CN110002962A - The extracting method of alkyl-resorcin in a kind of wheat bran - Google Patents
The extracting method of alkyl-resorcin in a kind of wheat bran Download PDFInfo
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- CN110002962A CN110002962A CN201910401667.5A CN201910401667A CN110002962A CN 110002962 A CN110002962 A CN 110002962A CN 201910401667 A CN201910401667 A CN 201910401667A CN 110002962 A CN110002962 A CN 110002962A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/80—Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
- Y02P60/87—Re-use of by-products of food processing for fodder production
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Abstract
The invention belongs to natural function substances to separate preparation field, be related to a kind of extracting method of alkyl-resorcin in wheat bran.The present invention selects drying wheat wheat bran for raw material, after raw material are selected arrangement milling, ethyl acetate is added and carries out ultrasonic extraction, supernatant is obtained after centrifugation, obtains concentrate through rotary evaporation.Silica gel column chromatography is carried out followed by Solid Phase Extraction or silica gel mixed sample to be isolated and purified, eluent is regathered and is further concentrated, and both obtains alkyl-resorcin difference homologue mixed liquor.Through efficient liquid phase chromatographic analysis, it is known that different homologues have many advantages, such as that separating degree is good, with high purity in alkyl-resorcin product.Compared with existing alkyl-resorcin technology of preparing, alkyl-resorcin naturally occurring in wheat bran is isolated and purified using silica gel column chromatography, greatly reduces chemically synthesized complexity and risk, and strong operability.
Description
Technical field
The present invention relates to a kind of extracting methods of alkyl-resorcin in wheat bran, and it is pure to belong to the separation of natural function substance
Change field.
Background technique
Alkyl-resorcin (Alkylresorcinols, ARs) it is 1,3- resorcinol, phenyl ring 5 contain odd number
The general name of an alkyl-substituted analog derivative for carbon atom, belongs to phenols lipoid, has amphiphilic.ARs is distributed in wheat seed
Cortex, is main phenols component in wheat, and total content range is 320 ~ 1010 μ g/g.ARs is made of a variety of homologues,
Its alkyl side chain contains odd number carbon atom (13 ~ 27), is named as C13:0 ~ C27:0, main component be C19:0 and
C21:0.ARs is the important biomolecule marker that existing Grain Trade standard (LS/T 3244-2015) judges wholemeal, and complete
One of important component of flour.Research shows that ARs has certain functional characteristic, such as anticancer, anti-oxidant, inhibition enzyme activity and promotion
Wound healing etc. has some improvement to a variety of chronic diseases.Therefore, ARs is increasingly subject to the concern and attention of people.
China is the big country of world wheat plantation and consumption.Large by-product of the wheat bran as wheat flour milling, accounts for about
The 15% of wheat seed quality, annual output are up to 30,000,000 tons.Wheat bran since its crude fiber content is abundant, mouthfeel is rough,
In 85% or more be used for feed and fermentation industry, rarely wheat bran class health food lists, and economic value is lower.But in wheat bran
It is also natural containing a large amount of activity containing more rich dietary fiber, protein, carbohydrate, vitamin and mineral etc.
Antioxidant, such as: alkyl-resorcin, ferulic acid, phenolic acid etc. are the by-products of great nutritive value.Wheat bran source
It is sufficient and cheap, therefore increase and its comprehensive utilization is improved by wheat bran higher value application to the research dynamics of wheat bran
Rate is of great significance.
In research in recent years, biomarker of the ARs as the full cereal of wheat, but in the full cereal wheat research in China
In be still in the junior stage, the extracting method and product technology of preparing about cereal ARs are also rarely reported.The research of ARs exists
Following problems: first, lack the alkyl-resorcin isolation technics of reasonable standard, such as ARs homologue heptadecyl isophthalic two
Two-CH are differed only by between phenol and nonadecyl resorcinol2, the close and difficult separation of polarity；Second, alkyl-resorcin mark
Quasi- product are expensive and delivery date is long, easily influence the research progress of alkyl-resorcin；Third, forefathers research in have chemical synthesis
Alkyl-resorcin precedent, but synthesis process is complicated, difficult to control, risk is big, and the later period needs further purification, has to environment
The risk of secondary pollution.In view of the above problems, establish the preparation methods of wheat bran alkyl-resorcin standard items a kind of for
It further studies alkyl-resorcin and application is of great significance.
Summary of the invention
The object of the present invention is to provide the extracting method and product of a kind of wheat bran alkyl-resorcin, obtain between alkyl
The sterling of benzenediol difference homologue can be used for detection, trophic function activity and application of alkyl-resorcin etc..
A kind of extracting method of wheat bran alkyl-resorcin of the present invention, to analyze pure ethyl acetate solution as extraction
Solvent carries out ultrasonic extraction to wheat bran；Gained extracting solution is concentrated using Rotary Evaporators, then passes through the silicon of optimization
Plastic column chromatography preparation method obtains 7 kinds of alkyl-resorcin homologue mixtures, respectively heptadecyl resorcinol, 19 alkene
Base resorcinol, nonadecyl resorcinol, two hendecene base resorcinols, heneicosyl resorcinol, tricosyl
Resorcinol and pentacosyl resorcinol；Finally seven kinds of alkyl-resorcin homologues are carried out using high performance liquid chromatography
Measurement.It is realized particular by following technical scheme:
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, obtains alkyl
Resorcinol ethyl acetate extract concentrate；
(5) isolate and purify: first method is that silica white is placed in 120 DEG C of baking oven high temperature activation 30 using silica gel column chromatography
Min, then be placed in drier and be cooled to room temperature.The concentrate sample and silica white mass ratio weighed in step (4) is 1:1,
Entering and carry out mixing sample in evaporating dish, is then placed in 50 DEG C of baking oven drying, taking-up, which is cooled to room temperature, to be stirred for uniformly, and it is spare, to silicon
Plastic column chromatography carries out dry method loading, selects eluent to rush column elution and is isolated and purified；Second method is using Solid Phase Extraction
The concentrate loading of step (4) to solid-phase extraction column is rushed column elution by eluent and is isolated and purified by column.
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent obtained by (5), draw elution concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
Preferably, purification condition described in step (5) are as follows: use silica gel column chromatography, mix sample quality and silica gel column layer
Silica white mass ratio is 1:10 in analysis.The eluent is petroleum ether-ethyl acetate (v/v, 10:1 ~ 1:1).
Step (7) described liquid phase chromatogram condition are as follows:
(1) mobile phase: 0.1% aqueous formic acid of A phase；0.1% formic acid methanol solution of B phase, flow velocity: 1 mL/min, column temperature: 30 DEG C,
Sample volume: 10 μ L；
(2) mobile phase elution program are as follows: 0min, A phase 15 ~ 25%, B phase 75 ~ 85%；5min, A phase 15 ~ 10%, B phase 75 ~ 90%；
10min, A phase 5 ~ 10%, B phase 90 ~ 95%；15min, A phase 0 ~ 5%, B phase 95 ~ 100%；35min, A phase 15 ~ 25%, B phase 75 ~ 85%；
(3) detector: using DAD detector, and Detection wavelength is 280 nm.
It is obtained through efficient liquid phase chromatographic analysis, the present invention extracts 7 kinds of alkyl-resorcin homologue mixtures, respectively
Heptadecyl resorcinol, 19 alkenyl resorcinols, nonadecyl resorcinol, two hendecene base resorcinols, 21
Alkyl-resorcin, tricosyl resorcinol and pentacosyl resorcinol.
The alkyl-resorcin homologue mixture that said extracted obtains further is passed through into half preparation solution phase processor, is separated
Five kinds of alkyl-resorcin monomers out, respectively heptadecyl resorcinol, nonadecyl resorcinol, heneicosyl isophthalic
Diphenol, tricosyl resorcinol, pentacosyl resorcinol.
The semi-preparative liquid chromatography condition are as follows:
(1) mobile phase: 0.1% aqueous formic acid of A phase；0.1% formic acid methanol solution of B phase, flow velocity: 2 mL/min, column temperature: 30 DEG C,
Sample volume: 200 μ L；
(2) mobile phase elution program are as follows: 0min, A phase 15 ~ 25%, B phase 75 ~ 85%；5min, A phase 15 ~ 10%, B phase 75 ~ 90%；
10min, A phase 5 ~ 10%, B phase 90 ~ 95%；15min, A phase 0 ~ 5%, B phase 95 ~ 100%；35min, A phase 15 ~ 25%, B phase 75 ~ 85%；
(3) detector: using DAD detector, and Detection wavelength is 280 nm.
It is that the present invention has the utility model has the advantages that
(1) seven kinds of alkyl-resorcin homologue mixtures that the method for the present invention is extracted, then be prepared by half preparation liquid phase
To five kinds of alkyl-resorcin monomers, wheat bran is made to be fully used.
(2) the method for the present invention selects customization glass column, silica white to fill out column construction silica gel column chromatography, and silica white compares other columns
Filler is cheap, utilization rate is high.
(3) the method for the present invention selects petroleum ether-ethyl acetate mixed solution as eluent, mixed compared to chloroform-ether
It is smaller and environmentally friendly to close its toxicity of solution.
Detailed description of the invention
Fig. 1 is the liquid chromatogram of alkyl-resorcin ethyl acetate extract concentrate in embodiment 1；
Fig. 2 is the liquid chromatogram of 1 product of embodiment；
Fig. 3 is the liquid chromatogram of 1 product of comparative example；
Fig. 4 is the liquid chromatogram of 2 product of embodiment；
Fig. 5 is the liquid chromatogram of 2 product of comparative example；
Fig. 6 is the chromatogram for partly preparing liquid product of embodiment 3.
In figure: 1- heptadecyl resorcinol, 19 alkenyl resorcinol of 2-, 3- nonadecyl resorcinol, 4- 20
One alkenyl resorcinol, 5- heneicosyl resorcinol, 6- tricosyl resorcinol, 7- pentacosyl isophthalic two
Phenol.
Specific embodiment
Below by way of specific embodiment, the invention will be further described.
Embodiment 1
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, obtains alkyl
Resorcinol ethyl acetate extract concentrate；
(5) it isolates and purifies: using silica gel column chromatography, 100 ~ 200 mesh silica whites being placed in 120 DEG C of baking oven high temperature activation first
30 min, then be placed in drier and be cooled to room temperature.The concentrate sample and silica white for weighing homogenous quantities pour into evaporating dish simultaneously
It stirs evenly, is placed in 50 ~ 60 DEG C of oven overnight drying, takes out, be cooled to room temperature spare.Select 500*40 mm normal pressure glass
Chromatographic column uses a dry method on a sample.Silica white after activation is poured into the chromatographic column of clean dried, shakes gently chromatographic column to filling out
Expect surfacing, dress pillar height degree is 18 cm.Chromatographic column is fixed on iron stand, erects and places to filler plane no longer to sink,
It is gently added and mixes sample silica gel to surfacing.Vacant certain altitude is answered in chromatographic column upper end, so as to eluent accumulation.Select petroleum
Ether-ethyl acetate (v/v, 10:1) carries out gradient elution, and every 100 mL eluent is rotated, tracked using TLC, merges
Same composition is analyzed using HPLC and collects eluent；
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent, draw elution concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
After measured, the alkyl-resorcin congener content obtained under the above conditions is 95.20 ~ 97.81 mg/g,
Mixture including 7 kinds of homologues, respectively heptadecyl resorcinol, 19 alkenyl resorcinols, nonadecyl isophthalic two
Phenol, two hendecene base resorcinols, heneicosyl resorcinol, tricosyl resorcinol and pentacosyl isophthalic two
Phenol.It is significantly improved compared with 39.88 ~ 42.17 mg/g of alkyl-resorcin content in the concentrate after step (4) in attached drawing 1.
Comparative example 1
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, obtains alkyl
Resorcinol ethyl acetate extract concentrate；
(5) it isolates and purifies: using processing method same as Example 1, difference is to select chloroform-ether eluent system
(v/v, 9:1) carries out gradient elution, and every 100 mL eluent is rotated, tracked using TLC, merges same composition, makes
It is analyzed with HPLC and collects eluent；
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent, draw elution concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
The alkyl-resorcin congener content obtained under the above conditions is 69.28 ~ 73.65 mg/g, lower than implementation
The content of alkyl-resorcin in example 1.
Embodiment 2
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10 min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, obtains alkyl
Resorcinol ethyl acetate extract concentrate；
(5) it isolates and purifies: selecting solid-phase extraction column, rush column removing impurity using pentane first and reduce Solid Phase Extraction column polarity
Afterwards, by alkyl-resorcin ethyl acetate extract concentrate loading to solid-phase extraction column, by automatic injector with 0.5 mL/
The flow velocity of min is eluted.Select petroleum ether-ethyl acetate (v/v, 1:1) carry out gradient elution, every 100 mL eluent into
Row revolving, is tracked using TLC, is merged same composition, is analyzed using HPLC and collect eluent；
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent, draw elution concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
The alkyl-resorcin content obtained under the above conditions is 76.43 ~ 80.26 mg/g, compared with alkyl in attached drawing 1
39.88 ~ 42.17 mg/g of alkyl-resorcin content is significantly improved in resorcinol crude extract.
Comparative example 2
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, obtains alkyl
Isophthalic ethyl acetate extract concentrate；
(5) it isolates and purifies: selecting solid-phase extraction column, rush column removing impurity using pentane first and reduce Solid Phase Extraction column polarity
Afterwards, by alkyl-resorcin ethyl acetate extract concentrate loading to solid-phase extraction column, by automatic injector with 0.5 mL/
The flow velocity of min is eluted.Chloroform-ether eluent system (v/v, 9:1) is selected to carry out gradient elution, every 100 mL eluent
It is rotated, is tracked using TLC, merged same composition, analyzed using HPLC and collect eluent；
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent, draw certain volume and elute concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
The alkyl-resorcin congener content obtained under the above conditions is 53.93 ~ 56.83 mg/g, lower than implementation
The content of alkyl-resorcin in example 2.
Embodiment 3
Compare each alkyl-resorcin and isolate and purify effect, 1 gained mixture separating degree of embodiment is good, and impurity is few.Using implementation
1 gained alkyl-resorcin homologue mixture of example further prepares alkyl-resorcin monomer by half preparation liquid phase.
Semi-preparative liquid chromatography condition are as follows:
(1) mobile phase: 0.1% aqueous formic acid of A phase；0.1% formic acid methanol solution of B phase, flow velocity: 2 mL/min, column temperature: 30 DEG C,
Sample volume: 200 μ L；
(2) mobile phase elution program are as follows: 0min, A phase 15 ~ 25%, B phase 75 ~ 85%；5min, A phase 15 ~ 10%, B phase 75 ~ 90%；
10min, A phase 5 ~ 10%, B phase 90 ~ 95%；15min, A phase 0 ~ 5%, B phase 95 ~ 100%；35min, A phase 15 ~ 25%, B phase 75 ~ 85%；
(3) detector: using DAD detector, and Detection wavelength is 280 nm.
5 monomers of alkyl-resorcin, respectively heptadecyl resorcinol, nonadecane are obtained under the above conditions
Base resorcinol, heneicosyl resorcinol, tricosyl resorcinol, pentacosyl resorcinol.
Claims (6)
1. the extracting method of alkyl-resorcin in a kind of wheat bran, which is characterized in that specific step is as follows:
(1) it pretreatment of raw material: is dried being cleaned after the wheat removal rubble, silt and disease pest grain of current year harvest, obtains wheat bran
Wheat bran is milled to 80 mesh using flour mill afterwards；
(2) it extracts: ethyl acetate being selected to carry out ultrasonic extraction to wheat bran as Extraction solvent, extraction time is 30 min,
Extraction power is 300 W；
(3) it is centrifuged: being centrifuged 10 min with 3500 r/min, obtain sample supernatant；
(4) it is concentrated: collecting centrifugation gained supernatant, be concentrated using Rotary Evaporators, temperature condition is 45 DEG C, is obtained between alkyl
Benzenediol ethyl acetate extract concentrate；
(5) isolate and purify: first method is that silica white is placed in 120 DEG C of baking oven high temperature activation using silica gel column chromatography
30 min, then be placed in drier and be cooled to room temperature；The concentrate sample and silica white mass ratio weighed in step (4) is 1:1,
It pours into and carries out mixing sample in evaporating dish, be then placed in 50 ~ 60 DEG C of baking oven drying, taking-up, which is cooled to room temperature, to be stirred for uniformly, standby
With to silica gel column chromatography progress dry method loading, selection eluent rushes column elution and isolated and purified；Second method is using solid
The concentrate loading of step (4) to solid-phase extraction column is rushed column elution by eluent and is isolated and purified by phase extraction column；
(6) it is concentrated again: collecting concentrated by rotary evaporation after eluent obtained by (5), draw elution concentrate；
(7) it efficient liquid phase chromatographic analysis: with the redissolution of 1 mL methanol solution after nitrogen is blown, crosses after 0.22 μm of organic filter membrane for efficient
Liquid chromatographic detection.
2. extracting method according to claim 1, which is characterized in that the silicagel column used in step (5), mix sample quality with
Silica white mass ratio is 1:10 in silica gel column chromatography.
3. extracting method according to claim 1, which is characterized in that the eluent be petroleum ether-ethyl acetate (v/v,
10:1 ~ 1:1).
4. the alkyl-resorcin homologue mixture extracted using any one of claim 1-3 the method, feature
Be, including 7 kinds of homologues, respectively heptadecyl resorcinol, 19 alkenyl resorcinols, nonadecyl resorcinol,
Two hendecene base resorcinols, heneicosyl resorcinol, tricosyl resorcinol and pentacosyl resorcinol.
5. alkyl-resorcin homologue mixture according to claim 4, which is characterized in that alkyl-resorcin content
Up to 95.20 ~ 97.81 mg/g, purity is up to 95% or more.
6. the alkyl-resorcin homologue mixture that any one of -3 the methods are extracted according to claim 1, feature
It is, step (8), using half preparation solution phase processor, chromatographic condition are as follows:
(1) mobile phase: 0.1% aqueous formic acid of A phase；0.1% formic acid methanol solution of B phase, flow velocity: 2 mL/min, column temperature: 30 DEG C,
Sample volume: 200 μ L；
(2) mobile phase elution program are as follows: 0min, A phase 15 ~ 25%, B phase 75 ~ 85%；5min, A phase 15 ~ 10%, B phase 75 ~ 90%；
10min, A phase 5 ~ 10%, B phase 90 ~ 95%；15min, A phase 0 ~ 5%, B phase 95 ~ 100%；35min, A phase 15 ~ 25%, B phase 75 ~ 85%；
(3) detector: using DAD detector, and Detection wavelength is 280 nm；
Isolate five kinds of alkyl-resorcin monomers, respectively heptadecyl resorcinol, nonadecyl resorcinol, 21
Alkyl-resorcin, tricosyl resorcinol, pentacosyl resorcinol.
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| CN115557830A (en) * | 2022-10-26 | 2023-01-03 | 江南大学 | Method for extracting alkylresorcinol from wheat bran based on ultrasonic-assisted enzymolysis method |
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| CN115557830A (en) * | 2022-10-26 | 2023-01-03 | 江南大学 | Method for extracting alkylresorcinol from wheat bran based on ultrasonic-assisted enzymolysis method |
| CN115557830B (en) * | 2022-10-26 | 2024-02-13 | 江南大学 | Method for extracting alkyl resorcinol from wheat bran based on ultrasonic-assisted enzymolysis |
| WO2024087314A1 (en) * | 2022-10-26 | 2024-05-02 | 江南大学 | Method for extracting alkylresorcinols in wheat bran based on ultrasound-assisted enzymolysis method |
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