CN1440979A - Steroid saponin from sealwort as Chinese medicine material and its medicinal use and prepn process - Google Patents
Steroid saponin from sealwort as Chinese medicine material and its medicinal use and prepn process Download PDFInfo
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Abstract
The present invention relates to steriod saponin from sealwort as Chinese medicine material and its medical use and preparation process. It has the effects of improving cerebral function and lowering blood sugar level. It is prepared with sealwort root powder and through water extraction, concentration, chloroform extraction, macroporous resin adsorption, dilute alcohol washing to eliminate impurity, alcohol elution to obtain alcohol solution, recovering solvent to obtain steriod saponin, silica gel chromatography to separate, re-crystallization, and HPLC chromatography to obtain triterpenoid saponin monomer. The present invention is suitable for industrial production and has the functions of improving learning and memory capacity of early stage senile dementia.
Description
Technical field:
The present invention relates to the preparation of the triterpene saponin componds in the stem and leaf of Radix Panacis Quinquefolii in the medical technical field, exactly it is steroidal saponin and medicinal use and the preparation method in a kind of Chinese medicine sealwort.
Background technology:
The Chinese medicine sealwort is Liliaceae Polygonatum per nnial herb sealwort (Polygonatumsibiricum) rhizome, is distributed in all parts of the country, wherein mainly is distributed in ground such as three provinces in the northeast of China, Inner Mongol, Hebei, Shaanxi, Shandong.Former plant of the sealwort that records of Chinese Pharmacopoeia (nineteen ninety-five version) has 3 kinds, that is: sealwort Polygonatum sibiricum, capsule silk sealwort (David's-harp) Polygonatum cyrtonema and Yunnan sealwort Polygonatum kingianum.Beginning is stated from " Mingyi Bielu ", classifies as top gradely, and property is flat, flavor is sweet, nontoxic, return spleen, lung, kidney channel, can boosting qi and nourishing yin, invigorating the spleen, moistening lung, kidney-nourishing, and be one of traditional Chinese medical science common drug.The chemical constitution study of Chinese medicine sealwort (Polygonatum sibiricum) seldom, rarely seen report about alkaloid and polysaccharide, Shang Weijian is to the research bibliographical information of its steroidal saponin constituents.Pharmacological research shows that sealwort has: 1, to the improvement effect of cardiovascular systems; 2, to immune regulating effect; 3, anti-aging effects; 4, antitumor action; 5, other pharmacological action such as antibacterial, antimycotic.China Patent No.: 93106042.7 disclose the patent of invention that a kind of name is called " sealwort beverage and manufacture method thereof ", it is a kind of health promoting beverage, China Patent No.: 98121819.9 disclose the patent of invention that a kind of name is called " the sweet glycan capsule of sealwort polysaccharide konjaku sugar ", though also having, it delays senility, improve memory, the effect of regulating blood fat, but it also just utilizes polygonatum polysaccharide, China Patent No.: 02102167.8 discloses the patent of invention that a kind of name is called " method of extracting polygonatum polysaccharide in the Chinese medicine sealwort ", and it is a kind of novel process of extracting polygonatum polysaccharide.
Summary of the invention:
The object of the present invention is to provide steroidal saponin constituents in the Chinese medicine sealwort and preparation method thereof, and clearly proposed it and improved the learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) due to the disordered brain function and the medicinal use of lowering blood glucose, and provide a kind of science stable, be applicable to the method for preparing the total steroid saponin constituents of suitability for industrialized production.
Steroidal saponin constituents provided by the invention be meant have following general formula (1), 1 β shown in general formula (2) or the general formula (3), 12 Alpha-hydroxy spirostanol saponins, Furost saponine shown in the general formula (4), the courage steroid saponin shown in the general formula (5), and the new steroid oside compound shown in the general formula (6).
R in the formula
1Be hydrogen or glycosyl (containing 1～5 glycosyl), R
2And R
3Be hydrogen, hydroxyl or glycosyl (containing 1～2 glycosyl), above indication glycosyl is meant glucopyranosyl, xylopyranose grain base, arabopyranose base, arabinofuranosyl, rhamnopyranosyl, galactopyranose, pyrans furan glycosyl, sugar chain can be straight or branched, and mode of connection can be (1-2), (1-3), (1-4) or (1-6) connection.
The medicinal use of above-mentioned total steroid saponin and simplification compound is learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) and the lowering blood glucose effect that improves due to the disordered brain function.The above-claimed cpd toxic side effect is little, is suitable for medicinal use.
The extracting method of above-mentioned total steroid saponin or simplification compound is: Solomonseal Rhizome through water (rare alcohol) decoct (or diafiltration), macroporous resin and ion exchange resin desugar decolour total saponins, make respectively through column chromatography and HPLC method again.
The preparation method of above-mentioned total steroid saponin and simplification compound is characterized in that comprising following four steps:
A: root of Rhizoma Polygonati powder water extraction: soak, the ratio of medicinal material and water is 1: 2～10, calorifies under (room temperature is to used boiling point of liquid) condition, and each 0.5～10 hour, extract 1～10 time, merge each extracting solution, be concentrated into 2～100 times of medicinal material;
B: the sealwort extracting solution concentrates, and concentrated aqueous solution is used n-butanol extraction after chloroform extraction is removed low polar impurity, reclaims propyl carbinol and gets n-butyl alcohol extract;
C: extracting solution with rare alcohol (0～40%) flush away impurity, gets alcoholic solution with 20%～100% pure liquid wash-out through macroporous resin adsorption again, reclaims solvent and gets total steroid saponin;
D: separate moving phase: 1) chloroform/methanol (0～100%) gradient elution through silica gel chromatography; 2) chloroform-methanol-water (65: 35: 10), following phase); 3) propyl carbinol-ethyl acetate-water (phase on 4: 1: 5):
E: gained stream part is through recrystallization, and the HPLC chromatogram: octadecyl silane (ODS) is a stationary phase, and methyl alcohol (second eyeball, tetrahydrofuran (THF))/water (10～95%) is moving phase, and ultraviolet 192～350nm detects, and gets each triterpenoid saponin constituents monomer.
Sealwort improve learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) effect due to the disordered brain function, do not see bibliographical information so far, under pharmacology is followed the tracks of, through to the systematic study of sealwort chemical ingredients, find that sealwort total steroid saponin and monomer steroidal saponin have the effect that improves the learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) due to the disordered brain function.Its result is as follows:
1,400mg/kg sealwort total steroid saponin and monomer steroidal saponin can obviously improve the normal mouse learning capacity;
2,400mg/kg sealwort total steroid saponin and monomer steroidal saponin are to the mouse memory acquired disturbance effect of having clear improvement due to the Scopolamine.
3, yellow total steroid saponin of 100mg/kg, 400mg/kg and monomer steroidal saponin can obviously prolong the survival time that bilateral ligation causes the acute cerebral ischemia mouse.
4,0.5mg/ml, 2.5mg/ml sealwort total steroid saponin and monomer steroidal saponin can significantly suppress the generation of the MDA of rat cerebral tissue.
5,400mg/kg sealwort total steroid saponin and monomer steroidal saponin can obviously suppress the blood glucose value of the hyperglycemia mouse that suprarenin brings out.
Advantage of the present invention is, steroidal saponin constituents in the Chinese medicine sealwort and preparation method thereof is provided, and the learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) that improves due to the disordered brain function and the medicinal use of lowering blood glucose are arranged, and provide a kind of science stable, be applicable to the method for preparing the total steroid saponin composition of suitability for industrialized production.Use extracting method of the present invention, the high purity total triterpene saponins and the monomer triterpenoid saponin of the impurity such as a large amount of albumen, carbohydrate, starch that can be removed.
Description of drawings:
Fig. 1 is the separation process figure of 11 monomeric compounds among the present invention.
Embodiment:
Embodiment:
After sealwort rhizome (30kg) is pulverized, with water extraction 3 times, each 2 hours, extract concentrate aqueous extract, thin up extracts respectively with chloroform, propyl carbinol successively and obtains the polarity distinct portions then.After propyl carbinol part handled with macroporous resin column chromatography the sealwort total steroid saponin.The sealwort total steroid saponin utilizes silica gel column chromatography, and methods such as recrystallization and Rp18-HPLC therefrom obtain 11 monomeric compounds.
The evaluation of part of compounds:
Compound 2: huangjinoside A (huangjinoside A), white powder, mp250-252 ℃ (MeOH).
Compound 3: huangjinoside B (huangjinoside B), white powder, mp256-259 ℃ (MeOH).
Compound 4: huangjinoside C (huangjinoside C), white powder, mp291-293 ℃ (MeOH).
Claims (4)
1, the steroidal saponin in the Chinese medicine sealwort and medicinal use and preparation method, it is characterized in that: the structural formula of steroidal saponin is in the Chinese medicine sealwort: a: 1 β shown in general formula (1), general formula (2) or the general formula (3), 12 Alpha-hydroxy spirostanol saponins:
R in the formula
1Be hydrogen or glycosyl (containing 1～5 glycosyl), R
2And R
3Be hydrogen, hydroxyl or glycosyl (containing 1～2 glycosyl), above indication glycosyl is meant that glucopyranosyl, xylopyranosyl, arabopyranose base, arabinofuranosyl, rhamnopyranosyl, galactopyranose, pyrans furan glycosyl, sugar chain can be straight or branched, and mode of connection can be (1-2), (1-3), (1-4) or (1-6) connection;
B: the Furost saponine shown in the general formula (4):
R in the formula
1Be hydrogen or glycosyl (containing 1～5 glycosyl), above indication glycosyl is meant that glucopyranosyl, xylopyranosyl, arabopyranose base, arabinofuranosyl, rhamnopyranosyl, galactopyranose, pyrans furan glycosyl, sugar chain can be straight or branched, and mode of connection can be (1-2), (1-3), (1-4) or (1-6) connection;
C: the courage steroid saponin shown in the general formula (5):
R in the formula
1Be hydrogen or glycosyl (containing 1～5 glycosyl), above indication glycosyl is meant that glucopyranosyl, xylopyranosyl, arabopyranose base, arabinofuranosyl, rhamnopyranosyl, galactopyranose, pyrans furan glycosyl, sugar chain can be straight or branched, and mode of connection can be (1-2), (1-3), (1-4) or (1-6) connection;
D: the steroid oside compound shown in the general formula (6):
R
1Be hydrogen or glycosyl (containing 1～5 glycosyl), above indication glycosyl is meant that glucopyranosyl, xylopyranosyl, arabopyranose base, arabinofuranosyl, rhamnopyranosyl, galactopyranose, pyrans furan glycosyl, sugar chain can be straight or branched, and mode of connection can be (1-2), (1-3), (1-4) or (1-6) connection.
2, steroidal saponin and medicinal use and the preparation method in the Chinese medicine sealwort according to claim 1 is characterized in that the preparation method comprises the steps:
A, root of Rhizoma Polygonati powder water extraction: soak, the ratio of medicinal material and water is 1: 2～10, calorify under (room temperature is to used boiling point of liquid) condition, and each 0.5～10 hour, extract 1～10 time, merge each extracting solution, be concentrated into 2～100 times of medicinal material;
B, sealwort extracting solution concentrate, and concentrated aqueous solution is used n-butanol extraction after chloroform extraction is removed low polar impurity, reclaim propyl carbinol and get n-butyl alcohol extract;
C, extracting solution with rare alcohol (0～40%) flush away impurity, get alcoholic solution with 20%～100% pure liquid wash-out through macroporous resin adsorption again, reclaim solvent and get total steroid saponin;
D, separate moving phase: 1) chloroform/methanol (0～100%) gradient elution through silica gel chromatography; 2) chloroform-methanol-water (65: 35: 10, following phase); 3) propyl carbinol-ethyl acetate-water (phase on 4: 1: 5):
E, gained stream part are through recrystallization, and the HPLC chromatogram: octadecyl silane (ODS) is a stationary phase, and methyl alcohol (second eyeball, tetrahydrofuran (THF))/water (10～95%) is moving phase, and ultraviolet 192～350nm detects, and gets each triterpenoid saponin constituents monomer.
3, steroidal saponin and medicinal use and the preparation method in the Chinese medicine sealwort according to claim 2, it is characterized in that: the extracting solution among the step a can be Different concentrations of alcohol or methyl alcohol, concentration 0～95%; Extracting method can be to decoct or diafiltration; Can use ethanol ethyl ester abstraction impurity removal matter earlier among the step b; Absorption macroporous resin among the step c, available the moon (or sun) ion exchange resin; Stationary phase can be used aluminum oxide, gac, Sephaelex LH-20 etc. in the steps d; Step e can use positive HPLC, is stationary phase with silica gel, moving phase: 1) chloroform-methanol-water, 2) chloroform-methanol, 3) ethyl acetate-acetone, and other organic solvents.
4, steroidal saponin and medicinal use and the preparation method in the Chinese medicine sealwort according to claim 1, it is characterized in that: 1 β shown in general formula (1), general formula (2) or the general formula (3), 12 Alpha-hydroxy spirostanol saponins, Furost saponine shown in the general formula (4), courage steroid saponin shown in the general formula (5), and the steroid oside compound shown in the general formula (6) improves the learning memory injury (comprising that the dull-witted patient of early-stage senile improves learning and memory) due to the disordered brain function and the medicinal use of lowering blood glucose effect.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101837091A (en) * | 2010-03-17 | 2010-09-22 | 安徽师范大学 | Process for continuously extracting polygonatum saponin and polygonatum polysaccharose |
| CN101191788B (en) * | 2006-11-24 | 2011-07-27 | 天津药业研究院有限公司 | Steroid compounds analytical method |
| WO2016192450A1 (en) * | 2015-06-03 | 2016-12-08 | 上海家化联合股份有限公司 | Preparation and application of polygonatum sibiricum pectin-type polysaccharide |
| CN106501409A (en) * | 2016-10-26 | 2017-03-15 | 王喜军 | A kind of urine metabolism mark authentication method based on senile dementia |
| CN110507662A (en) * | 2019-08-26 | 2019-11-29 | 江西省药品检验检测研究院 | A kind of rhizoma polygonati steroid sapogenin and the preparation method and application thereof |
| CN117069788A (en) * | 2023-08-17 | 2023-11-17 | 中南民族大学 | Furosestanol type steroid saponin compounds, preparation method and application thereof |
-
2003
- 2003-04-04 CN CN 03111357 patent/CN1440979A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101191788B (en) * | 2006-11-24 | 2011-07-27 | 天津药业研究院有限公司 | Steroid compounds analytical method |
| CN101837091A (en) * | 2010-03-17 | 2010-09-22 | 安徽师范大学 | Process for continuously extracting polygonatum saponin and polygonatum polysaccharose |
| WO2016192450A1 (en) * | 2015-06-03 | 2016-12-08 | 上海家化联合股份有限公司 | Preparation and application of polygonatum sibiricum pectin-type polysaccharide |
| CN106501409A (en) * | 2016-10-26 | 2017-03-15 | 王喜军 | A kind of urine metabolism mark authentication method based on senile dementia |
| CN106501409B (en) * | 2016-10-26 | 2019-09-24 | 王喜军 | A kind of urine metabolism marker identification method based on senile dementia |
| CN110507662A (en) * | 2019-08-26 | 2019-11-29 | 江西省药品检验检测研究院 | A kind of rhizoma polygonati steroid sapogenin and the preparation method and application thereof |
| CN110507662B (en) * | 2019-08-26 | 2023-10-13 | 江西省药品检验检测研究院 | Polygonatum sibiricum steroidal sapogenin and preparation method and application thereof |
| CN117069788A (en) * | 2023-08-17 | 2023-11-17 | 中南民族大学 | Furosestanol type steroid saponin compounds, preparation method and application thereof |
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