CN101863754A - Preparation method of crocetin, gardenia yellow pigment and saffron pigment - Google Patents
Preparation method of crocetin, gardenia yellow pigment and saffron pigment Download PDFInfo
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- CN101863754A CN101863754A CN200910097859A CN200910097859A CN101863754A CN 101863754 A CN101863754 A CN 101863754A CN 200910097859 A CN200910097859 A CN 200910097859A CN 200910097859 A CN200910097859 A CN 200910097859A CN 101863754 A CN101863754 A CN 101863754A
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Abstract
The invention provides a method for efficiently separating crocetin from fruits of rubiaceous plants and gardenia (stenophyllous gardenia, spoonleaf gardenia, gardenia hainanensis, gardenia sootepensis and gardenia) plants, saffron and saffron tissue cultures. The crocetin can be prepared by the method, and meanwhile, the gardenia yellow pigment and the saffron pigment can be prepared. The method comprises the following steps: extracting the pigment of gardenia fruits (the saffron and the saffron tissue cultures) through acid water or directly extracting raw materials through alkaline water, then carrying out water liquid acidification, then extracting ethyl acetate to obtain a crocetin crude product, and recrystallizing the crude product through different solvents to obtain a crocetin pure product. The crocetin, the gardenia yellow pigment and the saffron pigment provided by the invention can be applied in preparing cardiovascular and cerebrovascular disease medicaments, gynecological disease medicaments, tumor adjuvant therapy medicaments and foods. The method of the invention has reasonable design, the crocetin, the gardenia yellow pigment and the saffron pigment can be obtained in large scales and have high yield, and the method is quite suitable for industrialized production.
Description
Technical field
The present invention relates to the preparation method of crocetin, Gardenia Yellow and style and stigma of Saffron Crocus pigment; can be used for medicine; makeup and development of food relate in particular to the method for scale preparation crocetin, Gardenia Yellow and style and stigma of Saffron Crocus pigment from the fruit of Rubiaceae Gardenia Ellis plant and irides style and stigma of Saffron Crocus, style and stigma of Saffron Crocus tissue culture medium.
Background technology
In recent years, studies show that in a large number that crocetin has that cholagogic protects the liver, antitumor, hypermnesis, hypotensive, reducing blood-fat, antithrombotic, immunoregulatory function, disease such as also can be used for treating hypertension, coronary heart disease, hyperlipidemia, menoxenia, amenorrhoea, dysmenorrhoea, disease that postpartum lochia can't go, maculae caused by violent heat pathogen, wound, melancholy ruffian is vexed and palpitation with fear is gone mad.Crocetin mainly is present in the precious Chinese medicine style and stigma of Saffron Crocus, because the output of style and stigma of Saffron Crocus seldom, at the main dependence on import of China, can't realize the large-scale production of crocetin.China Gardenia Ellis plant distributes very wide, and cost of material is cheap, but the content of crocetin seldom.The domestic method that separation and Extraction crocetin from cape jasmine has been arranged is as a kind of method (application number 200710001116) for preparing crocetin of extracting from cape jasmine.Aforesaid method mainly utilizes crocetin solvability of extreme difference in water that crocetin is separated.Than reported method; the present invention mainly utilizes the crocetin unbound state to separate with the partition ratio difference with the solvability in the organic phase at water with bonding state (style and stigma of Saffron Crocus hydrochlorate); have that method is easy, yield is high, purity is high, can obtain advantages such as crocetin and Gardenia Yellow simultaneously, be fit to very much industrialization, large-scale production.
Simultaneously, this method can apply to the preparation of crocetin and style and stigma of Saffron Crocus pigment in style and stigma of Saffron Crocus medicinal material, the style and stigma of Saffron Crocus tissue culture.
Summary of the invention
The object of the present invention is to provide a kind of crude substance crocetin and high-grade edible pigment, protective foods, makeup Gardenia Yellow and style and stigma of Saffron Crocus pigment with new drug, protective foods, makeup DEVELOPMENT PROSPECT.
Another object of the present invention is to provide the preparation method of crocetin, Gardenia Yellow and style and stigma of Saffron Crocus pigment.
The present invention also provides the preparation that contains crocetin.
The purity of crocetin provided by the invention is greater than 99% (liquid phase method).
The preparation method of crocetin of the present invention, Gardenia Yellow and style and stigma of Saffron Crocus pigment, comprise the following steps: after the Gardenia Ellis fruit is by the acid extraction Gardenia Yellow or the fruit raw material is directly used potass extraction, obtain the crocetin crude product with ethyl acetate extraction after the acidifying of water liquid, crude product obtains the pure product of crocetin with the different solvents recrystallization; Behind style and stigma of Saffron Crocus medicinal material, the style and stigma of Saffron Crocus tissue culture medium acid extraction style and stigma of Saffron Crocus pigment or directly use potass extraction, obtain the crocetin crude product with ethyl acetate extraction after the acidifying of water liquid, crude product obtains the pure product of crocetin with the different solvents recrystallization.
Crocetin of the present invention can be used as activeconstituents, adds the auxiliary material of accepting on the pharmaceutics, makes preparation according to the preparation method of the preparation of putting down in writing on the pharmaceutics.
Crocetin of the present invention can also be as one of activeconstituents, adds the auxiliary material of accepting on the pharmaceutics, makes preparation according to the preparation method of the preparation of putting down in writing on the pharmaceutics.
Described preparation comprises injection liquid, drip liquid, powder injection, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, sucks agent, granule, pill, paste, sublimed preparation, sprays, pill, disintegrating agent, orally disintegrating tablet, micropill etc.
Crocetin of the present invention, style and stigma of Saffron Crocus pigment can also add auxiliary material as one of main active ingredient or activeconstituents, and the preparation method makes makeup according to makeup.
Crocetin of the present invention, style and stigma of Saffron Crocus pigment can also add auxiliary material as one of main active ingredient or activeconstituents, and the preparation method makes protective foods according to protective foods.
Embodiment
Further describe flesh and blood of the present invention and beneficial effect below in conjunction with embodiment, this embodiment only is used to the present invention is described but not limitation of the present invention.
The preparation of embodiment one crocetin
The Gardenia Ellis fruit is pulverized the back adds buck (transferring to pH ≈ 10) with NaOH etc., heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid II with extractions such as ethyl acetate, ether then.Extraction liquid II concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99% (Fig. 1).
The preparation of embodiment two crocetins and Gardenia Yellow
The Gardenia Ellis fruit is pulverized the back to add sour water (transferring to pH ≈ 3 with HCl etc.) heating and extracts and obtain Gardenia Yellow.The dregs of a decoction add buck (transferring to pH ≈ 10 with NaOH etc.), heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid with extractions such as ethyl acetate, ether then.Extraction liquid concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99% (Fig. 1).
The preparation of embodiment three style and stigma of Saffron Crocus acid
The Gardenia Ellis fruit is pulverized the back to add alkaline alcohol (70-80% ethanol transfers to pH ≈ 10 with NaOH etc.) heating and extracts and obtain alcohol extract.Alcohol extract is recycled to and contains the alcohol amount less than 10%, with the low polar material of flush awaies such as ethyl acetate, ether.Water liquid transfers to pH ≈ 3 with HCl etc., obtains extraction liquid with extractions such as ethyl acetate, ether then.Extraction liquid concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99% (Fig. 1).
The preparation of embodiment four crocetins and Gardenia Yellow
The Gardenia Ellis fruit is pulverized the back to add acid alcohol (70-80% ethanol transfers to pH ≈ 3 with HCl etc.) heating and extracts and obtain alcohol extract.Alcohol extract is recycled to and contains the alcohol amount less than 10%, obtains extraction liquid I with extractions such as ethyl acetate, ether then.Water liquid concentrates and obtains Gardenia Yellow.Extraction liquid I obtains extraction liquid II with buck (transferring to pH ≈ 10 with NaOH etc.) extraction.Extraction liquid II concentrates and obtains the crocetin crude product, and recrystallizations such as the methyl alcohol of crocetin crude product usefulness different concns, ethanol, tetrahydrofuran (THF), buck promptly get the pure product of crocetin, and purity is greater than 99% (Fig. 1).
The preparation of embodiment five crocetins
To add buck (transferring to pH ≈ 10) after the style and stigma of Saffron Crocus pulverizing medicinal materials with NaOH etc., heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid II with extractions such as ethyl acetate, ether then.Extraction liquid II concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99%.
The preparation of embodiment six crocetins and style and stigma of Saffron Crocus pigment
Extract and obtain the style and stigma of Saffron Crocus pigment adding sour water (transferring to pH ≈ 3) heating after the style and stigma of Saffron Crocus pulverizing medicinal materials with HCl etc.The dregs of a decoction add buck (transferring to pH ≈ 10 with NaOH etc.), heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid with extractions such as ethyl acetate, ether then.Extraction liquid concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99%.
The preparation of embodiment seven crocetins
The style and stigma of Saffron Crocus tissue culture is added buck (transferring to pH ≈ 10 with NaOH etc.), heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid II with extractions such as ethyl acetate, ether then.Extraction liquid II concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99%.
The preparation of embodiment eight crocetins and style and stigma of Saffron Crocus pigment
The style and stigma of Saffron Crocus tissue culture is added sour water (transferring to pH ≈ 3 with HCl etc.) heating to be extracted and obtains the style and stigma of Saffron Crocus pigment.The dregs of a decoction add buck (transferring to pH ≈ 10 with NaOH etc.), heating extract extracting solution I, extracting solution I transfers to pH ≈ 3 with HCl etc., obtains extraction liquid with extractions such as ethyl acetate, ether then.Extraction liquid concentrate to produce precipitation, filters to obtain the crocetin crude product, and the crocetin crude product promptly gets the pure product of crocetin with recrystallizations such as the methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), bucks, and purity is greater than 99%.
The analysis of embodiment nine crocetins
The assay of crocetin (high performance liquid chromatography)
Chromatographic conditionChromatographic condition: chromatographic column Agilent Zorbax SB-C
18Post (4.6mm * 150mm, 5 μ m); Adopt gradient elution, mobile phase A is 0.2% glacial acetic acid aqueous solution mutually, and Mobile phase B is mutually for containing the acetonitrile solution of 0.2% Glacial acetic acid; Flow velocity 0.5mLmin
-1Detect wavelength: 440nm; 30 ℃ of column temperatures; Sample size 5 μ L.
The preparation of need testing solutionTake by weighing this product, in volumetric flask, be diluted to scale, shake up, promptly with dissolve with methanol solution.
Measuring methodThe accurate need testing solution of drawing injects liquid chromatograph, measures, promptly.
Analytical resultsThe analysis of spectra of crocetin is seen Fig. 1.Peak among Fig. 1 is a crocetin, and its content is greater than 99%.
The preparation of embodiment ten dropping pill formulations
Get crocetin 0.5g and 10.5g polyoxyethylene glycol-6000 mixes, heating and melting moves in the dripping pill drip irrigation after changing material, and in ℃ whiteruss of medicine liquid droplet to 6～8, oil removing makes 300 of dripping pills.
The preparation of embodiment 11 lyophilized injectable powders
Get crocetin 0.5g, glucose 4.5g, Sulfothiorine 0.9g and distilled water 1000ml, after said components mixes, lyophilize, 400 of packing, promptly.
Claims (4)
1. the method for a scale preparation crocetin, Gardenia Yellow and style and stigma of Saffron Crocus pigment;
2. the source of crocetin and Gardenia Yellow is fruit, style and stigma of Saffron Crocus Crocus sativus Linn. and the style and stigma of Saffron Crocus tissue culture of the plant of Rubiaceae Rubiaceae Gardenia Ellis Gardenia, comprising: narrow leaf cape jasmine Gardenia stenophylla Merr., spoon leaf cape jasmine Gardenia angkorensis Pitard, Hainan cape jasmine Gardenia hainanensis Merr., all Gardenia Ellis fruits such as big Yellow Fructus Gardeniae Gardenia sootepensis hutchins., cape jasmine Gardenia jasminoides Ellis.
3. the preparation method of crocetin, Gardenia Yellow and style and stigma of Saffron Crocus pigment may further comprise the steps: the Gardenia Ellis fruit by the acid extraction Gardenia Yellow after or the fruit raw material directly use potass extraction, obtain the crocetin crude product with ethyl acetate equal solvent extraction after the acidifying of water liquid; Behind style and stigma of Saffron Crocus medicinal material, the style and stigma of Saffron Crocus tissue culture acid extraction style and stigma of Saffron Crocus pigment or directly use potass extraction, obtain the crocetin crude product with the extraction of ethyl acetate equal solvent after the acidifying of water liquid.
4. the crocetin crude product obtains the pure product of crocetin with different solvents (methyl alcohol of different concns, ethanol, tetrahydrofuran (THF), buck etc.) recrystallization.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102293740A (en) * | 2011-08-04 | 2011-12-28 | 广东省中药研究所 | crocetin injection and preparation method thereof |
| CN102432455A (en) * | 2011-12-14 | 2012-05-02 | 广西大学 | Method for preparing crocetin and crocin |
| CN102936424A (en) * | 2012-11-09 | 2013-02-20 | 苏州衷中医药科技有限公司 | Method for preparing gardenia yellow pigment with high color value |
| 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 |
| CN104610207A (en) * | 2014-07-15 | 2015-05-13 | 云南西力生物技术股份有限公司 | Gardenia sootepensis gardenin A, preparation method and medicinal application thereof |
| CN105503968A (en) * | 2015-12-02 | 2016-04-20 | 武汉绿孚生物工程有限责任公司 | Method for separation and purification of crocin and crocetion from gardenia yellow pigment |
| US20170248561A1 (en) * | 2016-02-29 | 2017-08-31 | Henan Zhongda Biological Engineering Co., Ltd. | Method to determine the crocetin and its derivative amounts and the derivative composition from gardenia yellow |
| CN111122466A (en) * | 2019-05-14 | 2020-05-08 | 南阳泰瑞生物科技股份有限公司 | Method for measuring content of gardenia yellow based on color value and high performance liquid chromatography |
| WO2021114089A1 (en) * | 2019-12-10 | 2021-06-17 | Hangzhou Menglanruisi Biotechnology Co., Ltd. | Methods of using crocetin in treating solid tumors |
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| CN101012248A (en) * | 2007-02-02 | 2007-08-08 | 华东理工大学 | Method of separating and concentrating iridoid glycosides and crocin in cape jasmine fruit |
| CN101165104A (en) * | 2006-10-18 | 2008-04-23 | 大闽食品（漳州）有限公司 | Technique for preparing gardenia yellow pigment |
| CN101225040A (en) * | 2007-01-18 | 2008-07-23 | 中国科学院过程工程研究所 | Method for extracting crocetin from gardenia |
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Patent Citations (3)
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| CN101165104A (en) * | 2006-10-18 | 2008-04-23 | 大闽食品（漳州）有限公司 | Technique for preparing gardenia yellow pigment |
| CN101225040A (en) * | 2007-01-18 | 2008-07-23 | 中国科学院过程工程研究所 | Method for extracting crocetin from gardenia |
| CN101012248A (en) * | 2007-02-02 | 2007-08-08 | 华东理工大学 | Method of separating and concentrating iridoid glycosides and crocin in cape jasmine fruit |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102293740A (en) * | 2011-08-04 | 2011-12-28 | 广东省中药研究所 | crocetin injection and preparation method thereof |
| CN102432455A (en) * | 2011-12-14 | 2012-05-02 | 广西大学 | Method for preparing crocetin and crocin |
| CN102936424A (en) * | 2012-11-09 | 2013-02-20 | 苏州衷中医药科技有限公司 | Method for preparing gardenia yellow pigment with high color value |
| CN102936424B (en) * | 2012-11-09 | 2014-10-08 | 苏州衷中医药科技有限公司 | Method for preparing gardenia yellow pigment with high color value |
| CN104610207A (en) * | 2014-07-15 | 2015-05-13 | 云南西力生物技术股份有限公司 | Gardenia sootepensis gardenin A, preparation method and medicinal application thereof |
| 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 |
| CN105503968A (en) * | 2015-12-02 | 2016-04-20 | 武汉绿孚生物工程有限责任公司 | Method for separation and purification of crocin and crocetion from gardenia yellow pigment |
| CN105503968B (en) * | 2015-12-02 | 2017-10-31 | 武汉绿孚生物工程有限责任公司 | A kind of method of separating-purifying crocin and crocetin from Gardenia Yellow |
| US20170248561A1 (en) * | 2016-02-29 | 2017-08-31 | Henan Zhongda Biological Engineering Co., Ltd. | Method to determine the crocetin and its derivative amounts and the derivative composition from gardenia yellow |
| US9921198B2 (en) * | 2016-02-29 | 2018-03-20 | Henan Zhongda Biological Engineering Co. Ltd. | Method to determine the crocetin and its derivative amounts and the derivative composition from gardenia yellow |
| CN111122466A (en) * | 2019-05-14 | 2020-05-08 | 南阳泰瑞生物科技股份有限公司 | Method for measuring content of gardenia yellow based on color value and high performance liquid chromatography |
| WO2021114089A1 (en) * | 2019-12-10 | 2021-06-17 | Hangzhou Menglanruisi Biotechnology Co., Ltd. | Methods of using crocetin in treating solid tumors |
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