CN101585825A - Method for preparing amentoflavone - Google Patents
Method for preparing amentoflavone Download PDFInfo
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- CN101585825A CN101585825A CNA200910012091XA CN200910012091A CN101585825A CN 101585825 A CN101585825 A CN 101585825A CN A200910012091X A CNA200910012091X A CN A200910012091XA CN 200910012091 A CN200910012091 A CN 200910012091A CN 101585825 A CN101585825 A CN 101585825A
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- tridemethylsciadopitysin
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Abstract
The invention belongs to the technical field of medicaments, and provides a method for preparing amentoflavone of which the content is over 95 percent from a Chinese medicament of herba selaginellae. The compound has a structure as shown in the formula (I). A dried herbal material of selaginella tamariscina(Beauv.)spring or selaginella pulvinata(Hook.et Grev.)maxim. is taken as an initial raw material, extracted by organic solvent and/or water, and separated by a column chromatography separation method to obtain the amentoflavone. The method has the advantages of simple process operation, good repeatability, high yield and the suitability for industrialized production; and the product is high in purity, and the content of the product is measured to be over 95 percent by an HPLC method.
Description
Technical field:
The present invention relates to the preparation method of Tridemethylsciadopitysin in the Selaginella tamariscina (amentoflavone), its content adopts the HPLC method to detect should be more than 95%.Belong to traditional Chinese medicine extraction separation, purifying field.
Background technology:
The regulation Selaginella tamariscina is the dry herb of Spikemoss plant Selaginella tamariscina Selaginellatamariscina (Beauv.) Spring or cushion Selaginella tamariscina Selaginella pulvinata (Hook.et Grev.) Maxim. in the Chinese Pharmacopoeia version in 2005.All can gather the whole year, removes fibrous root and silt, dries.Suffering, flat.Return liver, the heart channel of Hang-Shaoyin.Has promoting blood circulation to restore menstrual flow.Be used for through closing dysmenorrhoea ， Disorder lump in the abdomen lump in the abdomen, injury from falling down.The hemostasis of the Selaginella tamariscina charing stasis of blood.Be used for spitting blood, uterine bleeding is had blood in stool, prolapse of the anus.Contain the number of chemical composition in the Selaginella tamariscina, as flavonoid, have now found that and contain apigenin (apigenin), Tridemethylsciadopitysin (amentoflavone), hinokiflavone (hinokiflavone), isocryptomerin (isocryptomerin) and Oman's holder yellow (amentoflavone) etc. in the Selaginella tamariscina; Compounds such as the plain class of phenylpropyl alcohol, alkaloids, phenols, organic acid.Pharmacological action shows to have: immunity and antitumor action, to effects such as the effect of blood system, antiviral, antibacterial and anti-inflammatory action, antalgic and sedatives.The invention provides a kind of convenience, easy, prepare the method for high purity Tridemethylsciadopitysin fast.Do not see the extracting method of this Tridemethylsciadopitysin at present in the prior art.
Summary of the invention:
Technical problem to be solved by this invention provides extracts the preparation method of a kind of content at the Tridemethylsciadopitysin more than 95% (amentoflavone) in a kind of therefrom powder stick cypress, purpose is the Tridemethylsciadopitysin (amentoflavone) that obtains content higher (content is greater than 95%) by simple technological process.
Technical scheme of the present invention is: therefrom extract the preparation method of a kind of content at the Tridemethylsciadopitysin more than 95% (amentoflavone) in the powder stick cypress, its concrete grammar step is:
A) the dry herb raw material with Spikemoss plant Selaginella tamariscina Selaginella tamariscina (Beauv.) Spring or cushion Selaginella tamariscina Selaginella pulvinata (Hook.et Grev.) Maxim. is cut into a cun section;
B) with a kind of and water in a kind of or ethanol and the methyl alcohol in the ethanol, methyl alcohol, water in proportion (1: 10～10: 1) mix and/or with water blended mixed solvent refluxing extraction, add the 2-16 times of solvent that is equivalent to medicinal material weight, refluxing extraction 1-5 time, each 0.5 to 6 hour, united extraction liquid, filter, get extracting solution;
C) extracting solution is reclaimed solvent and be concentrated into clear cream or the thick paste that relative density is 1.05-1.40 (60 ℃), placed 0.5-24 hour, filter, solid sediment.
D) a kind of or any two kinds of (1: 10～10: 1) the blended mixed solvent dissolvings in proportion in the sherwood oil doubly measured with 2-100 of solid sediment, ether, ethyl acetate, acetone, trichloromethane, ethanol, the methyl alcohol.
E) organic solvent of solid sediment or mixed organic solvents being added with silica gel is to adsorb on the chromatography column of sorbent material.
F) silica gel column chromatography that will adsorb solid sediment with sherwood oil, ether, ethyl acetate, acetone, trichloromethane is a kind of or any two kinds in proportion (1: 10～10: 1) blended mixed solvent respectively with the mixed solvent wash-out of ethanol or methyl alcohol (10: 1～1: 1), collect eluent stream part with the volume of every part 1/100～1/20 total amount eluent respectively, with trichloromethane: methyl alcohol (10: 1～1: 1) is that developping agent adopts TLC to check spot, merges identical yellow spotting wash-out stream part.
The identical yellow spotting wash-out stream part recovery solvent that g) will merge gets the yellow solid powder.
H) (1: 10～10: 1) the blended mixed organic solvents dissolving in proportion of one or more in the sherwood oil that the yellow solid powder is doubly measured with 2-100, ether, ethyl acetate, acetone, trichloromethane, ethanol, the methyl alcohol.
I) organic solvent of yellow solid powder or mixed organic solvents being added with Sephadex LH-20 is to adsorb on the chromatography column of sorbent material.
J) the Sephadex LH-20 chromatography column that will adsorb the yellow solid powder with sherwood oil, ether, ethyl acetate, acetone, trichloromethane is a kind of or any two kinds in proportion (1: 10～10: 1) blended mixed solvent respectively with the mixed solvent wash-out of ethanol or methyl alcohol (10: 1～1: 1), collect the yellow colour band of Sephadex LH-20 chromatography column respectively with the volume of every part 1/100～1/20 total amount eluent, until fully.With trichloromethane: methyl alcohol (10: 1～1: 1) is that developping agent adopts TLC follow-up investigations spots, merges identical yellow spotting wash-out stream part.
The identical yellow spotting wash-out stream that k) will merge part reclaims a solvent, the yellow solid powder, i.e. Tridemethylsciadopitysin (amentoflavone) highly finished product, its content adopts the HPLC method to detect should be more than 95%.
Tridemethylsciadopitysin
The Tridemethylsciadopitysin structure elucidation:
Figure The?structure?of?amentoflavone
Yellow powder, FeCL
3Reaction, hydrochloric acid-magnesium powder reaction all is positive, and points out it may be flavonoid compound.
1H NMR (300MHz, DMSO-d
6) spectrum finds relatively that with single flavones hydrogen spectrogram (H-II3), 6.82 (1H, s H-I3) are two 3 proton signals of biflavone to δ 6.78 for 1H, s; And in the low place of hydrogen spectrum 6 hydroxyl proton signals are arranged: (H-I5), 12.96 (1H, s H-II5) are the 5-hydroxyl of two flavones for 1H, s to be respectively δ 13.09; δ 10.55 (2H, brs, 4 " OH and H-4 " '-OH); 10.82 (1H, s, 7-OH), 10.28 (1H, s, 7 " OH), in conjunction with
13C NMR (75MHz, DMSO-d
6) 30 carbon signals providing in the spectrum, further point out this compound may be biflavone.δ 6.45 in the hydrogen spectrum (1H, d, J=2.0Hz, H-8), 6.18 (J=2.0Hz H-6) prompts for flavone A interannular digit pair and closes proton for 1H, d, illustrates that some flavone A rings are 5, and the 7-dihydroxyl replaces; A Last sharp-pointed unimodal signal is δ 6.39 (1H in the hydrogen spectrum, s), supposition may be 6 or 8 protons of another flavones, illustrates that this biflavone compound is to be linked to each other with certain proton of another flavones B ring by 6 on the flavones structural unit A ring or 8.δ 7.58 (2H, d, J=8.7Hz, H-2 " ', 6 " '), AA ' BB ' coupling system that δ 6.72 (2H, d, J=8.7Hz, H-3 " ', 5 " ') forms when prompting for one of them flavones B ring para-orientation.
Also be left 3 hydrogen signals in the hydrogen spectrum this moment, according to peak type and coupling constant, infers that one of them flavones B ring is ABX coupling system, also further specify simultaneously these two flavones by 3 of one of them B ring ' or 5 ' position and another flavones 6 or 8 protons link to each other, specifically belong to as follows: δ 7.15 (1H, d, J=9.3Hz), δ 8.01 (1H, d, J=2.0Hz, 6.9Hz), δ 7.99 (1H, d, J=2.0Hz) (above formation ABX system).By with single flavones
13C NMR compares, and the C-8 of one of them flavones shifts to low place, and chemical displacement value increases about 6ppm, and showing has other group to link to each other really, and the ABX coupling system in conjunction with flavones B ring in the hydrogen spectrum exists infers that further two single flavones are really with 3 '-8 and " connects.According to above proton distribution situation, so infer that this compound is amentoflavone.Structure such as Figure.
Table amentoflavone
1H NMR and
13C NMR attribution data (300,75MHz, DMSO-d
6)
Advantage of the present invention is:
(1) simple, the good reproducibility of technological operation, the productive rate height is suitable for suitability for industrialized production.
(2) purity of this product is higher, and its content adopts the HPLC method to detect more than 95%.
The application of Tridemethylsciadopitysin (amentoflavone):
(1) Tridemethylsciadopitysin of the present invention (amentoflavone) is suitable for preparing the a kind new medicine preparation that uses clinically.
(2) Tridemethylsciadopitysin of the present invention (amentoflavone) also can with other compound or medication combined use, the new drug preparation that preparation is used clinically.
(3) Tridemethylsciadopitysin of the present invention (amentoflavone) can be made the various pharmaceutical dosage forms that use clinically.
(3) Tridemethylsciadopitysin of the present invention (amentoflavone) also can use as reference substance.
(4) Tridemethylsciadopitysin of the present invention (amentoflavone) also can be made various protective foods and the functional cosmetics that use clinically.
Embodiment:
Come more detailed description the present invention below in conjunction with embodiment, but the present invention is not subjected to the restriction of these embodiment.
Embodiment 1:
With dry Selaginella tamariscina herb 100g, be cut into a cun section, add 30% alcohol reflux three times, add 11 times of amounts at every turn, each 2 hours, united extraction liquid filtered, and gets extracting solution.Extracting solution is reclaimed ethanol and be concentrated into the clear cream that relative density is 1.30 (60 ℃), placed 12 hours, filter, get solid sediment.It is to adsorb on the chromatography column of sorbent material that solid sediment is added with silica gel after with the dissolve with methanol of 40 times of amounts.The silica gel column chromatography mixed solvent gradient elution of trichloromethane and methyl alcohol (10: 1～1: 1), volume with every part 1/40 total amount eluent is collected eluent stream part, adopt TLC to check spot (with trichloromethane: methyl alcohol be developping agent at 3: 1), merges identical yellow spotting wash-out and flow part.Identical yellow spotting wash-out stream part recovery solvent with merging gets the yellow solid powder.Behind the acetone solution of yellow solid powder with 30 times of amounts, adding with Sephadex LH-20 is to adsorb on the chromatography column of sorbent material.With the mixed solvent wash-out of Sephadex LH-20 chromatography column, respectively with the yellow colour band of the volume collection Sephadex LH-20 chromatography column of every part 1/30 total amount eluent, until fully with trichloromethane and methyl alcohol (3: 1).Adopt TLC follow-up investigations spot (with trichloromethane: methyl alcohol be developping agent at 4: 1), merges identical yellow spotting wash-out and flow part.The identical yellow spotting wash-out stream that merges part is reclaimed a solvent, the yellow solid powder, i.e. Tridemethylsciadopitysin (amentoflavone) highly finished product, it is on 98.1% that its content adopts the HPLC method to detect.
Embodiment 2:
With dry Selaginella tamariscina herb 2kg, be cut into a cun section, add 75% alcohol reflux three times, add 10 times of amounts at every turn, each 1.5 hours, united extraction liquid filtered, and gets extracting solution.Extracting solution is reclaimed ethanol and be concentrated into the clear cream that relative density is 1.10 (60 ℃), placed 8 hours, filter, get solid sediment.It is to adsorb on the chromatography column of sorbent material that solid sediment is added with silica gel after with the acetic acid ethyl dissolution of 30 times of amounts.The silica gel column chromatography mixed solvent gradient elution of trichloromethane and methyl alcohol (10: 1～1: 1), volume with every part 1/30 total amount eluent is collected eluent stream part, adopt TLC to check spot (with trichloromethane: methyl alcohol be developping agent at 2: 1), merges identical yellow spotting wash-out and flow part.Identical yellow spotting wash-out stream part recovery solvent with merging gets the yellow solid powder.Behind the acetone solution of yellow solid powder with 20 times of amounts, adding with Sephadex LH-20 is to adsorb on the chromatography column of sorbent material.With the mixed solvent wash-out of Sephadex LH-20 chromatography column, respectively with the yellow colour band of the volume collection SephadexLH-20 chromatography column of every part 1/20 total amount eluent, until fully with trichloromethane and methyl alcohol (4: 1).Adopt TLC follow-up investigations spot (with trichloromethane: methyl alcohol be developping agent at 2: 1), merges identical yellow spotting wash-out and flow part.The identical yellow spotting wash-out stream that merges part is reclaimed a solvent, the yellow solid powder, i.e. Tridemethylsciadopitysin (amentoflavone) highly finished product, it is 96.6% that its content adopts the HPLC method to detect.
Embodiment 3:
With dry Selaginella tamariscina herb 30kg, be cut into a cun section, add 50% alcohol reflux three times, add 9 times of amounts at every turn, each 1.5 hours, united extraction liquid filtered, and gets extracting solution.Extracting solution is reclaimed ethanol and be concentrated into the clear cream that relative density is 1.25 (60 ℃), placed 6 hours, centrifugal, get solid sediment.It is to adsorb on the chromatography column of sorbent material that solid sediment is added with silica gel after with the acetone solution of 20 times of amounts.The silica gel column chromatography mixed solvent gradient elution of trichloromethane and methyl alcohol (10: 1～1: 1), volume with every part 1/20 total amount eluent is collected eluent stream part, adopt TLC to check spot (with trichloromethane: methyl alcohol be developping agent at 3: 1), merges identical yellow spotting wash-out and flow part.Identical yellow spotting wash-out stream part recovery solvent with merging gets the yellow solid powder.Behind the acetone solution of yellow solid powder with 10 times of amounts, adding with Sephadex LH-20 is to adsorb on the chromatography column of sorbent material.With the mixed solvent wash-out of Sephadex LH-20 chromatography column, respectively with the yellow colour band of the volume collection Sephadex LH-20 chromatography column of every part 1/30 total amount eluent, until fully with trichloromethane and methyl alcohol (3: 1).Adopt TLC follow-up investigations spot (with trichloromethane: methyl alcohol be developping agent at 3: 1), merges identical yellow spotting wash-out and flow part.The identical yellow spotting wash-out stream that merges part is reclaimed a solvent, the yellow solid powder, i.e. Tridemethylsciadopitysin (amentoflavone) highly finished product, it is 95.3% that its content adopts the HPLC method to detect.
Claims (10)
1, a kind of Tridemethylsciadopitysin has the structure as shown in the formula (I): it is characterized in that: its content is more than 95%.
2, Tridemethylsciadopitysin according to claim 1 is characterized in that: the English of described Tridemethylsciadopitysin is by name: amentoflavone; Molecular formula is C
30H
18O
10Molecular weight is 538.47.
3, a kind of preparation method of Tridemethylsciadopitysin as claimed in claim 1 is characterized in that: it is raw material that this method adopts Chinese medicine Selaginella tamariscina, extracts or adopts column chromatography to separate with organic solvent and/or water.
4, the preparation method of Tridemethylsciadopitysin according to claim 3 is characterized in that: described Chinese medicine Selaginella tamariscina is: the dry herb raw material of Spikemoss plant Selaginella tamariscina Selaginella tamariscina (Beauv.) Spring or cushion Selaginella tamariscina Selaginella pulvinata (Hook.et Grev.) Maxim..
5, the preparation method of Tridemethylsciadopitysin according to claim 3, it is characterized in that: in the described extracting method, described solvent comprises a kind of in ethanol, methyl alcohol, the water, 1: 10 in proportion～10: 1 blended mixed solvents of a kind of and water in ethanol, the methyl alcohol.
6, the preparation method of Tridemethylsciadopitysin according to claim 3 is characterized in that: in the described column chromatography separation method, used column chromatography sorbent material is silica gel, Sephadex LH-20.
7, the preparation method of Tridemethylsciadopitysin according to claim 3, it is characterized in that: in the described column chromatography separation method, used column chromatography eluent is a kind of or any two kinds of 10: 1 in proportion～1: the 10 blended mixed organic solvents in sherwood oil, ether, ethyl acetate, acetone, trichloromethane, ethanol, the methyl alcohol.
8, the preparation method of Tridemethylsciadopitysin according to claim 3 is characterized in that: described concrete grammar may further comprise the steps:
A) the dry herb raw material with Spikemoss plant Selaginella tamariscina Selaginella tamariscina (Beauv.) Spring or cushion Selaginella tamariscina Selaginella pulvinata (Hook.et Grev.) Maxim. is cut into a cun section;
B) with a kind of and 1: 10 in proportion～10: 1 blended mixed solvents of the water refluxing extraction in a kind of or ethanol and the methyl alcohol in ethanol, methyl alcohol, the water, add the 2-16 times of solvent that is equivalent to medicinal material weight, refluxing extraction 1-5 time, each 0.5 to 6 hour, united extraction liquid filters, and gets extracting solution;
C) extracting solution is reclaimed solvent and be concentrated into clear cream or the thick paste that 60 ℃ of following relative densities are 1.05-1.40, placed 0.5-24 hour, filter, solid sediment;
D) solid sediment is doubly measured a kind of or any two kinds of 1: 10 in proportion～10: the 1 blended mixed solvents dissolving in the sherwood oil, ether, ethyl acetate, acetone, trichloromethane, ethanol, methyl alcohol of (by weight/volume) with 2-100;
E) organic solvent of solid sediment or mixed organic solvents being added with silica gel is to adsorb on the chromatography column of sorbent material;
F) silica gel column chromatography that will adsorb solid sediment with sherwood oil, ether, ethyl acetate, acetone, trichloromethane is a kind of or any two kinds of 1: 10 in proportion～10: 1 blended mixed solvents respectively with ethanol or 10: 1～1: 1 mixed solvent wash-out of methyl alcohol, collect eluent stream part with the volume of every part 1/100～1/20 total amount eluent respectively, with trichloromethane: methyl alcohol 10: 1～1: 1 was that developping agent adopts TLC to check spot, merged identical yellow spotting wash-out stream part;
The identical yellow spotting wash-out stream part recovery solvent that g) will merge gets the yellow solid powder;
H) a kind of or any two kinds of 1: 10 in proportion～10: the 1 blended mixed organic solvents dissolving in the sherwood oil that the yellow solid powder is doubly measured with 2-100, ether, ethyl acetate, acetone, trichloromethane, ethanol, the methyl alcohol;
I) organic solvent of yellow solid powder or mixed organic solvents being added with Sephadex LH-20 is to adsorb on the chromatography column of sorbent material;
J) the Sephadex LH-20 chromatography column that will adsorb the yellow solid powder with sherwood oil, ether, ethyl acetate, acetone, trichloromethane is a kind of or any two kinds of 1: 10 in proportion～10: 1 blended mixed solvents respectively with ethanol or 10: 1～1: 1 mixed solvent wash-out of methyl alcohol, collect the yellow colour band of Sephadex LH-20 chromatography column respectively with the volume of every part 1/100～1/20 total amount eluent, until fully; With trichloromethane: methyl alcohol 10: 1～1: 1 was that developping agent adopts TLC follow-up investigations spots, merged identical yellow spotting wash-out stream part;
The identical yellow spotting wash-out stream that k) will merge part reclaims a solvent, the yellow solid powder, i.e. Tridemethylsciadopitysin highly finished product, its content adopts the HPLC method to detect should be more than 95%.
9, Tridemethylsciadopitysin according to claim 1 is characterized in that: described Tridemethylsciadopitysin can be prepared into acceptable clinically various preparations with pharmaceutically acceptable carrier or vehicle combination.
10, Tridemethylsciadopitysin according to claim 8 is characterized in that: described preparation comprises tablet, capsule, granule, injection, dripping pill.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101732306A (en) * | 2009-12-03 | 2010-06-16 | 沈阳药科大学 | New application of natural product amentoflavone in treating cancers |
| CN102285950A (en) * | 2011-09-07 | 2011-12-21 | 上海交通大学 | Application of amentoflavone |
| CN102731592A (en) * | 2012-06-25 | 2012-10-17 | 向华 | Method for extracting cleupin and amentoflavone from olive leaf |
| CN103087025A (en) * | 2013-02-22 | 2013-05-08 | 天津科技大学 | Complete synthesis method of secondary metabolic active component amentoflavone |
| CN109320486A (en) * | 2017-08-01 | 2019-02-12 | 复旦大学 | A kind of method of amentoflavone in infrared extraction Selaginella tamariscina |
| CN114394950A (en) * | 2022-01-19 | 2022-04-26 | 四川省中医药科学院 | Biflavonoid compound for resisting I-type simplex herpes virus as well as preparation method and application thereof |
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| CN101361765A (en) * | 2008-09-19 | 2009-02-11 | 湖北中医学院 | Anti-coxsackie and anti-herpesvirus extract of selaginella tamariscina and extraction technique and formulation thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101732306A (en) * | 2009-12-03 | 2010-06-16 | 沈阳药科大学 | New application of natural product amentoflavone in treating cancers |
| CN102285950A (en) * | 2011-09-07 | 2011-12-21 | 上海交通大学 | Application of amentoflavone |
| CN102285950B (en) * | 2011-09-07 | 2013-03-20 | 上海交通大学 | Application of amentoflavone |
| CN102731592A (en) * | 2012-06-25 | 2012-10-17 | 向华 | Method for extracting cleupin and amentoflavone from olive leaf |
| CN102731592B (en) * | 2012-06-25 | 2015-09-23 | 湖南农业大学 | A kind of method extracting oleuropein and Tridemethylsciadopitysin from olive leaf |
| CN103087025A (en) * | 2013-02-22 | 2013-05-08 | 天津科技大学 | Complete synthesis method of secondary metabolic active component amentoflavone |
| CN109320486A (en) * | 2017-08-01 | 2019-02-12 | 复旦大学 | A kind of method of amentoflavone in infrared extraction Selaginella tamariscina |
| CN114394950A (en) * | 2022-01-19 | 2022-04-26 | 四川省中医药科学院 | Biflavonoid compound for resisting I-type simplex herpes virus as well as preparation method and application thereof |
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|---|---|
| CN101585825B (en) | 2013-11-27 |
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