CN107501354B - A method of extracting high-purity glucorphanin - Google Patents
A method of extracting high-purity glucorphanin Download PDFInfo
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- CN107501354B CN107501354B CN201710712008.4A CN201710712008A CN107501354B CN 107501354 B CN107501354 B CN 107501354B CN 201710712008 A CN201710712008 A CN 201710712008A CN 107501354 B CN107501354 B CN 107501354B
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- glucorphanin
- purity
- broccoli seeds
- degreasing
- concentrated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
Abstract
The present invention relates to a kind of methods for extracting high-purity glucorphanin, comprising the following steps: (1) broccoli seeds enzyme deactivation；(2) broccoli seeds crush after enzyme deactivation；(3) petroleum ether extraction broccoli seeds degreasing；(4) water extracts the broccoli seeds after degreasing, obtains aqueous extract；(5) aqueous extract is concentrated, alcohol precipitation, filtering, obtains filtrate；(6) filtrate is concentrated to, is spray-dried the glucorphanin product of high-purity to obtain the final product.Compared with prior art, the present invention uses simple extraction separating method, simple for process, it is easy industrialization, entire technique is cheap, small investment, and the glucorphanin product (purity is greater than 75%) of high-purity can be obtained, highest yield is 3.5%.
Description
Technical field
The present invention relates to a kind of natural products purification process, more particularly, to a kind of side for extracting high-purity glucorphanin
Method.
Background technique
Glucorphanin (Glucoraphanin) is widely present in crucifer, such as
[Chinese agronomy notification, 2008,24 (2): 335- such as broccoli, collard, brussels sprout, cauliflower, horseradish, Chinese cabbage
338；Food science and technology, 2009,34 (12): 250-252], wherein it is most with effective component in broccoli, cauliflower, it is especially western
Content highest in cymbidium seed.The main sulforaphen of the catabolite of glucorphanin, sulforaphen nitrile, Ru zolidine thione etc.,
Highest middle content is sulforaphen [food science and technology, 2009,34 (12): 250-252].Sulforaphen is so far in vegetables
It was found that the strongest a kind of isothiocyanate of anticancer vigor, be the best natural products of generally acknowledged at present anti-cancer and anticancer effect
One of.It is able to suppress I phase enzyme and induces the expression of II phase enzyme, to liver cancer, breast cancer, lung cancer, cancer of the esophagus, prostate cancer, gastric cancer
There is apparent blocking effect, and sulforaphen also has protection skin, antibacterial, improves antioxidant ability of organism and immunity etc.
Pharmacological action [food fermentation and industry, 2011,37 (7): 197-200].But sulforaphen is very unstable, and glucorphanin compares
Stablize, and sulforaphen etc. can be hydrolyzed into vivo, therefore the separating-purifying for studying glucorphanin is very necessary
's.
China has carried out some research to the separation of glucorphanin, but obtains the radish of high-purity by simple method
The research of sulphur glycosides is few, and the glucorphanin for largely obtaining high-purity requires to carry out resin column or chromatography post separation.Such as patent
CN103709211, which successively passes through macroreticular resin, silica gel post separation just, can obtain the glucorphanin of high-purity.Patent
CN102295667 can just obtain high-purity glucorphanin after repeatedly extracting and preparing chromatography post separation.Using resin point
From or chromatography post separation can all lead to increased costs, process flow is elongated.
Chinese patent CN105566409A discloses a kind of method that separation glucorphanin is extracted from broccoli seed, packet
It includes following steps: (1) extracting glucorphanin solution from broccoli seed, and be concentrated to give glucorphanin concentration
Liquid；(2) glucorphanin concentrate is adsorbed with macroporous absorbent resin；(3) macroporous absorbent resin is carried out with ethanol solution
Elution, obtains resin eluent；(4) after resin eluent being concentrated, silica gel mixing is added, volatilize ethyl alcohol, is adsorbed
The silica gel of glucorphanin, and added to and the resulting silicagel column upper layer of column is filled out by silica gel；(5) silicagel column is washed with eluant, eluent
It is de-, eluent is collected, and eluent is concentrated, is dried to get glucorphanin product.Although the radish sulphur that the patent obtains
Glycosides purity is higher, but by macroporous absorbent resin and silica gel post separation, needs to elute by 2 upper props and solvent, process phase
To cumbersome, solvent consumption is more, and the operation cycle is long.
Therefore, it finds a kind of process for separation and purification by cheap and simple and obtains the glucorphanin product of high-content, it will be right
Exploitation, which has using glucorphanin as the development of the drug of main active and health care product, actively promotes effect.
Summary of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide a kind of easy to operate, costs
The method of cheap extraction high-purity glucorphanin.
The purpose of the present invention can be achieved through the following technical solutions:
A method of extracting high-purity glucorphanin, comprising the following steps:
(1) broccoli seeds enzyme deactivation；
(2) broccoli seeds crush after enzyme deactivation；
(3) petroleum ether extraction broccoli seeds degreasing；
(4) water extracts the broccoli seeds after degreasing, obtains aqueous extract；
(5) aqueous extract is concentrated, alcohol precipitation, filtering, obtains filtrate；
(6) filtrate is concentrated to, is spray-dried the glucorphanin product of high-purity to obtain the final product.
The method of step (1) the broccoli seeds enzyme deactivation are as follows: dry broccoli seed is taken, in 80-110 DEG C of oven
20min-60min。
The method that broccoli seeds crush after step (2) described enzyme deactivation are as follows: broccoli seeds after enzyme deactivation are carried out using pulverizer
It crushes, makes its granularity 5-100 mesh.
The method of step (3) the petroleum ether extraction broccoli seeds degreasing are as follows: petroleum ether is added in the broccoli seeds of crushing
In 40-68 DEG C of heating degreasing 0.5-2h, the mass ratio of petroleum ether and broccoli seeds is 2-10:1.
The method that step (4) water extracts the broccoli seeds after degreasing are as follows: by the broccoli seeds deionization after degreasing
Water is extracted in 60-100 DEG C, and extraction time is 1-3 times, each 0.5-2h, and the mass ratio of deionized water and broccoli seeds is 2-8:
1, obtain aqueous extract.
Step (5) described aqueous extract is concentrated, alcohol precipitation, filtering method are as follows: glucorphanin aqueous extract is in rotation
Evaporimeter is concentrated, and concentrate is obtained, and 95% ethyl alcohol, static 2-24h are added in concentrate, and filtering obtains filtrate, wherein trailing plants
Foretell sulphur glycosides extracting liquid volume: the volume of the concentrated liquid: 95% ethyl alcohol volume is 3-10:0.5-3:1.
Dry method in step (6) are as follows: concentrate the filtrate to 0.1-0.5 times of original volume, spray drying is high to get arriving
Purity glucorphanin product, purity are greater than 75%.
The present invention is not necessarily to through post separation, without considering the dissolvent residual of the fillers such as possible resin, using simple extraction
Separation is taken, after the grease that broccoli seeds are sloughed by petroleum ether, water extracts glucorphanin, and alcohol precipitation removes impurity, entire mistake again
Journey separation scale is bigger, and easy to operate, the period is short, and what it is using solvent is petroleum ether, second alcohol and water, and solvent usage amount is few, valence
Lattice are cheap, at low cost, and product purity is also relatively high, reach 75% or more, in terms of can satisfy general drug and food
Demand, and have very high yield, highest can achieve 3.5%, than patent CN105566409A highest yield (yield)
1.2% is much higher.
Compared with prior art, the present invention uses simple extraction separating method, simple for process, is easy industrialization,
Entire technique is cheap, small investment, and can obtain the glucorphanin product (purity is greater than 75%) of high-purity, and highest obtains
Rate is 3.5%.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.
Embodiment 1
(1) dry broccoli seeds 200g is taken, in 105 DEG C of oven 30min, is then crushed to 20 mesh with pulverizer,
500g petroleum ether is added, is heated to 60 DEG C of extraction 1h, filters, obtains the broccoli seeds of degreasing.
(2) 1000g deionized water being added in 80 DEG C of extraction 2h in the broccoli seeds after degreasing, filtering repeats to extract 1 time,
Combined extract.
(3) glucorphanin extracting solution is concentrated in Rotary Evaporators, is concentrated into 200mL, be added 200mL95% ethyl alcohol into
Row alcohol precipitation, after static 12h, filtering obtains filtrate.
(4) filtrate is concentrated into 100mL, and spray drying obtains glucorphanin product, purity 76.3%, yield is
3.4%.
Embodiment 2
(1) dry broccoli seeds 200g is taken, in 100 DEG C of oven 50min, is then crushed to 20 mesh with pulverizer,
600g petroleum ether is added, is heated to 60 DEG C of extraction 1h, filters, obtains the broccoli seeds of degreasing.
(2) 1000g deionized water is added in 80 DEG C of extraction 2h in the broccoli seeds after degreasing, filtering obtains extracting solution.
(3) glucorphanin extracting solution is concentrated in Rotary Evaporators, is concentrated into 150mL, be added 200mL95% ethyl alcohol into
Row alcohol precipitation, it is static for 24 hours after, filtering, obtain filtrate.
(4) filtrate is concentrated into 100mL, and spray drying obtains glucorphanin product, purity 78.6%, yield is
3.1%.
The above description of the embodiments is intended to facilitate ordinary skill in the art to understand and use the invention.
Person skilled in the art obviously easily can make various modifications to these embodiments, and described herein general
Principle is applied in other embodiments without having to go through creative labor.Therefore, the present invention is not limited to the above embodiments, ability
Field technique personnel announcement according to the present invention, improvement and modification made without departing from the scope of the present invention all should be of the invention
Within protection scope.
Claims (5)
1. a kind of method for extracting high-purity glucorphanin, which comprises the following steps:
(1) broccoli seeds enzyme deactivation；
(2) broccoli seeds crush after enzyme deactivation；
(3) petroleum ether extraction broccoli seeds degreasing；
(4) water extracts the broccoli seeds after degreasing, obtains aqueous extract；
(5) aqueous extract is concentrated, alcohol precipitation, filtering, obtains filtrate；
(6) filtrate is concentrated to, is spray-dried the glucorphanin product of high-purity to obtain the final product；
The method of step (1) the broccoli seeds enzyme deactivation are as follows: dry broccoli seed is taken, in 80-110 DEG C of oven
20min-60min；
The method of step (3) the petroleum ether extraction broccoli seeds degreasing are as follows: petroleum ether is added in 40- in the broccoli seeds of crushing
The mass ratio of 68 DEG C of heating degreasing 0.5-2h, petroleum ether and broccoli seeds is 2-10:1.
2. a kind of method for extracting high-purity glucorphanin according to claim 1, which is characterized in that step (2) is described
The method that broccoli seeds crush after enzyme deactivation are as follows: broccoli seeds after enzyme deactivation are crushed using pulverizer, make its granularity 5-100
Mesh.
3. a kind of method for extracting high-purity glucorphanin according to claim 1, which is characterized in that step (4) is described
The method that water extracts the broccoli seeds after degreasing are as follows: the broccoli seeds deionized water after degreasing is extracted in 60-100 DEG C, is mentioned
Taking number is 1-3 times, each 0.5-2h, and the mass ratio of deionized water and broccoli seeds is 2-8:1, obtains aqueous extract.
4. a kind of method for extracting high-purity glucorphanin according to claim 1, which is characterized in that step (5) is described
Aqueous extract is concentrated, alcohol precipitation, filtering method are as follows: glucorphanin aqueous extract is concentrated in Rotary Evaporators, is obtained
Concentrate, 95% ethyl alcohol, static 2-24h are added in concentrate, and filtering obtains filtrate, wherein glucorphanin extracting liquid volume: dense
Contracting liquid product: 95% ethyl alcohol volume is 3-10:0.5-3:1.
5. a kind of method for extracting high-purity glucorphanin according to claim 1, which is characterized in that done in step (6)
Dry method are as follows: 0.1-0.5 times of original volume is concentrated the filtrate to, is spray-dried to get high-purity glucorphanin product is arrived, it is pure
Degree is greater than 75%.
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| CN201710712008.4A CN107501354B (en) | 2017-08-18 | 2017-08-18 | A method of extracting high-purity glucorphanin |
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| CN201710712008.4A CN107501354B (en) | 2017-08-18 | 2017-08-18 | A method of extracting high-purity glucorphanin |
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| CN107501354A CN107501354A (en) | 2017-12-22 |
| CN107501354B true CN107501354B (en) | 2019-11-26 |
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| CN110066776B (en) * | 2019-04-19 | 2021-06-01 | 乐山师范学院 | Method for extracting sulforaphane and myrosinase magnetic microspheres |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102295667B (en) * | 2011-06-28 | 2014-07-30 | 浙江省农业科学院 | Method for extracting glucoraphanin compound from broccoli and cauliflower |
| CN103768122B (en) * | 2014-02-13 | 2015-11-11 | 山东中医药大学 | A kind of method extracting total sulfur glycosides position from Semen Raphani |
| CN105566409B (en) * | 2016-02-05 | 2018-11-09 | 赣州华汉生物科技有限公司 | A method of the extraction separation glucorphanin from broccoli seed |
| CN105713053B (en) * | 2016-03-26 | 2018-09-21 | 北京化工大学 | A kind of glucosinolate extraction separation method |
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