CN111039911B - Method for extracting soybean isoflavone from soybean germ - Google Patents
Method for extracting soybean isoflavone from soybean germ Download PDFInfo
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- CN111039911B CN111039911B CN201911265124.1A CN201911265124A CN111039911B CN 111039911 B CN111039911 B CN 111039911B CN 201911265124 A CN201911265124 A CN 201911265124A CN 111039911 B CN111039911 B CN 111039911B
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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
- C07D311/34—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 3 only
- C07D311/36—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 3 only not hydrogenated in the hetero ring, e.g. isoflavones
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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
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Abstract
The invention provides a method for extracting soybean isoflavone from soybean germs, which belongs to the technical field of extraction of functional active substances of food, and comprises the following steps: 1) Micronizing soybean germs to obtain soybean germ powder; 2) Mixing the soybean germ powder with water, and emulsifying to obtain soybean germ emulsion; 3) Mixing the soybean germ emulsion with a solvent, and performing jet cavitation to obtain a solvent extracting solution; 4) And mixing and homogenizing the solvent extracting solution, ethyl acetate, n-butanol and water, and performing high-efficiency countercurrent chromatography to separate the soybean isoflavone. The method provided by the invention has the advantages that the extraction rate of the soybean isoflavone is remarkably increased and can reach 2.1-2.3%; the purity is as high as 95.59% -98.32%.
Description
Technical Field
The invention belongs to the technical field of extraction of functional active substances of foods, and particularly relates to a method for extracting soybean isoflavone from soybean germs.
Background
The soybean isoflavone is a plant estrogen, has a molecular structure similar to that of estrogen, and can bidirectionally regulate estrogen level in female body. The research shows that the soybean isoflavone has more remarkable effects on improving female menopause, osteoporosis, cardiovascular diseases, beauty treatment and the like. Isoflavone is one of flavonoids, mainly existing in leguminous plants, and is a secondary metabolite formed in soybean growth. Since the soybean isoflavone is extracted from plants and has a structure similar to that of estrogen, the soybean isoflavone is also called phytoestrogen, can make up the defect of insufficient secretion of female estrogen after 30 years old, improve the moisture and elasticity of skin, relieve climacteric syndrome and improve osteoporosis, and make women reappear youth charm.
The Chinese patent with publication number CN101063158 is produced by using soybean molasses as material, extracting soybean isoflavone glycoside with acetone and ethyl acetate, and hydrolyzing with beta-glucosidase to obtain soybean isoflavone aglycone. The method uses a large amount of acetone and ethyl acetate solvents in the production process, the production process is complex, the solvent loss is large, the energy consumption is high, and the economic value of industrial production is not high. Chinese patent publication No. CN104844553A, whose production method is to convert glycoside type soybean isoflavone, whose content is 91.3%, into soybean isoflavone aglycone under the catalysis of lactic acid at a certain temperature and pressure. The method uses 91.3% glycoside type soybean isoflavone as raw material, has high requirement on raw material, high cost of raw material, and is difficult to realize industrialized production.
Disclosure of Invention
In view of the above, the present invention is directed to a method for extracting soybean isoflavone from soybean germ, which is a byproduct of soybean protein processing; the method has low operation cost, high extraction rate of soybean isoflavone and high purity.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for extracting soybean isoflavone from soybean germs, which comprises the following steps:
1) Micronizing soybean germs to obtain soybean germ powder;
2) Mixing the soybean germ powder with water, and emulsifying to obtain soybean germ emulsion;
3) Mixing the soybean germ emulsion with a solvent, and performing jet cavitation to obtain a solvent extracting solution;
4) And mixing and homogenizing the solvent extracting solution, ethyl acetate, n-butanol and water, and performing high-efficiency countercurrent chromatography to separate the soybean isoflavone.
Preferably, the particle size of the soybean germ powder in step 1) is 10 to 12nm.
Preferably, the mass ratio of the soybean germ powder to the water in the step 2) is 1 (4-6); the temperature of the water is 32-40 ℃.
Preferably, the solvent in step 3) is petroleum ether; the boiling range of the petroleum ether is 60-90 ℃.
Preferably, the volume ratio of the soybean germ emulsion to the solvent is 1 (1.5-2.5).
Preferably, the cavitation pressure of the jet cavitation in the step 3) is 200-220 MPa, the temperature of the jet cavitation is less than or equal to 45 ℃, and the treatment time of the jet cavitation is 1-3 h.
Preferably, the volume ratio of the solvent extraction liquid, the ethyl acetate, the n-butanol and the water in the step 4) is 3.
Preferably, the conditions of the high performance counter-current chromatography separation are as follows: the temperature of the main machine is 28 ℃, the rotating speed is 500-600 rpm, and the flow rate is 10-20L/min.
Preferably, the high performance countercurrent chromatography of the step 4) further comprises the steps of decompression concentration and freeze drying which are carried out in sequence.
Preferably, the vacuum degree of the reduced pressure concentration is 0.12-0.16 MPa, and the temperature of the reduced pressure concentration is 45-60 ℃; the temperature of the freeze-drying cold trap is-60 ℃ to-80 ℃, the vacuum degree of the freeze-drying is 80Pa to 120Pa, and the time of the freeze-drying is 5 to 6 hours.
The invention has the beneficial effects that: compared with the prior art, the method for extracting isoflavone from soybean germs provided by the invention has the advantages that: the soybean germs are crushed in a superfine mode, the cell destruction effect is good, the jet cavitation treatment is combined, the extraction rate of the soybean isoflavone is remarkably increased, and the extraction rate can reach 94.8% -96.2%. The method separates and separates the soybean isoflavone by using the high-efficiency countercurrent chromatography, and has remarkable separation effect; the purity is high.
Furthermore, the extraction method of the invention uses the technologies of decompression concentration and freeze drying to furthest keep the activity of the soybean isoflavone not to be damaged, and the purity is as high as 95.59-98.32%.
Detailed Description
The invention provides a method for extracting soybean isoflavone from soybean germs, which comprises the following steps: 1) Micronizing soybean germs to obtain soybean germ powder; 2) Mixing the soybean germ powder with water, and emulsifying to obtain soybean germ emulsion; 3) Mixing the soybean germ emulsion with a solvent, and performing jet cavitation to obtain a solvent extract; 4) And mixing and homogenizing the solvent extracting solution, ethyl acetate, n-butanol and water, and performing high-efficiency countercurrent chromatography to separate the soybean isoflavone.
In the present invention, soybean germs are ultrafinely pulverized to obtain soybean germ powder. In the present invention, the particle size of the soybean germ powder is preferably 10 to 12nm, and more preferably 11nm. In the invention, the superfine grinding is preferably realized by using a superfine grinder, and the superfine grinder has no special requirement and can adopt a conventional superfine grinder in the field. In the present invention, the soybean germ is preferably a soybean protein processing byproduct.
After the soybean germ powder is obtained, the soybean germ powder is mixed with water and emulsified to obtain the soybean germ emulsion. In the present invention, the mass ratio of the soybean germ powder to water is preferably 1 (4-6), more preferably 1; the temperature of the water is preferably 32-40 ℃; the temperature of the water is in the above range, which is more beneficial to emulsification, in the present invention, the emulsification is realized by stirring, the stirring speed is preferably 500 to 600rad/min, and the stirring time is preferably 8 to 10min.
After the soybean germ emulsion is obtained, the soybean germ emulsion and a solvent are mixed for jet cavitation to obtain a solvent extracting solution. In the present invention, the solvent is preferably petroleum ether; the boiling range of the petroleum ether is preferably 60 ℃ to 90 ℃. In the present invention, the volume ratio of the soybean germ emulsion to the solvent is preferably 1 (1.5 to 2.5), more preferably 1. In the invention, the jet cavitation is preferably carried out by using a jet cavitation machine; the invention has no special limitation on the manufacturer and the model of the jet cavitation machine, and is carried out by adopting the conventional jet cavitation machine in the field. In the invention, the cavitation pressure of the jet cavitation is preferably 200-220 MPa, and more preferably 205-215 MPa; the temperature of the jet cavitation is preferably less than or equal to 45 ℃, and the treatment time of the jet cavitation is preferably 1-3 h, and more preferably 2h. In the invention, after the jet cavitation treatment, solvent extract, water extract and residue are obtained; the solvent extract is collected to carry out the next operation.
The soybean isoflavone extracting solution is obtained by mixing and homogenizing the solvent extracting solution, ethyl acetate, n-butanol and water, and then performing high-efficiency countercurrent chromatography separation to obtain the soybean isoflavone. In the present invention, the volume ratio of the solvent extract, ethyl acetate, n-butanol and water is preferably 3. In the present invention, the conditions for the high performance countercurrent chromatography are preferably as follows: the temperature of the main engine is preferably 28 ℃, the rotating speed is preferably 500-600 rpm, and more preferably 520-580 rpm; the flow rate is preferably 10 to 20L/min, more preferably 12 to 18L/min. In the present invention, the high performance counter current chromatography separation is preferably performed using Thermo HPCCC.
The invention also preferably comprises the steps of decompression concentration and freeze drying which are sequentially carried out after the high-efficiency countercurrent chromatography separation. In the present invention, the vacuum degree of the vacuum concentration is preferably 0.12 to 0.16MPa, more preferably 0.13 to 0.15MPa; the temperature of the reduced pressure concentration is preferably 45-60 ℃, and more preferably 50-55 ℃; in the present invention, the concentration under reduced pressure is preferably performed by using a rotary evaporator of swiss cookie. In the invention, the temperature of the cold trap of the freeze drying is preferably-60 ℃ to-80 ℃, and the vacuum degree of the freeze drying is preferably 80Pa to 120Pa, and more preferably 90 Pa to 110Pa; the freeze-drying time is preferably 5 to 6 hours, and more preferably 5.2 to 5.8 hours. The freeze drying equipment is not particularly limited, and a freeze dryer which is conventional in the field can be adopted.
The invention obtains soybean isoflavone after the freeze drying; the purity of the soybean isoflavone is 95.59 to 98.32 percent.
The technical solutions provided by the present invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the present invention.
Example 1
A process for extracting isoflavones from soy germ, said process comprising the steps of:
(1) Micronizing soybean germ with particle size of 10nm;
(2) Adding water for emulsification, wherein the mass ratio of the soybean germ powder to the water is 1; adding petroleum ether (60-90 ℃) into the soybean germ emulsion, and then performing jet cavitation, wherein the volume ratio of the germ solution to the petroleum ether (60-90 ℃) is 1; the jet cavitation machine is used for treating for 1h under the conditions that the cavitation pressure is 200MPa, the temperature is less than or equal to 45 ℃. And separating in a horizontal three-phase separator to obtain solvent extract, residue and water extract.
(3) Taking a solvent extracting solution, adding ethyl acetate, n-butanol and water, wherein the volume ratio of the solvent extracting solution to the ethyl acetate to the n-butanol to the water is 3; mixing, homogenizing, and dissolving completely; then, high performance countercurrent chromatography is carried out under the following conditions: the temperature of the host is 28 ℃, the rotating speed is 500rpm, and the flow rate is 10L/min; and collecting the separated liquid.
Concentrating the separated liquid under reduced pressure and freeze-drying; vacuum concentration at 45 deg.C under 0.12 MPa; freeze-drying at-60 deg.C under vacuum degree of 80Pa for 5 hr; obtaining the soybean isoflavone freeze-dried powder.
The extraction rate of the soybean isoflavone is obviously improved, the extraction rate reaches 94.8 percent, and the purity reaches 95.59 percent.
Wherein m1 is the mass of the extracted isoflavone; m2 is the mass of soybean isoflavone in the germ.
Example 2
A process for extracting isoflavones from soy germ, said process comprising the steps of:
(1) Micronizing soybean germ with particle size of 11nm;
(2) Adding water for emulsification, wherein the mass ratio of the soybean germ powder to the water is 1; adding petroleum ether (60-90 ℃) into the soybean germ emulsion, and then performing jet cavitation, wherein the volume ratio of the germ solution to the petroleum ether (60-90 ℃) is 1; the jet cavitation machine is used for treating for 2 hours under the conditions that the cavitation pressure is 210MPa, the temperature is less than or equal to 45 ℃. And separating in a horizontal three-phase separator to obtain solvent extract, residue and water extract.
(3) Taking a solvent extracting solution, adding ethyl acetate, n-butanol and water, wherein the volume ratio of the solvent extracting solution to the ethyl acetate to the n-butanol to the water is 3; mixing, homogenizing, and dissolving completely; then, high performance countercurrent chromatography is carried out under the following conditions: the temperature of the host is 28 ℃, the rotating speed is 550rpm, and the flow rate is 15L/min; and collecting the separated liquid.
Concentrating the separated liquid under reduced pressure and freeze-drying; vacuum concentrating at 53 deg.C under 0.14 MPa; freeze drying at-70 deg.C under vacuum degree of 100Pa for 5.5 hr; obtaining the soybean isoflavone freeze-dried powder.
The extraction rate of the soybean isoflavone is obviously improved, the extraction rate reaches 95.6 percent, and the purity reaches 97.59 percent.
Example 3
A process for extracting isoflavones from soy germ, said process comprising the steps of:
(1) Micronizing soybean germ with particle size of 12nm;
(2) Adding water for emulsification, wherein the mass ratio of the soybean germ powder to the water is 1; adding petroleum ether (60-90 ℃) into the soybean germ emulsion, and then performing jet cavitation, wherein the volume ratio of the germ solution to the petroleum ether (60-90 ℃) is 1; the jet cavitation machine is used for treating for 3 hours under the conditions that the cavitation pressure is 220MPa, the temperature is less than or equal to 45 ℃. And separating in a horizontal three-phase separator to obtain solvent extract, residue and water extract.
(3) Taking a solvent extracting solution, adding ethyl acetate, n-butanol and water, wherein the volume ratio of the solvent extracting solution to the ethyl acetate to the n-butanol to the water is 3; mixing, homogenizing, and dissolving completely; then, high performance countercurrent chromatography is carried out under the following conditions: the temperature of the host is 28 ℃, the rotating speed is 600rpm, and the flow rate is 20L/min; and collecting the separated liquid.
Concentrating the separated liquid under reduced pressure and freeze-drying; vacuum concentration at 60 deg.C under 0.16 MPa; freeze-drying at-80 deg.C under vacuum degree of 120Pa for 6h; obtaining the soybean isoflavone freeze-dried powder.
The extraction rate of the soybean isoflavone is obviously improved, the extraction rate reaches 96.2 percent, and the purity reaches 98.32 percent.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and amendments can be made without departing from the principle of the present invention, and these modifications and amendments should also be considered as the protection scope of the present invention.
Claims (5)
1. A method for extracting isoflavone from soybean germ comprises the following steps:
1) Micronizing soybean germs to obtain soybean germ powder;
2) Mixing the soybean germ powder with water, and emulsifying to obtain soybean germ emulsion;
3) Mixing the soybean germ emulsion with a solvent, and performing jet cavitation to obtain a solvent extracting solution;
4) Mixing and homogenizing the solvent extracting solution, ethyl acetate, n-butanol and water, and performing high-efficiency countercurrent chromatography to obtain soybean isoflavone;
in the step 2), the mass ratio of the soybean germ powder to the water is 1 (4 to 6); the temperature of the water is 32 to 40 ℃;
the solvent in the step 3) is petroleum ether; the boiling range of the petroleum ether is 60-90 ℃;
the cavitation pressure of the jet cavitation in the step 3) is 200 to 220MPa, the temperature of the jet cavitation is less than or equal to 45 ℃, and the treatment time of the jet cavitation is 1 to 3h;
the volume ratio of the solvent extracting solution, the ethyl acetate, the n-butanol and the water in the step 4) is (3);
the conditions of the high-efficiency countercurrent chromatographic separation are as follows: the temperature of the host is 28 ℃, the rotating speed is 500 to 600rpm, and the flow rate is 10 to 20L/min.
2. The method according to claim 1, wherein the particle size of the soybean germ powder in step 1) is 10 to 12nm.
3. The method according to claim 1, wherein the volume ratio of the soybean germ emulsion to the solvent is 1 (1.5 to 2.5).
4. The method according to claim 1, wherein the high performance countercurrent chromatography of step 4) is further followed by a vacuum concentration and a freeze drying step in sequence.
5. The method as claimed in claim 4, wherein the vacuum degree of the reduced pressure concentration is 0.12 to 0.16MPa, and the temperature of the reduced pressure concentration is 45 to 60 ℃; the temperature of the cold trap for freeze drying is-60 ℃ to-80 ℃, the vacuum degree of the freeze drying is 80Pa to 120120Pa, and the time of the freeze drying is 5 to 6h.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102838575A (en) * | 2012-08-30 | 2012-12-26 | 东北农业大学 | Method for extracting isoflavone in soybean germ with aid of extrusion and expansion pretreatments |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102838575A (en) * | 2012-08-30 | 2012-12-26 | 东北农业大学 | Method for extracting isoflavone in soybean germ with aid of extrusion and expansion pretreatments |
Non-Patent Citations (4)
| Title |
|---|
| Applications and opportunities for ultrasound assisted extraction in the food industry — A review;Kamaljit Vilkhu et al;《Innovative Food Science & Emerging Technologies》;20081231(第9期);第161-169页 * |
| 大豆异黄酮分离及其检测方法的研究进展;高荣海 等;《中国调味品》;20060731(第7期);第4-8,18页 * |
| 大豆异黄酮提取方法的研究进展;卢丞文 等;《吉林农业》;20170808(第15期);第111页 * |
| 高温豆粕大豆分离蛋白射流空化辅助提取;李良 等;《农业机械学报》;20190930;第50卷(第9期);第373-380页 * |
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