CN101029066A - Method for extracting genipin and geniposide from gardenia jasminoides - Google Patents
Method for extracting genipin and geniposide from gardenia jasminoides Download PDFInfo
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- CN101029066A CN101029066A CN 200710090208 CN200710090208A CN101029066A CN 101029066 A CN101029066 A CN 101029066A CN 200710090208 CN200710090208 CN 200710090208 CN 200710090208 A CN200710090208 A CN 200710090208A CN 101029066 A CN101029066 A CN 101029066A
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Abstract
A process for preparing geniposide and genipin from capejasmine fruit includes such steps as extracting, concentrating, chromatography, and freeze-drying to obtain geniposide, or extracting, concentrating, enzymolyzing, chromatography, and freeze- drying to obtain genipin.
Description
Technical field
The present invention relates to a kind of preparation method who from cape jasmine, extracts Geniposide and genipin, specifically, relate to a kind of Geniposide that from cape jasmine, obtains, further again, Geniposide is converted into the preparation method of genipin.
Background technology
Cape jasmine is the fruit of Rubiaceae (Rubiaceae) plant cape jasmine (Gardenia jasminoidesEllis), and oblong or ellipse are scarlet or yellowish red color.The first batch of food and medicament dual-purpose resource of Gardenia Ellis Ministry of Health promulgation is a traditional Chinese medicine." (Compendium of Materia Medica) " is documented: cape jasmine has cholagogic and protects the liver, and is clearing heat and detoxicating, effects such as step-down and antisepsis and anti-inflammation.Be used for the treatment of icterohepatitis on the tcm clinical practice, sprain and contusion, hypertension, diabetes etc.Chemical ingredients in the cape jasmine is a lot, and its main component has Crocin, trans-crocetin (Ichietal) and Geniposide iridoids such as (Geniposide), and wherein Geniposide is its main effective constituent, and its structural formula as shown in Figure 1.It is one of activeconstituents of traditional Chinese medicine cape jasmine that Geniposide (Geniposide) belongs to the iridoid compound, and genipin (Genipin) decomposes back separation purification by Geniposide and obtains, and its structural formula as shown in Figure 2.The genipin main application has: genipin can react with amino acid or protein, generates a kind of gardenia blue pigment, and this natural pigment is used to the making of food dye owing to its nontoxicity; In addition, genipin also is used to the immobilization and the preparation gel microcapsule of enzyme; Perhaps as other chemical substance such as polymer, the synthetic needed raw material of chirality enantiomorph; The utilization of genipin aspect medical science: as pharmaceutical natural linking agent; Also there is the bibliographical information genipin that the prevention dementia that causes of wound and the dysmnesia of age ageing are arranged; Genipin also has anti thrombotic action and suppresses the apoptosis effect; According to the foreign literature latest report, genipin also has hypoglycemic activity.In a word, genipin is widely used, and has potentiality to be exploited, has vast market prospect and utility value.
At present, not about from cape jasmine, extracting the document of genipin, has only the data of from the waste liquid behind cape jasmine dry fruit or the extraction Gardenia Yellow, extracting Geniposide, the general organic solvents such as chloroform, dehydrated alcohol that adopt extract in the Soxhlet extraction flask, obtain activeconstituents Geniposide total in the cape jasmine, again with organic solvent degreasings such as activated carbon decolorizing, ethyl acetate, concentrated, and then go up silicagel column and separate, with a certain proportion of methyl alcohol, chloroform mixed solution wash-out, elutriant carries out recrystallization, filtration in acetone, obtain the Geniposide crystal.Adopt this class methods to extract that effective constituent has certain limitation in natural product, the compound productive rate of its resulting separation is lower, purity is not high, the easy inactivation of activeconstituents, and the use of a large amount of organic solvents easily causes environmental pollution, increase the input of safety in production, thereby caused the raising of cost.
Summary of the invention
The object of the present invention is to provide a kind of preparation method who from cape jasmine, extracts Geniposide and genipin.
The present invention will disclose a kind of simple to operate, outstanding effect is extracted Geniposide and genipin from cape jasmine preparation method.It is raw material with the cape jasmine, extracts, concentrates, column chromatography, concentrates, obtains Geniposide after the lyophilize through extraction solvent; Geniposide enzymolysis, column chromatography, lyophilize after perhaps will concentrating make genipin, adopt this preparation method, the Geniposide and the genipin that obtain are white powder, content is (the HPLC method is measured: HighPerformance Liquid Chromatography, high performance liquid chromatography) more than 90%.
The preparation method who extracts Geniposide and genipin from cape jasmine of the present invention, described cape jasmine is drying fruit or the fresh fruit of SHANZHIZI or water cape jasmine.
The preparation method who from cape jasmine, extracts Geniposide and genipin of the present invention, described extraction solvent is water, methyl alcohol, ethanol or propyl alcohol, wherein Chun weight concentration is 30%--70%, weight concentration optimized choice 40%--60%, and optimum weight concentration is 50%.
The preparation method who from cape jasmine, extracts Geniposide and genipin of the present invention, its step is as follows:
1) the Chinese medicine cape jasmine is smashed be placed on 8-10 doubly in the extraction solvent of its weight heating and refluxing extraction 1-3 hour, temperature is controlled at 60-80 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is adsorbed with resin;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add enzyme and carry out enzymolysis;
7), by column chromatography, adsorb once more with resin with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
Among the preparation method who extracts Geniposide and genipin from cape jasmine of the present invention, column chromatography resin is selected from the macroporous adsorbent resin that model is D101 type, DA201 type, SIP series, X-5 type, AB-8 type, GDX104 type, LD605 type, LD601 type, CAD-40 type, DM-130 type, R-A type, CHA-111 type, WLD type (mixed type), H107 type, NKA-9 type, the synthetic polymeric adsorbent of small grain size that model is HP20SS or SP20SS.
Among the preparation method who from cape jasmine, extracts Geniposide and genipin of the present invention, the enzyme that enzymolysis step adopts is beta-glucosidase or cellulose complex enzyme, the consumption of enzyme is the 1/20--1/10 of raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 50--60 ℃.
A kind of Geniposide that obtains among the preparation method of Geniposide and genipin that extracts from cape jasmine of the present invention is white, column crystallization powder, weight content is (the HPLC method is measured: High Performance Liquid Chromatography, high performance liquid chromatography) more than 90%; The genipin that obtains is white, crystalloid powder, and weight content is (the HPLC method is measured: High Performance Liquid Chromatography, high performance liquid chromatography) more than 90%.
The invention provides a kind of preparation method who from cape jasmine, extracts Geniposide and genipin, improved yield, Geniposide that obtains and genipin purity height, and technology is simple, easy to operate, avoid using noxious solvents such as chloroform in the production process, avoided environmental pollution.
Description of drawings
The HPLC collection of illustrative plates of accompanying drawing 1 genipin.
The HPLC collection of illustrative plates of accompanying drawing 2 Geniposides.
The structural formula of accompanying drawing 3 genipins.
The structural formula of accompanying drawing 4 Geniposides.
Embodiment
Embodiment 1
1) the Chinese medicine cape jasmine is smashed be placed on 10 times of heating and refluxing extraction 2 hours in the pure water of its weight, temperature is controlled at 80 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is that the macroporous resin of DA201 type adsorbs with model;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add beta-glucosidase and carry out enzymolysis, the consumption of enzyme is 1/20 of a raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 55 ℃;
7),, be that the macroporous resin of DA201 type adsorbs with model by column chromatography with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
Embodiment 2
1) the Chinese medicine cape jasmine is smashed be placed on 8 times of heating and refluxing extraction 1 hour in 30% methyl alcohol of its weight, temperature is controlled at 60 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is that the synthetic polymeric adsorbent of small grain size of H107 type adsorbs with model;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add beta-glucosidase and carry out enzymolysis, the consumption of enzyme is 1/20 of a raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 60 ℃;
7),, adsorb with H107 type resin by column chromatography with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
Embodiment 3
1) the cape jasmine fresh fruit is placed 10 times to 50% ethanol heating and refluxing extraction of its weight 2 hours, temperature is controlled at 70 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is that the synthetic polymeric adsorbent of small grain size of HP20SS adsorbs with model;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add beta-glucosidase and carry out enzymolysis, the consumption of enzyme is 1/10 of a raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 50 ℃;
7),, adsorb with the HP20SS resin by column chromatography with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
Embodiment 4
1) the Chinese medicine cape jasmine is smashed be placed on 8 times of heating and refluxing extraction 2 hours in 50% ethanol of its weight, temperature is controlled at 70 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is that the macroporous resin of D101 adsorbs with model;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add beta-glucosidase and carry out enzymolysis, the consumption of enzyme is 1/10 of a raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 50 ℃;
7),, be that the synthetic polymeric adsorbent of small grain size of HP20SS adsorbs with model by column chromatography with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
1) the cape jasmine fresh fruit is placed 10 times to 60% propyl alcohol heating and refluxing extraction of its weight 2 hours, temperature is controlled at 60 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is that the synthetic polymeric adsorbent of small grain size of SP20SS adsorbs with model;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add beta-glucosidase and carry out enzymolysis, the consumption of enzyme is 1/20 of a raw material weight, and the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 50 ℃;
7),, adsorb with the SP20SS resin by column chromatography with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
Claims (7)
1, a kind of preparation method who from cape jasmine, extracts Geniposide and genipin, it is characterized in that: the processing step of preparation is:
1) the Chinese medicine cape jasmine is smashed be placed on 8-10 doubly in the extraction solvent of its weight heating and refluxing extraction 1-3 hour, temperature is controlled at 60-80 ℃, extracting solution;
2), concentrate with extracting liquid filtering;
3) filtrate after will concentrating by column chromatography, is adsorbed with resin;
4) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 15-20% again with concentration, collects elutriant;
5) elutriant is concentrated, obtain the Geniposide of paste, obtain the Geniposide of column crystallization again by lyophilize;
6) behind the Geniposide dilute with water with paste, add enzyme and carry out enzymolysis;
7), by column chromatography, adsorb once more with resin with the solution behind the enzymolysis;
8) being colourless with washed with de-ionized water resin to flowing liquid, is the ethanolic soln wash-out of 10-20% again with concentration, collects elutriant;
9) elutriant is concentrated, obtain Powdered genipin by lyophilize again.
2, a kind of preparation method who extracts Geniposide and genipin from cape jasmine as claimed in claim 1, it is characterized in that: described cape jasmine is drying fruit or the fresh fruit of SHANZHIZI or water cape jasmine.
3, a kind of preparation method who extracts Geniposide and genipin from cape jasmine as claimed in claim 1, it is characterized in that: described extraction solvent is water, methyl alcohol, ethanol or propyl alcohol.
4, a kind of preparation method who from cape jasmine, extracts Geniposide and genipin as claimed in claim 3, it is characterized in that: the weight concentration of described alcohol is 30%--70%, weight concentration optimized choice 40%--60%, optimum weight concentration is 50%.
5, a kind of preparation method who extracts Geniposide and genipin from cape jasmine as claimed in claim 1 is characterized in that: column chromatography resin is selected from the macroporous adsorbent resin that model is D101 type, DA201 type, SIP series, X-5 type, AB-8 type, GDX104 type, LD605 type, LD601 type, CAD-40 type, DM-130 type, R-A type, CHA-111 type, WLD type (mixed type), H107 type, NKA-9 type, the synthetic polymeric adsorbent of small grain size that model is HP20SS or SP20SS.
6, a kind of preparation method who from cape jasmine, extracts Geniposide and genipin as claimed in claim 1, it is characterized in that: the enzyme that enzymolysis step adopts is beta-glucosidase or cellulose complex enzyme, the consumption of enzyme is the 1/20--1/10 of raw material weight, the concentration of enzyme is 1mg/ml, and hydrolysis temperature is 50--60 ℃.
7, a kind of preparation method who from cape jasmine, extracts Geniposide and genipin as claimed in claim 1, it is characterized in that: the Geniposide that obtains is white, column crystallization powder, weight content is (the HPLC method is measured: High Performance LiquidChromatography, high performance liquid chromatography) more than 90%; The genipin that obtains is white, crystalloid powder, and weight content is (the HPLC method is measured: High Performance LiquidChromatography, high performance liquid chromatography) more than 90%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710090208 CN101029066A (en) | 2007-04-13 | 2007-04-13 | Method for extracting genipin and geniposide from gardenia jasminoides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710090208 CN101029066A (en) | 2007-04-13 | 2007-04-13 | Method for extracting genipin and geniposide from gardenia jasminoides |
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| CN101029066A true CN101029066A (en) | 2007-09-05 |
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| CN 200710090208 Pending CN101029066A (en) | 2007-04-13 | 2007-04-13 | Method for extracting genipin and geniposide from gardenia jasminoides |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146423B (en) * | 2010-02-04 | 2012-11-21 | 上海中医药大学 | Method for preparing genipin |
| CN103305555A (en) * | 2013-06-28 | 2013-09-18 | 西安纽赛生物科技有限公司 | Method for converting geniposide into genipin |
| CN105037463A (en) * | 2015-08-31 | 2015-11-11 | 桂林三宝生物科技有限公司 | Method for extracting geniposide from jasmine |
| CN105063119A (en) * | 2015-08-31 | 2015-11-18 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from gardenias |
| CN105131059A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting geniposide from jasmine |
| CN105130946A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from eucommia folium |
| CN105131061A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting geniposide from folium cortex eucommiae |
| WO2016197371A1 (en) * | 2015-06-11 | 2016-12-15 | Dsm Ip Assets B.V. | New blue color for edible coatings |
-
2007
- 2007-04-13 CN CN 200710090208 patent/CN101029066A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146423B (en) * | 2010-02-04 | 2012-11-21 | 上海中医药大学 | Method for preparing genipin |
| CN103305555A (en) * | 2013-06-28 | 2013-09-18 | 西安纽赛生物科技有限公司 | Method for converting geniposide into genipin |
| WO2016197371A1 (en) * | 2015-06-11 | 2016-12-15 | Dsm Ip Assets B.V. | New blue color for edible coatings |
| CN105037463A (en) * | 2015-08-31 | 2015-11-11 | 桂林三宝生物科技有限公司 | Method for extracting geniposide from jasmine |
| CN105063119A (en) * | 2015-08-31 | 2015-11-18 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from gardenias |
| CN105131059A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting geniposide from jasmine |
| CN105130946A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from eucommia folium |
| CN105131061A (en) * | 2015-08-31 | 2015-12-09 | 桂林茗兴生物科技有限公司 | Method for extracting geniposide from folium cortex eucommiae |
| CN105037463B (en) * | 2015-08-31 | 2018-01-30 | 桂林三宝生物科技有限公司 | A kind of method that geniposide is extracted from cape jasmine |
| CN105063119B (en) * | 2015-08-31 | 2018-11-30 | 广西红瑶药业有限公司 | The method of Geniposide is extracted from cape jasmine |
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