CN102579471A - Applications of four gypenoside compounds to preparation of medicament for treating tumors - Google Patents
Applications of four gypenoside compounds to preparation of medicament for treating tumors Download PDFInfo
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- CN102579471A CN102579471A CN2012100114785A CN201210011478A CN102579471A CN 102579471 A CN102579471 A CN 102579471A CN 2012100114785 A CN2012100114785 A CN 2012100114785A CN 201210011478 A CN201210011478 A CN 201210011478A CN 102579471 A CN102579471 A CN 102579471A
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- gynostemmae pentaphylli
- herb gynostemmae
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Abstract
The invention relates to a gynostemma pentaphyllum leaf extract which is rich in damulin A, damulin b, gypenoside L and gypenoside LI, and applications of four saponin compounds to preparation of a medicament for treating tumors. Cancers are selected from lung cancer, stomach cancer, liver cancer, breast cancer or leukemia.
Description
Technical field
The present invention relates to a kind ofly be rich in Herb Gynostemmae Pentaphylli (Gynostemma pentaphyllum) leaf extract that reaches wooden woods A, reaches wooden woods B, gypenoside L and gypenoside LI, and the purposes of these 4 kinds of saponins compounds in preparation medicine for treating tumor thing.
Background technology
Herb Gynostemmae Pentaphylli is the herb of Cucurbitaceae (Cucurbitaceae) Gynostemma (Gynostemma) Herb Gynostemmae Pentaphylli Gynostemma pentaphyllum (Thunb.) Makino
[1], have heat-clearing and toxic substances removing, the eliminating phlegm and stopping cough function.Claim " Herba Gynostemmatis ", " snake king ", " Herb Gynostemmae Pentaphylli ", " Herb Gynostemmae Pentaphylli ", " Herba Gynostemmatis " etc. again.In the Compendium of Material Medica Herb Gynostemmae Pentaphylli there is following record " ipomoea cairica is controlled furuncle, insect bite, removing pathogenic heat from blood and toxic substance from the body, diuresis ".Because Herb Gynostemmae Pentaphylli contains the dammarane saponins similar with Radix Ginseng, is given the good reputation of " southern Radix Ginseng ", " second Radix Ginseng " again by hat
[2] [5-7], in addition, Herb Gynostemmae Pentaphylli also contains polysaccharide
[3,4], flavones ingredient
[8], aminoacid
[9], inorganic salt
[10]Deng.Modern pharmacology shows that Herb Gynostemmae Pentaphylli has antitumaous effect, antioxidation, hypoglycemic activity
[11], effect for reducing blood fat
[11,12], enhance immunity effect etc.Domestic mainly is to be grown on the south the Changjiang river, the Shaanxi of China, Yunnan, Hubei, Hunan, Guangdong, Guangxi, ground such as Fujian.The present domestic a plurality of series of products such as Herb Gynostemmae Pentaphylli tea, Herb Gynostemmae Pentaphylli concentrated juice, Herb Gynostemmae Pentaphylli dragon palpus tea, selenium-rich health tea that have.
Topmost active ingredient is a saponin component in the Herb Gynostemmae Pentaphylli.Research shows, active anticancer and low polarity in the panax species, rare or micro-ginsenoside are directly related, and be more precious like drug effects such as rare ginsenoside Rh2, Rg3, Rb3, aspect some refractory disease oncotherapy, shows unique curative effect
[13,14]But ginsenoside Rb1's content is higher in natural plants, and Rg3, Rh2, Compand K equal size are very little.For some strong active rare saponin is arranged, originate limited and to be present in the plant intensive amount lower, with traditional separation method, a large amount of medicine resource of needs not only, and also yield is also low.Therefore, how to improve the content of rare active component or the emphasis that the more activated one-tenth of acquisition is divided into modern pharmacy research.
Utilize high temperature and high pressure method, Herb Gynostemmae Pentaphylli heat treatment product is compared with former plant, has stronger anti-tumor activity.Herb Gynostemmae Pentaphylli extract after the hot-working is that anticarcinogen provides theoretical foundation.
List of references:
[1] Liang Qicheng, Zhong Ming, Chinese shape pharmacy [M], Guangxi Nationalities Press, 2005.
[2] Zhang Tao, Yuan Dishun. Chinese Herb Gynostemmae Pentaphylli germ plasm resource progress [J]. Yunnan Prov Agriculture University's journal, 2009,24 (3): 459-469.
[3]Yin?F，Zhang?YN，Yang?ZY，et?al.Nine?new?dammarane?saponins?from?Gynostemma?pentaphyllum[J].Chem?Biodivers，2006，3(7)：771-782.
[4]Huang?TH，Li?Y，Razmovski-Naumovski?V，et?al.Gypenoside?XLIX?isolated?from?Gynostemma?pentaphyllum?inhibits?nuclear?factor-kappaB?activation?via?a?PPAR-alpha-dependent?pathway[J].J?Biomed?Sci，2006，13(4)：535-548.
[5]Liu?X，Ye?W，Mo?Z，et?al.Three?dammarane-type?saponins?from?Gynostemma?pentaphyllum[J].Planta?Med，2005，71(9)：880-884.
[6]Hu?JH，Li?QW，Zhang?T，et?al.Effect?of?Gynostemma?Pentaphyllum?polysaccharide?on?boar?spermatozoa?quality?following?freezing-thawing[J].Cryobiology，2009，59(3)：244-249.
[7]Yang?X，Zhao?Y，Yang?Y，et?al.Isolation?and?characterization?of?immunostimulatory?polysaccharide?from?an?herb?tea，Gynostemma?pentaphyllum?Makino[J].J?Agric?Food?Chem，2008，56(16)：6905-6909.
[8]Kao?TH，Huang?SC，Inbaraj?BS，et?al.Determination?of?flavonoids?and?saponins?in?Gynostemma?pentaphyllum(Thunb.)Makino?by?liquid?chromatography-mass?spectrometry[J].Anal?Chim?Acta，2008，626(2)：200-211.
[9] Xu Cuifeng, Luo Jialiang, Wang Bilan, et al. Herb Gynostemmae Pentaphylli chemical composition analysis [J]. forest chemical engineering communication, 1994,2 (3-6.
[10] Peng Xiaolie, Liu Shibiao. the plant feed addictive-Herb Gynostemmae Pentaphylli [J] of DEVELOPMENT PROSPECT is arranged. Hebei animal and veterinary, 2005,21 (8): 40-41.
[11]Megalli?S，Davies?NM，Roufogalis?BD.Anti-hyperlipidemic?and?hypoglycemic?effects?of?Gynostemma?pentaphyllum?in?the?Zucker?fatty?rat[J].J?Pharm?Pharm?Sci，2006，9(3)：281-291.
[12]Huang?TH，Tran?VH，Roufogalis?BD，et?al.Gypenoside?XLIX，a?naturally?occurring?PPAR-alpha?activator，inhibits?cytokine-induced?vascular?cell?adhesion?molecule-1?expression?and?activity?in?human?endothelial?cells[J].Eur?J?Pharmacol，2007，565(1-3)：158-165.
[13] Li Xuezhe, Piao Huishun. ginsenoside Rh2's content assaying method and pharmacological research present situation [J]. Yanbian University's medical journal, 2009,32 (2): 153-156.
[14]Wang?CZ，Xie?JT，Fishbein?A，et?al.Antiproliferative?effects?of?different?plant?parts?of?Panax?notoginseng?on?SW480?human?colorectal?cancer?cells[J].Phytother?Res，2009，23(1)：6-13.
Summary of the invention
The objective of the invention is to propose a kind of Herb Gynostemmae Pentaphylli (Gynostemma pentaphyllum) leaf extract that reaches wooden woods A (damulin A), reaches wooden woods B (damulan B), gypenoside L and gypenoside LI that is rich in; This preparation method of extract, and this extract and the purposes of these 4 kinds of saponins compounds in preparation medicine for treating tumor thing.
Leaf of Herb Gynostemmae Pentaphylli preparation method of extract of the present invention is following:
Get leaf of Herb Gynostemmae Pentaphylli and heat-treated 1-10 hour, the leaf of Herb Gynostemmae Pentaphylli after handling is doubly measured (v/w, 50%-95% alcohol reflux mL/g) 1-5 time, 1-10h at every turn with 3-12 at 80-140 ℃, the high-temperature and high-pressure conditions of 0.08-0.50MPa.With the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract.
Preferred method for distilling is following:
Get leaf of Herb Gynostemmae Pentaphylli and heat-treated 3 hours at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa, with the leaf of Herb Gynostemmae Pentaphylli after handling with 8 times of amounts (v/w, 80% alcohol reflux mL/g) 3 times, 2h at every turn.With the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract.
The present invention according to document, has identified 4 effective ingredient in the prepared leaf of Herb Gynostemmae Pentaphylli extract: reach wooden woods A (damulin A), reach wooden woods B (damulan B), gypenoside L and gypenoside LI through NMR and LC/MS technological means.And the HPLC-MS analytical method, each effective ingredient in this extract has been carried out assay.Wherein:
The weight ratio that described chemical compound accounts for the leaf of Herb Gynostemmae Pentaphylli extract is: damulin A is no less than 14mg/g, damulin B and is no less than that 5mg/g, gypenoside L are no less than 3mg/g, gypenoside LI is no less than 2mg/g.
Preferably, described chemical compound accounts for the weight ratio of leaf of Herb Gynostemmae Pentaphylli extract and is: damulin A is no less than 18mg/g, damulin B and is no less than that 5.5mg/g, gypenoside L are no less than 5mg/g, gypenoside LI is no less than 2.5mg/g.
More preferred, the weight ratio that described chemical compound accounts for the leaf of Herb Gynostemmae Pentaphylli extract is: damulin A 18-30mg/g, damulin B 5.5-30mg/g, gypenoside L 5-20mg/g, gypenoside LI 2.5-10mg/g.
The separation of effective ingredient and evaluation are as follows in the said leaf of Herb Gynostemmae Pentaphylli extract:
With the ethanol of 2 times of resin bed volumes (2BV), through HP-20 macroporous resin layer, and keep liquid level, soaked overnight with the flow velocity of 2BV/h.With ethanol with the flow velocity of 2BV/h through resin bed, be washed till effluent and add water and be not white in color till the muddiness.It is an amount of to get ethanol elution, at 200-400nm scope interscan uv-spectrogram, and no obvious uv absorption about 250nm.With deionized water with the flow velocity of 2BV/h through resin bed, clean ethanol.With the HCl solution of 2BV 4%,, and soaked 3 hours through resin bed with the flow velocity of 5BV/h, then be washed till water lotion with same flow velocity and be neutrality (pH detection paper pH=7) with deionized water.With the NaOH solution of 2.5BV4%, through resin bed and soaked 3 hours, then be washed till water lotion with same flow velocity and be neutral (pH detection paper pH=7) with deionized water with the flow velocity of 5BV/h.
The ultrasonic suspendible of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract water is poured among the macroporous resin HP20, with the flow velocity of 5BV/h through resin bed, and soak, absorption spends the night.Elution flow rate is 2BV/h, uses 20%, 50%, 75%, 95%, 100% ethanol alcoholic solution eluting respectively.
Above-mentioned 95% ethanol elution is carried out silica gel column chromatography, anti-phase C18 chromatography; Separate and obtain 4 chemical compounds; With NMR and LC/MS technological means; According to document, finally be accredited as gypenoside gypenosdie L, gypenoside LI, reach wooden woods A, reach wooden woods B (table 1, Fig. 1, Fig. 2).
The nuclear magnetic resoance spectrum data of table 1 Herb Gynostemmae Pentaphylli heat treatment product effective ingredient
Structural formula of compound of the present invention is following:
We also find; The leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract that the present invention prepares and reach wooden woods A, reach wooden woods B, gypenoside L, gypenoside LI all have stronger inhibitory action for pulmonary carcinoma, gastric cancer, hepatocarcinoma, breast carcinoma and leukaemia; Therefore, the present invention also provides this leaf of Herb Gynostemmae Pentaphylli extract and the purposes of these 4 kinds of saponins compounds in preparation medicine for treating tumor thing.
Description of drawings
Fig. 1 leaf of Herb Gynostemmae Pentaphylli ethanol extract (A) and leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract (leaf of Herb Gynostemmae Pentaphylli extract of the present invention) HPLC (B)
Saponins compound in Fig. 2 leaf of Herb Gynostemmae Pentaphylli heat treatment product reaches wooden woods A (A), reaches wooden woods B (B), the LC-MS collection of illustrative plates of gypenoside L (C), gypenoside LI (D)
The specific embodiment
The preparation experiment of embodiment 1 extract
We have compared several kinds of extracts that different preparation prepares, and measured wherein reach wooden woods A, reach wooden woods B, the content of gypenoside L, four chemical compounds of gypenoside LI.The result is following:
1, the preparation of Herb Gynostemmae Pentaphylli ethanol extract
Get leaf of Herb Gynostemmae Pentaphylli with 8 times of amounts (v/w, 80% alcohol reflux mL/g) 3 times, each 2h.With the ethanol extract concentrating under reduced pressure of leaf of Herb Gynostemmae Pentaphylli, drying obtains the Herb Gynostemmae Pentaphylli ethanol extract.
2, the preparation of the heat treatment product of leaf of Herb Gynostemmae Pentaphylli ethanol extract
(each 2h concentrates for v/w, 80% alcohol reflux mL/g) 3 times, and concentrated solution was heat-treated 3 hours at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa, and drying obtains the heat treatment product of leaf of Herb Gynostemmae Pentaphylli ethanol extract with 8 times of amounts to get leaf of Herb Gynostemmae Pentaphylli.
3, the preparation of the heat treatment product ethanol extract of leaf of Herb Gynostemmae Pentaphylli (the leaf of Herb Gynostemmae Pentaphylli extract of the present invention's preparation)
Get leaf of Herb Gynostemmae Pentaphylli and heat-treated 3 hours at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa, with the leaf of Herb Gynostemmae Pentaphylli after handling with 8 times of amounts (v/w, 80% alcohol reflux mL/g) 3 times, 2h at every turn.With the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract.
4, the preparation of positive controls Radix Ginseng heat treatment product extract
Get Radix Ginseng and heat-treated 3 hours at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa, with the Radix Ginseng after handling with 80% alcohol reflux of 8 times of amounts (v/w) 3 times, 2h at every turn.With the ethanol extract concentrating under reduced pressure of heat treatment Radix Ginseng, drying obtains the extract of Radix Ginseng heat treatment product.
Utilize the HPLC-MS analytical method, leaf of Herb Gynostemmae Pentaphylli ethanol extract, leaf of Herb Gynostemmae Pentaphylli ethanol extract heat treatment product, leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract are carried out assay.
Reach wooden woods A in the different extracts of table 2, reach the content of wooden woods B, gypenoside L, gypenoside LI
*N.D.: HPLC-UV, LC-SIR/MS, LC-MRM/MS detect basically less than.
The result shows, and is as shown in table 2, and gypenoside reaches wooden woods A in the leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract (the leaf of Herb Gynostemmae Pentaphylli extract of the present invention's preparation), the content that reaches wooden woods B, gypenoside L, gypenoside LI is the highest.Especially; Though the 3rd kind of extract that method makes compared with the 2nd kind of extract that method makes; Only be the different of heat treatment and alcohol extraction order, but each active constituent content of heat treatment product extract all is higher than the latter, through statistical analysis; This difference has significance, has produced unforeseeable technique effect.In addition, all do not detect these 4 kinds of effective ingredient in the positive controls Radix Ginseng heat treatment product extract.
The experiment of embodiment 2 antitumous effects
1, cell line and cell culture
Human lung cancer cell A549, gastric carcinoma cells MKN45, HCC SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60 are containing the DMEM culture medium of 10% hyclone, under 37 ℃, saturated humidity, 5.0%CO
2Incubator in cultivate, cell is monolayer adherence growth.Test the trophophase cell of taking the logarithm.
2, mtt assay medicament sensitivity test
Digestion is collected the exponential phase cell and is adjusted to concentration and is about 1*10
5The single cell suspension of/mL; Every hole 100 μ L are inoculated in 96 orifice plates; Treat to add behind the cell attachment each extract of the DMEM culture fluid preparation that does not contain hyclone; In addition, the blank group that contains the full culture medium of DMEM and Radix Ginseng heat treatment product extract and ginsenoside Rg3's positive controls are also established in experiment, contain the 1%DMSO negative control group.Each concentration is established 6 multiple holes, and after continuing to cultivate 48h, every hole adds MTT 20 μ L and hatches 4h in 37 ℃, 5%C02 incubator, abandon supernatant after every hole add DMSO150 μ L, jolting 10min.ELIASA detects absorbance in the 490nm wavelength.Adopt the excel statistical analysis.
1) experiment material and instrument
Culture medium: (GIBCO USA) (contains penicillin 100kU/L, pH7.4) to the DMEM culture medium;
FBS(GIBCO，USA)；
Digestive system (pancreatin O.05%, 0.02%EDTA) (consonance cell resource center);
Dimethyl sulfoxide (DMSO): available from SIGMA (USA);
Thiazolyl blue (methyl thiazolyl tetrazolium, MTT): available from (AMRESCO, USA);
The 25mL culture bottle;
Inverted phase contrast microscope;
Cell culture incubator (Thermo Forma, USA);
ELIASA.
2) experimental technique
Mtt assay is adopted in the inhibition determination of activity of human lung cancer cell A549, gastric carcinoma cells MKN45, HCC SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60 etc.
3) supply test agent
Leaf of Herb Gynostemmae Pentaphylli ethanol extract, leaf of Herb Gynostemmae Pentaphylli ethanol extract heat treatment product, leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract (leaf of Herb Gynostemmae Pentaphylli extract of the present invention), reach wooden woods A, reach wooden woods B, gypenoside L, gypenoside LI, positive controls Radix Ginseng heat treatment product extract and ginsenoside Rg3.(said preparation method of extract is identical with each preparation method of extract that embodiment 1 provides)
4) experimental result
Inhibition determination of activity to human lung cancer cell A549, gastric carcinoma cells MKN45, HCC SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60 etc.; The result shows; As shown in table 3, Herb Gynostemmae Pentaphylli heat treatment product ethanol extract has very strong inhibitory action.
The cancerous cell of each extract of table 3 suppresses the determination of activity result
Separate 4 chemical compounds that obtain in the Herb Gynostemmae Pentaphylli heat treatment product ethanol extract of the present invention; Promptly reach wooden woods A, reach wooden woods B, gypenoside L, gypenoside LI and positive controls ginsenoside Rg3 and carry out cancerous cell and suppress active and detect; The result shows, reaches wooden woods A, reaches wooden woods B, gypenoside L, gypenoside LI all have very strong inhibitory action to lung cell A549, gastric carcinoma cells MKN45, HCC SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60.
The saponins compound that the separation of table 4 Herb Gynostemmae Pentaphylli heat treatment product ethanol extract obtains is to the IC of JEG-3
50Value
Experimental result shows, leaf of Herb Gynostemmae Pentaphylli heat treatment product ethanol extract of the present invention and separation thereof obtain reaches wooden woods A, reach wooden woods B, gypenoside L, gypenoside LI have the anticancer activity.
Claims (6)
1. a gypenoside compounds prepares the purposes of treating cancer drug, it is characterized in that this gypenoside compounds is have following structural compounds a kind of:
2. application as claimed in claim 1 is characterized in that, described cancer is selected from: pulmonary carcinoma, gastric cancer, hepatocarcinoma, breast carcinoma or leukemia.
3. the application of leaf of Herb Gynostemmae Pentaphylli extract in preparation treatment cancer drug is characterized in that, contains one or more chemical compounds as claimed in claim 1 in this leaf of Herb Gynostemmae Pentaphylli extract.
4. application as claimed in claim 3 is characterized in that, described cancer is selected from: pulmonary carcinoma, gastric cancer, hepatocarcinoma, breast carcinoma or leukemia.
5. application as claimed in claim 3; It is characterized in that the leaf of Herb Gynostemmae Pentaphylli preparation method of extract may further comprise the steps: get leaf of Herb Gynostemmae Pentaphylli and heat-treated 1-10 hour, the leaf of Herb Gynostemmae Pentaphylli after handling is doubly measured (v/w with 3-12 at 80-140 ℃, the high-temperature and high-pressure conditions of 0.08-0.50MPa; ML/g) 50%-95% alcohol reflux 1-5 time; Each 1-10h, with the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains the leaf of Herb Gynostemmae Pentaphylli extract.
6. application as claimed in claim 5; It is characterized in that the leaf of Herb Gynostemmae Pentaphylli preparation method of extract may further comprise the steps: get leaf of Herb Gynostemmae Pentaphylli and heat-treated 3 hours, the leaf of Herb Gynostemmae Pentaphylli after handling is measured (v/w with 8 times at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa; ML/g) 80% alcohol reflux 3 times; Each 2h, with the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains the leaf of Herb Gynostemmae Pentaphylli extract.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102603849A (en) * | 2012-02-10 | 2012-07-25 | 厦门华侨亚热带植物引种园 | Gynostemma pentaphylla secondary saponin, preparation method and applications thereof |
| CN103169725A (en) * | 2013-01-29 | 2013-06-26 | 中央民族大学 | Gynostemma pentaphyllum extract and application thereof in preparation of medicament for treating tumor |
| CN104163845A (en) * | 2014-06-27 | 2014-11-26 | 中央民族大学 | Compounds with antitumor activity, preparing method thereof and applications of the compounds |
| CN104188990A (en) * | 2014-08-08 | 2014-12-10 | 厦门华侨亚热带植物引种园 | Application of gypenoside XLV Ed in preparation of hepatoma resisting medicine |
| CN105998034A (en) * | 2016-05-18 | 2016-10-12 | 中央民族大学 | Application of micromolecular saponin compounds with function of up-regulating IL24 (interleukin 24) expression |
| CN108178778A (en) * | 2018-03-23 | 2018-06-19 | 娄志春 | A kind of method for preparing damulin B |
| CN108484711A (en) * | 2018-03-23 | 2018-09-04 | 娄志春 | A method of preparing gypenoside LI |
| CN108484713A (en) * | 2018-03-23 | 2018-09-04 | 娄志春 | A method of preparing gypenoside L |
| CN109851655A (en) * | 2018-11-22 | 2019-06-07 | 中央民族大学 | Dammarane saponins class compound, preparation method and application with anti-tumor activity |
| US10639343B2 (en) * | 2018-01-04 | 2020-05-05 | Btc Corporation | Preparation method of Gynostemma pentaphyllum leaves extract and Gynostemma pentaphyllum extract prepared by the method thereof |
| KR20230109918A (en) | 2022-01-14 | 2023-07-21 | 주식회사 비티씨 | Composition for enhancement of exercise performance comprising gypenoside compounds as an active ingredient |
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| CN102603849A (en) * | 2012-02-10 | 2012-07-25 | 厦门华侨亚热带植物引种园 | Gynostemma pentaphylla secondary saponin, preparation method and applications thereof |
| CN103169725A (en) * | 2013-01-29 | 2013-06-26 | 中央民族大学 | Gynostemma pentaphyllum extract and application thereof in preparation of medicament for treating tumor |
| CN104163845A (en) * | 2014-06-27 | 2014-11-26 | 中央民族大学 | Compounds with antitumor activity, preparing method thereof and applications of the compounds |
| CN104163845B (en) * | 2014-06-27 | 2016-08-24 | 中央民族大学 | There is the compound of anti-tumor activity, its preparation method and application |
| CN104188990A (en) * | 2014-08-08 | 2014-12-10 | 厦门华侨亚热带植物引种园 | Application of gypenoside XLV Ed in preparation of hepatoma resisting medicine |
| CN104188990B (en) * | 2014-08-08 | 2016-08-17 | 厦门华侨亚热带植物引种园 | Gypenoside XLV Ed application in preparing medicines resistant to liver cancer |
| CN105998034A (en) * | 2016-05-18 | 2016-10-12 | 中央民族大学 | Application of micromolecular saponin compounds with function of up-regulating IL24 (interleukin 24) expression |
| US10639343B2 (en) * | 2018-01-04 | 2020-05-05 | Btc Corporation | Preparation method of Gynostemma pentaphyllum leaves extract and Gynostemma pentaphyllum extract prepared by the method thereof |
| CN108178778A (en) * | 2018-03-23 | 2018-06-19 | 娄志春 | A kind of method for preparing damulin B |
| CN108484711A (en) * | 2018-03-23 | 2018-09-04 | 娄志春 | A method of preparing gypenoside LI |
| CN108484713A (en) * | 2018-03-23 | 2018-09-04 | 娄志春 | A method of preparing gypenoside L |
| CN109851655A (en) * | 2018-11-22 | 2019-06-07 | 中央民族大学 | Dammarane saponins class compound, preparation method and application with anti-tumor activity |
| KR20230109918A (en) | 2022-01-14 | 2023-07-21 | 주식회사 비티씨 | Composition for enhancement of exercise performance comprising gypenoside compounds as an active ingredient |
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