CN105713053B - A kind of glucosinolate extraction separation method - Google Patents
A kind of glucosinolate extraction separation method Download PDFInfo
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- CN105713053B CN105713053B CN201610180408.0A CN201610180408A CN105713053B CN 105713053 B CN105713053 B CN 105713053B CN 201610180408 A CN201610180408 A CN 201610180408A CN 105713053 B CN105713053 B CN 105713053B
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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
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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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Abstract
A kind of glucosinolate extraction separation method is related to a kind of extraction separation of active principle, specially a kind of extraction separation method preparing glucosinolate using crucifer seeds as raw material in biological chemical field.This method crushes crucifer seeds, improves the degree of clasmatosis, and glucosinolate is helped to be fully dissolved out.Glucosinolate is extracted using boil water extraction method, recovery rate is up to 96.0% or more.Glucosinolate is purified using activated carbon adsorption elution method, gained glucosinolate product purity can be improved 2.5 3.0 times compared with Aqueous extracts.This method is compared with traditional glucosinolate extraction separation method, glucosinolate extraction efficiency is high, purification effect is good, it is simple for process, environmentally protective, the production and processing of glucosinolate suitable for food-grade and health care grade, it is suitble to large-scale industrial production, there is good promotion prospect.
Description
Technical field
It is specially a kind of to be planted with Cruciferae the present invention relates to a kind of extraction separation of active principle in biological chemical field
Species is the extraction separation method that raw material prepares glucosinolate.
Background technology
The plant of Cruciferae is to be widely believed that a kind of plant with anti-cancer function at present.This is primarily due to cruciate flower
The plant of section contains a large amount of glucosinolate (glucosinolates, abbreviation GLS), and glucosinolate is the one of plant
Kind sulfur-bearing secondary metabolite, at present it has been found that more than 120 kinds of glucosinolate in plant.Glucosinolate is water-soluble
The ionic compound of property, non-volatility, thermal stability.If damaged, thio heteroside glycosylhydrolase, i.e. mustard occur for plant cell
Sub- sulphur thuja acid enzyme (myrosinase, thioglucoside glucohydrolase；EC3.2.3.1 it) is released, and water
Glucosinolate is solved, generates disulfate, glucose and a series of aglucones, these aglucons are by intramolecular
Rearrangement forms isothiocyanates, thiocyanates, nitrile and a small amount of epithio nitrile.Currently, there is many researchs to have shown that isothiocyanic acid
Ester has good anticancer effect and antioxidation, also generates different sulphur cyanogen some researches show that glucosinolate is metabolizable in vivo
Acid esters then plays its anticancer, anti-oxidant and antibacterial action.In recent years, studying more glucosinolate both at home and abroad includes
The glucorphanin in glucose sulforaphane (glucophanin, abbreviation GRA), radish seed in broccoli seed
(glucophenin, abbreviation GRE) etc..Glucosinolate basic structure is as follows：
The extracting method of glucosinolate is mainly hot formulation at present, and the solvent used includes ethyl alcohol, methanol, water and alcohol
Water mixed solution etc. has investigated influence of the factors such as temperature, solid-liquid ratio, time to extraction efficiency；The separation of glucosinolate
Purification process is mainly extraction, acidic alumina method and ion-exchange-resin process etc..It is verified, it is carried using containing alcoholic solvent
It takes, glucosinolate recovery rate is relatively low and cost is higher；It is purified, is introduced using acidic alumina or ion exchange resin
A large amount of salt, desalting process is complicated and the rate of recovery is relatively low.Application No. is 201210166482.9 Chinese invention patent application public affairs
A kind of method that glucosinolate is extracted in the cauline leaf waste from broccoli is opened, this method is by raw material through 75 DEG C of water-bath enzyme deactivations
Afterwards, 75% methanol aqueous solution extraction glucosinolate is used for multiple times, then sulphur glycosides is purified using anion exchange, is gone out
Enzyme is not thorough, and experiment is complicated, and cost is higher.Application No. is the Chinese invention patent applications of 2015104107303.X to disclose one
The method of the extraction of seedling stem sulphur mustard glucosinolate, this method by after the enzyme deactivation of raw material drying, grinding and ether defatting, by
Ultrasonication extracts glucosinolate using methanol aqueous solution, and then uses ethyl acetate removal of impurities and anion exchange
Purifying resin, purification process is extremely complex, and energy consumption is higher, and recovery rate is only 65%-75%, and uses methanol, ether, acetic acid second
The toxic reagents such as ester.
Invention content
It is an object of the invention to establish glucosinolate extraction and purification process method efficient, environmentally friendly, simple for process.
Using crucifer seeds as raw material, clasmatosis is realized by the method for crushing, to improve the molten of glucosinolate
Out-degree；Glucosinolate is extracted using the method for extracting in boiling water, extracting in boiling water can both make the sources Inner myrosin deactivation also can be into
One step promotes clasmatosis, recovery rate to be extracted more compared with alcohol water；It is absorption with Aqueous extracts using 10% ethanol water as eluent
Stoste purifies glucosinolate using activated carbon adsorption elution method, improves glucosinolate product purity to 2.5-3.0
Times, the glucosinolate rate of recovery is up to 85% or more obtained by entire technological process.
The thioglucose glycoside extraction separation technique method that the present invention is established, extraction efficiency is high, purification effect is good, technique
Simply, environmentally protective, it is suitable for the production and processing of the glucosinolate of food-grade and health care grade, before there is good popularization
Scape.
The present invention specific method and steps are as follows：
A method of it is wrapped successively using crucifer seeds as raw material using activated carbon purification glucosinolate
Include following steps：
A. raw material is crushed
Raw material is crushed using pulverizer, collects seed powder；
B. the extraction of glucosinolate
Deionized water heating is measured, after deionized water boiling, according to solid-to-liquid ratio 1:10 ratio is added in (1) and crushes
Raw material afterwards, extracting in boiling water 10min obtain Aqueous extracts using filter cloth suction filtering；Repeat to extract primary, collection glucosinolate water
Extract；
C. the purifying of glucosinolate
According to activated carbon:Glucosinolate mass ratio is 1000:60-80 determines activated carbon dosage, and Aqueous extracts are added
In activated carbon, the activated carbon filter cake for being adsorbed with glucosinolate is obtained by filtration in the stirring and adsorbing 30min under the conditions of 25 DEG C；It presses
According to the activated carbon filter cake for being adsorbed with glucosinolate：10% ethanol water solid-to-liquid ratio is 1:20, it is water-soluble that 10% ethyl alcohol is added
Liquid is adjusted using ammonium hydroxide, measures eluent pH=10 through pH meter, and stirring elution 30min, is obtained by filtration activity under the conditions of 25 DEG C
Charcoal and eluent are continuing with 10% ethanol water and carry out secondary elution to activated carbon, collect eluent twice；10% ethyl alcohol
Aqueous solution is the ethanol water that concentration of volume percent is 10%；
Gained eluent is spin-dried for, is dissolved in water, above-mentioned absorb-elute experiment is repeated；Final gained eluent is steamed through decompression
It evaporates, be freeze-dried.
Further, activated carbon used is craboraffin.
1. the raw material used in step (A) is crucifer seeds, such as broccoli, radish, wild cabbage, cauliflower plant
The seed of object.
2. activated carbon addition refers to the saturated extent of adsorption of activated carbon, activated carbon pair as used in the present invention in step (B)
The saturated extent of adsorption of glucorphanin is 61mg/g, then glucorphanin Aqueous extracts need to be concentrated to 3.0mg/ml or so.
3. activated carbon used in step (C) is wooden 200 mesh craboraffin.
4. the adjusting of eluent pH value and measurement use ammonia spirit and pH meter respectively in step (C).
5. solid-liquid separating equipment is activated carbon filter in step (C).
Specific implementation mode
With reference to specific embodiment, the present invention will be further described, but the purpose of these embodiments and does not lie in limit
Protection scope of the present invention processed.Activated carbon BET specific surface area 1700-1900m employed in following embodiment2/ g, activity
Carbon decoloring rate：180-240mg/g, but not limited to this.
Embodiment 1
Pretreatment of raw material：Certain broccoli seed for being 4.01% by 200gGRA contents (mass percentage content, the same below)
It crushes, obtains 200g broccoli seed powder.
Glucosinolate extracts：It takes 2.3L deionized waters to heat, after boiling, above-mentioned broccoli seed is added thereto
Powder, extracting in boiling water 10min, filter-cloth filtering obtain GRA Aqueous extracts.Repeat to extract primary, collection GRA Aqueous extracts, GRA recovery rates
It is 98.61%.
Glucosinolate purifies：Above-mentioned GRA Aqueous extracts are concentrated into 2.3L, are added in 115g activated carbons, in 25 DEG C of items
Stirring and adsorbing 30min under part.It is separated by solid-liquid separation using activated carbon filter, obtains the activated carbon for being adsorbed with GRA, 2.3L is added
10% ethanol water, it is 10.0 to adjust pH, and 30min is eluted at 25 DEG C, repeats to elute once, collects GRA eluents.It will be upper
It states GRA eluents to be spin-dried for, 2.3L deionized waters is added, as activated carbon adsorption stoste, carried out according to above-mentioned absorb-elute method
Activated carbon is secondarily purified.It is freeze-dried after finally obtained GRA eluents are spin-dried for, obtains GRA product 12.91g, product
GRA purity is 49.81% (stoste GRA purity is 17.14%, and GRA purity is increased to 2.91 times after purification), and the rate of recovery is
81.30%.
Embodiment 2
Pretreatment of raw material：Certain broccoli seed that 100gGRA contents are 6.72% is crushed, 200g broccoli is obtained
Seed powder.
Glucosinolate extracts：It takes 1.9L deionized waters to heat, after boiling, above-mentioned broccoli seed is added thereto
Powder, extracting in boiling water 10min, filter-cloth filtering obtain GRA Aqueous extracts.Repeat to extract primary, collection GRA Aqueous extracts, GRA recovery rates
It is 98.56%.
Glucosinolate purifies：Above-mentioned GRA Aqueous extracts are concentrated into 1.9L, are added in 95g activated carbons, in 25 DEG C of conditions
Lower stirring and adsorbing 30min.It is separated by solid-liquid separation using activated carbon filter, obtains the activated carbon for being adsorbed with GRA, 1.9L is added
10% ethanol water, it is 10.0 to adjust pH, and 30min is eluted at 25 DEG C, repeats to elute once, collects GRA eluents.It will be upper
It states GRA eluents to be spin-dried for, 1.9L deionized waters is added, as activated carbon adsorption stoste, carried out according to above-mentioned absorb-elute method
Activated carbon is secondarily purified.It is freeze-dried after finally obtained GRA eluents are spin-dried for, obtains GRA productions 7.63g, product G RA
Purity is 69.55% (stoste GRA purity is 27.80%, and GRA purity is increased to 2.50 times after purification), and the rate of recovery is
80.09%.
Embodiment 3
Pretreatment of raw material：Certain broccoli seed that 200gGRA contents are 3.47% is crushed, 200g broccoli is obtained
Seed powder.
Glucosinolate extracts：It takes 2.0L deionized waters to heat, after boiling, above-mentioned broccoli seed is added thereto
Powder, extracting in boiling water 10min, filter-cloth filtering obtain GRA Aqueous extracts.Repeat to extract primary, collection GRA Aqueous extracts, GRA recovery rates
It is 96.98%.
Glucosinolate purifies：Above-mentioned GRA Aqueous extracts are concentrated into 2.0L, are added in 100g activated carbons, in 25 DEG C of items
Stirring and adsorbing 30min under part.It is separated by solid-liquid separation using activated carbon filter, obtains the activated carbon for being adsorbed with GRA, 2.0L is added
10% ethanol water, it is 10.0 to adjust pH, and 30min is eluted at 25 DEG C, repeats to elute once, collects GRA eluents.It will be upper
It states GRA eluents to be spin-dried for, 2.0L deionized waters is added, as activated carbon adsorption stoste, carried out according to above-mentioned absorb-elute method
Activated carbon is secondarily purified.It is freeze-dried after finally obtained GRA eluents are spin-dried for, obtains GRA product 12.70g, product
GRA purity is 45.49% (stoste GRA purity is 15.74%, and GRA purity is increased to 2.89 times after purification), and the rate of recovery is
83.11%.
Embodiment 4
Pretreatment of raw material：Certain radish seed that 100gGRE contents are 7.29% is crushed, 200g broccoli kinds are obtained
Sub- powder.
Glucosinolate extracts：It takes 2.4L deionized waters to heat, after boiling, above-mentioned broccoli seed is added thereto
Powder, extracting in boiling water 10min, filter-cloth filtering obtain GRE Aqueous extracts.Repeat to extract primary, collection GRE Aqueous extracts, GRE extractions
Rate is 98.04%.
Glucosinolate purifies：Above-mentioned GRE Aqueous extracts are concentrated into 2.4L, are added in 120g activated carbons, in 25 DEG C of items
Stirring and adsorbing 30min under part.It is separated by solid-liquid separation using activated carbon filter, obtains the activated carbon for being adsorbed with GRE, 2.4L is added
10% ethanol water, it is 10.0 to adjust pH, and 30min is eluted at 25 DEG C, repeats to elute once, collects GRE eluents.It will be upper
It states GRE eluents to be spin-dried for, 2.4L deionized waters is added, as activated carbon adsorption stoste, carried out according to above-mentioned absorb-elute method
Activated carbon is secondarily purified.It is freeze-dried after finally obtained GRE eluents are spin-dried for, obtains GRA product 7.29g, product
GRE purity is 79.77% (stoste GRA purity is 31.04%, and GRE purity is increased to 2.57 times after purification), and the rate of recovery is
81.32%.
Embodiment 5
Pretreatment of raw material：Certain radish seed that 100gGRE contents are 6.13% is crushed, 200g broccoli kinds are obtained
Sub- powder.
Glucosinolate extracts：It takes 2..0L deionized waters to heat, after boiling, above-mentioned broccoli kind is added thereto
Sub- powder, extracting in boiling water 10min, filter-cloth filtering obtain GRE Aqueous extracts.Repeat to extract primary, collection GRE Aqueous extracts, GRE extractions
Rate is 97.68%.
Glucosinolate purifies：Above-mentioned GRE Aqueous extracts are concentrated into 2.0L, are added in 100g activated carbons, in 25 DEG C of items
Stirring and adsorbing 30min under part.It is separated by solid-liquid separation using activated carbon filter, obtains the activated carbon for being adsorbed with GRE, 2.0L is added
10% ethanol water, it is 10.0 to adjust pH, and 30min is eluted at 25 DEG C, repeats to elute once, collects GRE eluents.It will be upper
It states GRE eluents to be spin-dried for, 2.0L deionized waters is added, as activated carbon adsorption stoste, carried out according to above-mentioned absorb-elute method
Activated carbon is secondarily purified.It is freeze-dried after finally obtained GRE eluents are spin-dried for, obtains GRE product 7.79g, product
GRA purity is 62.49% (stoste GRA purity is 23.23%, and GRA purity is increased to 2.69 times after purification), and the rate of recovery is
81.32%.
Claims (3)
1. a kind of method using activated carbon purification glucosinolate includes successively using crucifer seeds as raw material
Following steps：
A. raw material is crushed
Raw material is crushed using pulverizer, collects seed powder；
B. the extraction of glucosinolate
Deionized water heating is measured, after deionized water boiling, according to solid-to-liquid ratio 1:10 ratio is added and is crushed by step A
Raw material afterwards, extracting in boiling water 10min obtain Aqueous extracts using filter cloth suction filtering；Repeat to extract primary, collection glucosinolate water
Extract；
C. the purifying of glucosinolate
According to activated carbon:Glucosinolate mass ratio is 1000:60-80 determines activated carbon dosage, and activity is added in Aqueous extracts
In charcoal, the activated carbon filter cake for being adsorbed with glucosinolate is obtained by filtration in the stirring and adsorbing 30min under the conditions of 25 DEG C；According to suction
Activated carbon filter cake with glucosinolate：10% ethanol water solid-to-liquid ratio is 1:20,10% ethanol water is added, makes
With ammonium hydroxide adjust, through pH meter measure eluent pH=10, under the conditions of 25 DEG C stirring elution 30min, be obtained by filtration activated carbon and
Eluent is continuing with 10% ethanol water and carries out secondary elution to activated carbon, collects eluent twice；10% ethyl alcohol is water-soluble
Liquid is the ethanol water that concentration of volume percent is 10%；
Gained eluent is spin-dried for, is dissolved in water, above-mentioned absorb-elute experiment is repeated；Final gained eluent through vacuum distillation,
Freeze-drying.
2. according to the method described in claim 1, it is characterized in that：The raw material used in step A for broccoli, radish, rocket salad,
Wild cabbage or cauliflower seed.
3. according to the method described in claim 1, it is characterized in that：Activated carbon used is craboraffin.
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| 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 |
| CN110697714A (en) * | 2019-10-17 | 2020-01-17 | 北京化工大学 | Radish-derived nitrogen-doped graded porous carbon and preparation method and application thereof |
| CN110638011A (en) * | 2019-11-05 | 2020-01-03 | 严钦武 | Pickling method of leaf mustard |
| CN111387399B (en) * | 2020-04-07 | 2024-02-23 | 天津市食品研究所有限公司 | Technological method for deodorizing radish juice and radish juice obtained by same |
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