CN112391420A - Method for extracting high-purity nervonic acid in garlic fruit oil - Google Patents
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- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01003—Triacylglycerol lipase (3.1.1.3)
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Abstract
The invention provides a method for extracting high-purity nervonic acid from garlic fruit oil. The method comprises the following steps: preparing high-activity lipase; preparing immobilized lipase; adding the garlic fruit oil into a conical flask, adding a phosphoric acid buffer solution and tween-80 of the garlic fruit oil, and emulsifying at room temperature on a constant-temperature magnetic stirrer; placing into a constant temperature magnetic stirrer, adding immobilized lipase in a constant temperature water bath at 40 deg.C, and magnetically stirring for hydrolysis; separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid; dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol; adding active carbon, stirring, heating and refluxing; filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting the pH value, and crystallizing; filtering and drying to obtain the high-purity nervonic acid. The method and the equipment adopted in the invention are simple, and the purity of the extracted nervonic acid is up to more than 95%.
Description
Technical Field
The invention relates to the field of extract preparation, in particular to a method for extracting high-purity nervonic acid in garlic fruit oil.
Background
The alliaceous garlicum is a ferrugineaceae, is mainly distributed in the southern province, the south China, the West province of Yunnan province, the Funing province and the local region where the southern province and the Yunnan province are bordered by the western province of Guangxi, is a unique single species of wiggle tree species in China, and is listed as one of 20 extremely small populations in the Yunnan province in 2010 due to very limited distribution range and population quantity.
The garlic seeds contain rich grease, and the content of the grease is as high as 50-55%. Wherein the fatty acid proportion of tetracosenic 15-olefine acid (also called nervonic acid) in the garlic fruit oil is up to 40% -50%. Nervonic acid is an unsaturated fatty acid, has a great benefit to human bodies, can restore and even enhance the activity of nerve endings, promotes the growth and development of the body into nerve cell tissues, and has good curative effect on patients with cardiovascular and cerebrovascular diseases and autoimmune deficiency diseases of human bodies.
At present, a chromatographic column chromatography is generally adopted as an extraction and purification method, but the method has high requirements on experimental instruments and the like, so that how to provide a simpler and more effective extraction and purification method is a problem to be solved by technical personnel in the field.
Disclosure of Invention
The technical problem to be solved is as follows: the invention aims to provide a method for extracting high-purity nervonic acid from garlic oil, which has simple method and equipment and can extract the nervonic acid with the purity of more than 95 percent.
The technical scheme is as follows: the method for extracting the high-purity nervonic acid in the garlic fruit oil comprises the following steps:
(1) adding PEG2000 solution and (NH) into 2g of crude lipase liquid4)2SO4Adding water to 10g of total weight for separation and extraction;
(2) centrifuging at 3000r/min for 5min, and separating phases to obtain high-activity lipase;
(3) adding 1g of dry silica gel into 20mL of acetone, uniformly mixing with 10% of 3-APTES, magnetically stirring for 2h at 50 ℃, performing suction filtration, washing with deionized water for 3-5 times, placing into a 60 ℃ oven, and drying for 2 h;
(4) adding 20mL of phosphate buffer solution with lmmol/L, pH of 7.0 into the dried silica gel, then adding 2mL of 25% glutaraldehyde, activating for 2h at 20 ℃, carrying out suction filtration on the activated silica gel, washing with deionized water, and drying for 2h at 60 ℃;
(5) adding activated silica gel into 20mL of high-activity lipase solution, fixing at 20 ℃, washing with deionized water, filtering, and air-drying at room temperature overnight to obtain immobilized lipase;
(6) adding 5ml of oleum Bulbus Allii into conical flask, adding 10ml of pH 7 phosphoric acid buffer solution and 2% Tween-80 of oleum Bulbus Allii, and emulsifying at room temperature for 10min on constant temperature magnetic stirrer;
(7) placing into a constant temperature magnetic stirrer, adding 15-20g of immobilized lipase into a constant temperature water bath at 40 ℃, and hydrolyzing for 24-48 h under magnetic stirring;
(8) separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid;
(9) dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol;
(10) adding 0.5-5wt% of active carbon, stirring, heating and refluxing for 1-3 h;
(11) filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting pH to 4-5, and crystallizing at 0-4 deg.C for 8-10 h;
(12) filtering, and drying at 35-50 deg.C for 2-7 hr to obtain high purity nervonic acid.
Further, the crude lipase liquid in the step (1) is derived from animals or microorganisms.
Further, the microorganism is Burkholderia cepacia or Pseudomonas aeruginosa.
Further, the concentration of PEG2000 in the step (1) is 25%, (NH)4)2SO4The concentration of (2) is 12%.
Further, the separation and extraction conditions in the step (1) are extraction at the temperature of 40 ℃ for 1 h.
Further, the volume ratio of the ethyl acetate to the ethanol in the step (9) is 2: 1.
Has the advantages that:
1. the invention adopts the immobilized lipase, on one hand, the high activity and stability of the lipase can be maintained, and on the other hand, the lipase is easy to separate from a reaction system, is easy to control and can be repeatedly used.
2. The method and the equipment adopted in the invention are simple, and the purity of the extracted nervonic acid is up to more than 95%.
Detailed Description
Example 1
The method for extracting the high-purity nervonic acid in the garlic fruit oil comprises the following steps:
(1) adding PEG2000 solution and (NH) into 2g of crude lipase liquid4)2SO4Adding water to total weight of 10g, and separating and extracting at 40 deg.C for 1 hr to obtain extract containing 25% PEG2000 (NH)4)2SO4The concentration of the crude lipase is 12 percent, and the crude lipase liquid is derived from pork;
(2) centrifuging at 3000r/min for 5min, and separating phases to obtain high-activity lipase;
(3) adding 1g of dry silica gel into 20mL of acetone, uniformly mixing with 10% of 3-APTES, magnetically stirring for 2h at 50 ℃, carrying out suction filtration, washing for 3 times by using deionized water, placing into a 60 ℃ drying oven, and drying for 2 h;
(4) adding 20mL of phosphate buffer solution with lmmol/L, pH of 7.0 into the dried silica gel, then adding 2mL of 25% glutaraldehyde, activating for 2h at 20 ℃, carrying out suction filtration on the activated silica gel, washing with deionized water, and drying for 2h at 60 ℃;
(5) adding activated silica gel into 20mL of high-activity lipase solution, fixing at 20 ℃, washing with deionized water, filtering, and air-drying at room temperature overnight to obtain immobilized lipase;
(6) adding 5ml of oleum Bulbus Allii into conical flask, adding 10ml of pH 7 phosphoric acid buffer solution and 2% Tween-80 of oleum Bulbus Allii, and emulsifying at room temperature for 10min on constant temperature magnetic stirrer;
(7) placing into a constant temperature magnetic stirrer, adding 15g of immobilized lipase into a constant temperature water bath at 40 ℃, and hydrolyzing for 24 h under magnetic stirring;
(8) separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid;
(9) dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol, wherein the volume ratio of the ethyl acetate to the ethanol is 2: 1;
(10) adding 0.5-5wt% of active carbon, stirring, and heating and refluxing for 1 h;
(11) filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting the pH to 4, and crystallizing for 8 hours at 0 ℃;
(12) filtering, and drying at 35 deg.C for 2 hr to obtain high-purity nervonic acid.
The purity of nervonic acid was measured, and the purity of the high-purity nervonic acid prepared in this example was measured to be 95.6%.
Example 2
The method for extracting the high-purity nervonic acid in the garlic fruit oil comprises the following steps:
(1) adding PEG2000 solution and (NH) into 2g of crude lipase liquid4)2SO4Adding water to total weight of 10g, and separating and extracting at 40 deg.C for 1 hr to obtain extract containing 25% PEG2000 (NH)4)2SO4The concentration of the crude lipase is 12 percent, and the crude lipase liquid is derived from Burkholderia cepacia;
(2) centrifuging at 3000r/min for 5min, and separating phases to obtain high-activity lipase;
(3) adding 1g of dry silica gel into 20mL of acetone, uniformly mixing with 10% of 3-APTES, magnetically stirring for 2h at 50 ℃, performing suction filtration, washing with deionized water for 4 times, placing into a 60 ℃ oven, and drying for 2 h;
(4) adding 20mL of phosphate buffer solution with lmmol/L, pH of 7.0 into the dried silica gel, then adding 2mL of 25% glutaraldehyde, activating for 2h at 20 ℃, carrying out suction filtration on the activated silica gel, washing with deionized water, and drying for 2h at 60 ℃;
(5) adding activated silica gel into 20mL of high-activity lipase solution, fixing at 20 ℃, washing with deionized water, filtering, and air-drying at room temperature overnight to obtain immobilized lipase;
(6) adding 5ml of oleum Bulbus Allii into conical flask, adding 10ml of pH 7 phosphoric acid buffer solution and 2% Tween-80 of oleum Bulbus Allii, and emulsifying at room temperature for 10min on constant temperature magnetic stirrer;
(7) putting into a constant-temperature magnetic stirrer, adding 18g of immobilized lipase into a constant-temperature water bath at 40 ℃, and hydrolyzing for 36 h under magnetic stirring;
(8) separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid;
(9) dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol, wherein the volume ratio of the ethyl acetate to the ethanol is 2: 1;
(10) adding 3wt% of active carbon, stirring, heating and refluxing for 2 h;
(11) filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting the pH to 4.5, and crystallizing for 9 hours at 2 ℃;
(12) filtering, and drying at 38 deg.C for 5 hr to obtain high-purity nervonic acid.
The purity of nervonic acid was measured, and the purity of the high-purity nervonic acid prepared in this example was measured to be 97.2%.
Example 3
The method for extracting the high-purity nervonic acid in the garlic fruit oil comprises the following steps:
(1) adding PEG2000 solution and (NH) into 2g of crude lipase liquid4)2SO4Adding water to total weight of 10g, and separating and extracting at 40 deg.C for 1 hr to obtain extract containing 25% PEG2000 (NH)4)2SO4The concentration of the lipase is 12 percent, and the crude lipase liquid is derived from pseudomonas aeruginosa;
(2) centrifuging at 3000r/min for 5min, and separating phases to obtain high-activity lipase;
(3) adding 1g of dry silica gel into 20mL of acetone, uniformly mixing with 10% of 3-APTES, magnetically stirring for 2h at 50 ℃, carrying out suction filtration, washing for 5 times by using deionized water, placing into a 60 ℃ drying oven, and drying for 2 h;
(4) adding 20mL of phosphate buffer solution with lmmol/L, pH of 7.0 into the dried silica gel, then adding 2mL of 25% glutaraldehyde, activating for 2h at 20 ℃, carrying out suction filtration on the activated silica gel, washing with deionized water, and drying for 2h at 60 ℃;
(5) adding activated silica gel into 20mL of high-activity lipase solution, fixing at 20 ℃, washing with deionized water, filtering, and air-drying at room temperature overnight to obtain immobilized lipase;
(6) adding 5ml of oleum Bulbus Allii into conical flask, adding 10ml of pH 7 phosphoric acid buffer solution and 2% Tween-80 of oleum Bulbus Allii, and emulsifying at room temperature for 10min on constant temperature magnetic stirrer;
(7) placing into a constant temperature magnetic stirrer, adding 20g of immobilized lipase into a constant temperature water bath at 40 ℃, and hydrolyzing for 48 h under magnetic stirring;
(8) separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid;
(9) dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol, wherein the volume ratio of the ethyl acetate to the ethanol is 2: 1;
(10) adding 5wt% of active carbon, stirring, heating and refluxing for 3 h;
(11) filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting the pH value to 5, and crystallizing for 10 hours at 4 ℃;
(12) filtering, and drying at 50 deg.C for 7 hr to obtain high-purity nervonic acid.
The purity of nervonic acid was measured, and the purity of the high-purity nervonic acid prepared in this example was measured to be 96.7%.
Claims (6)
1. The method for extracting the high-purity nervonic acid in the garlic fruit oil is characterized by comprising the following steps of:
(1) adding PEG2000 solution and (NH) into 2g of crude lipase liquid4)2SO4Adding water to 10g of total weight for separation and extraction;
(2) centrifuging at 3000r/min for 5min, and separating phases to obtain high-activity lipase;
(3) adding 1g of dry silica gel into 20mL of acetone, uniformly mixing with 10% of 3-APTES, magnetically stirring for 2h at 50 ℃, performing suction filtration, washing with deionized water for 3-5 times, placing into a 60 ℃ oven, and drying for 2 h;
(4) adding 20mL of phosphate buffer solution with lmmol/L, pH of 7.0 into the dried silica gel, then adding 2mL of 25% glutaraldehyde, activating for 2h at 20 ℃, carrying out suction filtration on the activated silica gel, washing with deionized water, and drying for 2h at 60 ℃;
(5) adding activated silica gel into 20mL of high-activity lipase solution, fixing at 20 ℃, washing with deionized water, filtering, and air-drying at room temperature overnight to obtain immobilized lipase;
(6) adding 5ml of oleum Bulbus Allii into conical flask, adding 10ml of pH 7 phosphoric acid buffer solution and 2% Tween-80 of oleum Bulbus Allii, and emulsifying at room temperature for 10min on constant temperature magnetic stirrer;
(7) placing into a constant temperature magnetic stirrer, adding 15-20g of immobilized lipase into a constant temperature water bath at 40 ℃, and hydrolyzing for 24-48 h under magnetic stirring;
(8) separating the oil layer, washing with water at 80 deg.C for several times until the solution is neutral, cooling to obtain mixed fatty acid solid, and drying to obtain crude product of nervonic acid;
(9) dissolving the crude product of nervonic acid by using a mixture of ethyl acetate and ethanol;
(10) adding 0.5-5wt% of active carbon, stirring, heating and refluxing for 1-3 h;
(11) filtering, concentrating to 2 times of the mass of the crude product of nervonic acid, adjusting pH to 4-5, and crystallizing at 0-4 deg.C for 8-10 h;
(12) filtering, and drying at 35-50 deg.C for 2-7 hr to obtain high purity nervonic acid.
2. The method for extracting high-purity nervonic acid from oil of garlic cloves according to claim 1, wherein the crude lipase liquid in step (1) is derived from animals or microorganisms.
3. The method for extracting high-purity nervonic acid from oil of allium sativum according to claim 2, wherein the microorganism is burkholderia cepacia or pseudomonas aeruginosa.
4. The method for extracting high-purity nervonic acid from oil of garlic fruit according to claim 1, wherein the concentration of PEG2000 in step (1) is 25%, (NH)4)2SO4The concentration of (2) is 12%.
5. The method for extracting high-purity nervonic acid from oil of garlic cloves according to claim 1, wherein the separation and extraction conditions in step (1) are extraction at 40 ℃ for 1 hour.
6. The method for extracting high-purity nervonic acid from oil of allium sativum fruit according to claim 1, wherein the volume ratio of ethyl acetate to ethanol in the step (9) is 2: 1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445826A (en) * | 2017-07-25 | 2017-12-08 | 天津泽达天健科技有限公司 | A kind of preparation method of neural acid esters |
| CN108467345A (en) * | 2018-04-10 | 2018-08-31 | 大理大学 | A kind of method and nervonic acid inclusion compound for extracting nervonic acid from malania oleifera |
| CN111117773A (en) * | 2019-12-25 | 2020-05-08 | 昆明酷特利生物科技有限公司 | Method for separating nervonic acid from garlic oil and application thereof |
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- 2020-11-05 CN CN202011220071.4A patent/CN112391420B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445826A (en) * | 2017-07-25 | 2017-12-08 | 天津泽达天健科技有限公司 | A kind of preparation method of neural acid esters |
| CN108467345A (en) * | 2018-04-10 | 2018-08-31 | 大理大学 | A kind of method and nervonic acid inclusion compound for extracting nervonic acid from malania oleifera |
| CN111117773A (en) * | 2019-12-25 | 2020-05-08 | 昆明酷特利生物科技有限公司 | Method for separating nervonic acid from garlic oil and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| 吴茜茜等: "碱性脂肪酶固定化条件及其催化生物柴油的研究", 《农业工程学报》 * |
| 杨金来等: "蒜头果油制备15-羟基十五烷酸甲酯的研究", 《应用化工》 * |
| 潘湘波等: "15-羟基十五烷酸的脂肪酶催化合成环十五内酯", 《应用化学》 * |
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