CN111117773A - Method for separating nervonic acid from garlic oil and application thereof - Google Patents
Method for separating nervonic acid from garlic oil and application thereof Download PDFInfo
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- CN111117773A CN111117773A CN201911360736.9A CN201911360736A CN111117773A CN 111117773 A CN111117773 A CN 111117773A CN 201911360736 A CN201911360736 A CN 201911360736A CN 111117773 A CN111117773 A CN 111117773A
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
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Abstract
The invention discloses a method for separating nervonic acid from garlic oil, which comprises the following steps: pretreating Bulbus Allii, extracting oil, purifying oil, and separating nervonic acid by column chromatography. The invention adopts the plant chemical separation and purification technology and the column chromatography separation method to separate nervonic acid by one step to obtain a high-purity nervonic acid product with the purity of more than 95 percent and separate and obtain single-purity fatty acids such as oleic acid, erucic acid, behenic acid, arachidic acid and the like.
Description
Technical Field
The invention belongs to the field of biochemistry, and particularly relates to a method for separating nervonic acid from garlic oil and application of the method.
Background
The garlic cloves (Malania oleifera Chun et Lee) are the only single-species plants of the family Cyperaceae (Olacaceae) and the genus Malania (Malania), are also called Malania or Yunnan Tieqing trees, are specific wiggery species in China, belong to national secondary important protective plants, are mainly distributed in the local areas of Guannan, Funing and the soil between Guangxi and Yunnan in West province of south-east China, are specific single-species wiggery tree species in China, are very limited in distribution range and population number, and are listed as one of 20 extremely small populations in Yunnan province in 2010 by the nation.
The garlic seeds contain rich grease, and the content of the grease is as high as 50-55%. Wherein the fatty acid content of tetracosene-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.
GC-MS analysis of the garlic fruit oil shows that the garlic fruit oil mainly contains 7 fatty acids, namely 21.54% of oleic acid, 1.5% of palmitic acid, 7.04% of eicosene-11-acid, 18.29% of erucic acid, 1.33% of docosanoic acid, 40.92% of tetracosanoic acid and 2.14% of tetracosanoic acid, and therefore, the content of erucic acid in the garlic fruit oil is high, and a large amount of edible oil containing erucic acid can cause myocardial fibrosis to cause myocardial lesions; causing the animal to gain weight slowly and develop badly; decreased reproductive ability, etc.; this means that if nervonic acid is extracted from the garlic fruit, there is a high possibility that some of the nervonic acid will be mixed in, which reduces the purity of nervonic acid, and further reduces the quality of nervonic acid, thereby affecting the subsequent use of nervonic acid.
Therefore, how to provide a method for extracting and purifying nervonic acid by using garlic cloves as raw materials is a problem which needs to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention adopts a phytochemical separation and purification technology and a column chromatography separation method to separate nervonic acid in one step to obtain a high purity nervonic acid product with a purity of more than 95%, and to separate and obtain mono-pure fatty acids such as oleic acid, erucic acid, behenic acid, arachidic acid, etc. simultaneously.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for separating nervonic acid from oleum Bulbus Allii comprises the following steps:
step one, extracting the garlic fruit oil:
1) pretreatment: pulverizing seed kernel of Bulbus Allii, sieving with 20-40 mesh sieve, and steaming at 95-105 deg.C for 20-30min to obtain raw material;
2) extraction: according to the liquid-material ratio of 1: 3-5V: v, adding ethanol into the raw materials obtained in the step 1), and performing ultrasonic-assisted extraction for 30-40min to obtain an extracting solution;
3) and (3) purification: carrying out suction filtration on the extracting solution in the step 2), taking filtrate, concentrating under reduced pressure, and removing ethanol to obtain garlic fruit oil;
step two, separation of nervonic acid
4) Column chromatography: weighing garlic fruit oil according to the following sample amount: separating with silica gel column chromatography at silica gel amount of 1:10-20V: V, gradient eluting with petroleum ether and ethyl acetate, each gradient eluting for 4-5 retention volumes, collecting eluate containing petroleum ether and ethyl acetate at ratio of 100:3, and concentrating under reduced pressure to obtain nervonic acid.
As a preferred technical scheme of the invention, in the step 2), the power of ultrasonic-assisted extraction is 120-150w, the temperature is 30-40 ℃, and the extraction is carried out for 2-3 times.
As a preferred technical scheme of the invention, in the step 4), when gradient elution is carried out, pure petroleum ether is firstly used for elution, and the eluent is collected and concentrated under reduced pressure to obtain the mesonic acid; then adding petroleum ether: eluting ethyl acetate at a ratio of 100:1, collecting eluate, and concentrating under reduced pressure at 40-50 deg.C to obtain oleic acid; then adding petroleum ether: eluting ethyl acetate at a ratio of 100:2, collecting eluate, and concentrating under reduced pressure at 40-50 deg.C to obtain linoleic acid; eluting with petroleum ether and ethyl acetate at a ratio of 100:3, collecting eluate, and concentrating under reduced pressure at 40-50 deg.C to obtain nervonic acid; eluting with petroleum ether and ethyl acetate at a ratio of 100:10, collecting eluate, and concentrating under reduced pressure at 40-50 deg.C to obtain behenic acid; collecting petroleum ether: ethyl acetate is 100:25 parts, and is concentrated under reduced pressure at 40-50 deg.C to obtain arachidic acid.
Application of nervonic acid obtained by separating nervonic acid from oleum Bulbus Allii in preparing medicine for treating senile dementia is provided.
Application of nervonic acid obtained by separating nervonic acid from oleum Bulbus Allii in preparing medicine for resisting brain function deterioration is provided.
Application of nervonic acid obtained by a method for separating nervonic acid from allium sativum oil in preparing acetylcholinesterase inhibitor is provided.
Application of nervonic acid obtained by a method for separating nervonic acid from garlic oil in preparing functional food is provided.
According to the technical scheme, the technical effects achieved by the invention are as follows:
1) the method adopts ultrasonic wave assistance to extract oil from the garlic kernels, and adopts edible ethanol as an extraction solvent to extract the garlic kernel oil, so that the oil in the garlic kernels can be extracted to the maximum extent;
2) the equipment and reagent investment cost is low, the operation is simple, one-step extraction is realized, no waste liquid pollution is caused, and the residual residues can also be used as raw materials for extracting protein and polysaccharide;
3) the invention is the biggest highlight of the invention, the one-step extraction process which can synchronously separate 6 fatty acid pure products such as erucic acid and the like while extracting and purifying nervonic acid from the garlic fruit oil is firstly adopted to extract and purify nervonic acid contained in the garlic fruit oil by a silica gel column chromatography; the key technical key points are that mixed solvent gradient elution is adopted, 6 pure fatty acid products can be synchronously separated and refined, erucic acid with large toxic and side effects can be well separated from target product nervonic acid, erucic acid and other non-target components can be independently applied, the content and the purity of nervonic acid are also improved, the content of nervonic acid obtained by the method is up to 98%, and the nervonic acid can be used as a refined raw material for producing nervonic acid and related products.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for separating nervonic acid from oleum Bulbus Allii comprises the following steps:
step one, extracting the garlic fruit oil:
1) pretreatment: pulverizing seed kernel of Bulbus Allii, sieving with 20 mesh sieve, and steaming at 95 deg.C for 20min to obtain raw material;
2) extraction: according to the liquid-material ratio of 1: 3V: v, adding ethanol into the raw materials obtained in the step 1), and carrying out ultrasonic-assisted extraction for 30min at the temperature of 30 ℃ for 2 times with the power of 120w to obtain an extracting solution;
3) and (3) purification: carrying out suction filtration on the extracting solution in the step 2), taking filtrate, concentrating under reduced pressure, and removing ethanol to obtain garlic fruit oil;
step two, separation of nervonic acid
4) Column chromatography: weighing garlic fruit oil according to the following sample amount: separating with silica gel column chromatography at silica gel amount of 1:10V: V, eluting with pure petroleum ether, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain compound 1;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:1, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain compound 2;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:2, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain compound 3;
eluting with petroleum ether and ethyl acetate at a ratio of 100:3, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain compound 4;
eluting with petroleum ether and ethyl acetate at a ratio of 100:10, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain compound 5;
collecting petroleum ether: ethyl acetate is 100:25 parts, and is subjected to reduced pressure concentration at 40 ℃ to obtain a compound 6;
each gradient eluted 4 retention volumes.
Example 2
A method for separating nervonic acid from oleum Bulbus Allii comprises the following steps:
step one, extracting the garlic fruit oil:
1) pretreatment: pulverizing seed kernel of Bulbus Allii, sieving with 40 mesh sieve, and steaming at 105 deg.C for 30min to obtain raw material;
2) extraction: according to the liquid-material ratio of 1: 5V: v, adding ethanol into the raw materials obtained in the step 1), and extracting for 30-40min under the assistance of ultrasonic waves, wherein the power of ultrasonic-assisted extraction is 150w, the temperature is 40 ℃, and the extraction is carried out for 3 times to obtain an extracting solution;
3) and (3) purification: carrying out suction filtration on the extracting solution in the step 2), taking filtrate, concentrating under reduced pressure, and removing ethanol to obtain garlic fruit oil;
step two, separation of nervonic acid
4) Column chromatography: weighing garlic fruit oil according to the following sample amount: performing silica gel column chromatography separation at a silica gel amount of 1:20V: V, eluting with pure petroleum ether, collecting eluate, and concentrating under reduced pressure to obtain compound 1;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:1, collecting eluate, and concentrating under reduced pressure at 50 deg.C to obtain compound 2;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:2, collecting eluate, and concentrating under reduced pressure at 50 deg.C to obtain compound 3;
eluting with petroleum ether and ethyl acetate at a ratio of 100:3, collecting eluate, and concentrating under reduced pressure at 50 deg.C to obtain compound 4;
eluting with petroleum ether and ethyl acetate at a ratio of 100:10, collecting eluate, and concentrating under reduced pressure at 50 deg.C to obtain compound 5;
collecting petroleum ether: ethyl acetate is 100:25 parts, and is subjected to reduced pressure concentration at 50 ℃ to obtain a compound 6;
each gradient eluted 5 retention volumes.
Example 3
A method for separating nervonic acid from oleum Bulbus Allii comprises the following steps:
step one, extracting the garlic fruit oil:
1) pretreatment: pulverizing seed kernel of Bulbus Allii, sieving with 30 mesh sieve, and steaming at 100 deg.C for 25min to obtain raw material;
2) extraction: according to the liquid-material ratio of 1: 4V: v, adding ethanol into the raw materials obtained in the step 1), and extracting for 30-40min under the assistance of ultrasonic waves, wherein the power of the ultrasonic-assisted extraction is 130w, the temperature is 35 ℃, and the extraction is carried out for 3 times to obtain an extracting solution;
3) and (3) purification: carrying out suction filtration on the extracting solution in the step 2), taking filtrate, concentrating under reduced pressure, and removing ethanol to obtain garlic fruit oil;
step two, separation of nervonic acid
4) Column chromatography: weighing garlic fruit oil according to the following sample amount: performing silica gel column chromatography separation at a silica gel amount of 1:15V: V, eluting with pure petroleum ether, collecting eluate, and concentrating under reduced pressure to obtain compound 1;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:1, collecting eluate, and concentrating under reduced pressure at 45 deg.C to obtain compound 2;
then adding petroleum ether: eluting with ethyl acetate at a ratio of 100:2, collecting eluate, and concentrating under reduced pressure at 45 deg.C to obtain compound 3;
eluting with petroleum ether and ethyl acetate at a ratio of 100:3, collecting eluate, and concentrating at 45 deg.C under reduced pressure to obtain compound 4;
eluting with petroleum ether and ethyl acetate at a ratio of 100:10, collecting eluate, and concentrating at 45 deg.C under reduced pressure to obtain compound 5;
collecting petroleum ether: ethyl acetate is 100:25 parts, and is subjected to vacuum concentration at 45 ℃ to obtain a compound 6;
each gradient eluted 5 retention volumes.
Example 4
Structural identification of the compounds:
after GC-MS analysis of the monomeric compound obtained in example 3, the compound was identified, and the retention time and the percentage of the component content thereof are shown in tables 1 to 6.
TABLE 1 Compound 1 Retention time and percent amounts
Table 2 retention time and percent content of compound 2
Table 3 retention time and percent content of compound 3
Table 4 retention time and percent content of compound 4
TABLE 5 Retention time and percent Compound 5
TABLE 6 Retention time and percent content of Compound 6
As can be seen from tables 1 to 6, compound 1 is erucic acid, compound 2 is oleic acid, compound 3 is linoleic acid, compound 4 is nervonic acid, compound 5 is behenic acid, and compound 6 is arachidic acid; it is proved that other impurities can be effectively removed by extracting nervonic acid from the garlic fruits by the method of the embodiment 1-3, and other organic acid esters can be effectively removed by setting the gradient of the eluent, so that the purity of nervonic acid is improved, and the subsequent application of nervonic acid is facilitated.
Example 5
The nervonic acid prepared in example 3 was used as a raw material to prepare a nervonic acid emulsion, a nervonic acid hard capsule and a nervonic acid soft capsule, and the process was:
the nerve acid emulsion comprises the following components: 6.0 percent of nervonic acid, 36 percent of medicinal vegetable oil, 0.4 percent of emulsifier, 6 percent of auxiliary emulsifier, 0.08 percent of antioxidant and the balance of pharmaceutical water are added, and the mixture is prepared into nervonic acid emulsion by adopting an alternative liquid adding emulsification method under the stirring of 2000 r/min.
Nervonic acid hard capsules: nervonic acid 6%, soluble starch 54%, superfine silica gel powder 0.1%, magnesium stearate 0.6%, and sodium carboxymethylcellulose 1.5%. Stirring and uniformly mixing in a dry environment, and filling into a No. 0 capsule shell to prepare the nervonic acid hard capsule.
Nervonic acid soft capsules: nervonic acid 35%, vegetable oil 64.5% and vitamin E0.5%, stirring, mixing, and filling into gelatin soft capsule shell to obtain nervonic acid soft capsule.
In order to further investigate the effects of the nervonic acid extracted by the present invention on improving anti-senile dementia, anti-cerebral function degeneration and inhibiting the activity of acetylcholinesterase, the anti-acetylcholinesterase activity of different anti-senile dementia drugs and nervonic acid products prepared by the present invention were determined according to the theory of cholinergic injury, and the results are shown in table 7;
TABLE 7
| Sample name | Extraction method | Concentration of | AchE inhibitory Rate (%) |
| Nerve acid emulsion | Silica gel column separation | 1mg﹒mL-1 | 92.12±1.60 |
| Nervonic acid hard capsule | Silica gel column separation | 1mg﹒mL-1 | 89.56±0.15 |
| Nervonic acid soft capsule | Silica gel column separation | 1mg﹒mL-1 | 94.47±0.26 |
| Garlic fruit oil | Ultrasonic extraction | 1mg﹒mL-1 | 88.62±0.23 |
| Root of Polygala | Extracting total saponins with water | 1mg﹒mL-1 | 72.75±1.13 |
| Huperzine A | Commercially available drug | 1mg﹒mL-1 | 93.45±2.08 |
As is clear from table 7, the nervonic acid prepared in example 3 has a significant inhibitory effect on acetylcholinesterase, and thus can improve senile dementia and prevent brain function deterioration.
The principle is as follows: acetylcholine is the most important neurotransmitter in the brain nerves of mammals, the content of acetylcholine between neurons directly influences the information transmission function of central nerves, and the level of the neurotransmitter acetylcholine in the brain of a patient with brain function degeneration is obviously reduced. The effect of nervonic acid against senile dementia is mainly realized by the regulation and control of acetylcholine enzyme which has hydrolysis effect on acetylcholine. The content of the acetylcholine is controlled by the hydrolysis of the acetylcholinesterase, the nervonic acid has obvious inhibition effect on the acetylcholinesterase, and the nervonic acid can reduce the action of the acetylcholinesterase on hydrolyzing the acetylcholine through inhibiting the activity of the acetylcholinesterase, so that the content of the acetylcholine in the brain of a patient can be improved, and the effect and the action of the medicament on resisting cerebral function degeneration diseases such as senile dementia and the like can be proved by measuring the inhibition rate of the medicament on the acetylcholinesterase in vitro.
Example 6
The candy suitable for the middle-aged and the elderly people is prepared by taking the nervonic acid prepared in the example 3 as a main component, and the preparation method comprises the following steps:
brain-strengthening sugar pills: 0.6% of nervonic acid, 0.6% of citric acid, 0.8% of vegetable oil, 28% of white granulated sugar and 100% of maltose syrup. Heating maltose, melting, adding white sugar and vegetable oil, adjusting acidity and taste with citric acid, adding nervonic acid dissolved in vegetable oil, stirring, pouring into a mold, and cooling to obtain nervonic acid brain strengthening sugar pill.
In order to further examine the clinical efficacy and safety of the drug of the present invention, 30 cases were selected for clinical observation of the efficacy of the functional foods and drugs of this example. The effect standard is as follows: and (3) curing: no amnesia, and normal memory. Improvement: amnesia is obviously relieved. The disease is not cured: amnesia is not improved obviously, and memory is not improved obviously.
After 30 cases of treatment, 25 cases are cured, 3 cases are improved, 2 cases are not cured, and the total effective rate is 93 percent; has no side effect and adverse reaction.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. A method for separating nervonic acid from garlic oil is characterized by comprising the following steps:
step one, extracting the garlic fruit oil:
1) pretreatment: pulverizing seed kernel of Bulbus Allii, sieving with 20-40 mesh sieve, and steaming at 95-105 deg.C for 20-30min to obtain raw material;
2) extraction: adding ethanol into the raw materials, wherein the volume ratio of the raw materials to the ethanol is 1:3-5, and performing ultrasonic-assisted extraction for 30-40min to obtain an extracting solution;
3) and (3) purification: filtering the extractive solution, concentrating the filtrate under reduced pressure, and removing ethanol to obtain oleum Bulbus Allii; this process is not problematic.
Step two, separation of nervonic acid
4) Column chromatography: weighing garlic fruit oil according to the following sample amount: separating with silica gel column chromatography with silica gel amount of 1:10-20(V: V), gradient eluting with petroleum ether and ethyl acetate, each gradient eluting with 4-5 retention volumes, collecting eluate containing petroleum ether and ethyl acetate at ratio of 100:3, and concentrating under reduced pressure to obtain nervonic acid.
2. The method as claimed in claim 1, wherein the ultrasonic-assisted extraction power in step 2) is 120-150w, the temperature is 30-40 ℃, and the extraction is performed for 2-3 times.
3. The method for separating nervonic acid from garlic oil as claimed in claim 2, wherein in step 4), the gradient elution is performed by eluting with pure petroleum ether, collecting the eluate, and concentrating under reduced pressure to obtain the mesonic acid.
4. Use of nervonic acid obtained by the method for separating nervonic acid from allium sativum oil according to any one of claims 1 to 3 in the preparation of a medicament for treating senile dementia.
5. Use of nervonic acid obtained by the method for separating nervonic acid from allium sativum oil according to any one of claims 1 to 3 in the preparation of a medicament for treating brain function deterioration.
6. Use of nervonic acid obtained by the method for separating nervonic acid from allium sativum oil according to any one of claims 1 to 3 for preparing acetylcholinesterase inhibitor.
7. Use of nervonic acid obtained by the method for separating nervonic acid from oil of garlic bulbs according to any one of claims 1 to 3 for the preparation of functional foods.
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| CN112391420A (en) * | 2020-11-05 | 2021-02-23 | 南京康齐生物科技有限公司 | Method for extracting high-purity nervonic acid in garlic fruit oil |
| CN112545036A (en) * | 2020-12-11 | 2021-03-26 | 广西科技大学 | Garlic fruit oil microcapsule and preparation method thereof |
| CN113683500A (en) * | 2021-09-02 | 2021-11-23 | 禾大西普化学（四川）有限公司 | Separation and purification method of long-chain fatty acid |
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| CN107353199A (en) * | 2017-08-10 | 2017-11-17 | 王显权 | The method of Malania Oleifera Oil separating-purifying nervonic acid |
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| CN112391420A (en) * | 2020-11-05 | 2021-02-23 | 南京康齐生物科技有限公司 | Method for extracting high-purity nervonic acid in garlic fruit oil |
| CN112545036A (en) * | 2020-12-11 | 2021-03-26 | 广西科技大学 | Garlic fruit oil microcapsule and preparation method thereof |
| CN113683500A (en) * | 2021-09-02 | 2021-11-23 | 禾大西普化学（四川）有限公司 | Separation and purification method of long-chain fatty acid |
| CN113683500B (en) * | 2021-09-02 | 2024-04-16 | 禾大西普化学（四川）有限公司 | Separation and purification method of long-chain fatty acid |
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