CN101143842A - Method for extracting sulforaphen - Google Patents
Method for extracting sulforaphen Download PDFInfo
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- CN101143842A CN101143842A CNA2007101561408A CN200710156140A CN101143842A CN 101143842 A CN101143842 A CN 101143842A CN A2007101561408 A CNA2007101561408 A CN A2007101561408A CN 200710156140 A CN200710156140 A CN 200710156140A CN 101143842 A CN101143842 A CN 101143842A
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Abstract
The invention discloses a method of extracting sulforaphen. The smashed seeds of west orchids are added with two to three times as much water, the pH value is regulated to 3.8 to 4.2, ascorbic acid is added, and hydrolysis lasts seven to nine hours under the temperature of 20 to 30 DEG C; after being refrigerated and dried, the raw solution is added with fifteen to twenty five times as much propanone, supersonic extraction lasts forty to eighty minutes, and pumping filtration or double-gauze filtration follows; under the temperature of 30 to 50 DEG C, filtrate undergoes vacuum concentration in order to obtain crude sulforaphen; the crude sulforaphen is chromatographed by a silica gel column and gradiently eluted by n-hexane acetone solution, the thin-layer chromatography or HPLC tests and determines fractions containing the sulforaphen, and the crude sulforaphen undergoes vacuum concentration under the temperature of 30 to 50 DEG C; after being resolved in a small amount of acetone, the crude sulforaphen is chromatographed by a Sephadex LH-20 column, the acetone is used as eluent, the thin-layer chromatography or HPLC tests, determines and collects liquor containing the sulforaphen, and by vacuum concentration under the temperature of 30 to 50 DEG C, a sulforaphen product with eighty percent purity is produced. The method of the invention can also be used to extract the sulforaphen from the seeds of radishes, cabbages and mustards.
Description
Technical field
The invention belongs to technological field of biochemistry, relate to extraction of effective components in the natural product, be specially from plant seed the method for extracting sulforaphen, especially the method for extraction sulforaphen from brassicaceous vegetable as in the seed of Caulis et Folium Brassicae capitatae, radish, wild cabbage and leaf mustard.
Background technology
According to World Health Organization's statistics, the annual number because of cancer mortality in the whole world is about 7,000,000 at present, and China also has 1,000,000 people therefore to lose one's life.20 years from now on new patients of global cancer will be increased to 5,000 ten thousand by present annual 1000 ten thousand, because of the cancer mortality number will increase to 1,000 ten thousand by annual 6000000.This is one group of very heavy data, but up to now, we still do not find the way of capturing cancer.Therefore, research and control tumour are the great problems of current life science.Epidemiology and pharmaceutical research show, the place that cancer morbidity is low, vegetables in people's diet, fruit proportion are bigger, trace it to its cause, be the active components of plants that has one or more preventions or the cancer development that slows down in vegetables, the fruit, as the Lyeopene in the tomato, soybean isoflavones, tanning acid in the berry and the sulforaphen in the brassicaceous vegetable in the soya products, indoles material.They all are proved has good anti-cancer and kill cancer action.In numerous vegetables that contain anticancer active constituent, Cruciferae (cabbage, asparagus broccoli, the blue and white cabbage of kohlrabi, cabbage mustard, lettuce, white turnip and cabbage etc.) is rich in glucosinolate (sulphur glucoside), and it can be degraded into isothiocyanate class cancer-resisting substance under the myrosin effect that vegetables itself have.Sulforaphen is to belong to a kind of in the isothiocyanate, and it also is the strongest anticancer component of finding in the vegetables up to now.Broccoli seed is rich in the glucosinolate of sulforaphen precursor.
Though glucosinolate has certain research to the conversion of isothiocyanate, lack enzymatic hydrolysis condition, technology control condition, extract method of purification research.The method that lacks extensive extraction sulforaphen at present more lacks the technology that sulforaphen is separated from other isothiocyanate.
In recent years, Chinese scholar had also been carried out some researchs about isothiocyanate and precursor sulphur glucoside thereof, and studying more at present is isothiocyanate in horseradish and the mustard, and it mainly is as seasonings.Different isothiocyanates, its biological activity exists very big difference.Extraction, biological activity for sulforaphen lack research.The research to sulforaphen abroad rests on laboratory stage at present, lacks large-scale technology of preparing.How glucosinolate regulates and control to lack further investigation to the transformation mechanism complexity of isothiocyanate to conversion condition.Also lack and extract and purification techniques.Sulforaphen has good anticancer effect, if can optimize its conversion and extraction process, and extensive the extraction.Make its intermediate that becomes pharmacy or food function composition, can promote the related products exploitation, will have vast market prospect.
Summary of the invention
The purpose of this invention is to provide a kind of method of from the seed of brassicaceous vegetable such as Caulis et Folium Brassicae capitatae, radish, wild cabbage and leaf mustard, extracting sulforaphen.
By to technology such as amount of water, raw materials pretreatment, adjusting hydrolysis pH value, hydrolysis temperature, enzymolysis time, ultrasonic time, the selection of silica gel column chromatography eluent, the selections of Sephadex LH-20 chromatography eluent, optimize the formation and the extraction process of sulforaphen, realize scale operation.
Extraction process of the present invention is as follows:
(1) be raw material with broccoli seed, add 2～3 times of water gagings by weight after it is pulverized, regulate pH3.8～4.2,
Hydrolysis is 7～9 hours under 20～30 ℃ of conditions;
(2) with the broccoli seed stoste lyophilize powdering after the hydrolysis;
(3) add 15～25 times of amount acetone solvents by weight in the powdery hydrolyzate, ultrasonic lixiviate 40～80 minutes is taken out
Filter or double gauze filter;
(4) filtrate vacuum concentration under 30～50 ℃ of conditions is obtained the sulforaphen crude product;
(5) with the sulforaphen crude product through silica gel column chromatography, adopt normal hexane acetone soln gradient elution, thin-layer chromatography or
HPLC detects the cut of determining to contain sulforaphen, vacuum concentration under 30～50 ℃ of conditions;
(6) with the sulforaphen of above-mentioned vacuum concentration with the small amount of acetone dissolving after, with Sephadcx LH-20 column chromatography,
With acetone is eluent, and thin-layer chromatography or HPLC detect and determine and collect to contain sulforaphen liquid, again through 30～
50 ℃ of vacuum concentration obtain the sulforaphen product.
The concrete prescription of the described normal hexane acetone soln of step (5) gradient elution is: by volume, normal hexane: acetone was respectively 5: 5, and 4: 6,3: 7,2: 8.
In the hydrating solution of step (1), add 0.02 gram xitix by the per kilogram raw material.
The condition of the described ultrasonic lixiviate of step (3) is: frequency 40khz, power 200W opens 70% grade.
Above-mentioned steps is summarized as follows:
After pulverizing, broccoli seed adds water 1: 2-1: 3 times of amounts, add hydrochloric acid and transfer pH3.8-pH4.2, hydrolysis 7h 9h under 20 ℃ of-30 ℃ of room temperatures adds the 15-25 times of ultrasonic lixiviate 40min-80min of acetone solvent after the lyophilize, suction filtration or double gauze filter, and 30 ℃ of 50 ℃ of vacuum concentrated filtrates obtain thick product; (gradient is a normal hexane to silica gel column chromatography: acetone (v/v)=5: 5,4: 6,3: 7,2: 8), collection contains sulforaphen liquid (thin-layer chromatography or HPLC detect and determine), 30 ℃ of-50 ℃ of vacuum concentrated filtrates, small amount of acetone dissolving back Sephadex LH-20 column chromatography (acetone is eluent), collection contains sulforaphen liquid (thin-layer chromatography or HPLC detect and determine), and 30 ℃ of-50 ℃ of vacuum concentrated filtrates obtain the sulforaphen product.
Amount of water: amount of water very little, Caulis et Folium Brassicae capitatae does not also soak fully, the hydrolysis rate of sulphur glucoside is just slow, needs the more times hydrolysis.When broccoli seed is soaked fully, it is mild that the trend that is increased just becomes.Consider that too high amount of water can be unfavorable for lyophilize, therefore select broccoli seed: water=1: 2～3.
Xitix: when experiment, add the hydrolysis that a small amount of xitix can improve the sulphur glycosides significantly.Xitix can improve the enzyme of myrosin lives, and its activation mechanism is that xitix can make the conformation of myrosin that slight the variation taken place.Xitix is when 0.02mg/g, and the content of sulforaphen is improved.
PH: at pH is that the hydrolysis of 4 o'clock sulphur glucosides is the most complete, the enzymic activity maximum, and the content of sulforaphen also will uprise.
Supersound process: ultrasonic 1 hour, can significantly improve sulforaphen and from tissue, be dissolved into solvent.Ultransonic condition is: frequency 40khz, power 200W opens 70% grade.
Silica gel column chromatography: parting material: silica gel (200～300 order), glass column (50 * 3cm).As the method for initial gross separation sulforaphen, select for use eluent normal hexane and acetone proportioning to carry out gradient elution.Be that gradient is a normal hexane: acetone (v/v)=5: 5,4: 6,3: 7,2: 8.Each 500mL of elution volume of different gradients.With duplex ball pressurization wash-out, flow velocity is transferred to and is 5mL/min to the maximum, collects 2min/tube (10ml test tube).Adopt TLC and HPLC that the cut of each separated and collected is detected then, determine that cut 78-cut 178 all contains sulforaphen, merges these cuts.Be used for further purifying.
Sephadex LH-20 chromatography: parting material: Sephadex LH-20 (GE), glass column (50 * 1cm).Eluent selects for use acetone as single eluent.The acetone solution of sample usefulness minimal volumes behind the 0.22 μ m organic system filter membrane, uses sample on the wet method excessively.All eluents through the organic membrane filter of 0.45 μ m to remove impurity.The control flow velocity is about 20s/d, and elution volume is generally 2 retention volume, i.e. 100mL eluent wash-out, and sample is just all eluted.Fraction Collector was received a cut in per 1 hour, and the about 5mL of every pipe collects 20 pipes altogether.Sulforaphen mainly be enriched in the 13rd the pipe cut in, the 12nd, 14 the pipe cuts also enrichment a small amount of sulforaphen.
Embodiment
The present invention has carried out 10 kilograms of broccoli seed raw materials and has extracted pilot scale, and its concrete implementing process flow process is as follows:
The 1kg broccoli seed is pulverized the water that the back adds 2kg, add the 1mol/mL hydrochloric acid soln of 200mL and the 1mg/mL ascorbic acid solution of 20mL (pH4 this moment) after the mixing again, stirring the back seals with preservative film, be placed on hydrolysis 8h under 25 ℃ of room temperatures, the sample lyophilize that hydrolysis is good, sample adds 20L acetone, and (ultransonic condition is ultrasonic lixiviate 60min: frequency 40khz in ultrasonic apparatus, power 200W opens 70% grade).With the material suction filtration, filter residue is used the ultrasonic lixiviate 60min of 10L acetone, suction filtration again.Merging filtrate with filtrate vacuum concentration (30 ℃), obtains the sulforaphen crude extract.Use silica gel column chromatography, silica gel 200 orders～300 orders, glass column 50cm * 3cm, gradient is a normal hexane: acetone (v/v)=5: 5,4: 6,3: 7,2: 8, each 500mL of elution volume of different gradients, with duplex ball pressurization wash-out, flow velocity is transferred to and is 5mL/min to the maximum, collects 2min/tube (10ml test tube); Collect cut 78-cut 178 (detect determine to contain sulforaphen through thin-layer chromatography or HPLC) and with its merging.At the elutriant of the above-mentioned collection of 30 ℃ of condition vacuum concentration, again with small amount of acetone dissolving, cross 0.22 μ m organic system filter membrane after, use sample on the wet method, eluent through the organic membrane filter of 0.45 μ m to remove impurity.Sephadex LH-20 column chromatography (Sephadex LH-20, glass column 50cm * 1cm), acetone is eluent, and flow rate control is about 20s/d, and elution volume is 2 retention volume, i.e. 100mL eluent wash-out, and sample is just all eluted.Fraction Collector was received a cut in per 1 hour, the about 5mL of every pipe, collect 20 pipes altogether, detect definite the 13rd pipe cut of collecting through thin-layer chromatography or HPLC, 12nd, 14 pipe cuts contain a small amount of sulforaphen, collection is used for next column chromatography, and 30 ℃ of vacuum concentration of the 13rd pipe cut liquid are obtained the sulforaphen product.
The product that is extracted determines it is sulforaphen through the GC/MS qualitative detection, and the purity that detects sulforaphen through HPLC has reached 80.395%.Per kilogram broccoli seed raw material can get 1.4 gram left and right sides sulforaphens.
Use radish, broccoli, leaf mustard seed to be raw material,, also can obtain purity and be the sulforaphen more than 80% through the processing of the inventive method.
Claims (4)
1. method of extracting sulforaphen is characterized in that following steps:
(1) be raw material with broccoli seed, add 2～3 times of water gagings by weight after it is pulverized, regulate pH3.8～4.2, hydrolysis is 7～9 hours under 20～30 ℃ of conditions;
(2) with the broccoli seed stoste lyophilize powdering after the hydrolysis;
(3) in the powdery hydrolyzate, add 15～25 times of amount acetone solvents by volume, ultrasonic lixiviate 40～80 minutes, suction filtration or double gauze filter;
(4) filtrate vacuum concentration under 30～50 ℃ of conditions is obtained the sulforaphen crude product;
(5) with the sulforaphen crude product through silica gel column chromatography, adopt normal hexane acetone soln gradient elution, thin-layer chromatography or HPLC detect the cut of determining to contain sulforaphen, vacuum concentration under 30～50 ℃ of conditions;
(6) with the sulforaphen of above-mentioned vacuum concentration with the small amount of acetone dissolving after, with Sephadex LH-20 column chromatography, be eluent with acetone, thin-layer chromatography or HPLC detect and determine and collect to contain sulforaphen liquid, through 30～50 ℃ of vacuum concentration, obtain the sulforaphen product again.
2. a kind of according to claim 1 method of extracting sulforaphen, it is characterized in that the concrete prescription of the described normal hexane acetone soln of step (5) gradient elution is: by volume, normal hexane: acetone was respectively 5: 5, and 4: 6,3: 7,2: 8.
3. a kind of according to claim 1 method of extracting sulforaphen is characterized in that in the hydrating solution of step (1), adds 0.02 gram xitix by the per kilogram raw material.
4. a kind of according to claim 1 method of extracting sulforaphen is characterized in that the condition of the described ultrasonic lixiviate of step (3) is: frequency 40khz, power 200W opens 70% grade.
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| CNA2007101561408A CN101143842A (en) | 2007-10-19 | 2007-10-19 | Method for extracting sulforaphen |
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Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898341A (en) * | 2012-10-26 | 2013-01-30 | 贵州大学 | Extracting and purifying method of high-purity sulforaphane |
| CN103169749A (en) * | 2013-04-13 | 2013-06-26 | 湘西新金凤凰农业开发有限公司 | Broccoli leftover extractive and preparation method thereof |
| CN103272033A (en) * | 2013-04-16 | 2013-09-04 | 阚兆云 | Traditional Chinese medicine extract and preparation method thereof |
| CN103416688A (en) * | 2013-03-07 | 2013-12-04 | 华中农业大学 | Rich-in-sulforaphane broccoli sprout powder and production method thereof |
| CN103436565A (en) * | 2013-09-10 | 2013-12-11 | 甘肃农业大学 | Method for extracting sulforaphane from broccoli |
| CN103995064A (en) * | 2014-05-29 | 2014-08-20 | 中国计量学院 | HPLC (High Performance Liquid Chromatograph) quantitative detection method for raphanin of raphanin extract |
| CN104059947A (en) * | 2014-06-03 | 2014-09-24 | 重庆海巨农业发展有限公司 | Method for preparing high-purity sulforaphane |
| CN104086468A (en) * | 2014-05-22 | 2014-10-08 | 浙江大学苏州工业技术研究院 | Method for supercritical carbon dioxide extraction of sulforaphane |
| CN104152504A (en) * | 2014-08-03 | 2014-11-19 | 重庆海巨农业发展有限公司 | New preparation method of 1-isothiocyanic acid-4-methanesulfonyl-(2-ene) butane |
| CN106214721A (en) * | 2016-08-24 | 2016-12-14 | 徐金蝶 | A kind of preparation method of sulforaphen health-care tablet |
| CN106344625A (en) * | 2016-08-24 | 2017-01-25 | 徐金蝶 | Raphanin-containing healthcare product and preparation method thereof |
| CN106588724A (en) * | 2016-12-02 | 2017-04-26 | 湖南农业大学 | Method for preparing sulforaphen by virtue of subcritical fluid extraction |
| CN107173732A (en) * | 2017-05-31 | 2017-09-19 | 江苏朸健生命科技发展有限公司 | It is a kind of suitable for composite nutrition powder of tumors of nutrients and preparation method thereof |
| CN107988280A (en) * | 2018-01-08 | 2018-05-04 | 湖南农业大学 | The method that isothiocyanates high sterling is obtained through refining from brassicaceous vegetable seed |
| CN108541912A (en) * | 2018-04-13 | 2018-09-18 | 浙江依思味生物科技有限公司 | A kind of anti-oxidant blood-fat reducing composition and its preparation method and application |
| CN108912024A (en) * | 2018-06-27 | 2018-11-30 | 中国农业科学院农产品加工研究所 | The extracting method of sulforaphen |
| CN110256317A (en) * | 2019-07-15 | 2019-09-20 | 河西学院 | It is the method that hydrolysis medium prepares sulforaphen based on eutectic solvent |
| WO2022037675A1 (en) * | 2020-08-20 | 2022-02-24 | 普洱祺云生物科技有限公司 | Preparation method for extract rich in sulforaphane and use thereof |
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2007
- 2007-10-19 CN CNA2007101561408A patent/CN101143842A/en active Pending
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102898341A (en) * | 2012-10-26 | 2013-01-30 | 贵州大学 | Extracting and purifying method of high-purity sulforaphane |
| CN103416688B (en) * | 2013-03-07 | 2014-11-19 | 华中农业大学 | Rich-in-sulforaphane broccoli sprout powder and production method thereof |
| CN103416688A (en) * | 2013-03-07 | 2013-12-04 | 华中农业大学 | Rich-in-sulforaphane broccoli sprout powder and production method thereof |
| CN103169749A (en) * | 2013-04-13 | 2013-06-26 | 湘西新金凤凰农业开发有限公司 | Broccoli leftover extractive and preparation method thereof |
| CN103272033A (en) * | 2013-04-16 | 2013-09-04 | 阚兆云 | Traditional Chinese medicine extract and preparation method thereof |
| CN103436565A (en) * | 2013-09-10 | 2013-12-11 | 甘肃农业大学 | Method for extracting sulforaphane from broccoli |
| CN103436565B (en) * | 2013-09-10 | 2015-08-19 | 甘肃农业大学 | A kind of method extracting sulforaphen from Caulis et Folium Brassicae capitatae |
| CN104086468A (en) * | 2014-05-22 | 2014-10-08 | 浙江大学苏州工业技术研究院 | Method for supercritical carbon dioxide extraction of sulforaphane |
| CN103995064A (en) * | 2014-05-29 | 2014-08-20 | 中国计量学院 | HPLC (High Performance Liquid Chromatograph) quantitative detection method for raphanin of raphanin extract |
| CN103995064B (en) * | 2014-05-29 | 2016-04-06 | 中国计量学院 | The HPLC quantitative detecting method of sulforaphen in sulforaphen extract |
| CN104059947A (en) * | 2014-06-03 | 2014-09-24 | 重庆海巨农业发展有限公司 | Method for preparing high-purity sulforaphane |
| CN104152504A (en) * | 2014-08-03 | 2014-11-19 | 重庆海巨农业发展有限公司 | New preparation method of 1-isothiocyanic acid-4-methanesulfonyl-(2-ene) butane |
| CN106214721A (en) * | 2016-08-24 | 2016-12-14 | 徐金蝶 | A kind of preparation method of sulforaphen health-care tablet |
| CN106344625A (en) * | 2016-08-24 | 2017-01-25 | 徐金蝶 | Raphanin-containing healthcare product and preparation method thereof |
| CN106588724A (en) * | 2016-12-02 | 2017-04-26 | 湖南农业大学 | Method for preparing sulforaphen by virtue of subcritical fluid extraction |
| CN107173732A (en) * | 2017-05-31 | 2017-09-19 | 江苏朸健生命科技发展有限公司 | It is a kind of suitable for composite nutrition powder of tumors of nutrients and preparation method thereof |
| CN107988280A (en) * | 2018-01-08 | 2018-05-04 | 湖南农业大学 | The method that isothiocyanates high sterling is obtained through refining from brassicaceous vegetable seed |
| CN107988280B (en) * | 2018-01-08 | 2021-03-02 | 湖南农业大学 | Method for extracting high-purity isothiocyanate from cruciferous vegetable seeds |
| CN108541912A (en) * | 2018-04-13 | 2018-09-18 | 浙江依思味生物科技有限公司 | A kind of anti-oxidant blood-fat reducing composition and its preparation method and application |
| CN108912024A (en) * | 2018-06-27 | 2018-11-30 | 中国农业科学院农产品加工研究所 | The extracting method of sulforaphen |
| CN110256317A (en) * | 2019-07-15 | 2019-09-20 | 河西学院 | It is the method that hydrolysis medium prepares sulforaphen based on eutectic solvent |
| WO2022037675A1 (en) * | 2020-08-20 | 2022-02-24 | 普洱祺云生物科技有限公司 | Preparation method for extract rich in sulforaphane and use thereof |
| CN115066416A (en) * | 2020-08-20 | 2022-09-16 | 普洱祺云生物科技有限公司 | Preparation method and application of sulforaphane-rich extract |
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