CN1508260A - Anti-tumour ginseng saponin preparing method - Google Patents
Anti-tumour ginseng saponin preparing method Download PDFInfo
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Abstract
The invention relates to a method to make enzymolysis or microbe fermentation hydrolyzation on ginsenoside to prepare three hydroxyl dissociative low-polarity ginsenosides: 20-O-beta-D-xylopyranosyl (1->6)-beta-D-glucopyranosyl-20(s)- protopanaxadiol, called Mx for short, 20-O-alpha-L- arabinopyranosyl (1->6)-beta-D-glucopyranosyl- 20(s)-protopanaxadiol, called C-Y for short, and 20-O-alpha-L- arabinofuranosyl (1->6)-beta-D-glucopyranosyl-20(s)- protopanaxadiol, called Mc for short, especially a coarse snail enzymatic hydrolysis preparing method. The technique is simple, the cost is low and the recovery is high.
Description
Technical field:
The present invention relates to the low polarity ginsenoside of 3 hydroxyl free of enzymolysis or microbial fermentation hydrolysis ginsenoside preparation: 20-O-β-D-wood sugar (1 → 6)-β-D-glucose-20 (s)-protopanoxadiol [20-O-β-D-xylopyanosyl (1 → 6)-β-D-glucopyranosyl-20 (S)-protopanaxadiol, be called for short Mx], 20-O-c-L-pectinose (1 → 6)-β-D-glucose-20 (S)-protopanoxadiol [20-O-α-L-arabinopyranosyl (1 → 6)-β-D-glucopyranosyl 20 (S)-protopanaxadiol, be called for short C-Y] and 20-O-α-L-arabinose (1 → 6)-β-D-glucose-20 (S)-protopanoxadiol [20-O-a-L-arabinofuranosyl (1 → 6)-β-D-glucopyranosyl 20 (S)-protopanaxadiol, be called for short the method for McJ, particularly relate to thick helicase hydrolysis preparation method.
Background technology:
Ginsenoside has multiple pharmacodynamic feature, as antitumor and immunomodulatory, microcirculation improvement, adjusting digestive function, calm the nerves, anti-ageing, anti-anxiety, prevention of digestive tract ulcers, raising quality of life, memory and learning capacity etc.But the natural ginseng saponin(e almost can not be absorbed directly into blood by enteron aisle, and the pharmacokinetics behavior is relatively poor.
Recently, successively find the multiple meta-bolites that comes through bio-transformation by the natural ginseng saponin(e: 3 low polarity ginsenosides of hydroxyl free, as C-K, C-Y and Mc.They are proved to be the oral absorption form of corresponding natural ginseng saponin(e respectively.Hasegawa etc. discover that C-K has inducing tumor cell differentiation, inducing apoptosis of tumour cell, inhibition growth of tumour cell at anti-tumor aspect, suppresses multiple biological activitys such as the new vessel formation of tumor inducing, the infiltration of resisting tumour and transfer; In addition, C-K has good pharmacokinetics behavior and nontoxic substantially or toxicity is very low, at present, has entered III phase clinical study in Korea S.Come from natural ginseng saponin(e Rb
2Have the drug activity similar with the meta-bolites C-Y of Rc with Mc to C-K.
Because L does not directly absorb behind natural ginseng or the natural ginseng saponin oral liquor, the above-mentioned three kinds of absorbable meta-bolitess in oral back are being transformed by human enteric bacteria.Because of there is individual difference in the ginsenoside entero-bacte metabolic capacity of body, therefore, in theory, directly use conversion product can avoid malabsorption, make to be easy to grasp effective dose clinically.
The stability of the glycosidic link that ginsenoside is 20 in acidic medium is lower than 3 glycosidic links, and the steric restriction effect makes the glycosidic link vigor of 20 of enzymic hydrolysiss extremely low.Thereby bio-transformation prepares the best approach of the low polarity ginsenoside of 3 hydroxyl free beyond doubt.Bio-transformation comprises enzyme process and microbe fermentation method.
Hasegawa cultivates the natural ginseng saponin(e with the external anaerobism of entero-bacte, separate obtaining C-K, C-Y and Mc from nutrient solution, and applied for United States Patent (USP) (5,919,770).Because when anaerobism is cultivated, 3 low polarity ginsenosides of hydroxyl free are not unique products and feed stock conversion is low, separation and purification is loaded down with trivial details, culture condition is harsh, cost occupies high.Thereby enzyme process is more paid close attention to.
At present, the enzyme process that provides in the document has naringinase and hesperidinase, but this enzyme has following defective: hydrolysis time is long, the consumption of enzyme is big, and the source of enzyme is difficult for, and therefore, is unsuitable for industrial preparation.
Enzymatic-process preparation method (Chinese patent, application number 01133410.X) and the microbial fermentation processes (Chinese patent, application number 02132403.4) of the C-K that all has superiority invented in our previous research on technology and cost.Two technological inventions have multiple advantage than the technology of preparing of entero-bacte and naringinase, hesperidinase.Utilize above-mentioned technology simultaneously, with the ginsenoside Rb that is rich in the notoginseng haulm
3Be raw material, the present inventor has found Mx, and this has the new compound of anti-tumor activity, and Mx has the biological activity similar to C-K, and than genseng, pseudo-ginseng and cauline leaf thereof have more significantly resources advantage in China, and its structural formula is as follows:
The technology contents of invention:
In order to prepare Mx, C-Y and Mc simply, conveniently, low-costly and in high volume, the invention provides and a kind ofly prepare the method that ginsenoside prepares Mx, C-Y or Mc with enzymolysis or microbial fermentation hydrolysis ginsenoside, comprise hydrolysis, collection and enzyme recycling step, it is characterized in that: with Glycosylase difference selective hydrolysis ginsenoside Rb in damping fluid
3Or Folium Notoginseng glycoside, Rb
2, Rc, the weight ratio of saponin(e and Glycosylase is 1: 1～10: 1, temperature is 30～45 ℃, pH 3.0～5.5, hydrolysis time 2～72 hours.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, requires Glycosylase that the hydrolysis of glycosidic link is had good selectivity, i.e. 3 glycosidic links of hydrolysis and do not influence 20 xylosyl and glucosyl group only.Glycosylase can originate commercial enzyme such as helicase, hesperidinase, naringinase etc., also can have the active microorganism of selective glycosidase from the occurring in nature screening and separating, as the spiral Pseudomonas, Campylobacter, gentle curved bar Pseudomonas, Rhodopseudomonas, xanthomonas, lobate Pseudomonas, methyloccccus, how Bordetella, Flavobacterium, Bacteroides, Actinobacillus, bordetella bacillus, paracoccus, enterobacter, proteus, Photobacterium, Leptothrix, amber platinic acid Vibrio, Selenomonas, micrococcus sp, the oral cavity Pseudomonas, enterococcus spp, streptococcus acidi lactici, streptococcus anaerobius, bright beading Coccus, Pediococcus, Peptococcus, Coprecoccus, bacillus, Sporolactobacillus, fusobacterium, lactobacillus, listeria spp belongs to, corynebacterium, genus arthrobacter, brevibacterium sp, the cheese Bacillaceae, Microbacterium, Cellulomonas, excellent Bacillaceae, actinomyces, Mycobacterium, Nocardia, the saccharification Pleospora, preceding small Monosporium, Candida, Penicillium notatum, Eurotium, mucor, genera cryptococcus, candidiasis etc., also available mentioned microorganism has the active biological products of selective glycosidase.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, and easy, the product separation and the purifying of enzyme method technique are easy, are better than the microbial fermentation hydrolysis.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, and the raw material of preparation Mx, C-Y and Mc is respectively ginsenoside Rb
3, Rb
2, Rc, or contain Rb
3, Rb
2, Rc plant, plant milk extract or plant culturing liquid.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, the enzymic activity height of helicase hydrolysis material ginsenoside, strong, the convenient sources, cheap of good, the anti-deactivation of selectivity, the production that is specially adapted to Mx, C-Y and Mc prepares.The optimum temperuture of thick helicase hydrolysis material ginsenoside is 40 ℃, and optimal pH is 4.5, and ionic strength is low more good more, and the kind of damping fluid is little to the enzymic activity influence; The present invention selects pH4.5 for use, and ionic strength is 0.001molL
-1, phosphoric acid-citrate buffer solution; The ratio of raw material and enzyme is the most economical with 6: 1; According to this condition, hydrolysis time surpassed after 8 hours, and the output of Mx no longer changes, and therefore, hydrolysis time was advisable with 8 hours.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, and enzyme reaction solution can be recycled after removing throw out and small molecular weight impurity.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, when screening and separating has the active microorganism of selective glycosidase, adopt enzyme induction method and antibiotics resistance revulsion, with content or the enhancing microbial hydrolytic ability that increases the microorganism Glycosylase, the microbiotic of Jia Ruing can also prevent living contaminants simultaneously.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, and collection process is: (1) enzyme process is collected the enzyme reaction throw out, makes suspension liquid; Ethyl acetate extraction three times, combined ethyl acetate liquid, after the reclaim under reduced pressure ethyl acetate, the resistates of collection is Mx, C-Y or Mc; If raw material is for containing Rb
3, Rb
2With plant, plant milk extract or the plant culturing liquid of Rc, institute's crude product that obtains also needs through purification on adsorbent resins.(2) microbe fermentation method is with water saturated n-butanol extraction substratum three times, merge n-butanol extracting liquid, the gac deodorizing of discoloring, concentrating under reduced pressure reclaims propyl carbinol, and resistates is dissolved in ethyl acetate and with obtaining Mx, C-Y or Mc behind silica gel column chromatography and the reversed phase chromatography purifying.
Enzymic hydrolysis ginsenoside provided by the present invention prepares in the method for Mx, C-Y or Mc, adds certain amount of organic solvent middle product is played the hydrotropy effect, helps normally carrying out of enzymatic hydrolysis reaction.The kind of organic solvent and add-on are as the criterion not influence enzymic activity.Through screening, ethanol the best with 5～15%.
The present invention provides a kind of convenient sources, cheap enzyme for the Panaxadiol saponin enzymolysis prepares ginsenoside Mx, C-Y or Mc, prepares Mx, C-Y and Mc technology is simple and convenient, cost is low, the rate of recovery is high with this enzyme.Use Mx, C-Y and Mc content 〉=95% of present method preparation, aglycon yield 〉=91%.
Embodiment:
Embodiment 1
Ginsenoside Rb
3(pH4.5, ionic strength is 0.001molL (500mg) to be dissolved in 32mL phosphoric acid-citrate buffer solution with helicase (84mg) enzyme
-1, contain 10% ethanol) in, hydrolysis is 1 day in 40 ℃ of water-baths; Centrifugal reaction solution, collecting precipitation, water is made suspension liquid with throw out, ethyl acetate extraction (10mL * 5) suspension liquid, combined ethyl acetate liquid, decompression obtains Mx (106mg) after removing ethyl acetate.
Embodiment 2
Ginsenoside Rb3 (50mg) is dissolved in the different phosphoric acid-citrate buffer solution of 3.2mL, pH with helicase (8.4mg), and (ionic strength is 0.001molL
-1, contain 10% ethanol) in, hydrolysis is 1 day in 40 ℃ of water-baths.Centrifugal reaction solution, collecting precipitation.Water is made suspension liquid with throw out, ethyl acetate extraction (1mL * 5) suspension liquid, and combined ethyl acetate liquid, decompression removes ethyl acetate, and the resistates of collection also is dissolved in the 5.00mL methyl alcohol, HPLC analyzing and testing Mx content.Presentation of results: the helicase optimal pH is 4.5.
Embodiment 3
With ginsenoside Rb
3(pH4.5, ionic strength is 0.001molL to be dissolved in 3.2mL phosphoric acid-citrate buffer solution with helicase by different ratios
-1, contain 10% ethanol) in, hydrolysis is 1 day in 40 ℃ of water-baths; Centrifugal reaction solution, collecting precipitation.Water is made suspension liquid with throw out, ethyl acetate extraction (1mL * 5) suspension liquid, and combined ethyl acetate liquid, after decompression removed ethyl acetate, the resistates of collection also was dissolved in the 5.00mL methyl alcohol, HPLC analyzing and testing Mx content.Presentation of results: the suitableeest raw material/enzyme amount ratio is 6/1.
Embodiment 4
Ginsenoside Rb
3(pH4.5, ionic strength is 0.001molL (50mg) to be dissolved in 3.2mL phosphoric acid-citrate buffer solution with helicase (8.4mg)
-1, contain 10% ethanol) in, hydrolysis is 1 day in the water-bath of differing temps; Centrifugal reaction solution, collecting precipitation.Water is made suspension liquid with throw out, and with ethyl acetate extraction (1mL * 5) suspension liquid, combined ethyl acetate liquid, after decompression removed ethyl acetate, the resistates of collection also was dissolved in the 5.00mL methyl alcohol, HPLC analyzing and testing Mx content.Presentation of results: optimum temperuture is 45 ℃.
Embodiment 5
Ginsenoside Rb
3(50mg) be dissolved in 3.2mL phosphoric acid-citrate buffer solution (pH4.5 contains 10% ethanol) with helicase (8.4mg), change ionic strength, hydrolysis is 1 day in 40 ℃ of water-baths; Centrifugal reaction solution, collecting precipitation.Water is made suspension liquid with throw out, ethyl acetate extraction (1mL * 5) suspension liquid, and combined ethyl acetate liquid, after decompression removed ethyl acetate, the resistates of collection also was dissolved in the 5.00mL methyl alcohol, HPLC analyzing and testing Mx content.Presentation of results: ionic strength is low more good more.
Embodiment 6
Ginsenoside Rb
3(50mg) being dissolved in 3.2mL pH4.5 ionic strength with helicase (8.4mg) is 0.001molL
-1(comprise that 1 is glycine-HCl, 2 is Potassium Hydrogen Phthalate-HCl, and 3 is Na to contain the different damping fluids of 10% alcoholic acid
2HPO
4-citric acid, 4 is citric acid-sodium citrate, 5 is acetic acid-sodium-acetate) in, hydrolysis is 8 hours in 40 ℃ of water-baths; Reaction solution is through centrifugal collecting precipitation; Water is made suspension liquid with throw out; With ethyl acetate extraction (1mL * 5), combined ethyl acetate liquid, after the reclaim under reduced pressure ethyl acetate, the resistates Mx of collection is dissolved in the 5.00mL methyl alcohol, and HPLC analyzes Mx content.Presentation of results: the kind of damping fluid is little to the influence of helicase enzymic activity.
Embodiment 7
Ginsenoside Rb
3(pH4.5, ionic strength is 0.001molL (50mg) to be dissolved in 3.2mL phosphoric acid-citrate buffer solution with helicase (8.4mg)
-1, contain 10% ethanol) in, in 40 ℃ of water-baths, the conversion hydrolysis time.Centrifugal reaction solution, collecting precipitation, water is made suspension liquid with throw out; With ethyl acetate extraction (1mL * 5) suspension liquid, combined ethyl acetate liquid, after decompression removed ethyl acetate, the resistates of collection also was dissolved in the 5.00mL methyl alcohol, HPLC analyzing and testing Mx content.Presentation of results: react after 10 hours, the increment of Mx is little.
Embodiment 8
Through ginsenoside Rb
3What co-cultivation domestication obtained has aspergillus niger (Aspergillus niger v.Tiegh) the YLY bacterial strain solution of anti-varied bacteria growing to tsiklomitsin, before using in Cha Shi liquid nutrient medium (100mL) overnight incubation, choose bacterium colony, import into and contain ginsenoside Rb
3(3%) in the Cha Shi liquid nutrient medium (100mL), 37 degree shaking table cultured continuously 3 days.With water saturation n-butanol extraction nutrient solution three times (10mL * 5), merge n-butanol extracting liquid, gac discolors, deodorizing, decompression removes propyl carbinol, resistates is dissolved in ethyl acetate to carry out silica gel column chromatography (elutriant is chloroform/ethyl acetate/ethanol=60/30/10, the 500mL of lower floor) and reversed phase chromatography purifying (moving phase is 50% ethanol 5L), obtain Mx (515mg), through check content 〉=95%.
Embodiment 9
Ginsenoside Rb
2(pH4.5, ionic strength is 0.001molL (500mg) to be dissolved in 32mL phosphoric acid-citrate buffer solution with helicase (84mg) enzyme
-1, contain 10% ethanol) in, hydrolysis is 1 day in 40 ℃ of water-baths; Centrifugal reaction solution, collecting precipitation, water is made suspension liquid with throw out, ethyl acetate extraction (10mL * 5) suspension liquid, combined ethyl acetate liquid, decompression obtains C-Y (103mg) after removing ethyl acetate.
Embodiment 10
(pH4.5, ionic strength is 0.001molL to Ginsenoside Rc (500mg) with the molten sub-32mL phosphoric acid-citrate buffer solution of helicase (84mg) enzyme
-1, contain 10% ethanol) in, hydrolysis is 1 day in 40 ℃ of water-baths; Centrifugal reaction solution, collecting precipitation, water is made suspension liquid with throw out, ethyl acetate extraction (10mL * 5) suspension liquid, combined ethyl acetate liquid, decompression obtains Mc (105mg) after removing ethyl acetate.
Claims (9)
1, a kind of with the low polarity ginsenoside of 3 hydroxyl free of enzymic hydrolysis panoxadiol type saponin(e preparation: 20-O-β-D-wood sugar (1 → 6)-β-D-glucose-20 (s)-protopanoxadiol [20-O-β-D-xylopyranosyl (1 → 6)-β-D-glucopyranosyl-20 (S)-protopanaxadiol, be called for short Mx], 20-O-α-L-arabinose (1 → 6)-β-D-glucose-20 (S)-protopanoxadiol [20-O-α-L-arabinopyranosyl (1 → 6)-β-D-glucopyranosyl 20 (S)-protopanaxadiol, be called for short C-Y] or 20-O-α-L-arabinose (1 → 6)-β-D-glucose-20 (S)-protopanoxadiol [20-O-α-L-arabinofuranosyl (1 → 6)-β-D-glucopyranosyl 20 (S)-protopanaxadiol, be called for short Mc] method, comprise hydrolysis, product collection and enzyme are recycled step, it is characterized in that: with Glycosylase difference selective hydrolysis ginsenoside Rb in damping fluid
3Or Folium Notoginseng glycoside, Rb
2, Rc, the weight ratio of saponin(e and Glycosylase is 1: 1～10: 1, temperature is 30～45 ℃, pH3.0～5.5, hydrolysis time 2 hours～3 days.
2, according to the described method for preparing Mx, C-Y or Mc with enzymic hydrolysis of claim 1, it is characterized in that: used Glycosylase has good selectivity to glycosidic link, promptly only the glycosidic link of 3 of hydrolysis ginsenosides and do not influence 20 glycosidic link with and subsequent the glycosidic link of xylosyl and glucosyl group, comprise Glycosylase and have the active microorganism of selective glycosidase and have the active biological products of selective glycosidase.
3, prepare the method for Mx, C-Y or Mc according to claim 1 is described with enzymic hydrolysis, it is characterized in that: for Glycosylase or enzyme-microbial preparation, enzyme digestion reaction carries out in the buffered soln of the pH 3.0～5.5 of enzyme:
For microorganism, enzyme digestion reaction or in substratum, carry out, substratum is liquid, semisolid or solid; Culture condition is aerobic, the oxygen of holding concurrently or anaerobic.
4, prepare the method for Mx, C-Y or Mc according to claim 1 is described with enzymic hydrolysis, it is characterized in that: the raw material of preparation Mx, C-Y, Mc is respectively ginsenoside Rb
3, Rb
2, Rc, or contain Rb
3, Rb
2, Rc plant, plant milk extract or with the thing nutrient solution.
5, according to the described method for preparing Mx, C-Y or Mc with enzymic hydrolysis of claim 1, it is characterized in that: used enzyme is a helicase, and the weight ratio of saponin(e and helicase is 1: 1～10: 1, and the pH value is between 2.0～10.0, hydrolysis temperature is 30-60 ℃, hydrolysis time 2～20 hours.
6, prepare the method for Mx, C-Y or Mc according to claim 5 is described with enzymic hydrolysis, it is characterized in that: used enzyme is a helicase, and the weight ratio of saponin(e and helicase is 6: 1, and pH is 4.5, and hydrolysis temperature is 45 ℃, and hydrolysis time is 8 hours.
7, prepare the method for Mx, C-Y or Mc according to claim 1 is described with enzymic hydrolysis, it is characterized in that described collection process is:
(1) enzyme process is collected the enzyme reaction throw out, makes suspension liquid; Ethyl acetate extraction three times, combined ethyl acetate liquid, after the reclaim under reduced pressure ethyl acetate, the resistates of collection is Mx, C-Y or Mc; If raw material is for containing Rb
3, Rb
2With plant, plant milk extract or the plant culturing liquid of Rc, institute's crude product that obtains also needs through purification on adsorbent resins;
(2 microbe fermentation methods are with water saturated n-butanol extraction substratum three times, merge n-butanol extracting liquid, the gac deodorizing of discoloring, concentrating under reduced pressure reclaims propyl carbinol, and resistates is dissolved in ethyl acetate and with obtaining Mx, C-Y or Mc behind silica gel column chromatography and the reversed phase chromatography purifying.
8, prepare the method for Mx, C-Y or Mc according to claim 1 is described with enzymic hydrolysis, it is characterized in that: describedly removed sedimentary enzyme reaction solution, after small molecular weight impurity is removed in ultrafiltration, reclaimed and use as dhdps enzyme.
9, prepare the method for Mx, C-Y or Mc according to claim 1 is described with enzymic hydrolysis, it is characterized in that: contain 5～15% ethanol in the used damping fluid.
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|---|---|---|---|
| CN 02144779 CN1230553C (en) | 2002-12-13 | 2002-12-13 | Anti-tumour ginseng saponin preparing method |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101768619A (en) * | 2010-02-10 | 2010-07-07 | 华侨大学 | Method for preparing rare ginsenoside IH-901 with Rd as substrate |
| CN104894204A (en) * | 2015-05-27 | 2015-09-09 | 金凤燮 | Method for preparing ginseng rare saponin by virtue of microorganism enzymatic conversion of ginsenosid Re |
| CN105163742A (en) * | 2013-05-03 | 2015-12-16 | 株式会社爱茉莉太平洋 | Topical composition for skin containing ginsenoside Y |
| CN105555278A (en) * | 2013-04-24 | 2016-05-04 | 株式会社爱茉莉太平洋 | Topical composition for skin containing gincenoside Mc |
-
2002
- 2002-12-13 CN CN 02144779 patent/CN1230553C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101768619A (en) * | 2010-02-10 | 2010-07-07 | 华侨大学 | Method for preparing rare ginsenoside IH-901 with Rd as substrate |
| CN105555278A (en) * | 2013-04-24 | 2016-05-04 | 株式会社爱茉莉太平洋 | Topical composition for skin containing gincenoside Mc |
| CN105555278B (en) * | 2013-04-24 | 2018-02-23 | 株式会社爱茉莉太平洋 | Dermatologic preparation composition containing ginsenoside Mc |
| CN105163742A (en) * | 2013-05-03 | 2015-12-16 | 株式会社爱茉莉太平洋 | Topical composition for skin containing ginsenoside Y |
| CN105163742B (en) * | 2013-05-03 | 2019-02-12 | 株式会社爱茉莉太平洋 | Dermatologic preparation composition containing ginsenoside Y |
| CN104894204A (en) * | 2015-05-27 | 2015-09-09 | 金凤燮 | Method for preparing ginseng rare saponin by virtue of microorganism enzymatic conversion of ginsenosid Re |
| CN104894204B (en) * | 2015-05-27 | 2018-04-17 | 金凤燮 | The method that microbial enzyme conversion ginsenoside prepares the rare saponin(e of ginseng |
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|---|---|
| CN1230553C (en) | 2005-12-07 |
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Granted publication date: 20051207 Termination date: 20101213 |