CN103539657A - Method for preparing crocetin from cape jasmine - Google Patents
Method for preparing crocetin from cape jasmine Download PDFInfo
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- CN103539657A CN103539657A CN201310508185.2A CN201310508185A CN103539657A CN 103539657 A CN103539657 A CN 103539657A CN 201310508185 A CN201310508185 A CN 201310508185A CN 103539657 A CN103539657 A CN 103539657A
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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Abstract
The invention provides a method for preparing crocetin from cape jasmine. The method comprises the following steps: extracting a cape jasmine raw material; performing enzymolysis on the raw material to obtain powder, and adding mixed enzyme; performing alkali extraction and enzymolysis, adding a reactant sodium hydroxide, stirring and extracting for 1 hour, filtering, separating a coarse product, and refiltering to obtain crocetin with content of over 50 percent; crystallizing to obtain crocetin, adding absolute ethyl alcohol, refluxing for 2 hours, cooling and crystallizing, filtering and baking to obtain the crocetin product with content of over 95 percent. The method can be used for solving the problems of drug shortage and high price of saffron.
Description
Technical field
The present invention relates to the preparation method of the crocetin in a kind of cape jasmine source.
Background technology
Crocetin is one of effective constituent of Stigma Croci column cap, has unsaturated conjugated polyenoic acid structure, belongs to carotenoids.Crocetin has reduction cholesterol, tumor growth suppression, the different physiological roles such as liver poisoning inhibitor.In addition, crocetin is skin singlet oxygen scavenging agent, the synthetic stimulant of collagen and skin immunization promotor, and all these has the highly purified crocetin of needs.But Stigma Croci column cap output is extremely low, and its resource is extremely limited, in China, is difficult to commerial growing, causes its expensive being described as " plant gold ".
The dry mature fruit of traditional Chinese medicine cape jasmine is containing abundant yellow pigment, and its main component is crocin (Crocin) and crocetin (Crocetin), therefore, can consider to prepare high purity crocetin from cape jasmine, to replace Stigma Croci.
Patent application 201110417356.1 discloses a kind of method of preparing crocetin and crocin.The method comprises prepares cape jasmine fruit extracting solution, the concentrated medicinal extract that obtains of extracting solution under Ultrasonic Conditions with ethanol.Medicinal extract is dissolved in Aqueous Solutions of Polyethylene Glycol, then with solvent, carries out selective extraction and obtains crocetin and crocin.The method selective extraction obtains crocetin and crocin, uses organic reagent more, and environmental pollution is larger, and what obtain is the mixture of crocetin and crocin, and crocetin purity is on the low side.
Patent application 20091009785.9 disclose a kind of from fruit, style and stigma of Saffron Crocus and the style and stigma of Saffron Crocus tissue culture of madder wort Gardenia Ellis (narrow leaf cape jasmine, spoon leaf cape jasmine, Hainan cape jasmine, large Yellow Fructus Gardeniae, cape jasmine) plant the method for high efficiency separation crocetin.Gardenia Ellis fruit (style and stigma of Saffron Crocus and style and stigma of Saffron Crocus tissue culture) by after acid extraction pigment or raw material directly use potass extraction, after the acidifying of water liquid, be extracted with ethyl acetate and obtain crocetin crude product, crude product obtains crocetin sterling with different solvents recrystallization.This method crocetin yield is low, fails the crocin in cape jasmine raw material to change into crocetin, and raw material availability is low; And will be extracted with ethyl acetate in process, ethyl acetate has greater environmental impacts, and toxicity is larger.
Patent application 200710001116 discloses a kind of method of preparing crocetin of extracting from cape jasmine, cape jasmine is pulverized through distilled water or the ultrasound-enhanced extraction of ethanolic soln, concentrated or after the separated cape jasmine glycoside of macroporous resin material, crocin elutriant is concentrated after extracting liquid filtering, acid hydrolysis or basic hydrolysis (alkaline hydrolyzate need be adjusted pH to acid), centrifugal, water washing and precipitating obtains crocetin crude product; Be further purified crocetin crude product, trans-crocetin is separated with cis crocetin, obtain highly purified trans-crocetin; Highly purified trans-crocetin is convenient to carry out structural modification, forms the crocetin derivative of different water-soluble and drug effect features, thereby supplies raw materials for relevant preparation research and development and application.In this method, carried out macroporous resin adsorption, increased solvent consumption and environmental pollution, and can make original crocetin in cape jasmine raw material have partial loss, raw material availability is low.
Summary of the invention
The invention provides the preparation method of the crocetin in a kind of cape jasmine source, to solve Stigma Croci medicinal material problem in short supply, expensive.
The solution that the present invention provides is:
A preparation method for the crocetin in source, comprises the following steps:
(1) extract: cape jasmine raw material, with 8-10 times of 70% extraction using alcohol, the concentrated rear spraying of extracting solution is dry, and powder is standby;
(2) enzymolysis: the above-mentioned powder that makes, add 3-5 times of water gaging and 1-1.5% mixed enzyme, at 40-45 ℃, under pH5-5.5 condition, enzymolysis is 24 hours; Described mixed enzyme is that plant essence is carried prozyme SPE-005, plant essence carries prozyme SPE-007A and aspergillus niger mixes with 1:1:3 ratio;
(3) alkali is carried: after enzymolysis, add the sodium hydroxide solution that reactant 4-5 doubly measures, mass concentration is 1%, 70 ℃ are stirred extraction 1h, filter, after filtering, alkali lye is neutralized to ph3-4 with diluted acid, has thick product and separates out, again filter, obtain more than 50% crocetin of content;
(4) crystallization: the crocetin that step (3) is obtained, add 15-20 doubly to measure dehydrated alcohol, 80 ℃ are refluxed 2 hours, cool crystallization, obtain the more than 95% crocetin product of content after filtering drying.
Based on above-mentioned general planning, the present invention also does following optimization and limits and improve:
In step (1), with the 70%(V/V of 8 times of quality) extraction using alcohol 2 times, united extraction liquid.
In step (3), adopt diluted acid to adopt dilute hydrochloric acid.
In step (3), in reactant, add the sodium hydroxide solution of 5 times of amounts 1%.
The present invention can obtain high-content crocetin, and there is lack of raw materials, expensive problem to have solved Stigma Croci.This law is directly dry through hydrous alcohol extraction concentrated spray, then through enzymolysis, Crocin is changed into trans-crocetin, then with buck, crocetin is extracted, and specifically has following advantage:
1, reduced the organic reagent pollution that solvent extration is used, environmentally friendly, 2, do not use macroporous resin, just reduced organic solvent usage quantity, shorten operation, reduce costs, 3, the most important thing is that we can all extract the crocetin in cape jasmine raw material and crocin to change into crocetin, improved greatly the yield of crocetin, improved raw material availability.
Embodiment
Below in conjunction with embodiment, the present invention is described in detail.
Embodiment 1: the preparation method of a kind of cape jasmine source crocetin, comprises the following steps successively.
1, extract: cape jasmine fruit 100g, with 8 times of amount 70% extraction using alcohols 2 times, merge, be concentrated into without alcohol taste, spraying is dried, and obtains powder 18.6g.
2, enzymolysis: above-mentioned powder, adds 3 times of water, 1% mixed enzyme (SPE-005, SPE-007A, aspergillus niger, ratio 1:1:3).At 45 ℃, under ph5 condition, enzymolysis is 24 hours.Wherein, SPE-005 mainly contain cellulase, polygalacturonase, have zytase concurrently, B-dextranase; SPE-007A mainly contains B-glucuroide, has rhamnosidase, zytase, B-dextranase, cellulase, hemicellulase concurrently.
3, alkali is carried: after enzymolysis completes, add the sodium hydroxide solution of 5 times of amounts 1% in reactant, 70 ℃ are stirred extraction 1h, filter, after filtering, alkali lye is neutralized to ph3-4 with dilute hydrochloric acid, has thick product and separates out, centrifuging, centrifugation is dried, and obtains the crocetin 0.78g of content 52.8%.
4, crystallization: take crocetin 0.6g in above-mentioned 3, add 12ml dehydrated alcohol, 80 ℃ are refluxed 2 hours, filtered while hot, filtrate cools crystallization, obtains 0.28g, 98.4% crocetin product.
Embodiment 2: the preparation method of a kind of cape jasmine source crocetin, comprises the following steps successively.
1, extract: cape jasmine fruit 200g, with 8 times of amount 70% extraction using alcohols 2 times, merging, is concentrated into without alcohol taste, dusts, and obtains powder 37.8g.
2, enzymolysis: above-mentioned powder, adds 5 times of water, 1.5% mixed enzyme (SPE-005, SPE-007A, aspergillus niger, ratio 1:1:3).At 40 ℃, under ph5.2 condition, enzymolysis is 24 hours.
3, alkali is carried: after enzymolysis completes, add the sodium hydroxide solution of 5 times of amounts 1% in reactant, 70 ℃ are stirred extraction 1h, filter, after filtering, alkali lye is neutralized to ph3-4 with dilute hydrochloric acid, has thick product and separates out, centrifuging, centrifugation is dried, and obtains the crocetin 1.55g of content 53.3%.
4, crystallization: take crocetin 1.5g in above-mentioned 3, add 25ml dehydrated alcohol, 80 ℃ are refluxed 2 hours, filtered while hot, filtrate cools crystallization, obtains 0.71g, 96.7% crocetin product.
Embodiment 3: the preparation method of a kind of cape jasmine source crocetin, comprises the following steps successively.
1, extract: cape jasmine fruit 200g, with 10 times of amount 70% extraction using alcohols 2 times, merging, is concentrated into without alcohol taste, dusts, and obtains powder 38.4g.
2, enzymolysis: above-mentioned powder, adds 5 times of water, 1.5% mixed enzyme (SPE-005, SPE-007A, aspergillus niger, ratio 1:1:3).At 45 ℃, under ph5.5 condition, enzymolysis is 24 hours
3, alkali is carried: after enzymolysis completes, add the sodium hydroxide solution of 5 times of amounts 1% in reactant, 70 ℃ are stirred extraction 1h, filter, after filtering, alkali lye is neutralized to ph3-4 with dilute hydrochloric acid, has thick product and separates out, centrifuging, precipitation is dried, and obtains 52.3% crocetin 1.69g.
4, crystallization: take crocetin 1.65g in above-mentioned 3, add 30ml dehydrated alcohol, 80 ℃ are refluxed 2 hours, filtered while hot, filtrate cools crystallization, obtains 0.68g, 97.8% crocetin product.
Claims (4)
1. a preparation method for the crocetin that cape jasmine is originated, comprises the following steps:
(1) extract: cape jasmine raw material, with 8-10 times of 70% extraction using alcohol, the concentrated rear spraying of extracting solution is dry, and powder is standby;
(2) enzymolysis: the above-mentioned powder that makes, add 3-5 times of water gaging and 1-1.5% mixed enzyme, at 40-45 ℃, under pH5-5.5 condition, enzymolysis is 24 hours; Described mixed enzyme is that plant essence is carried prozyme SPE-005, plant essence carries prozyme SPE-007A and aspergillus niger mixes with 1:1:3 ratio;
(3) alkali is carried: after enzymolysis, add the sodium hydroxide solution that reactant 4-5 doubly measures, mass concentration is 1%, 70 ℃ are stirred extraction 1h, filter, after filtering, alkali lye is neutralized to ph3-4 with diluted acid, has thick product and separates out, again filter, obtain more than 50% crocetin of content;
(4) crystallization: the crocetin that step (3) is obtained, add 15-20 doubly to measure dehydrated alcohol, 80 ℃ are refluxed 2 hours, cool crystallization, obtain the more than 95% crocetin product of content after filtering drying.
2. the preparation method of the crocetin in cape jasmine according to claim 1 source, is characterized in that: in step (1), and with 70% extraction using alcohol of 8 times of quality 2 times, united extraction liquid.
3. the preparation method of the crocetin in cape jasmine according to claim 1 source, is characterized in that: in step (3), adopt diluted acid to adopt dilute hydrochloric acid.
4. the preparation method of the crocetin in cape jasmine according to claim 1 source, is characterized in that: in step (3), add the sodium hydroxide solution of 5 times of amounts 1% in reactant.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104480154A (en) * | 2014-12-30 | 2015-04-01 | 成都普思生物科技有限公司 | Method for separating and purifying crocetin monomer from crocus sativus |
| CN106360181A (en) * | 2016-08-31 | 2017-02-01 | 四川百顺药业有限公司 | Cape jasmine fruit drink and preparation method thereof |
| CN106905145A (en) * | 2017-04-07 | 2017-06-30 | 云南省药物研究所 | A kind of preparation method of high-purity crocetin |
| CN115385788A (en) * | 2022-08-28 | 2022-11-25 | 浙江工业大学 | Solvent-free preparation method of crocetin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100210572A1 (en) * | 2009-02-18 | 2010-08-19 | Thomas Eidenberger | Hydrolysate of crocin |
| CN101974571A (en) * | 2010-07-26 | 2011-02-16 | 南京泽朗农业发展有限公司 | Method for preparing crocetin from jasmine |
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2013
- 2013-10-24 CN CN201310508185.2A patent/CN103539657B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100210572A1 (en) * | 2009-02-18 | 2010-08-19 | Thomas Eidenberger | Hydrolysate of crocin |
| CN101974571A (en) * | 2010-07-26 | 2011-02-16 | 南京泽朗农业发展有限公司 | Method for preparing crocetin from jasmine |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104480154A (en) * | 2014-12-30 | 2015-04-01 | 成都普思生物科技有限公司 | Method for separating and purifying crocetin monomer from crocus sativus |
| CN106360181A (en) * | 2016-08-31 | 2017-02-01 | 四川百顺药业有限公司 | Cape jasmine fruit drink and preparation method thereof |
| CN106905145A (en) * | 2017-04-07 | 2017-06-30 | 云南省药物研究所 | A kind of preparation method of high-purity crocetin |
| CN115385788A (en) * | 2022-08-28 | 2022-11-25 | 浙江工业大学 | Solvent-free preparation method of crocetin |
| CN115385788B (en) * | 2022-08-28 | 2024-03-26 | 浙江工业大学 | Solvent-free preparation method of crocetin |
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