CN109355138A - A kind of preparation method, product and its application of tea oil polyunsaturated fatty acid - Google Patents
A kind of preparation method, product and its application of tea oil polyunsaturated fatty acid Download PDFInfo
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- CN109355138A CN109355138A CN201710929763.8A CN201710929763A CN109355138A CN 109355138 A CN109355138 A CN 109355138A CN 201710929763 A CN201710929763 A CN 201710929763A CN 109355138 A CN109355138 A CN 109355138A
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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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
- C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/82—Theaceae (Tea family), e.g. camellia
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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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
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Abstract
The invention discloses preparation method, product and its applications of a kind of tea oil polyunsaturated fatty acid.Tea oil polyunsaturated fatty acid is made in the preparation method as follows: ethyl alcohol and basic catalyst being added in tea-seed oil, is stirred to react, with hydrochloric acid conditioning solution pH；Lipoxidase is added, is stirred to react, adds sodium hydrogensulfite and be stirred to react；With hydrochloric acid conditioning solution pH, stratification removes oil reservoir, and water layer is extracted with ether, retains extract liquor；After ether extraction liquid recycles ether, dehydrating agent and dewatering and filtering is added, filtrate is tea oil polyunsaturated fatty acid.It can be used for preparing oxidation resistant pharmaceutical preparation.It is separated the selectively acting of linoleic acid plus linolenic acid using lipoxidase by the present invention with oleic acid, due to lipoxidase action temperature and, it is not cracking linoleic acid plus linolenic acid, so as to restore to obtain linoleic acid plus linolenic acid, therefore is better than chemical oxidizing agent.
Description
Technical field
The invention belongs to field of medicaments, and in particular to a kind of preparation method of tea oil polyunsaturated fatty acid, product and its
Using.
Background technique
Polyunsaturated fatty acid content in tea oil is 7~13%, predominantly linoleic acid plus linolenic acid, has anti-inflammatory, tune
Blood lipid, antiatherosclerosis, anti-the effects of being mutated and is antitumor.
The separation method of unsaturated fatty acid mainly has solvent crystallization partition method, tydrophilization method, molecularly distilled, urea
Inclusion method etc..Tea oil mid-oleic is high, therefore has and isolate and purify oleic acid report from tea oil.Chinese patent CN101845362A is public
A kind of saponification of tea oil has been opened, has been acidified at fatty acid mixed, then through urea clathrate and removes saturated fatty acid, to improve oleic acid purity
Method.However due in tea oil content of polyunsaturated fatty acid it is low, linoleic acid plus linolenic acid and oleic acid property are very close, use
The product purity of above method separation is not high.And the difference of tea oil linoleic acid plus linolenic acid molecular structure is utilized, using selectivity
The lipoxygenase of effect acts on and isolated method has not been reported.
Summary of the invention
(1) technical problems to be solved
In view of the deficiencies of the prior art, the technical problem to be solved in the present invention is to provide a kind of tea oil polyunsaturated fatty acids
Preparation method, the present invention also provides the tea oil polyunsaturated fatty acid being prepared by this method and the tea oil are more
The application of unsaturated fatty acid.
(2) technical solution
In order to solve the above-mentioned technical problems, the present invention provides the preparation sides of such a tea oil polyunsaturated fatty acid
Method includes the following steps:
A. its 0.5~3 times of ethyl alcohol of quality, 0.2~2% basic catalyst is added in tea-seed oil, at 60~90 DEG C
It is stirred to react 1~5h, adds 0.5~2 times of reaction solution volume of water, and with hydrochloric acid conditioning solution pH to 8~10；
B. 20~40 DEG C are down to temperature, be added reaction solution volume (1~9) × 105The lipoxidase of U/mL, stirring are anti-
2~4h is answered, the sodium hydrogensulfite of tea seed oil quality 0.2~1% is added, is stirred to react 0.5~2h；
C. hydrochloric acid conditioning solution pH to 3~5 is used, stratification removes oil reservoir, and water layer is extracted with 2~5 times of its volume of ether
It takes, retains extract liquor；
D. after ether extraction liquid recycling ether, the dehydrating agent of addition extract liquor volume 1~5 (g/100mL), 150~200 DEG C
It is dehydrated 1~5h, filtering, filtrate is tea oil polyunsaturated fatty acid.
Preferably, in step, basic catalyst is any one in sodium ethoxide, sodium hydroxide or potassium hydroxide.
Preferably, in step A and step B, the mixing speed being stirred to react is 100~1000 revs/min.
Preferably, in step D, dehydrating agent is one of zeolite, activated alumina, molecular sieve or a variety of.
The present invention also provides one kind to be prepared tea oil polyunsaturated fatty acid, linoleic acid and Asia by the above method
The content of numb acid is 50~80%.
The present invention also provides a kind of applications that tea oil polyunsaturated fatty acid is prepared by the above method, are used for
Prepare oxidation resistant pharmaceutical preparation.
Preferably, pharmaceutical preparation is folk prescription or compound preparation containing tea oil polyunsaturated fatty acid.
Preferably, pharmaceutical preparation is any one of external application, oral or injectable pharmaceutically dosage form.
The principle of the present invention: lipoxidase forms hydroperoxylinoleic acid to linoleic acid plus linolenic acid selectively acting
With hydroperoxidation linolenic acid, become hydroxylinolic acid and hydroxyl linolenic acid after bisulfite sodium reduction, alcohol-soluble and water-soluble is substantially
It improves, to be separated with oleic acid.It is reduced into ethylene linkage through ether extracting and enriching, then through dehydrating agent intramolecular dehydration, is obtained rich in Asia
Oleic acid and linolenic tea oil unsaturated fatty acid.
(3) beneficial effect
The present invention has the following advantages and effects with respect to the prior art:
1. it is separated the selectively acting of linoleic acid plus linolenic acid using lipoxidase by the present invention with oleic acid, due to
The action temperature of lipoxidase and, be not cracking linoleic acid plus linolenic acid, so as to restore to obtain linoleic acid plus linolenic acid,
Therefore it is better than chemical oxidizing agent；
2. the method for the present invention can significantly improve the purity of tea oil polyunsaturated fatty acid, better than current all methods；
3. preparation process of the present invention is simple, it is convenient for industrialized production.
Specific embodiment
It, below will be right to be easy to understand the technical means, the creative features, the aims and the efficiencies achieved by the present invention
Technical solution in the embodiment of the present invention carries out clear, complete description, with the present invention is further explained, it is clear that described
Embodiment is only a part of the embodiments of the present invention, instead of all the embodiments.
Embodiment 1
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 0.5kg, the sodium ethoxide of 2g is added, is stirred to react 1h for 1000 revs/min at 60 DEG C,
2 times of reaction solution volume of water is added, with hydrochloric acid conditioning solution pH to 8；
B. 20 DEG C are down to temperature, reaction solution volume 1 × 10 is added5The lipoxidase of U/mL, 1000 revs/min of stirrings
2h is reacted, adds the sodium hydrogensulfite of 2g, 1000 revs/min are stirred to react 0.5h；
C. hydrochloric acid conditioning solution pH to 3 is used, stratification removes oil reservoir, and water layer is extracted with 5 times of its volume of ether, protected
Stay extract liquor；
D. after ether extraction liquid recycling ether, the zeolite of extract liquor volume 1 (g/100mL) is added, is dehydrated at 200 DEG C
1h, filtering, obtains tea oil polyunsaturated fatty acid 120g.
Embodiment 2
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 3kg, the sodium hydroxide of 20g is added, is stirred to react 3h for 100 revs/min at 90 DEG C,
0.5 times of reaction solution volume of water is added, with hydrochloric acid conditioning solution pH to 10；
B. 40 DEG C are down to temperature, reaction solution volume 9 × 10 is added5The lipoxidase of U/mL, 100 revs/min of stirrings
4h is reacted, adds the sodium hydrogensulfite of 10g, 100 revs/min are stirred to react 2h；
C. hydrochloric acid conditioning solution pH to 5 is used, stratification removes oil reservoir, and water layer is extracted with 2 times of its volume of ether, protected
Stay extract liquor；
D. after ether extraction liquid recycling ether, the activated alumina of extract liquor volume 5 (g/100mL) is added, at 180 DEG C
It is dehydrated 3h, filtering obtains tea oil polyunsaturated fatty acid 150g.
Embodiment 3
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 1kg, the potassium hydroxide of 10g is added, is stirred to react 5h for 500 revs/min at 80 DEG C,
1 times of reaction solution volume of water is added, with hydrochloric acid conditioning solution pH to 9；
B. 30 DEG C are down to temperature, reaction solution volume 5 × 10 is added5The lipoxidase of U/mL, 500 revs/min of stirrings
3h is reacted, adds the sodium hydrogensulfite of 5g, 500 revs/min are stirred to react 1h；
C. hydrochloric acid conditioning solution pH to 4 is used, stratification removes oil reservoir, and water layer is extracted with 3 times of its volume of ether, protected
Stay extract liquor；
D. after ether extraction liquid recycling ether, the molecular sieve of extract liquor volume 3 (g/100mL) is added, is dehydrated at 150 DEG C
5h, filtering, obtains tea oil polyunsaturated fatty acid 250g.
Embodiment 4
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 2kg, the sodium ethoxide of 15g is added, 4h is stirred to react for 300 revs/min at 70 DEG C, adds
The water for entering 1.5 times of reaction solution volume, with hydrochloric acid conditioning solution pH to 8.5；
B. 25 DEG C are down to temperature, reaction solution volume 3 × 10 is added5The lipoxidase of U/mL, 300 revs/min of stirrings
2.5h is reacted, adds the sodium hydrogensulfite of 6g, 300 revs/min are stirred to react 1.5h；
C. hydrochloric acid conditioning solution pH to 3.5 is used, stratification removes oil reservoir, and water layer is extracted with 2.5 times of its volume of ether
It takes, retains extract liquor；
D. after ether extraction liquid recycling ether, the zeolite of extract liquor volume 1.5 (g/100mL) is added, is dehydrated at 180 DEG C
1.5h, filtering, obtains tea oil polyunsaturated fatty acid 135g.
Embodiment 5
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 2.5kg, the sodium hydroxide of 12g is added, is stirred to react for 600 revs/min at 85 DEG C
2 times of reaction solution volume of water is added, with hydrochloric acid conditioning solution pH to 9.5 in 2.5h；
B. 35 DEG C are down to temperature, reaction solution volume 6 × 10 is added5The lipoxidase of U/mL, 600 revs/min of stirrings
3.5h is reacted, adds the sodium hydrogensulfite of 7g, 600 revs/min are stirred to react 1.5h；
C. hydrochloric acid conditioning solution pH to 3 is used, stratification removes oil reservoir, and water layer is extracted with 3.5 times of its volume of ether,
Retain extract liquor；
D. after ether extraction liquid recycling ether, the activated alumina of extract liquor volume 4 (g/100mL) is added, at 170 DEG C
It is dehydrated 2.5h, filtering obtains tea oil polyunsaturated fatty acid 146g.
Embodiment 6
The preparation method of tea oil polyunsaturated fatty acid, step are as follows:
A. 1kg tea-seed oil is taken, the ethyl alcohol of 1.6kg, the potassium hydroxide of 8g is added, is stirred to react for 800 revs/min at 90 DEG C
1.2 times of reaction solution volume of water is added, with hydrochloric acid conditioning solution pH to 8.5 in 3h；
B. 25 DEG C are down to temperature, reaction solution volume 4 × 10 is added5The lipoxidase of U/mL, 800 revs/min of stirrings
4h is reacted, adds the sodium hydrogensulfite of 8g, 600 revs/min are stirred to react 1.5h；
C. hydrochloric acid conditioning solution pH to 5 is used, stratification removes oil reservoir, and water layer is extracted with 2 times of its volume of ether, protected
Stay extract liquor；
D. after ether extraction liquid recycling ether, the molecular sieve of extract liquor volume 2 (g/100mL) is added, is dehydrated at 160 DEG C
2h, filtering, obtains tea oil polyunsaturated fatty acid 235g.
Embodiment 7
Tea oil polyunsaturated fatty acid tests the antioxidation of mouse aging
Method: taking 90 mouse (Kunming kind is purchased from Nanfang Medical Univ's animal experimental center), weight (20 ± 2) g, with
Machine is divided into Normal group, model group, positive controls (VE) and tea oil polyunsaturated fatty acid group, and (embodiment 1-6 is prepared into
The tea oil polyunsaturated fatty acid arrived).Each experimental group stomach-filling relative medicine, while administration, positive controls, model group and tea
5%D- galactolipin 0.5mL is subcutaneously injected in the oily daily the nape of the neck of polyunsaturated fatty acid group mouse, and control group injects normal salt
Water after modeling 6 weeks, after eye socket takes blood, cervical dislocation lethal, separates liver and brain tissue, by the measurement of testing cassete operating method and based on
Calculate serum and tissue SOD, GSH-PX vigor and MDA content.
As a result: MDA content is significantly raised in exhausted mining areas serum, liver and brain tissue caused by D- galactolipin, freely
Base phase closes the activity decline of scavenger enzyme SOD and GSH-Px.Tea oil polyunsaturated fatty acid can be substantially reduced mouse aging serum, liver
The end product of metabolism MDA of lipid peroxide in dirty and brain tissue, and the activity of SOD and GSH-Px increases.Tea oil how unsaturated
The above-mentioned effect of fatty acid, shows the anti-oxidation function which increase body, has anti-aging effects.It the results are shown in Table 1, table 2, table
3。
Table 1 is influence of the tea oil polyunsaturated fatty acid to MDA content in mouse aging serum, liver and brain
Table 2 is tea oil polyunsaturated fatty acid on the active influence of SOD in mouse aging serum, liver and brain
Table 3 is tea oil polyunsaturated fatty acid on the active influence of GSH-Px in mouse aging serum, liver and brain
Embodiment 8
The tea oil polyunsaturated fatty acid 10g of Example 1~6, is uniformly mixed with 90g cyclodextrine, it is more to obtain tea oil
Unsaturated fatty acid granule.
Embodiment 9
Tea oil polyunsaturated fatty acid 10g made from Example 1~6 is added the raw E 0.5g of dimension element, is uniformly mixed, system
At soft capsule to get the soft capsule of tea oil polyunsaturated fatty acid.
Embodiment 10
The tea oil polyunsaturated fatty acid 10g of Example 1~6 is poured into small after Spheron MD 30/70 1000mL dissolution
Bottle, is made injection.
The foregoing describe technical characteristics of the invention and basic principle and associated advantages, for those skilled in the art
For, it is clear that invention is not limited to the details of the above exemplary embodiments, and without departing substantially from design of the invention or substantially special
In the case where sign, the present invention can be realized in other specific forms.It therefore, in all respects, should all be by embodiment
Regard exemplary as, and is non-limiting, the scope of the invention being indicated by the appended claims rather than by the foregoing description,
It is intended that including all changes that fall within the meaning and scope of the equivalent elements of the claims in the present invention.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiments being understood that.
Claims (6)
1. a kind of preparation method of tea oil polyunsaturated fatty acid, which comprises the steps of:
A. its 0.5~3 times of ethyl alcohol of quality, 0.2~2% basic catalyst is added in tea-seed oil, is stirred at 60~90 DEG C
1~5h is reacted, adds 0.5~2 times of reaction solution volume of water, and with hydrochloric acid conditioning solution pH to 8~10；
B. 20~40 DEG C are down to temperature, be added reaction solution volume (1~9) × 105The lipoxidase of U/mL, it is stirred to react 2~
4h adds the sodium hydrogensulfite of tea seed oil quality 0.2~1%, is stirred to react 0.5~2h；
C. hydrochloric acid conditioning solution pH to 3~5 is used, stratification removes oil reservoir, and water layer is extracted with 2~5 times of its volume of ether,
Retain extract liquor；
D. after ether extraction liquid recycling ether, the dehydrating agent of extract liquor volume 1~5 (g/100mL), 150~200 DEG C of dehydrations are added
1~5h, filtering, filtrate is tea oil polyunsaturated fatty acid.
2. a kind of preparation method of tea oil polyunsaturated fatty acid according to claim 1, which is characterized in that in step A
In, basic catalyst is any one in sodium ethoxide, sodium hydroxide or potassium hydroxide.
3. a kind of preparation method of tea oil polyunsaturated fatty acid according to claim 1, which is characterized in that in step A
In step B, the mixing speed being stirred to react is 100~1000 revs/min.
4. a kind of preparation method of tea oil polyunsaturated fatty acid according to claim 1, which is characterized in that in step D
In, dehydrating agent is one of zeolite, activated alumina, molecular sieve or a variety of.
5. a kind of according to claim 1 to tea oil polyunsaturated fatty acid prepared by 4 any one the methods, feature exists
In the content of the linoleic acid plus linolenic acid of tea oil polyunsaturated fatty acid is 50~80%.
6. a kind of according to claim 1 to the tea oil polyunsaturated fatty acid and/claim of the preparation of 4 any one the methods
The application of tea oil polyunsaturated fatty acid described in 5, which is characterized in that it is used to prepare oxidation resistant pharmaceutical preparation.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108753466A (en) * | 2018-05-24 | 2018-11-06 | 华南理工大学 | A kind of tea oil linoleic acid and its preparation method and application |
| CN114381333A (en) * | 2020-10-20 | 2022-04-22 | 云南汉盟制药有限公司 | Preparation method of hemp seed oil with high polyunsaturated fatty acid content |
| CN115364161A (en) * | 2021-12-29 | 2022-11-22 | 江西环境工程职业学院 | Tea oil glycoprotein saponin nano intestinal probiotic accelerant and preparation method and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108753466A (en) * | 2018-05-24 | 2018-11-06 | 华南理工大学 | A kind of tea oil linoleic acid and its preparation method and application |
| CN108753466B (en) * | 2018-05-24 | 2021-06-08 | 华南理工大学 | Tea oil linoleic acid and preparation method and application thereof |
| CN114381333A (en) * | 2020-10-20 | 2022-04-22 | 云南汉盟制药有限公司 | Preparation method of hemp seed oil with high polyunsaturated fatty acid content |
| CN114381333B (en) * | 2020-10-20 | 2023-11-17 | 云南汉盟制药有限公司 | Preparation method of hemp seed oil with high polyunsaturated fatty acid content |
| CN115364161A (en) * | 2021-12-29 | 2022-11-22 | 江西环境工程职业学院 | Tea oil glycoprotein saponin nano intestinal probiotic accelerant and preparation method and application thereof |
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