CN105566409B - A method of the extraction separation glucorphanin from broccoli seed - Google Patents
A method of the extraction separation glucorphanin from broccoli seed Download PDFInfo
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The method that the present invention relates to a kind of to extract separation glucorphanin from broccoli seed, includes the following steps：(1) glucorphanin solution is extracted from broccoli seed, and is concentrated to give glucorphanin concentrate；(2) glucorphanin concentrate is adsorbed with macroporous absorbent resin；(3) macroporous absorbent resin is eluted with ethanol solution, obtains resin eluent；(4) after being concentrated resin eluent, silica gel mixing is added, volatilize ethyl alcohol, obtains the silica gel of absorption glucorphanin, and added to and fill out the silicagel column upper layer obtained by column by silica gel；(5) silicagel column is eluted with eluant, eluent, collects eluent, and eluent is concentrated, is dried to get glucorphanin product.Compared with prior art, present invention process is simple and practicable, is easy industrialization, macroreticular resin and silica gel are inexpensive, are easy to get, and entire technique is cheap, small investment, and can obtain the glucorphanin product of high-purity.
Description
Technical field
The present invention relates to natural products purification process, and in particular to one kind extraction separation glucorphanin from broccoli seed
Method.
Background technology
Glucorphanin (Glucoraphanin) is widely present in crucifer, such as
[Chinese agronomy notification, 2008,24 (2) such as broccoli, collard, brussels sprout, cauliflower, horseradish, Chinese cabbage:335-
338；Food science and technology, 2009,34 (12):250-252], wherein it is most with active ingredient in broccoli, cauliflower, it is especially western
Content highest in cymbidium seed.The main sulforaphen of catabolite of glucorphanin, sulforaphen nitrile, Ru zolidine thiones etc., wherein containing
It is sulforaphen [food science and technology, 2009,34 (12) to measure highest:250-252].It is found in sulforaphen vegetables so far
The strongest a kind of isothiocyanate of anticancer vigor, is best one of the natural products of generally acknowledged at present anti-cancer and anticancer effect.
It can inhibit I phases enzyme and induce the expression of II phase enzyme, have obviously to liver cancer, breast cancer, lung cancer, cancer of the esophagus, prostate cancer, gastric cancer
Blocking effect, and sulforaphen also have protection skin, antibacterial, improve the pharmacology such as antioxidant ability of organism and immunity make
With [food fermentation and industry, 2011,37 (7):197-200].But sulforaphen is very unstable, and glucorphanin is more stable, and
And it can be hydrolyzed into sulforaphen etc. in vivo, therefore the separating-purifying for studying glucorphanin is very important.
China has carried out the research of some to the separation of glucorphanin, but efficiently separates to obtain the glucorphanin of high-purity at present
Method is few.If patent CN103709211 uses cauliflower to extract separation glucorphanin for raw material, the macropore tree of low pole is first used
Fat for the first time separation after, again use the isolated high-purity of silicagel column glucorphanin, but use raw material glucorphanin content compared with
Low, volume is larger, is not easy storage and transportation, therefore yield is relatively low.Patent CN102295667 is by repeatedly extraction and prepares chromatography post separation
Afterwards, it has obtained high-purity glucorphanin, but has prepared chromatography small scale, it is few that single obtains product volume, is unfavorable for industrialized production.
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 to developing with radish
Sulphur glycosides has for the development of the drug and health products of main active actively promotes effect.
104961667 A of Chinese patent CN disclose a kind of purification process of sulforaphen, and this approach includes the following steps：
(1) sulforaphen solution is prepared；(2) sulforaphen solution is extracted, then extract liquor concentrates, and obtains sulforaphen concentrate；
(3) sulforaphen concentrate is mixed, solvent flashing with diatomite, obtains the diatomite of absorption sulforaphen；(4) it is filled out with diatomite
The diatomite for adsorbing sulforaphen is added to siliceous earth column upper layer by column；(5) it is eluted with eluant, eluent, collects washing for different solvents
De- liquid；(6) eluent concentrated, be drying to obtain absorption sulforaphen product.The invention detaches sulforaphen, technique using diatomite
It is simple and practicable, it is easy industrialization, diatomite is inexpensive, is easy to get, and entire technique is cheap, small investment, and can obtain high-purity
The sulforaphen product of degree (purity is more than 95%).But patent separation is sulforaphen, and sulforaphen is glucorphanin through black mustard
Sub- sulphur neuraminidase enzymolysis or sour water solution, generate an intermediate, and pass through weight under certain condition after taking off a molecule glucose
The isothiocyanate derivatives that group reaction generates.Glucorphanin is different with sulforaphen molecular structure, and property has many differences, therefore
Process for separation and purification is also different.
Invention content
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, environmentally friendly
It is energy saving, purity is high, it is at low cost from broccoli seed extraction separation glucorphanin method.
The purpose of the present invention can be achieved through the following technical solutions：One kind extracting separation radish from broccoli seed
The method of sulphur glycosides, mainly includes the following steps that：
(1) glucorphanin solution is extracted from broccoli seed, and the glucorphanin solution of gained is concentrated to give radish
Sulphur glycosides concentrate；
(2) glucorphanin concentrate obtained by step (1) is adsorbed with macroporous absorbent resin；
(3) macroporous absorbent resin is eluted with ethanol solution, obtains resin eluent；
(4) after being concentrated resin eluent obtained by step (3), silica gel mixing is added, volatilize ethyl alcohol, obtains absorption trailing plants
Foretell the silica gel of sulphur glycosides, and is added to and fill out the silicagel column upper layer obtained by column by silica gel；
(5) silicagel column is eluted with eluant, eluent, collects eluent, and eluent is concentrated, is dried to get trailing plants
Foretell sulphur glycoside product.
Step (1) the glucorphanin solution that extracted from broccoli seed includes the following steps：Take dry broccoli kind
Son is placed in 100-120 DEG C, preferably 105 DEG C, and oven 20min~60min is added ethanol solution after being crushed, is heated to
40~70 DEG C of extraction 30min~2h, filtering, filtrate is glucorphanin solution, and the mass ratio of wherein broccoli seed and ethyl alcohol is
1:(2~10).The myrosinase in broccoli seed is inactivated by high temperature, avoids crushing and subsequent carrying in seed
Enzyme hydrolyzes glucorphanin during taking.Extracted using ethanol solution, one side ethyl alcohol glucorphanin is dissolved it is big, can fully by
Glucorphanin is extracted from seed；Still further aspect, ethyl alcohol is nontoxic, cheap.
Step (1) concentration is that the glucorphanin solution is placed on Rotary Evaporators to be evaporated, until radish
The volume ratio of sulphur glycosides concentrate and glucorphanin solution is 1：(3~10).
Step (2) is described to be included the following steps with the method that macroporous absorbent resin is adsorbed：Macroporous absorbent resin is filled out
Column, obtains resin column, glucorphanin concentrate with 1~5BV/h speed by resin column, wherein the glucorphanin by resin column is dense
The volume of contracting liquid is (2~20) BV, and the macroporous absorbent resin includes the semipolar macroporous absorption tree of DM-301, ADS-17
Fat.The present invention selects the macroporous absorbent resin of semipolar DM-301, ADS-17 to have prodigious adsorbance to glucorphanin, because
Glucorphanin itself has certain polarity, and the adsorbance to it can be improved by semipolar resin.
Step (3) elution includes the following steps：The macroporous absorbent resin for adsorbing glucorphanin is washed with deionized water
It washs, is then eluted with the ethanol solution of (2~20) BV volumes, wherein elution speed is that 1~5BV/h speed passes through resin
Column, a concentration of the 65%~95% of the ethanol solution.In the above conditions, ethanol solution can effectively by glucorphanin from
It is eluted in resin.
Step (4) concentration is evaporated for the eluent to be placed on Rotary Evaporators, until before and after concentration
Eluent volume ratio be 30：1, silica gel, and the ethyl alcohol therein that volatilizees is added in the eluent after concentration, obtains absorption radish sulphur
The silica gel of glycosides, the quality (g) of the silica gel of addition are 1 with the ratio between the volume (mL) of eluent after concentration:1.
Step (4) column of filling out uses wet method dress post, includes the following steps：The silica gel of 200~800 mesh is moistened with petroleum ether
It is wet, it is fitted into glass column, allows silica gel natural subsidence, then lead to nitrogen and be compacted silica gel, release petroleum ether from glass column lower part, so
The silica gel for adsorbing glucorphanin is filled to silicagel column top, wherein petroleum ether and silica gel, the body for the silica gel for adsorbing glucorphanin again afterwards
The ratio between product is (10~30):(5~10):1.It is certain that the selection of aforementioned proportion keeps the silica gel of absorption glucorphanin to have with silica gel
Ratio can make glucorphanin obtain higher separation.
Step (5) described eluant, eluent includes petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent and acetic acid
Ethyl ester and ethyl alcohol volume ratio 9:1 mixed solvent.The above solvent has different polarity, is eluted by petroleum ether, can be with polarity
Low impurity removes, and using ethyl acetate and petroleum ether mixed solvent, can remove the larger impurity of some polarity, obtain pure
Lower glucorphanin product to be spent, and ethyl acetate is used to be eluted with alcohol mixed solvent, impurity all largely removes, so as to
To obtain the glucorphanin of high-purity.
Step (5) it is described to silicagel column carry out elution include the following steps：First use petroleum ether with the speed of 0.1~6BV/h
Then ethyl acetate and petroleum ether volume ratio 1 are used in elution:1 mixed solvent with 0.1~6BV/h speed elute, finally use
Ethyl acetate and ethyl alcohol volume ratio 9:1 mixed solvent with the speed of 0.1~6BV/h elute, wherein petroleum ether, ethyl acetate
With petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and ethyl alcohol volume ratio 9:The volume of 1 mixed solvent is 2~10 times
Column volume.The eluant, eluent and elution rate with upper volume are used, can effectively be eluted glucorphanin.
Step (5) described drying is freeze-drying, wherein the temperature being freeze-dried is -50 DEG C~-20 DEG C.
The purity of the glucorphanin obtained by this method is more than 95%, and highest yield is 1.2%.
Compared with prior art, beneficial effects of the present invention are embodied in：It is detached using semipolar macroreticular resin and silica gel
Glucorphanin, it is simple for process, it is easy industrialization, macroreticular resin and silica gel are inexpensive, are easy to get, and entire technique is cheap, investment
It is few, and the glucorphanin product (purity is more than 95%) of high-purity can be obtained, highest yield is 1.2%.
Specific implementation mode
It elaborates below to the embodiment of the present invention, the present embodiment is carried out lower based on the technical solution of the present invention
Implement, gives detailed embodiment and specific operating process, but protection scope of the present invention is not limited to following implementation
Example.
Embodiment 1
A method of the extraction separation glucorphanin from broccoli seed, including following steps：
(1) dry broccoli seed 200g is taken, in 105 DEG C of oven 30min, is then crushed, 1000mL is added and contains
Amount is the ethanol solution of 65% (volume fraction), is heated to 60 DEG C of extraction 1h, and filtering obtains glucorphanin solution.Glucorphanin is molten
Liquid is concentrated in Rotary Evaporators, is concentrated into 100mL.
(2) pretreated DM-301 macroporous absorbent resins are filled out into column, glucorphanin concentrate is passed through with 3BV/h speed
Then resin column is washed with the deionized water of 4BV, be then that 95% ethanol solution is eluted with the content of 4BV volumes.
(3) glucorphanin eluent is concentrated in Rotary Evaporators, is concentrated into 20mL, is mixed with 20g silica gel (300 mesh),
Solvent flashing obtains the silica gel of absorption glucorphanin.
(4) 150g silica gel (300 mesh) is taken, is fitted into glass column with petroleum ether wetting, allows silica gel natural subsidence, then logical nitrogen
Silica gel is compacted by gas, releases petroleum ether from glass column lower part, the silica gel for adsorbing glucorphanin is then filled to silicagel column top again.
(5) silicagel column first uses 5BV petroleum ethers to be eluted with the speed of 0.5BV/h, then uses 5BV ethyl acetate and petroleum ether body
Product ratio 1:1 mixed solvent with the speed of 0.5BV/h elute, finally use 8BV ethyl acetate and ethyl alcohol volume ratio 9:1 mixing
Solvent with 0.5BV/h speed elute, collect different eluant, eluents respectively.Respectively by petroleum ether, ethyl acetate and petroleum ether
Volume ratio 1:1 mixed solvent, ethyl acetate and ethyl alcohol volume ratio 9:1 mixed solvent eluent evaporates solvent, and carries out cold
Be lyophilized it is dry, wherein the temperature being freeze-dried be -20 DEG C.
(6) pass through ethyl acetate and ethyl alcohol volume ratio 9 in:The product glucorphanin purity that 1 mixed solvent affords is
96.1%, highest yield is 1.2%.
Embodiment 2
A method of the extraction separation glucorphanin from broccoli seed, including following steps：
(1) dry broccoli seed 200g is taken, in 105 DEG C of oven 30min, is then crushed, 1000mL is added and contains
Amount is 65% ethanol solution, is heated to 60 DEG C of extraction 1h, and filtering obtains glucorphanin solution.Glucorphanin solution is in rotary evaporation
Instrument is concentrated, and 100mL is concentrated into.
(2) pretreated ADS-17 macroporous absorbent resins are filled out into column, glucorphanin concentrate is passed through with 3BV/h speed
Then resin column is washed with the deionized water of 4BV, be then that 95% ethanol solution is eluted with the content of 4BV volumes.
(3) glucorphanin eluent is concentrated in Rotary Evaporators, is concentrated into 20mL, is mixed with 20g silica gel (300 mesh),
Solvent flashing obtains the silica gel of absorption glucorphanin.
(4) 150g silica gel (300 mesh) is taken, is fitted into glass column with petroleum ether wetting, allows silica gel natural subsidence, then logical nitrogen
Silica gel is compacted by gas, releases petroleum ether from glass column lower part, the silica gel for adsorbing glucorphanin is then filled to silicagel column top again.
(5) silicagel column first uses 5BV petroleum ethers to be eluted with the speed of 0.5BV/h, then uses 5BV ethyl acetate and petroleum ether body
Product ratio 1:1 mixed solvent with the speed of 0.5BV/h elute, finally use 8BV ethyl acetate and ethyl alcohol volume ratio 9:1 mixing
Solvent with 0.5BV/h speed elute, collect different eluant, eluents respectively.Respectively by petroleum ether, ethyl acetate and petroleum ether
Volume ratio 1:1 mixed solvent, ethyl acetate and ethyl alcohol volume ratio 9:1 mixed solvent eluent evaporates solvent, and carries out cold
Be lyophilized it is dry, wherein the temperature being freeze-dried be -20 DEG C.
(6) pass through ethyl acetate and ethyl alcohol volume ratio 9 in:The product glucorphanin purity that 1 mixed solvent affords is
95.7%, highest yield is 1.1%.
Embodiment 3
A method of the extraction separation glucorphanin from broccoli seed, including following steps：
(1) it takes the broccoli seed that 200g is dried to be placed in 105 DEG C of oven 20min, 400mL second is added after being crushed
Alcoholic solution is heated to 40 DEG C of extraction 2h, and filtering, filtrate is glucorphanin solution, and by the glucorphanin solution of gained in rotation
Evaporimeter is concentrated, and is concentrated into 1/3 that volume is former glucorphanin liquor capacity, is obtained glucorphanin concentrate；
(2) pretreated ADS-17 macroporous absorbent resins are filled out into column, by glucorphanin concentrate obtained by step (1) with
The speed of 1BV/h is adsorbed by resin column with macroporous absorbent resin, wherein passing through the glucorphanin concentrate of resin column
Volume is 2BV；
(3) macroporous absorbent resin for adsorbing glucorphanin is washed with deionized, then use 2BV volumes, 65% mole it is dense
The ethanol solution of degree is eluted, wherein elution speed be 1BV/h speed by resin column, obtain resin eluent；
(4) resin eluent obtained by step (3) is concentrated into 1/30 that volume is original volume in Rotary Evaporators, be added with
The silica gel of volume of the concentrated liquid numerical value identical weight mixes, and volatilize ethyl alcohol therein, obtains the silica gel of absorption glucorphanin；
(5) use wet method dress post, the silica gel of 200~800 mesh soaked with petroleum ether, is fitted into glass column, allow silica gel oneself
Then so sedimentation leads to nitrogen and is compacted silica gel, releases petroleum ether from glass column lower part, then will adsorb the silica gel of glucorphanin again
It is filled to silicagel column top, wherein petroleum ether and the ratio between silica gel, the volume of silica gel for adsorbing glucorphanin are 10:5:1；
(6) it is first eluted with the speed of 0.1BV/h with the petroleum ether of 2 times of column volumes, then with the ethyl acetate of 2 times of column volumes
With petroleum ether volume ratio 1:1 mixed solvent with 0.1BV/h speed elute, finally use the ethyl acetate of 2 times of column volumes and
Ethyl alcohol volume ratio 9:1 mixed solvent with the speed of 0.1BV/h elute, collect different eluant, eluents respectively, and by eluent
It is concentrated and is freeze-dried, the temperature of freeze-drying is -20 DEG C, obtains glucorphanin product.
After testing, a concentration of the 95.43% of the glucorphanin product kind glucorphanin, highest yield are 1.2%.
Embodiment 4
A method of the extraction separation glucorphanin from broccoli seed, including following steps：
(1) it takes the broccoli seed that 200g is dried to be placed in 105 DEG C of oven 60min, 2000mL is added after being crushed
Ethanol solution, be heated to 70 DEG C extraction 30min, filtering, filtrate is glucorphanin solution, and by the glucorphanin solution of gained in
Rotary Evaporators are concentrated, and are concentrated into 1/10 that volume is former glucorphanin liquor capacity, are obtained glucorphanin concentrate；
(2) pretreated ADS-17 macroporous absorbent resins are filled out into column, by glucorphanin concentrate obtained by step (1) with
The speed of 5BV/h is adsorbed by resin column with macroporous absorbent resin, wherein passing through the glucorphanin concentrate of resin column
Volume is 20BV；
(3) macroporous absorbent resin for adsorbing glucorphanin is washed with deionized, then use 20BV volumes, 95% mole
The ethanol solution of concentration is eluted, wherein elution speed be 5BV/h speed by resin column, obtain resin eluent；
(4) resin eluent obtained by step (3) is concentrated into 1/30 that volume is original volume in Rotary Evaporators, be added with
The silica gel of volume of the concentrated liquid numerical value identical weight mixes, and volatilize ethyl alcohol therein, obtains the silica gel of absorption glucorphanin；
(5) use wet method dress post, the silica gel of 200~800 mesh soaked with petroleum ether, is fitted into glass column, allow silica gel oneself
Then so sedimentation leads to nitrogen and is compacted silica gel, releases petroleum ether from glass column lower part, then will adsorb the silica gel of glucorphanin again
It is filled to silicagel column top, wherein petroleum ether and the ratio between silica gel, the volume of silica gel for adsorbing glucorphanin are 30:10:1；
(6) it is first eluted with the speed of 6BV/h with the petroleum ether of 10 times of column volumes, then with the ethyl acetate of 10 times of column volumes
With petroleum ether volume ratio 1:1 mixed solvent with 6BV/h speed elute, finally with the ethyl acetate and second of 10 times of column volumes
Alcohol volume ratio 9:1 mixed solvent with 6BV/h speed elute, collect different eluant, eluents respectively, and eluent is carried out
The temperature of concentration and freeze-drying, freeze-drying is -50 DEG C, obtains glucorphanin product.
After testing, a concentration of the 96.73% of the glucorphanin product kind glucorphanin, highest yield are 1.2%.
Claims (6)
1. a kind of method of the extraction separation glucorphanin from broccoli seed, which is characterized in that this approach includes the following steps：
(1) glucorphanin solution is extracted from broccoli seed, and the glucorphanin solution of gained is concentrated to give glucorphanin
Concentrate；
(2) glucorphanin concentrate obtained by step (1) is inhaled with semipolar macroporous absorbent resin DM-301 or ADS-17
It is attached；
(3) macroporous absorbent resin is eluted with ethanol solution, obtains resin eluent；
(4) after being concentrated resin eluent obtained by step (3), silica gel mixing is added, volatilize ethyl alcohol, obtains absorption radish sulphur
The silica gel of glycosides, and added to and fill out the silicagel column upper layer obtained by column by silica gel；
(5) silicagel column is eluted with eluant, eluent, collects eluent, and eluent is concentrated, is dried to get radish sulphur
Glycoside product；
Step (3) elution includes the following steps：The macroporous absorbent resin for adsorbing glucorphanin is washed with deionized, so
It being eluted afterwards with the ethanol solution of (2~20) BV volumes, wherein elution speed is 1BV/h~5BV/h speed by resin column,
A concentration of the 65%~95% of the ethanol solution；
Step (5) described eluant, eluent includes petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent and ethyl acetate
With ethyl alcohol volume ratio 9:1 mixed solvent；
Step (5) it is described to silicagel column carry out elution include the following steps：First petroleum ether is used to be eluted with the speed of 0.1~6BV/h,
Then ethyl acetate and petroleum ether volume ratio 1 are used:1 mixed solvent with 0.1~6BV/h speed elute, finally use acetic acid
Ethyl ester and ethyl alcohol volume ratio 9:1 mixed solvent with the speed of 0.1~6BV/h elute, wherein petroleum ether, ethyl acetate and stone
Oily ether volume ratio 1:1 mixed solvent, ethyl acetate and ethyl alcohol volume ratio 9:The volume of 1 mixed solvent is 2~10 times of cylinders
Product；
Step (5) described drying is freeze-drying, wherein the temperature being freeze-dried is -50 DEG C~-20 DEG C.
2. a kind of method of extraction separation glucorphanin from broccoli seed according to claim 1, which is characterized in that
Step (1) the glucorphanin solution that extracted from broccoli seed includes the following steps：Dry broccoli seed is taken to be placed in
100-120 DEG C of oven 20min~60min, ethanol solution is added after being crushed, and is heated to 40~70 DEG C of extraction 30min
~2h, filtering, filtrate is glucorphanin solution, and wherein the mass ratio of broccoli seed and ethyl alcohol is 1:(2~10).
3. a kind of method of extraction separation glucorphanin from broccoli seed according to claim 1, which is characterized in that
Step (1) concentration is that the glucorphanin solution is placed on Rotary Evaporators to be evaporated, until glucorphanin concentrates
The volume ratio of liquid and glucorphanin solution is 1：(3~10).
4. a kind of method of extraction separation glucorphanin from broccoli seed according to claim 1, which is characterized in that
Step (2) is described to be included the following steps with the method that macroporous absorbent resin is adsorbed：Macroporous absorbent resin is filled out into column, is set
Fat column, glucorphanin concentrate with 1~5BV/h speed by resin column, wherein the body of the glucorphanin concentrate by resin column
Product is (2~20) BV.
5. a kind of method of extraction separation glucorphanin from broccoli seed according to claim 1, which is characterized in that
Step (4) concentration is evaporated for the eluent to be placed on Rotary Evaporators, until the eluent that concentration is front and back
Volume ratio be 30：1, silica gel, and the ethyl alcohol therein that volatilizees is added in the eluent after concentration, obtains the silica gel of absorption glucorphanin,
The ratio between quality and the volume of eluent after concentration of the silica gel of addition are 1:1.
6. a kind of method of extraction separation glucorphanin from broccoli seed according to claim 1, which is characterized in that
Step (4) column of filling out uses wet method dress post, includes the following steps：The silica gel of 200~800 mesh is soaked with petroleum ether, is packed into
In glass column, silica gel natural subsidence is allowed, then lead to nitrogen and be compacted silica gel, release petroleum ether from glass column lower part, then again will
The silica gel of absorption glucorphanin is filled to silicagel column top, wherein the ratio between the volume of silica gel of petroleum ether and silica gel, absorption glucorphanin
For (10~30):(5~10):1.
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| 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 |
| CN107501354B (en) * | 2017-08-18 | 2019-11-26 | 赣州华汉生物科技有限公司 | A method of extracting high-purity glucorphanin |
| CN109646590A (en) * | 2018-12-27 | 2019-04-19 | 北京康比特体育科技股份有限公司 | A kind of composition and its application for preventing to move low blood testis |
| CN115969893B (en) * | 2022-12-28 | 2024-01-26 | 河南理工大学 | Extraction method and application of total glucoside of common head cabbage |
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| CN103709211A (en) * | 2013-12-13 | 2014-04-09 | 大兴安岭嘉迪欧营养原料有限公司 | Method for preparing glucoraphanin from broccoli |
| CN104961667A (en) * | 2015-06-16 | 2015-10-07 | 赣州华汉生物科技有限公司 | Purifying method of sulforaphane |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103709211A (en) * | 2013-12-13 | 2014-04-09 | 大兴安岭嘉迪欧营养原料有限公司 | Method for preparing glucoraphanin from broccoli |
| CN104961667A (en) * | 2015-06-16 | 2015-10-07 | 赣州华汉生物科技有限公司 | Purifying method of sulforaphane |
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