CN100584856C - The purposes of a kind of Hederagenin, its preparation method and preparation antitumor drug thereof - Google Patents
The purposes of a kind of Hederagenin, its preparation method and preparation antitumor drug thereof Download PDFInfo
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Abstract
The present invention relates to natural medicine field, be specifically related to a kind of compound of extraction separation (I) from woodbine Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud, its skeleton belongs to ivy type triterpenoid saponin; The invention still further relates to the preparation method of this compound and basic hydrolysis product thereof, and this compound is as the application of prodrug in the preparation antitumor drug.
Description
Technical field
The present invention relates to natural medicine field, be specifically related to a kind of compound of extraction separation from woodbine Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud, its skeleton belongs to ivy type triterpenoid saponin; The invention still further relates to the preparation method of this compound and basic hydrolysis product thereof, and this compound is as the application of prodrug in the preparation antitumor drug.
Background technology
Malignant tumour is one of major disease of serious harm human health.The control of tumour has become the problem of extensively paying attention in the world wide, and the development of antitumor drug also has extremely exigence with exploitation.Plant is the preciousness source of new bioactive molecules, seeks the attention that the new medicine with anti-tumor activity more and more is subjected to medical worker from plant origin.Many cancer therapy drugs from plant, have been isolated, as vincristine(VCR), epipodophyllotoxin glucoside and taxol etc.With respect to the chemicals of synthetic, the effective constituent of these natural origins has obtained a large amount of application with the lower advantage of its toxicity in oncotherapy.
Saponin(e is extensively to be present in the special glycoside of a botanic class, and wherein sapogenin is that the saponin(e of the triterpenes derivative formed of 30 carbon atoms is called triterpenoid saponin.Modern study shows, saponin component has physiologically active widely, except the effect of direct killing and inhibition tumour cell, saponin(e in the transfer of startup, the evolution that delays cancer of enhancing body immunologic function, containment cancer, anticancer, suppress tumor-blood-vessel growth, the many aspects such as result of treatment that improve traditional clinical anticarcinogen have good activity, prompting research and development anti-cancer agent from saponin(e has wide prospect.
Japanese Honeysuckle is the dry flower (2005 version " Chinese pharmacopoeia) of Caprifoliaceae woodbine honeysuckle Lonicerajaponica Thunb., is China's conventional Chinese medicine.Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms is the dry flower of Caprifoliaceae woodbine L.fulvotomentosa Hsu et S.C.Cheng.Its crude drug source is the woodbine novel species of finding in state, the southwest of Guizhou Province in the later stage seventies 20th century, is Chinese endemic plant kind, mainly is distributed in Guizhou, Guangxi, Yunnan San Sheng and aboundresources.Effects such as that the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud has is clearing heat and detoxicating, wind-heat dissipating, the medicinal history more than existing 5 generation people among the people is mainly used in treatment hepatitis, stomach trouble, flu etc., and the effect of relieving the effect of alcohol is arranged.Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms is Guizhou Province's provincial standard kind, is one of regional Japanese Honeysuckle commodity medicinal material main flow kinds such as Guizhou, Guangxi also, and " the Chinese pharmacopoeia [is listed in one of Lonicera confusa DC. medicinal material base source plant to be included into version in 2005.
Be rich in the Hederagenin constituents in the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud, content is up to about 20%.Forefathers find the pharmacological research of Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms total saponins, its have good protect the liver, anti-inflammatory isoreactivity, the particularly liver injury that multiple mechanism of action and different chemical toxicants are caused all have provide protection in various degree.Yet the study of pharmacy to its saponin component is also less, isolation identification Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e first (fulvotomentoside A), sapindoside B (sapindoside B) and α-Hederagenin (three kinds of saponin components of α-hederin), but the content of these several effective constituents in plant is extremely low have only been reported therefrom at present.
Summary of the invention
The present invention utilizes modern separation technology and structure identification of means that the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud is carried out chemical constitution study, therefrom separates obtaining a kind of new Hederagenin Compound I, and this compound content in medicinal material is extremely abundant, and content is up to about 5%.Find that by the anti tumor activity in vitro screening this compound does not show activity, but its basic hydrolysis product has very strong inside and outside anti-tumor activity.Because this new compound aboundresources, hydrolysate is active clear and definite, and technology is simple and easy to do, and efficiency of pcr product and purity height can be used as the prodrug for preparing antitumor activity component, are fit to industrial mass production, and market outlook and exploitation with Guan Kuo are worth.
Compound I structure of the present invention is as follows:
R wherein
1, R
2, R
3In one be xylosyl (Xyl '), two is H in addition.Be glucosyl group (Glc) and wood sugar (Xyl ') can be the 1-2 position, 1-4 position or 1-6 position connect.
Preferred compound is:
Compound III: molecular formula is C
57H
92O
25, its molecular weight is 1176,214～215 ℃ of m p, [α]
D 20-37.35 ° (c 0.5, MeOH).Chemical name: 3-O-β-D-xylopyranosyl (1 → 3)-α-L-rhamnopyranosyl (1 → 2)-α-L-arabopyranose base hederagenin-28-O-β-D-xylopyranosyl (1 → 4)-β-D-glucopyranosyl ester glycosides, called after Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second (fulvotomentoside B).
Compound I of the present invention is the medicine prodrug, and itself does not have activity, but produces the medicine of the activeconstituents that can bring into play the expection drug effect in body by hydrolysis, metabolism, approach such as derive.
Compound of Formula I of the present invention can prepare with following method:
With the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms dry flower is raw material, with the 30-90% alcohol reflux, extracting solution is evaporated to does not have the alcohol flavor, filter or high speed centrifugation, macroporous resin column on filtrate or the centrifuged supernatant is fully after the absorption, with alcohol-water system gradient elution, merge 50-70% ethanol liquid elutriant, evaporated under reduced pressure obtains the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms total saponins.Total saponins is again through silica gel column chromatography, anti-phase C18 post and the further separation and purification of dextrane gel column chromatography, promptly.
More preferably the preparation method is: getting the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms dry flower is raw material, with the 50-90% alcohol reflux, extracting solution is evaporated to does not have the alcohol flavor, filter or high speed centrifugation, after macroporous resin fully adsorbs on filtrate or the centrifuged supernatant, successively water, 30% ethanol, that 70% ethanol liquid is eluted to elutriant is closely colourless, collect 70% ethanol liquid elutriant, evaporated under reduced pressure, obtain the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms total saponins, total saponins is again through silica gel (200-300 order), anti-phase C18 post and the further separation and purification of dextrane gel column chromatography, get final product Compound I.The wherein preferred D101 of macroporous resin, AB-8, HPD100, HPD300 or D1 type macroporous resin.D101 type macroporous resin most preferably.
Compound I can add acetylation reagent and form acetylate, perhaps as required, adds other reagent and forms new derivative, can also utilize the effect of bioactive enzyme, changes link position, changes over 1-4 or 1-2 connection as being connected by 1-6.
Compound I of the present invention, antitumor activity in vitro does not show activity.But Compound I of the present invention can change into the secondary saponin Compound I I with anti-tumor activity by 28 sugar ester keys of basic hydrolysis.
Compound I I: molecular formula is C
46H
74O
16, its molecular weight is 882,224～226 ℃ of m p.Chemical name: hederagenin-3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabopyranose glycosides, i.e. sapindoside B.
Compound I can prepare Compound I I by the method for hydrolysis that those skilled in the art use always, also available following method preparation:
Compound I adds 1～8% potassium hydroxide or aqueous sodium hydroxide solution, and warm or refluxing extraction 2～6h in 40～80 ℃ of water-baths adds sour adjust pH to 4～6 after cold.Use n-butanol extraction again, extraction liquid carries out silica gel column chromatography after reclaiming solvent, uses ethyl acetate: methyl alcohol: the water system wash-out, concentrate, and get white powder Compound I I.Ethyl acetate wherein: methyl alcohol: water preferred volume ratio 5: 1: 0.1.Prove that through pharmacological testing Compound I I has good anti-tumor effect.
Because the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms plant resources is very abundant, and the content of this new compound in the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms bud is up to about 5%, and the source is sufficient; Step by the active secondary saponin II of this compound is easy, 28 sugar ester keys of hydrolysis and do not destroy 3 sugar chains only, overcome the shortcoming of acid hydrolysis products complexity, separation and purification difficulty, purpose is strong, transformation efficiency is high, therefore can be used as prodrug and uses in the preparation antitumor drug.
Be part pharmacology test of the present invention and result below:
One, the external restraining effect of new compound I of the present invention and hydrolysate Compound I I thereof to tumour cell:
1) clone and reagent: human lung cancer cell A549, human cervical carcinoma cell Hela, melanoma cell B16, breast cancer cell MDA-MB-231.The DMEM high glucose medium is available from U.S. Gibco company.Calf serum, non-essential amino acid are available from Hyclone company.Trypsinase, MTT reagent are available from Sigma company.
2) be subjected to the reagent thing: separate obtaining in the bud of Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second (I) by Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms L.fulvotomentosa Hsu et S.C.Cheng.Sapindoside B (II) is prepared by the hydrolysis of Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second.The positive control medicine is Zorubicin (Doxorubicin).
3) cell cultures: 4 kinds of tumour cells all with the DMEM nutrient solution that contains 10% calf serum in 37 ℃, 5%CO
2And cultivate under the saturated humidity condition.The cell in good condition in vegetative period of taking the logarithm is used 0.25% tryptic digestion, makes cell suspension, counts about 5 * 10
4Individual/mL, to inoculate into 96 orifice plates by 5000 the cell obtained cell suspensions in every hole, 100 μ L/ holes place in the cell culture incubator and cultivated 24 hours; The administration group is handled with the Compound I or the II of different concns, and the medicine final concentration is 2,4,8,16,32 μ M/mL.With the negative control group of the nutrient solution that contains 0.02% methyl-sulphoxide,, answer holes for 6 every group simultaneously with the positive control group of Zorubicin.Cultivate after 48 hours, the observation of cell form, every hole adds MTT solution (5mg/mL) 10 μ L, hatch 4 hours under 37 ℃ after, the careful suction abandoned the culture supernatant hole in, every hole adds 100 μ L DMSO, the 3min that vibrates fully dissolves crystallization.Select the 570nm wavelength, on microplate reader, measure each hole absorbance value (OD value), get 3 multiple hole OD value mean numbers, be calculated as follows cell inhibitory rate:
Cell inhibitory rate (%)=(negative control group OD value one is tried thing group OD value)/negative control group OD value * 100%
The results are shown in Table 1, table 1 shows that new compound I of the present invention does not show anti-tumor activity, but the basic hydrolysis product of different concns all possesses stronger growth-inhibiting effect to 4 kinds of cancer cells.
Table 1 new compound I of the present invention and basic hydrolysis product Compound I I thereof are to the ED of different tumor cell lines
50(μ M)
Two, the anti-tumor in vivo pharmacodynamic study of The compounds of this invention II
1) foundation of animal model for tumour: female C57BL/6J mouse, age in 6-8 week, one-level, body weight 18 ± 2g.The solid tumor models that this experiment is set up is the Lewis lung cancer model.Get the tumour cell of exponential phase of growth, after trysinization, wash twice with PBS, it is subcutaneous that cell is subcutaneously injected into C57BL/6J right side of mice back, every mouse inoculation of LLC tumor model 1 * 10
6Individual tumour cell (50 μ l), visible tumor in situ after about 5 days, when treating that diameter of tumor reaches the 5mm left and right sides animal is divided into 5 groups at random, promptly sapindoside B group (being 6 μ M/kg), Zorubicin (Doxorubicin) group and control group (Control) reach more than 8 every group of mouse.Every day, intraperitoneal injection was 1 time, continued 7 days, and control group is in intraperitoneal injection equal-volume PBS.Detect mouse body weight and survival condition simultaneously.
2) medicine sapindoside B (II) is prepared by the basic hydrolysis of Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second.The positive control medicine is Zorubicin (Doxorubicin).
3) measurement of tumor and volume calculation:, measured once, and measured the major diameter (L) and the minor axis (W) of tumour respectively, in per 3 days according to formula V=L * W with vernier caliper measurement mouse Subcutaneous tumor
2* 0.52 calculates gross tumor volume.Be calculated as follows tumour inhibiting rate:
Tumour inhibiting rate=[(the average knurl volume of the average knurl volume-experimental group of control group)/average knurl volume of control group] * 100%
Experimental result is seen Fig. 1.The basic hydrolysis product Compound I I of The compounds of this invention has tangible anti-tumor activity, inhibition rate of tumor growth to the Lewis tumor-bearing mice is 52.7%, be higher than positive control medicine Zorubicin (30.7%), and to the not obviously influence of body weight of tumor-bearing mice, to the also not obviously damage of organ of normal mouse.
The basic hydrolysis product Compound I I of Fig. 1 The compounds of this invention I is to the effect of mouse tumor growth-inhibiting
Embodiment
Embodiment 1
Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms honeysuckle medicinal material (dry flower) 5kg, with 10 times of amount 90%, 80% and 70% each refluxing extraction of ethanol once, each 3h merges No. three times extracting solution respectively, and being evaporated to does not have alcohol; Filter or high speed centrifugation, after macroporous resin fully adsorbs on filtrate or the centrifuged supernatant, successively water, 30% ethanol, that 70% ethanol liquid is eluted to elutriant is closely colourless, collects 70% ethanol liquid elutriant, evaporated under reduced pressure obtains the about 1.5kg in Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms total saponins position.This position medicinal extract dissolve with methanol, add about 1.5kg silica gel (200-300 order) and mix thoroughly, grind, last silica gel column chromatography is with chloroform-methanol system (20: 1,15: 1,10: 1,9: 2,8: 2.5,7: 3.5,1: 1), every 500ml is a flow point, altogether 72 flow points.Concentrating under reduced pressure, enriched product detects through thin-layer chromatography, merges similar flow point, obtains 1-10,11-18,19-25,26-34,35-72 totally five parts (Fraction1-Fraction 5).Get the dissolving of 70g Fraction 4 usefulness 50% methanol-water, last RP-C
18ODS reverse phase silica gel post, 55% methanol-water wash-out is collected 64 flow points, concentrating under reduced pressure, enriched product detects through thin-layer chromatography, merges identical flow point, obtains four parts (FractionA1-D1) altogether.FractionB1 obtains compound III (2.5g) through Sephadex LH-20 post 70% methanol-water wash-out.
Structure elucidation:
Compound III, white amorphous powder, 214～215 ℃ of m p, [α]
D 20-37.35 ° (c 0.5, and MeOH), TLC Vanillin-vitriol oil test solution heating displaing amaranth becomes blueness after several minutes, and Molish reaction and Liebermann-Burchard reaction are all positive, and prompting may be triterpene saponin componds.The thin layer acid hydrolysis: saponin(e takes a morsel, be dissolved in methyl alcohol, put on efficient thin layer plate, place concentrated hydrochloric acid steam 12h, volatilize concentrated hydrochloric acid, going up each monose reference substance again, is that developping agent launches with chloroform-methanol-water (16: 9: 2), uses chloroform-methanol-water (30: 12: 4 again, lower floor, every 9mL adds 1mL acetic acid) the secondary expansion, the colour developing of aniline-phthalic acid solution can detect glucose, pectinose, wood sugar and rhamnosyl.High resolution mass spectrum: 1199.5887[M+Na]
+, in conjunction with
1H NMR,
13C NMR and 2D NMR its molecular formula as can be known are C
57H
92O
25
1H NMR (C
5D
5N, 500MHz) δ: 6.30 (1H, br s), 6.25 (1H, d, J=8.1Hz), 5.31 (1H, d, J=7.6Hz), 5.05 (1H, d, J=6.6Hz), 4.90 (1H, d J=7.1Hz) are followed successively by the anomeric proton signal of rhamnosyl, glucose, wood sugar, pectinose and wood sugar, this result obtains the hsqc spectrum checking, and 5.38 (1H, br s) are 12 alkene hydrogen proton signals, 1.20,1.12,1.10,0.98,0.86,0.84 (each 3H, s) be 6 methyl proton signals, 1.54 (3H, d J=6.2Hz) are 6 methyl proton signals of rhamnosyl.
New saponin(e (III) of table 2 and known compound decaisoside E (IV)
13C NMR composes (C
5D
5N, 125MHz, δ, ppm)
13Show 57 carbon signals among the C NMR altogether, comprise carbon signal on 30 aglycon carbon signals and 27 sugar.Wherein aglycon carbon signal ivy aglycon basically identical, and C-3 position hydroxyl and C-28 carboxyl form disaccharide chain saponin(e all by glycosidation.Carbon signal (table 2) on comparative compound III and the known compound decaisodie E sugar, find the carbon signal unanimity in both C-3 position sugar chains of chemical combination, so infer that Compound I may contain 3-O-β-D-xylopyranosyl (1 → 3)-α-L-rhamnopyranosyl (1 → 2)-α-L-arabopyranose based structures segment; Then there is the chemical shift of one group of sugar to exist in the sugar chain of C-28 position than big-difference, and with document [Kim J.S., Shim S.H., Chae S., et al..Chem.Pharm.Bull.[J], 2005,53 (6): 696-700] chemical shift unanimity in the C-28 position sugar chain of compound 6 in may contain 28-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl ester glycosides structure fragment so infer the I compound.
Comprehensive above the analysis, the structure of compound III is defined as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabopyranose base-hederagenin-28-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl ester glycosides, by literature search, be a new compound, called after Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second (Fulvotomentoside B).
Its chemical structure as shown in the formula:
Embodiment 2
Get 2g Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms saponin(e second, add 5%NaOH solution 20mL,, put coldly, add dense HCL and regulate pH value to 4～5 in 60 ℃ of water-bath refluxing extraction 2h.Adding water-saturated n-butanol solution (1: 1, v/v) extraction is 3 times, merges butanol extraction liquid, and decompression and solvent recovery gets n-butyl alcohol extract to doing.N-butyl alcohol extract is splined on silicagel column, with ethyl acetate: methyl alcohol: water (5: 1: 0.1) wash-out, altogether 45 flow points, with concentrating under reduced pressure, merge wherein 10～40 flow points with rotary evaporation, white powder, be sapindoside B (1.1g).
Claims (6)
1, the saponin compound of following general formula (III):
2, the preparation method of the saponin compound of claim 1 may further comprise the steps:
With the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms dry flower is raw material, use the 30-90% alcohol reflux, extracting solution is evaporated to does not have the alcohol flavor, filters or high speed centrifugation, macroporous resin column on filtrate or the centrifuged supernatant, fully after the absorption,, merge 50-70% ethanol liquid elutriant with ethanol one water system gradient elution, evaporated under reduced pressure, obtain the Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms total saponins, total saponins is again through silica gel column chromatography, anti-phase C18 post and the further separation and purification of dextrane gel column chromatography, promptly.
3, the preparation method of claim 2, wherein macroporous resin is D101, AB-8, HPD100, HPD300 or D1 type macroporous resin.
4, the saponin compound of claim 1 is used to prepare the purposes of antitumor drug (II)
5, the purposes of claim 4, wherein saponin compound prepares antitumor drug (II) by following method: compound III adds 1～8% potassium hydroxide or aqueous sodium hydroxide solution, warm or refluxing extraction 2～6h in 40～80 ℃ of water-baths, add sour adjust pH to 4～6 after cold, use n-butanol extraction again, after extraction liquid reclaims solvent, carry out silica gel column chromatography, use ethyl acetate: methyl alcohol: the water system wash-out, concentrate, promptly get Compound I I.
6, the purposes of claim 5, wherein ethyl acetate: methyl alcohol: water volume ratio is 5: 1: 0.1.
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| CN101406509B (en) * | 2008-11-28 | 2011-08-31 | 江苏省中国科学院植物研究所 | Lonicera confusa extract and preparation method and application thereof |
| WO2011085544A1 (en) * | 2010-01-13 | 2011-07-21 | 安徽辉克药业有限公司 | Compounds which effecttively remove tumor or cancer cell |
| CN102391349B (en) * | 2011-09-23 | 2014-07-02 | 江苏省中国科学院植物研究所 | New honeysuckle lonimacranthoide and preparation method and application thereof |
| CN102627683A (en) * | 2012-03-20 | 2012-08-08 | 苏州世林医药技术发展有限公司 | Triterpenoid saponin compounds with antitumor effects |
| CN104688798B (en) * | 2015-03-24 | 2018-09-21 | 山东省医学科学院药物研究所 | A kind of preparation method and application of rosy clouds grass extract |
| KR102118433B1 (en) * | 2018-05-04 | 2020-06-03 | 백주연 | Composition comprising extract of Anemone raddeana, Lonicera species and Aralia elata including high concentrated saponin of anticancer activity for preventing or treating cancer and producing method the same |
| CN110974834A (en) * | 2019-12-02 | 2020-04-10 | 贵州中医药大学 | Application of Lonicera fulvidraco acid hydrolysate in pharmacy and preparation method thereof |
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| 黄褐毛忍冬化学成分的研究. 茅青等.药学学报，第24卷第4期. 1989 |
| 黄褐毛忍冬化学成分的研究. 茅青等.药学学报，第24卷第4期. 1989 * |
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