CN1308277C - Method of extracting anthraquinone analog compound from traditional Chinese medicine cassia seed - Google Patents
Method of extracting anthraquinone analog compound from traditional Chinese medicine cassia seed Download PDFInfo
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Abstract
本发明涉及从中药决明子中提取蒽醌类化合物的方法，包括(1)分部提取、(2)不溶于95%乙醇的混合物的制备、(3)大孔树脂分离纯化不溶于95%乙醇的混合物、(4)硅胶柱分离纯化乙醇洗脱物和蒽醌类化合物的分离、纯化；得到降脂有效成分大黄素-1-O-β-龙胆二糖甙、大黄酚-1-O-β-龙胆二糖甙、大黄素甲醚-8-O-β-龙胆二糖甙、大黄酚-1-O-β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖甙。The invention relates to a method for extracting anthraquinone compounds from the traditional Chinese medicine Semen Cassiae, comprising (1) partial extraction, (2) preparation of a mixture insoluble in 95% ethanol, (3) separation and purification of a macroporous resin insoluble in 95% ethanol (4) Separation and purification of the ethanol eluate and anthraquinone compounds through silica gel column separation and purification; the lipid-lowering active ingredients emodin-1-O-β-gentiobioside, chrysophanol-1-O- β-gentiobioside, emodin-8-O-β-gentiobioside, chrysophanol-1-O-β-D-glucopyranosyl-(1→3)-β-D -Glucopyranosyl-(1→6)-β-D-glucopyranoside.
Description
Technical field
The present invention relates to a kind of method of from study of semen cassia (Cassia obtusifolia L.), extracting anthraquinone analog compound.Promptly from study of semen cassia, extract Schuttgelb-1-O-β-gentiobioside, chrysophanol-1-O-β-gentiobioside, rheochrysidin-8-O-β-gentiobioside and chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-four kinds of anthraquinone analog compounds of D-glucopyanoside.
Background technology
Semen Cassiae is the dry mature seed of leguminous plants Cassia tora Cassia obtusifolia L. or little Cassia tora Cassia tora L., is clinical conventional Chinese medicine.A large amount of studies show that: the extract of organic solvents such as Semen Cassiae water decoction and ethanol, propyl carbinol, ethyl acetate, Semen Cassiae medicinal extract etc. all has tangible effect for reducing fat.Further research thinks that the main component of Semen Cassiae lipopenicillinase has: anthraquinone class, Semen Cassiae glycosides B, protein etc.But the effective constituent of its lipopenicillinase is still unclear, and Shang Weijian has the lipopenicillinase composition report of particular chemical.
The chemical ingredients of Semen Cassiae mainly contains anthraquinone class, naphthalene a pair of horses going side by side one pyrrones, protein and amino acid, lipid acid, unsaponifiable matter matter, sugar and inorganic elements etc.The anthraquinone class is one of main medicinal ingredients of Semen Cassiae, and its content accounts for about 1.2%.At present oneself from Semen Cassiae isolation identification more than 20 kind of anthraquinone analog compound.Mainly be chrysophanol in the anthraquinone aglycon of Semen Cassiae, content be 2.7 ‰ (Wang Qinghua, the discipline tinkling of pieces of jade, Cong Baozhong, Song Weijing. the content of chrysophanol in the high effective liquid chromatography for measuring Semen Cassiae. the Chinese materia medica journal, 1996,5:48-49).Get chrysophanol, rheochrysidin, Schuttgelb, rhabarberone, aurantio-obtusin, rheochrysidin-8-O-β-6 anthraquinone analog compound (Hao Yanjun of D-glucoside in the therefrom homemade first Cassia tora such as Hao Yanjun, Sang Yuli, Zhao Yuqing. Semen Cassiae anthraquinone class chemical constitution study, herbal medicine, 2003,34:18-19).
The chemical ingredients of Semen Cassiae is very complicated, and separation method commonly used at present mainly contains lixiviation process, extraction process, chromatography etc.Use these methods to be difficult to the chemical ingredients in the Semen Cassiae is separated fully, and be more difficult to get monomeric compound.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of anthraquinone analog compound monomer methods of extracting from study of semen cassia is provided, can obtain Schuttgelb-1-O-β-gentiobioside, chrysophanol-1-O-β-gentiobioside, rheochrysidin-8-O-β-gentiobioside, chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-four kinds of anthraquinone analog compounds of D-glucopyanoside by this method, further development and use in effect for reducing fat have great importance to Semen Cassiae for this.
In order to reach purpose of the present invention, present method adopts the extraction of solvent branch, macroporous resin adsorption and silica gel column chromatography that study of semen cassia is separated, and 4 compounds have been identified by analysis of physical and chemical property and wave spectrum analysis, wherein Schuttgelb-1-O-β-gentiobioside is new anthraquinone analog compound, and chrysophanol-1-O-β-gentiobioside is to separate first to obtain from Semen Cassiae with chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.
Concretely, the inventive method comprises the steps:
(1) study of semen cassia is clayed into power, adopt solvent branch extraction method, according to polarity by little to greatly successively with solvent hexanaphthene, chloroform, ethyl acetate, propyl carbinol, ethanol, water each refluxing extraction 4～6 times in the Soxhlet extraction apparatus, the 1.5-2.5 that each used solvent volume is the herb powder volume doubly, each extraction time is 40-80 minute, and temperature is 60 ± 5 ℃; Merge each extracting solution in step by step, reclaim solvent, obtain aqueous extract;
(2) aqueous extract that step (1) is obtained is dissolved in the distilled water of 5.0-10.0 times of volume, filter and remove insolubles, n-butanol extraction 4-8 time of water-soluble part, the used volume of each extraction is 0.5-1.5 a times of aqueous solution volume, each extraction time is 20-40 minute, and combining extraction liquid volatilizes solvent, the mixture that obtains is isolated and is insoluble to 95% alcoholic acid mixture with 95% dissolve with ethanol of 3.0-8.0 times of volume;
(3) the 95% alcoholic acid mixture that is insoluble to that step (2) is obtained is dissolved in the distilled water of 3-5 times of volume, the impurity of elimination indissoluble, the solution macroporous adsorptive resins of partly flowing through; Being adsorbed on significant part on the post, to adopt 95% ethanol, water to be eluted to successively colourless, collects ethanol eluate, concentrate the ethanol elution thing;
(4) the ethanol elution thing that obtains with 100～200 order silicagel column separating steps (3) adopts chloroform-methanol-water elution system;
(5) chloroform in the elution system of set-up procedure (4): the volume of methyl alcohol=4: 1, the mixture that obtains is through silica gel column chromatography, adopt ethyl acetate: the volume wash-out of 95% ethanol=4: 1.5, the mixture that obtains is further through polyamide column chromatography, methyl alcohol: the volume wash-out of water=2: 3 obtains anthraquinone analog compound II and anthraquinone analog compound III;
Adjust chloroform in the elution system: the volume of methyl alcohol=3: 1, the mixture that obtains is through silicagel column chromatography repeatedly, and adopt ethyl acetate: the volume wash-out of 95% ethanol=3-5: 1.0-2.0 obtains anthraquinone analog compound I;
Adjust chloroform in the elution system: methyl alcohol: the volume of water=3: 1: 0.1, the mixture that obtains is used methyl alcohol through polyamide column chromatography: the mixture that the volume wash-out of water=2: 3 obtains further obtains anthraquinone analog compound IV through gel filtration chromatography, water elution.
(UV NMR) resolves and identifies, confirms described for MS, IR by the general analysis of physical and chemical property in this area and wave spectrum
Anthraquinone analog compound I be Schuttgelb-1-O-β-gentiobioside,
Anthraquinone analog compound II be chrysophanol-1-O-β-gentiobioside,
Anthraquinone analog compound III is rheochrysidin-8-O-β-gentiobioside
Anthraquinone analog compound IV is chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.
In step (1), the used Semen Cassiae of the present invention can be buied from the common Chinese room, clays into power earlier during use, crosses the 100-200 mesh sieve.In all solvents, each extraction time is preferably 55-65 minute, the volume that at every turn extracts solvent with 2.0 times of medicine volume for good.When whenever changing another kind of solvent extraction, residue all must volatilize solvent.
In step (2), the extraction of propyl carbinol is at room temperature carried out, extract at every turn volume with 0.5 times of the sample solution volume for good, the time that at every turn extracts with 25 minutes for good; Preferably fully shook up, place 20 minutes after adding 95% ethanol in the mixture that obtains, precipitation is separated out partly to be and is insoluble to 95% alcoholic acid mixture, called after mixture C.
In step (3): the macroporous adsorbent resin medium refills post after rinsing well with acetone-alcohol-water successively.The used solvent of separation and purification is good with analytical pure, and the consumption of macroporous resin, silica gel, polymeric amide and gel is all decided on the amount of sample.
In four kinds of anthraquinone analog compounds that the present invention obtained, Schuttgelb-1-O-β-gentiobioside is a new compound, and chrysophanol-1-O-β-gentiobioside is to separate first to obtain from Semen Cassiae with chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.Through identifying that the molecular formula of Schuttgelb-1-O-β-gentiobioside is C
27H
30O
15The molecular formula of other three kinds of compound identification is respectively C
27H
30O
14(II), C
28H
32O
15(III) and C
33H
40O
19(IV).The plane structure chart of four kinds of anthraquinone analog compounds is:
Compound I R
1=glc (1 → 6) glc, R
2=OH, R
3=H
Compound I I R
1=R
2=H, R
3=glc (1 → 6) glc
Compound III R
1=H, R
2=OCH
3, R
3=glc (1 → 6) glc
Compound IV R
1=glc (1 → 3) glc (1 → 6) glc, R
2=R
3=H
The present invention compared with prior art has following advantage:
(1) adopt the solvent merological approach to extract Semen Cassiae lipopenicillinase effective constituent;
(2) from Semen Cassiae, separate first and obtain new compound Schuttgelb-1-O-β-gentiobioside; Chrysophanol-1-O-β-gentiobioside is to separate first to obtain from Semen Cassiae with chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.
Description of drawings
Fig. 1 is the general flow chart of the inventive method;
Fig. 2 is step of the present invention (a 1) schema;
Fig. 3 is step of the present invention (a 2) schema
Fig. 4 is step of the present invention (3), (4) and (5) schema.
Concrete embodiment
Fig. 1 is the general flow chart of extraction separation Semen Cassiae anthraquinone analog compound of the present invention, as can be seen from the figure, preparation, (3) the macroporous resin separation and purification that the present invention includes that (1) branch extracts, (2) is insoluble to 95% alcoholic acid mixture is insoluble to the separating of 95% alcoholic acid mixture, (4) silicagel column separation and purification ethanol elution thing and anthraquinone analog compound, purifying.
Embodiment 1
Fig. 2 is a step of the present invention (1)---the extraction procedure figure of Semen Cassiae solvent branch.Used Semen Cassiae is purchased in the pharmacy in this example, and produce in Anhui.Depend on pine torch 500g, clay into power, cross the 100-200 mesh sieve.Adopt solvent branch extraction method, according to polarity by little to big order successively with solvent (hexanaphthene-chloroform-ethyl acetate-propyl carbinol-ethanol-water) each refluxing extraction 5 times in the Soxhlet extraction apparatus, merge each extracting solution step by step, reclaim solvent, obtain this corresponding extract step by step.Each used solvent volume is about 2 times of cassia seed powder.Each reflux extracting time is 60 minutes.When whenever changing another kind of solvent extraction, residue all must volatilize solvent.The experimentation on animals result shows that cassia seed powder and ethyl acetate extract, n-butanol extract, ethanol extraction and water extract all have tangible prophylactic effect to the formation of hyperlipemia animal model, with effect the best of aqueous extract, therefore choosing aqueous extract carries out next step separation.
Fig. 3 is step of the present invention (2)---the preparation flow figure of Semen Cassiae mixture C.Aqueous extract in the step (1) is dissolved in the distilled water of 10 times of volumes, filters and remove insolubles, n-butanol extraction 6 times of water-soluble part, each extraction volume is 0.5 times of the aqueous solution, and the extraction time is 30 minutes at every turn, combining extraction liquid, volatilize solvent, get mixture A; Mixture A is fully dissolved with 95% ethanol of 3 times of volumes, isolate and be insoluble to 95% alcoholic acid mixture C.The experimentation on animals result shows that mixture C has significant therapeutic action to hyperlipidaemia.
Fig. 4 is step of the present invention (3), (4), (5)---the isolation and purification synoptic diagram of Semen Cassiae anthraquinone analog compound.Shown in step (3), (4), (5): mixture C fully is dissolved in the distilled water of 3 times of volumes the impurity of elimination indissoluble, the solution macroporous adsorptive resins of partly flowing through.Being adsorbed on significant part on the post, to adopt 95% ethanol, water to be eluted to successively colourless, collects the elutriant of ethanol and water section respectively, concentrate, dry-matter.Ethanol elution gained material is far more than the water elution part, and active detected result shows that the ethanol elution thing has significantly effect for reducing fat.Therefore collecting the ethanol elution thing carries out next step separation and purification.
The ethanol elution thing is used silica gel (100～200 order) column chromatography (chloroform-methanol-water is elution system) respectively, and gel column (water elution) and polyamide column chromatography (methanol-water is an elution system) are got Compound I～IV.By this area general analysis of physical and chemical property and wave spectrum (MS, IR, UV, NMR) parsing has identified that Compound I is that Schuttgelb-1-O-β-gentiobioside, Compound I I are that chrysophanol-1-O-β-gentiobioside, compound III are that rheochrysidin-8-O-β-gentiobioside and compound IV are chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.Wherein I is a new compound, and II is to separate first to obtain from Semen Cassiae with IV.
Embodiment 2
Other is with embodiment 1, and that different is Semen Cassiae 1000g in the step (1), and each refluxing extraction is 4 times in the Soxhlet extraction apparatus, and each used solvent volume is 2.5 times of cassia seed powder, and each extraction time is 40 minutes; In the step (2) aqueous extract is dissolved in the distilled water of 5 times of volumes, water-soluble part is with n-butanol extraction 8 times, extracts volume at every turn and be 1 times of aqueous solution volume, and the extraction time is 40 minutes at every turn, and combining extraction liquid volatilizes solvent, mixture A.Mixture A is fully dissolved with 5 times 95% ethanol, isolate and be insoluble to 95% alcoholic acid mixture C; In the step (3) mixture C fully is dissolved in 4 times the distilled water, the solution macroporous adsorptive resins of partly flowing through, being adsorbed on significant part on the post, to adopt 95% ethanol, water to be eluted to successively colourless, collects ethanol eluate, concentrate, the ethanol elution thing.The result obtains required compound.
Embodiment 3
Other is with embodiment 1, and that different is Semen Cassiae 1500g in the step (1), and each refluxing extraction is 6 times in the Soxhlet extraction apparatus, and each used solvent volume is 1.5 times of cassia seed powder.Each extraction time, the best was 80 minutes; In the step (2) aqueous extract is dissolved in the distilled water of 7.5 times of volumes, water-soluble part is with n-butanol extraction 4 times, extracts volume at every turn and be 1.5 times of aqueous solution volume, and the extraction time is 20 minutes at every turn, and combining extraction liquid volatilizes solvent, mixture A.Mixture A is fully dissolved with 8 times 95% ethanol, isolate and be insoluble to 95% alcoholic acid mixture C; In the step (3) mixture C fully is dissolved in 3 times the distilled water, the solution macroporous adsorptive resins of partly flowing through, being adsorbed on significant part on the post, to adopt 95% ethanol, water to be eluted to successively colourless, collects ethanol eluate, concentrate, the ethanol elution thing.The result obtains required compound.
Claims (4)
1, a kind of method of extracting anthraquinone analog compound from study of semen cassia is characterized in that comprising the steps:
(1) study of semen cassia is clayed into power, adopt solvent branch extraction method, according to polarity by little to greatly successively with solvent hexanaphthene, chloroform, ethyl acetate, propyl carbinol, ethanol, water each refluxing extraction 4～6 times in the Soxhlet extraction apparatus, the 1.5-2.5 that each used solvent volume is the study of semen cassia powder volume doubly, each extraction time is 40-80 minute, and temperature is 60 ± 5 ℃; United extraction liquid reclaims solvent, obtains aqueous extract;
(2) aqueous extract that step (1) is obtained is dissolved in the distilled water of 5.0-10.0 times of volume, filter and remove insolubles, n-butanol extraction 4-8 time of water-soluble part, the used volume of each extraction is 0.5-1.5 a times of aqueous solution volume, each extraction time is 20-40 minute, and combining extraction liquid volatilizes solvent, the mixture that obtains is isolated and is insoluble to 95% alcoholic acid mixture with 95% dissolve with ethanol of 3.0-8.0 times of volume;
(3) the 95% alcoholic acid mixture that is insoluble to that step (2) is obtained is dissolved in the distilled water of 3-5 times of volume, the impurity of elimination indissoluble, the solution macroporous adsorptive resins of partly flowing through; Being adsorbed on significant part on the post, to adopt 95% ethanol, water to be eluted to successively colourless, collects ethanol eluate, concentrate the ethanol elution thing;
(4) the ethanol elution thing that obtains with 100～200 order silicagel column separating steps (3) adopts chloroform-methanol-water elution system;
(5) chloroform in the elution system of set-up procedure (4): the volume of methyl alcohol=4: 1, the mixture that obtains is through silica gel column chromatography, adopt ethyl acetate: the volume wash-out of 95% ethanol=4: 1.5, the mixture that obtains is further through polyamide column chromatography, methyl alcohol: the volume wash-out of water=2: 3 obtains anthraquinone analog compound II and anthraquinone analog compound III;
Adjust chloroform in the elution system: the volume of methyl alcohol=3: 1, the mixture that obtains is through silicagel column chromatography repeatedly, and adopt ethyl acetate: the volume wash-out of 95% ethanol=3-5: 1.0-2.0 obtains anthraquinone analog compound I;
Adjust chloroform in the elution system: methyl alcohol: the volume of water=3: 1: 0.1, the mixture that obtains is used methyl alcohol through polyamide column chromatography: the mixture that the volume wash-out of water=2: 3 obtains further obtains anthraquinone analog compound IV through gel filtration chromatography, water elution;
Described anthraquinone analog compound I is Schuttgelb-1-O-β-gentiobioside;
Anthraquinone analog compound II is chrysophanol-1-O-β-gentiobioside;
Anthraquinone analog compound III is rheochrysidin-8-O-β-gentiobioside;
Anthraquinone analog compound IV is chrysophanol-1-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyanoside.
2, method according to claim 1, it is characterized in that in the step (1), clay into power earlier when used Semen Cassiae uses, cross the 100-200 mesh sieve, each solvent extraction time is 55-65 minute, and the volume that at every turn extracts solvent is 2.0 times of study of semen cassia powder volume.
3, method according to claim 1 and 2 is characterized in that the extraction of propyl carbinol is at room temperature carried out in step (2), extracts volume at every turn and be 0.5 times of sample volume, and the extraction time is 25 minutes at every turn; Fully shook up, place 20 minutes after adding 95% ethanol in the mixture that obtains, precipitation is separated out partly to be and is insoluble to 95% alcoholic acid mixture.
4, method according to claim 1 is characterized in that in step (3) the macroporous adsorbent resin medium refills post after rinsing well with acetone-alcohol-water successively.
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2439925B (en) | 2006-07-10 | 2009-01-14 | Chongqing Inst Of Ecological M | Anti-obesity plant extract comprising anthraquinones and its method of preparation |
| CN102993247A (en) * | 2012-12-17 | 2013-03-27 | 中国科学院武汉植物园 | Method for separating anthraquinone ingredient of semen cassiae by low-pressure and medium-pressure preparative column |
| CN104287035A (en) * | 2014-09-30 | 2015-01-21 | 江苏奇力康皮肤药业有限公司 | Method for preparing semen cassiae carbonated beverage |
| CN109358141B (en) * | 2018-10-23 | 2021-06-11 | 北京中医药大学 | Cassia seed reference extract and preparation method and application thereof |
| CN110305496B (en) * | 2019-07-17 | 2021-02-12 | 衡水学院 | A kind of high stability cassia pigment extraction method |
| CN111072735A (en) * | 2019-12-20 | 2020-04-28 | 成都普思生物科技股份有限公司 | Anthraquinone compound extracted and separated from semen cassiae and method and application thereof |
| CN111454993B (en) * | 2020-04-15 | 2021-01-15 | 武汉森澜生物科技有限公司 | Semen cassiae fermentation product and application thereof |
| CN115389692B (en) * | 2021-05-25 | 2024-02-23 | 中化国际新材料(河北)有限公司 | Monitoring analysis method for process of preparing dye disperse yellow 65 by anthraquinone-1, 5-disulfonate |
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Non-Patent Citations (3)
| Title |
|---|
| 决明子中蒽醌类化学成分及其生物活性研究进展 陈秋冬等，中国现代应用药学杂志，第20卷第2期 2003 * |
| 决明子中蒽醌类成分提取分离研究进展 高桂霞 张会宜 刘淑萍，化学工程师，第116卷第5期 2005 * |
| 决明子中蒽醌类成分提取分离研究进展 高桂霞 张会宜 刘淑萍，化学工程师，第116卷第5期 2005;决明子中蒽醌类化学成分及其生物活性研究进展 陈秋冬等，中国现代应用药学杂志，第20卷第2期 2003 * |
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