CN108558727A - The extracting method of pyrroles's -2- carboxylic acids - Google Patents
The extracting method of pyrroles's -2- carboxylic acids Download PDFInfo
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- CN108558727A CN108558727A CN201810454302.4A CN201810454302A CN108558727A CN 108558727 A CN108558727 A CN 108558727A CN 201810454302 A CN201810454302 A CN 201810454302A CN 108558727 A CN108558727 A CN 108558727A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
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Abstract
The invention belongs to microorganisms technical fields, and in particular to a kind of extracting method of 2 carboxylic acid of pyrroles.Include the following steps：Marine bacteria Arenibactersp.6A1 is inoculated into fermentation medium and carries out fermented and cultured, obtains zymotic fluid；The zymotic fluid is adjusted to pH=3~4, extraction processing is then carried out and obtains extract；The extract is dissolved, gel filtration chromatography and HPLC separation is carried out successively, obtains 2 carboxylic acid of pyrroles；Wherein, the condition of the HPLC separation includes：Gradient elution, Detection wavelength 254nm are carried out with methanol/water mixed solvent, the time for collecting liquid phase peak is 23.05min.This method has finally obtained high-purity, 2 carboxylic acid of pyrroles with bacteriostatic activity, and the industrialized production for 2 carboxylic acid of pyrroles provides excellent basis.
Description
Technical field
The invention belongs to microorganisms technical fields, and in particular to a kind of extracting method of pyrroles -2- carboxylic acids.
Background technology
It is more aobvious to the exploitation of novel effective anti-microbial type active material as harmful levels of pathogens drug resistance problems are increasingly severe
It is important.The difficulty that novel active is explored from terrestrial microorganism is increasing, and in contrast, ocean is because of its environmental diversity
And particularity, become the goal seeking of more with prospects.
The bacterium of marine source can generate the various substances with antibacterial activity.Studying more strain has bacillus
Bacillus sp., Vibrio sp., pseudomonas Pseudomonassp., Flavobacterium Flavobacterium
Sp. etc..Li Houjin etc. is detached from the pseudomonas bacterium in Daya Gulf source and is obtained prodigiosin, can effectively be pressed down in vitro
Gram-positive bacteria (staphylococcus aureus and bacillus cereus) processed and disease fungus (Candida albicans, nearly smooth beads
Bacterium and Cryptococcus bacterium) growth；Tareq etc. is reported from bacillus marinus category (Bacillus sp.109GGC020)
4 kinds of isolated novel lipopeptid compound gageopeptides A~D, 1 pair of staphylococcus aureus of such compound pair,
The bacteriums such as Salmonella typhi and pseudomonas aeruginosa show medium antibacterial activity (μ of MIC=8~64 g/ml).
Arenibacter belongs to the leather of Bacteroidetes (Bacteroidetes) Flavobacterium section (Flavobacteriaceae)
Lan Shi negative bacteriums, all from marine environment, source includes ocean bed mud, brown alga to the current reported in literature of the category bacterium for acquisition
(Chorda filum), green alga (Ulvafenestrata) and edible sea cucumber (Apostichopusjaponicus).Document
Report Arenibacter can synthesize beta-N- acetyl-Glucosamine of a variety of special glycosidases, especially high activity
Glycosides enzyme and alpha-N- acetylglactoside enzymes.The diatom from laboratory cultures such as Tony Gutierrez
(Skeletonemacostatum) isolated 7 plants of Arenibacter belong to bacterium in culture solution, find the phenanthrene that can all degrade
(phenanthrene), one plant of Arenibacterlatericius KCTC 12957 is removedTOutside, can all degrade naphthalene
(naphthalene), therefore, it is considered that degrading polycyclic aromatic hydrocarbons can be as the category bacterial strain one of diagnostic characteristics.Height sky is equal from China
One plant of Arenibacter in South Sea bed mud source belongs to separation in bacterium (Arenibacternanhaiticus sp.nov.NH36AT)
A series of phenyl ethylamine class compounds are obtained, such compound has faint anti-Staphylococcus aureus and bacillus subtilis
Activity (0.50 and 0.25mg/ml of MIC).
Pyrroles -2- carboxylic acids (pyrrole-2-carboxylic acid, PCA) have certain bacteriostatic activity, such as to green pus
The inhibiting effect of bacillus and the growth of Activities of Some Plants pathogenic bacteria, therefore its application prospect is boundless.But in the prior art, from micro-
The technology that pyrroles's -2- carboxylic acids are extracted in bio-fermented liquid is very limited.
Invention content
It is an object of the invention to overcome the above-mentioned deficiency of the prior art, a kind of extracting method of pyrroles -2- carboxylic acids is provided,
Aim to solve the problem that the very limited technical problem of the extractive technique of existing pyrroles -2- carboxylic acids.
For achieving the above object, the technical solution adopted by the present invention is as follows：
A kind of extracting method of pyrroles -2- carboxylic acids, includes the following steps：
Marine bacteria Arenibactersp.6A1 is inoculated into fermentation medium and carries out fermented and cultured, obtains zymotic fluid；
The zymotic fluid is adjusted to pH=3~4, extraction processing is then carried out and obtains extract；
The extract is dissolved, gel filtration chromatography and HPLC separation is carried out successively, obtains pyrroles's -2- carboxylic acids；
Wherein, the condition of the HPLC separation includes：Gradient elution is carried out with methanol/water mixed solvent, Detection wavelength is
254nm, the time for collecting liquid phase peak are 23.05min.
Separation obtains pyrroles's -2- carboxylic acids, the extracting method to the present invention from marine bacteria Arenibactersp.6A1 for the first time
The bacterium is first subjected to bulk fermentation with fermentation medium, is then extracted, it is existing using gel filtration chromatography and HPLC separation etc.
The secondary metabolite generated to fermentation for chromatography means isolates and purifies, and the application of the reactive compound to obtaining is modern
Method of spectroscopy and physicochemical property etc. determine its chemical constitution, finally obtain high-purity, pyrroles's -2- carboxylics with bacteriostatic activity
Acid, the industrialized production for pyrroles's -2- carboxylic acids provide excellent basis.
Specific implementation mode
In order to make technical problems, technical solutions and advantageous effects to be solved by the present invention be more clearly understood, below in conjunction with
Embodiment, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only used to explain
The present invention is not intended to limit the present invention.
On the one hand, an embodiment of the present invention provides a kind of extracting method of pyrroles -2- carboxylic acids, include the following steps：
S01：Marine bacteria Arenibactersp.6A1 is inoculated into fermentation medium and carries out fermented and cultured, is sent out
Zymotic fluid；
S02：The zymotic fluid is adjusted to pH=3~4, extraction processing is then carried out and obtains extract；
S03：The extract is dissolved, gel filtration chromatography and HPLC separation is carried out successively, obtains pyrroles's -2- carboxylic acids；Its
In, the condition of the HPLC separation includes：Gradient elution is carried out with methanol/water mixed solvent, Detection wavelength 254nm is collected
The time at liquid phase peak is 23.05min.
Separation obtains pyrroles's -2- carboxylic acids, the extraction side to the present invention from marine bacteria Arenibacter sp.6A1 for the first time
The bacterium is first carried out bulk fermentation by method with fermentation medium, is then extracted in acid condition, using gel filtration chromatography
It the modern chromatographics such as detaches with HPLC and learns to do the secondary metabolite that section generates fermentation and isolate and purify, and the activity to obtaining
Compound application Modern spectroscopy method (MS, NMR, COSY, HSQC, HMBC, NOE etc.) and physicochemical property etc. determine its chemistry knot
Structure, finally obtains high-purity, pyrroles's -2- carboxylic acids with bacteriostatic activity, and the industrialized production for pyrroles's -2- carboxylic acids provides very well
Basis.
Marine bacteria provided in an embodiment of the present invention is red tide water sample bacterium Arenibactersp.6A1, is picked up from Chinese deep
Ditch between fields Nan'ao Dongshan harbour (is preserved in China typical culture collection center, bacterium numbering：CCTCC M 2017262).In order to
Make strains A renibactersp.6A1 that there is preferably activity, improve subsequent fermentation effect, by the marine bacteria
Arenibacter sp.6A1 are inoculated into before fermentation medium, are first handled through recovery on 2216E solid mediums, i.e., will be low
The marine bacteria Arenibactersp.6A1 tablets of warm preservation are recovered.2216E solid mediums：For 2216E fluid nutrient mediums
(formula is：Peptone 5g/L, yeast extract 1g/L, high ferric phosphate 0.01g/L, sea salt 20g/L) plus 1.5% agar, through 121 DEG C of height
Pressure sterilizing obtains for 20 minutes.
Further, the fermentation medium is 2216E fluid nutrient mediums, is formulated and is：Peptone 5g/L, yeast extract 1g/
L, high ferric phosphate 0.01g/L, sea salt 20g/L).
Further, in order to improve the yield of pyrroles's -2- carboxylic acids, ferment effect need to be further increased.The embodiment of the present invention
In the condition of preferred fermented and cultured be：Rotating speed 180rpm, 28 DEG C of temperature, time 96h.I.e. under this condition, high-content can be obtained
The zymotic fluid of the marine bacteria Arenibactersp.6A1 of pyrroles's -2- carboxylic acids.
Further, in above-mentioned steps S02, the step of extraction processing, includes：It is right using ethyl acetate as extractant
The zymotic fluid is extracted, and is then rotated and is evaporated at less than 50 DEG C, and the extract of ethyl acetate layer is obtained.It is preferred that
The step of ground, the extraction processing, extracts entirely as much as possible in triplicate, by the target substance (pyrroles -2- carboxylic acids) in zymotic fluid
It gets.
Further, in above-mentioned steps S03, the gel filtration chromatography is that (hydroxypropyl glucan is solidifying by Sephadex LH20
Glue, one kind of convenience goods gel) column chromatography.The step of Sephadex LH20 column chromatographies includes：By the extract methanol
Dissolving, then with chloroform:Methanol=1:1 carries out Gradient elution for eluting solvent, successively there are 8 isometric fractions：G3-
A, the polarity of G3-B, G3-C, G3-D, G3-E, G3-F, G3-G and G3-H, 8 fractions are sequentially reduced.Then by polarity minimum
Fraction G3-H concentration be evaporated, after being dissolved in methanol, gradient elution is carried out with methanol/water mixed solvent.Wherein, gradient elution when
Between be 30min, flow velocity 1mL/min.In this way, separating effect is best.
On the other hand, the embodiment of the present invention also demonstrates bacteriostatic activity (five plants of Acinetobacter bauamnniis of pyrroles's -2- carboxylic acids
Acinetobacterbaumannii, three plants of Pseudomonas aeruginosa Pseudomonasaeruginosa and two plants of Klebsiella pneumoniaes
Klebsiellapneumonia), illustrate that pyrroles's -2- carboxylic acids prepared by the embodiment of the present invention can be used for preparing Bao Man not levers
Bacteria inhibitor, Pseudomonas aeruginosa inhibitor and Klebsiella pneumoniae inhibitor, and the Arenibacter of the embodiment of the present invention
The zymotic fluid of sp.6A1 can be used for preparing Acinetobacter bauamnnii inhibitor, Pseudomonas aeruginosa inhibitor and Klebsiella pneumoniae suppression
Preparation.I.e. the embodiment of the present invention additionally provides a kind of pyrroles -2- carboxylic acids and is used to prepare Acinetobacter bauamnnii inhibitor, Pseudomonas aeruginosa
The application of inhibitor and Klebsiella pneumoniae inhibitor.
Report embodiment of the present invention is come to produce pyrroles-in derived bacterium Arenibacter sp.6A1 from one plant of Shenzhen waters red tide
2- carboxylic acids, with its antibacterial activity screening results to 47 plants of clinical germs.It was found that the compound in 400 μ g/ml in experiment
It uses five plants of Acinetobacter bauamnniis, three plants of Pseudomonas aeruginosas and two plants of Klebsiella pneumoniaes and shows certain bacteriostatic activity.
The present invention successively carried out test of many times, and it is further detailed to invention progress as reference now to lift A partial experiment result
Thin description, is described in detail with reference to specific embodiment.
Embodiment 1
Arenibactersp.6A1 strain fermentations
The marine bacteria Arenibactersp.6A1 of low-temperature preservation is recovered in plating medium upper flat plate, then will be answered
Soviet Union's strain is inoculated into fermentation medium, 180rpm, and 28 DEG C are cultivated 96 hours；
Wherein, plating medium is that (formula is 2216E fluid nutrient mediums：Peptone 5g/L, yeast extract 1g/L, phosphoric acid are high
Iron 0.01g/L, sea salt 20g/L) plus 1.5% agar, through 121 DEG C of high pressure sterilizations 20 minutes；Fermentation medium is trained for 2216E liquid
Supporting base, (formula is：Peptone 5g/L, yeast extract 1g/L, high ferric phosphate 0.01g/L, sea salt 20g/L).
After fermenting according to the method described above, you can obtain the marine bacteria Arenibacter containing pyrroles's -2- carboxylic acids
The zymotic fluid of sp.6A1.
Embodiment 2
The separation of pyrroles's -2- carboxylic acids
The zymotic fluid that embodiment 1 is obtained carries out following steps：
Ethyl acetate extracts：The pH to 3~4 that zymotic fluid is adjusted with the hydrochloric acid of 1mol/L, is extracted with ethyl acetate, will extract
Obtained extract liquor rotates at less than 50 DEG C to be evaporated, and extraction process, obtains the extract 2g of ethyl acetate layer in triplicate.
Gel filtration chromatography：The extract of ethyl acetate layer is dissolved in 2mL methanol, carrying out Sephadex LH20, (pillar is advised
Lattice：Diameter=3.5cm, column length=100cm) column chromatography is 1 using 400mL volume ratios:1 chloroform and the mixed liquor of methanol are made
Gradient elution is carried out for eluting solvent, a fraction is collected as per 50mL, there are 8 fractions, G3-A, G3-B, G3-C, G3-
D, G3-E, G3-F, G3-G and G3-H.
HPLC is detached：The concentration of G3-H fractions is evaporated, is dissolved in 1mL methanol, carrying out gradient with methanol/water mixed solvent washes
De- (gradient：MeOH:H2O=MeOH:H2O=5:95~80:20, eluent gradient timetable：30min, flow velocity 1mL/min), inspection
Wavelength 254nm is surveyed, liquid phase peak is collected when 23.05min, obtains objective fraction, it is dry, obtain compound：Pyrroles's -2- carboxylic acids
(9mg).(the HPLC models of use：Agilent 1260；Detector models：Agilent 1260DAD；Pillar classification is with specification：
YMC-C18,4.6×250mm,5μm)。
Structural analysis test is carried out to the compound of above-mentioned HPLC resulting separations, obtains following physicochemical property data：
White powder, LC-MS m/z 112.3 [M+H]+, 134.4 [M+Na]+；1H NMR (600MHz, DMSO-d6) and13C
NMR (600MHz, DMSO-d6) data see the table below NMR data (600MHz, the DMSO-d of 1 compound6, J in Hz, δ in ppm).
Table 1
According to the above physicochemical data it is found that the data of this compound and existing pyrroles -2- carboxylic acid data are completely the same.Therefore
Identify that the isolated compounds of the HPLC are pyrroles's -2- carboxylic acids, structure is as follows：
Embodiment 3
The anti-phytopathogenic fungi activity identification of pyrroles's -2- carboxylic acids
The clinical pathogenic bacteria of 47 plants of pyrroles -2- carboxylic acids pair by the way that gradient concentration is arranged carries out antibacterial tests.It will with DMSO
Pyrroles -2- the carboxylic acids that embodiment 2 is extracted are then diluted to 100 μ g/ μ l at 200 μ g/ μ l sample concentrations.By 47 plants of clinics
In LB, (formula is pathogenic bacteria：Tryptone 10g/l, yeast extract 5g/l, NaCl 10g/l, agar 15g/l) tablet training
It supports in base after recovery (37 DEG C, 1d), picking single bacterium drops down onto in the 50ml centrifuge tubes equipped with 20ml LB culture mediums, 180rpm, 37 DEG C
Shaking table culture 1d；LB agar mediums are reconfigured, 1% above-mentioned bacterial solution is accessed after it is cooled to 40 DEG C or so, is shaken up,
A kind of rhyme scheme in Chinese operas serving as the prelude to a complete score for voices places the filter paper after sterilizing on the tablet of solidification, is separately added into the pyrroles's -2- carboxylic acids sample prepared the fronts 2ul extremely
The final concentration of 400 μ g/ml of sample, 200 μ g/ml, control group 2 μ l DMSO of addition, each experimental group and control group are respectively set 3
A repetition；The tablet handled well is put to 37 DEG C and is cultivated, after 1d the case where the generation of observation inhibition zone.Two concentration of display of table 2
The antibacterial Effect of screening of the clinical pathogenic bacteria of 47 plants of sample pair.It wherein finds, pyrroles -2- carboxylic acids are to examination when 400 μ g/ml final concentrations
Five plants of Acinetobacter bauamnniis, three plants of Pseudomonas aeruginosas and two plants of Klebsiella pneumoniaes are used in testing shows certain bacteriostatic activity
(being shown in Table 2).
Table 2
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
All any modification, equivalent and improvement etc., should all be included in the protection scope of the present invention made by within refreshing and principle.
Claims (10)
1. a kind of extracting method of pyrroles -2- carboxylic acids, which is characterized in that include the following steps：
Marine bacteria Arenibactersp.6A1 is inoculated into fermentation medium and carries out fermented and cultured, obtains zymotic fluid；
The zymotic fluid is adjusted to pH=3~4, extraction processing is then carried out and obtains extract；
The extract is dissolved, gel filtration chromatography and HPLC separation is carried out successively, obtains pyrroles's -2- carboxylic acids；
Wherein, the condition of the HPLC separation includes：Gradient elution is carried out with methanol/water mixed solvent, Detection wavelength is
254nm, the time for collecting liquid phase peak are 23.05min.
2. the extracting method of pyrroles -2- carboxylic acids as described in claim 1, which is characterized in that the marine bacteria
Arenibacter sp.6A1 are inoculated into before fermentation medium, are first handled through recovery on 2216E solid mediums.
3. the extracting method of pyrroles -2- carboxylic acids as described in claim 1, which is characterized in that the fermentation medium is 2216E
Fluid nutrient medium.
4. the extracting method of pyrroles -2- carboxylic acids as described in claim 1, which is characterized in that the condition of the fermented and cultured is：
Rotating speed 180rpm, 28 DEG C of temperature, time 96h.
5. the extracting method of pyrroles -2- carboxylic acids as described in claim 1, which is characterized in that the step of extraction processing wraps
It includes：Using ethyl acetate as extractant, the zymotic fluid is extracted, then rotates and is evaporated at less than 50 DEG C, obtain acetic acid
The extract of methacrylate layer.
6. the extracting method of pyrroles -2- carboxylic acids as claimed in claim 5, which is characterized in that the weight the step of extraction processing
Again three times.
7. the extracting method of pyrroles -2- carboxylic acids as described in claim 1, which is characterized in that the gel filtration chromatography is
Sephadex LH20 column chromatographies.
8. the extracting method of pyrroles -2- carboxylic acids as claimed in claim 7, which is characterized in that the Sephadex LH20 column layers
The step of analysis includes：The extract is dissolved with methanol, then with chloroform:Methanol=1:1 carries out constant gradient for eluting solvent
Elution, successively there are 8 isometric fractions：G3-A, G3-B, G3-C, G3-D, G3-E, G3-F, G3-G and G3-H.
9. the extracting method of pyrroles -2- carboxylic acids as claimed in claim 8, which is characterized in that the HPLC, which is detached, includes：By institute
The fraction concentration for stating G3-H is evaporated, and after being dissolved in methanol, gradient elution is carried out with methanol/water mixed solvent.
10. such as the extracting method of claim 1-9 any one of them pyrroles's -2- carboxylic acids, which is characterized in that the HPLC separation
In, the time of gradient elution is 30min, flow velocity 1mL/min.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103667073A (en) * | 2013-09-27 | 2014-03-26 | 浙江工业大学 | Huperzia serrata endophytic fungus and application in preparation of pyrrole type liver-protecting medicines |
| CN108013036A (en) * | 2017-12-12 | 2018-05-11 | 深圳大学 | A kind of application of pyrroles -2- carboxylic acids and preparation method |
| CN108220357A (en) * | 2017-12-12 | 2018-06-29 | 深圳大学 | A kind of application of pyrroles -2- carboxylic acids and preparation method |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103667073A (en) * | 2013-09-27 | 2014-03-26 | 浙江工业大学 | Huperzia serrata endophytic fungus and application in preparation of pyrrole type liver-protecting medicines |
| CN108013036A (en) * | 2017-12-12 | 2018-05-11 | 深圳大学 | A kind of application of pyrroles -2- carboxylic acids and preparation method |
| CN108220357A (en) * | 2017-12-12 | 2018-06-29 | 深圳大学 | A kind of application of pyrroles -2- carboxylic acids and preparation method |
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