CN101747400B - Lanostane type triterpenoid with anti-tumor activity, preparation method and application - Google Patents
Lanostane type triterpenoid with anti-tumor activity, preparation method and application Download PDFInfo
- Publication number
- CN101747400B CN101747400B CN200810184588A CN200810184588A CN101747400B CN 101747400 B CN101747400 B CN 101747400B CN 200810184588 A CN200810184588 A CN 200810184588A CN 200810184588 A CN200810184588 A CN 200810184588A CN 101747400 B CN101747400 B CN 101747400B
- Authority
- CN
- China
- Prior art keywords
- lanostane
- formula
- water
- type triterpenoid
- compound
- 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.)
- Expired - Fee Related
Links
Images
Abstract
The invention discloses lanostane type triterpenoid with anti-tumor activity, a preparation method and the application of the lanostane type triterpenoid. The preparation method includes the following steps: ganoderma mycelium or an ethanol extract of sporocarp is prepared; the ganoderma mycelium or an ethanol extractum of the sporocarp is repeatedly extracted by petroleum ether after being dispersed by water, and is then extracted by ethyl acetate so as to obtain an ethyl acetate extract; the ethyl acetate extract is repeatedly separated by normal phase, opposite phase and gel column chromatography so as to obtain three parts; by utilizing the HPLC (high performance liquid chromatography), elution is carried out respectively by acetonitrile, methanol and water, and then the lanostane type triterpenoid is obtained through decompression and distillation drying after corresponding components are collected. Ganoderma sporocarp or fermented mycelium is separated to obtain 5 new lanostane derivants; in terms of the bioactivity, the newly-separated 5 lanostane derivants can effectively restrain proliferation of tumor cells and have excellent anti-tumor activity; therefore, the lanostane type triterpenoid in the invention can be clinically applied as an anti-tumor agent.
Description
Technical field
The present invention relates to triterpene compound, relate in particular to lanostane-type triterpenoid with anti-tumor activity and preparation method thereof, the invention still further relates to of the application of this lanostane-type triterpenoid, belong to biomedicine field as antineoplastic agent.
Background technology
Tumour is first killer who threatens human health, and seeking the effective antitumour compound is one of focus of new medicament screen.Glossy ganoderma all is the important Chinese medicine of strengthening the body resistance to consolidate the constitution since ancient times, in the field of motherland's medical science antagonism cancer, has brought into play original effect.Research shows that lanostane class triterpene and polyose composition are anti-tumor active substance bases important in the glossy ganoderma.Had been found that the Ganoderma triterpenoids of kind more than 100 at present, wherein, ganoderic acid U, V, W, X, the compound that great majority such as Y and Z have the lanostane parent nucleus has anti-tumor activity.The antineoplastic mechanism of such material is main directly kills with CDCC or to accelerate the apoptosis of cancer cells relevant.Therefore, the verivate of preparation lanostane class as much as possible and the research of extensively carrying out screening active ingredients and structure activity relationship are further to accelerate the strong approach that anti-tumor active substance is found paces, and might further develop and become anti-tumor drug.
Summary of the invention
One of the object of the invention provides one type of lanostane-type triterpenoid or its pharmaceutically useful salt with anti-tumor activity.
Two of the object of the invention provides a kind of above-mentioned method with lanostane-type triterpenoid of anti-tumor activity for preparing.
Above-mentioned purpose of the present invention realizes through following technical scheme:
Lanostane-type triterpenoid with anti-tumor activity, its structural formula are shown in formula I, II, III, IV or the V:
Certainly, can prepare the salt of The compounds of this invention acid addition, these salt are included in the present invention.
The acid salt of The compounds of this invention is preferably pharmaceutically acceptable, forms nontoxic salt with suitable acid (for example hydrochloric acid, acetic acid, sulfuric acid), and except pharmaceutically acceptable salt, other salt is also included among the present invention.
A kind of method for preparing above-claimed cpd (I-V) comprises:
(1) ethanol extraction of preparation glossy ganoderma daughter bacteria filament or sporophore;
(2) with the clear cream of ethanol extraction of glossy ganoderma daughter bacteria filament or sporophore with water-dispersion after, extract repeatedly with sherwood oil, use ethyl acetate extraction again, ethyl acetate extract;
(3) silicagel column on the ethyl acetate extract with chloroform-acetone (50: 1) gradient elution, according to the TLC spike, merges triterpenes components, is divided into A, B, C, D, E, six groups of F; B, C, D are gone up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, D-1, D-2, D-3 ten parts; B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Using the pH value is 3, and the solution separating B-3 that is made up of according to 56: 36: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula I compound; Using the pH value is 3, and the solution separating c-2 that is made up of according to 54: 32: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula II compound; Using the pH value is 3, and the solution separating B-3 that is made up of according to 54: 35: 6 volume ratio acetonitrile-water-methyl alcohol obtains the formula III compound; Using the pH value is 3, and the solution separating D-3 that is made up of according to 55: 35: 12 volume ratio acetonitrile-water-methyl alcohol obtains formula IV compound; Using the pH value is 3, and the solution separating D-3 that is made up of according to 56: 36: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula V compound;
The present invention separates from Ganoderma sporophore or fermentation mycelium and obtains 5 kinds of new lanostane verivates; Through evaluated biological activity; The new isolating 5 kinds of lanostane verivates of the present invention can effectively suppress the propagation of tumour cell; Have outstanding anti-tumor activity, can be used as the tumour agent clinically and use.
The present invention also provides a kind of antitumor medicine composition; This pharmaceutical composition is cooperated with pharmaceutically acceptable carrier by the The compounds of this invention of significant quantity or its pharmaceutically useful salt and forms; That is to say; With after pharmaceutically acceptable carrier or thinner cooperate, the formulation method conventional by this area is prepared into any one appropriate drug compsn with it with the The compounds of this invention of pharmaceutically acceptable consumption.With after pharmaceutically acceptable carrier or thinner cooperate, the formulation method conventional by this area is prepared into any one appropriate drug compsn with it with the The compounds of this invention of significant quantity.Usually said composition is suitable for oral administration and drug administration by injection, also is fit to other medication.Said composition can be liquid preparation forms such as tablet, capsule, pulvis, granule, lozenge, suppository, or oral liquid.According to different medications, pharmaceutical composition of the present invention can contain 0.1%-99% weight, the The compounds of this invention of preferred 10-60% weight.
Description of drawings
The disjunctive path figure of Fig. 1 lanostane-type triterpenoid of the present invention.
Embodiment
In order further to set forth the present invention, provide a series of embodiment below.These embodiment are illustrative fully, and they only are used for the present invention is specifically described, and are not to be understood that to be limitation of the present invention.
Embodiment 13 β-ethanoyl-7 beta-hydroxy-11,15, the preparation of 23-three oxidations-5 α-lanostane-8-alkene-26-acid (3-acetoxylganoderic acid B) (formula I compound)
Dry Ganoderma mycelium (3kg) is ground into meal, repeats to extract 3 times the vacuum concentration extracting solution with 15 times of volume ethanol; Medicinal extract disperses with an amount of zero(ppm) water; Extract repeatedly with sherwood oil (60-90 ℃), discard petroleum ether layer, water layer extracts with ETHYLE ACETATE repeatedly; Combined ethyl acetate layer, concentrating under reduced pressure get medicinal extract 105g.Silicagel column on the ETHYLE ACETATE medicinal extract with chloroform-acetone (50: 1) wash-out, according to TLC spike (in that sulfuric acid-methyl alcohol colour developing back shows redness or pale brown color spot point is triterpenes components), merges same section, is divided into 6 groups (A-F).B, C, D go up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge ten parts (B-1～B-3, C-1～C-5, D-1～D-3).B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Wherein, acetonitrile-water-methyl alcohol (56: 36: 8, transfer pH to 3 with formic acid) separation B-3 obtains 3-acetoxyl ganoderic acidB (white unformed powder).
ESI/MS：557[M-H]
-
1H-NMR：0.92，1.23，0.92，0.89，1.33，2.03，4.78，4.46
13C-NMR：217.6，207.8，197.9，179.9，171.1，80.2，66.8，24.2，21.5.
Embodiment 2 ethyls 3 β-ethanoyl-7 beta-hydroxy-11,15, the preparation of 23-three oxidations-5 α-lanostane-8-alkene-26-acid esters (3-acetoxyl ganoderate B) (formula II compound)
Dry Ganoderma mycelium (3kg) is ground into meal, repeats to extract 3 times the vacuum concentration extracting solution with 10 times of volume ethanol; Medicinal extract disperses with an amount of zero(ppm) water; Extract repeatedly with sherwood oil (60-90 ℃), discard petroleum ether layer, water layer extracts with ETHYLE ACETATE repeatedly; Combined ethyl acetate layer, concentrating under reduced pressure get medicinal extract 85g.Silicagel column on the ETHYLE ACETATE medicinal extract with chloroform-acetone (40: 1) wash-out, according to TLC spike (in that sulfuric acid-methyl alcohol colour developing back shows redness or pale brown color spot point is triterpenes components), merges same section, is divided into 6 groups (A-F).B, C, D go up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge ten parts (B-1～B-3, C-1～C-5, D-1～D-3).B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Wherein, acetonitrile-water-methyl alcohol (54: 32: 8, transfer pH to 3 with formic acid) separation of C-2 obtains ethyl 3-acetoxyl ganoderateB (yellow soup compound).
ESI/MS：557[M-H]
-
1H-NMR：0.92，1.23，0.93，0.89，1.23，1.33，2.03，4.12，4.78，4.46
13C-NMR：217.6，207.8，197.9，175.8，171.1，80.2，66.9，60.9，21.5
Embodiment 33, and 7,11,15,23-five oxidations-5 α-lanostane-8 β, the preparation of 9 α dihydro-26-acid (8 β, 9 α-dihydroganoderic acid C) (formula III compound)
Dry Ganoderma mycelium (3kg) is ground into meal, repeats to extract 3 times the vacuum concentration extracting solution with 20 times of volume ethanol; Medicinal extract disperses with an amount of zero(ppm) water; Extract repeatedly with sherwood oil (60-90 ℃), discard petroleum ether layer, water layer extracts with ETHYLE ACETATE repeatedly; Combined ethyl acetate layer, concentrating under reduced pressure get medicinal extract 75g.Silicagel column on the ETHYLE ACETATE medicinal extract with chloroform-acetone (50: 1) gradient elution, according to TLC spike (in that sulfuric acid-methyl alcohol colour developing back shows redness or pale brown color spot point is triterpenes components), merges same section, is divided into 6 groups (A-F).B, C, D go up gel SephadexLH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge ten parts (B-1～B-3, C-1～C-5, D-1～D-3).B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Wherein, acetonitrile-water-methyl alcohol (54: 35: 6, transfer pH to 3 with formic acid) separation B-3 obtains 8 β, 9 α-dihydroganodericacid C (white unformed powder).
ESI-MS?513[M-H]
-
1H-NMR：0.75，0.92，1.02，1.06，1.15，1.48，1.62，
13C-NMR：215.3，210.4，207.7，204.8，197.9，176.2，59.1，20.7，12.7
Embodiment 43 β-ethanoyl-15 Alpha-hydroxy-7,11, the preparation of 23-three oxidations-5 α-lanostane-8-alkene-26-acid (3-acetoxylganoderic acid K) (formula IV compound)
Dry Ganoderma mycelium (3kg) is ground into meal, repeats to extract 3 times the vacuum concentration extracting solution with 20 times of volume ethanol; Medicinal extract disperses with an amount of zero(ppm) water; Extract repeatedly with sherwood oil (60-90 ℃), discard petroleum ether layer, water layer extracts with ETHYLE ACETATE repeatedly; Combined ethyl acetate layer, concentrating under reduced pressure get medicinal extract 50g.Silicagel column on the ETHYLE ACETATE medicinal extract with chloroform-acetone (50: 1) gradient elution, according to TLC spike (in that sulfuric acid-methyl alcohol colour developing back shows redness or pale brown color spot point is triterpenes components), merges same section, is divided into 6 groups (A-F).B, C, D go up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge ten parts (B-1～B-3, C-1～C-5, D-1～D-3).B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Wherein, acetonitrile-water-methyl alcohol (55: 35: 12, transfer pH to 3 with formic acid) separation D-3 obtains 3-acetoxyl ganodericacid K (yellow soup compound).
ESI-MS?559[M+H]
+
H-NMR：0.75，0.92，1.02，1.06，1.15，1.48，1.62，
13C-NMR：215.3，210.4，207.7，204.8，197.9，176.2，59.1，20.7，12.7
Embodiment 5 ethyl 15 Alpha-hydroxies-3,7,11, the preparation of 23-four oxidations-5 α-lanostane-8-alkene-26-oate (ethylganoderate J) (formula V compound)
Dry Ganoderma mycelium (3kg) is ground into meal, repeats to extract 3 times the vacuum concentration extracting solution with 15 times of volume ethanol; Medicinal extract disperses with an amount of zero(ppm) water; Extract repeatedly with sherwood oil (60-90 ℃), discard petroleum ether layer, water layer extracts with ETHYLE ACETATE repeatedly; Combined ethyl acetate layer, concentrating under reduced pressure get medicinal extract 45g.Silicagel column on the ETHYLE ACETATE medicinal extract with chloroform-acetone (50: 1) gradient elution, according to TLC spike (in that sulfuric acid-methyl alcohol colour developing back shows redness or pale brown color spot point is triterpenes components), merges same section, is divided into 6 groups (A-F).B, C, D go up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge ten parts (B-1～B-3, C-1～C-5, D-1～D-3).B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Wherein, and acetonitrile-water-methyl alcohol (56: 36: 8, transfer pH to 3 to separate D-3 with formic acid and obtain ethyl ganoderate J (yellow soup compound).
ESI-MS?541[M-H]
-
H-NMR：0.89，0.91，0.93，1.14，1.17，1.20，1.28，4.15，4.31
13C-NMR：215.3，208.6，204.8，201.3，176.0，152.7，151.1，60.8，14.3
Test Example 1 formula I-V compound of the present invention is to the restraining effect test of growth of human tumor cells
1, test compound: the compound I-V that embodiment 1-5 is prepared;
2, TP:
The tumour cell of taking the logarithm vegetative period is inoculated in 96 orifice plates with 5000/hole, in 37 ℃ of 5%CO
2Cultivate under the condition after 10-12 hour, the administration group adds test compound, makes its final concentration be respectively 20-240 μ g/mL; The blank group is 0.08% DMSO 99.8MIN.; Positive controls is the cis-platinum of 20nmol/L, adopts the MTT colourimetry, measures the absorbance A value in wavelength 570nm/650nm place.Calculate the inhibiting rate of medicine according to the A value to growth of tumour cell.
The growth inhibition ratio of tumour cell=(the A value of the A value/negative control group of 1-experimental group) * 100%
3, test-results
Test-results shows that The compounds of this invention (I-V) has inhibition proliferation function (table 1) to kinds of tumor cells, especially lung cancer, nasopharyngeal carcinoma and liver cancer cell is had very strong restraining effect, and the propagation of gynecological tumor cell is also had good inhibitory effect.
Table 1 The compounds of this invention is to the inhibited proliferation of tumour cell
Claims (4)
1. structural formula is the lanostane-type triterpenoid shown in formula I, II, III, IV or the V or its pharmaceutically useful salt:
Formula I
Formula II
Formula III
Formula IV
Formula V.
2. one kind prepares the described lanostane-type triterpenoid of claim 1 method, comprising:
(1) ethanol extraction of preparation glossy ganoderma daughter bacteria filament or sporophore;
(2) with the clear cream of ethanol extraction of glossy ganoderma daughter bacteria filament or sporophore with water-dispersion after, extract repeatedly with sherwood oil, use ethyl acetate extraction again, ethyl acetate extract;
(3) silicagel column on the ethyl acetate extract carries out gradient elution with chloroform-acetone with 50: 1 ratio, according to the TLC spike, merges triterpenes components, is divided into A, B, C, D, E, six groups of F; B, C, D are gone up gel Sephadex LH-20 post respectively for three groups, with methanol-eluted fractions, according to TLC spike merge B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, D-1, D-2, D-3 ten parts; B-3, C-2, the D-3 part is further separated with half preparative high-performance liquid chromatographic appearance; Using the pH value is 3, and the solution separating B-3 that is made up of according to 56: 36: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula I compound; Using the pH value is 3, and the solution separating C-2 that is made up of according to 54: 32: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula II compound; Using the pH value is 3, and the solution separating B-3 that is made up of according to 54: 35: 6 volume ratio acetonitrile-water-methyl alcohol obtains the formula III compound; Using the pH value is 3, and the solution separating D-3 that is made up of according to 55: 35: 12 volume ratio acetonitrile-water-methyl alcohol obtains formula IV compound; Using the pH value is 3, and the solution separating D-3 that is made up of according to 56: 36: 8 volume ratio acetonitrile-water-methyl alcohol obtains formula V compound.
3. anti-tumor composition is made up of the described lanostane-type triterpenoid of the claim 1 of significant quantity or its pharmaceutically useful salt and pharmaceutically acceptable carrier or auxiliary material.
4. the described lanostane-type triterpenoid of claim 1 or its pharmaceutically useful salt are in the purposes of preparation in the antitumor drug.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810184588A CN101747400B (en) | 2008-12-17 | 2008-12-17 | Lanostane type triterpenoid with anti-tumor activity, preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810184588A CN101747400B (en) | 2008-12-17 | 2008-12-17 | Lanostane type triterpenoid with anti-tumor activity, preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101747400A CN101747400A (en) | 2010-06-23 |
| CN101747400B true CN101747400B (en) | 2012-09-05 |
Family
ID=42475072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810184588A Expired - Fee Related CN101747400B (en) | 2008-12-17 | 2008-12-17 | Lanostane type triterpenoid with anti-tumor activity, preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101747400B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070695B (en) * | 2010-12-10 | 2012-10-31 | 浙江大学 | Preparation and application of ergosterin derivative |
| CN102311475B (en) * | 2011-07-18 | 2013-02-06 | 福建医科大学 | New compound separated from Ganoderma lucidum, preparation method thereof and medicinal purpose thereof |
| CN103819437B (en) * | 2014-03-10 | 2015-07-01 | 中国科学院昆明植物研究所 | Spirolingzhine compounds as well as pharmaceutical composition and applications thereof |
| CN104892714B (en) * | 2015-04-22 | 2017-01-11 | 福建医科大学 | New ganoderma lucidum triterpene, preparation method and medicinal uses thereof |
| CN105037472B (en) * | 2015-06-29 | 2017-12-15 | 海南师范大学 | From the husky method for stewing and wool alkane type triterpenoid class compound being separated in dark sieve |
| CN108314616B (en) * | 2017-01-17 | 2020-10-27 | 浙江工业大学 | Triterpenoid and preparation and application thereof |
| CN108129541B (en) * | 2017-12-22 | 2020-04-14 | 成都普思生物科技股份有限公司 | Triterpenoid extracted from Ganoderma, and its preparation method and application |
| CN108467421B (en) * | 2018-03-05 | 2019-07-09 | 佳木斯大学 | Lanostane-type triterpene compound and its preparation method and application |
| CN108586559B (en) * | 2018-03-20 | 2020-01-07 | 佳木斯大学 | Lanostane type triterpenoid compound and preparation method and application thereof |
| CN112138031A (en) * | 2020-09-08 | 2020-12-29 | 广东都市菜族农业科技有限公司 | Preparation method and application of ganoderma lucidum spore powder extract containing ganoderma lucidum triterpene and ganoderma lucidum polysaccharide |
| CN114276398B (en) * | 2021-12-24 | 2022-12-30 | 大连医科大学附属第一医院 | Lanolin alkane type triterpenoid, preparation method and application thereof in preparation of CYP1A2 metabolic enzyme inhibitor |
| CN115124584A (en) * | 2022-07-28 | 2022-09-30 | 河南中医药大学 | Preparation method and application of two lanostane triterpene compounds in ganoderma lucidum |
| CN115463137B (en) * | 2022-09-02 | 2024-01-26 | 浙江寿仙谷植物药研究院有限公司 | Novel PD-1/PD-L1 small molecule inhibitor and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007109801A2 (en) * | 2006-03-23 | 2007-09-27 | Herbalscience Singapore Pte. Ltd. | Extracts and methods comprising ganoderma species |
| CN101190241A (en) * | 2006-11-28 | 2008-06-04 | 杨荣庆 | Ganoderrma tsugae extracting technique and preparations thereof |
-
2008
- 2008-12-17 CN CN200810184588A patent/CN101747400B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007109801A2 (en) * | 2006-03-23 | 2007-09-27 | Herbalscience Singapore Pte. Ltd. | Extracts and methods comprising ganoderma species |
| CN101190241A (en) * | 2006-11-28 | 2008-06-04 | 杨荣庆 | Ganoderrma tsugae extracting technique and preparations thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101747400A (en) | 2010-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101747400B (en) | Lanostane type triterpenoid with anti-tumor activity, preparation method and application | |
| Wu et al. | Inhibitory effects of ethyl acetate extract of Cordyceps sinensis mycelium on various cancer cells in culture and B16 melanoma in C57BL/6 mice | |
| EP2329816B1 (en) | An anti-cancer active substance from antrodia camphorata, method for preparing the same and use thereof | |
| CN101554409B (en) | Long pepper alkaloid and preparation method, preparation and application thereof | |
| CN104825500B (en) | Ganoderma leucocontextum extract, extraction method and application thereof | |
| CN102219821A (en) | Cardiac glycoside compounds and antitumor application thereof | |
| CN102552644B (en) | Anti-tumor use, preparation method and composition of garlic total polysaccharide | |
| CN101185671B (en) | Anti-tumor medicine extracted from Juglans regia and preparation method thereof | |
| CN103316096A (en) | General flavone extract of seeds of nigella damascena l., nigella sativa l. or nigella glandulifera freyn et sint., and preparation method and use thereof | |
| Li et al. | The Biological and Pharmacological Properties of Cordyceps sinesis, a Traditional Chinese Medicine That Has Broad Clinical Applications | |
| CN104910240A (en) | Bougainvillea glabra triterpenoid saponin, hpyerglycemic drugs with triterpenoid saponin as active component and preparation method and application thereof | |
| CN101485700B (en) | Refined cherimoya total inner ester with anti-tumor activity and preparation method thereof | |
| Belwal et al. | Ophiocordyceps sinensis | |
| CN102133220B (en) | Preparation method of pulsatilla saponin A | |
| CN113087756B (en) | Triterpenoid compound with tumor cell toxin activity and preparation method and application thereof | |
| CN101537036A (en) | Soap pod saponin extract as well as preparation method and application thereof | |
| Bhetwal et al. | Cordyceps sinensis: Peculiar caterpillar mushroom, salutary in its medicinal and restorative capabilities | |
| CN101234117A (en) | Medical use of a pair of ginseng saponin aglycones and their mixture | |
| CN102731276A (en) | Diterpene compound possessing antitumor activity, preparation method thereof and application thereof | |
| CN1775267A (en) | Kaikoujian extract, Its preparing method and use | |
| CN103360452B (en) | The Synthesis and applications of Muskmelon Base tetracyclic triterpene cucurbitane compound | |
| CN103239488A (en) | Application of crude extract product of Ardisia mamillata Hance | |
| CN102408464A (en) | Novel notriterpenoid saponin compound and preparation method and application thereof | |
| Arora | Cordyceps sinensis (berk.) sacc.-an entomophagous medicinal fungus-a review | |
| CN101245089A (en) | Process for producing a pair of novel ginsengenin and its compound body, and preparations thereof |
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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120905 Termination date: 20211217 |