CN102432455B - Method for preparing crocetin and crocin - Google Patents

Method for preparing crocetin and crocin Download PDF

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Publication number
CN102432455B
CN102432455B CN201110417356.1A CN201110417356A CN102432455B CN 102432455 B CN102432455 B CN 102432455B CN 201110417356 A CN201110417356 A CN 201110417356A CN 102432455 B CN102432455 B CN 102432455B
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Prior art keywords
medicinal extract
ethyl acetate
crocetin
extract
crocin
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CN201110417356.1A
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CN102432455A (en
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韦万兴
刘盛
周敏
凌秀荣
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Guangxi University
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Guangxi University
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Abstract

The invention discloses a method for preparing crocetin and crocin, which comprises the following steps: preparing a gardenia fruit extracting solution with ethanol under the conditions of ultrasonic waves, and concentrating the extracting solution to obtain an extract; and dissolving the extract in a polyethylene glycol aqueous solution, and selectively extracting with solvent to obtain crocetin and crocin. The invention does not need the chromatographic column separation process, has the advantages of simple operational method, and high product yield and purity, and is suitable for industrial production.

Description

A kind of method of preparing trans-crocetin and Crocin
Technical field
The invention belongs to a kind of technical field of extracting effective ingredient from plant.A kind of method of preparing crocetin and crocin specifically.
Technical background
Cape jasmine is Rubiaceae Gardenia Ellis evergreen shrubs, the fruit of cape jasmine drying and ripening, shape is oblong or ellipse, be scarlet or yellowish red color, for one of first batch of integration of drinking and medicinal herbs Chinese medicinal materials of ratifying of ministry of Health of China, there is the flu of curing mainly, insomnia, icterohepatitis and the effect such as promoting blood circulation and removing blood stasis, mainly originate in the knob on the south the Changjiang river.
From cape jasmine fruit, extract separated water-soluble carotenoid class pigment, its main component is that Crocin (has another name called crocin, crocin, molecular formula C 44h 64o 24) and trans-crocetin (have another name called crocetin, crocetin, molecular formula C 20h 24o 4).
Main component is that the Gardenia Yellow of Crocin and trans-crocetin is widely used in food colorant, is a kind of natural plant pigment that integrates painted, nutrition, multifunctional health, is widely used in food, medicine and chemical field etc.At present, the research of Crocin and trans-crocetin is mainly laid particular emphasis on to its pharmacological action aspect, mostly Crocin is the research of extracting about the style and stigma of Saffron Crocus from the rare high price of thing, and the research of extraction and separation process aspect is less from the inexpensive cape jasmine fruit of aboundresources.Therefore, research is extracted separated Crocin and trans-crocetin from cape jasmine fruit, is the gordian technique to cape jasmine deep development, is also one and reduces costs, and increases the effective way of economic benefit.
The method major part of preparing Crocin and trans-crocetin of bibliographical information is with macroreticular resin absorbing method at present, silica gel chromatography, and supercritical extractions etc., obtain pure Crocin and trans-crocetin, must use chromatography.These method treatment capacities are little, and production efficiency is low.
Summary of the invention
The object of the invention is to overcome the treatment capacity existing in existing preparation method little, be unfavorable for the shortcoming of suitability for industrialized production, a kind of environmental friendliness, the easy and simple to handle method of preparing crocetin and crocin are provided.
The technical scheme that the present invention solves the problems of the technologies described above is as follows:
A kind of method of preparing trans-crocetin and sugar ester-Crocin thereof, the ripe dry fruit of the cape jasmine of take is raw material, with ethanol, under Ultrasonic Conditions, prepare cape jasmine fruit extracting solution, the concentrated medicinal extract that obtains of extracting solution, medicinal extract is dissolved in Aqueous Solutions of Polyethylene Glycol, then with solvent, carries out selective extraction and obtains crocetin and sugar ester thereof; Comprise the following steps:
1. the preparation of cape jasmine fruit crude extract
To be dried cape jasmine and really pulverize, with 95% alcohol immersion of 5-20 times of cape jasmine dry weight, ultrasonic extraction 3-4 time, each 1.0-1.5 hour, filters, and filtrate is merged to concentrating under reduced pressure and become medicinal extract;
2. Gardenia Yellow obtains enrichment
The medicinal extract that step 1 is made is water-soluble, obtains the medicinal extract aqueous solution, uses the isopyknic n-butanol extraction of the medicinal extract aqueous solution 3 times, n-butanol layer in combining extraction liquid, and concentrating under reduced pressure obtains Gardenia Yellow enrichment medicinal extract;
3. the separation of trans-crocetin
Getting the Gardenia Yellow enrichment medicinal extract that a certain amount of step 2 makes is dissolved in after medicinal extract weight 20-30 water doubly, add polyoxyethylene glycol, after dissolving, obtain medicinal extract solution, with the isopyknic petroleum ether extraction of medicinal extract solution, remove the impurity of little polarity, then extract 3-4 time by the isopyknic ethyl acetate of medicinal extract solution, obtain acetic acid ethyl acetate extract, ethyl acetate layer in combined ethyl acetate extraction liquid, by its concentrating under reduced pressure, is dried and obtains purer trans-crocetin;
4. step 3 is obtained to acetic acid ethyl acetate extract, water layer in combining extraction liquid, by ethyl acetate: the mixing solutions precipitation of ethanol=3: 1 (V/V), be precipitated after filtration, by ethyl acetate: ethanol=3: the precipitation after 1 mixing solutions washing and filtering, precipitation after washing is water-soluble, be precipitated the aqueous solution, with precipitating the isopyknic ethyl acetate of the aqueous solution: propyl carbinol=3: 2 mixed extractant solvent 3 times, organic layer in combining extraction liquid, by its concentrating under reduced pressure, be dried and obtain purer Crocin.
In above-mentioned steps 1, will be dried cape jasmine and really pulverize, with 95% alcohol immersion of 5-20 times of cape jasmine dry weight, ultrasonic extraction 3-4 time, each 1.0-1.5 hour, filters, and filtrate is merged to concentrating under reduced pressure and become medicinal extract.
The present invention has the following advantages:
1. the present invention be take ultrasonic wave as auxiliary, with ethanol, cape jasmine fruit meal is extracted, this extracting method has fast, advantage thoroughly, reduced the step that need to remove carbohydrate by water extraction, the productive rate that can shorten production cycle and raising Gardenia Yellow in industrial production, ethanol is recyclable to be recycled.
2. the present invention has adopted polyoxyethylene glycol, has increased the selectivity of extraction system, has improved efficiency and the purity of extraction, and polyoxyethylene glycol is recyclable.
3. the present invention has used the method separation of pure extraction to obtain Crocin and trans-crocetin, does not use macroporous resin adsorption and silica gel chromatography, and treatment capacity is large, easy and simple to handle, is easy to amplify and suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention is described in detail.
Embodiment 1
Take cape jasmine fruit meal 500g, ultrasonic extraction four times, add 2500ml 95% extraction using alcohol 1.0 hours at every turn, merge No. four extracting solution concentrating under reduced pressure and become medicinal extract, medicinal extract is dissolved in 200ml distilled water, with 200ml propyl carbinol continuous extraction 3 times, merge n-butanol layer, concentrating under reduced pressure becomes medicinal extract, gets 2.2g medicinal extract and is dissolved in 44ml water, add 0.88g Polyethylene glycol-2000, with 44ml petroleum ether extraction, remove the impurity of little polarity, then by 44ml ethyl acetate, extract 3 times combined ethyl acetate layer, concentrating under reduced pressure is dry obtains 185mg trans-crocetin, and productive rate reaches 8.4%.The mixing solutions precipitation of water layer ethyl acetate: ethanol=3: 1 (V/V), filters, and precipitation is dissolved in 100ml water, use 100ml ethyl acetate: propyl carbinol=3: 2 mixed extractant solvent 3 times, merges organic layer, concentrating under reduced pressure, be dried and obtain 195mg Crocin, productive rate reaches 8.7%.
Embodiment 2
Take cape jasmine fruit meal 500g, ultrasonic extraction four times, add 5000ml 95% extraction using alcohol 1.5 hours at every turn, merge No. four extracting solution concentrating under reduced pressure and become medicinal extract, medicinal extract is dissolved in 200ml distilled water, with 200ml propyl carbinol continuous extraction 3 times, merge n-butanol layer, concentrating under reduced pressure becomes medicinal extract, gets 2.2g medicinal extract and is dissolved in 55ml water, add 1.10g Polyethylene glycol-2000, with 55ml petroleum ether extraction, remove the impurity of little polarity, then by 55ml ethyl acetate, extract 3 times combined ethyl acetate layer, concentrating under reduced pressure is dry obtains 180mg trans-crocetin, and productive rate reaches 8.2%.Water layer 3: 1 (V/V) precipitations of ethyl acetate-ethanol, filter, and precipitation is dissolved in 100ml water, uses 100ml ethyl acetate: propyl carbinol=3: 2 mixed extractant solvents 3 times, merge organic layer, and concentrating under reduced pressure, is dried and obtains 185mg Crocin, and productive rate reaches 8.4%.
Embodiment 3
Take cape jasmine fruit meal 500g, ultrasonic extraction three times, add 7500ml 95% extraction using alcohol 1.0 hours at every turn, merge No. three extracting solution concentrating under reduced pressure and become medicinal extract, medicinal extract is dissolved in 200ml distilled water, with 200ml propyl carbinol continuous extraction 3 times, merge n-butanol layer, concentrating under reduced pressure becomes medicinal extract, gets 2.2g medicinal extract and is dissolved in 55ml water, add 1.10g Polyethylene glycol-2000, with 55ml petroleum ether extraction, remove the impurity of little polarity, then by 55ml ethyl acetate, extract 4 times combined ethyl acetate layer, concentrating under reduced pressure is dry obtains 175mg trans-crocetin, and productive rate reaches 8.0%.Water layer 3: 1 (V/V) precipitations of ethyl acetate-ethanol, filter, and precipitation is dissolved in 100ml water, uses 100ml ethyl acetate: propyl carbinol=3: 2 mixed extractant solvents 3 times, merge organic layer, and concentrating under reduced pressure, is dried and obtains 190mg Crocin, and productive rate reaches 8.6%.
Embodiment 4
Take cape jasmine fruit meal 500g, ultrasonic extraction three times, add 10000ml 95% extraction using alcohol 1 hour at every turn, merge No. three extracting solution concentrating under reduced pressure and become medicinal extract, medicinal extract is dissolved in 200ml distilled water, with 200ml propyl carbinol continuous extraction 3 times, merge n-butanol layer, concentrating under reduced pressure becomes medicinal extract, gets 2.2g medicinal extract and is dissolved in 66ml water, add 1.32g Polyethylene glycol-2000, with 66ml petroleum ether extraction, remove the impurity of little polarity, then by 66ml ethyl acetate, extract 4 times combined ethyl acetate layer, concentrating under reduced pressure is dry obtains 170mg trans-crocetin, and productive rate reaches 7.7%.Water layer 3: 1 (V/V) precipitations of ethyl acetate-ethanol, filter, and precipitation is dissolved in 100ml water, uses 100ml ethyl acetate: propyl carbinol=3: 2 mixed extractant solvents 3 times, merge organic layer, and concentrating under reduced pressure, is dried and obtains 180mg Crocin, and productive rate reaches 8.2%.

Claims (2)

1. a method of preparing trans-crocetin and Crocin; the ripe dry fruit of the cape jasmine of take is raw material, prepares cape jasmine fruit extracting solution with ethanol under Ultrasonic Conditions, the concentrated medicinal extract that obtains of extracting solution; medicinal extract is dissolved in Aqueous Solutions of Polyethylene Glycol, then with solvent, carries out selective extraction and obtains crocetin and Crocin; Comprise the following steps:
(1) preparation of cape jasmine fruit crude extract
To be dried cape jasmine and really pulverize, with 95% alcohol immersion of 5-20 times of cape jasmine dry weight, ultrasonic extraction 3-4 time, each 1.0-1.5 hour, filters, and filtrate is merged to concentrating under reduced pressure and become medicinal extract;
(2) enrichment of Gardenia Yellow
The medicinal extract that step (1) is made is water-soluble, obtains the medicinal extract aqueous solution, uses the isopyknic n-butanol extraction of the medicinal extract aqueous solution 3 times, n-butanol layer in combining extraction liquid, and concentrating under reduced pressure obtains Gardenia Yellow enrichment medicinal extract;
(3) separation of trans-crocetin
Getting the Gardenia Yellow enrichment medicinal extract that a certain amount of step (2) makes is dissolved in after medicinal extract weight 20-30 water doubly, add polyoxyethylene glycol, after dissolving, obtain medicinal extract solution, with the isopyknic petroleum ether extraction of medicinal extract solution, remove the impurity of little polarity, then extract 3-4 time by the isopyknic ethyl acetate of medicinal extract solution, obtain acetic acid ethyl acetate extract, ethyl acetate layer in combined ethyl acetate extraction liquid, by its concentrating under reduced pressure, is dried and obtains purer trans-crocetin;
(4) step (3) is obtained to acetic acid ethyl acetate extract, water layer in combining extraction liquid, use volume ratio ethyl acetate: ethanol=3: 1 mixing solutions precipitation, be precipitated after filtration, use volume ratio ethyl acetate: ethanol=3: the precipitation after 1 mixing solutions washing and filtering, precipitation after washing is water-soluble, be precipitated the aqueous solution, with precipitating the isopyknic mixed extractant solvent of the aqueous solution 3 times, described mixed solvent is volume ratio ethyl acetate: propyl carbinol=3: 2, organic layer in combining extraction liquid, by its concentrating under reduced pressure, is dried and obtains purer Crocin.
2. a kind of method of preparing high purity trans-crocetin and Crocin according to claim 1, is characterized in that in described step (1), with 95% alcohol immersion of 10 times of cape jasmine dry weights, and ultrasonic extraction 3 times, each 1.0 hours.
CN201110417356.1A 2011-12-14 2011-12-14 Method for preparing crocetin and crocin Expired - Fee Related CN102432455B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102746704A (en) * 2012-06-20 2012-10-24 浙江大学 Ultrasonic extracting process for gardenia yellow pigment and optimized method of response surface methodology used therein
CN103919879B (en) * 2014-04-17 2015-11-18 陕西师范大学 The preparation method of a kind of almond peel procyanidin and chlorogenic acid health product
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
CN105675525B (en) * 2016-02-29 2017-01-11 河南中大恒源生物科技股份有限公司 Method for determining total quantity and constitution of crocetin derivative in gardenia yellow product
CN105935363B (en) * 2016-04-29 2017-03-08 暨南大学 Composition, safron class active site and application thereof
CN109646535A (en) * 2018-10-12 2019-04-19 金华寿仙谷药业有限公司 Safflower petal refines alcohol extract and its preparation method and application
CN109232230A (en) * 2018-10-31 2019-01-18 湖南中茂生物科技有限公司 A method of extracting crocin from fresh gardenia

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JPS5216728B2 (en) * 1974-12-14 1977-05-11
JP2004269663A (en) * 2003-03-07 2004-09-30 Riken Vitamin Co Ltd Method for purifying crocetin
CN100523093C (en) * 2006-05-25 2009-08-05 北京化工大学 Method for extracting high color-value gardenin
CN101225040B (en) * 2007-01-18 2011-05-04 中国科学院过程工程研究所 Method for extracting crocetin from gardenia
CN101863754A (en) * 2009-04-17 2010-10-20 杭州法和医药科技有限公司 Preparation method of crocetin, gardenia yellow pigment and saffron pigment

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