CN100368421C - Method for picking up and separating compound of flavone being as effective content of cinquefoil, and application - Google Patents
Method for picking up and separating compound of flavone being as effective content of cinquefoil, and application Download PDFInfo
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- CN100368421C CN100368421C CNB2006100155915A CN200610015591A CN100368421C CN 100368421 C CN100368421 C CN 100368421C CN B2006100155915 A CNB2006100155915 A CN B2006100155915A CN 200610015591 A CN200610015591 A CN 200610015591A CN 100368421 C CN100368421 C CN 100368421C
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Abstract
This invention discloses a method for extracting and separating flavonoid compounds from Potentilla chinesis. The chemical formulae of the flavonoid compounds are shown in formulae 1 and 2. The method comprises: (1) pulverizing Potentilla chinesis, extracting ethanol by refluxing, filtering, incorporating the filtrates, and vacuum-evaporating to obtain an etractum; (2) dissolving the extractum in ethanol, performing polyamide column chromatographic separation, eluting with ethanol/water, collecting the elutes, and vacuum-evaporating to obtain an extractum; (3) performing C-18 column chromatographic separation under normal pressure, eluting with ethanol/water, collecting the elutes, and vacuum-evaporating to obtain the effective components 1 and 2. The flavonoid compounds can be used to manufacture drugs for treating diabetes. The polyamide and C-18 fillers in this invention can be recycled, and water and ethanol as the solvents.
Description
Technical field
The present invention relates to a kind of tormentic effective constituent chromocor compound extraction and separation method and application, belong to the Chinese medicine extracts active ingredients and separate and utilisation technology.
Background technology
The Chinese medicine tormentic, (Potentilla chinesis Ser.) 2000,2005 years pharmacopeia are all on the books
[3], cold in nature.Function clearing heat and detoxicating, cooling blood for hemostasis is arranged.Be used for dysentery, bleeding hemorrhoids, haematemesis, hemoptysis, carbuncle pyogenic infections from tumour or sore, pharyngolaryngitis, Whooping cough.Modern study shows that potentilla plants contains triterpenes, flavonoid, tannin and VITAMIN etc.Pharmacological evaluation shows that tormentic has outside the restraining effect dysentery bacterium, and there is certain restraining effect in intravital endameeba histolytica, also has analgesic activity and hepatoprotective effect.
Through the applicable cases among the people of the geographic Chinese medicine tormentic in Ji County, Tianjin is investigated, find application tormentic treatment diabetes among the people, evident in efficacy, many people use tormentic for tea-drinking treatment diabetes.
Summary of the invention
The purpose of this invention is to provide a kind of tormentic effective constituent chromocor compound extraction and separation method and application, this procedure is simple, and the flavonoid compound that is extracted has antidiabetic effect.
The present invention is realized by following technical proposals, a kind of tormentic (Potentilla chinesis Ser.) effective constituent chromocor compound, and its structural formula is shown in formula 1 and the formula 2:
The extraction and separation method of above-mentioned chromocor compound is characterized in that comprising following process:
(1) tormentic is pulverized, quality 10-12 mass concentration 70%-95% alcohol heating reflux doubly with tormentic extracted 5-7 hour, filtering filter residue, quality 10-12 mass concentration 70-95% alcohol heating reflux doubly with tormentic extracted 5-7 hour again, after so extracting three times, merging filtrate, reduction vaporization are concentrated into and soak paste;
(2) paste that step (1) is obtained mass concentration 30-50% dissolve with ethanol, separate with 100-200 purpose polyamide column chromatography, be that the elutriant of 30%, 40%, 50%, 60%, 70%, 80% and 95% alcohol-water carries out gradient elution with the ethanol volumetric concentration successively then, collect stream part of ethanol volumetric concentration 50%-70% alcohol-water wash-out, reduction vaporization is concentrated into and soaks paste;
(3) paste that step (2) is obtained separates with octadecyl bonding (C-18) reverse-phase chromatographic column under normal pressure; be that the elutriant of 50%, 60%, 70%, 80% and 95% alcohol-water carries out gradient elution with the ethanol volumetric concentration successively then; stream part of the wash-out of the elutriant of collection ethanol volumetric concentration 60%-80% alcohol-water; merge reduction vaporization and concentrate, obtain effective constituent trifolitin-3-oxygen-β-D-(6 "-trans-right-coumaric acyl)-glucopyranoside and trifolitin-3-oxygen-β-D-(6 "-cis-right-coumaric acyl)-glucopyranoside.
The application of above-mentioned trifolitin-3-oxygen-β-D-(6 "-trans-right-coumaric acyl)-glucopyranoside and trifolitin-3-oxygen-β-D-(6 "-cis-right-coumaric acyl)-glucopyranoside effective constituent is used to prepare antidiabetic oral dosage form or non-oral dosage form medicine.
The invention has the advantages that: the present invention adopts the solvent extraction extracting process to have the big technology characteristic of simple of processing capacity, the polymeric amide of use and the renewable use of anti-phase C-18 silica filler, makes solvent, economical and convenient, is easy to industrialization with water and ethanol.The anti-diabetic efficient part of making can be separately or combine with suitable vehicle etc., makes oral dosage form or non-oral dosage form (injection, sprays, patch etc.) is used to prepare the medicine for the treatment of diabetes according to ordinary method.
Embodiment
Embodiment 1
Get drying, be cut into Ji County, Tianjin product tormentic 1.2kg of 2-3 centimetre, add the 15kg70% alcohol dipping and spend the night heating and refluxing extraction 6 hours, add the 12kg95% alcohol reflux again 2 times, each 6 hours, united extraction liquid, concentrating under reduced pressure got ethanol extract 175g.With ethanol extract with 40% dissolve with ethanol, filter, polymeric amide dress post (100-200 order) with 400g carries out chromatographic separation, alcohol-water gradient elution (40%, 50%, 60%, 70%, 80% and 95% ethanol, each gradient solvent amount is 800mL), collect stream part of 50-70% ethanol elution, concentrating under reduced pressure, the medicinal extract that obtains separates with 250g (50-80 μ m) normal pressure C-18 reverse-phase chromatographic column again, alcohol-water (50%, 60%, 70%, 80% and 95% ethanol, each gradient solvent amount is 250mL) wash-out, the stream part of collecting 60% to 70% wash-out, merge reduction vaporization and concentrate, get effective constituent (compound 1 and 2) 0.35g.The high effective liquid chromatography for measuring total content is 90.5%.
Embodiment 2
Get drying, be cut into Ji County, Tianjin product Chinese medicine tormentic 2.5kg of 2-3 centimetre, mass concentration 95% alcohol dipping that adds 32kg is spent the night heating and refluxing extraction three times, each 6 hours, united extraction liquid, the ethanol extract 326g of concentrating under reduced pressure.With ethanol extract with mass concentration 50% dissolve with ethanol, filter, polymeric amide dress post (100-200 order) with 800g carries out chromatographic separation, alcohol-water gradient elution (40%, 50%, 60%, 70%, 80% and 95% ethanol, each gradient solvent amount is 1500mL, collecting the ethanol volumetric concentration is stream part of 50-60% ethanol elution, concentrating under reduced pressure, separate with the anti-phase C-18 dress of 400g (50-80 μ m) post again under the medicinal extract normal pressure that obtains, alcohol-water (50%, 60%, 70% and 95% ethanol, each gradient solvent amount is 500mL) wash-out, collect stream part of 60% to 70% wash-out, merge reduction vaporization and concentrate, get effective constituent (compound 1 and 2) 0.75g.The high effective liquid chromatography for measuring total content is 82.5%.
Embodiment 3
Get drying, be cut into Ji County, Tianjin product Chinese medicine tormentic 5kg of 2-3 centimetre, add the 60kg70% alcohol dipping and spend the night heating and refluxing extraction 6 hours, add the 50kg70% alcohol reflux again 2 times, each 6 hours, united extraction liquid, concentrating under reduced pressure got ethanol extract 595g.With ethanol extract with 50% dissolve with ethanol, filter, carry out chromatographic separation with 1500g polymeric amide dress post (60-100 order), alcohol-water gradient elution (50%, 60%, 70%, 80% and 95% ethanol, each gradient solvent amount is 3000mL), collect stream part of 50-60% ethanol elution, concentrating under reduced pressure, the medicinal extract that obtains separates with 650g normal pressure C-18 reverse-phase chromatographic column again, alcohol-water (50%, 60%, 70%, 80% and 95% ethanol, each gradient solvent 800mL) wash-out, the stream part of collecting 60% to 80% wash-out, merge reduction vaporization and concentrate, get effective constituent (compound 1 and 2) 2.45g.The high effective liquid chromatography for measuring total content is 72.5%.
Pharmacological evaluation
1 experiment material
Potentilla flavone (compound 1 and 2, mass ratio 2: 1, this laboratory self-control, specific embodiment 1).Tetraoxypyrimidine (Sigma company), phenformin hydrochloride tablet, blood sugar test kit (the middle north control bio tech ltd of giving birth to), low speed autobalancing centrifuge (Anxin County, Hebei province whizzer factory).UV-240 ultraviolet spectrophotometer (day island proper Tianjin), (animal housing of Medical University Of Tianjin provides Kunming mouse, ♀ ♂ dual-purpose, 24 ± 2g).
2 methods
(1) foundation of alloxan diabetes mouse model with the about 12h of mouse fasting (can't help water) after, the tetraoxypyrimidine solution (15mg/mL) of the new configuration of tail vein injection, dosage is 75mg/kg (0.05mL/10g).Fasting again (can't help water) 12h behind 60h, eye socket is got blood.Surveying blood glucose value with glucose oxidase method, is qualified tissue of experimental diabetic mice model greater than 11.1mmol/L.
(2) 50 tablets of phenformins (25mg/ sheet) are got in the preparation of positive control solution, grind, and with the dissolved in distilled water that boiled, are made into the aqueous solution of 7.5mg/mL.
(3) effect experiment of chromocor compound
Choose normal mouse, set up hyperglycemia model.Select qualified mouse, evenly be divided into 5 groups, 11 every group by blood glucose value.Give the effective constituent that specific embodiment 1 is extracted respectively, dosage group 1 (0.4mg/kg), dosage group 2 (0.1mg/kg), model control group and phenformin positive control solution (75mg/kg).Water 12h is can't help in fasting before the continuous irrigation stomach 15 days, last administration, and broken end was got blood after water 1h was can't help in fasting after the administration, surveyed blood glucose value with the GOD method.
3 results
The influence of table 1 potentilla flavone compound 1 and 2 pairs of alloxan diabetes mouse blood sugars
* and model group be p＜0.01 relatively
Dosage group 1 is compared in model control group with 2 experimental result, has significant difference, p＜0.01, and its action intensity and positive controls relatively are better than phenformin hydrochloride.
Claims (2)
1. tormentic effective constituent chromocor compound extraction and separation method, the active chemical of described tormentic, its structural formula are shown in formula 1 and the formula 2:
The extraction and separation method of above-mentioned chromocor compound is characterized in that comprising following process:
(1) tormentic is pulverized, quality 10-12 mass concentration 70%-95% alcohol heating reflux doubly with dry tormentic extracted 5-7 hour, filtering filter residue, quality 10-12 mass concentration 70-95% alcohol heating reflux doubly with tormentic extracted 5-7 hour again, after so extracting three times, merging filtrate, reduction vaporization are concentrated into and soak paste;
(2) paste that step (1) is obtained mass concentration 30-50% dissolve with ethanol, separate with 100-200 purpose polyamide column chromatography, be that the elutriant of 30%, 40%, 50%, 60%, 70%, 80% and 95% alcohol-water carries out gradient elution with the ethanol volumetric concentration successively then, collect stream part of ethanol volumetric concentration 50%-70% alcohol-water wash-out, reduction vaporization is concentrated into and soaks paste;
(3) paste that step (2) is obtained is that the C-18 reverse-phase chromatographic column separates with octadecyl bonding reverse-phase chromatographic column under normal pressure; be 50% with the ethanol volumetric concentration successively then; 60%; 70%; the elutriant of 80% and 95% alcohol-water carries out gradient elution; stream part of the wash-out of the elutriant of collection ethanol volumetric concentration 60%-80% alcohol-water; merge reduction vaporization and concentrate, obtain effective constituent trifolitin-3-oxygen-β-D-(6 " trans-right-coumaric acyl)-glucopyranoside and trifolitin-3-oxygen-β-D-(6 "-cis-right-coumaric acyl)-glucopyranoside.
2. by the application of the described tormentic effective constituent of claim 1 chromocor compound, this compound is used to prepare antidiabetic oral dosage form or non-oral dosage form medicine.
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| CNB2006100155915A CN100368421C (en) | 2006-09-06 | 2006-09-06 | Method for picking up and separating compound of flavone being as effective content of cinquefoil, and application |
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| CNB2006100155915A CN100368421C (en) | 2006-09-06 | 2006-09-06 | Method for picking up and separating compound of flavone being as effective content of cinquefoil, and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101028165B1 (en) * | 2010-08-25 | 2011-04-08 | 주식회사 지앤드에이엠티 | The fixing instrument for a pipe |
| WO2012061958A1 (en) | 2010-11-12 | 2012-05-18 | 天津医科大学 | Flavone derivatives and their preparative method and medical use |
| CN104861020B (en) * | 2015-06-14 | 2017-05-17 | 海南医学院 | Phenylpropanoid glycoside compound, and extraction method and application thereof |
| CN104922196B (en) * | 2015-06-30 | 2019-04-26 | 广西壮族自治区中医药研究院 | The preparation of small pagodatree flower general flavone extract and quality determining method |
| CN105001286A (en) * | 2015-07-23 | 2015-10-28 | 昆明理工大学 | Method for extracting tiliroside from Tibetan drug scindapsus aureus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO102612A2 (en) * | 1988-12-22 | 1991-10-30 | Institutul De Medicina Si Farmacie, Cluj-Napoca, Judetul Cluj, Ro | Vegetal extract for cosmetic use |
| WO2005068484A1 (en) * | 2004-01-19 | 2005-07-28 | Merck Patent Gmbh | Flavonoid complexes comprising cyclodextrins |
-
2006
- 2006-09-06 CN CNB2006100155915A patent/CN100368421C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO102612A2 (en) * | 1988-12-22 | 1991-10-30 | Institutul De Medicina Si Farmacie, Cluj-Napoca, Judetul Cluj, Ro | Vegetal extract for cosmetic use |
| WO2005068484A1 (en) * | 2004-01-19 | 2005-07-28 | Merck Patent Gmbh | Flavonoid complexes comprising cyclodextrins |
Non-Patent Citations (4)
| Title |
|---|
| 国产委陵菜属植物资源. 张勇，王一峰.西北师范大学学报（自然科学版），第34卷第1期. 1998 * |
| 委陵菜化学成份的研究. 陈芳群.华西药学杂志，第4卷第1期. 1989 * |
| 委陵菜化学成分的研究. 沈阳等.中药材，第29卷第3期. 2006 * |
| 委陵菜抗菌活性成分的研究. 苏广双等.沈阳药学院学报，第3卷第3期. 1986 * |
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