CN105087693B - The method that surfactant coating thalline catalyzes and synthesizes conjugation acid and gamma-linolenic isomers - Google Patents
The method that surfactant coating thalline catalyzes and synthesizes conjugation acid and gamma-linolenic isomers Download PDFInfo
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Abstract
The method that surfactant coating thalline catalyzes and synthesizes conjugation acid and gamma-linolenic isomers, comprises the following steps：（1）Every gram of 1.574 thalline of Lactobacillus casei CGMCC is resuspended in 5mL permeabilized treatment liquid, 37 DEG C of processing 20min, are collected by centrifugation permeability thalline；（2）After being washed with the phosphate buffer of 60mM, pH5.8, thalline is collected by centrifugation, every gram of wet thallus is resuspended in the phosphate buffer of 20mL60mM, pH5.8, the acetone soln of double oleyl alcohol ester ribitol containing 1% glutamic acid is added dropwise again, side edged mixes, 4 40 DEG C of 2 6h of processing, are collected by centrifugation thalline, thalline must be coated after freeze-drying；（3）Every gram of freeze-dried coated thalline is added in 500mL n-hexanes, is stirred evenly, the acid and gamma-linolenic of n-hexane percent by volume 0.1 0.3% is added, reacts 1 12h at 4 40 DEG C；（4）Coating thalline is centrifuged, recycles n-hexane, product isc6,c9,t11 conjugation acid and gamma-linolenic isomers.Reaction time of the invention is short, and coating thalline is reusable repeatedly, and yield is significantly improved, and non-environmental-pollution, significantly reduces production cost.
Description
Technical field
The invention belongs to biomedicine technical field.
Background technology
Conjugation gamma-Linolenic acid is the conjugated isomers of gamma-Linolenic acid, is the general designation of one group of eighteen carbon conjugated trienoic acid, has
A variety of position isomeries and geometric isomer, such as：c6,c9,t11- be conjugated gamma-Linolenic acid andc6,t10,c12- is conjugated gamma-Linolenic acid
Isomers etc..Research shows that being conjugated gamma-Linolenic acid has the physiological functions such as anticancer, prevention of arterial atherosis, weight-reducing, and it is given birth to
Reason activity has isomers specificity, such as：c6,c9,t11- conjugation gamma-Linolenic acid isomers has the function that anticancer.In nature
In boundary, conjugation gamma-Linolenic acid be primarily present in the milk of ruminant and the fat of meat, mainly byc6,c9,t11- conjugation γ-
The isomers such as leukotrienes are formed, but its content is usually very low, can not meet the development and application for the purpose of health care and medical treatment.
There is presently no conjugation gamma-Linolenic acid preparation method report, people simply to microbial fermentation synthesis of conjugate α-
Leukotrienes has carried out some researchs.At present, microbial fermentation carries out in aqueous, due to fermentation substrate-gamma-Linolenic acid
It is liposoluble substance, therefore is needed before gamma-Linolenic acid addition zymotic fluid through emulsification treatment, and additive amount is restricted, and will be from hair
Conjugation gamma-Linolenic acid product is obtained in zymotic fluid to be extracted through organic solvent, whole production technology there are fermentation period it is long, be produced into
The shortcomings that this height, low output.
The content of the invention
The purpose of the present invention is in view of the deficiencies of the prior art, propose that a kind of surfactant coating thalline catalyzes and synthesizes altogether
The method of yoke gamma-Linolenic acid isomers, significantly shortens generated time, improves yield and conversion ratio, reduces production cost.
The present invention comprises the following steps.
（1）The permeabilized treatment of thalline：Collect the Lactobacillus casei in exponential phase（Lactobacillus casei）1.574 thalline of CGMCC, are resuspended in 5mL permeabilized treatment liquid by every gram of wet thallus and fall into a trap, wet thallus is resuspended in
In property treatment fluid（The triton x-100 of permeabilized treatment liquid 0.5-3.0% containing percent by volume, 20-200mM,
The phosphate buffer of pH5.8）, thalline is resuspended through 37 DEG C of processing 20min, permeability thalline is collected by centrifugation.
（2）Thalline Cotton seeds：After permeability thalline is washed with the phosphate buffer of 60mM, pH5.8, bacterium is collected by centrifugation
Body, the phosphate buffer that 20mL60mM, pH5.8 are resuspended in by every gram of wet thallus are fallen into a trap, and permeability wet thallus is resuspended in phosphorus
In phthalate buffer, then surfactant solution is added dropwise thereto（The surfactant solution is containing mass percent 1%
The acetone soln of the double oleyl alcohol ester ribitol of glutamic acid）, side edged is uniformly mixed, and handles 2-6h in 4-40 DEG C, thalline is collected by centrifugation,
Coating thalline is obtained after thalline is freeze-dried.
（3）Catalyze and synthesize：500mL n-hexanes are added to by every gram of freeze-dried coated thalline to fall into a trap, and coating thalline is added to
In n-hexane, stir evenly, add the gamma-Linolenic acid of n-hexane percent by volume 0.1-0.3%, react 1- at 4-40 DEG C
12h。
（4）Collection of products：Coating thalline is centrifuged, hexane solution is evaporated under reduced pressure, recycles n-hexane, product
Forc6,c9,t11- is conjugated gamma-Linolenic acid isomers.
Step of the present invention（1）Middle permeabilized treatment liquid is preferably that the Qula of the 1.0-2.0% containing percent by volume leads to X-
100,30-100mM, the phosphate buffer of pH5.8.
Step of the present invention（2）The dripping quantity of middle surfactant solution is preferably to add 5- per 50mL bacteria suspensions
15mL surfactant solutions.
Step of the present invention（2）Middle treatment temperature is preferably 4-25 DEG C.
Step of the present invention（2）Middle processing time is preferably 3-5h.
Step of the present invention（3）In be preferably added to the gamma-Linolenic acid of n-hexane percent by volume 0.125-0.25%,
2-6h is reacted at 15-30 DEG C.
Step of the present invention（4）Middle coating thalline can be repeated for catalyzing and synthesizingc6,c9,t11- is conjugated γ-flax
Acid isomer.
Lactobacillus casei used in the present invention（Lactobacillus casei）CGMCC 1.574, is Chinese common micro- life
Thing culture presevation administrative center（CGMCC）Preservation strain, numbering 1.574, the bacterial strain can produce specific linoleic acid isomery
Enzyme, can be by polyunsaturated fatty acidc9,c12 double-bond isomerisms intoc9,t11 conjugated double bonds, by biological isomerization can by γ-
Leukotrienes（c6,c9,c12-18:3）Changing at 268nm has the novel substance of characteristic absorption peak, and absworption peak is altogether at 268nm
The characteristic peak of yoke triolefin, shows that the bacterium can change into gamma-Linolenic acidc6,c9,t11- is conjugated gamma-Linolenic acid isomers.At present,
The isomerase sterling of definite catalytic activity is not separated to from the bacterium also.Therefore, which is probably by multienzyme
System co-catalysis is completed.
By coating thalline process for catalytic synthesis in organic media, with optimal conditions, containing percent by volume 0.15%
It is synthesized after the hexane solution reaction of gamma-Linolenic acidc6,c9,tThe content of 11- conjugation gamma-Linolenic acid isomers is volume hundred
Divide ratio 0.14%, the conversion ratio of gamma-Linolenic acid is 93.3%.Step of the present invention（4）Middle coating thalline can be repeated for walking
Suddenly（3）Catalyze and synthesizec6,c9,t11- is conjugated gamma-Linolenic acid isomers, and after coating thalline is reused five times, it, which is catalyzed, lives
Property is still greater than 90%.
Carried out in aqueous for existing microbial fermentation synthesis of conjugate gamma-Linolenic acid, whole production technology exists
Fermentation period is grown, and extraction conjugation gamma-Linolenic acid product is difficult from zymotic fluid, and thalline cannot be reused, and production cost is high, production
Measure low shortcomings.The present invention is proposed catalyzes and synthesizes conjugation in organic media by microbial cells by gamma-Linolenic acid
The new method of gamma-Linolenic acid.This method handles Lactobacillus casei CGMCC 1.574 by triton x-100 first, is keeping bacterium
While body integrality, somatic cells wall and membrane passage are improved, on the one hand may insure in follow-up Cotton seeds
Intracellular linoleate isomerase surface energy forms complete coatings, on the other hand can improve reaction substrate gamma-Linolenic acid and
The speed of product conjugation gamma-Linolenic acid disengaging thalline, reduces the inhibitory action of high concentration substrate and product to catalytic reaction, significantly
Shorten the reaction time.
The present invention selects the double oleyl alcohol ester ribitol of glutamic acid to be coated thalline, the double oleyl alcohol ester ribitol molecules of glutamic acid
In contain 2 oleyl alcohol groups, oleyl alcohol is the analogue of thalline Linoleic acid isomery zymolyte, can be when thalline is coated
The catalytic active center of enzyme forms molecular engram, makes thalline catalytic active center conformation of enzyme after freeze-drying constant, can be
Higher catalytic activity is kept in organic solvent.Meanwhile the present invention be incorporated in thalline Cotton seeds during select suitable phosphorus
The double oleyl alcohol ester ribose determining alcohols of phthalate buffer, glutamic acid and coating temperature, time, make gained coating thalline in organic media
Still there is higher catalytic capability.The heat endurance of enzyme improves in thalline after coating, and the every batch of reaction time only needs 4h, is much smaller than
Time a couple of days in traditional aqueous needed for Batch fermentation.
Gained coating thalline of the invention has higher catalytic activity in n-hexane, only need to centrifuge coating thalline, will just
Hexane solution is evaporated under reduced pressure, and recycles n-hexane, you can obtain productc6,c9,t11- is conjugated gamma-Linolenic acid.Centrifugation gained
Coating thalline can be repeated several times for biosynthesis in organic mediac6,c9,t11- is conjugated gamma-Linolenic acid isomers, significantly contracting
The short production time, yield is improved, reduces production cost.In addition, n-hexane is that edible oil and fat industry is common organic molten
Agent, this guarantees obtained by the present inventionc6,c9,t11- is conjugated the safety in utilization of gamma-Linolenic acid.
The present invention has the following advantages that compared with prior art.
The present invention is directly coated thalline processing, is used for catalytic reaction as immobilised enzymes, on the one hand reduces enzyme
The cost isolated and purified, avoids the loss of enzyme activity in extraction；On the other hand multi-enzyme system can be wrapped together, made whole
A reaction process is smooth；Furthermore it is coated thalli granule and is more than coating enzyme, is easy to separate from reaction solution, and
Filtration resistance is smaller, and therefore, coating thalline is more suitable for the column reactor for successive reaction.
The present invention carries out catalytic reaction by being coated thalline in organic media, avoids in traditional aqueous reaction system
Middle substrate gamma-Linolenic acid solubility is low and product conjugation gamma-Linolenic acid extracts the problem of difficult.It is coated the thermostabilization of enzyme in thalline
Property improve, the every batch of reaction time only needs 4h, much smaller than time a couple of days for fermenting required in traditional aqueous.Coating thalline can weigh
It is multiple to use repeatedly, product yield, and non-environmental-pollution are significantly improved, production cost can be significantly reduced；And traditional aqueous system
Thalline in zymotic fluid is used only once, and production cost is high, and Wastewater treating is costly, environment easy to pollute.
Embodiment
The present invention is further described by following embodiments.
Embodiment 1.
By the Lactobacillus casei of activation（Lactobacillus casei）1.574 strains of CGMCC are inoculated into MRS culture mediums
In, 20h is cultivated at 30 DEG C, 5000g centrifugations 10min collects thalline, 10 grams of wet thallus are resuspended in 50mL and contain percent by volume
1.5% triton x-100 and 50mM phosphate buffers（pH5.8）Permeabilized treatment liquid in, 37 DEG C of water bath processing 20min,
5000g centrifugations 10min obtains permeability thalline.
Permeability thalline 50mL60mM phosphate buffers（pH5.8）After washing, 6000g centrifugations 10min collects thalline,
Wet thallus is resuspended in 200mL60mM phosphate buffers（pH5.8）In, 40mL mass percents are slowly added dropwise thereto as 1%
The double oleyl alcohol ester ribitol of glutamic acid（Song Baodong etc., petrochemical industry, the supplementary issues of volume 2001,30：376-378）Acetone soln, mix
Closing uniformly, thalline are collected in 4 DEG C of stir process 4h, 6000g centrifugation 10min, thalline is freeze-dried after -80 DEG C of pre-freezes,
Obtain coating thalline.
1 gram of freeze-dried coated thalline is added in 500mL n-hexanes, is stirred evenly, adds 0.75mL gamma-Linolenic acids,
Stirring reaction 4h at 25 DEG C.6000g centrifuges coating thalline, and hexane solution is evaporated under reduced pressure at 40 DEG C, and recycling is just
Hexane, obtains 0.75mL products, whereinc6,c9,tThe content of 11- conjugation gamma-Linolenic acids is 93.3%.The coating bacterium that will be collected into
Body is recycled and reused for above-mentioned synthetic reaction, when being used continuously five times in productc6,c9,t11- conjugation gamma-Linolenic acid content be
90.9%。
Embodiment 2.
By the Lactobacillus casei of activation（Lactobacillus casei）1.574 strains of CGMCC are inoculated into MRS culture mediums
In, 18h is cultivated at 30 DEG C, 4000g centrifugations 5min collects thalline, 10 grams of wet thallus are resuspended in 50mL and contain percent by volume
3.0% triton x-100 and 200mM phosphate buffers（pH5.8）Permeabilized treatment liquid in, 37 DEG C of water bath processings
20min, 5000g centrifugation 10min obtain permeability thalline.
Permeability thalline 40mL60mM phosphate buffers（pH5.8）After washing, 5000g centrifugations 10min collects thalline,
Wet thallus is resuspended in 200mL60mM phosphate buffers（pH5.8）In, 40mL mass percents are slowly added dropwise thereto as 1%
The double oleyl alcohol ester ribitol of glutamic acid acetone soln, be uniformly mixed, bacterium collected in 4 DEG C of stir process 2h, 6000g centrifugation 5min
Body, thalline are freeze-dried after -80 DEG C of pre-freezes, obtain coating thalline.
1 gram of freeze-dried coated thalline is added in 500mL n-hexanes, is stirred evenly, 1.5mL gamma-Linolenic acids are added, 40
Stirring reaction 12h at DEG C.6000g centrifuge coating thalline, hexane solution is evaporated under reduced pressure at 40 DEG C, recycling just oneself
Alkane, obtains 1.5mL products, whereinc6,c9,tThe content of 11- conjugation gamma-Linolenic acids is 82.4%.The coating thalline that will be collected into
Above-mentioned synthetic reaction is recycled and reused for, when being used continuously five times in productc6,c9,t11- conjugation gamma-Linolenic acid content be
72.5%。
Embodiment 3.
By the Lactobacillus casei of activation（Lactobacillus casei）1.574 strains of CGMCC are inoculated into MRS culture mediums
In, 18h is cultivated at 30 DEG C, 4000g centrifugations 5min collects thalline, 10 grams of wet thallus are resuspended in 50mL and contain percent by volume
0.5% triton x-100 and 20mM phosphate buffers（pH5.8）Permeabilized treatment liquid in, 37 DEG C of water bath processing 20min,
5000g centrifugations 10min obtains permeability thalline.
Permeability thalline 50mL60mM phosphate buffers（pH5.8）After washing, 4000g centrifugations 10min collects thalline,
Wet thallus is resuspended in 200mL60mM phosphate buffers（pH5.8）In, 40mL mass percents are slowly added dropwise thereto as 1%
The double oleyl alcohol ester ribitol of glutamic acid acetone soln, be uniformly mixed, bacterium collected in 4 DEG C of stir process 6h, 5000g centrifugation 5min
Body, thalline are freeze-dried after -80 DEG C of pre-freezes, obtain coating thalline.
1 gram of freeze-dried coated thalline is added in 500mL n-hexanes, is stirred evenly, 0.5mL gamma-Linolenic acids are added, 4
Stirring reaction 6h at DEG C.6000g centrifuge coating thalline, hexane solution is evaporated under reduced pressure at 40 DEG C, recycling just oneself
Alkane, obtains 0.5mL products, whereinc6,c9,tThe content of 11- conjugation gamma-Linolenic acids is 91.2%.The coating thalline that will be collected into
Above-mentioned synthetic reaction is recycled and reused for, when being used continuously five times in productc6,c9,t11- conjugation gamma-Linolenic acid content be
83.7%。
Embodiment 4.
By the Lactobacillus casei of activation（Lactobacillus casei）1.574 strains of CGMCC are inoculated into MRS culture mediums
In, 20h is cultivated at 30 DEG C, 5000g centrifugations 10min collects thalline, 10 grams of wet thallus are resuspended in 50mL and contain percent by volume
1.5% triton x-100 and 50mM phosphate buffers（pH5.8）Permeabilized treatment liquid in, 37 DEG C of water bath processing 20min,
5000g centrifugations 10min obtains permeability thalline.
Permeability thalline 50mL60mM phosphate buffers（pH5.8）After washing, 6000g centrifugations 10min collects thalline,
Wet thallus is resuspended in 200mL60mM phosphate buffers（pH5.8）In, 40mL mass percents are slowly added dropwise thereto as 1%
The double oleyl alcohol ester ribitol of glutamic acid acetone soln, be uniformly mixed, collected in 4 DEG C of stir process 4h, 6000g centrifugation 10min
Thalline, thalline are freeze-dried after -80 DEG C of pre-freezes, obtain coating thalline.
1 gram of freeze-dried coated thalline is fitted into pillar bioreactor, 0.75mL gamma-Linolenic acids are being added to 250mL just
Mixed in hexane, the hexane solution containing gamma-Linolenic acid is injected into reactor by pumping, flow 3mL/min, collects outflow
Liquid, reactor is repeatedly injected 2 times by efflux, is collected efflux, is evaporated under reduced pressure at 40 DEG C, is recycled n-hexane, is obtained
0.75mL products, whereinc6,c9,tThe content of 11- conjugation gamma-Linolenic acids is 91.2%.By by several pillar bioreactors
It is cascaded, it is possible to achieve continuous production.
Claims (6)
1. the method that surfactant coating thalline catalyzes and synthesizes conjugation gamma-Linolenic acid isomers, it is characterized in that including following step
Suddenly：
（1）Collect the Lactobacillus casei in exponential phase（Lactobacillus casei）1.574 thalline of CGMCC, are pressed
Every gram of wet thallus is resuspended in 5mL permeabilized treatment liquid and falls into a trap, and wet thallus is resuspended in permeabilized treatment liquid, and thalline is resuspended through 37
DEG C processing 20min, permeability thalline is collected by centrifugation；
（2）After permeability thalline is washed with the phosphate buffer of 60mM, pH5.8, thalline is collected by centrifugation, by every gram of wet thallus weight
The phosphate buffer for being suspended from 20mL60mM, pH5.8 is fallen into a trap, and permeability wet thallus is resuspended in phosphate buffer, then to
Surfactant is wherein added dropwise, side edged is uniformly mixed, and handles 2-6h in 4-40 DEG C, thalline is collected by centrifugation, and thalline is freezed dry
Coating thalline is obtained after dry；
（3）500mL n-hexanes are added to by every gram of freeze-dried coated thalline to fall into a trap, and coating thalline is added in n-hexane, is stirred
Uniformly, the gamma-Linolenic acid of n-hexane percent by volume 0.1-0.3% is added, reacts 1-12h at 4-40 DEG C；
（4）Coating thalline is centrifuged, hexane solution is evaporated under reduced pressure, recycles n-hexane, product isc6,c9,t11-
It is conjugated gamma-Linolenic acid isomers；
Step（1）The triton x-100 of permeabilized treatment liquid 0.5-3.0% containing percent by volume, 20-200mM, pH5.8
Phosphate buffer；
Step（2）The surfactant is the acetone soln of double oleyl alcohol ester ribitol containing 1% glutamic acid of mass percent.
2. the method that surfactant coating thalline according to claim 1 catalyzes and synthesizes conjugation gamma-Linolenic acid isomers,
It is characterized in that the step（1）Middle permeabilized treatment liquid be the 1.0-2.0% containing percent by volume triton x-100,30-
The phosphate buffer of 100mM, pH5.8.
3. the method that surfactant coating thalline according to claim 1 catalyzes and synthesizes conjugation gamma-Linolenic acid isomers,
It is characterized in that the step（2）The dripping quantity of middle surfactant is to add 5-15mL surfactants per 50mL bacteria suspensions.
4. the method that surfactant coating thalline according to claim 1 catalyzes and synthesizes conjugation gamma-Linolenic acid isomers,
It is characterized in that the step（2）Middle treatment temperature is 4-25 DEG C.
5. the method that surfactant coating thalline according to claim 1 catalyzes and synthesizes conjugation gamma-Linolenic acid isomers,
It is characterized in that the step（2）Middle processing time is 3-5h.
6. the method that surfactant coating thalline according to claim 1 catalyzes and synthesizes conjugation gamma-Linolenic acid isomers,
It is characterized in that the step（3）The middle gamma-Linolenic acid for adding n-hexane percent by volume 0.125-0.25%, at 15-30 DEG C
React 2-6h.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1629302A (en) * | 2004-07-28 | 2005-06-22 | 南昌大学 | Process for preparing conjugated fatty acid |
| CN104404092A (en) * | 2014-11-04 | 2015-03-11 | 南昌大学 | Conjugated linoleic acid isomer biological enrichment method |
| CN104480150A (en) * | 2014-11-04 | 2015-04-01 | 南昌大学 | Biological enrichment method of conjugated linolenic acid isomer |
-
2015
- 2015-07-20 CN CN201510423963.7A patent/CN105087693B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1629302A (en) * | 2004-07-28 | 2005-06-22 | 南昌大学 | Process for preparing conjugated fatty acid |
| CN104404092A (en) * | 2014-11-04 | 2015-03-11 | 南昌大学 | Conjugated linoleic acid isomer biological enrichment method |
| CN104480150A (en) * | 2014-11-04 | 2015-04-01 | 南昌大学 | Biological enrichment method of conjugated linolenic acid isomer |
Non-Patent Citations (5)
| Title |
|---|
| Microbial production of conjugated γ-linolenic acid from γ-linolenic acid by Lactobacillus plantarum AKU 1009a;S.Kishino等;《Journal of Applied Microbiology》;20100507;第108卷(第6期);第2012-2018页 * |
| Production of conjugated fatty acids by lactic acid bacteria;Jun Ogawa等;《Journal of Bioscience and Bioengineering》;20051031;第100卷(第4期);第355-364页 * |
| 共轭亚麻酸的制备、表征和生物活性研究进展;高红丽等;《化学通报》;20070228(第2期);第96-105页 * |
| 谷氨酸二烷酯核糖醇的合成及应用;宋宝东等;《石油化工》;20011001;第30卷;第376-378页 * |
| 透性化细胞制备方法的研究进展;刘晓华等;《食品工业科技》;20111130;第32卷(第11期);第475-479页 * |
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