CN104961667B - A kind of purification process of sulforaphen - Google Patents
A kind of purification process of sulforaphen Download PDFInfo
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- CN104961667B CN104961667B CN201510334081.3A CN201510334081A CN104961667B CN 104961667 B CN104961667 B CN 104961667B CN 201510334081 A CN201510334081 A CN 201510334081A CN 104961667 B CN104961667 B CN 104961667B
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Abstract
The present invention relates to a kind of purification process of sulforaphen, the method is comprised the following steps：(1) prepare sulforaphen solution；(2) sulforaphen solution is extracted, then extract concentration, obtains sulforaphen concentrated solution；(3) sulforaphen concentrated solution is mixed with kieselguhr, solvent flashing, obtains adsorbing the kieselguhr of sulforaphen；(4) post is filled out with kieselguhr, the kieselguhr of absorption sulforaphen is added to into siliceous earth column upper strata；(5) eluting is carried out with eluant, the eluent of different solvents is collected；(6) eluent concentrated, be drying to obtain absorption sulforaphen product.Compared with prior art, the present invention separates sulforaphen using kieselguhr, simple for process, easily industrialization, kieselguhr is inexpensive, be easy to get, whole technique low price, small investment, and highly purified sulforaphen product can be obtained (purity is more than 95%).
Description
Technical field
The present invention relates to a kind of natural product purification process, more particularly, to a kind of purification process of sulforaphen.
Background technology
Sulforaphen, is glucose radish seed glycoside (one kind of thioglycoside) Jing myrosinase enzymolysis or acid
The isothiocyanate derivatives that hydrolysis is produced, relative molecular mass is 177.29, and molecular formula is C6H11S2NO.Sulforaphen is so far
The most strong class isothiocyanate of the anticancer vigor found in vegetable till the present, be the anti-cancer generally acknowledged at present and anticancer effect most
One of good natural product.The expression of II phase enzyme of I phases enzyme and induction can be suppressed, to hepatocarcinoma, breast carcinoma, pulmonary carcinoma, esophageal carcinoma, front
Row adenocarcinoma, gastric cancer have obvious blocking effect, and sulforaphen also has protection skin, antibacterial, improves antioxidant ability of organism
With the pharmacological action such as immunity, therefore sulforaphen is used as medicine or food function composition, with wide market prospect [food
Fermentation and industry, 2011,37 (7):197-200].
The separation to sulforaphen of China has carried out substantial amounts of research, but high efficiency separation obtains highly purified Radix Raphani sulfur at present
Plain method is few.If patent CN104059947 is after macroporous resin is separated for the first time, just obtained with after preparative hplc post separation again
To highly purified sulforaphen, preparative hplc post separation small scale, it is few that single obtains product volume, is unfavorable for industrialized production；Patent
CN104372045 is extracted by 40-60MPa homogenizing, then with ion liquid abstraction is introduced, obtains highly purified sulforaphen, but
This method is high to equipment requirements, and high pressure easily brings safety problem, and introduces ionic liquid, the table in ionic liquid
Face activating agent is likely to remain in sulforaphen, will bring toxicity to sulforaphen product, so as to affect which to apply.The patent is adopted
After macroporous resin initial gross separation, separated with alumina column chromatography again, but the purity for obtaining sulforaphen product is only more than 90%.
Therefore, a kind of sulforaphen product that high-load is obtained by the process for separation and purification of cheap and simple is found, will be to developing with Radix Raphani
Thionin has for the development of the medicine and health product of main active actively promotes effect.
The content of the invention
The purpose of the present invention is exactly to provide a kind of simple to operate to obtain the sulforaphen product of high-load, environmental protection section
Energy, the purification process of lower-cost sulforaphen.
The purpose of the present invention can be achieved through the following technical solutions：
A kind of purification process of sulforaphen, the method are comprised the following steps：
(1) prepare sulforaphen solution；
(2) sulforaphen solution is extracted, then extract concentration, obtains sulforaphen concentrated solution；
(3) sulforaphen concentrated solution is mixed with kieselguhr, solvent flashing, obtains adsorbing the kieselguhr of sulforaphen；
(4) post is filled out with kieselguhr, the kieselguhr of absorption sulforaphen is added to into siliceous earth column upper strata；
(5) eluting is carried out with eluant, the eluent of different solvents is collected；
(6) eluent concentrated, be drying to obtain absorption sulforaphen product.
The method that sulforaphen solution is prepared in step (1) is：Dry broccoli seed is taken, is crushed, addition is adjusted to pH value
For the ultra-pure water of 2-6, at 5-30 DEG C, digest 6-36h, filter, filtrate be sulforaphen solution, wherein broccoli seed with it is ultrapure
The mass ratio of water is 1:(2～10).
In step (2), the method for prepared sulforaphen concentrated solution is：Dichloromethane is added in sulforaphen solution, is shaken
Extraction is swung, is extracted 3 times, combining extraction liquid, then evaporation solvent, obtains concentrated solution, wherein adding the dichloromethane of extraction every time
Volume ratio with sulforaphen solution, sulforaphen concentrated solution is (5～25):5:1.
Obtain in step (3) adsorb sulforaphen diatomaceous method be：The kieselguhr of 200～800 mesh is added into Radix Raphani
In thionin concentrated solution, stirring, solvent flashing obtain adsorbing the kieselguhr of sulforaphen, wherein kieselguhr and sulforaphen concentrated solution
Volume ratio (2～5):1.
The method that post is filled out with kieselguhr in step (4) is：Using wet method dress post, with petroleum ether by the diatom of 200～800 mesh
Native moistening, loads in glass column, allows kieselguhr natural subsidence, then leads to nitrogen and is compacted kieselguhr, releases from glass column bottom
Then the kieselguhr of absorption sulforaphen be filled to siliceous earth column top, wherein petroleum ether and kieselguhr, absorption Radix Raphani by petroleum ether again
The ratio of the diatomaceous volume of thionin is (10～30):(5～10):1.
In step (5), the condition of eluting is：First with petroleum ether with the speed eluting of 1～6BV/h, then with ethyl acetate with
Petroleum ether volume ratio 1:1 mixed solvent with 1～6BV/h speed eluting, finally with ethyl acetate and methanol volume ratio 9:1
Mixed solvent with 1～6BV/h speed eluting, collect different eluant, wherein petroleum ether, ethyl acetate and stone respectively
Oily ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:The volume of 1 mixed solvent is 2～10 times of cylinders
Product.The Polarity comparision of petroleum ether is low, and eluting is mainly the low fat-soluble impurity of some Polarity comparisions；Volume proportion is 1:1
Ethyl acetate it is bigger than petroleum ether with petroleum ether mixed solvent polarity, can be with the larger impurity of eluting polarity；Through petroleum ether and
After the mixed solvent eluting of petroleum ether and ethyl acetate, impurity is eluted substantially, due to sulforaphen and diatomaceous force ratio
Solvent ability eluting that is larger, polarity can only being adopted larger, after ethyl acetate solvent addition methanol, polarity is further carried
Height, therefore ethyl acetate can effectively by sulforaphen eluting with methanol mixed solvent.
In step (6), respectively by petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate with
Methanol volume ratio 9:1 mixed solvent eluent evaporation solvent, and lyophilization is carried out, wherein cryodesiccated temperature is -50
DEG C～-20 DEG C.
By ethyl acetate and methanol volume ratio 9 in step (6):The product sulforaphen that 1 mixed solvent is afforded is pure
Degree is more than 95%.
Compared with prior art, the present invention separates sulforaphen, simple for process, easy industrialization, silicon using kieselguhr
Diatomaceous earth is inexpensive, be easy to get, whole technique low price, small investment, and (purity is big can to obtain highly purified sulforaphen product
In 95%).
Specific embodiment
With reference to specific embodiment, the present invention is described in detail.
Embodiment 1
(1) broccoli seed of 200g dryings is taken, is crushed, add 1000mL to be adjusted to the ultra-pure water that pH value is 3, enzyme at 15 DEG C
Solution 16h, filters, and filtrate is sulforaphen solution.
(2) 200mL dichloromethane is added in 100mL sulforaphen solution, carries out concussion extraction, extracted 3 times, merged
Extract, then by Rotary Evaporators evaporation solvent, obtains 20mL concentrated solutions.
(3) kieselguhr of 500～600 mesh of 40mL is added in 20mL sulforaphen concentrated solutions, stirring, solvent flashing are obtained
To the kieselguhr of absorption sulforaphen.
(4) wet method dress post is adopted, with 500mL petroleum ether by the kieselguhr moistening of 500～600 mesh of 200mL, loads glass
In post, kieselguhr natural subsidence is allowed, then lead to nitrogen and kieselguhr is compacted, release petroleum ether from glass column bottom, then again will
The kieselguhr of 20mL absorption sulforaphen is filled to siliceous earth column top.
(5) first with 600mL petroleum ether with the speed eluting of 3BV/h, then with 600mL ethyl acetate and petroleum ether (1:1)
Mixed solvent with 3BV/h speed eluting, finally with 600mL ethyl acetate and methanol (9:1) mixed solvent with 3BV/h
Speed eluting, collects different eluant respectively.
(6) respectively by petroleum ether, ethyl acetate and petroleum ether (1:1) mixed solvent, ethyl acetate and methanol (9:1) mix
Eluate solvent is by Rotary Evaporators evaporation solvent, and carries out lyophilization, and cryodesiccated temperature is -50 DEG C～-20 DEG C.
(7) ethyl acetate and methanol (9:1) the product sulforaphen purity that mixed solvent is afforded is 95.9%.
Embodiment 2
A kind of purification process of sulforaphen, the method are comprised the following steps：
(1) prepare sulforaphen solution：Dry broccoli seed is taken, is crushed, added and be adjusted to the ultra-pure water that pH value is 2,5
36h is digested at DEG C, is filtered, filtrate is sulforaphen solution, and wherein broccoli seed and the mass ratio of ultra-pure water are 1:2.
(2) dichloromethane is added in sulforaphen solution, carries out concussion extraction, is extracted 3 times, combining extraction liquid, Ran Houzheng
Solvent is sent out, sulforaphen concentrated solution is obtained, wherein adding the dichloromethane of extraction and sulforaphen solution, sulforaphen to concentrate every time
The volume ratio of liquid is 5:5:1.
(3) kieselguhr of 200～800 mesh is added in sulforaphen concentrated solution, stirring, solvent flashing, obtains adsorbing Radix Raphani
The volume ratio 2 of the kieselguhr of thionin, wherein kieselguhr and sulforaphen concentrated solution:1.
(4) wet method dress post is adopted, with petroleum ether by the kieselguhr moistening of 200～800 mesh, is loaded in glass column, allow diatom
Native natural subsidence, then leads to nitrogen and is compacted kieselguhr, release petroleum ether from glass column bottom, then will adsorb sulforaphen again
Kieselguhr be filled to siliceous earth column top, wherein petroleum ether with the ratio of kieselguhr, the diatomaceous volume of absorption sulforaphen is
10:5:1。
(5) condition for carrying out eluting eluting with eluant is：Then second is used with the speed eluting of 1BV/h with petroleum ether first
Acetoacetic ester and petroleum ether volume ratio 1:1 mixed solvent with 1BV/h speed eluting, finally with ethyl acetate and methanol volume
Than 9:1 mixed solvent with 1BV/h speed eluting, collect different eluant respectively, wherein petroleum ether, ethyl acetate with
Petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:The volume of 1 mixed solvent is 2 times of column volumes,
Collect the eluent of different solvents；
(6) respectively by petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol body
Product compares 9:1 mixed solvent eluent evaporation solvent, and lyophilization is carried out, wherein cryodesiccated temperature is -50 DEG C, obtain final product
Absorption sulforaphen product, by ethyl acetate and methanol volume ratio 9:The product sulforaphen that 1 mixed solvent is afforded is pure
Spend for 95.5%.
Embodiment 3
A kind of purification process of sulforaphen, the method are comprised the following steps：
(1) prepare sulforaphen solution：Dry broccoli seed is taken, is crushed, added and be adjusted to the ultra-pure water that pH value is 6,30
6h is digested at DEG C, is filtered, filtrate is sulforaphen solution, and wherein broccoli seed and the mass ratio of ultra-pure water are 1:10.
(2) dichloromethane is added in sulforaphen solution, carries out concussion extraction, is extracted 3 times, combining extraction liquid, Ran Houzheng
Solvent is sent out, sulforaphen concentrated solution is obtained, wherein adding the dichloromethane of extraction and sulforaphen solution, sulforaphen to concentrate every time
The volume ratio of liquid is 25:5:1.
(3) kieselguhr of 200～800 mesh is added in sulforaphen concentrated solution, stirring, solvent flashing, obtains adsorbing Radix Raphani
The volume ratio 5 of the kieselguhr of thionin, wherein kieselguhr and sulforaphen concentrated solution:1.
(4) wet method dress post is adopted, with petroleum ether by the kieselguhr moistening of 200～800 mesh, is loaded in glass column, allow diatom
Native natural subsidence, then leads to nitrogen and is compacted kieselguhr, release petroleum ether from glass column bottom, then will adsorb sulforaphen again
Kieselguhr be filled to siliceous earth column top, wherein petroleum ether with the ratio of kieselguhr, the diatomaceous volume of absorption sulforaphen is
30:10:1。
(5) condition for carrying out eluting eluting with eluant is：Then second is used with the speed eluting of 6BV/h with petroleum ether first
Acetoacetic ester and petroleum ether volume ratio 1:1 mixed solvent with 6BV/h speed eluting, finally with ethyl acetate and methanol volume
Than 9:1 mixed solvent with 6BV/h speed eluting, collect different eluant respectively, wherein petroleum ether, ethyl acetate with
Petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:The volume of 1 mixed solvent is 10 times of cylinders
Product, collects the eluent of different solvents；
(6) respectively by petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol body
Product compares 9:1 mixed solvent eluent evaporation solvent, and lyophilization is carried out, wherein cryodesiccated temperature is -20 DEG C, obtain final product
Absorption sulforaphen product, by ethyl acetate and methanol volume ratio 9:The product sulforaphen that 1 mixed solvent is afforded is pure
Spend for 96.7%.
Embodiment 4
A kind of purification process of sulforaphen, the method are comprised the following steps：
(1) prepare sulforaphen solution：Dry broccoli seed is taken, is crushed, added and be adjusted to the ultra-pure water that pH value is 4,20
18h is digested at DEG C, is filtered, filtrate is sulforaphen solution, and wherein broccoli seed and the mass ratio of ultra-pure water are 1:6.
(2) dichloromethane is added in sulforaphen solution, carries out concussion extraction, is extracted 3 times, combining extraction liquid, Ran Houzheng
Solvent is sent out, sulforaphen concentrated solution is obtained, wherein adding the dichloromethane of extraction and sulforaphen solution, sulforaphen to concentrate every time
The volume ratio of liquid is 15:5:1.
(3) kieselguhr of 200～800 mesh is added in sulforaphen concentrated solution, stirring, solvent flashing, obtains adsorbing Radix Raphani
The volume ratio 3 of the kieselguhr of thionin, wherein kieselguhr and sulforaphen concentrated solution:1.
(4) wet method dress post is adopted, with petroleum ether by the kieselguhr moistening of 200～800 mesh, is loaded in glass column, allow diatom
Native natural subsidence, then leads to nitrogen and is compacted kieselguhr, release petroleum ether from glass column bottom, then will adsorb sulforaphen again
Kieselguhr be filled to siliceous earth column top, wherein petroleum ether with the ratio of kieselguhr, the diatomaceous volume of absorption sulforaphen is
10:10:1。
(5) condition for carrying out eluting eluting with eluant is：Then second is used with the speed eluting of 3BV/h with petroleum ether first
Acetoacetic ester and petroleum ether volume ratio 1:1 mixed solvent with 3BV/h speed eluting, finally with ethyl acetate and methanol volume
Than 9:1 mixed solvent with 3BV/h speed eluting, collect different eluant respectively, wherein petroleum ether, ethyl acetate with
Petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:The volume of 1 mixed solvent is 6 times of column volumes,
Collect the eluent of different solvents；
(6) respectively by petroleum ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol body
Product compares 9:1 mixed solvent eluent evaporation solvent, and lyophilization is carried out, wherein cryodesiccated temperature is -35 DEG C, obtain final product
Absorption sulforaphen product, by ethyl acetate and methanol volume ratio 9:The product sulforaphen that 1 mixed solvent is afforded is pure
Spend for 97.2%.
The above-mentioned description to embodiment is to be understood that for ease of those skilled in the art and use invention.
Person skilled in the art obviously easily can make various modifications to these embodiments, and described herein general
Principle is applied in other embodiment without through performing creative labour.Therefore, the invention is not restricted to above-described embodiment, ability
Field technique personnel announcement of the invention, the improvement made without departing from scope and modification all should be the present invention's
Within protection domain.
Claims (7)
1. a kind of purification process of sulforaphen, it is characterised in that the method is comprised the following steps：
(1) prepare sulforaphen solution；
(2) sulforaphen solution is extracted using dichloromethane, then extract is concentrated, sulforaphen concentrated solution is obtained；
(3) sulforaphen concentrated solution is mixed with kieselguhr, solvent flashing, obtains adsorbing the kieselguhr of sulforaphen；
(4) post is filled out with kieselguhr, the kieselguhr of absorption sulforaphen is added to into siliceous earth column upper strata；
(5) gradient is carried out with petroleum ether, ethyl acetate and petroleum ether mixed solvent and ethyl acetate and methanol mixed solvent respectively
Eluting, collects the eluent of different solvents；
(6) eluent concentrated, be drying to obtain absorption sulforaphen product；
In step (5), the condition of eluting is：First with petroleum ether with the speed eluting of 1～6BV/h, then with ethyl acetate and oil
Ether volume ratio 1:1 mixed solvent with 1～6BV/h speed eluting, finally with ethyl acetate and methanol volume ratio 9:1 it is mixed
Bonding solvent with 1～6BV/h speed eluting, collect different eluant, wherein petroleum ether, ethyl acetate and petroleum ether respectively
Volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:The volume of 1 mixed solvent is 2～10 times of column volumes.
2. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that Radix Raphani sulfur is prepared in step (1)
The method of plain solution is：Dry broccoli seed is taken, is crushed, addition is adjusted to the ultra-pure water that pH value is 2-6, digests at 5-30 DEG C
6-36h, filters, and filtrate is sulforaphen solution, and wherein broccoli seed and the mass ratio of ultra-pure water are 1:(2～10).
3. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that Radix Raphani sulfur is obtained in step (2)
The method of plain concentrated solution is：Dichloromethane is added in sulforaphen solution, carries out concussion extraction, is extracted 3 times, combining extraction liquid,
Then evaporation solvent, obtains concentrated solution, wherein adding the dichloromethane and sulforaphen solution, sulforaphen concentrated solution of extraction every time
Volume ratio be (5～25):5:1.
4. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that obtain adsorbing trailing plants in step (3)
Foretell thionin diatomaceous method be：The kieselguhr of 200～800 mesh is added in sulforaphen concentrated solution, stirring, solvent flashing,
Obtain adsorbing the kieselguhr of sulforaphen, the wherein volume ratio (2～5) of kieselguhr and sulforaphen concentrated solution:1.
5. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that step is filled out with kieselguhr in (4)
The method of post is：Using wet method dress post, with petroleum ether by the kieselguhr moistening of 200～800 mesh, load in glass column, allow diatom
Native natural subsidence, then leads to nitrogen and is compacted kieselguhr, release petroleum ether from glass column bottom, then will adsorb sulforaphen again
Kieselguhr be filled to siliceous earth column top, wherein petroleum ether with the ratio of kieselguhr, the diatomaceous volume of absorption sulforaphen is
(10～30):(5～10):1.
6. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that in step (6), respectively by stone
Oily ether, ethyl acetate and petroleum ether volume ratio 1:1 mixed solvent, ethyl acetate and methanol volume ratio 9:1 mixed solvent is washed
De- liquid evaporation solvent, and lyophilization is carried out, wherein cryodesiccated temperature is -50 DEG C～-20 DEG C.
7. the purification process of a kind of sulforaphen according to claim 1, it is characterised in that pass through acetic acid second in step (6)
Ester and methanol volume ratio 9:The product sulforaphen purity that 1 mixed solvent is afforded is more than 95%.
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| CN110256391A (en) * | 2018-12-14 | 2019-09-20 | 赣州华汉生物科技有限公司 | A method of extracting the anthocyanidin of the high-purity of separation from black rice |
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| CN101440054B (en) * | 2008-12-02 | 2011-05-11 | 中国林业科学研究院林产化学工业研究所 | Method for preparing phenethyl isosulfocyanate from horseradish |
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