CN101899082A - Triterpenoid saponin compound, application and preparation method - Google Patents
Triterpenoid saponin compound, application and preparation method Download PDFInfo
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Abstract
The invention provides triterpenoid saponin compounds, applications and preparation methods, relating to a compound Phaseoloideside D and a compound Phaseoloideside E obtained by separating from mimosoideae entada phaseoloides leguminous plants and medical applications as well as preparation methods thereof. The in-vitro anti-tumor experiment indicates that the compound Phaseoloideside D and the compound Phaseoloideside E have stronger inhibiting effect on SHG-44 (human glioma), SW480 (colon cancer cells), HepG-2 (liver cancer cells), Ec-109 (esophageal cancer cells) and MCF-7 (human breast cancer cells), can provide a leading compound for preparing new antineoplastics and has key value to develop and use medicinal resources in China.
Description
Technical field
The present invention relates to triterpene saponin componds, purposes and preparation method, be specifically related to from leguminous plants Touch-me-notAction Plant Ya Ke Ke Teng Shu Ke vine, separate Compound P haseoloideside D, Phaseoloideside E and medicinal use and the preparation method who obtains.
Background technology
Ke vine (Entada phaseoloides (Linn.) Merr.) belongs to pulse family Touch-me-notAction Plant Ya Ke Ke Calamus, evergreen wooden big liana, and stem is twisted, and branch does not have hair; Two times pinnately compound leaves, long 10-25cm has 2 pairs of accessory pinnas usually, and the top is given birth to a pair of accessory pinna and is become tendril; Leaflet 2-4 is right, keratin, and oblong, long 3-8.5cm, wide 1.5-4cm, tip is blunt, nick, base portion is deflection slightly, does not have hair.Mainly be distributed in ground such as China Fujian, Guangxi, Yunnan, it mainly contains Ke rattan amides, triterpenoid saponin constituents, has the effect of treatment stomach trouble, hemorrhoid, constipation etc.
The triterpenoid saponin constituents that is contained in the Ke vine congener of following bibliographical information has certain anti-tumor activity: Laurence KN, Luciano B, Remy BT et al.Rheediinosides A and B, two antiproliferativeand antioxidant triterpene saponins from Entada rheedii.Phytochemistry.2010,71:254-261; Giuseppina C, Fabrizio D P, Paolo De C, et al.Antiproliferative TriterpeneSaponins from Entada africana J.Nat.Prod.2006,69,1323-1329.; Azefack L T, TomofumiM, Mirjolet, J F.Pursaethosides A-E, Triterpene Saponins from Entada pursaetha.J.Nat.Prod.2005,68,1185-1190.
The total saponins thing that contains in the Ke vine also has the obvious suppression effect to mouse S180 solid tumor, (Ke vine water soluble extract is to the restraining effect of mice-transplanted tumor S180, Xu Teng etc., Chinese pharmacist obviously to prolong ehrlich ascites tumor mouse survival time, 2006,9 (5): 397-399); Ke vine water soluble extract also has the extracorporeal anti-tumor function of stronger restraining effect (Ke vine water soluble extract to human chronic myelogenous leukemia cell strain (K562), human lymphoma cell strain (U937) and human promyelocytic leukemia cell strain (HL60), Xu Teng etc., the West China pharmaceutical journal, 2005,20 (6): 487-489).
The south of plum, people such as Xiong Hui (" Ke vine sulfur-bearing amides The Chemical Constituents ", " Acta Pharmaceutica Sinica " 2010,45 (5): 624-626) disclose and utilize positive reversed-phase silica gel column chromatography, preparation HPLC Fen is from the chemical ingredients of Chunization Ke vine kind benevolence, obtain 4 sulfur-bearing amidess from the n-butanol extraction position separation of 70% ethanol extraction, be respectively entadamide A-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside (1), entadamide A (2), entadamide A-β-Dglucopyranoside (3) and clinacoside C (4).People such as Zhang Yong (" Ke vine kind Renhua composition Study ", the 43rd the 14th phase of volume of " Chinese Pharmaceutical Journal " July in 2008) discloses by separation purifying such as Sephadex LH-20, measure and after modern Wave Spectrum technology carries out the structure evaluation by physicochemical constant, separate and obtain 8 compounds, be respectively 2,5-dihydroxyphenyl acetic acid ethyl ester, 2,5-dihydroxyphenyl acetic acid methyl esters, 5-hydroxyl-cumarone-2 Tong, Ke rattan acid amides A, methyl stearate, β-Gu Zaichun, daucosterol and Stigmasterol.Chinese patent CN 101486650A discloses and has a kind ofly prepared 2 from beans section Ke rattan platymiscium Ke rattan, 5-dihydroxyphenyl acetic acid ethyl ester, 2,5-dihydroxyphenyl acetic acid methyl esters, 2, the method for the positive butyl ester of 5-dihydroxyphenyl acetic acid, and the application of these compounds in the preparation inverase.
Yet, also do not have the researchist to report saponins compound Phaseoloideside D and Phaseoloideside E contained in the You Guan Ke vine at present.
Summary of the invention
One of purpose of the present invention provides Compound P haseoloideside D, the Phaseoloideside E that separation obtains from leguminous plants Touch-me-notAction Plant Ya Ke Ke Teng Shu Ke vine.
The contriver from grow in Chinese yunnan Xishuangbanna area De Ke vine kind benevolence extraction separation to two kinds of new saponins compounds, called after Phaseoloideside D respectively:
3-O-β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)]-2-acetylamino-2-deoxy-β-D-glucopyranosylentagenic?acid28-O-β-D-apiofuranosyl-(1→5)-O-β-D-apiofuranosyl-(1→2)-2-acetyl-2-deoxy-O-β-D-glucopyranoside；
With Phaseoloideside E:
3-O-β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)]-2-acetylamino-2-deoxy-β-D-glucopyranosylentagenic?acid28-O-β-D-apiofuranosyl-(1→3)-O-β-D-xylopyranosyl-(1→2)-2-acetyl-2-deoxy-O-β-D-glucopyranoside。
Its chemical structure is as follows:
Two of purpose of the present invention is open Phaseoloideside D or the application of Phaseoloideside E in the preparation antitumor drug.
The contriver confirms by experiment in vitro, Phaseoloideside D demonstrates the obvious suppression effect to SHG-44 (human glioma cell), SW480 (colon cancer cell), HepG-2 (liver cancer cell), Ec-109 (esophageal cancer cell), MCF-7 (human breast cancer cell), and Phaseoloideside E demonstrates the obvious suppression effect to JEG-3 SHG-44, SW480, HepG-2.As seen, triterpene saponin componds Phaseoloideside D of the present invention and Phaseoloideside E have the effect of obvious suppression tumour.
The method of extraction separation Phaseoloideside D, Phaseoloideside E in the three Shi Ti Gong Ke vines of purpose of the present invention.
After the contriver gropes by a large amount of tests, two kinds of methods of extraction separation Phaseoloideside D, Phaseoloideside E have efficiently been obtained.
The step of first kind of method for preparing Compound P haseoloideside D, Phaseoloideside E is as follows:
(1) preparation total saponin extracts: pulverizes the oven dry of Ke vine kind benevolence dry product, the ethanol room temperature lixiviate with 60～70% 3～7 times, and each 24h, concentrated extracting solution gets medicinal extract; With volume ratio 9: 1 methanol-water solution dissolving medicinal extract, after extracting successively with isopyknic sherwood oil, ethyl acetate, propyl carbinol, with n-butyl alcohol extract, pass through silica gel column chromatography, separate with methylene chloride-methanol solution gradient wash-out, collect elutriant, decompression and solvent recovery gets total saponin extracts;
(2) separate: the above-mentioned total saponin extracts applying silicon plastic column chromatography that contains, with ethyl acetate: methyl alcohol is the eluent gradient elution, collection contains stream part of triterpenoid saponin, again through the ODS column chromatography, with methyl alcohol: water is that eluent carries out gradient elution, collect stream part of described compound, again through silica gel column chromatography, with chloroform: methyl alcohol is that eluent carries out gradient elution, collect stream part of described compound, separate through half preparative high-performance liquid chromatographic method again, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water is carried out wash-out, collection contains Phaseoloideside D, the flow point of Phaseoloideside E reclaims solvent and promptly gets described compound pure product Phaseoloideside D and Phaseoloideside E.Through the various modern spectroscopic analysis, chemical structure and the steric configuration of Phaseoloideside D and Phaseoloideside E have been determined in the particularly parsing of the multiple advanced person's of integrated application two NMR (Nuclear Magnetic Resonance) spectrum.
The step of second kind of method for preparing Compound P haseoloideside D, Phaseoloideside E is as follows:
(1) pulverizes the oven dry of Ke vine kind benevolence dry product, the ethanol room temperature lixiviate of usefulness 60-70% 3-7 time, each 24h, concentrated extracting solution, use petroleum ether degreasing then, the medicinal extract of degreasing is redissolved through n-butanol extraction, ethanol, after the vacuum-drying, be dissolved in methanol-water solution again, by macroporous resin, use the ethanol-water solution gradient elution, collect elutriant, decompression recycling ethanol gets total saponin extracts;
(2) separate: the above-mentioned total saponin extracts applying silicon plastic column chromatography that contains, with the ethyl acetate, alcohol and water is the eluent gradient elution, collection contains stream part of triterpenoid saponin, again through the ODS column chromatography, with methyl alcohol: water is that eluent carries out gradient elution, collection contains stream part of described compound, separate through half preparative high-performance liquid chromatographic method again, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water is carried out wash-out, collection contains Phaseoloideside D, the flow point of Phaseoloideside E reclaims solvent and promptly gets described compound pure product Phaseoloideside D and Phaseoloideside E.Through the various modern spectroscopic analysis, chemical structure and the steric configuration of Phaseoloideside D and Phaseoloideside E have been determined in the particularly parsing of the multiple advanced person's of integrated application two NMR (Nuclear Magnetic Resonance) spectrum.
Compound disclosed by the invention can be used as the lead compound of antitumor drug, provides a kind of new thinking for developing new antitumor drug, and is significant to the national resources of medicinal plant that develops China.
Embodiment
Below further describe the present invention by preferred embodiment, yet the scope of the invention is not limited only to the following example.Every do not deviate from the change of the present invention design or be equal to substitute include within protection scope of the present invention.
The preparation of embodiment 1 triterpene saponin componds Phaseoloideside D and Phaseoloideside E
1, extraction separation and purification process
Jiang the Gan Zao Ke vine medicinal material De Ke vine benevolence of shelling, dry, pulverize 8000 grams of weighing, extract 3 times with the ethanol soaking at room temperature of 4 times of amounts 70% again, each 24h with the leaching liquid concentrating under reduced pressure, gets translucent medicinal extract 518g.With volume ratio 9: 1 methanol-water mixed solvent dissolving medicinal extract, extract repeatedly with isopyknic sherwood oil, colourless substantially to petroleum ether layer, medicinal extract is soluble in water, it is colourless substantially to be extracted to ethyl acetate layer repeatedly with isopyknic ethyl acetate, it is colourless substantially to be extracted to n-butanol layer repeatedly with isopyknic propyl carbinol again, merges n-butanol layer and concentrating under reduced pressure and gets translucent mobile medicinal extract 129g.And with n-butanol portion as main separate part, carry out silica gel column chromatography, select for use methylene chloride-methanol to carry out gradient elution, collect the elutriant that contains saponin(e, decompression and solvent recovery must contain total saponin extracts 38.15 grams.To contain total saponins and carry out silica gel column chromatography, with ethyl acetate: methyl alcohol is the eluent wash-out, collects the elutriant that contains triterpenoid saponin, and decompression and solvent recovery gets triterpenoid saponin 18.59 grams.This triterpenoid saponin is carried out the ODS column chromatography, with methyl alcohol: water is that eluent carries out gradient elution, collection contains stream part of Compound P haseoloideside D and Phaseoloideside E, again through silica gel column chromatography, with chloroform: methyl alcohol is that eluent carries out gradient elution, collect stream part of Compound P haseoloideside D and Phaseoloideside E, after half preparative high-performance liquid chromatographic method separate, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water is carried out wash-out, promptly get pure product 0.3 gram of Phaseoloideside D, pure product 0.35 gram of Phaseoloideside E.
2, compound structure is identified
Phaseoloideside D is white amorphous powder, and Lieberman-Burchard reaction and Molish reaction are all after measured positive, molecular formula C
72H
115NO
37, [α]
D 20-41 (c 0.63, MeOH), and FAB-MS m/z 1586[M-1]
-, 1453[M-132-1]
-, 1423[M-162-1]
-, 1321[M-132-132-1]
-, 1117[M-162-132-132-42-1]
-HR ESI-MS provides quasi-molecular ion peak m/z 1608.7082[M+Na]
+(Calc Mass 1608.7040).
The structural formula of Phaseoloideside D is as follows:
Phaseoloideside D's
1H-NMR,
13C-NMR and HMBC data such as table 1.
Table 1 Phaseoloideside D's
1H-NMR,
13C-NMR and HMBC data (in C
5D
5N, δ ppm)
Phaseoloideside E is white amorphous powder, and Lieberman-Burchard reaction and Molish reaction are all after measured positive, molecular formula C
72H
115NO
37, [α]
D 20-41 (c 0.63, MeOH), and FAB-MS m/z 1586[M-1]
-, 1453[M-132-1]
-, 1423[M-162-1]
-, 1321[M-132-132-1]
-, 1117[M-162-132-132-42-1]
-HR ESI-MS provides quasi-molecular ion peak m/z 1608.7019[M+Na]
+(Calc Mass 1608.7040).
The structural formula of Phaseoloideside E is as follows:
Phaseoloideside E's
1H-NMR,
13C-NMR and HMBC data such as table 2.
Table 2 Phaseoloideside E's
1H-NMR,
13C-NMR and HMBC data (in C
5D
5N, δ ppm)
The preparation of embodiment 2 triterpene saponin componds Phaseoloideside D and Phaseoloideside E
Ke vine kind benevolence is dried, pulverize 10000 grams of weighing, with 70% ethanol room temperature lixiviate of 5 times of amounts 7 times, each 24h, concentrated extracting solution, and then use petroleum ether degreasing, with the medicinal extract of degreasing behind n-butanol extraction, with dissolving in alcoholic acid water layer composition, after vacuum-drying (dry weight 345 grams), be dissolved in volume ratio again and be 9: 1 methanol-water solution, by macroporous resin, water and ethanol gradient elution are collected 50% ethanol eluate, decompression recycling ethanol gets total saponin extracts 61.61 grams.Total saponin extracts applying silicon plastic column chromatography, with ethyl acetate: methyl alcohol: water is the eluent gradient elution, collection contains stream part of this triterpenoid saponin, through the ODS column chromatography, with methyl alcohol: water is that eluent carries out gradient elution, collection contains stream part of Compound P haseoloideside D and Phaseoloideside E, separate through half preparative high-performance liquid chromatographic method again, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water is carried out wash-out, promptly get about 0.5 gram of the pure product of Phaseoloideside D, about 0.55 gram of the pure product of Phaseoloideside E.
Embodiment 3Phaseoloideside D and Phaseoloideside E are to the influence of tumour cell
Testing used cell strain is international tumor cell line, that is: SHG-44 (human glioma cell), SW480 (colon cancer cell), HepG-2 (liver cancer cell), Ec-109 (esophageal cancer cell), MCF-7 (human breast cancer cell).
Phaseoloideside D and Phaseoloideside E are to cancer cells cytodifferentiation inducing action---the mtt assay of vitro culture: its principle is that the succinodehydrogenase in the viable cell plastosome can make exogenous MTT be reduced to water-insoluble bluish voilet crystallization first a ceremonial jade-ladle, used in libation (Formazan) and is deposited in the cell, and dead cell does not have this function.First a ceremonial jade-ladle, used in libation in dimethyl sulfoxide (DMSO) (DMSO) the energy dissolved cell, measure its absorbance value with enzyme-linked immunosorbent assay instrument at 492nm wavelength place, can obtain the cancer cells number change of cancer therapy drug effect, once obtain the survival rate of cell, judge the sensitivity of cell anticarcinogen by IC50.According to cell growth rate, the tumour cell that will be in the growth logarithmic phase is inoculated in 96 orifice plates with 100 μ l/ holes, and adherent growth 24h inhales and goes to add 100 μ l/ holes after the supernatant liquor.Each concentration is established 6 multiple holes, and establishes substratum contrast and the acellular zeroing hole that does not add soup.Tumour cell is at 37 ℃, 5%CO
2Cultivated 24 hours in the incubator, every then hole adds 10 μ l MTT, continues to cultivate 4h in the incubator, takes out, and inhales and removes supernatant liquor, adds DMSO 150 μ l/ holes, and microplate reader 492nm wavelength is surveyed the 0D value down, and experimental result sees Table 3:
Table 3 Phaseoloideside D is to the restraining effect IC50 (μ M) of tumour cell
IC50: the half effective inhibition concentration of expression The compounds of this invention
Above-mentioned experimental result shows that Phaseoloideside D shows the obvious suppression effect to SHG-44, SW480, HepG-2, Ec-109, MCF-7, and Phaseoloideside E shows the obvious suppression effect to SHG-44, SW480, HepG-2.As seen, triterpene saponin componds Phaseoloideside D of the present invention and Phaseoloideside E have the effect of obvious suppression tumour.
Claims (6)
1. triterpene saponin componds, structural formula is as follows:
2. triterpene saponin componds, structural formula is as follows:
3. the application of the described compound of claim 1 in the preparation antitumor drug.
4. the application of the described compound of claim 2 in the preparation antitumor drug.
5. the preparation method of claim 1 or 2 described compounds comprises the steps:
(1) pulverizes the oven dry of Ke vine kind benevolence dry product, the ethanol room temperature lixiviate of usefulness 60-70% 3-7 time, and each 24h, concentrated extracting solution gets medicinal extract; With volume ratio is 9: 1 methanol-water solution dissolving medicinal extract, after extracting successively with isopyknic sherwood oil, ethyl acetate, propyl carbinol, n-butyl alcohol extract is passed through silica gel column chromatography, with methylene chloride-methanol solution gradient wash-out, collect elutriant, decompression and solvent recovery gets total saponin extracts;
(2) with described total saponin extracts applying silicon plastic column chromatography, with ethyl acetate-methanol solution is the eluent wash-out, collection contains stream part of triterpenoid saponin, again through the ODS column chromatography, with the methanol-water is that eluent carries out gradient elution, collection contains stream part of described compound, again through silica gel column chromatography, with chloroform-methanol solution is that eluent carries out gradient elution, collect stream part of described compound, separate through half preparative high-performance liquid chromatographic method again, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water carry out behind the wash-out described compound.
6. the preparation method of claim 1 or 2 described compounds comprises the steps:
(1) pulverizes the oven dry of Ke vine kind benevolence dry product, the ethanol room temperature lixiviate of usefulness 60-70% 3-7 time, each 24h, concentrated extracting solution, use petroleum ether degreasing then, the medicinal extract of degreasing is redissolved through n-butanol extraction, ethanol, after the vacuum-drying, be dissolved in methanol-water solution again, by macroporous resin, use the ethanol-water solution gradient elution, collect elutriant, decompression recycling ethanol gets total saponin extracts;
(2) with above-mentioned total saponin extracts applying silicon plastic column chromatography, with the ethyl acetate, alcohol and water is the eluent gradient elution, collection contains stream part of triterpenoid saponin, again through the ODS column chromatography, with methyl alcohol: water is that eluent carries out gradient elution, collection contains stream part of described compound, separate through half preparative high-performance liquid chromatographic method, with acetonitrile: 2.8: 7.2 moving phase of the volume ratio of water carry out behind the wash-out described compound.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102229640A (en) * | 2011-06-30 | 2011-11-02 | 中国人民解放军第四军医大学 | Application of triterpenoid saponins compound extracted from anemone taipaiensis |
| CN102488095A (en) * | 2011-12-23 | 2012-06-13 | 南京正宽医药科技有限公司 | Green feedstuff additive containing camellia seed triterpenoid saponin |
| CN102649807A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Preparation method of Heteropappus altaicus saponin (I) |
| CN112236199A (en) * | 2018-04-12 | 2021-01-15 | 爱西美公司 | Method for producing Entada phaseoloides seed extract rich in metabolites of interest, extract produced by the method, and cosmetic and skin care applications of the extract |
| CN115651055A (en) * | 2022-10-31 | 2023-01-31 | 上海市奉贤区中心医院 | Oleanane-type triterpene saponin compound and preparation method and application thereof |
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Non-Patent Citations (3)
| Title |
|---|
| 《Phytochemistry》 20091105 Laurence Kegah Nzowa et al Rheediinosides A and B, two antiproliferative and antioxidant triterpene saponins from Entada rheedii 254-261 2,4 第71卷, 2 * |
| 《中国药学杂志》 20080731 张勇等 榼藤子种仁化学成分研究 1063-1065 1-6 第43卷, 第14期 2 * |
| 《华西药学杂志》 20051231 许腾等 榼藤子水溶性提取物的体外抗肿瘤作用 487-489 1-6 第20卷, 第6期 2 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102649807A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Preparation method of Heteropappus altaicus saponin (I) |
| CN102229640A (en) * | 2011-06-30 | 2011-11-02 | 中国人民解放军第四军医大学 | Application of triterpenoid saponins compound extracted from anemone taipaiensis |
| CN102488095A (en) * | 2011-12-23 | 2012-06-13 | 南京正宽医药科技有限公司 | Green feedstuff additive containing camellia seed triterpenoid saponin |
| CN102488095B (en) * | 2011-12-23 | 2013-02-27 | 重庆优宝生物技术有限公司 | Green feedstuff additive containing camellia seed triterpenoid saponin |
| CN112236199A (en) * | 2018-04-12 | 2021-01-15 | 爱西美公司 | Method for producing Entada phaseoloides seed extract rich in metabolites of interest, extract produced by the method, and cosmetic and skin care applications of the extract |
| CN112236199B (en) * | 2018-04-12 | 2023-07-18 | 爱西美公司 | Entada phaseoloides seed extract, its production method and cosmetic application |
| CN115651055A (en) * | 2022-10-31 | 2023-01-31 | 上海市奉贤区中心医院 | Oleanane-type triterpene saponin compound and preparation method and application thereof |
| CN115651055B (en) * | 2022-10-31 | 2024-03-29 | 上海市奉贤区中心医院 | Oleanane type triterpene saponin compound, and preparation method and application thereof |
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| CN101899082B (en) | 2012-10-24 |
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