CN105648002A - Method for extracting dipeptide cyclo(Gly-Tyr) from bacillus coagulans - Google Patents
Method for extracting dipeptide cyclo(Gly-Tyr) from bacillus coagulans Download PDFInfo
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- CN105648002A CN105648002A CN201610113919.0A CN201610113919A CN105648002A CN 105648002 A CN105648002 A CN 105648002A CN 201610113919 A CN201610113919 A CN 201610113919A CN 105648002 A CN105648002 A CN 105648002A
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- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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Abstract
The invention discloses a method for extracting dipeptide cyclo(Gly-Tyr) from bacillus coagulans. A method for preparing dipeptide cyclo(Gly-Tyr) mainly comprises steps as follows: activating and culturing bacteria, acquiring a crude extract, performing course separation on the crude extract through silica gel column chromatography, fine separation through gel column chromatography and further purification through HPLC, performing TLC tracking and detection and identifying an acquired compound to be dipeptide cyclo(Gly-Tyr) through nuclear magnetic detection and comparison with literature. The raw material bacillus coagulans is a probiotic and is safe and harmless, and an extraction process is simple and low in cost; the prepared compound has high purity.
Description
Technical field
The invention belongs to the preparing technical field of ring (sweet-cheese) dipeptides, be specifically related to a kind of method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans.
Background technology
Bacillus coagulans (bacilluscoagulansLL1103), also known as lactic acid bacteria, had both had the characteristic of lactic acid bacteria lactic acid producing, had again abundant enzyme system and strong stress resistance, high temperature resistant, bile tolerance, the easy characteristic stored of bacillus cereus. As the up-and-coming youngster of probiotic bacteria family, be made into microbial ecological agent oneself be widely used in aquaculture, the industries such as material, food and medicine are watched in herding. Bacillus coagulans is except the health-care effect in maintaining intestinal microecology balance, and common intestinal tract disease such as chronic colitis, diarrhoea and constipation etc. are had obvious curative effects by it, also has and regulates blood pressure and blood lipoid and improve effect of immunity.
Research shows have the polypeptides matter bacteriocin suppressing putrefaction bacteria and pathogenic bacterium in Bacillus coagulans metabolite, produces the report of anti-plant pathogenic fungi in recent years also on Bacillus coagulans. But Bacillus coagulans metabolite but has no the report of small-molecule substance CYCLIC DIPEPTIDES compounds; Cyclic dipeptides is a kind of diketopiperazines material with stable six-membered ring structure, shows multiple biological activity and the pharmacologically actives such as antibacterium, antifungal, antiviral, antitumor, immunosuppressant, neuroprotective, hyperglycemia, malaria.
Summary of the invention
It is an object of the invention to provide the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans that a kind of preparation technology ring (sweet-cheese) dipeptides purity simple, that prepare is high.
For achieving the above object, the technical solution used in the present invention is, a kind of method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans, and the structural formula of ring (sweet-cheese) dipeptides is as follows:
;
Said method comprising the steps of:
(1) actication of culture: be inoculated on plating medium by Bacillus coagulans, cultivates 24 hours under 37 DEG C of conditions, it is thus achieved that activated spawn;
(2) primary cultivation: the activated spawn obtained in step (1) is inoculated in MRS fluid medium, at 150r/min, under 37 DEG C of conditions, shaking table is cultivated 12��16 hours, obtains seed liquor;
(3) secondary cultivation: being inoculated in MRS fluid medium by the seed liquor that step (2) obtains, the volume of seed liquor is the 4��6% of MRS fluid medium volume, at 150r/min, under 37 DEG C of conditions, fermentation liquid cultivated 48��72 hours to obtain by shaking table;
(4) prepared by crude extract: fermentation liquid concentrated by rotary evaporation step (3) prepared is centrifugal to the 1/4 of original volume, take supernatant ethanol to precipitate, filter and continue to concentrate the filtrate to the 1/4 of original volume, then it is extracted with ethyl acetate, aqueous phase n-butyl alcohol is extracted again, butanol extraction liquid concentrating under reduced pressure is obtained crude extract;
(5) silica gel column chromatography rough segmentation: crude extract methanol prepared by step (4) is dissolved then dress post after silica gel mixed sample, fixing is the silica gel of 80-100 order mutually, with dichloromethane: methanol volume ratio=50:1��1:1 gradient elution, silica gel thin-layer chromatography detects, and the volume ratio of combined dichloromethane-methanol is stream part of 10:1;
(6) by stream part of obtaining in above-mentioned steps (5) through SephadexLH-20 gel filtration chromatography eluting, using dichloromethane: methanol=1:1 is as mobile phase, and through silica gel thin-layer chromatography combining data detection same stream part, it is thus achieved that 3 stream parts;
(7) the 3rd stream part reversed-phase high-performance liquid chromatography purification step (5) obtained, with acetonitrile-water mobile phase, eluent concentrating under reduced pressure removes acetonitrile and water, dry, obtains ring (sweet-cheese) dipeptides.
The formula of described plating medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, agar 15.0g/L, tween 80 1.0mL/L, pH6.0.
The formula of described MRS fluid medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, tween 80 1.0mL/L, pH6.0.
In described step (4), after fermentation liquid concentrated by rotary evaporation, the process conditions of centrifugation are: centrifugal condition is temperature 4 DEG C, and rotating speed is 5000rpm, centrifugation time 20min.
The concrete operations of described step (4) supernatant ethanol precipitation are: add the ethanol of isopyknic 95% in supernatant.
The concrete operations that after concentration, filtrate is extracted with ethyl acetate in described step (4) are: filtrate and ethyl acetate 11 will mix by volume after concentration, and pour in separatory funnel, and shaking flask extraction 2 ~ 3 times stands 20��30min every time, obtains aqueous phase; The concrete operations of the aqueous phase n-butanol extraction that extraction into ethyl acetate obtains are: aqueous phase and n-butyl alcohol 11 mix by volume, pour in separatory funnel, and shaking flask extracts 2 ~ 3 times, stands 20��30min every time, obtains butanol extraction liquid.
Preferably, the reversed-phase high-performance liquid chromatography condition in described step (7) is:
Chromatographic column: Agilent pursuitC18,10 ��m, 150 �� 21.2mm (I.D);
Mobile phase consists of acetonitrile: water=5: 95-50: 50;
Flow velocity: 15ml/min;
Column temperature: 25 DEG C;
Detection wavelength: 230,254nm;
Sample size: 300-500 �� l.
The beneficial effect comprise that: the present invention carries out the extraction of ring (sweet-cheese) dipeptides with Bacillus coagulans for raw material, Bacillus coagulans is a kind of probiotic bacteria, its metabolite has natural sex safety, and extracting method is simple, cost is low, there is sustainability, ring (sweet-cheese) the dipeptides purity prepared high (up to 99%), to promoting that ring (sweet-cheese) dipeptides pharmacology studies and significant as lead compound development and utilization further.
Accompanying drawing explanation
Fig. 1 is ring (sweet-cheese) dipeptides of embodiment 1 preparation1HNMR schemes;
Fig. 2 is ring (sweet-cheese) dipeptides of embodiment 1 preparation13CNMR schemes.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to this. Bacillus coagulans used in following example derives from China typical culture collection center (deposit number: CCTCCNO:M2013193).
Embodiment 1
A kind of method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans, comprises the following steps:
(1) actication of culture: be inoculated on plating medium by Bacillus coagulans, cultivates 24 hours under 37 DEG C of conditions, it is thus achieved that activated spawn;
(2) primary cultivation: the activated spawn obtained in step (1) is inoculated in MRS fluid medium, at 150r/min, under 37 DEG C of conditions, shaking table is cultivated 12 hours, obtains seed liquor;
(3) secondary cultivation: being inoculated in MRS fluid medium by the seed liquor that step (2) obtains, the volume of seed liquor is the 4% of MRS fluid medium volume, at 150r/min, under 37 DEG C of conditions, fermentation liquid cultivated 48 hours to obtain by shaking table;
(4) prepared by crude extract: fermentation liquid concentrated by rotary evaporation step (3) prepared is centrifugal to the 1/4 of original volume, take supernatant ethanol to precipitate, filter and continue to concentrate the filtrate to the 1/4 of original volume, then it is extracted with ethyl acetate, aqueous phase n-butyl alcohol is extracted again, butanol extraction liquid concentrating under reduced pressure is obtained crude extract;
(5) silica gel column chromatography rough segmentation: crude extract methanol prepared by step (4) is dissolved then dress post after silica gel mixed sample, fixing is the silica gel of 80-100 order mutually, with dichloromethane: methanol volume ratio=50:1��1:1 gradient elution (dichloromethane: methanol volume ratio is for 50:1,40:1,30:1,20:1,10:1,1:1), silica gel thin-layer chromatography detects, and collects stream part that volume ratio is 10:1 of methylene chloride-methanol;
(6) by stream part of obtaining in above-mentioned steps (5) through SephadexLH-20 gel filtration chromatography eluting, using dichloromethane: methanol=1:1 is as mobile phase, and through silica gel thin-layer chromatography combining data detection same stream part, it is thus achieved that 3 stream parts;
(7) the 3rd stream part step (5) obtained is with acetonitrile-water for eluant reversed-phase high-performance liquid chromatography purification, and reversed-phase high-performance liquid chromatography condition is:
Chromatographic column: Agilent pursuitC18,10 ��m, 150 �� 21.2mm (I.D);
Mobile phase consists of acetonitrile: water=5: 95-50: 50(in 10min the volume ratio of acetonitrile and water be progressively transitioned into 50: 50 from 5: 95);
Flow velocity: 15ml/min;
Column temperature: 25 DEG C;
Detection wavelength: 230,254nm;
Sample size: 300 �� l;
Elution time is 15min;
Eluent concentrating under reduced pressure removes acetonitrile and water, dry, obtains ring (sweet-cheese) dipeptides (purity 99.1%).
The formula of described plating medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, agar 15.0g/L, tween 80 1.0mL/L, pH6.0.
The formula of described MRS fluid medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, tween 80 1.0mL/L, pH6.0.
In described step (4), after fermentation liquid concentrated by rotary evaporation, the process conditions of centrifugation are: centrifugal condition is temperature 4 DEG C, and rotating speed is 5000rpm, centrifugation time 20min.
The concrete operations of described step (4) supernatant ethanol precipitation are: add the ethanol of isopyknic 95% in supernatant.
The concrete operations that after concentration, filtrate is extracted with ethyl acetate in described step (4) are: filtrate and ethyl acetate 11 will mix by volume after concentration, and pour in separatory funnel, and shaking flask extraction 2 times stands 30min every time, obtains aqueous phase; Extraction into ethyl acetate obtains the concrete operations of aqueous phase n-butanol extraction: aqueous phase and n-butyl alcohol 11 mix by volume, pour in separatory funnel, and shaking flask extracts 2 times, stands 30min every time, obtains butanol extraction liquid.
By Fig. 1-2 it can be seen that warp1HNMR��13CNMR analyzes, comparison document (Guo Qiong, Wang Jian, Yao Junhua, etc. strain South Sea Corallium Japonicum Kishinouye antibacterial L-4 anti-tumor activity secondary metabolite research [J]. Zhongshan University's journal, 2013,52 (3): 77-82.), confirm that the compound extracted is ring (sweet-cheese) dipeptides��
Above-described embodiment is the preferred embodiment of the present invention, but embodiments of the present invention being not restricted to the described embodiments, other any change made without departing from the present invention all should be the substitute mode of equivalence, is included within protection scope of the present invention.
Claims (7)
1. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans, the structural formula of ring (sweet-cheese) dipeptides is as follows:
;
It is characterized in that, said method comprising the steps of:
(1) actication of culture: be inoculated on plating medium by Bacillus coagulans, cultivates 24 hours under 37 DEG C of conditions, it is thus achieved that activated spawn;
(2) primary cultivation: the activated spawn obtained in step (1) is inoculated in MRS fluid medium, at 150r/min, under 37 DEG C of conditions, shaking table is cultivated 12��16 hours, obtains seed liquor;
(3) secondary cultivation: being inoculated in MRS fluid medium by the seed liquor that step (2) obtains, the volume of seed liquor is the 4��6% of MRS fluid medium volume, at 150r/min, under 37 DEG C of conditions, fermentation liquid cultivated 48��72 hours to obtain by shaking table;
(4) prepared by crude extract: fermentation liquid concentrated by rotary evaporation step (3) prepared is centrifugal to the 1/4 of original volume, take supernatant ethanol to precipitate, filter and continue to concentrate the filtrate to the 1/4 of original volume, then it is extracted with ethyl acetate, aqueous phase n-butyl alcohol is extracted again, butanol extraction liquid concentrating under reduced pressure is obtained crude extract;
(5) silica gel column chromatography rough segmentation: crude extract methanol prepared by step (4) is dissolved then dress post after silica gel mixed sample, fixing is the silica gel of 80-100 order mutually, with dichloromethane: methanol volume ratio=50:1��1:1 gradient elution, silica gel thin-layer chromatography detects, and collects stream part that volume ratio is 10:1 of methylene chloride-methanol;
(6) by stream part of obtaining in above-mentioned steps (5) through SephadexLH-20 gel filtration chromatography eluting, using dichloromethane: methanol=1:1 is as mobile phase, and through silica gel thin-layer chromatography combining data detection same stream part, it is thus achieved that 3 stream parts;
(7) the 3rd stream part step (5) obtained adopts reversed-phase high-performance liquid chromatography purification, concentrating under reduced pressure, dries, obtains ring (sweet-cheese) dipeptides.
2. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans as claimed in claim 1, it is characterized in that, the formula of described plating medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, agar 15.0g/L, tween 80 1.0mL/L, pH6.0.
3. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans as claimed in claim 1, it is characterized in that, the formula of described MRS fluid medium is: peptone 10.0g/L, Carnis Bovis seu Bubali cream 10.0g/L, yeast extract 5.0g/L, glucose 20.0g/L, sodium acetate 5.0g/L, citric acid diamidogen 2.0g/L, dipotassium hydrogen phosphate 0.4g/L, magnesium sulfate 0.58g/L, manganese sulfate 0.25g/L, tween 80 1.0mL/L, pH6.0.
4. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans as claimed in claim 1, it is characterized in that, in described step (4), after fermentation liquid concentrated by rotary evaporation, the process conditions of centrifugation are: centrifugal condition is temperature 4 DEG C, and rotating speed is 5000rpm, centrifugation time 20min.
5. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans as claimed in claim 1, it is characterised in that the concrete operations of described step (4) supernatant ethanol precipitation are: add the ethanol of isopyknic 95% in supernatant.
6. the method extracting ring (sweet-cheese) dipeptides from Bacillus coagulans as claimed in claim 1, it is characterized in that, the concrete operations that after concentration, filtrate is extracted with ethyl acetate in described step (4) are: filtrate and ethyl acetate 11 will mix by volume after concentration, pour in separatory funnel, shaking flask extracts 2 ~ 3 times, stand 20��30min every time, obtain aqueous phase; Extraction into ethyl acetate obtains the concrete operations of aqueous phase n-butanol extraction: aqueous phase and n-butyl alcohol 11 mix by volume, pour in separatory funnel, and shaking flask extracts 2 ~ 3 times, stands 20��30min every time, obtains butanol extraction liquid.
7. the method extracting ring (sweet-cheese) dipeptides from spore lactobacillus as claimed in claim 1, it is characterised in that the reversed-phase high-performance liquid chromatography condition in described step (7) is:
Chromatographic column: Agilent pursuitC18,10 ��m, 150 �� 21.2mm;
Mobile phase consists of acetonitrile: water=5: 95-50: 50;
Flow velocity: 15ml/min;
Column temperature: 25 DEG C;
Detection wavelength: 230,254nm;
Sample size: 300-500 �� l.
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| CN201610113919.0A CN105648002B (en) | 2016-03-01 | 2016-03-01 | A method of extracting ring (sweet-junket) dipeptides from bacillus coagulans |
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| CN201610113919.0A CN105648002B (en) | 2016-03-01 | 2016-03-01 | A method of extracting ring (sweet-junket) dipeptides from bacillus coagulans |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102061325A (en) * | 2010-11-29 | 2011-05-18 | 大连民族学院 | Method for preparing cyclodipeptide from Bacillus amyloliquefaciens |
| CN103725738A (en) * | 2013-12-17 | 2014-04-16 | 浙江工商大学 | Method for preparing collagen polypeptides by using larimichthys crocea leftovers |
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2016
- 2016-03-01 CN CN201610113919.0A patent/CN105648002B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102061325A (en) * | 2010-11-29 | 2011-05-18 | 大连民族学院 | Method for preparing cyclodipeptide from Bacillus amyloliquefaciens |
| CN103725738A (en) * | 2013-12-17 | 2014-04-16 | 浙江工商大学 | Method for preparing collagen polypeptides by using larimichthys crocea leftovers |
Non-Patent Citations (2)
| Title |
|---|
| 朱洪平: "中国东海海洋微生物环肽类活性物质研究", 《中国博士学位论文全文数据库 基础科学辑》 * |
| 艾峰: "中国东海微生物F8712的分离鉴定及次生代谢产物研究", 《万方数据》 * |
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