CN102552371B - Gynostemma pentaphylla extractive and application thereof to preparing medicine for treating tumor - Google Patents
Gynostemma pentaphylla extractive and application thereof to preparing medicine for treating tumor Download PDFInfo
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- CN102552371B CN102552371B CN2012100114821A CN201210011482A CN102552371B CN 102552371 B CN102552371 B CN 102552371B CN 2012100114821 A CN2012100114821 A CN 2012100114821A CN 201210011482 A CN201210011482 A CN 201210011482A CN 102552371 B CN102552371 B CN 102552371B
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Abstract
The invention relates to a Gynostemma pentaphylla extractive which is enriched in damulin A, damulin B, gypenoside L and gypenoside LI, a preparation method of the Gynostemma pentaphylla extractive, and application of the extractive and four saponin compounds to preparing a medicine for treating a tumor. A cancer is selected from lung cancer, gastric cancer, liver cancer, breast cancer or leukemia.
Description
Technical field
The present invention relates to a kind of Herb Gynostemmae Pentaphylli (Gynostemma pentaphyllum) leaf extract that is rich in damulin A, damulin B, gypenoside L and gypenoside LI, the preparation method of this extract, and this extract and the purposes of these 4 kinds of saponins compounds in preparing the 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 again " Herba Gynostemmatis ", " snake king ", " Herb Gynostemmae Pentaphylli ", " Herb Gynostemmae Pentaphylli ", " Herba Gynostemmatis " etc.In Compendium of Material Medica, Gynostemma pentaphyllum Makino has 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 to Radix Ginseng, given again the good reputation of " southern Radix Ginseng ", " the second Radix Ginseng " 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, Herb Gynostemmae Pentaphylli has antitumaous effect, antioxidation, hypoglycemic activity
[11], effect for reducing blood fat
[11,12], strengthen immunization etc.Domestic is mainly to be grown on the south the Changjiang river, the Shaanxi of China, Yunnan, Hubei, Hunan, Guangdong, Guangxi, the 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.
In Herb Gynostemmae Pentaphylli, topmost active ingredient is saponin component.Research shows, in panax species active anticancer with low polarity, rare or the Tiny Panax ginseng saponin is directly related, as more precious in drug effects such as rare ginsenoside Rh2, Rg3, Rb3, shows unique curative effect aspect some refractory disease oncotherapy
[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, not only need a large amount of medicine resources, and 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, the Herb Gynostemmae Pentaphylli heat-treated products is compared with former plant, has stronger anti-tumor activity.Herb Gynostemmae Pentaphylli extract after hot-working provides theoretical foundation for anticarcinogen.
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 Advances in Germplasm [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?Q?W，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?SW480human?colorectal?cancer?cells[J].Phytother?Res，2009，23(1)：6-13.
Summary of the invention
The object of the invention is to propose a kind of Herb Gynostemmae Pentaphylli (Gynostemma pentaphyllum) leaf extract that is rich in damulin A (damulin A), damulin B (damulan B), gypenoside L and gypenoside LI, the preparation method of this extract, and this extract and the purposes of these 4 kinds of saponins compounds in preparing the medicine for treating tumor thing.
The preparation method of leaf of Herb Gynostemmae Pentaphylli extract of the present invention is as follows:
Get leaf of Herb Gynostemmae Pentaphylli and heat-treat 1-10 hour at 80-140 ℃, the high-temperature and high-pressure conditions of 0.08-0.50MPa, the leaf of Herb Gynostemmae Pentaphylli after processing is doubly measured 50%-95% alcohol reflux 1-5 time of (v/w, mL/g), 1-10h at every turn with 3-12.With the ethanol extract concentrating under reduced pressure of heat treatment leaf of Herb Gynostemmae Pentaphylli, drying obtains leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract.
Preferred extracting method is as follows:
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 processing with 80% alcohol reflux of 8 times of amounts (v/w, 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-treated products ethanol extract.
The present invention is by NMR and LC/MS technological means,, according to document, 4 effective ingredient in prepared leaf of Herb Gynostemmae Pentaphylli extract have been identified: damulin A (damulin A), damulin B (damulan B), gypenoside L and gypenoside LI.And the HPLC-MS analytical method, each effective ingredient in this extract has been carried out assay.Wherein:
The weight ratio that described 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 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 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.
In described leaf of Herb Gynostemmae Pentaphylli extract, the Isolation and Identification of effective ingredient is as follows:
, with the ethanol of 2 times of resin bed volumes (2BV), with the flow velocity of 2BV/h,, by HP-20 macroporous resin layer, and keep liquid level, soaked overnight.With ethanol with the flow velocity of 2BV/h by resin bed, be washed till effluent and add water and be not white in color till muddiness.Get ethanol elution appropriate, at 200-400nm scope interscan uv-spectrogram, in the obvious uv absorption of 250nm left and right nothing.With deionized water with the flow velocity of 2BV/h by resin bed, clean ethanol.With the HCl solution of 2BV 4%,, and soaked 3 hours by resin bed with the flow velocity of 5BV/h, then with deionized water, with same flow velocity, be washed till water lotion and be neutrality (pH detection paper pH=7)., with the NaOH solution of 2.5BV4%, with the flow velocity of 5BV/h, by resin bed and soaked 3 hours, then with deionized water, with same flow velocity, be washed till water lotion and be neutral (pH detection paper pH=7).
The ultrasonic suspendible of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract water is poured in macroporous resin HP20, with the flow velocity of 5BV/h by resin bed, and soak, absorption spends the night.Elution flow rate is 2BV/h, uses respectively 20%, 50%, 75%, 95%, 100% ethanol alcoholic solution eluting.
Above-mentioned 95% ethanol elution is carried out silica gel column chromatography, anti-phase C18 chromatography, separate and obtain 4 compounds, with NMR and LC/MS technological means,, according to document, finally be accredited as gypenoside gypenosdie L, gypenoside LI, damulin A, damulin B (table 1, Fig. 1, Fig. 2).
The nuclear magnetic resoance spectrum data of table 1 Herb Gynostemmae Pentaphylli heat-treated products effective ingredient
Structural formula of compound of the present invention is as follows:
We also find, the leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract that the present invention prepares and damulin A, damulin 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 preparing the 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-treated products ethanol extract (leaf of Herb Gynostemmae Pentaphylli extract of the present invention) high performance liquid chromatography (B)
The LC-MS collection of illustrative plates of saponins compound damulin A (A) in Fig. 2 leaf of Herb Gynostemmae Pentaphylli heat-treated products, damulin B (B), gypenoside L (C), gypenoside LI (D)
The specific embodiment
The preparation experiment of embodiment 1 extract
We have compared the extract that several different preparation methoies prepare, and have measured the wherein content of damulin A, damulin B, gypenoside L, four compounds of gypenoside LI.Result is as follows:
1, the preparation of Herb Gynostemmae Pentaphylli ethanol extract
Get 80% alcohol reflux 3 time of leaf of Herb Gynostemmae Pentaphylli with 8 times of amounts (v/w, mL/g), 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-treated products of leaf of Herb Gynostemmae Pentaphylli ethanol extract
Get 80% alcohol reflux 3 time of leaf of Herb Gynostemmae Pentaphylli with 8 times of amounts (v/w, mL/g), each 2h, concentrated, concentrated solution was heat-treated 3 hours at 125 ℃, the high-temperature and high-pressure conditions of 0.24MPa, and drying obtains the heat-treated products of leaf of Herb Gynostemmae Pentaphylli ethanol extract.
3, the preparation of the heat-treated products 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 processing with 80% alcohol reflux of 8 times of amounts (v/w, 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-treated products ethanol extract.
4, the preparation of positive controls Radix Ginseng heat-treated products 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 processing 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-treated products.
Utilize the HPLC-MS analytical method, Gynostemma pentaphyllum Makino alcohol extracts from the leaves, leaf of Herb Gynostemmae Pentaphylli ethanol extract heat-treated products, leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract carry out assay.
The content of damulin A, damulin B, gypenoside L, gypenoside LI in the different extracts of table 2
*N.D.: at HPLC-UV, LC-SIR/MS, LC-MRM/MS, substantially can't detect.
Result shows, and is as shown in table 2, and in leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract (the leaf of Herb Gynostemmae Pentaphylli extract of the present invention's preparation), the content of gypenoside damulin A, damulin B, gypenoside L, gypenoside LI is the highest.Especially, although the 3rd kind of extract that method makes compared with the 2nd kind of extract that method makes, it is only the difference of heat treatment and alcohol extraction order, but each active constituent content of heat-treated products extract is all higher than the latter, Epidemiological Analysis by statistics, this difference has significance, has produced unforeseeable technique effect.In addition, all do not detect these 4 kinds of effective ingredient in positive controls Radix Ginseng heat-treated products extract.
1, cell line and cell culture
Human lung cancer cell A549, gastric carcinoma cells MKN45, hepatoma carcinoma cell SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60, to contain 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, each extract that adds the DMEM culture fluid preparation that does not contain hyclone after cell attachment, in addition, the blank group that contains the full culture medium of DMEM and Radix Ginseng heat-treated products 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%CO2 incubator, abandon supernatant after every hole add DMSO150 μ L, jolting 10min.Microplate reader detects absorbance in 490nm wavelength place.Adopt the excel statistical analysis.
1) experiment material and instrument
Culture medium: DMEM culture medium (GIBCO, USA) (containing penicillin 100kU/L, pH7.4);
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);
Microplate reader.
2) experimental technique
Mtt assay is adopted in the inhibition determination of activity of human lung cancer cell A549, gastric carcinoma cells MKN45, hepatoma carcinoma cell SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60 etc.
3) test sample
Leaf of Herb Gynostemmae Pentaphylli ethanol extract, leaf of Herb Gynostemmae Pentaphylli ethanol extract heat-treated products, leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract (leaf of Herb Gynostemmae Pentaphylli extract of the present invention), damulin A, damulin B, gypenoside L, gypenoside LI, positive controls Radix Ginseng heat-treated products extract and ginsenoside Rg3.(preparation method of described extract is identical with the preparation method of each extract that embodiment 1 provides)
4) experimental result
Inhibition determination of activity to human lung cancer cell A549, gastric carcinoma cells MKN45, hepatoma carcinoma cell SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60 etc., result shows, as shown in table 3, Herb Gynostemmae Pentaphylli heat-treated products ethanol extract has very strong inhibitory action.
The inhibition of cancer cell determination of activity result of each extract of table 3
Separate 4 compounds that obtain in Herb Gynostemmae Pentaphylli heat-treated products ethanol extract of the present invention, be that damulin A, damulin B, gypenoside L, gypenoside LI and positive controls ginsenoside Rg3 carry out the active detection of inhibition of cancer cell, result shows, damulin A, damulin B, gypenoside L, gypenoside LI all have very strong inhibitory action to lung cell A549, gastric carcinoma cells MKN45, hepatoma carcinoma cell SMMC-7721, breast cancer cell MCF-7, leukaemia HL-60.
The IC of the saponins compound that the separation of table 4 Herb Gynostemmae Pentaphylli heat-treated products ethanol extract obtains to JEG-3
50Value
Experimental result shows, the damulin A that leaf of Herb Gynostemmae Pentaphylli heat-treated products ethanol extract of the present invention and separation thereof obtain, damulin B, gypenoside L, gypenoside LI have the anticancer activity.
Claims (5)
1. leaf of Herb Gynostemmae Pentaphylli extract, it is characterized in that, the preparation method of described leaf of Herb Gynostemmae Pentaphylli extract comprises the following steps: get leaf of Herb Gynostemmae Pentaphylli and heat-treat 1-10 hour at 125-140 ℃, the high-temperature and high-pressure conditions of 0.24-0.50MPa, the 50%-95% alcohol reflux that leaf of Herb Gynostemmae Pentaphylli after processing is doubly measured with 3-8 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; Contain following compound in described extract, and the weight ratio that compound accounts for the leaf of Herb Gynostemmae Pentaphylli extract is: damulin A18-30mg/g, damulin B5.5-30mg/g, gypenoside L5-20mg/g, gypenoside LI2.5-10mg/g; In described extract, the structural formula of compound is as follows:
2. leaf of Herb Gynostemmae Pentaphylli extract as claimed in claim 1, it is characterized in that, the preparation method of described leaf of Herb Gynostemmae Pentaphylli extract comprises the following steps: 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 processing with 80% alcohol reflux of 8 times of amounts 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.
3. the preparation method of leaf of Herb Gynostemmae Pentaphylli extract claimed in claim 1, it is characterized in that, the method comprises the following steps: get leaf of Herb Gynostemmae Pentaphylli and heat-treat 3-10 hour at 125-140 ℃, the high-temperature and high-pressure conditions of 0.24-0.50MPa, the 50%-95% alcohol reflux that leaf of Herb Gynostemmae Pentaphylli after processing is doubly measured with 3-8 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.
4. the application of the described leaf of Herb Gynostemmae Pentaphylli extract of claim 1 or 2 in preparation treatment cancer drug.
5. application as claimed in claim 4, is characterized in that, described cancer is selected from: pulmonary carcinoma, gastric cancer, hepatocarcinoma, breast carcinoma or leukemia.
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| EP4311553A1 (en) * | 2022-07-28 | 2024-01-31 | BTC Corporation | Method for preparing gynostemma pentaphyllum leaf extract and gynostemma pentaphyllum leaf extract prepared thereby |
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| CN108484711B (en) * | 2018-03-23 | 2019-04-05 | 海门市彼维知识产权服务有限公司 | A method of preparing gypenoside LI |
| CN108484713B (en) * | 2018-03-23 | 2019-03-05 | 娄志春 | A method of preparing gypenoside L |
| WO2019178980A1 (en) * | 2018-03-23 | 2019-09-26 | 娄志春 | Method for preparing gynostemma pentaphylla makino saponin lvi, xlvi, l, li, damulin a or damulin b |
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| EP4311553A1 (en) * | 2022-07-28 | 2024-01-31 | BTC Corporation | Method for preparing gynostemma pentaphyllum leaf extract and gynostemma pentaphyllum leaf extract prepared thereby |
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