CN107382943A - A kind of method of dihydroquercetin in Subcritical Water Extraction sorghum bran - Google Patents

A kind of method of dihydroquercetin in Subcritical Water Extraction sorghum bran Download PDF

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Publication number
CN107382943A
CN107382943A CN201710605163.6A CN201710605163A CN107382943A CN 107382943 A CN107382943 A CN 107382943A CN 201710605163 A CN201710605163 A CN 201710605163A CN 107382943 A CN107382943 A CN 107382943A
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dihydroquercetin
sorghum bran
extraction
water
subcritical water
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CN201710605163.6A
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CN107382943B (en
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段玉清
罗孝平
张海晖
张迪
蔡梅红
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Jiangsu University
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Jiangsu University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/322,3-Dihydro derivatives, e.g. flavanones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/40Separation, e.g. from natural material; Purification

Abstract

The invention discloses a kind of method of dihydroquercetin in Subcritical Water Extraction sorghum bran, belong to natural product chemistry technical field.This method through Subcritical Water Extraction, filters using sorghum bran as raw material, be concentrated under reduced pressure, stand at low temperature, centrifugation, separation/enrichment, elution, cut liquid stand at low temperature, crystallization and recrystallization, the step of drying, obtain dihydroquercetin sterling.The inventive method can be used for the industrialized production of high-purity dihydroquercetin, and sorghum bran raw material used is cheap to be easy to get, and technological process is simple, easy to operate, and cost is low, without poisonous and harmful reagent contamination, available for pharmaceutical bulk drug.

Description

A kind of method of dihydroquercetin in Subcritical Water Extraction sorghum bran
Technical field
The invention belongs to natural product chemistry technical field, and in particular to dihydro in a kind of Subcritical Water Extraction sorghum bran The method of Quercetin.
Background technology
Subcritical water also known as super heating water, high-pressure water heating or hot liquid water, refer under pressure, heat the water to 100 DEG C still remain in liquid condition with the high temperature below 374 DEG C of upper critical temperature, water body.Fluid is microcosmic under subcritical state The hydrogen bond of structure, ionic hydration, ion association, tufted structure etc. are changed, thus subcritical water with normal temperature and pressure Water has bigger difference in nature.Under subcritical state, with the rise of temperature, the polarity of water can in interior change in a big way, The polarity of water can fade to nonpolar by highly polar, and its property is more closely similar to organic solvent, can by solute by polarity from high to low Extract.Subcritical Water Extraction technology turns into most noticeable technology in food, chemical industry, herbal development field, quilt The rapid recovery renewable resources for applying to food additives, the preparation of function factor and food processing discarded object.
Dihydroquercetin is called texifolin, toxifolin, and its chemistry entitled 3,5,7,3', 4' First Five-Year Plans light base dihydro is yellow Ketone, English name DihydroquerCetin, Taxifolin, 3,5,7,3', 4'-pentahydroxyflavanone, molecular formula For C15H12O7, molecular weight 304.26.Dihydroquercetin is one of natural flavone active component, belongs to nicotinic acid family, With very strong oxidation resistance.It can effectively eliminate excessive free radical from human body, promote the permeability of capillary, Improve immunologic function, reduce the formation of cancer;Be prevent angiocardiopathy, effectively recover capillary elasticity, prevent inflammation and The excellent natural drug that lump is formed.Meanwhile dihydroquercetin or efficient antioxidant from natural food, its antioxygen are turned into With more than other Quercetins, rutin sophorin and synthetized oxidation preventive agent etc..Dihydroquercetin is widely present in pinaceae plant, such as Maritime pine, larch, pesudotsuga taxifolia, and be the flavone compound that content is maximum in larch, but dihydroquercetin is being planted Content is relatively low in thing, and typically only 0.3~5.7%, these factors cause the price of dihydroquercetin costly, and this also enters one Step hinders its industrialized production and application.
Sorghum is one of chief crop of northern China and southwest, is mainly used in wine brewing and feed industry, small part Eaten as coarse cereals.Sorghum bran accounts for the 12% of sorghum seed quality, contains substantial amounts of OPC, anthocyanidin, tannin, phenol Class, sterol etc., have higher oxidation resistance, therefore sorghum bran also has anti-cancer and cancer-preventing effect.Early-stage Study is found, high Contain dihydroquercetin component in fine strain of millet wheat bran, but there has been no the document report of the extraction separation dihydroquercetin from sorghum bran at present Road and patent application.The present invention can further expand the development and utilization of sorghum bran, while also be the extraction of dihydroquercetin New resources and new method are provided, good social benefit and considerable economic benefit can be produced.
The content of the invention
Dihydroquercetin is extracted from sorghum bran using Subcritical Water Extraction technology it is an object of the invention to provide one kind Method.
The present invention is achieved through the following technical solutions:
The method of dihydroquercetin, is carried out as steps described below in a kind of Subcritical Water Extraction sorghum bran:
(1) using sorghum bran as raw material, crushed after being dried crosses 20~200 mesh sieves;
(2) raw material is placed in extraction kettle, sorghum bran powder is extracted with subcritical water, after suction filtration, to filter residue Repeat extraction three times, merge extract solution, be concentrated under reduced pressure into liquid extract;
(3) by macroporous adsorption resin chromatography post carries out initial gross separation on medicinal extract described in step 2, after loading, distilled water is first used Elution removes unadsorbed water-solubility impurity, then is eluted with the ethanol water of certain volume fraction, collects effective cut liquid;
(4) above-mentioned effectively cut liquid is concentrated under reduced pressure into no alcohol taste, be placed under cryogenic conditions, it is separated out the thick production of crystallization Thing;Crude product obtains dihydroquercetin sterling after recrystallizing, being dried in vacuo again.
In step (2), the amount ratio of the sorghum bran and water is 1g:10~50mL;The extraction is in subcritical abstraction Carried out in equipment, extraction temperature is 100~200 DEG C, and extraction time is 8~60min, and pressure is 4~10MPa.
In step (3), the macroporous absorbent resin is nonpolar or middle polarity, concrete model D101, AB-8 and ADS-17 etc.;In the ethanol water of the certain volume, the volume fraction of ethanol is 30~95%;It is described effectively cut liquid be The cut liquid containing dihydroquercetin is detected through HPLC.
In step (4), the cryogenic conditions are 0~4 DEG C;The recrystallization concretely comprises the following steps:Dihydroquercetin is thick Product, with hot water dissolving, filter, stirring cooling, recrystallized under the conditions of being put in 0-4 DEG C, repeated crystallization three times, obtains dihydro while hot Quercetin.
Beneficial effects of the present invention:The method of dihydroquercetin in Subcritical Water Extraction sorghum bran disclosed by the invention, Extractant used and sorghum bran raw material is cheap is easy to get, the technological process being related to is simple, easy to operate, the chemistry being related to Reagent cost is relatively low, recyclable reuse, without poisonous and harmful reagent contamination, industrialized production can be carried out, available for pharmaceutical Bulk drug.
Brief description of the drawings
Fig. 1 is the HPLC figures of the isolated dihydroquercetin monomer compound from sorghum bran.
Embodiment
Experimental method described in following embodiments, it is conventional method unless otherwise specified;The reagent and material, such as Without specified otherwise, commercially obtain.
Embodiment 1
The sorghum bran powder 100g that crushed 20 mesh sieves is taken, is placed in Subcritical Water Extraction kettle, adds 1000mL water, control Extracting pressure 4MPa processed, 100 DEG C, extraction time 8min of extraction temperature, after extraction terminates, room temperature is cooled to, through filtering, filter residue weight It is multiple to extract three times, merging filtrate, vacuum-concentrcted;By concentrate, with macroporous resin chromatography on 3mL/min flow velocitys, (AB-8 is big Macroporous adsorbent resin, nonpolar, glass column model Φ 3.0*L100cm), with same flow velocity, with 2000mL distilled water flushing posts Son;Use volume fraction to be eluted for 30% ethanol water, collect the effective cut liquid of dihydroquercetin, use high performance liquid chromatography Detect (method is shown in embodiment 3);By effective cut liquid of collection through being concentrated under reduced pressure into no alcohol taste, stood at 0 DEG C, separate out crystallization After filter, obtain dihydroquercetin crude product;By dihydroquercetin crude product, with hot water dissolving, filter while hot, stirring cooling, by this Filtrate stands under conditions of 0 DEG C, through recrystallization, after room temperature in vacuo is dried, obtains dihydroquercetin sterling.Detected through HPLC, two Hydrogen Quercetin purity is higher than 97.68%, recovery rate 85.3%.
Embodiment 2
The sorghum bran powder 100g that crushed 200 mesh sieves is taken, is placed in Subcritical Water Extraction kettle, adds 5000mL water, Extracting pressure 10MPa is controlled, 200 DEG C, extraction time 60min of extraction temperature, after extraction terminates, is cooled to room temperature, through filtering, filter Slag repeats extraction three times, merging filtrate, vacuum-concentrcted;By concentrate with macroporous resin chromatography on 3mL/min flow velocitys (ADS-17 macroporous absorbent resins, nonpolar, glass column model Φ 3.0*L100cm), with same flow velocity, is steamed with 2000mL Distilled water rinses pillar;Use volume fraction to be eluted for 95% ethanol water, the effective cut liquid of dihydroquercetin is collected, with height Effect liquid phase chromatogram detects (method is shown in embodiment 3);It is quiet at 4 DEG C by effective cut liquid of collection through being concentrated under reduced pressure into no alcohol taste Put, separate out crystallization and filtration, obtain dihydroquercetin crude product;By dihydroquercetin crude product, with hot water dissolving, filter, stir while hot Cooling is mixed, the filtrate is stood under conditions of 4 DEG C, through recrystallization, after room temperature in vacuo is dried, obtains dihydroquercetin sterling.Through HPLC is detected, and dihydroquercetin purity is higher than 95.44%, and recovery rate is recovery rate 91.7%.
Embodiment 3
The present embodiment is the embodiment of dihydroquercetin detection method.
Dihydroquercetin is detected by high performance liquid chromatography, and dihydroquercetin product is 290nm in Detection wavelength, through peace Prompt human relations ZORBAX SB-C18 posts (4.6 × 250mm, 5 μm) separate (mobile phase:A phases are 0.1% acetic acid aqueous solution, and B phases are first Alcohol;Flow velocity is 1mL/min, and column temperature is 25 DEG C, gradient elution), chromatogram as shown in figure 1, dihydroquercetin at 25.45min There is chromatographic peak, under same chromatographic condition, the retention time at the peak is consistent with the retention time of Kaempferitrin reference substance.

Claims (6)

1. a kind of method of dihydroquercetin in Subcritical Water Extraction sorghum bran, it is characterised in that carry out as steps described below:
(1)Using sorghum bran as raw material, crushed after being dried crosses 20 ~ 200 mesh sieves;
(2)Raw material is placed in extraction kettle, and sorghum bran powder is extracted with subcritical water, and after suction filtration, filter residue is repeated Extraction three times, merges extract solution, is concentrated under reduced pressure into liquid extract;
(3)By macroporous adsorption resin chromatography post carries out initial gross separation on medicinal extract described in step 2, after loading, first with distillation water elution Unadsorbed water-solubility impurity is removed, then is eluted with the ethanol water of certain volume fraction, collects effective cut liquid;
(4)Above-mentioned effectively cut liquid is concentrated under reduced pressure into no alcohol taste, is placed under cryogenic conditions, it is separated out crystallization crude product;Slightly Product obtains dihydroquercetin sterling after recrystallizing, being dried in vacuo again.
2. the method for dihydroquercetin, its feature exist in a kind of Subcritical Water Extraction sorghum bran according to claim 1 In step(2)In, the amount ratio of the sorghum bran and water is 1g:10~50mL.
3. the method for dihydroquercetin, its feature exist in a kind of Subcritical Water Extraction sorghum bran according to claim 1 In step(2)In, the extraction is carried out in subcritical abstraction equipment, extraction temperature be 100 ~ 200 DEG C, extraction time be 8 ~ 60min, pressure are 4 ~ 10MPa.
4. the method for dihydroquercetin, its feature exist in a kind of Subcritical Water Extraction sorghum bran according to claim 1 In step(3)In, the macroporous absorbent resin is nonpolar or middle polarity resin, the ethanol water of the certain volume In, the volume fraction of ethanol is 30 ~ 95%.
5. the method for dihydroquercetin, its feature exist in a kind of Subcritical Water Extraction sorghum bran according to claim 4 In the macroporous absorbent resin be D101, AB-8 and ADS-17.
6. the method for dihydroquercetin, its feature exist in a kind of Subcritical Water Extraction sorghum bran according to claim 4 In step(4)In, the cryogenic conditions are 0 ~ 4 DEG C;The recrystallization concretely comprises the following steps:By dihydroquercetin crude product, use Hot water dissolving, filter, stirring cooling, recrystallized under the conditions of being put in 0-4 DEG C, repeated crystallization three times, obtains dihydroquercetin while hot.
CN201710605163.6A 2017-07-24 2017-07-24 Method for subcritical water extraction of dihydroquercetin in sorghum bran Active CN107382943B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108815401A (en) * 2018-06-22 2018-11-16 江苏大学 A kind of method of total polyphenols in Subcritical Water Extraction sorghum bran
CN108929201A (en) * 2018-08-20 2018-12-04 凤阳县小岗村永和营养保健品有限公司 A kind of method that Subcritical Water Extraction technology extracts cannabidiol

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CN104292366A (en) * 2014-11-06 2015-01-21 东北林业大学 Method for simultaneously extracting arabinogalactan and dihydroquercetin from dahurian larch

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108815401A (en) * 2018-06-22 2018-11-16 江苏大学 A kind of method of total polyphenols in Subcritical Water Extraction sorghum bran
CN108929201A (en) * 2018-08-20 2018-12-04 凤阳县小岗村永和营养保健品有限公司 A kind of method that Subcritical Water Extraction technology extracts cannabidiol

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