CN101469014B - Novel compound and separation method thereof - Google Patents
Novel compound and separation method thereof Download PDFInfo
- Publication number
- CN101469014B CN101469014B CN2007103043460A CN200710304346A CN101469014B CN 101469014 B CN101469014 B CN 101469014B CN 2007103043460 A CN2007103043460 A CN 2007103043460A CN 200710304346 A CN200710304346 A CN 200710304346A CN 101469014 B CN101469014 B CN 101469014B
- Authority
- CN
- China
- Prior art keywords
- chloroform
- methanol
- compound
- wash
- gradient elution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Steroid Compounds (AREA)
Abstract
The invention discloses a new compound of 3,16,20,22,23,25-hexahydroxy ergostane and a separation method thereof. The chemical structural formula of the compound of 3,16,20,22,23,25-hexahydroxy ergostane is shown by the right formula. Experimental results show that the compound of 3,16,20,22,23,25-hexahydroxy ergostane has the HMG-CoA reductase inhibiting effect.
Description
Technical field
The present invention relates to a kind of new compound and separation method thereof, particularly a kind of new compound 3,16,20,22,23,25-hexahydroxy-ergot steroid and separation method thereof.
Background technology
Be rich in the series natural statin substance in the XUEZHIKANG JIAONANG, comprise monacolin K (lovastatin), monacolin K alcohol acid sodium (acid, open loop type), monacolin K lactone dehydrate, monacolin L, monacolin J lactone and dehydrate etc., most of compositions all have the lipopenicillinase activity.Also contain isoflavones, sterols material, 20 seed amino acids, unsaturated fatty acids and various trace elements in the XUEZHIKANG JIAONANG.Isoflavones components mainly comprises genistein, daidzein, glycitein, and wherein free isoflavone content is about 0.045%.Sterol content in the XUEZHIKANG JIAONANG is 0.3%, comprising ergosterol, Stigmasterol and Sitosterol etc.The ergosterol chemical name is 24 Beta-methyl cholesterol-5,7 alkene-3 Beta-hydrocarbyl-s.The peroxidation ergosterol that contains in the XUEZHIKANG JIAONANG also can suppress the growth of MCF-7 human breast carcinoma and the strain of Walder256 sarcoma cell, and people's liver cancer PLC/PRF5 and KB cell are also had restraining effect; Have anti-inflammatory, anticomplement, immunosuppression and promotion platelet aggregation isoreactivity in addition.Have glycine, proline(Pro), Serine, aspartic acid, L-glutamic acid, arginine, Histidine, taurine, γ-An Jidingsuan 20 seed amino acid compositions such as (GABA) in the XUEZHIKANG JIAONANG.Contain a large amount of fatty acid components in the XUEZHIKANG JIAONANG.SciFinder (" U.S. chemical abstract (CA) network data base " by retrieval, 1907-2007.9), MEDLINE CD-ROM (" U.S. general family medicine document data of optical disk storehouse ", 1966-2007.6), PubMed (" world medicine bibliographic data base ", 2007-2007.9) and " CBMdisc " (CBMdisc, 1978-2007.6), " Chinese CMCC " (CMCC, 1994-2007.9), CJFD (CNKI, 1994-2007.9), do not see compound report new in the XUEZHIKANG JIAONANG both at home and abroad.
Summary of the invention
One object of the present invention is to disclose a kind of new compound; Another object of the present invention is to disclose the separation method of this new compound.
The present invention seeks to be achieved through the following technical solutions:
A kind of new compound, its chemical structural formula is as follows:
3,16,20,22,23, the physico-chemical property of 25-hexahydroxy-ergot steroid is: white powder, specific optical rotation are-126.8 °, and fusing point is 135-137 ℃.
New compound 3,16,20,22,23 of the present invention, the separation method of 25-hexahydroxy-ergot steroid is:
Get XUEZHIKANG JIAONANG content 1000-3000 weight part, sherwood oil, chloroform, methyl alcohol with 2-6 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 20-40 minute, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get silica gel column chromatography on the 200-300 weight part of C position,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.040-0.055 weight part with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, and respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient elution carried out half preparation purifying, obtains purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
The separation method of new compound of the present invention is preferably:
Get XUEZHIKANG JIAONANG content 2000 weight parts, sherwood oil, chloroform, methyl alcohol with 4 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 30 minutes, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get silica gel column chromatography on 250 weight parts of C position,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.047 weight part with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, and respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient elution carried out half preparation purifying, obtains purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
Weight part/parts by volume described in the separation method wherein of the present invention is g/ml.
The present invention has extracted a kind of new compound in the XUEZHIKANG JIAONANG, and found through experiments this compound and have HMG-CoA reductase enzyme restraining effect.
Experiment and embodiment are used to further specify but are not limited to the present invention below.
The experiment of experimental example 1 HMG-CoA reductase active
With embodiment 1 resulting this new compound 3,16,20,22,23,25-hexahydroxy-ergot steroid is with 75% dissolve with ethanol, and concentration is 2mg/ml; Cumulative volume is 200 μ l in the mensuration system, the concentration of each composition is: Repone K 200mM, potassium primary phosphate 160mM, ethylenediamine tetraacetic acid (EDTA) 4mM, dithiothreitol (DTT) 10mM, the concentration of two substrate Reduced nicotinamide-adenine dinucleotides and 3-hydroxy-3-methylglutaryl-coenzyme A is respectively 200 μ M and 50 μ M, pH6.8, enzyme add 20 μ L, and enzyme inhibitors adds 5 μ l, control group adds 5 μ l75% ethanol, is detecting OD under 37 ℃ of conditions on the Versamax microplate reader
340Dynamic change.By detecting OD
340The speed (representing with slope value) that descended in 5 minutes is estimated the power of HMG-CoA reductase activity, and then estimates enzyme inhibitors and suppress active power, the results are shown in Table 1.
Table 1: enzyme inhibitors suppresses the activity experiment form
| The sample title | Inhibitor concentration (mg/ml) | Inhibitor volume (μ l) | Final concentration (μ g/ml) | Slope | Inhibiting rate (%) |
| Blank (hexahydroxy-ergosterol) | ---- | ---- | ---- | 17.07 | ---- |
| The hexahydroxy-ergosterol | 2 | 5 | 50 | 14.7 | 13.9 |
| Ergosterol | 2 | 5 | 50 | 15.89 | 6.9 |
Conclusion: new compound 3,16,20,22,23,25-hexahydroxy-ergot steroid has HMG-CoA reductase enzyme restraining effect.
Following embodiment all can realize the effect of above-mentioned experimental example.
Embodiment 1:
Get XUEZHIKANG JIAONANG content 2000g, sherwood oil, chloroform, methyl alcohol with 4 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 30 minutes, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get C position 250g and go up silica gel column chromatography,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.047g with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient) wash-out, carry out half preparation purifying, obtain purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
Embodiment 2:
Get XUEZHIKANG JIAONANG content 1500g, sherwood oil, chloroform, methyl alcohol with 6 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 20 minutes, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get C position 300g and go up silica gel column chromatography,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.042g with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient) wash-out, carry out half preparation purifying, obtain purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
Embodiment 3:
Get XUEZHIKANG JIAONANG content 2500g, sherwood oil, chloroform, methyl alcohol with 2 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 40 minutes, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get C position 200g and go up silica gel column chromatography,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.053g with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient) wash-out, carry out half preparation purifying, obtain purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
Claims (5)
1. compound is characterized in that the chemical structural formula of this compound is:
2. medicine is characterized in that this medicine contains the compound of following structural formula:
3. the separation method of compound as claimed in claim 1 is characterized in that this method is:
Get XUEZHIKANG JIAONANG content 1000-3000 weight part, sherwood oil, chloroform, methyl alcohol with 2-6 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 20-40 minute, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get silica gel column chromatography on the 200-300 weight part of C position,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.040-0.055 weight part with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; Alkyl linked with C-18 is stationary phase mutually, and respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient elution carried out half preparation purifying, obtains purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
4. the separation method of compound as claimed in claim 2 is characterized in that this method is:
Get XUEZHIKANG JIAONANG content 2000 weight parts, sherwood oil, chloroform, methyl alcohol with 4 times of weight of XUEZHIKANG JIAONANG content is that solvent supersonic extracts successively, every kind of solvent is distinguished supersound extraction 3 times, each 30 minutes, united extraction liquid, reclaim solvent, get petroleum ether part P, chloroform extract C, methyl alcohol position M;
Get silica gel column chromatography on 250 weight parts of C position,, get pure chloroform wash-out portion C-I, 95: 5 chloroform-methanol wash-out portion C-II, 90: 10 chloroform-methanol wash-out portion C-III, pure methanol-eluted fractions portion C-IV with the chloroform-methanol gradient elution;
Get C-III part respectively with 90: 10,80: 20,70: 30,50: 50 chloroform-methanol gradient elution wherein obtained new compound crude product 0.047 weight part with 80: 20 chloroform-methanol wash-out parts through silica gel column chromatography repeatedly; With C-18 alkyl linked be mutually stationary phase respectively with 70: 30,80: 20,90: 10,100: 0 methanol-water gradient elution carried out half preparation purifying, obtains purity and be 98% new compound 3,16,20,22,23, the pure product of 25-hexahydroxy-ergot steroid.
5. the application of compound as claimed in claim 1 in the medicine of preparation HMG-CoA reductase inhibitor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007103043460A CN101469014B (en) | 2007-12-27 | 2007-12-27 | Novel compound and separation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007103043460A CN101469014B (en) | 2007-12-27 | 2007-12-27 | Novel compound and separation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101469014A CN101469014A (en) | 2009-07-01 |
| CN101469014B true CN101469014B (en) | 2011-06-15 |
Family
ID=40826844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007103043460A Active CN101469014B (en) | 2007-12-27 | 2007-12-27 | Novel compound and separation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101469014B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011003284A1 (en) * | 2009-07-09 | 2011-01-13 | 北京北大维信生物科技有限公司 | Compound and preparation method and use thereof |
| CN103172693B (en) * | 2011-12-26 | 2016-01-27 | 北京北大维信生物科技有限公司 | A kind of sterol derivative, Preparation Method And The Use |
| CN103211822B (en) * | 2012-01-18 | 2017-09-22 | 北京北大维信生物科技有限公司 | A kind of purposes of the suppression lipase of sterol derivative |
| SG11201403618PA (en) | 2011-12-26 | 2014-09-26 | Univ Beijing Peking Wbl Biotech Co Ltd | A sterol derivative and preparation method and uses thereof |
| CN113563404B (en) * | 2020-04-28 | 2024-03-12 | 华东师范大学 | Process for preparing cholic acid derivatives |
-
2007
- 2007-12-27 CN CN2007103043460A patent/CN101469014B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| 李 惠等.HPLC测定地黄中麦角甾苷的含量.《中国中药杂志》.2006,第31卷(第10期),822-824. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101469014A (en) | 2009-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101469014B (en) | Novel compound and separation method thereof | |
| EP3511064A1 (en) | Method for preparing high-purity cannabidiol | |
| Choodej et al. | Inhibition of TNF-α-induced inflammation by sesquiterpene lactones from Saussurea lappa and semi-synthetic analogues | |
| Chien et al. | Secondary metabolites from the root of Ehretia longiflora and their biological activities | |
| ES2191481T3 (en) | METHOD FOR EXTRACTION WITH HIGH PERFORMANCE OF PACLITAXEL FROM MATERIAL THAT CONTAINS PACLITAXEL. | |
| Li et al. | Antiplatelet aggregation activity of diterpene alkaloids from Spiraea japonica | |
| Zheng et al. | Isomerization of astilbin and its application for preparation of the four stereoisomers from Rhizoma Smilacis Glabrae | |
| Cao et al. | Isolation of anti-tumor compounds from the stem bark of Zanthoxylum ailanthoides Sieb. & Zucc. by silica gel column and counter-current chromatography | |
| CN106278877A (en) | One class novel structure sesquiterpenoid and the application in preparing anti-inflammatory drug thereof | |
| CN103339121B (en) | A kind of compound, Preparation Method And The Use be separated from red colouring agent for food, also used as a Chinese medicine | |
| JP2011525481A5 (en) | ||
| JPH08157347A (en) | External preparation for skin whitening | |
| CN101676281A (en) | Benzo macrolide compound (3R)- des-O-methyllasiodiplodin, its derivatives and preparation method and use | |
| CN104231032A (en) | Method for separating tripdiolide from Tripterygium Wilfordii Hook F leaves | |
| CN101942003A (en) | Compound and preparation method thereof | |
| KR100609765B1 (en) | Agent for lowering prolactin | |
| CN101982466B (en) | Method for extracting isoflavonoids compound in all-grass of Twining Rhynchosia with ionic liquid | |
| CN102086183B (en) | Method for extracting and separating statins substance | |
| CN104370931A (en) | New flavone compound as well as preparation method and application thereof | |
| Lutsky et al. | Inhibition of enzymatic reduction of Δ14‐double bond of 5α‐cholesta‐8, 14‐dien‐3β‐ol and 5α‐cholesta‐7, 14‐dien‐3β‐ol by AY‐9944 | |
| CN104140391A (en) | Method for separating and purifying highly pure Euphorbia factor from moleplant seed | |
| Mei et al. | Optimization of ultrasound-assisted extraction of polyphenols from Xanthoceras sorbifolia husks and their determination using HPLC | |
| CN111548255B (en) | Diterpenoid compounds in taxus chinensis, preparation method thereof and application thereof in pharmacy | |
| CN105348338A (en) | Method for extracting and separating paederosidic acid from Saprosma merrillii Lo | |
| CN102020624A (en) | Method for extracting coumarin type compound from Chimonanthus salicifolius by using surfactant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |