CN102898341A - Extracting and purifying method of high-purity sulforaphane - Google Patents
Extracting and purifying method of high-purity sulforaphane Download PDFInfo
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- CN102898341A CN102898341A CN2012104149942A CN201210414994A CN102898341A CN 102898341 A CN102898341 A CN 102898341A CN 2012104149942 A CN2012104149942 A CN 2012104149942A CN 201210414994 A CN201210414994 A CN 201210414994A CN 102898341 A CN102898341 A CN 102898341A
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Abstract
The invention discloses a method for extracting high-purity sulforaphane from broccoli seeds; and the method comprises the following steps of: (1) after crushing dry broccoli seeds, adding water to the dry broccoli seeds to hydrolyze the broccoli seeds, so as to obtain a solid-liquid mixture; (2) adding anhydrous ethanol to the mixture; ultrasonically extracting the mixture; and carrying out suction filtration or double-layer gauze filtering on the mixture; (3) concentrating and evaporating ethanol from a filter liquor in a vacuum state; (4) carrying out chromatography on a material liquor by using a macroporous resin column and eluting the material liquor by using an ethanol solution in a gradient way; (5) collecting an eluting solution containing sulforaphane; carrying out chromatography on the eluting solution by using an alumina column; and concentrating a sulforaphane chromatography solution to form an extract so as to obtain a crude sulforaphane product; (6) adding water to the obtained crude product so as to dissolve the crude product; and extracting the dissolved crude product by using a polar solvent; and (7) collecting an organic layer; and concentrating the organic layer in a vacuum state so as to obtain an oily extract, so that the high-purity sulforaphane is obtained. As the high-purity sulforaphane can be directly extracted from the broccoli seeds and broccoli related materials, the method for extracting the high-purity sulforaphane from the broccoli seeds, disclosed by the invention, has the advantages of simple process, stable product, simple equipment and safety in production and is suitable for enterprises for industrially extracting the sulforaphane.
Description
Technical field
The present invention relates to extract the method for effective constituent in the purifying natural product, in particular to the method for from broccoli seed, extracting the high purity sulforaphen.
Background technology
According to World Health Organization statistics, the annual number because of cancer mortality in the whole world is up to 7,000,000 at present.But up to now, people not yet find the way of capturing cancer.Therefore, research and control tumour are the key subjects of current life science.Epidemiology and pharmaceutical research show: the place that cancer morbidity is low, the vegetables in people's diet, fruit proportion are larger.Trace it to its cause, to have one or more preventions in the vegetable and fruit or slow down the activeconstituents of cancer development, such as the Lyeopene in the tomato, soybean isoflavones, tanning acid in the berry and the sulforaphen in the Cruciferae vegetables and fruits in the soya products, indoles material, all confirmed to have good anti-cancer and kill cancer action.In numerous vegetables that contain anticancer active constituent, Cruciferae (cabbage, asparagus broccoli, kohlrabi, blue and white cabbage, cabbage mustard, 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, also is the strongest anticancer component of finding in the vegetables up to now.
Caulis et Folium Brassicae capitatae has another name called Broccoliflorets, broccoli etc., for the Cruciferae rape belongs to a mutation take green bouquet as product in the brassica specie.Studies show that, contain abundant sulforaphen in the Caulis et Folium Brassicae capitatae, can be effectively to anti-breast cancer and large bowel cancer.Healthy people often eat the effect that Caulis et Folium Brassicae capitatae also can play preventing cancer.Therefore, Caulis et Folium Brassicae capitatae is described as " anti-cancer rising star ".
Have at present some and from Caulis et Folium Brassicae capitatae, extract the patent application of sulforaphen, for example " a kind of method (CN101143842) of extracting sulforaphen ", " a kind of broccoli seed extractive and preparation method thereof (CN101229211) ", " a kind of preparation method of sulforaphane (CN1982294) ", " a kind of extracting method of sulforaphen (CN101544995) " all disclose extraction and the purification process of effective active composition sulforaphen in the broccoli seed.The problem that these methods exist has: all adopt silica gel column chromatography in the purge process, use C again
18Preparative chromatography or gel column come the purifying sulforaphen, use poisonous organic solvent wash-out in the silicagel column developping agent, also there is inflammable and explosive problem in production process, add the defectives such as the column chromatography material regeneration is difficult, cause above-mentioned patent to be only suitable for short run and the laboratory prepares usefulness, be unsuitable for suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide a kind of method of from broccoli seed, extracting high-purity sulforaphen, overcoming the defective that prior art can not suitability for industrialized production, thereby lay the first stone for the sulforaphen that will extract from broccoli seed is used for human anti-curing cancers.
The contriver is through after systematic research and testing, and the method for proposition may further comprise the steps:
(1) is raw material with dry broccoli seed, adds water after the pulverizing; In warm water, be hydrolyzed, obtain solidliquid mixture;
(2) add dehydrated alcohol in the solidliquid mixture after the hydrolysis, ultrasonic lixiviate, suction filtration or double gauze filter;
(3) with filtrate concentration and evaporation ethanol under vacuum condition;
(4) will remove the rear feed liquid homopolarity macroporous resin column chromatography of alcohol, be that eluent carries out gradient elution with aqueous ethanolic solution, and selective collection contains the sulforaphen elutriant;
(5) will obtain the sulforaphen elutriant, the sulforaphen chromatographic solution is collected in peroxidation aluminium dry chromatography decolouring, again through vacuum concentration to oily medicinal extract, namely obtain purity and be 60% sulforaphen;
(6) being obtained purity the upper step is 60% sulforaphen medicinal extract, after being dissolved in water, adopts organic solvent to extract;
(7) discard water layer after the extraction, organic layer carries out vacuum concentration, namely gets purity greater than 90% sulforaphen extract.
In the above-mentioned steps (1), described broccoli seed is crushed to 30～60 orders; The described quality that adds water is 1.5～2 times of seed powder quality; The temperature of described warm water is 25 ℃～35 ℃; Described hydrolysis time is 7～9h.
In the above-mentioned steps (2), the quality of described adding dehydrated alcohol is 8～8.5 times of solidliquid mixture quality; Described ultrasonic extraction time is 30～60min, ultrasonic lixiviate frequency 40kHz, power 200W.
In the above-mentioned steps (3), the vacuum tightness when concentrated under the described vacuum condition is-0.06～-0.08MPa, temperature is 30 ℃～40 ℃.
In the above-mentioned steps (4), the model of described homopolarity macroporous resin is AB-8, DM-130, D101; The massfraction of the ethanolic soln of described gradient elution is respectively 30%, 50%, 70%.
In the above-mentioned steps (5), the vacuum tightness during described vacuum concentration is-0.06～-0.08MPa, temperature is 30 ℃～40 ℃.
In the above-mentioned steps (6), the described amount that is dissolved in water is 10 times of amounts of medicinal extract amount; Described organic solvent is ethyl acetate or methylene dichloride and ethanol according to the mixed solvent that forms at 1: 1; Described extraction times is 3 times, and the amount that extracts used organic solvent is the doubling dose of water layer feed liquid.
In the above-mentioned steps (7), the vacuum tightness of controlling during described vacuum concentration is-0.06～-0.08MPa.
The contriver points out, technological step of the present invention can be summarized as follows: broccoli seed adds 1.5～2 times in water after being crushed to 30～60 orders, under 25 ℃～35 ℃ temperature, be hydrolyzed 7～9h, add ultrasonic lixiviate 30～60min behind 8～8.5 times the dehydrated alcohol in the solidliquid mixture after the hydrolysis, Plate Filtration (double gauze), vacuum concentration removes alcohol under 30 ℃～40 ℃ conditions, (gradient is 30% with macroporous resin column chromatography to remove extracting solution behind the alcohol, 50%, 70% aqueous ethanolic solution), collection contains the liquid (determining through the HPLC detection) of sulforaphen, elutriant peroxidation aluminium dry chromatography is collected chromatographic solution; Vacuum concentration is to medicinal extract under 30 ℃～40 ℃ conditions, obtains purity and be 60% sulforaphen, add the suitable quantity of water dissolving after, adopt organic solvent to extract, discard water layer, the organic layer vacuum concentration namely gets purity greater than 90% sulforaphen extract.
The inventive method can be from broccoli seed directly dna purity have that technical process is simple, an easy advantage of suitability for industrialized production such as constant product quality, use reagent safety and production unit are simple greater than high-purity sulforaphen of 90%.Be applicable to take the enterprise of broccoli seed as primary industry extraction sulforaphen.
Embodiment
Embodiment 1
Get broccoli seed 100g, be crushed to 30～60 orders after, add water 200ml; Under 35 ℃ temperature, be hydrolyzed 8h, add dehydrated alcohol 800ml, ultrasonic lixiviate 30min, ultrasonic lixiviate frequency 40kHz, power 200W; Then adopt double gauze to filter;
With filtrate vacuum concentration ethanol evaporation under 40 ℃ of conditions; Adopt the mode of suction filtration to be filtered to limpid, with limpid rear feed liquid 150mL, use the AB-8 macroporous resin column chromatography, be that 30% ethanol 400mL removes impurity with massfraction, and discard elutriant, be sulforaphen on 50% the ethanol 600mL wash-out macroporous resin chromatography column with massfraction again, collect elutriant, use again alumina column chromatography, and collect the sulforaphen elutriant, and vacuum concentration is to oily medicinal extract under 40 ℃ of conditions again, and the concentrated oily matter that takes by weighing 5mg dissolves with methyl alcohol 10ml, detect with HPLC, sulforaphen purity is 60% in the product again.
The purity that the upper step was obtained is after 60% the sulforaphen medicinal extract suitable quantity of water dissolving, to adopt ethyl acetate to extract 3 times, discards water layer, collected organic layer, and under 40 ℃, vacuum-0.08MPa condition, be concentrated into oily medicinal extract; Take by weighing the concentrated oily matter of 5mg with methyl alcohol 10mL dissolving, detect with HPLC again, namely get purity greater than 90% sulforaphen extract.
Embodiment 2
Get broccoli seed 100g, be crushed to 30～60 orders after, add water 200mL; Under 35 ℃ temperature, be hydrolyzed 10h, add dehydrated alcohol 800mL, ultrasonic lixiviate 30min, ultrasonic lixiviate frequency 40kHz, power 200W; Then adopt double gauze to filter;
With filtrate vacuum concentration ethanol evaporation under 40 ℃ of conditions; Adopt the mode of suction filtration to be filtered to limpid, with limpid rear feed liquid 150mL, use the DM130 macroporous resin column chromatography, be that 30% ethanol 400mL removes impurity with massfraction, and discard elutriant, be sulforaphen on 50% the ethanol 600mL wash-out macroporous resin chromatography column with massfraction again, collect elutriant, use again alumina column chromatography, and collect the sulforaphen elutriant, and vacuum concentration is to oily medicinal extract under 40 ℃ of conditions again, and the concentrated oily matter that takes by weighing 5mg dissolves with methyl alcohol 10mL, detect with HPLC, sulforaphen purity is 60% in the product again.
After the upper step obtained 60% purity sulforaphen medicinal extract suitable quantity of water dissolving, adopt methylene dichloride and ethanol 1:1 mixed solvent to extract 3 times, collected organic layer, and under 40 ℃, vacuum-0.06MPa condition, be concentrated into oily medicinal extract, the concentrated oily matter that takes by weighing 5mg dissolves with methyl alcohol 10mL, detect with HPLC again, namely get purity greater than 90% sulforaphen extract.
Claims (8)
1. method of from broccoli seed, extracting high-purity sulforaphen, its feature may further comprise the steps:
⑴ be raw material with dry broccoli seed, adds water after the pulverizing; In warm water, be hydrolyzed, obtain solidliquid mixture;
⑵ add dehydrated alcohol in the solidliquid mixture after the hydrolysis, ultrasonic lixiviate, suction filtration or double gauze filter;
⑶ with filtrate concentration and evaporation ethanol under vacuum condition;
⑷ will remove the rear feed liquid homopolarity macroporous resin column chromatography of alcohol, be that eluent carries out gradient elution with aqueous ethanolic solution, and selective collection contains the sulforaphen elutriant;
⑸ will obtain the sulforaphen elutriant, and the sulforaphen chromatographic solution is collected in peroxidation aluminium dry chromatography decolouring, again through vacuum concentration to oily medicinal extract, namely obtain purity and be 60% sulforaphen;
(6) being obtained purity the upper step is 60% sulforaphen medicinal extract, after being dissolved in water, adopts organic solvent to extract;
(7) discard water layer after the extraction, organic layer carries out vacuum concentration, namely gets purity greater than 90% sulforaphen extract.
2. in accordance with the method for claim 1, it is characterized in that described broccoli seed is crushed to 30～60 orders in the step (1); The described quality that adds water is 1.5～2 times of seed meal quality; The temperature of described warm water is 25 ℃～35 ℃; Described hydrolysis time is 7～9h.
3. in accordance with the method for claim 1, it is characterized in that in the step (2) that the quality of described adding dehydrated alcohol is 8～8.5 times of solidliquid mixture quality; Described ultrasonic extraction time is 30～60 minutes, ultrasonic lixiviate frequency 40kHz, power 200W.
4. in accordance with the method for claim 1, it is characterized in that in the step (3), the vacuum tightness when concentrated under the described vacuum condition be-0.06 MPa extremely-0.08MPa, temperature is 30 ℃～40 ℃.
5. in accordance with the method for claim 1, it is characterized in that in the step (4) that described homopolarity macroporous resin is a kind of among AB-8, DM-130, the D101; The ethanolic soln concentration of described gradient elution is respectively 30%, 50%, 70%.
6. in accordance with the method for claim 1, it is characterized in that in the step (5) that the vacuum tightness during described vacuum concentration is-0.06 MPa to-0.08MPa, temperature is 30 ℃～40 ℃.
7. in accordance with the method for claim 1, it is characterized in that in the step (6) that the described amount that is dissolved in water is 10 times of amounts of medicinal extract amount; Described organic solvent is ethyl acetate or methylene dichloride and ethanol according to the mixed solvent that forms at 1: 1; Described extraction times is 3 times, and the amount that extracts used organic solvent is the doubling dose of water layer feed liquid.
8. in accordance with the method for claim 1, it is characterized in that in the step (7), the vacuum tightness of controlling during described vacuum concentration is-0.06～-0.08MPa.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN104086469A (en) * | 2014-05-22 | 2014-10-08 | 苏州泽达兴邦医药科技有限公司 | Method for extracting and purifying sulforaphane from broccoli seeds |
| CN104130171A (en) * | 2013-05-02 | 2014-11-05 | 西安瑞德生物科技有限公司 | Preparation method 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 |
| CN104372045A (en) * | 2014-11-10 | 2015-02-25 | 安徽大学 | Preparation method of high-purity sulforaphen |
| CN106632520A (en) * | 2016-09-29 | 2017-05-10 | 临沂大学 | Method for preparing high-purity reduced glucoraphanin from radish |
| CN109394729A (en) * | 2018-12-11 | 2019-03-01 | 曲阜师范大学 | A kind of medicine-carried system and preparation method thereof loading sulforaphen |
| CN109588698A (en) * | 2017-09-30 | 2019-04-09 | 华中科技大学 | A kind of functional food that preventing and treating mental disorder induced by alcoholism and drug and its preparation method |
| CN110201021A (en) * | 2019-05-23 | 2019-09-06 | 佛山市欧若拉生物科技有限公司 | A kind of broccoli seed extraction process |
| CN110433187A (en) * | 2019-08-02 | 2019-11-12 | 广州六顺生物科技股份有限公司 | A kind of Turnip extractive is in preparation treatment, prevention or improves application and its preparation process in treatment parkinsonism |
| CN113512570A (en) * | 2021-05-26 | 2021-10-19 | 劲牌有限公司 | Method for rapidly extracting sulforaphane from broccoli seeds |
| CN116715616A (en) * | 2023-02-13 | 2023-09-08 | 安徽本森堂生物科技有限公司 | Environment-friendly and efficient preparation method of sulforaphane |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104130171A (en) * | 2013-05-02 | 2014-11-05 | 西安瑞德生物科技有限公司 | Preparation method of sulforaphane |
| CN104086469A (en) * | 2014-05-22 | 2014-10-08 | 苏州泽达兴邦医药科技有限公司 | Method for extracting and purifying sulforaphane from broccoli seeds |
| 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 |
| CN104372045B (en) * | 2014-11-10 | 2017-06-20 | 安徽大学 | A kind of preparation method of high-purity sulforaphane |
| CN104372045A (en) * | 2014-11-10 | 2015-02-25 | 安徽大学 | Preparation method of high-purity sulforaphen |
| CN106632520A (en) * | 2016-09-29 | 2017-05-10 | 临沂大学 | Method for preparing high-purity reduced glucoraphanin from radish |
| CN106632520B (en) * | 2016-09-29 | 2019-05-31 | 临沂大学 | A method of high-purity reduced form glucorphanin is prepared by raw material of radish |
| CN109588698A (en) * | 2017-09-30 | 2019-04-09 | 华中科技大学 | A kind of functional food that preventing and treating mental disorder induced by alcoholism and drug and its preparation method |
| CN109394729A (en) * | 2018-12-11 | 2019-03-01 | 曲阜师范大学 | A kind of medicine-carried system and preparation method thereof loading sulforaphen |
| CN110201021A (en) * | 2019-05-23 | 2019-09-06 | 佛山市欧若拉生物科技有限公司 | A kind of broccoli seed extraction process |
| CN110433187A (en) * | 2019-08-02 | 2019-11-12 | 广州六顺生物科技股份有限公司 | A kind of Turnip extractive is in preparation treatment, prevention or improves application and its preparation process in treatment parkinsonism |
| CN113512570A (en) * | 2021-05-26 | 2021-10-19 | 劲牌有限公司 | Method for rapidly extracting sulforaphane from broccoli seeds |
| CN116715616A (en) * | 2023-02-13 | 2023-09-08 | 安徽本森堂生物科技有限公司 | Environment-friendly and efficient preparation method of sulforaphane |
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Application publication date: 20130130 |