CN107382943B - Method for subcritical water extraction of dihydroquercetin in sorghum bran - Google Patents
Method for subcritical water extraction of dihydroquercetin in sorghum bran Download PDFInfo
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- CN107382943B CN107382943B CN201710605163.6A CN201710605163A CN107382943B CN 107382943 B CN107382943 B CN 107382943B CN 201710605163 A CN201710605163 A CN 201710605163A CN 107382943 B CN107382943 B CN 107382943B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[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
- C07D311/28—Benzo[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
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[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
- C07D311/40—Separation, e.g. from natural material; Purification
Abstract
The invention discloses a method for subcritical water extraction of dihydroquercetin in sorghum bran, and belongs to the technical field of natural product chemistry. The method comprises the steps of subcritical water extraction, suction filtration, reduced pressure concentration, low-temperature standing, centrifugation, separation/enrichment, elution, low-temperature standing of distillate, crystallization, recrystallization and drying of sorghum bran serving as a raw material to obtain a pure dihydroquercetin product. The method can be used for the industrial production of high-purity dihydroquercetin, the sorghum bran raw material is cheap and easy to obtain, the process flow is simple, the operation is simple and convenient, the cost is low, no toxic or harmful reagent is polluted, and the method can be used as a pharmaceutical raw material medicament.
Description
Technical Field
The invention belongs to the technical field of natural product chemistry, and particularly relates to a method for subcritical water extraction of dihydroquercetin in sorghum bran.
Background
Subcritical water is also called super heated water, high-pressure hot water or hot liquid water, and means that water is heated to a high temperature of more than 100 ℃ and below 374 ℃ critical temperature under certain pressure, and a water body is still kept in a liquid state. The hydrogen bond, the ionic hydration, the ionic association, the cluster structure and the like of the microstructure of the fluid in the subcritical state are changed, so that the subcritical water and the water at normal temperature and normal pressure have larger difference in properties. In the subcritical state, the polarity of water can be changed in a wide range along with the increase of temperature, the polarity of water can be gradually changed from strong polarity to non-polarity, the property of the water is more similar to that of an organic solvent, and the solute can be extracted from high to low according to the polarity. The subcritical water extraction technology has become the most remarkable technology in the fields of food, chemical engineering and Chinese herbal medicine development, and is rapidly applied to the preparation of food additives and functional factors and the recycling of food processing wastes.
The DihydroquerCetin is called Taxifolin and Taxifolin, and has chemical name of 3,5,7,3',4' -pentraxin, and English name of DihydroquerCetin, Taxifolin, 3,5,7,3',4' -pentahydroxyflavanone, and molecular formula of C15H12O7And the molecular weight is 304.26. The dihydroquercetin is one of natural flavonoid active ingredients, belongs to vitamin PP family, and has strong oxidation resistance. It can eliminate excessive free radical from human body, promote capillary permeability, improve immunity and reduce cancer; is a good natural medicine for preventing cardiovascular diseases, effectively recovering capillary elasticity, and preventing inflammation and lump formation. At the same time, dihydroquercetin is also a highly effective natural food antioxidant whose antioxidant effect exceeds that of other antioxidants such as quercetin, rutin, and synthetic antioxidants. Dihydroquercetin is widely present in Pinaceae plants, such as maritime pine, Larix gmelinii and Douglas fir, and is a flavonoid compound with the largest content in Larix gmelinii, but the content of dihydroquercetin in the plants is low and is generally only 0.3-5.7%, and the factors make the price of dihydroquercetin expensive, which further hinders the industrial production and application of dihydroquercetin.
Sorghum is one of the main crops in northern and southwest areas of China, is mainly used in wine brewing and feed industries, and is eaten as minor cereals. The sorghum bran accounts for about 12% of the mass of the sorghum grains, contains a large amount of procyanidine, anthocyanin, tannin, phenols, sterol and the like, has high oxidation resistance, and therefore, the sorghum bran also has the effects of resisting and preventing cancers. Earlier researches show that the sorghum bran contains a dihydroquercetin component, but no literature report and patent application for extracting and separating the dihydroquercetin from the sorghum bran exist at present. The invention can further expand the development and utilization of the sorghum bran, provides new resources and a new method for extracting the dihydroquercetin, and can generate good social benefits and considerable economic benefits.
Disclosure of Invention
The invention aims to provide a method for extracting dihydroquercetin from sorghum bran by using a subcritical water extraction technology.
The invention is realized by the following technical scheme:
a method for subcritical water extraction of dihydroquercetin in sorghum bran comprises the following steps:
(1) the sorghum bran is used as a raw material, and is dried, crushed and sieved by a sieve of 20-200 meshes;
(2) placing the raw materials in an extraction kettle, extracting sorghum bran powder by using subcritical water, repeatedly extracting filter residues for three times after suction filtration, combining extracting solutions, and concentrating under reduced pressure to obtain a fluid extract;
(3) subjecting the extract obtained in the step 2 to primary separation by a macroporous adsorption resin chromatographic column, eluting with distilled water to remove unadsorbed water-soluble impurities, eluting with ethanol water solution with a certain volume fraction, and collecting effective fraction liquid;
(4) concentrating the effective fraction liquid under reduced pressure until no alcohol smell exists, and standing at low temperature to separate out a crude crystal product; and recrystallizing the crude product, and drying in vacuum to obtain the pure dihydroquercetin.
In the step (2), the using amount ratio of the sorghum bran to water is 1g: 10-50 mL; the extraction is carried out in subcritical extraction equipment, the extraction temperature is 100-200 ℃, the extraction time is 8-60 min, and the pressure is 4-10 MPa.
In the step (3), the macroporous adsorption resin is nonpolar or medium polar, and the specific models are D101, AB-8, ADS-17 and the like; in the ethanol aqueous solution with a certain volume, the volume fraction of ethanol is 30-95%; the effective fraction liquid is a fraction liquid containing dihydroquercetin detected by HPLC.
In the step (4), the low-temperature condition is 0-4 ℃; the recrystallization comprises the following specific steps: dissolving the crude dihydroquercetin with hot water, vacuum filtering, stirring, cooling, recrystallizing at 0-4 deg.C, and repeatedly crystallizing for three times to obtain dihydroquercetin.
The invention has the beneficial effects that: the method for subcritical water extraction of dihydroquercetin in sorghum bran disclosed by the invention has the advantages that the used extraction solvent and sorghum bran raw materials are low in cost and easy to obtain, the related process flow is simple, the operation is simple and convenient, the related chemical agents are low in cost, can be recycled and reused, and are free of toxic and harmful reagent pollution, industrial production can be carried out, and the method can be used for pharmaceutical raw material medicines.
Drawings
FIG. 1 is an HPLC chart of dihydroquercetin monomer compounds separated from sorghum bran.
Detailed Description
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
Placing 100g of crushed sorghum bran powder which is sieved by a 20-mesh sieve in a subcritical water extraction kettle, adding 1000mL of water, controlling the extraction pressure to be 4MPa, the extraction temperature to be 100 ℃, extracting for 8min, cooling to room temperature after extraction is finished, performing suction filtration, repeatedly extracting filter residues for three times, combining filtrates, and performing vacuum concentration under reduced pressure; loading the concentrated solution onto macroporous resin chromatographic column (AB-8 macroporous adsorbent resin, nonpolar, glass column type of phi 3.0 × L100cm) at flow rate of 3mL/min, and washing the column with 2000mL distilled water at the same flow rate; eluting with 30% ethanol water solution, collecting effective fraction of dihydroquercetin, and detecting with high performance liquid chromatography (see example 3); concentrating the collected effective fraction liquid under reduced pressure until no alcohol smell exists, standing at 0 deg.C, separating out crystal, and filtering to obtain dihydroquercetin crude product; dissolving the crude dihydroquercetin product in hot water, filtering while hot, stirring, cooling, standing the filtrate at 0 deg.C, recrystallizing, and vacuum drying at room temperature to obtain pure dihydroquercetin. Through HPLC detection, the purity of the dihydroquercetin is higher than 97.68%, and the extraction rate is 85.3%.
Example 2
100g of sorghum bran powder which is crushed and sieved by a 200-mesh sieve is taken and placed in a subcritical water extraction kettle, 5000mL of water is added, the extraction pressure is controlled to be 10MPa, the extraction temperature is 200 ℃, the extraction time is 60min, after the extraction is finished, the mixture is cooled to room temperature, and is subjected to suction filtration, the filter residue is repeatedly extracted for three times, the filtrate is combined, and the vacuum concentration is carried out; loading the concentrated solution onto macroporous resin chromatographic column (ADS-17 macroporous adsorbent resin, nonpolar, glass column type of phi 3.0 × L100cm) at flow rate of 3mL/min, and washing the column with 2000mL distilled water at the same flow rate; eluting with 95% ethanol water solution, collecting effective fraction of dihydroquercetin, and detecting with high performance liquid chromatography (see example 3); concentrating the collected effective fraction liquid under reduced pressure until no alcohol smell exists, standing at 4 deg.C, precipitating crystal, and filtering to obtain dihydroquercetin crude product; dissolving the crude dihydroquercetin product in hot water, filtering, stirring, cooling, standing the filtrate at 4 deg.C, recrystallizing, and vacuum drying at room temperature to obtain pure dihydroquercetin. Through HPLC detection, the purity of the dihydroquercetin is higher than 95.44%, and the extraction rate is 91.7%.
Example 3
This embodiment is an embodiment of a method for detecting dihydroquercetin.
The dihydroquercetin is detected by high performance liquid chromatography, and the dihydroquercetin product is separated by an Agilent ZORBAX SB-C18 column (4.6 × 250mm, 5 μm) at detection wavelength of 290nm (mobile phase: A phase is 0.1% acetic acid water solution, B phase is methanol, flow rate is 1mL/min, column temperature is 25 deg.C, gradient elution), and chromatogram is shown in FIG. 1, wherein the dihydroquercetin has chromatographic peak at 25.45min, and under the same chromatographic condition, the retention time of the peak is identical to that of kaempferide control.
Claims (1)
1. A method for subcritical water extraction of dihydroquercetin in sorghum bran is characterized by comprising the following steps:
(1) the sorghum bran is used as a raw material, and is dried, crushed and sieved by a sieve of 20-200 meshes;
(2) placing the raw materials in an extraction kettle, extracting sorghum bran powder by using subcritical water, repeatedly extracting filter residues for three times after suction filtration, combining extracting solutions, and concentrating under reduced pressure to obtain a fluid extract;
(3) subjecting the extract obtained in the step 2 to primary separation by a macroporous adsorption resin chromatographic column, eluting with distilled water to remove unadsorbed water-soluble impurities, eluting with ethanol water solution with a certain volume fraction, and collecting effective fraction liquid;
(4) concentrating the effective fraction liquid under reduced pressure until no alcohol smell exists, and standing at low temperature to separate out a crude crystal product; recrystallizing the crude product, and vacuum drying to obtain pure dihydroquercetin;
in the step (2), the using amount ratio of the sorghum bran to water is 1g: 10-50 mL;
in the step (2), the extraction is carried out in subcritical extraction equipment, the extraction temperature is 100-200 ℃, the extraction time is 8-60 min, and the pressure is 4-10 MPa;
in the step (3), the macroporous adsorption resin is nonpolar or medium polar resin, and the volume fraction of ethanol in the ethanol aqueous solution with a certain volume fraction is 30-95%;
the macroporous adsorption resin is D101, AB-8 and ADS-17;
in the step (4), the low-temperature condition is 0-4 ℃; the recrystallization comprises the following specific steps: dissolving the crude dihydroquercetin with hot water, vacuum filtering, stirring, cooling, recrystallizing at 0-4 deg.C, and repeatedly crystallizing for three times to obtain dihydroquercetin.
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| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993429A (en) * | 2010-12-08 | 2011-03-30 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting dihydroquercetin from larch sawdust |
| 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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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993429A (en) * | 2010-12-08 | 2011-03-30 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting dihydroquercetin from larch sawdust |
| CN104292366A (en) * | 2014-11-06 | 2015-01-21 | 东北林业大学 | Method for simultaneously extracting arabinogalactan and dihydroquercetin from dahurian larch |
Non-Patent Citations (4)
| Title |
|---|
| Application of numerical modeling for optimization of selective hot water extraction of taxifolin from ‘milk thistle’ seeds;Hala El-Adawi等;《African Journal of Biotechnology》;20110829;第10卷(第48期);第9804-9811页 * |
| Effect of acidic condition on phenolic composition and antioxidant potential of aqueous extracts from sorghum (sorghum bicolor) bran;JEREMIAH S. SHELEMBE等;《Journal of Food Biochemistry》;20141231;第38卷;第110-118页 * |
| Subcritical Water Extraction of Biologically Active Substances from Milk Thistle Seed (Silybum murianum L.);I. A. Platonov等;《Russian Journal of Physical Chemistry B》;20101231;第4卷(第8期);第1211-1216页 * |
| Subcritical water extraction of polyphenolic compounds from sorghum (Sorghum bicolor L.) bran and their biological activities;Xiaoping Luo等;《Food Chemistry》;20180422;第262卷;第14-20页 * |
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