CN100368552C - Process for preparing conjugated fatty acid - Google Patents
Process for preparing conjugated fatty acid Download PDFInfo
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- CN100368552C CN100368552C CNB2004100606709A CN200410060670A CN100368552C CN 100368552 C CN100368552 C CN 100368552C CN B2004100606709 A CNB2004100606709 A CN B2004100606709A CN 200410060670 A CN200410060670 A CN 200410060670A CN 100368552 C CN100368552 C CN 100368552C
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Abstract
The present invention relates to a process for preparing conjugacy fatty acid through biological isomerization and specific isomerase produced by lactic acid bacteria. The specific isomerase isomerizing 9c, 12c unsaturated fatty acid for forming 9c, 11t conjugacy fatty acid such as 9c, 11t conjugated linoleic acid and 9c, 11t conjugacy linoleic acid. The present invention also relates to a method for preparing the conjugacy fatty acid through measures such as induction, modification, isomerase gene clone, etc. on the lactic acid bacteria, various conjugacy fatty acid products prepared by the method and lactic acid bacterium products related to the conjugacy fatty acid.
Description
Technical field
The present invention relates to prepare the method for conjugated fatty acids, specifically, described the specific isomerase that produces by milk-acid bacteria, biological isomerization prepares conjugated fatty acids, 9c specifically, 11t conjugated linolic acid, 9c, 11t conjugate linolenic acid.
Background technology
Conjugated fatty acids is meant the lipid acid that contains a pair of conjugated double bond, because it has specific physiologically active, has caused people's great attention, and as conjugated linolic acid and conjugate linolenic acid etc., studying more at present is conjugated linolic acid.(conjugated linoleic acid CLA) is one group of position (C8, C10 to conjugated linolic acid; C9, C11; C10, C12; C11 is C13) with how much (cis, cis; Cis, trans; Trans, cis; Trans, trans) 18 carbon conjugated diolefine acid of isomer general designation.At nature, CLA mainly be present in ruminating animal meat and the breast fat in, every gram fat contains 0.83-5.5mg, its isomer mainly is 9c, 11t-CLA.A large amount of CLA that studies show that have effects such as anticancer, fat-reducing, atherosclerosis, anti-type ii diabetes.The preparation method of CLA has two kinds, and a kind of is the chemical isomerization method, and another kind is biological isomerate process.The chemical isomerization method need be carried out under highly basic and high temperature, and its product is to contain 8,10-CLA, 9,11-CLA, 10,12-CLA and 11, the complex mixture of many kinds of isomer of 13-CLA
[5], contain the isomer of many non-naturals and security the unknown, the possessor attempts to use urea adduct method to the greatest extent
[6]With the lipase esterification
[7]Method is come some isomer of enrichment, but its poor selectivity may separate these isomer hardly one by one, and very uneconomical.
Biological isomerate process carries out the reaction conditions gentleness under the effect of enzyme.Kepler (1966)
[8]Find that at first the molten fine butyric acid vibrios (Butyrivibrio fibrisolvens) in the cud can be isomerizated into 9c with linolic acid, 11t-CLA, but because the cud bacterium is a strictly anaerobic bacterium, yeast culture is strict, and CLA can be reduced into saturated fatty acid, and therefore having restricted the cud bacterium is used to produce CLA.Afterwards, people were separated to the bacterium acidi propionici and the milk-acid bacteria that can produce CLA from cultured milk prod (as sour milk, cheese etc.).Jiang (1998)
[14]Milk-product starter commonly used is studied, found that propionibacterium freudenreichii (Propionibacteriumfrudenreichii) can change into CLA with free linoleic acid, 9c wherein, 11t/9t, 11c-CLA is greater than 70%.Lin (1999)
[17]From 6 kinds of milk-acid bacterias, screen a strain and produce 9c, the lactobacillus acidophil-aerogenes (Lactobacillus acidophilusCCRC14079) that the 11t-CLA amount is higher, Pariza (2000)
[20]Screen a strain lactobacillus reuteri (Lactobacillus reuteri ATCC23272) and linolic acid can be isomerizated into 9c from the linoleic mouse intestinal microflora of feeding, 11t-CLA does not generate 10t, 12c/10c, 12t c-CLA.Kishino (2002)
[12]Find the CLA that plant lactobacillus (Lactobacillus plantarum AKU1009a) isomerization generates, its isomer is by 9c, and (or 9t, 11c-CLA) and 9t, 11t-CLA forms 11t-CLA.Therefore, from the milk-acid bacteria that is easy to cultivate, screen and isomerization to form single CLA isomer, 9c particularly, 11t-CLA, to make mass preparation have the active CLA isomer of particular organisms and become possibility, and the human body probiotic bacterium, screen and have the active milk-acid bacteria of allomerase and will further widen the range of application of milk-acid bacteria.
Summary of the invention
The objective of the invention is specific isomerase by the milk-acid bacteria generation, biological isomerization prepares conjugated fatty acids, this enzyme will contain 9c, the isomerization of 12c unsaturated fatty acids forms 9c, and the 11t conjugated fatty acids is as 9c, the 11t conjugated linolic acid, 9c, the 11t conjugate linolenic acid the present invention also relates to that milk-acid bacteria is carried out means such as mutagenesis, isomerase gene clone and prepares conjugated fatty acids.
Purpose of the present invention also provides new product, prepares the various product of single conjugated fatty acids isomer and the milk-acid bacteria product relevant with conjugated fatty acids by present method.
Technical scheme of the present invention is: a kind of method for preparing conjugated fatty acids, the specific isomerase of utilizing milk-acid bacteria to produce is prepared into conjugated fatty acids by biological isomerization with lipid acid.This specific isomerase is with 9c, and the isomerization of 12c unsaturated fatty acids forms 9c, 11t conjugated fatty acids.This conjugated fatty acids can be 9c, 11t conjugated linolic acid or 9c, 11t conjugate linolenic acid.Isomerized raw material can be lipid acid, soap, fatty acid ester, glycerin fatty acid ester.This milk-acid bacteria is lactobacterium casei cheese subspecies, is numbered CGMCC1.574.Utilize the isomerized thalline of this milk-acid bacteria, enzyme extract to prepare conjugated fatty acids.This milk-acid bacteria can pass through the production level that mutagenesis, genetic modification, raising prepare conjugated fatty acids.The isomerase gene of this milk-acid bacteria can be prepared conjugated fatty acids by the clone.Medicine, healthcare products and food with conjugated fatty acids and the preparation of its derivative.
The product relevant with this milk-acid bacteria production with conjugated fatty acids.
The invention has the advantages that: present method can obtain single conjugated fatty acids isomer, and is purer than the isomer of other method.Can be used as the good production raw material.Have the active milk-acid bacteria of allomerase and will further widen the range of application of milk-acid bacteria.
Description of drawings
Fig. 1 is the UV scanning synoptic diagram of the prepared conjugated linolic acid of the present invention;
Fig. 2 is the UV scanning synoptic diagram of the prepared conjugate linolenic acid of the present invention;
Fig. 3 is the influence of linolic acid concentration to CLA;
Fig. 4 is the influence of incubation time to CLA.
Embodiment
The present invention is based on 9c, 11t-CLA is the main CLA isomer that is present in the food, and physiological function is clear and definite, and therefore screening can produce the milk-acid bacteria of specific isomerase, biological isomerization prepares conjugated fatty acids, thereby realizes a large amount of preparations and the application of single conjugated fatty acids isomer.The method that screening energy isomerization linolic acid forms CLA all has report in above-mentioned document, screen from milk-acid bacteria by this method and can form conjugated linolic acid (Fig. 1) by the isomerization linolic acid, and this bacterium can also form conjugate linolenic acid (Fig. 2) with the linolenic acid isomerization.Utilize capillary electrophoresis that the conjugated linolic acid that isomerization forms is analyzed, the conjugated linolic acid of finding isomerization formation is by single 9c, 11t-CLA forms, owing to also there are not the mark product of conjugate linolenic acid isomer at present, therefore fail to determine which kind of isomer the conjugate linolenic acid that isomerization forms is, all have 9c, the structure of the two keys of 12c and the specificity of enzyme effect according to linoleic acid plus linolenic acid, therefore infer that the isomer of conjugate linolenic acid is 9c, the 11t conjugate linolenic acid.Select suitable fermentation condition, can further improve 9c, the output of 11t-CLA is 9c, the 11t conjugate linolenic acid.Select suitable fermentation condition, can further improve 9c, the output of 11t-CLA, linoleic concentration, action time, temperature, pH, O
2Conditions such as concentration are all relevant with its output.Discover that the isomerase in this milk-acid bacteria is an intracellular enzyme, this milk-acid bacteria thalline and enzyme extract also can form conjugated fatty acids by isomerization lipid acid, for improving the utilization ratio of thalline and enzyme, increase economic benefit, also can produce conjugated fatty acids by existing fixed technology fixing cell or immobilized enzyme.The milk-acid bacteria that the present invention screens not only can the isomerization free fatty acids, but also isomerization soap (as sodium salt, calcium salt etc.), fatty acid ester (as methyl esters, ethyl ester etc.), glycerin fatty acid ester (as monoglyceride, triglyceride, triglyceride level), therefore but the transformation efficiency of free fatty acids and soap is higher, can select the method for suitable production conjugated fatty acids according to raw material and production technique for use.
Milk-acid bacteria is carried out ultraviolet mutagenesis, be separated to the mutant strain that a strain isomerization level improves, certainly, also can be by chemomorphosis, even lipid acid isomerase gene wherein cloned make up engineering strain, this is the thing that is easy to accomplish for a person skilled in the art.
The conjugated fatty acids that isomerization generates can separate by existing technology, and can reach the high purity product of pharmacy requirement.
The single conjugated fatty acids isomer that obtains can be made free fatty acids (9c according to its purposes, 11t conjugated linolic acid, 9c, the 11t conjugate linolenic acid), soap (as sodium salt, calcium salt etc.), fatty acid ester (as methyl esters, ethyl ester etc.), glyceryl ester (as monoglyceride, triglyceride, triglyceride level), it can be solid, glue or liquid.
Single conjugated fatty acids isomer and its derivative can be used as medicine, food uses.Milk-acid bacteria is a kind of human body probiotic bacterium, and the milk-acid bacteria that the present invention is used is further widened the range of application of milk-acid bacteria owing to have the activity of isomerization lipid acid.Therefore, the present invention also comprises medicine, the food relevant with conjugated fatty acids that utilizes this milk-acid bacteria to produce.
In presents, the term medicine is made a general reference all has the product of therapeuticing and health effect from product deutero-of the present invention, and has both comprised with product of the present invention being that product that main component is made also comprises the product of making as moiety or additive with it.For example medicine can be anticarcinogen, diet pill, cardiovascular disorder medicine, anti-type ii diabetes medicine, antimicrobial drug, antiviral drug, beauty treatment, skin care etc.
In this text, term food is made a general reference all edible products, and has both comprised with product of the present invention being that product that main component is made also comprises the product of making as moiety or additive with it.For example food can be grain and oil goods, milk-product, meat product, beverage, candy, protective foods etc.
In this text, milk-acid bacteria produce with the conjugated fatty acids related products, comprise with this milk-acid bacteria thalline be the product made of main component or additive, with add beverage that this milk-acid bacteria makes and milk-product, to add fermented product that this milk-acid bacteria makes etc.
Embodiment 1
The optimization of isomerisation conditions
1.1 linolic acid concentration is to the influence of conjugated linolic acid
CLA is the product that milk-acid bacteria isomerization linolic acid forms, so the linoleic concentration of substrate is one of main factor of decision CLA formation.Because the unsaturated fatty acids of high density all has restraining effect to thalli growth and metabolism, and this restraining effect is to G
+Milk-acid bacteria particularly evident, therefore in substratum, add the linolic acid that difference is measured respectively, measure the output of CLA behind the cultivation 24h, found that the CLA of the linolic acid formation of adding 0.1% (v/v) measures maximum (Fig. 3), when linolic acid concentration was higher than 0.4%, bacterial number obviously reduced.
1.2 incubation time is to the influence of CLA output
At present, generally believe that CLA is the intermediate product that the microorganism biological hydrogenation process forms, finally make polyunsaturated fatty acid be reduced into saturated and monounsaturated fatty acids by long biological hydrogenation, thereby removed the toxic action of polyunsaturated fatty acid thalline.Therefore measure the CLA output behind the different incubation times respectively, the result shows that when 42h the output of CLA reaches highest level (Fig. 4), and along with the further prolongation of time, the output of CLA constantly descends.
Embodiment 2
The isomerization of multi-form lipid acid relatively
The specific isomerase that milk-acid bacteria produces, can be with 9c, the isomerization of 12c unsaturated fatty acids forms 9c, the 11t conjugated fatty acids, for understanding this enzyme to containing 9c, the exposure level of the unsaturated fatty acid derivative of 12c structure has selected linolic acid, linolic acid sodium, Semen Maydis oil as substrate respectively, studies isomerized level.Respectively three kinds of substrates are joined in the MRS substratum by 0.1%, insert 10% bacterial classification, mixing, 30 ℃ leave standstill cultivation 42h.The linolic acid group directly goes out conjugated linolic acid with normal hexane extraction; Linolic acid sodium group is transferred pH to 2.0 with the vitriol oil earlier, goes out conjugated linolic acid with hexane extraction again; The Semen Maydis oil group is earlier used the sodium hydroxide saponification, use again in the vitriol oil and after, go out conjugated linolic acid with hexane extraction.
After measured, the isomerization level of above-mentioned 3 kinds of form lipid acid sees Table 1, and visible linolic acid and linolic acid sodium are significantly higher than Semen Maydis oil as the isomerization level of substrate.
The isomerization of the multi-form lipid acid of table 1 relatively
| Substrate | 9c, the productive rate of 11t-CLA |
| Linolic acid linolic acid sodium Semen Maydis oil | 44％ 50％ 35％ |
Embodiment 3,
The comparison of different isomerization method
Allomerase in the milk-acid bacteria is the catalyzer that biological isomerization forms conjugated fatty acids, for understand milk-acid bacteria in culturing process, the isomerization level of milk-acid bacteria thalline, milk-acid bacteria bacterial cell disruption crude enzyme liquid, studied the relation of 3 kinds of methods and CLA formation.
Milk-acid bacteria is isomerization method in culturing process: the lactic acid bacteria culturers of adding 10% and 0.1% linolic acid in the MRS substratum, and mixing, 30 ℃ leave standstill cultivation 42h.
Milk-acid bacteria thalline isomerization method: milk-acid bacteria cultivated 24h in the MRS substratum after, centrifugal collection thalline adds the phosphate buffered saline buffer of pH7.0 in the thalline after washing, make bacteria suspension, to the linolic acid that wherein adds 0.1%, mixing, 30 ℃ of standing and reacting 12h.
Milk-acid bacteria thalline crude enzyme liquid isomerization method: milk-acid bacteria cultivated 24h in the MRS substratum after, centrifugal collection thalline, the phosphate buffered saline buffer that adds pH7.0 in the thalline after washing, make bacteria suspension, the ultrasonic disruption thalline, centrifugal gained supernatant is crude enzyme liquid, to the linolic acid that wherein adds 0.1%, mixing, 30 ℃ of standing and reacting 4h.
After measured, the isomerization level of above-mentioned 3 kinds of methods sees Table 2, and visible milk-acid bacteria thalline crude enzyme liquid isomerization method is the reaction times weak point not only, and the isomerization level is also high.
The comparison of table 2 different isomerization method
| Method | Reaction total time (h) | 9c, the productive rate of 11t-CLA |
| Milk-acid bacteria is isomerization method milk-acid bacteria thalline isomerization method milk-acid bacteria thalline crude enzyme liquid isomerization method in |
42 36 28 | 46％ 53％ 61％ |
Embodiment 4
Milk-acid bacteria mutant strain by mutagenic obtained isomerization level raising
Lactic acid bacteria culture solution with the centrifugal 10min of 5000rpm, is collected thalline, and the bacteria suspension of 108CFU/ml is made in washing after centrifugal.Bacteria suspension is sub-packed in the culture dish, make the about 0.5cm of bacteria suspension thick, put into aseptic magnetic stir bar, put on the magnetic stirring apparatus, 30cm place under the ultraviolet lamp, with 30W ultra violet lamp 5min, get the dilution of mutagenic treatment bacteria suspension and be coated with flat board, picking list bacterium colony carries out the test of isomerization ability respectively, the positive mutating strain that screening isomerization ability improves, and repeatedly go down to posterity, the 1 strain isomerization level that screens in the bacterial strain of reverse mutation never takes place improve 13% mutant strain.
Embodiment 5
Be rich in 9c, the production of 11t-CLA sour milk
In fresh milk, add milk powder, be configured to solid content and be 10% emulsion, filtering and impurity removing is preheated to 55-60 ℃, homogeneous under 10-15Mpa pressure, emulsion is heated to 90-95 ℃, keep 5-10min, after the pasteurize emulsion is cooled to 40-45 ℃, add 0.2% linolic acid, with mixed culture fermentation agent (lactobacillus bulgaricus: thermophilus streptococcus: lactobacillus acidophil-aerogenes=1: 1: 1) join in the emulsion, stir by 5%.
5.1 the production of solidification type yoghourt
The emulsion of above-mentioned mixing divided install in vial or the Plastic Bottle under aseptic condition, seal, cultivate 4-5h down, treat that acidity reaches 60-70 ° of T, stop cultivating, it is sent in the 0-5 ℃ of freezer storage 12-14h at 42 ℃.
5.2 the production of stirred yogurt
The emulsion of above-mentioned mixing is cultivated 4-5h down at 42 ℃, treat that acidity reaches 60-70 ° of T, stop cultivating, it is sent in the 0-5 ℃ of freezer, storage 12-14h adds the sour milk that fruit juice, sucrose etc. are deployed into various local flavors.
Contain 50mg9c by every 100g sour milk in the product of this method production, 11t-CLA, its content is significantly higher than common sour milk.
Claims (1)
1. method for preparing conjugated fatty acids, it is characterized in that: the specific isomerase of utilizing lactobacterium casei cheese subspecies (being numbered CGMCCl.574) to produce, with 9c, 12c unsaturated fatty acids biology is isomerizated into single 9c, 11t conjugated fatty acids isomer, described 9c, 11t conjugated fatty acids are 9c, 11t conjugated linolic acid or 9c, the 11t conjugate linolenic acid.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104480150A (en) * | 2014-11-04 | 2015-04-01 | 南昌大学 | Biological enrichment method of conjugated linolenic acid isomer |
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| CN100396781C (en) * | 2005-11-07 | 2008-06-25 | 浙江工商大学 | Process of preparing conjugate linolic acid with lactic acid bacteria |
| CN102559532B (en) * | 2010-12-13 | 2013-09-04 | 北京农业生物技术研究中心 | Strain for producing conjugated linoleic acid and application thereof |
| CN105039442B (en) * | 2015-07-20 | 2018-03-02 | 南昌大学 | The method of biosynthesis conjugation alpha linolenic acid isomers in organic media |
| CN105087692B (en) * | 2015-07-20 | 2018-04-17 | 南昌大学 | The method that surfactant coating thalline catalyzes and synthesizes conjugation alpha linolenic acid isomers |
| CN105087691B (en) * | 2015-07-20 | 2018-04-17 | 南昌大学 | The method that surfactant coating thalline catalyzes and synthesizes conjugated linoleic acid isomers |
| CN105039440B (en) * | 2015-07-20 | 2018-06-08 | 南昌大学 | It is coated the method for thalline biosynthesis conjugation alpha-linolenic acid isomers in organic media |
| CN105039438B (en) * | 2015-07-20 | 2018-05-22 | 南昌大学 | It is conjugated the non-aqueous enzymatic synthesis of gamma-Linolenic acid isomers |
| CN105112461B (en) * | 2015-07-20 | 2018-04-17 | 南昌大学 | It is coated the method for thalline biosynthesis conjugation acid and gamma-linolenic isomers in organic media |
| CN105039441B (en) * | 2015-07-20 | 2018-03-02 | 南昌大学 | It is conjugated the non-aqueous enzymatic synthesis of alpha linolenic acid isomers |
| CN105039443B (en) * | 2015-07-20 | 2018-05-22 | 南昌大学 | The method of biosynthesis conjugation gamma-Linolenic acid isomers in organic media |
| CN105087693B (en) * | 2015-07-20 | 2018-04-17 | 南昌大学 | The method that surfactant coating thalline catalyzes and synthesizes conjugation acid and gamma-linolenic isomers |
| CN109576020B (en) * | 2017-09-28 | 2021-02-05 | 中国石油化工股份有限公司 | Method for synthesizing low-sulfur diesel lubricity improver in ionic liquid |
| CN111349663B (en) * | 2018-12-21 | 2023-02-03 | 中国石油化工股份有限公司 | Modification method and application of vegetable oil fatty acid methyl ester |
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| US6060304A (en) * | 1995-06-01 | 2000-05-09 | Wisconsin Alumni Research Foundation | Method of producing conjugated fatty acids |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104480150A (en) * | 2014-11-04 | 2015-04-01 | 南昌大学 | Biological enrichment method of conjugated linolenic acid isomer |
| CN104480150B (en) * | 2014-11-04 | 2017-08-25 | 南昌大学 | A kind of biological concentration method of conjugate linolenic acid isomers |
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