 Instead of acetyl chloride of Example 89, benzoyl chloride was used.
Using 20 μl, operating in exactly the same manner as in Example 89,
Desethyl-N-benzoyl-3,8-dideoxy-14-
25 mg of O-anisoylaconine are obtained.

Example 91 The same operation as in Example 2 was performed to obtain 3,8,13-trideoxy-14-O-anisoylaconine. 660 mg of 3,8,13-trideoxy-14-O-anisoylaconine was added to acetone 6
Dissolve in 6 ml, add 25 ml of potassium permanganate aqueous solution (887 mg / water 25 ml) and potassium carbonate aqueous solution (55.6 mg
(45 ml of water / 45 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 33 ml of 2N sulfuric acid and 22 ml of sodium thiosulfate aqueous solution (887 mg / 22 ml of water) were added to the remaining solution.
Wash with methylene chloride. PH of aqueous layer with sodium carbonate
Prepare 8-9 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 N-desethyl-3,8,13-trideoxy-14-O-
620 mg of anisoyl aconin are obtained.

Example 92 The same operation as in Example 91 was carried out, except that N-desethyl-3,8,
13-Trideoxy-14-O-anisoylaconine is obtained. N-desethyl-3,8,13-trideoxy-14-O-
Anisoyl aconin (50 mg) was dissolved in methanol / ether (1:
1) Dissolve in 2 ml of the mixture, and add 65 mg of calcium carbonate 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, and N-desethyl-N-amyl-3,8,13-trideoxy-14-O-anisoylaconine was added in an amount of 21 mg. Get.

Example 93 The procedure of Example 92 was repeated, except that 0.5 ml of n-propyl iodide was used in place of the n-amyl iodide of Example 92. N-desethyl-N-propyl-3,8 20 mg of, 13-trideoxy-14-O-anisoylaconine are obtained.

Example 94 1-bromide-4 in place of n-amyl iodide of Example 92
-N-desethyl-N-4-methylpentyl-3,8,13-trideoxy-14-O-anisoylaconine using the same procedure as in Example 92 except that 0.5 ml of methylpentane was used.
Obtain 31 mg.

Example 95 The same operation as in Example 91 was carried out, except that N-desethyl-3,8,
13-Trideoxy-14-O-anisoylaconine is obtained. N-desethyl-3,8,13-trideoxy-14-O-
Anisoyl aconin (50 mg) is dissolved in methanol (1 ml), potassium carbonate (50 mg), water (0.1 ml) and acetyl chloride (20 μl) 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, and the residue was dissolved in chloroform (20 ml).
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-O-anisoylaconine was added in an amount of 28 mg. Get.

Example 96 Instead of acetyl chloride of Example 95, benzoyl chloride was used.
Using 20 μl, otherwise operating exactly as in Example 95,
Desethyl-N-benzoyl-3,8,13-trideoxy-
25 mg of 14-O-anisoylaconine are obtained.

Example 97 The same operation as in Example 14 was carried out to obtain 16-epi-3,8-dideoxy-14-O-anisoylaconine. 660 mg of 16-epi-3,8-dideoxy-14-O-anisoylaconine
Is dissolved in 66 ml of acetone, 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 (55.6 mg / 45 ml of water) are added to the solution, and the mixture is stirred at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure until the acetone odor disappeared, and 2N sulfuric acid previously cooled was added to the residual liquid.
33ml and sodium thiosulfate aqueous solution (887mg / water 22ml) 22
Add 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 615 mg of N-desethyl-16-epi-3,8-dideoxy-14-O-anisoylaconine.

Example 98 The same operation as in Example 97 was carried out, except that N-desethyl-16-
This gives epi-3,8-dideoxy-14-O-anisoylaconine. 50 mg of N-desethyl-16-epi-3,8-dideoxy-14-O-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 silica gel column chromatography (5% methanol / ammonia-saturated chloroform) to separate and purify, and N-desethyl-N
21 mg of amyl-16-epi-3,8-dideoxy-14-O-anisoylaconine are obtained.

Example 99 The same procedure as in Example 98 was repeated, except that 0.5 ml of n-propyl iodide was used in place of n-amyl iodide of Example 98, and N-desethyl-N-propyl-16-epi was obtained. −3,8−
23 mg of dideoxy-14-O-anisoylaconine are obtained.

Example 100 1-bromide-4 in place of n-amyl iodide of Example 98
N-desethyl-N-4-methylpentyl-16-epi-3,8-dideoxy-14-O-anisoylaconine 29 mg using the same procedure as in Example 98 except that 0.5 ml of -methylpentane was used. Get.

Example 101 The same procedure as in Example 97 was carried out, except that N-desethyl-16-
This gives epi-3,8-dideoxy-14-O-anisoylaconine. 50 mg of N-desethyl-16-epi-3,8-dideoxy-14-O-anisoylaconine was dissolved in 1 ml of methanol, 50 mg of potassium carbonate, 0.1 ml of water and 2 ml of acetyl chloride.
Add 0 μl and stir at room temperature for 1 hour. After the reaction,
The reaction solution was concentrated to dryness under reduced pressure, and the residue was chloroform 20 ml.
, 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-16-epi-3,8-dideoxy-14-O-
31 mg of anisoyl aconin are obtained.

[Example 102] Instead of acetyl chloride of Example 101, benzoyl chloride (20 µl) was used, and the other operations were performed in the same manner as in Example 101.
22 mg of N-desethyl-N-benzoyl-16-epi-3,8-dideoxy-14-O-anisoylaconine are obtained.

Example 103 The same operation as in Example 15 was carried out to obtain 16-epi-3,8,13-trideoxy-14-O-anisoylaconine. 16−
660 mg of epi-3,8,13-trideoxy-14-O-anisoylaconine was dissolved in 66 ml of acetone, and 25 ml of an aqueous potassium permanganate solution (887 mg / 25 ml of water) and an aqueous solution of potassium carbonate (55.6 mg / 45 ml of water) were added to the solution. ) Add 4.5ml and at room temperature
Stir 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 sodium thiosulfate aqueous solution (887 mg /
22 ml of water) is added, 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, and N-desethyl-16-epi-
3,8,13-Trideoxy-14-O-anisoylaconine 61
Get 5 mg.

Example 104 The same operation as in Example 103 was carried out, except that N-desethyl-16 was used.
-To obtain epi-3,8,13-trideoxy-14-O-anisoylaconine. N-desethyl-16-epi-3,8,13-
50 mg of trideoxy-14-O-anisoylaconine is dissolved in 2 ml of a mixture of methanol and 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 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-3,8,13-trideoxy-14-O-aniline was purified. 21 mg of soil aconin are obtained.

Example 105 Instead of n-amyl iodide of Example 104, n-iodide was used.
Proceeding exactly as in Example 104 except using 0.5 ml of propyl, n-desethyl-N-propyl-16-epi-3,8,13
20 mg of -trideoxy-14-O-anisoylaconine are obtained.

Example 106 1-bromide-in place of n-amyl iodide of Example 104
N-desethyl-N-4-methylpentyl-16-epi-3,8,13-trideoxy-14-O-anisoyl was obtained in the same manner as in Example 104 except that 0.5 ml of 4-methylpentane was used. 29 mg of aconine are obtained.

Example 107 The same operation as in Example 103 was carried out, except that N-desethyl-16
To obtain epi-3,8,13-trideoxy-14-O-anisoylaconine. 50 mg of N-desethyl-16-epi-3,8,13-trideoxy-14-O-anisoylaconin was dissolved in 1 ml of methanol, 50 mg of potassium carbonate, 0.1 ml of water and 20 μl of acetyl chloride were added, and the mixture was added at room temperature for 1 hour. Stir. 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-3,8,13-trideoxy-14-O-aniline was purified. 25 mg of soil aconin are obtained.

[Example 108] In place of acetyl chloride of Example 107, benzoyl chloride (20 µl) was used, and the other procedures were the same as in Example 95.
22 mg of -desethyl-N-benzoyl-16-epi-3,8,13-trideoxy-14-O-anisoylaconine are obtained.

Example 109 The same operation as in Example 37 was carried out, except that N-desethyl-8-
Deoxy-14-O-anisoylaconine is obtained. N-desethyl-8-deoxy-14-O-anisoylaconine
Dissolve 50 mg in methanol 1 ml, potassium carbonate 50 mg, water
Add 0.1 ml and 20 μl of 2-methyl-tetrahydro-2-furoyl chloride and stir at room temperature for 1 hour. After completion of the reaction, the reaction solvent was distilled off under reduced pressure.
The chloroform layer is washed with 5% hydrochloric acid and water, 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 previously charged with 0.7 mg of lithium aluminum hydride (20 mg).
of the suspension in l. tetrahydrofuran while cooling and heating at 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 was concentrated to dryness under reduced pressure, and the residue was dissolved in 1 ml of pyridine.
and stirred at room temperature for 4 hours. After completion of the reaction, pyridine in the reaction solution is distilled off under reduced pressure, water is added, the mixture is made alkaline with 5% sodium hydrogen carbonate, and extracted 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) to give N-desethyl-N- (2-methyltetrahydrofurfuryl) -8.
2.1 mg of -deoxy-14-O-anisoylaconine are obtained.

Example 110 The same operation as in Example 85 was carried out, except that N-desethyl-3,8
-Dideoxy-14-O-anisoylaconine is obtained. Instead of N-desethyl-8-deoxy-14-O-anisoylaconine of Example 109, 50 mg of N-desethyl-3,8-dideoxy-14-O-anisoylaconine was used. The same operation as described above was performed, and N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,8-
2.0 mg of dideoxy-14-O-anisoylaconine are obtained.

Example 111 The same operation as in Example 91 was carried out, except that N-desethyl-3,8,
13-Trideoxy-14-O-anisoylaconine is obtained. Example 109 N-desethyl-8-deoxy-14-
N-desethyl-3, instead of O-anisoylaconine
8,13-Trideoxy-14-O-anisoylaconine 50 mg
The same operation as in Example 109 was performed except for using N-
1.8 mg of desethyl-N- (2-methyltetrahydrofurfuryl) -3,8,13-trideoxy-14-O-anisoylaconine are obtained.

Example 112 The same procedure as in Example 53 was carried out, except that N-desethyl-16-
This gives epi-8-deoxy-14-O-anisoylaconine. Example 109 N-desethyl-8-deoxy-14-
N-desethyl-16 instead of O-anisoylaconine
-Epi-8-deoxy-14-O-anisoylaconine 50
The same operation as in Example 109 was performed except for using
2.3 mg of -desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-8-deoxy-14-O-anisoylaconine are obtained.

[Example 113] The same operation as in Example 97 was carried out, except that N-desethyl-16-
This gives epi-3,8-dideoxy-14-O-anisoylaconine. N-desethyl-8-deoxy-1 of Example 109
Using exactly the same procedure as in Example 109 except for using 50 mg of N-desethyl-16-epi-3,8-dideoxy-14-O-anisoylaconine instead of 4-O-anisoylaconine, N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-3,8-dideoxy-14-O-
1.9 mg of anisoyl aconin are obtained.

Example 114 The procedure of Example 103 was repeated, except that N-desethyl-16 was used.
To obtain epi-3,8,13-trideoxy-14-O-anisoylaconine. Using N-desethyl-16-epi-3,8,13-trideoxy-14-O-anisoylaconine instead of N-desethyl-8-deoxy-14-O-anisoylaconine in Example 109 Other than that, the same operation as in Example 109 was carried out, and N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-3,8,13-trideoxy-14-O-anisoylaconine 1.7 was obtained. get mg.

Next, the physical property values and analytical data of the compounds of each Example are shown. The numbers in parentheses attached to the respective compounds correspond to the numbers in Examples.

(1) Physical property values and analytical data of 8-deoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, 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 1711 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.43 (1H, d, J = 4.95) (βH at position 14) 3.87 (3H, s,) (H of the methoxy group of the anisoyl group) 1.11 (3H, t, J = 6.93) (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 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,
14,18,13,15,3 position C) 61.8,59.1,57.9,56.1 (C derived from methoxy group bonded to 16,18,6,1 position) 55.4 (C of anisoyl group methoxy group) 49.1 ( N-ethyl group methylene C) 13.4 (N-ethyl group methyl C) 6) Mass spectrometry m / z 617 (M ⁺ ) (2) 3,8,13-Trideoxy-14-O-anisoyl Physical properties and analytical data of 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 3500 and 1711 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.01 (1H, t, J = 4.53) (βH at position 14) 3.87 (3H, s,) (H of methoxy group of anisoyl group) 1.10 (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).

166.0 (C of anisoyl group carbonyl) 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 the 16,1,6,18,14,15 position) 59.1 , 58.3, 58.0, 56.1 (C of the methoxy group bonded to the 16, 18, 6, 6 and 1 positions) 55.3 (C of the methoxy group of anisoyl group) 49.1 (C of the methylene of N-ethyl group) 13.4 (N-ethyl group 6) Mass spectrometry m / z 585 (M ⁺ ) (3) Physical properties and analytical data of 3,8-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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.45 (1H, d, J = 4.95) (βH at position 14) 3.87 (3H, s,) (H of the methoxy group of the anisoyl group) 1.10 (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).

165.9 (C of anisoyl group carbonyl) 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, (16,1,6,18,14,13,15 C) 61.8,59.1,57.9,56.1 (C of the methoxy group bonded to the 16,18,6,1 position) 55.4 (C of the methoxy group of anisoyl group) 49.1 (C of the methylene group of N-ethyl group) 13.4 (C of methyl of N-ethyl group) 6) Mass spectrometry m / z 601 (M ⁺ ) (4) Physical property value and analytical data of 8-deoxy-14-O-benzoyl aconine 1) Property 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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 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).

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
14,18,13,15,3 position C) 60.9,59.0,57.9,56.1 (C of methoxy group bonded to 16,18,6,1 position) 49.0 (C of N-ethyl group methylene) 13.5 ( C) 6) Mass spectrometry m / z 587 (M ⁺ ) (5) Physical property value and analytical data of 3,8-dideoxy-14-O-benzoylaconine 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 3500 and 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.08 (3H, t, J = 6.98) (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 of 16,1,6,18,14,15 position) 60.9 , 59.0, 57.9, 56.1 (C of methoxy group attached to the 16, 18, 6, and 1 positions) 49.0 (C of N-ethyl group of methylene) 13.5 (C of N-ethyl group of methyl) 6) Mass spectrum analysis m / z 571 (M ⁺ ) (6) Physical property values and analytical data of 3,8,13-trideoxy-14-O-benzoylaconine 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 3450 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.07 (3H, t, J = 6.98) (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 benzoyl group carbonyl) 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 the 16,1,6,18,14,15 position) 59.2 , 57.9, 57.6, 56.0 (C of methoxy group attached at 18, 16, 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 555 (M ⁺ ) (7) Physical property values and analytical data of 8-deoxy-14-O-benzoylaconine 1) Properties and solubility A colorless non-crystalline powder, 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 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 (C at position 16,16,1,14,18,13,15) 60.7,58.8,57.8,55.8 (C of methoxy group bonded to the 16,18,6,1 position) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 573 (M ⁺ ) (8) Physical property value and analytical data of 3,8,13-trideoxy-14-O-benzoylmesaconin 1) Properties and solubility A colorless non-crystalline powder, 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 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 benzoyl group carbonyl) 133.0,129.6,128.3, (C of benzoyl group) 93.1,85.3,84.4,80.3,80.0,72.1 (C at position 16,1,6,18,14,15) 59.0, 58.0,57.7,56.5 (C of methoxy group bonded to the 18,16,6,1 position) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 541 (M ⁺ ) (9) 3,8 Physical properties and analytical data of -dideoxy-14-O-benzoylmesaconin 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 3450 and 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 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).

165.8 (C of the carbonyl of the benzoyl group) 133.0, 129.5, 128.3, (C of the benzoyl group) 94.2, 85.2, 84.2, 80.0, 74.0, 72.6 (C at the 16,1,6,18,14,13,15 position) 60.8,58.9,57.7,55.6 (C of methoxy group bonded at 16,18,6,1 position) 42.5 (C of N-methyl group) 6) Mass spectrum analysis m / z 557 (M ⁺ ) (10) 8 Physical properties and analytical data of -deoxy-14-O-anisoylmesaconin 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 3450 and 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.46 (1H, d, J = 4.95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 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,
14,18,13,15,3 position C) 61.8,59.1,58.0,56.0 (C of methoxy group bonded to 16,18,6,1 position) 55.4 (C of anisoyl group methoxy group) 42.4 (N 6) Mass spectrum analysis m / z 603 (M ⁺ ) (11) Physical property value and analytical data of 3,8-dideoxy-14-O-anisoylmessaconin 1) Property and solubility Colorless Amorphous 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 3450 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.47 (1H, d, J = 4.95) (βH at position 14) 3.88 (3H, s) (H of the methoxy group of the anisoyl group) 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 (16,1,6,18,14,13,15 position C) 61.7,59.0,57.9,56.1 (C of methoxy group bonded to the 16,18,6,1 position) 55.4 (C of methoxy group of anisoyl group) 42.4 (C of N-methyl group) 6) Mass spectrum Analysis m / z 587 (M ⁺ ) (12) Physical property values and analytical data of 3,8,13-trideoxy-14-O-anisoylmesaconin 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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.01 (1H, t, J = 4.50) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 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 of carbonyl) 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 of 16,16,18,14,15 position) 59.2 , 58.0,57.8,56.1 (C of methoxy group bonded to the 16,18,6,1 position) 55.3 (C of methoxy group of anisoyl group) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 571 (M ⁺ ) (13) Physical properties and analytical data of 16-epi-8-deoxy-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 1711 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.68 (1H, d, J = 4.94) (βH at position 14) 3.87 (3H, s) (H of the methoxy group of the anisoyl group) 1.13 (3H, t, J = 6.93) (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) 163.6,131.8,122.2,113.7 (C of anisoyl group) 91.3,85.2,83.7,79.2,77.4,75.9,72.4,72.0 (16,6,1,14,18,13, (C at 15,3 position) 62.2,59.1,57.9,56.1 (C derived from methoxy group bonded at 16,18,6,1 position) 55.4 (C of methoxy group of anisoyl group) 49.1 (methylene of N-ethyl group C) 13.4 (C of N-ethyl group methyl) 6) Mass spectrum analysis m / z 617 (M ⁺ ) (14) Physical properties of 16-epi-3,8-dideoxy-14-O-anisoylaconine Value and analytical data 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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.68 (1H, d, J = 4.95) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 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, (16,1,6,18,14,13,15 C) 61.2,59.1,57.9,56.1 (C of the methoxy group bonded to the 16,18,6,1 position) 55.4 (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 methyl of N-ethyl group) 6) Mass spectrum analysis m / z 601 (M ⁺ ) (15) Physical property values of 16-epi-3,8,13-trideoxy-14-O-anisoylaconine and Analytical data 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 3500 and 1711 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.26 (1H, t, J = 4.53) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 1.10 (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).

165.0 (C of anisoyl group carbonyl) 163.5,131.6,122.1,113.8 (C of anisoyl group) 90.2,85.1,84.5,79.9,78.9,72.0 (C at position 16,16,18,14,15) 59.5 , 58.3, 58.0, 56.1 (C of the methoxy group bonded to the 16, 18, 6, 6 and 1 positions) 55.3 (C of the methoxy group of anisoyl group) 49.1 (C of the methylene of N-ethyl group) 13.4 (N-ethyl group 6) Mass spectrometry m / z 585 (M ⁺ ) (16) Physical properties and analytical data of 16-epi-8-deoxy-14-O-benzoyl aconine 1) Properties and solubility Colorless Amorphous 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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.09 (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).

164.8 (C of benzoyl group carbonyl) 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, 14, 18, 18, 13,15,3 position C) 61.3,59.0,57.9,56.1 (C of methoxy group bonded to 16,18,6,1 position) 49.0 (C of N-ethyl group methylene) 13.5 (N-ethyl group 6) Mass spectrometry m / z 587 (M ⁺ ) (17) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-benzoylaconine 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 3500 and 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.10 (3H, t, J = 6.98) (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 the carbonyl of the benzoyl group) 133.1, 130.0, 129.6, 128.6 (C of the benzoyl group) 91.2, 85.2, 84.2, 80.2, 79.0, 72.6 (C at the 16,1,6,18,14,15 position) 61.2 , 59.0, 57.9, 56.1 (C of methoxy group attached to the 16, 18, 6, and 1 positions) 49.0 (C of N-ethyl group of methylene) 13.5 (C of N-ethyl group of methyl) 6) Mass spectrum analysis m / z 571 (M ⁺ ) (18) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzoylaconine 1) Properties and solubility 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 3450 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 (1H, t, J = 4.49) (βH at position 14) 1.09 (3H, t, J = 6.98) (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 of 16,1,6,18,14,15 position) 59.6 , 57.9, 57.6, 56.0 (C of methoxy group bonded to the 18,16,1 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 555 (M ⁺ ) (19) Physical properties and analytical data of 16-epi-8-deoxy-14-O-benzoylmesaconin 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) (14th position βH) 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 carbonyl 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 (C at position 16,16,1,14,18,13,15) 61.1,58.8,57.8,55.8 (C of methoxy group bonded to the 16,18,6,1 position) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 573 (M ⁺ ) (20) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzoylmesaconin 1) Properties and solubility A colorless amorphous 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 3500 and 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.41-8.22 (5H, m) (benzoyl group H) 5.27 (1H, t, J = 4.28) (βH at position 14) 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 carbonyl) 133.0,129.6,128.3, (C of benzoyl group) 90.1,85.3,84.4,80.3,79.0,72.1 (C at position 16,1,6,18,14,15) 59.5, 58.0, 57.7, 56.5 (C of methoxy group bonded at 18, 16, 6, 1 position) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 541 (M ⁺ ) (21) 16-epi Physical properties and analytical data of -3,8-dideoxy-14-O-benzoylmesaconin 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 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) 2.37 (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 carbonyl) 133.0,129.5,128.3, (C of benzoyl group) 91.0,85.2,84.2,80.2,79.0,75.0,72.6 (16,1,6,18,14,13,15 C) 61.2, 58.9, 57.7, 55.6 (C of methoxy group bonded to the 16, 18, 6, 1-position) 42.5 (C of N-methyl group) 6) Mass spectrum analysis m / z 557 (M ⁺ ) (22 ) Physical properties and analytical data of 16-epi-8-deoxy-14-O-anisoylmesaconin 1) Properties and solubility A colorless amorphous powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, Soluble in pyridine and dimethylsulfoxide, insoluble in hexane and water.

2) Infrared absorption spectrum (KBr) analysis 3) Ultraviolet absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.71 (1H, d, J = 4.95) (βH at position 14) 3.87 (3H, s) (H of the methoxy group of the anisoyl group) 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, 18, 18, 13 (C at 15,3 position) 62.2,59.1,58.0,56.0 (C of methoxy group bonded at 16,18,6,1 position) 55.4 (C of methoxy group of anisoyl group) 42.4 (C of N-methyl group) 6) Mass spectrum analysis m / z 603 (M ⁺ ) (23) Physical property value and analytical data of 16-epi-3,8-dideoxy-14-O-anisoylmessaconin 1) Property and solubility Colorless non-crystal It is soluble powder in ether, chloroform, benzene, ethanol, methanol, ethyl acetate, pyridine, dimethyl sulfoxide and insoluble in hexane and water.

2) Infrared absorption spectrum (KBr) analysis The maximum absorption is shown at 3450, 1710 cm cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.72 (1H, d, J = 4.95) (βH at position 14) 3.88 (3H, s) (H of the methoxy group of the anisoyl group) 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 carbonyl) 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 (16,1,6,18,14,13,15 position C) 62.1, 59.0, 57.9, 56.1 (C of the methoxy group bonded to the 16,18,6,1 position) 55.4 (C of the methoxy group of the anisoyl group) 42.4 (C of the N-methyl group) 6) Mass spectrum Analysis m / z 587 (M ⁺ ) (24) Physical property values and analytical data of 16-epi-3,8,13-trideoxy-14-O-anisoylmesaconin 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 maximum absorption is shown at 3500 and 1710 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.25 (1H, t, J = 4.50) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 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 position 16,16,18,14,15) 59.6 , 58.0,57.8,56.1 (C of methoxy group bonded to the 16,18,6,1 position) 55.3 (C of methoxy group of anisoyl group) 42.3 (C of N-methyl group) 6) Mass spectrum analysis m / z 571 (M ⁺ ) (25) Physical property values and analytical data of 8-deoxy-14-O-trimethylgalloylaconin 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) 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) (H of methoxy group of trimethylgalloyl group) 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 carbonyl) 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, 14 C, 18,13,15,3 position) 61.9,59.3,58.0,55.9 (C derived from methoxy group bonded to 16,18,6,1 position) 55.9 (C of methoxy group of trimethylgalloyl group) 49.0 ( N-ethyl group methylene C) 13.5 (N-ethyl group methyl C) 6) mass spectral analysis 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 (26) Physical properties and analytical data of 8-deoxy-14-O-veratroyl aconin 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) (methoxy group H of veratroyl group) 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 veratroyl group carbonyl) 122.5,110.5,153.1,148.1,112.3 (C of veratroyl group) 94.2,85.0,83.7,80.4,77.4,75.3,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 61.8,59.1,57.9,56.0 (C of methoxy group bonded to 16,18,6,1 position) 55.8 (C of veratroyl group methoxy group) 49.1 (N -Methyl C of ethyl group) 13.4 (C of N-ethyl methyl) 6) Mass spectrum analysis m / z 647 (M ⁺ ) 7) Elemental analysis C ₃₅ H ₄₉ NO ₁₁ , Calculated C: 63.04, H : 7.62, N: 2.16 Found C: 63.21, H: 7.58, N: 2.05 (27) Physical properties and analytical data of 8-deoxy-14-Op-chlorobenzoylaconine 1) Properties and solubility Colorless 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.90 (1H, d, J = 4.8Hz) (βH at 14th) 1.14 (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).

165.2 (C of p-chlorobenzoyl group carbonyl) 131.1,128.8,128.1,139.6 (C of p-chlorobenzoyl group) 94.1,85.0,83.6,80.7,77.3,75.0,72.4,71.9 (16,6,1, 14,18,13,15,3 position C) 61.7,59.1,57.8,56.0 (16,18,6,1 position methoxy group C) 49.0 (N-ethyl methylene C) 13.3 (N-ethyl 6) Mass spectrometry m / z 621,623 (M ⁺ ) 7) Elemental analysis C ₃₂ H ₄₄ NO ₉ Cl, Calculated C: 61.78, H: 7.13, N: 2.25 Found C: 61.93, H : 7.30, N: 2.11 (28) Physical properties and analytical data of 8-deoxy-14-O-m-chlorobenzoyl aconine 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

8.02-7.35 (4H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 5.1Hz) (βH at position 14) 1.11 (3H, t, J = 7.0 Hz) (N-ethyl methine 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, 127.8 (C of m-chlorobenzoyl group) 94.1, 85.1, 83.6, 80.9, 77.3, 75.0, 72.4, 71.9 (16, 6, 1,
14,18,13,15,3 position C) 61.5,59.1,57.8,56.1 (C of methoxy group at 16,18,6,1 position) 49.0 (C of N-ethyl methylene) 13.3 (N-ethyl the C-methyl) 6) mass spectroscopy ^{m / z 621,623 (M +)} 7) elemental analysis C ₃₂ H ₄₄ NO ₉ Cl, calculated C: 61.78, H: 7.13, N: 2.25 Found C: 61.75, H : 7.23, N: 2.16 (29) 8-deoxy-14-O-α-methyl- (4- (α
-Methylsetic acid) -Phenyl) acetylaconine physical properties and analytical data 1) Properties and solubility Soluble, insoluble in hexane and water.

2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 1715 cmcm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 = 4.7Hz) (βH at position 14) 3.63 (2H, q, J = 7.0 Hz) (α-methylacetyl and α
-H of methyl methine methine) 1.42 (6H, d, J = 7.0 Hz) (α-methylacetyl and α
-H of methyl methyl acid acid) 1.11 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ , ppm).

180.5 (C of carboxyl) 176.0 (C of carbonyl) 140.4, 139.3, 128.2, 127.0 (C of benzene ring) 60.4, 60.2 (C of methine of α-methylacetyl and α-methylacetylic acid) 18.2, 18.1 (α C) 94.5,85.0,83.7,80.4,77.5,75.3,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 61.9,59.2,58.0,56.1 (C of 16,18,6,1 position methoxy group) 49.0 (N-ethyl methylene C) 13.2 (N-ethyl 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: 64.68, H: 7.76, N: 2.18 (30) Physical properties and analytical data of 8-deoxy-14-O-methylaconine 1) Properties and solubility A colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, Soluble in pyridine and dimethylsulfoxide, insoluble in hexane and water.

2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cmcm ^-1 .

3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

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).

93.4,84.7,83.5,81.3,77.5,77.2,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 60.6,59.2,58.3,58.1,56.0 (16,18,6,1,14 position methoxy group C) 49.4 (N-ethyl methylene C) 14.1 (C of N-ethyl methyl) 5) Mass spectrometry m / z 497 (M ⁺ ) 6) Elemental analysis C ₂₆ H ₄₃ NO ₈ , Calculated C: 62.75, H: 8.71, N: 2.81 Found C: 62.55, H: 8.86, N: 2.65 (31) Physical properties and analytical data of 8-deoxy-14-O-benzylaconine 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 3300 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.28 (5H, m) (H of benzyl group) 4.48 (2H, s) (H of benzyl group of methylene) 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 of methylene) 93.6,84.5,83.1,81.2,77.4,77.3,72.4,72.1 (16,6,1,
14,18,13,15,3 position C) 60.3,59.1,58.1,56.0 (C of 16,18,6,1 position methoxy group) 49.5 (N-ethyl methylene C) 14.0 (N-ethyl 6) Mass spectrometry m / z 573 (M ⁺ ) 7) Elemental analysis C ₃₂ H ₄₇ NO ₈ , Calculated C: 66.99, H: 8.26, N: 2.44 Found C: 67.12, H: 8.37, N: 2.45 (32) Physical property value and analytical data of 8-deoxy-14-O-crotyl aconin 1) Property and solubility Colorless non-crystalline powder, ether, chloroform, benzene, ethanol, methanol, ethyl acetate, Soluble in pyridine and dimethylsulfoxide, insoluble in hexane and water.

2) Infrared absorption spectrum (KBr) analysis The absorption maximum is shown at 3300 cm ^-1 .

3) ¹³ 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) 1.70 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 1.12 (3H, t, J = 7.3 Hz) (H of methyl of N-ethyl) 4) ¹ 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) 93.4,84.6,83.5,81.2,77.5,77.2,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 60.5,59.1,58.0,55.5 (C of 16,18,6,1 position methoxy group) 49.5 (N-ethyl methylene C) 13.9 (N-ethyl C) 12.7 (C of methyl group of crotyl group) 5) Mass spectrum analysis m / z 537 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₈ , Calculated values C: 64.78, H: 8.81 N : 2.60 found C: 65.01, H: 8.93, N: 2.47 (33) Physical properties and analytical data of 8-deoxy-14-OO-chlorobenzoyl aconine 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

8.00-7.45 (4H, m) (H of o-chlorobenzoyl group) 4.91 (1H, d, J = 4.8 Hz) (βH at position 14) 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 o-chlorobenzoyl group carbonyl) 129.9,136.0,128.7,133.8 126,3 (C of o-chlorobenzoyl group) 94.1,85.0,83.5,80.8,77.3,75.1,72.5,72.0 (16,6 , 1,14,18,13,15,3 position C) 61.7,59.1,57.9,56.0 (C of 16,18,6,1 position methoxy group) 49.0 (N-ethyl methylene C) 13.5 ( of methyl N- ethyl C) 6) mass spectroscopy ^{m / z 621,623 (M +)} 7) elemental analysis C ₃₂ H ₄₄ NO ₉ Cl, calculated C: 61.78, H: 7.13, N: 2.25 Found C: 61.86, H: 7.40, N: 2.18 (34) Physical properties and analytical data of 8-deoxy-14-O-m-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 1715 cmcm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.64-7.26 (4H, m) (H of m-anisoyl group) 4.92 (1H, d, J = 4.6 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of m-anisoyl group) 1.18 (3H, t, J = 7.0Hz) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

165.0 (C of m-anisoyl group) 131.2, 121.4, 129.5, 118.3, 158.9, 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,
14,18,13,15,3 position C) 55.4, (m-anisoyl group methoxy group C) 61.6,59.1,58.0,56.1, (16,18,6,1 position methoxy group C) 49.1 (C of N-ethyl methylene) 13.5 (C of N-ethyl methyl) 6) Mass spectrometry m / z 617 (M ⁺ ) 7) Elemental analysis C ₃₃ H ₄₇ NO ₁₀ , Calculated C: 64.16, H : 7.67, N: 2.27 Found C: 64.19, H: 7.62, N: 2.20 (35) Physical properties and analytical data of 8-deoxy-14-O-acetylaconin 1) Properties and solubility Colorless prism crystals It has a melting point of 105 to 107 °, 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 1713 cm ^-1 .

3) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 4.97 (1 H, d, J = 5.04 Hz) (βH at position 14) 2.05 (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 171.4 (acetyl group) 94.3,85.1,83.7,80.2,76.6,75.3,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 61.6,59.0,57.9,56.0 (16,18,6,1 position methoxy C) 49.1 (N-ethyl methylene C) 13.5 (N-ethyl 5) Mass spectrometry m / z 525 (M ⁺ ) 6) Elemental analysis C ₂₇ H ₄₃ NO ₉ , Calculated C: 61.70, H: 8.25, N: 2.66 Found: C: 61.56, H: 8.31, N: 2.54 (36) Physical properties and analytical data of 8-deoxy-14-O- (4-methyl) pentylaconin 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) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 1.10 (3H, t, J = 7.0Hz) (H of methyl of N-ethyl) 1.02 (6H, d, J = 7.0Hz) (H of methyl of 4-methylpentyl group) 3) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 93.4,84.6,83.3,81.0,77.4,77.2,72.4,71.9 (16,6,1,1
14,18,13,15,3 position C) 60.5,59.1,58.0,55.5 (C of 16,18,6,1 position methoxy group) 49.3 (N-ethyl methylene C) 13.9 (N-ethyl C) 21,3 (Methyl C of 4-methylpentyl) 4) Mass spectrum analysis 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 (37) Physical properties and analytical data of N-desethyl-8-deoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline It is soluble powder 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.95 (1H, d, J = 5.0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl 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) 163.5,131.8,113.7,122.1 (C of anisoyl group) 94.3,85.2,83.7,80.2,77.4,75.1,72.4,72.0 (16,6,1,14,18,13, C at 15,3 position) 61.9,59.0,57.9,56.1 (C derived from methoxy group bonded at 16,18,6,1 position) 55.4 (C of methoxy group of anisoyl group) 6) Mass spectrum analysis m / z 589 (M ⁺ ) 7) Elemental analysis C ₃₁ H ₄₃ NO ₁₀ , Calculated C: 63.14, H: 7.35, N: 2.38 Found C: 63.39, H: 7.33, N: 2.02 (38) N-desethyl-N -Amyl-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 1715 cmcm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.95 (1H, d, J = 5.0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (H of N-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 carbonyl) 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,
14,18,13,15,3 position C) 61.8,59.1,57.8,56.0 (C derived from methoxy group bonded to 16,18,6,1 position) 55.4 (methoxy C of anisoyl group) 13.1 (N - C methyl amyl) 6) mass spectroscopy ^{m / z 659 (M +)} 7) elemental analysis C ₃₆ H ₅₃ NO _10, calculated value C: 65.53, H: 8.10, N: 2.12 Found C: 65.81, H: 8.09, N: 2.18 (39) N-desethyl-N-propyl-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 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.93 (1H, d, J = 5.0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 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).

165.9 (C of anisoyl group carbonyl) 163.6,131.8,122.2,113.7 (C of anisoyl group) 94.3,85.3,83.7,80.2,77.5,75.0,72.3,71.9 (16,6,1,14,18,13, (C at 15,3 position) 61.8,59.1,57.8,56.1 (C derived from methoxy group attached at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 13.1 (C of N-propyl methyl 6) Mass spectrum analysis m / z 631 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₉ NO ₁₀ , Calculated C: 64.64, H: 7.82, N: 2.22 Observed C: 64.85, H: 7.66, N: 2.01 (40) N-desethyl-N- (4-methyl) pentyl-
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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.94 (1H, d, J = 5.0) (βH at position 14) 3.88 (3H, s) (H of methoxy group of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (H of methyl of N- (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) 163.6,131.7,113.4,122.1 (C of anisoyl group) 94.5,85.3,83.5,80.0,77.6,75.0,72.5,71.9 (16,6,1,14,18,13, (C at 15,3 position) 61.8,59.1,57.8,56.0 (C derived from methoxy group bonded to 16,18,6,1 position) 55.4 (C of methoxy of anisoyl group) 21.5 (N- (4-methyl) 6) Mass spectrometry 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 (41) N-desethyl-N-acetyl-8-deoxy-
Physical properties and analytical data of 14-O-anisoylaconine 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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.93 (1H, d, J = 5.0) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 2.34 (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).

170.8 (C of N-acetyl carbonyl) 165.9 (C 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 (16,6,1
4,1.8,5,13,15,3 position C) 61.8,59.1,57.9,56.1 (C derived from methoxy group bonded to 16,18,6,1 position) 55.4 (methoxy C of anisoyl group) 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 Observed C : 62.62, H: 7.10, N: 2.18 (42) Physical properties and analytical data of N-desethyl-N-benzoyl-8-deoxy-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 1711,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 4.95 (1H, d, J = 5.0) (βH at position 14) 3.87 (3H, s) (H of methoxy group 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 N-carbonyl 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) 94.4, 83.7, 80.1, 79.8, 77.5, 75.1 , 72,4,71.9 (C at position 16,6,14,1,18,13,15,3) 61.8,59.1,57.8,56.0 (C derived from methoxy group bonded to position 16,18,6,1) 5) (C of anisoyl group methoxy) 6) Mass spectrum analysis m / z 693 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₇ NO ₁₁ , Calculated C: 65.79, H: 6.83, N: 2.02 Observed C : 65.91, H: 6.79, N: 2.15 (43) Physical properties and analytical data of 16-epi-8-deoxy-14-O-trimethylgalloylaconin 1) Properties and solubility 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) 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 = 4.7Hz)) (βH at position 14) 3.88 (9H, s) (methoxy H of trimethylgalloyl group) 1.12 (3H, t, J = 7.0Hz) (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 carbonyl) 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,
14,18,13,15,3-position C) 55.9 (trimethylgalloyl-group methoxy-group C) 61.9,59.3,58.0,56.1 (16,18,6,1-position methoxy-C) 49.0 (N- Methylene C of ethyl group 13.5 (methyl C of N-ethyl group) 5) mass spectrometry m / z 677 (M ⁺ ) (44) 16-epi-8-deoxy-14-O-veratroyl aconine 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 = 4.6Hz) (βH at position 14) 3.92 (6H, s) (methoxy H of veratroyl group) 1.12 (3H, t, J = 7.0Hz) (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 veratroyl group carbonyl) 122.5, 110.5, 153.1, 148.1, 112.3 (C of veratroyl group) 91.2, 85.0, 83.7, 80.4, 77.4, 75.3, 72.4, 72.0 (16, 6, 1, 1)
14,18,13,15,3 position C) 55.8, (C of methoxy group of veratroyl group) 61.8,59.1,57.9,56.0, (C of methoxy group of 16,18,6,1 position) 49.1 (N 13.4 (N-ethyl methyl C) 6) Mass spectrometry m / z 647 (M ⁺ ) (45) 16-epi-8-deoxy-14-Op-chloro 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 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.10 (1H, d, J = 4.8Hz) (14th place βH) 1.11 (3H, t, J = 7.0Hz) (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 p-chlorobenzoyl group carbonyl) 130.5, 130.7, 128.7, 139.6 (C of p-chlorobenzoyl group) 91.1, 84.8, 83.5, 80.7, 77.3, 75.2, 73.0, 72.1 (16, 6, 1, 1
14,18,13,15,3 position C) 62.2,59.2,58.0,56.0 (16,18,6,1 position methoxy group C) 49.2 (N-ethyl group methylene C) 13.3 (N- 6) Mass spectrum analysis m / z 621,623 (M ⁺ ) (46) Physical property values and analytical data of 16-epi-8-deoxy-14-O-m-chlorobenzoylaconine 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.98-7.30 (4H, m) (H of m-chlorobenzoyl group) 5.05 (1H, d, J = 4.7Hz) (βH at position 14) 1.12 (3H, t, J = 7.0Hz) (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 m-chlorobenzoyl group carbonyl) 131.6, 129.8, 129.5, 135.0, 128.4 (C of m-chlorobenzoyl group) 91.4, 84.9, 83.4, 80.6, 77.2, 75.3, 73.0, 72.1 (16, 6, 1,
14,18,13,15,3 position C) 62.2,59.2,58.1,56.0 (C of 16,18,6,1 position methoxy group) 49.1 (N-ethyl group methylene C) 13.3 (N- C) 6) Mass spectrum analysis m / z 621,623 (M ⁺ ) (47) 16-epi-8-deoxy-14-O-α-methyl-
Physical property value and analytical data of (4- (α-methylacetylic acid) phenyl) acetylaconine 1) Property 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.30 (4H, m) (H of phenyl group) 4.91 (1H, d, J = 4.7Hz)) (βH at position 14) 3.63 (2H, q, J = 7.0 Hz) (propionyl group methine H 1.42 (6H, d, J = 7.0 Hz) (propionyl group methyl H) 1.11 (3H, t, J = 7.0 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).

180.5 (C of propionyl group carboxyl) 166.0 (C of propionyl group carbonyl) 140.4,139.3,128.2,127.0 (C of phenyl group) 60.4,60.2 (C of propionyl group methine) 18.2, 18.1 (Methyl of propionyl group) C) 90.5,85.0,83.7,80.4,77.5,75.3,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 61.9,59.2,58.0,56.1 (C of 16,18,6,1 position methoxy group) 49.0 (C of N-ethyl group methylene) 13.2 (N- 6) Mass spectrometry m / z 687 (M ⁺ ) (48) Physical properties and analytical data of 16-epi-8-deoxy-14-O-methylaconine 1) Properties and solubility Colorless Amorphous 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 3300 cm ^-1 .

3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

1.10 (3H, t, J = 7.0Hz) (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 (16,6,1,
14,18,13,15,3 position C) 60.6,59.2,58.3,58.1,56.0 (16,18,14,6,1 position methoxy group C) 49.4 (N-ethyl group methylene C) 14.1 (C of N-ethyl group methyl) 5) Mass spectrometry m / z 497 (M ⁺ ) (49) Physical property values and analytical data of 16-epi-8-deoxy-14-O-benzylaconine 1) Description 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) UV absorption spectrum (ethanol) analysis 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) 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).

126.5, 127.0, 128.3, 141.5 (C of benzyl group) 64.1 (C of benzyl group of methylene) 90.5, 84.5, 83.1, 81.2, 77.4, 77.3, 72.4, 72.1 (16, 6, 1, 14, 18, 13, 13 (C at 15,3 position) 60.3,59.1,58.1,56.0 (C of methoxy group at 16,18,6,1 position) 49.4 (C of N-ethyl group methylene) 14.0 (C of N-ethyl group methyl) 6) Mass spectrum analysis m / z 573 (M ⁺ ) (50) Physical property values and analytical data of 16-epi-8-deoxy-14-O-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) Ultraviolet absorption spectrum (ethanol) analysis 4) 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) 1.70 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 0.88 (3H, t, J = 7.3 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).

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 (C at 16,6,1,14,18,13,15,3 position) 60.5, 59.1,58.0,55.5 (C of methoxy group at 16,18,6,1 position) 49.5 (C of N-ethyl group of methylene) 13.9 (C of N-ethyl group of methyl) 12.7 (Methyl group of crotyl group) C) 6) Mass spectrum analysis m / z 537 (M ⁺ ) (51) Physical properties and analytical data of 16-epi-8-deoxy-14-OO-chlorobenzoyl aconine 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

8.00-7.45 (4H, m) (H of o-chlorobenzoyl group) 5.02 (1H, d, J = 4.8Hz) (βH at position 14) 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 o-chlorobenzoyl group carbonyl) 129.9, 136.0, 128.7, 133.8, 126.3 (C of o-chlorobenzoyl group) 90.3, 84.9, 83.5, 80.4, 77.3, 75.1, 72.6, 72.0 (16, 6, 1,
14,18,13,15,3 position C) 61.8,59.1,57.9,56.0 (C of 16,18,6,1 position methoxy group) 49.0 (N-ethyl group methylene C) 13.5 (N- 6) Mass spectrometry m / z 621,623 (M ⁺ ) (52) Physical properties and analytical data of 16-epi-8-deoxy-14-O-m-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.64-7.26 (4H, m) (H of m-anisoyl group) 4.92 (1H, d, J = 4.6Hz) (βH at position 14) 3.91 (3H, s) (H of m-anisoyl group) 1.18 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The signal is shown (δ, ppm).

165.0 (C of m-anisoyl group) 131.2, 121.4, 129.5, 118.3, 158.9, 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,
14,18,13,15,3 position C) 55.4 (m-anisoyl group methoxy C) 61.6,59.1,58.0,56. (16,18,6,1 position methoxy group C) 49.1 (N -Methylene C of ethyl group) 13.5 (methyl C of N-ethyl group) 6) mass spectrometry m / z 617 (M ⁺ ) (53) 16-epi-N-desethyl-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.15 (1H, d, J = 5.0Hz) (14th place βH) 3.87 (3H, s) (H of methoxy of anisoyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

166.0 (C of anisoyl group) 163.5,131.8,113.7,122.1 (C of anisoyl group) 91.2,85.1,83.7,80.2,77.4,75.9,72.4,72.0 (16,6,1,
14,18,13,15,3 position C) 55.4 (methoxy of anisoyl group) 62.2,59.0,57.9,56.1 (C of 16,18,6,1 position methoxy) 6) Mass spectrum analysis m / z 589 (M ⁺ ) (54) Physical properties and analytical data of 16-epi-N-desethyl-N-amyl-8-deoxy-14-O-anisoylaconine 1) Properties and solubility Colorless amorphous It is soluble powder 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.14 (1H, d, J = 5.0Hz) (14th place βH) 3.87 (3H, s) (methoxy H of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (H of methyl N-amyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (Δ, ppm).

166.0 (C of anisoyl group carbonyl) 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, 72.5, 72.0 (1
6,6,1,14,18,13,15,3 position C) 55.4 (C of anisoyl group methoxy) 62.2,59.1,57.8,56.0 (C of 16,18,6,1 position methoxy group) 13.1 (C of N-amyl methyl) 6) Mass spectrometry m / z 659 (M ⁺ ) (55) 16-Epi-N-desethyl-N-propyl-8-
Physical property value and analytical data of deoxy-14-O-anisoylaconine 1) Property 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.12 (1H, d, J = 5.0Hz) (14th place βH) 3.87 (3H, s) (methoxy H of anisoyl group) 1.10 (3H, t, J = 7.0 Hz) (methyl H of N-propyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis Next signal (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,
(C at 14,18,13,15,3 position) 62.2,59.1,57.9,56. (16,18; C of methoxy group at 6,1 position) 13.0 (C of N-propyl methyl) 6) Mass spectrum Analysis m / z 631 (M ⁺ ) (56) 16-epi-N-desethyl-N- (4-methyl)
Physical properties and analytical data of pentyl-8-deoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.12 (1H, d, J = 5.0Hz) (14th place βH) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (methyl H of N- (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) 163.9,131.7,122.1,113.4 (C of anisoyl group) 91.3,85.2,83.5,80.0,77.6,76.0,72.5,71.9 (16,6,1,
14,18,13,15,3 position C) 55.4 (methoxy C of anisoyl group) 62.2,59.1,57.8,56.0 (C of 16,18,6,1 position methoxy) 21.5 (N- (4 C) 6) Mass spectrometry m / z 673 (M ⁺ ) (57) 16-epi-N-desethyl-N-acetyl-8-.
Physical property value and analytical data of deoxy-14-O-anisoylaconine 1) Property 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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.15 (1H, d, J = 5.0Hz)) (βH at 14th position) 3.87 (3H, s) (H of methoxy group of anisoyl group) 2.34 (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).

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 , 6,1
4,2.2,59.1,57.9,56.1 (C of the methoxy group at the 16,18,6,1 position) 55.4 (C of the methoxy group of the anisoyl group) 22.4 (N- Acetyl methyl C) 6) mass spectrometry m / z 631 (M ⁺ ) (58) 16-epi-N-desethyl-N-benzoyl-8
-Deoxy-14-O-anisoylaconine physical properties and analytical data 1) Properties and solubility 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 1711,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 5.14 (1H, d, J = 5.0Hz) (14th place βH) 3.87 (3H, s) (H of methoxy 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) 133.9,133.5,128.6,128.2,127.6 (C of benzoyl group) 91.3,83.7,80.1,79.9,77.5,76.0,72.4, 71.9 (16,6,1
4,1,18,13,15,3 position C) 62.2,59.1,57.8,56.0 (16,18,6,1 position methoxy C) 55.4 (anisoyl group methoxy C) 6) Mass spectrum analysis m / z 693 (M ⁺ ) (59) Physical properties and analytical data of 8-deoxy-14-Op-methoxybenzylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, 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 3300 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.45 (2H, s) (methylene H of p-methoxybenzyl group) 1.09 (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).

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, 1,
14,18,13,15,3 position C) 60.2,59.1,58.1,56.0 (16,18,6,1 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 spectrometry m / z 603 (M ⁺ ) 7) elemental analysis C ₃₃ H ₄₉ NO ₉ , calculated C: 65.65, H: 8.18, N: 2.32 Found C: 65.73, H: 8.29, N: 2.12 (60) 8-Deoxy-14-O-amyl aconine Physical Properties and Analytical Data 1) Properties and solubility A colorless non-crystalline powder, ether It is soluble in 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 3300 cm ^-1 .

3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

0.92 (3H, t J = 7.4 Hz) (H of N-ethyl methyl) 0.90 (3H, t, J = 7.1 Hz) (H of amyl methyl group) 4) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃₎ ) Analysis The following signals are shown (δ, ppm).

93.5,84.6,83.5,81.2,77.5,77.2,72.5,72.1 (16,6,1,
14,18,13,15,3 position C) 60.5,59.1,58.0,55.6 (C of 16,18,6,1 position methoxy group) 49.5 (N-ethyl methylene C) 14.0 (N-ethyl 5) Mass spectrometry m / z 553 (M ⁺ ) 6) Elemental analysis C ₃₀ H ₅₁ NO ₈ , Calculated C: 65.07, H: 9.28, N: 2.53 Found C: 64.99, H: 9.35, N: 2.49 (61) Physical properties and analytical data of 8-deoxy-14-O-m-bromobenzoylaconine 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 1723 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 8.18 to 7.34 (4H, m) (H of m-bromobenzoyl group) 5.00 (1H, d, J = 5.0 Hz) (βH at position 14) 1.13 (3H, t, J = 7.1 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-bromobenzoyl carbonyl) 136.4, 136.1, 132.0, 130.1, 128.3, 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 (16,18,6,1 position methoxy group C) 49.2 (N-ethyl methylene C) 13.3 (N-ethyl methyl of C) 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 Br, calculated C: 57.66, H: 6.65, N: 2.10 Found C: 57.48, H: 6.91, N: 2.00 (62) Physical properties and analytical data of 8-deoxy-14-O-m-fluorobenzoylaconine 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 1725 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) (βH at position 14) 1.26 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 164.4 (C of m-fluorobenzoyl carbonyl) 160.5,130.3,130.2, 125.6,120.5,116.7 (C of m-fluorobenzoyl) 93.9,84.9,83.7,80.6,77.2,75.0,72.0,71.8 (16,6,1,
14,18,13,15,3 position C) 59.2,58.1,57.7,56.2 (C of 16,18,6,1 position methoxy group) 49.4 (N-ethyl methylene C) 12.8 (N-ethyl of methyl C) 6) mass spectroscopy ^{m / z 605 (M +)} 7) elemental analysis C ₃₂ H ₄₄ NO ₉ F, calculated C: 63.46, H: 7.32, N: 2.31 Found C: 63.41, H : 7.29, N: 2.41 (63) Physical properties and analytical data of 3,8,13-trideoxy-14-O-veratroyl aconin 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform, 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) (H of methoxy group of veratroyl group) 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 veratroyl group carbonyl) 122.5,110.5,153.1,148.2,112.3 (C of veratroyl group) 93.0,86.0,85.1,81.9,78.4,72.4 (C at position 16,1,6,18,14,15) 55.8 (C of methoxy group of veratroyl group) 59.1,58.7,57.9,56.0 (C of methoxy group at 18,16,6,1 position) 49.0 (C of N-ethyl methylene) 13.4 (Methyl of N-ethyl C) 6) Mass spectrum analysis 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 (64) Physical property values and analytical data of 3,8,13-trideoxy-14-O-acetylaconin 1) Properties and solubility 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 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) 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 Next signal (Δ, ppm).

171.5 (C of the carbonyl of the acetyl group) 93.0, 86.0, 85.1, 81.7, 77.4, 72.4 (C at the 16,16,18,14,15 position) 59.2,58.8,57.7,56.1 (18,16,6, Methoxy group at position 1) 49.1 (N-ethyl methylene C) 13.4 (N-ethyl methyl C) 21.4 (acetyl methyl methyl) 5) Mass spectrometry m / z 493 (M ⁺ ) 7) elemental analysis C ₂₇ H ₄₃ NO _7, calculated C: 65.69, H: 8.78, N: 2.84 Found C: 65.81, H: 8.67, N: 2.63 65) 3,8,13- trideoxy -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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.78-7.30 (4H, m) (H of m-chlorobenzoyl group) 5.06 (1H, t, J = 4.7Hz) (βH at position 14) 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).

165.0 (C of m-chlorobenzoyl group) 131.6, 130.0, 129.5, 135.0, 128.4 (C of m-chlorobenzoyl group) 93.1, 86.0, 85.3, 82.0, 78.3, 72.5 (16, 1, 6, 18, (C at 14,15 position) 59.0,58.7,58.0,56. (C at 18,16,6,1 position methoxy) 49.2 (C at N-ethyl methylene) 13.1 (C at N-ethyl methyl group) 6) mass spectroscopy ^{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: 2.14 (66) Physical properties and analytical data of 3,8,13-trideoxy-14-O-benzylaconine 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 3450 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.09 (3H, t, J = 7.0Hz) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

126.3,127.3,128.0,141.8 (C of benzyl group) 64.3 (C of benzyl group methylene) 92.5,86.1,84.3,82.0,81.1,72.5 (C at 16,1,6,18,14,15 position) 59.2 , 58.0, 57.2, 56.0 (C of the methoxy group at the 16,6,18,1 position) 49.2 (C of N-ethyl methylene) 13.1 (C of N-ethyl methyl) 6) Mass spectrum analysis m / z 541 (M ⁺ ) 7) Elemental analysis C ₃₂ H ₄₇ NO ₆ , Calculated C: 70.95, H: 8.74, N: 2.59 Observed: C: 70.77, H: 8.84, N: 2.65 (67) 3,8,13− Trideoxy-14-O- (4-methyl)
Physical properties and analytical data of pentyl 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 It is.

2) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 1.10 (6H, t, J = 7.0Hz) (H of methyl of 4-methylpentyl) 3) ¹³ C nuclear 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 16,1,6,18,14,15) 59.2,58.7,57.9,56.0 (C of methoxy group at position 18,16,6,1) 49.0 (N-ethyl methylene C) 13.1 (N-ethyl methyl C) 21.2 (4-methylpentyl methyl C) 6) Mass spectrometry m / z 535 (M ⁺ ) 7) 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: 2.46 (68) Physical properties of 3,8,13-Trideoxy-14-O-crotylaconin and Analytical data 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 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 crotyl group methylene) 1.71 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 0.91 (3H, t, J = 7.3 Hz) (H of methyl of 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 crotyl group double bond) 92.3,86.2,84.6,81.5,81.3,72.5 (C at 16,1,6,18,14,15 position) 59.0,58.1,57.8,55.8 (18, C, 6,6-, 1-position methoxy group 49.4 (N-ethyl methylene C) 13.9, N-ethyl methyl C 12.6, crotyl methyl C 5) Mass spectrometry m / z 505 (M ⁺ ) 6) Elemental analysis C ₂₉ H ₄₇ NO ₆ , Calculated C: 68.88, H: 9.37, N: 2.77 Found C: 68.91, H: 9.36, N: 2.68 (69) 3,8− Physical properties and analytical data of dideoxy-14-O-veratroyl aconin 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 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) (H of methoxy group of veratroyl group) 3.53,3.32, 3.29,3.26 (each 3H, s) (H of methoxy group at 1,6,16 and 18) 1.11 (3H, t, J = 7.0Hz) (H of N-ethyl methyl) 5) ¹³ C nuclear magnetic field 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, 112.3 (C of veratroyl group) 94.1, 86.0, 85.1, 80.3, 81.9, 75.3, 72.4 (16, 1, 6, 14, 1
8,13,15-position C) 55.8 (veratoloyl group methoxy C) 61.8,59.0,58.0,56.0 (16,18,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.4 (C of N-ethyl methyl) 6) Mass spectrum analysis m / z 631 (M ⁺ ) 7) Elemental analysis C ₃₄ H ₄₉ NO ₁₀ , Calculated C: 64.64, H: 7.82, N: 2.22 Observed C : 64.83, H: 8.01, N: 2.08 (70) Physical property value and analytical data of 3,8-dideoxy-14-O-acetylaconine 1) Property and solubility A colorless amorphous powder, 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 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) 2.06 (H of acetyl 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, 1
4,13,15-position C) 61.6,59.0,57.9,56.0 (16,18,6,1-position methoxy group C) 49.0 (N-ethyl methylene C) 13.5 (N-ethyl methyl C 21.6 (C of acetyl methyl) 5) Mass spectrometry m / z 509 (M ⁺ ) 7) Elemental analysis C ₂₇ H ₄₃ NO ₈ , Calculated C: 63.63, H: 8.50, N: 2.75 Observed C : 63.39, H: 8.71, N: 2.54 (71) Physical properties and analytical data of 3,8-dideoxy-14-O-m-chlorobenzoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether It is soluble in 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.98-7.30 (4H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 4.7 Hz) (βH at position 14) 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) 131.5,129.9,129.5,135.0,128.4 (C of m-chlorobenzoyl group) 94.4,86.2,85.0,82.5,80.3,75.3,72.6 (16,1,6, 18,1
C, 4,13,15) 61.8,59.1,58.1,56.0 (C of methoxy group at 16,18,6,1) 49.1 (C of N-ethyl methylene) 13.2 (C of N-ethyl methyl ) 6) mass spectroscopy ^{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 (72) Physical property value and analytical data of 3,8-dideoxy-14-O-benzylaconine 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 3300 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 benzyl group of methylene) 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).

126.3, 127.2, 128.3, 141.6 (benzyl group C) 64.2 (benzyl group methylene C) 93.5, 86.1, 84.3, 81.9, 81.1, 77.3, 72.4 (16, 1, 6, 18, 1
4,13,15 position C) 60.2,59.1,58.0,56.0 (16,18,6,1 position methoxy group C) 49.2 (N-ethyl methylene C) 13.0 (N-ethyl methyl C ) 6) mass spectroscopy ^{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 (73) Physical property values and analytical data of 3,8-dideoxy-14-O- (4-methyl) pentylaconin 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) ¹ H nuclear magnetic resonance spectrum (CDCl ₃ ) analysis 1.10 (3H, t, J = 7.0 Hz) (H of methyl of N-ethyl) 1.02 (6H, d, J = 7.0 Hz) (H of methyl of 4-methylpentyl) 3) ¹³ C nuclear magnetic resonance spectrum ( CDCl ₃ ) analysis shows the following signals (δ, ppm):

93.4,85.3,83.2,80.3,77.4,75.5,72,4 (16,1,6,18,1
(C at 4,13,15) 60.3,59.0,58.2,56. (C at methoxy group at 16,18,6,1) 49.3 (C at N-ethyl methylene) 13.8 (C at N-ethyl methylene) C) 21.2 (4-methylpentyl methyl C) 4) mass spectroscopy ^{m / z 551 (M +)} 5) elemental analysis C ₃₁ H ₅₃ NO _7, calculated C: 67.48, H: 9.68, N: 2.54 Found: C: 67.21, H: 9.76, N: 2.22 (74) Physical properties and analytical data of 3,8-dideoxy-14-O-crotyl aconin 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform 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 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 double bond of crotyl group) 4.09 (2H, m) (H of methylene of crotyl group) 1.70 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 0.89 (3H, t, J = 7.3 Hz) (H of methyl of N-ethyl) 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) 93.5,86.2,84,6,81,6,81.3,77.2,72.4 (16,1,6,18,1
4,13,15 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 (16,18 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 C: 66.91, H: 9.21, N: 2.55 (75) Physical properties and analytical data of 16-epi-8-deoxy-14-O- (p-methoxy) benzylaconine 1) Properties and solubility Colorless non-crystal It is soluble powder 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) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

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 = 7.0Hz) (H of methyl of N-ethyl) 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 benzyl group) 64.0 (C of benzyl group of methylene) 90.3,84.4,83.2,81.0,77.4,77.2,72.3,72.0 (16,6,1,
14,18,13,15,3 position C) 60.2,59.1,58.1,56.0 (16,18,6,1 position methoxy group C) 55.8 (p-methoxybenzyl group methoxy C) 49.4 (N -Methyl C of ethyl group) 14.0 (C of N-ethyl methyl) 6) Mass spectrum analysis m / z 603 (M ⁺ ) (76) Physical properties of 16-epi-8-deoxy-14-O-amyl aconin Value and analytical data 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 3300 cm ^-1 .

3) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

0.92 (3H, t, J = 7.4 Hz) (H of methyl of N-ethyl group) 0.90 (3H, t, J = 7.1 Hz) (H of methyl of 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 (16,6,1,
14,18,13,15,3 position C) 60.5,59.1,58.0,55.6 (16,18,6,1 position methoxy group C) 49.4 (N-ethyl group methylene C) 14.0 (N- Ethyl methyl methyl C) 13.5 (amyl methyl methyl C) 5) Mass spectrometry m / z 553 (M ⁺ ) (77) 16-epi-3,8,13-trideoxy-14-O-vera Physical properties and analytical data of Troylaconin 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 = 4.6Hz) (βH at position 14) 3.92 (6H, s) (methoxy H of veratroyl group) 1.10 (3H, t, J = 7.0Hz) (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 veratroyl group carbonyl) 122.5,110.5,153.1,148.2,112.3 (C of veratroyl group) 90.2,86.0,85.1,81.9,78.4,72.4 (C at position 16,1,6,18,14,15) 55.8 (C of methoxy group of veratroyl group) 59.1,58.7,57.9,56.0 (C of methoxy group at 18,16,6,1 position) 49.0 (C of N-ethyl group of methylene) 13.4 (N-ethyl group of methylene group) 6) Mass spectrum analysis m / z 615 (M ⁺ ) (78) 16-epi-3,8,13-trideoxy-14-O-m-
Physical properties 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, 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.98-7.30 (4H, m) (H of m-chlorobenzoyl group) 5.06 (1H, t, J = 4.7Hz) (βH at position 14) 1.12 (3H, t, J = 7.0Hz) (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 m-chlorobenzoyl group) 131.6, 130.0, 129.5, 135.0, 128.4 (C of m-chlorobenzoyl group) 90.1, 86.0, 85.3, 82.0, 78.3, 72.5 (16, 1, 6, 18, C at 14,15 position) 59.0,58.7,58.0,56.0 (C of methoxy group at 18,16,6,1 position) 49.2 (C of N-ethyl group methylene) 13.1 (C of N-ethyl group methyl) 6) Mass spectrum analysis m / z 589,591 (M ⁺ ) (79) Physical properties and analytical data of 16-epi-3,8,13-trideoxy-14-O-benzylaconine 1) Properties and solubility Colorless Amorphous 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 3450 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 1.09 (3H, t, J = 7.0Hz) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (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 (16,1,6,18,14,15 position C) 59.2 , 58.0, 57.2, 56.0 (C of methoxy group at 18,6,16,1 position) 49.2 (C of N-ethyl group of methylene) 13.1 (C of N-ethyl group of methyl) 6) Mass spectrum analysis m / z 541 (M ⁺ ) (80) Physical property values and analytical data of 16-epi-3,8,13-trideoxy-14-O-crotyl aconin 1) Properties and solubility A colorless amorphous 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 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 crotyl group methylene) 1.71 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 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 crotyl group double bond) 90.1,86.2,84.6,81.5,81.3,72.5 (C at 16,1,6,18,14,15 position) 59.0,58.1,57.8,55.8 (18, C, 6,6-, 1-position methoxy group 49.4 (N-ethyl group, methylene group C) 13.9 (N-ethyl group, methyl group C) 12.6 (crotyl group, methyl group C) 5) Mass spectrometry m / z 505 (M ⁺ ) (81) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-veratroyl aconin 1) Properties and solubility Colorless amorphous powder, ether It is soluble in 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 1720 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 = 4.6Hz) (βH at position 14) 3.92 (6H, s) (methoxy H of veratroyl group) 1.11 (3H, t, J = 7.0Hz) (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 veratroyl group carbonyl) 122.6, 110.5, 153.1, 148.1, 112.3 (C of veratroyl group) 90.1, 86.0, 85.1, 80.3, 81.9, 75.3, 72.4 (16, 1, 6, 14, 1
C at 8,13,15 position) 55.8 (C of methoxy group of veratroyl group) 61.8,59.0,
58.0, 56.0 (C of methoxy group at 16, 18, 6, 1 position) 49.0 (C of N-ethyl group of methylene) 13.4 (C of N-ethyl group of methyl) 6) Mass spectrum analysis m / z 631 ( M ⁺ ) (82) 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

7.98-7.30 (4H, m) (H of m-chlorobenzoyl group) 4.90 (1H, d, J = 4.7 Hz) (βH at position 14) 1.11 (3H, t, J = 7.0Hz) (H of methyl of N-ethyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

165.1 (C of m-chlorobenzoyl group carbonyl) 131.5,129.9,129.5,135.0,128.4 (C of m-chlorobenzoyl group) 90.4,86.2,85.0,82.5,80.3,75.3,72.6 (16,1,6, 18,1
C, 4,13,15 position) 61.8,59.1,58.1,56.0 (C of 16,18,6,1 position methoxy group) 49.1 (C of N-ethyl group methylene) 13.2 (Methyl of N-ethyl group) C) 6) Mass spectrum analysis m / z 605,607 (M ⁺ ) (83) Physical properties and analytical data of 16-epi-3,8-dideoxy-14-O-benzylaconine 1) Properties and solubility Colorless Amorphous 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 3300 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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 benzyl group of methylene) 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) 90.0,86.1,84.3,81.9,81.1,77.3,72.4 (16,1,6,18,1
4,13,15-position C) 60.2,59.1,58.0,56.0 (16,18,6,1-position methoxy group C) 49.2 (N-ethyl group methylene C) 13.0 (N-ethyl group methyl) C) 6) Mass spectrum analysis m / z 557 (M ⁺ ) (84) Physical property values and analysis data of 16-epi-3,8-dideoxy-14-O-crotyl aconin 1) Properties and solubility Colorless amorphous It is soluble powder 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 double bond of crotyl group) 4.09 (2H, m) (H of methylene of crotyl group) 1.70 (3H, d, J = 6.3 Hz) (H of methyl of crotyl group) 0.89 (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) 90.2,86.2,84.6,81.6,81.3,77.2,72.4 (16,1,6,18,1
49.5 (C of N-ethyl group methylene) 14.0 (N-ethyl group methyl C) 12.7 (crotyl group methyl group) 60.5, 59.0, 58.1, 55.8 (16 5) Mass spectral analysis m / z 521 (M ⁺ ) (85) Physical properties of N-desethyl-3,8-dideoxy-14-O-anisoylaconine And analytical data 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.95 (1H, d, J = 5.0Hz)) (14th place βH) 3.87 (3H, s) (H of methoxy of anisoyl 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) 163.8,131.4,113.5,122.2 (C of anisoyl group) 94.4,86.2,85.0,82.5,80.1,75.0,72.3, (16,1,6,18,1
4,13,15 position C) 61.9,59.1,58.0,56.0 (16,18,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 6) Mass spectrum analysis m / z 573 ( M ⁺ ) 7) Elemental analysis C ₃₁ H ₄₃ NO ₉ , Calculated C: 64.90, H: 7.55, N: 2.44 Observed C: 64.85, H: 7.41, N: 2.22 (86) N-desethyl-N-amyl Physical property values and analytical data of -3,8-dideoxy-14-O-anisoylaconine 1) Properties and solubility A colorless non-crystalline powder, 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 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.96 (1H, d, J = 5.0Hz) (βH at position 14) 3.87 (3H, s) (methoxyH of anisoyl group) 0.99 (3H, t, J = 7.0 Hz) (H of methyl of N-amyl 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) 163.8,131.8,113.6,122.1 (C of anisoyl group) 94.2,86.0,85.1,82.3,80.2,75.1,72.4 (16,1,6,18,14,13,15 position C) 55.4 (C of the methoxy group of the anisoyl group) 61.8, 59.1, 57.8, 56.0, (C of the methoxy group at the 16,18,6,1-position) 13.1 (C of the methyl of the N-amyl group) 6) Mass Spectral analysis m / z 643 (M ⁺ ) (87) Physical property values and analytical data of N-desethyl-N-propyl-3,8-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.94 (1H, d, J = 5.0Hz)) (14th place βH) 3.87 (3H, s) (methoxy H of anisoyl group) 1.10 (3H, t, J = 7.0 Hz) (methyl H of propyl group) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis (Δ, ppm).

165.9 (C of carboxyl of anisoyl group) 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 (16,1,6,18,14,13,15 position C) 61.8,59.0,58.0,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 13.0 (C of N-propyl methyl) 6) Mass spectrum analysis 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: 66.45, H: 7.98, N: 2.20 (88) N-desethyl -N- (4-methylpentyl)-
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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.94 (1H, d, J = 5.0Hz) (βH at position 14) 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 anisoyl group of carbonyl) 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 (16,1,6,18,14,13,15 position C) 61.8,59.0,57.9,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 21.5 (Methyl C of N- (4-methylpentyl)) ) 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: 2.26 ( 89) Physical properties and analytical data of N-desethyl-N-acetyl-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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.95 (1H, d, J = 5.0Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 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 acetyl group carbonyl) 166.0 (C of anisoyl group carbonyl) 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 , 1,14,13,15-position C) 61.9,59.1,58.0,56.0 (16,18,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N acetyl group methyl C) 6) Mass spectrum analysis m / z 615 (M ⁺ ) 7) Elemental analysis C ₃₃ H ₄₅ NO ₁₀ , Calculated C: 64.37, H: 7.37, N: 2.27 Found C: 64.52, H: 7.16, N: 2.25 (90) Physical properties and analytical data of N-desethyl-N-benzoyl-3,8-dideoxy-14-O-anisoylaconine 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 1710,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 4.93 (1H, d, J = 5.0Hz) (βH at position 14) 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).

165.8,166.0 (C of carbonyl) 163.8,131.7,113.6,122.0 (C of anisoyl group) 133.9,133.4,128.6,128.2,127. (C of benzoyl group) 94.3,85.0,82.4,82.0,80.3,75.0,72.5 (C at position 16,6,18,1,14,13,15) 61.8,59.1,57.8,56.0 (C at methoxy group at 16,18,6,1 position) 55.4 (Methoxy C at anisoyl group) 6 ) Mass spectrum analysis m / z 677 (M ⁺ ) 7) Elemental analysis C ₃₈ H ₄₇ NO ₁₀ , Calculated C: 67.34, H: 6.99, N: 2.07 Found C: 67.46, H: 7.08, N: 2.01 ( 91) N-desethyl-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.08 (1H, t, J = 4.8Hz) (βH at position 14) 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 (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 of 16,1,6,18,14,15 position) 59.1,58.7, 57.9,56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 6) Mass spectrum analysis m / z 557 (M ⁺ ) 7) Elemental analysis C ₃₁ H ₄₃ NO ₈ , Calculated C: 66.77, H: 7.77, N: 2.51 Found C: 66.70, H: 7.64, N: 2.48 (92) N-desethyl-N-amyl-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, 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.09 (1H, t, J = 4.8Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (H of N-amyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (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 of 16,1,6,18,14,15 position) 59.2,58.8, 57.9,56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 13.2 (C of N-amyl methyl) 6) Mass spectrum analysis m / z 627 (M ⁺ ) 7) Elemental analysis: C ₃₆ H ₅₃ NO ₈ , Calculated: C: 68.87, H: 8.51, N: 2.23 Found: C: 68.92, H: 8.50, N: 2.18 (93) N-desethyl-N-propyl-3, Physical properties and analytical data of 8,13-trideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.06 (1H, t, J = 4.8Hz) (14th place βH) 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 of the 16,1,6,18,14,15 position) 59.2,58.8, 57.9,56.0 (C of the methoxy group at the 18,16,6,1 position) 55.4 (C of the methoxy of anisoyl group) 13.0 (C of the methyl of N-propyl) 6) Mass spectrometry m / z 599 (M ⁺ ) 7) Elemental analysis: C ₃₄ H ₄₉ NO ₈ , calculated: C: 68.09, H: 8.23, N: 2.34, found: C: 68.17, H: 8.35, N: 2.30. (94) N-desethyl-N- (4-methyl) ) Pentyl-
Physical property values and analytical data of 3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility 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 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.10 (1H, t, J = 4.8Hz)) (βH at 14th) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (methyl H of N-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) 163.8,131.7,113.4,122.0 (C of anisoyl group) 94.3,86.1,85.0,82.2,80.1,72.5 (C at position 16,16,18,14,15) 59.3 , 58.8, 57.9, 56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 21.5 (C of methyl of N-4-methylpentyl) 6) Mass spectrum analysis m / z 641 (M ⁺ ) 7) Elemental analysis C ₃₇ H ₅₅ NO ₈ , Calculated C: 69.24, H: 8.64, N: 2.18 Found C: 69.46, H: 8.53, N: 2.09 (95) N-desethyl- Physical property value and analytical data of N-acetyl-3,8,13-trideoxy-14-O-anisoylaconine 1) Property and solubility A colorless non-crystalline powder, which is 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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.08 (1H, t, J = 4.8Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 2.30 (3H, s) (H of N-acetyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

170.9 (C of acetyl group carbonyl) 166.0 (C of anisoyl group carbonyl) 163.7,131.6,113.4,122.2 (C of anisoyl group) 94.5,84.9,82.5,81.9,80.2,72.4 (16,6,18,1 , 14,15 position C) 59.1,58.7,57.9,56.0 (18,16,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N-acetyl methyl C) 6 ) Mass spectrum analysis m / z 599 (M ⁺ ) 7) Elemental analysis C ₃₃ H ₄₅ NO ₉ , Calculated C: 66.09, H: 7.56, N: 2.34 Observed C: 65.87, H: 7.43, N: 2.28 ( 96) Physical properties and analytical data of N-desethyl-N-benzoyl-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 1710,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 5.06 (1H, t, J = 4.8Hz) (βH at position 14) 3.88 (3H, s) (methoxyH 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 (C of benzoyl group) 94.2,85.0,82.4,81.8,80.3,72.6 (16,6, 18,1,14,15th C) 59.2,58.8,57.9,56.0 (1
C) 8,5.4,61 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 C: 68.97 , H: 7.16, N: 2.12 Found C: 69.11, H: 7.02, N: 2.31 (97) N-desethyl-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.14 (1H, d, J = 5.0 Hz) (βH at position 14) 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 (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 (16,1,6,18,14,13,15 position C) 62.2,59.1,58.0,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (C of anisoyl group methoxy) 6) Mass spectrum analysis m / z 573 (M ⁺ ) (98) N-desethyl-N-amyl-16-epi-3,8-
Physical property value and analytical data of dideoxy-14-O-anisoylaconine 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.14 (1H, d, J = 5.0Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 0.99 (3H, t, J = 7.0 Hz) (H of N-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 carbonyl) 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 (16,1,6,18,14,13,15 position C) 62.2,59.1,57.8,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 13.1 (3H, t) (C of N-amyl methyl) 6 ) Mass spectrum analysis m / z 643 (M ⁺ ) (99) N-desethyl-N-propyl-16-epi-3,8
-Dideoxy-14-O-anisoylaconine physical properties and analytical data 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.13 (1H, d, J = 5.0 Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 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).

165.9 (C of anisoyl group carbonyl) 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 (16,1,6,18,14,13,15 position C) 62.1,59.0,58.0,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 13.0 (C of N-propyl methyl) 6) Mass spectrum analysis m / z 615 (M ⁺ ) (100) Physical properties and analytical data of (100) N-desethyl-N- (4-methyl) pentyl-16-epi-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.12 (1H, t, J = 5.0Hz) (14th place βH) 3.88 (3H, s) (methoxy H of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (methyl H of N- (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) 91.3,86.1,86.0,82.2,80.1,76.1,72.3 (16,1,6,18,14,13,15 position C) 62.2,59.0,57.9,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 21.5 (Methyl C of N- (4-methyl) pentyl) 6 ) Mass spectrum analysis m / z 657 (M ⁺ ). (101) N-desethyl-N-acetyl-16-epi-3,8
-Dideoxy-14-O-anisoylaconine physical properties and analytical data 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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.14 (1H, d, J = 5.0Hz) (βH at position 14) 3.87 (3H, s) (H of methoxy group of anisoyl group) 2.30 (3H, s) (H of N-acetyl methyl) 5) ¹³ 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) 163.7,131.6,113.5,122.1 (C of anisoyl group) 91.2,85.0,82.5,82.0,80.2,76.1,72.3 (16,6,18 , 1,14,13,15-position C) 62.2,59.1,58.0,56.0 (16,18,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N-acetyl methyl C) 6) Mass spectrum analysis m / z 615 (M ⁺ ) (102) N-desethyl-N-benzoyl-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 1710,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 5.14 (1H, d, J = 5.0Hz) (14th place βH) 3.87 (3H, s) (H of methoxy 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) 133.9,133.4,128.6,128.2,127.6 (C of benzoyl group) 91.3,85.0,83.4,82.0,80.3,76.0,72.5 ( 16,6,18,1,14,13,15 position C) 62.2,59.1,57.8,56.0 (16,18,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 6) Mass spectrometry m / z 677 (M ⁺ ) (103) Physical properties and analytical data of N-desethyl-16-epi-3,8,13-trideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.20 (1H, t, J = 4.8Hz) (14th place βH) 3.87 (3H, s) (H of methoxy of anisoyl 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) 163.7,131.6,113.4,122.2 (C of anisoyl group) 91.2,86.3,84.9,82.5,80.2,72.5 (C at the position of 16,1,6,18,14,15) 60.1 , 58.7, 57.9, 56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 6) Mass spectrum analysis m / z 557 (M ⁺ ) (104) N-desethyl- N-amyl-16-epi-3,8,1
Physical property value and analytical data of 3-trideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.20 (1H, t, J = 5.0Hz) (βH at position 14) 3.87 (3H, s) (methoxy H of anisoyl group) 0.98 (3H, t, J = 7.0 Hz) (H of N-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 carbonyl) 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 position 16,16,18,14,15) 60.2 , 588.8, 57.9, 56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 13.2 (C of N-amyl methyl) 6) Mass spectrum analysis m / z 627 ( M ⁺ ) (105) N-desethyl-N-propyl-16-epi-3,
Physical properties and analytical data of 8,13-trideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.19 (1H, t, J = 4.8Hz) (14th place βH) 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 carbonyl) 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 position 16,16,18,14,15) 60.1 , 58.8, 57.9, 56.0 (C of the methoxy group at the 18,16,6,1 position) 55.4 (C of the methoxy of anisoyl group) 13.0 (C of the methyl of N-propyl) 6) Mass spectrum analysis m / z 599 ( M ⁺ ) (106) 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.25 (1H, t, J = 4.8Hz) (βH at position 14) 3.88 (3H, s) (methoxyH of anisoyl group) 1.02 (6H, d, J = 7.0 Hz) (H of methyl of N- (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) 163.8,131.7,113.4,122.0 (C of anisoyl group) 91.3,86.1,85.0,82.2,80.1,72.5 (C at 16,1,6,18,14,15 position) 60.0 , 58.8,57.9,56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 21.5 (C of methyl of N- (4-methyl) pentyl) 6) Mass spectrum analysis m / z 641 (M ⁺ ) (107) N-desethyl-N-acetyl-16-epi-3,
Physical properties and analytical data of 8,13-trideoxy-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 1715,1655 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.19 (1H, t, J = 4.8Hz) (14th place βH) 3.87 (3H, s) (methoxy H of anisoyl group) 3.28 (3H, s) (H of N-acetyl methyl) 5) ¹³ C nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

171.8 (C of acetyl group carbonyl) 166.0 (C of anisoyl group carbonyl) 163.7,131.6,113.4,122.2 (C of anisoyl group) 91.2,84.9,82.5,82.0,80.2,72.4 (16,6,18,1 , 14,15 position C) 60.1,58.7,57.9,56.0 (18,16,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.0 (N-acetyl methyl C) 6 ) Mass spectrum analysis m / z 599 (M ⁺ ) (108) N-desethyl-N-benzoyl-16-epi-
Physical property values and analytical data of 3,8,13-trideoxy-14-O-anisoylaconine 1) Properties and solubility 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 1710,1653 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 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) 5.21 (1H, t, J = 4.8Hz) (βH at position 14) 3.88 (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, 127.6 (C of benzoyl group) 91.3, 85.0, 82.4, 82.0, 80.3, 72.6 (16, 6,18,1,14,15-position C) 60.2,58.8,57.9,56.0 (18,16,6,1-position methoxy group C) 55.4 (anisoyl group methoxy C) 6) Mass spectrum analysis m / z 661 (M ⁺ ) (109) Physical properties and analytical data of N-desethyl-N- (2-methyltetrahydrofurfuryl) -8-deoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.93 (1H, d, J = 5.0Hz) (14th place βH) 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,
14,18,13,15,3 position C) 61.9,59.0,57.9,56.0 (C of methoxy group of 16,18,6,1 position) 55.4 (methoxy C of anisoyl group) 21.5 (2-methyltetrahydro 6) Mass spectrum analysis 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 Physical properties and analytical data of (110) N-desethyl-N- (2-methyltetrahydrofurfuryl) -3,8-dideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

4.95 (1H, d, J = 5.0Hz) (14th place βH) 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 carbonyl) 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 (16,6,1,18,1
C at 4,13,15 position) 61.7,59.0,58.0,56.0 (C at methoxy group at 16,18,6,1 position) 55.4 (Methoxy C at anisoyl group) 21.5 (Methyl at 2-methyltetrahydrofurfuryl) C) 6) Mass spectrum analysis m / z 671 (M ⁺ ) 7) Elemental analysis C ₃₇ H ₅₃ NO ₁₀ , Calculated C: 66.15, H: 7.95, N: 2.08 Observed C: 65.89, H: 7.72, N: 1.98 Physical properties and analytical data of (111) 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.06 (1H, t, J = 4.8Hz) (14th place βH) 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 carbonyl 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 of 16,1,6,18,14,15 position) 59.3 , 58.8, 57.9, 56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 21.5 (C of methyl of 2-methyltetrahydrofurfuryl) 6) Mass spectrum analysis 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 (112) N-desethyl- Physical properties and analytical data of N- (2-methyltetrahydrofurfuryl) -16-epi-8-deoxy-14-O-anisoylaconine 1) Properties and solubility Colorless non-crystalline powder, ether, chloroform 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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.12 (1H, d, J = 5.0Hz) (14th place βH) 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 carbonyl) 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,
14,18,13,15,3 position C) 62.2,59.1,57.9,56.1 (16,18,6,1 position methoxy group C) 55.4 (anisoyl group methoxy C) 21.5 (2-methyltetrahydro 6) Mass spectrum analysis m / z 687 (M ⁺ ) (113) N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-3,8-dideoxy-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 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.14 (1H, d, J = 5.0Hz) (14th place βH) 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 carbonyl) 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 (16,1,6,18,14,13,15 position C) 62.1,59.0,58.0,56.0 (C of methoxy group at 16,18,6,1 position) 55.4 (Methoxy C of anisoyl group) 21.5 (Methyl C of 2-methyltetrahydrofurfuryl) 6) Mass Spectral analysis m / z 671 (M ⁺ ) (114) N-desethyl-N- (2-methyltetrahydrofurfuryl) -16-epi-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 1715 cm ^-1 .

3) UV absorption spectrum (ethanol) analysis 4) ¹ H Nuclear magnetic resonance spectrum (CDCl ₃ ) analysis The following signals are shown (δ, ppm).

5.19 (1H, t, J = 4.8Hz) (14th place βH) 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 position 16,16,18,14,15) 60.1 , 58.8, 57.9, 56.0 (C of methoxy group at 18,16,6,1 position) 55.4 (C of methoxy of anisoyl group) 21.5 (C of methyl of 2-methyltetrahydrofurfuryl) 6) Mass spectrum analysis m / z 655 (M ⁺ ) An experimental example of the pharmacological action and acute toxicity of the compound represented by the formula (I) is shown.

[Experimental Example 1] (Analgesic action) Measurement of analgesic activity based on acetic acid licing method Std: ddY male mice (20 to 25 g) were used in the experiments. Animals were housed at room temperature 24-25 ° C, with free access to water, water and a 12 hour light / dark condition. The test drug was used as a 3% gum arabic suspension. 30 minutes after test drug administration (sc)
0.7% acetic acid / 0.9% physiological saline was injected intraperitoneally at a rate of 10 ml / kg, and the number of licings expressed from 10 to 10 minutes after the injection was counted. 3% gum arabic / 0.9% saline was used as a negative control. The ED ₅₀ value was determined to be positive for analgesic activity if it was less than half the number of licings in the negative control group.
It was calculated based on the ld-Wilcoxon method. Table 1 shows the results.

The compounds according to the invention show a dose-dependent analgesic activity,
As shown in Table 1, the compound was found to have strong analgesic activity.

[Experimental Example 2] (Anti-inflammatory action) Measurement of carrageenan footpad edema Std: ddY male mice (20 to 25 g) were used in the experiments. Thirty minutes after the oral administration of the drug, 25 μl of carrageenin (0.5 mg / 25 μl) suspended in 0.9% physiological saline was injected subcutaneously into the right hind footpad of the mouse as an inflammation agent. As a control, 25 μl of 0.9% physiological saline was injected subcutaneously into the left hind footpad. Paw thickness was measured using a dial gauge caliper and measured 1, 2, 3, 4, 5, and 6 hours after carrageenin administration. The results were expressed as the difference between the thickness of the right and left feet. Table 2 shows the results.

As shown in Table 2, the compounds according to the present invention were found to have a carrageenan footpad edema inhibitory action.

[Experimental Example 3] (Acute toxicity) Std: ddY male mice (20 to 25 g) were used in the experiments. Litchfie based on the lethal number 72 hours after subcutaneous administration of the test drug
LD ₅₀ values were calculated based on the ld-Wilcoxon method. Table 3 shows the results.

As shown in Table 3, the compounds according to the present invention were found to be less toxic than mesaconitine, aconitine, hypoconitine and jesaconitine.

As described above, it was revealed that the compound represented by the formula (I) has lower toxicity than mesaconitine, aconitine, hypoconitine and jesaconitin, and has strong analgesic / anti-inflammatory activity.

The clinical dose of the analgesic / anti-inflammatory agent according to the present invention is preferably 1 to 1000 mg / day for an adult as the compound of the formula (I). The preparation of the present invention is used in a conventional manner using any desired preparation carrier or excipient.

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

In the injectable preparation, the compound represented by the formula (I) may be used in the form of a salt, and is preferably a soluble form at the time of use. It may also contain formulating agents such as suspending agents, stabilizers or dispersing agents, and contains sterile distilled water, essential oils such as peanut oil, corn oil or non-aqueous solvents, polyethylene glycol, polypropylene glycol and the like. You may.

For rectal administration, provided in the form of a suppository composition,
Pharmaceutical carriers well known in the art, such as polyethylene glycol, lanolin, coconut oil and the like may be included.

For topical application, they are provided in the form of an ointment or plaster composition, pharmaceutical carriers well known in the art,
For example, petrolatum, paraffin, lanolin hydrolyzate, plastibase, hydrophilic petrolatum, macrogol, wax, resin,
It may contain purified lanolin, rubber and the like.

──────────────────────────────────────────────────続 き Continuation of front page (56) References Pharmaceutical Journal, 104 (7), 731-52 (1984) Pharmaceutical Journal, 104 (8), 848-57 (1984) Heterocycles, 25 (1), 365-76 (1987) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 221/22 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] (1) General formula [Wherein, R ₁ is (i) a saturated alkyl or unsaturated alkyl having or without a substituent, or (ii) an aliphatic or aromatic acyl having or not having a substituent. Or (iii) aralkyl with or without a substituent, and R ₂ is (i) saturated or unsaturated alkyl or hydrogen with or without a substituent, or (ii) R) is an aliphatic or aromatic acyl with or without a substituent, or (iii) an aralkyl with or without a substituent, and R _{3 and} R ₄ are each hydrogen or a hydroxyl group; ₅ is hydrogen and R ₆ is a hydroxyl group. ] The aconitine type compound represented by these. 2. The general formula [Wherein, R ₁ is (i) a saturated alkyl or unsaturated alkyl having or without a substituent, or (ii) an aliphatic or aromatic acyl having or not having a substituent. Or (iii) aralkyl with or without a substituent, and R ₂ is (i) saturated or unsaturated alkyl or hydrogen with or without a substituent, or (ii) R) is an aliphatic or aromatic acyl with or without a substituent, or (iii) an aralkyl with or without a substituent, and R _{3 and} R ₄ are each hydrogen or a hydroxyl group; ₅ is hydrogen and R ₆ is a hydroxyl group. ] An analgesic / anti-inflammatory agent comprising the aconitine compound represented by the formula (1) as an active ingredient.