CN101250188B - Technique for preparing willow leaf tabersonine - Google Patents
Technique for preparing willow leaf tabersonine Download PDFInfo
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- CN101250188B CN101250188B CN2008100177896A CN200810017789A CN101250188B CN 101250188 B CN101250188 B CN 101250188B CN 2008100177896 A CN2008100177896 A CN 2008100177896A CN 200810017789 A CN200810017789 A CN 200810017789A CN 101250188 B CN101250188 B CN 101250188B
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Abstract
The invention relates to a preparation method of plant extract, in particular to a preparation method of willow leaf tabersonine, which can resolve the problems of prior art such as complex process, long production period and low product yield. The preparation method comprises 1, material pretreatment: breaking and drying seeds, 2, heating, refluxing, extracting and acidifying, 3, purifying on column, 4, alkalizing, extracting, washing hexane layer via water and removing solvent to obtain the product. The preparation method has the advantages of simple chemical process, low environment pollution, high safety, short production period, support for large-scale industrial production, simple process, high controllability and high product yield, wherein unit kilogram of Africa potato can produce at least 98% willow leaf tabersonine whose yield is higher than 1.6%.
Description
Affiliated field:
The present invention relates to the preparing technical field of plant milk extract, be specifically related to a kind of preparation technology of willow leaf tabersonine.
Background technology:
Willow leaf tabersonine (Tabersonine, CAS NO.4429-63-4) from phlox willow leaf Amsonia Amsonia tabemaemontana Walt. (=A.salicifolia) extract leaf, Vinca Cantharanthusroseus (L.) G.Don seed, oval leaf Amsonia Amsonia elliptica Roem.Et Schult. seed or the African Wo Kanjia tree Voacango africana Stapf seed.Its chemical name is Aspidospermidine-3-carboxylic acid, 2,3,6, and 7-tetradehydro-(5 α, 12 β, 19 α)-methylseter, molecular formula is C
21H
24N
2O
2, molecular weight is 336.42.Its physical condition is an oily liquids, and its hydrochloride (ethanol) fusing point is 199～199.5 ℃, [α]
D 25-333 ° (C=2.5, methyl alcohol),
13C-NMR: δ 5.75 (2H, spike, two olefinic protons).Willow leaf tabersonine, mainly be to be used for synthetic a kind of cancer therapy drug at present: vinpocetin, simultaneously through the animal pharmacology experiment confirm, it has tangible hypotensive activity.
In patent technology (US3758478), disclosed technical scheme comprises solvent extraction, extraction, crystallisation step repeatedly, the problem that this scheme exists is: 1, need to use noxious solvents such as a large amount of benzene, chloroform to extract repeatedly, and the chemical step complexity, the production cycle is long; 2, owing to complex steps, repeatedly sour water extraction, product loss is big; Adopt acid alcohol solvent crystallization purifying, crystallization yield is low, and per kilogram Africa Voacanga raw material can only obtain 75%～85% willow leaf tabersonine crude product 20g; Through crystallization, re-crystallization step, can only obtain about 5g willow leaf tabersonine crystal of hydrochloride.
Summary of the invention
The present invention will provide a kind of preparation technology of tabersonine, to overcome the problem that complex process, production cycle are long and product yield is low that prior art exists.
In order to overcome the problem that prior art exists, technical scheme provided by the invention is: a kind of preparation technology of tabersonine, and comprise the steps one, raw materials pretreatment successively: seed is pulverized the back dry for standby; Two, heating and refluxing extraction, acidifying: use organic solvent extraction, merge vat liquor, remove organic solvent, organic solvent is reclaimed in acidifying, and acid liquid is standby; Three, go up column purification: crossing macroporous adsorbent resin, wash with water assortedly, is 60～90% methyl alcohol or alcoholic acid aqueous solution wash-out product again with mass ratio, and elutriant is concentrated standby; Four, alkalization, extraction: regulate the concentration of wash-out concentrated solution, regulating PH with strong aqua is 9～11, divides extraction for several times with normal hexane or sherwood oil, washes the normal hexane layer then with water, desolventize product.
When organic solvent was normal hexane or sherwood oil in the step 2, refluxing extraction 3～5 times merged vat liquor, and concentrate and remove organic solvent, be 0.5～1.5% aqueous hydrochloric acid washing with mass ratio, the recovery organic solvent, acid liquid is standby.
When organic solvent was a mass ratio more than or equal to 80% methyl alcohol or aqueous ethanolic solution in the step 2, refluxing extraction 3～5 times merged vat liquor, concentrate and remove organic solvent, the adding mass ratio is 0.5～1.5% aqueous hydrochloric acid, reclaims organic solvent, and acid liquid is standby.Functional quality is more best than the alcohol solution net effect that equals 80%.
Macroporous adsorbent resin is D101 resin, XDA-6 resin or XDA-7 resin in the step 3.Wherein most economical with the D101 resin, and effect is best.
Compared with prior art, advantage of the present invention is:
1, chemical step is simple, and environmental pollution is little, and security is good, and is with short production cycle, the suitable large-scale industrial production that carries out;
2, process is simple, controllability height, product yield height, per kilogram Africa Voacanga raw material can obtain content greater than 98%, yield is greater than 1.6% willow leaf tabersonine.
Description of drawings:
Fig. 1 is the process flow sheet of prior art;
Fig. 2 is a schema of the present invention.
Embodiment:
Fig. 1 and Fig. 2 are respectively prior art and schema of the present invention, below in conjunction with accompanying drawing the present invention are explained.
Embodiment 1:
A kind of preparation technology of willow leaf tabersonine comprises the steps successively,
One, raw materials pretreatment: African Voacanga fruit maturation or be about to results when ripe, drying is pulverized, and crosses 40 mesh sieve dry for standby;
Two, refluxing extraction: get 200 gram seed powder, use 50 ℃ of refluxing extraction of normal hexane three times of 4 times, 3 times, 3 times volumes respectively, each 1 hour.Filter, merging filtrate is that 1% aqueous hydrochloric acid 750ml divides washing normal hexane layer three times with mass ratio, reclaims organic solvent, and the merging acid liquid is standby;
Three, go up column purification: select the D101 macroporous adsorbent resin for use, acid liquid is directly gone up sample, and washing is mixed, and is 80% ethanol elution product with mass ratio, and the elutriant concentrating under reduced pressure is removed ethanol;
Four, alkalization, extraction: add 200ml water in the concentrated solution and regulate concentration, regulate about pH=10, divide three extractions with the 300ml normal hexane with strong aqua, 100ml water washing normal hexane layer, concentrating under reduced pressure is removed normal hexane, gets content greater than 98% willow leaf tabersonine 3.4g, yield 1.7%.
Embodiment 2:
A kind of preparation technology of willow leaf tabersonine comprises the steps successively,
One, raw materials pretreatment: African Voacanga fruit maturation or be about to results when ripe, drying is pulverized, and crosses 50 mesh sieve dry for standby;
Two, refluxing extraction: getting 200 gram seed powder, is 60～70 ℃ of refluxing extraction of methanol aqueous solution of 80% three times with the mass ratio of 4 times, 3 times, 4 times volumes respectively, is respectively 1 hour, 1.5 hours and 1 hour.Filter, merging filtrate, being evaporated to does not have pure hiding, and the adding mass ratio is 1.5% aqueous hydrochloric acid 500ml, and is standby;
Three, go up column purification: select the XDA-6 macroporous adsorbent resin for use, acid liquid is directly gone up sample, and washing is mixed, and is 90% the ethanol aqueous wash product of being temporarily released from one's regular work with mass ratio, and the elutriant concentrating under reduced pressure is removed ethanol;
Four, alkalization, extraction: add 200ml water in the concentrated solution, regulate PH=9, extract at twice with the 350ml normal hexane with strong aqua, 120ml water washing normal hexane layer, concentrating under reduced pressure is removed normal hexane, gets content greater than 98% willow leaf tabersonine 3.2g, yield 1.6%.
Embodiment 3:
A kind of preparation technology of willow leaf tabersonine comprises the steps successively,
One, raw materials pretreatment: African Voacanga fruit maturation or be about to results when ripe, drying is pulverized, and crosses 50 mesh sieve dry for standby;
Two, refluxing extraction: getting 200 gram seed powder, is 70 ℃ of refluxing extraction of aqueous ethanolic solution of 90% three times with the mass ratio of 3 times, 2.5 times, 2.5 times volumes respectively, is respectively 1 hour, 50 minutes and 1 hour.Filter, merging filtrate, being evaporated to does not have the alcohol flavor, and the adding mass ratio is 0.5% aqueous hydrochloric acid 500ml, and is standby;
Three, go up column purification: select the XDA-7 macroporous adsorbent resin for use, acid liquid is directly gone up sample, and washing is assorted, and the ethanol elution product with 60%, elutriant concentrate removes ethanol;
Four, alkalization, extraction: add 200ml water in the concentrated solution, regulating PH with strong aqua is 11, extracts at twice with the 250ml normal hexane, 100ml water washing normal hexane layer, concentrating under reduced pressure is removed normal hexane, gets content greater than 98% willow leaf tabersonine 3.5g, yield 1.75%.
Embodiment 4:
A kind of preparation technology of willow leaf tabersonine comprises the steps successively,
One, raw materials pretreatment: African Voacanga fruit maturation or be about to results when ripe, drying is pulverized, and crosses 50 mesh sieve dry for standby;
Two, refluxing extraction: get 200 gram seed powder, use 60～70 ℃ of refluxing extraction of 95% aqueous ethanolic solution 5 times of 4 times, 3 times, 3 times, 2 times, 2 times volumes respectively, it is respectively 1 hour, 1.5 hours, 1.5 hours, 1 hour, 1 hour, filter, merging filtrate, being evaporated to does not have the alcohol flavor, and the adding mass ratio is 1.0% aqueous hydrochloric acid 500ml, and is standby;
Three, go up column purification: select the D101 macroporous adsorbent resin for use, after the pre-treatment, acid liquid is directly gone up sample, and washing is assorted, the ethanol elution product with 80%, and the elutriant concentrating under reduced pressure is removed ethanol;
Four, alkalization, extraction: add 200ml water in the concentrated solution, regulate PH=l0, divide three extractions with the 300ml normal hexane with strong aqua, 100ml water washing normal hexane layer, normal hexane is removed in decompression, gets content greater than 98% willow leaf tabersonine 3.6g, yield 1.8%.
Embodiment 5:
A kind of preparation technology of willow leaf tabersonine comprises the steps successively,
One, raw materials pretreatment: African Voacanga fruit maturation or be about to results when ripe, drying is pulverized, and crosses 40 mesh sieve dry for standby.
Two, refluxing extraction: get 200 gram seed powder, use 70～80 ℃ of refluxing extraction of sherwood oil three times of 4 times, 3 times, 3 times volumes respectively, each 1 hour.Filter, merging filtrate is that 1.5% aqueous hydrochloric acid 750m1 divides the washing hexane layer three times with mass ratio, and combining water layer reclaims organic solvent, and the merging acid liquid is standby;
Three, go up column purification: select the D101 macroporous adsorbent resin for use, acid liquid is directly gone up sample, and washing is assorted, and with 80% ethanol elution product, the elutriant concentrating under reduced pressure is removed ethanol;
Four, alkalization, extraction: add 200ml water in the concentrated solution, regulate about PH=10, divide three extractions with the 300ml normal hexane with strong aqua, 100ml water washing normal hexane layer, normal hexane is removed in decompression, gets content greater than 98% willow leaf tabersonine 3.3g, yield 1.65%.
Claims (4)
1. the preparation technology of a willow leaf tabersonine comprises the steps successively, and one, raw materials pretreatment: the seed of African Ma Lingguo is pulverized the back dry for standby; Two, heating and refluxing extraction, acidifying: use organic solvent extraction, merge vat liquor, remove organic solvent, organic solvent is reclaimed in acidifying, and acid liquid is standby; Three, go up column purification: crossing macroporous adsorbent resin, wash with water assortedly, is 60～90% methyl alcohol or alcoholic acid aqueous solution wash-out product again with mass ratio, and elutriant is concentrated standby; Four, alkalization, extraction: regulate the concentration of wash-out concentrated solution, regulating pH with strong aqua is 9～11, divides extraction for several times with normal hexane, washes the normal hexane layer then with water, desolventize product.
2. the preparation technology of a kind of willow leaf tabersonine as claimed in claim 1, it is characterized in that: when organic solvent is normal hexane or sherwood oil in the step 2, refluxing extraction 3～5 times, merge vat liquor, concentrate and remove organic solvent, with mass ratio is the washing of 0.5～1.5% aqueous hydrochloric acid, reclaims organic solvent, and acid liquid is standby.
3. the preparation technology of a kind of willow leaf tabersonine as claimed in claim 1, it is characterized in that: when organic solvent is a mass ratio more than or equal to 80% methyl alcohol or aqueous ethanolic solution in the step 2, refluxing extraction 3～5 times, merge vat liquor, concentrate and remove organic solvent, the adding mass ratio is 0.5～1.5% aqueous hydrochloric acid, reclaims organic solvent, and acid liquid is standby.
4. as the preparation technology of claim 1,2 or 3 described a kind of willow leaf tabersonines, it is characterized in that: macroporous adsorbent resin is D101 resin, XDA-6 resin or XDA-7 resin in the step 3.
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| CN2008100177896A CN101250188B (en) | 2008-03-25 | 2008-03-25 | Technique for preparing willow leaf tabersonine |
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| CN2008100177896A CN101250188B (en) | 2008-03-25 | 2008-03-25 | Technique for preparing willow leaf tabersonine |
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| CN101250188B true CN101250188B (en) | 2011-05-11 |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102477035B (en) * | 2010-11-23 | 2014-12-10 | 成都合盛生物技术有限公司 | Cleaning process for extracting and purifying tabersonine from voacango Africana stapf seeds |
| CN102060856B (en) * | 2010-12-21 | 2012-10-03 | 天医堂(厦门)生物工程有限公司 | Method for extracting tabersonine from voacanga seeds |
| CN102050822B (en) * | 2010-12-28 | 2012-05-30 | 陕西嘉禾植物化工有限责任公司 | Method for extracting tabersonine from voacanga seed |
| CN102250092B (en) * | 2011-08-18 | 2013-01-09 | 张家口市格瑞高新技术有限公司 | Preparation process of alkaloid tabersonine |
| CN102816160A (en) * | 2012-05-25 | 2012-12-12 | 苏州科技学院 | New technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf based on enzymatic hydrolysis |
| CN102746303A (en) * | 2012-06-21 | 2012-10-24 | 永州市鑫盈建材有限公司 | Method for extracting effective component of Voacanga seed |
| CN103554309B (en) * | 2013-11-07 | 2016-03-30 | 中南大学 | A kind of resin for tabersonine separation and purification and application thereof |
| CN103588774B (en) * | 2013-11-26 | 2015-07-08 | 重庆启哲生物科技有限公司 | Clean technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf |
| CN106397438B (en) * | 2016-09-23 | 2018-06-01 | 成都合盛生物技术有限公司 | The method that Aspidospermidine-3-carboxylic acid,2,3,6,7-tetradehydro-(5ALPHA,12BETA,19ALPHA)-methylseter is extracted from Voacanga |
| CN108341716A (en) * | 2018-04-02 | 2018-07-31 | 青岛元汇丰企业管理咨询服务有限公司 | A kind of antibacterial growth-promoting elongated biological pesticide of plant source |
| CN108484603B (en) * | 2018-04-02 | 2020-06-09 | 太阳树（厦门）生物工程有限公司 | Method for extracting tabersonine from African voacanga |
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