CN103408550A - 2,5-diketopiperazine dipeptide derived from lysobacter enzymogenes as well as preparation method and application thereof - Google Patents
2,5-diketopiperazine dipeptide derived from lysobacter enzymogenes as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention provides 2,5-diketopiperazine dipeptide (I) derived from lysobacter enzymogenes as well as a preparation method and an application thereof and an endophytic bacterium producing 2,5-diketopiperazine dipeptide, namely lysobacter enzymogenes R-2-1. 2,5-diketopiperazine dipeptide (I) has the main beneficial effects that (1) lysobacter enzymogenes R-2-1 producing 2,5-diketopiperazine dipeptide (I) is provided and is the first lysobacter enzymogenes produced in the strain; (2) 2,5-diketopiperazine dipeptide (I) has strong inhabiting effects on aspergillus flavus and candida albicans, can serve as a novel bactericide and can be further used for preparing medicament for treating relevant diseases caused by aspergillus flavus or candida albicans; (3) 2,5-diketopiperazine dipeptide (I) is produced by liquid fermentation of lysobacter enzymogenes R-2-1 and has the advantages of simple and convenient operation process, short period, low cost and ensured origin; (4) 2,5-diketopiperazine dipeptide (I) is synthesized by a biological method and does not pollute the environment.
Description
(1) technical field
The present invention relates to a kind of deriving from and produce 2 of the molten bacillus of enzyme (Lysobacter enzymogenes), 5-diketopiperazines dipeptides, and preparation and application, and produce described 2, the endogenetic bacteria of 5-diketopiperazines dipeptides---produce the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1.
(2) background technology
Pathogenic bacterium not only serious harm the health of human body, and are threatening agriculture production, bring very large loss for people of other countries' economy and life.Although the existing sterilant kind of China is numerous, novel pathogenic bacterium and strong resistance pathogenic bacterium can not have effectively been suppressed.Therefore, sterilant must be constantly brought forth new ideas.Bio-pharmaceutical has efficiently, low toxicity, safety, advantages of environment protection, the demand of having catered to China's drug development, and following microbial medicine industry has very large development potentiality.
Enlarging Microbial resources is one of important channels of development of new sterilant.Endophyte of plant is the special microorganism of a class, and it is lived between the health plant histocyte or, in tissue, does not cause any obvious disease symptom of host plant, is endophytic normal microflora.Quantity research shows greatly, and endophyte of plant distributes wide, and kind is many, has important physiology and Ecology Action, and endophyte of plant has abundant Chemical Diversity, can unique, the active material significantly of metabolic chemistry structure.Up to the present, there is not yet from Herba Artemisiae annuae and be separated to the endophyte product molten bacillus of enzyme (Lysobacter enzymogenes) and metabolism 2 thereof, the report of 5-diketopiperazines dipeptides.
(3) summary of the invention
It is a kind of 2 that the object of the invention is to provide, 5-diketopiperazines dipeptides and preparation and application thereof, and produce described 2, the endogenetic bacteria of 5-diketopiperazines dipeptides---produce the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1.
The technical solution used in the present invention is:
A kind of deriving from produced 2 of the molten bacillus of enzyme (Lysobacter enzymogenes), 5-diketopiperazines dipeptides, its structure as shown in the formula (I):
Described endogenetic bacteria produces the molten bacillus R-2-1 of enzyme separation method: fetch fresh and healthy Herba Artemisiae annuae stem (the Artemisia annua Linn. that comes from Tianmu Mountains of Zhejiang Province, composite family, artemisia, Herba Artemisiae annuae kind), pack in freshness protection package and seal mark, in 24h, carry out the endophyte separation.The Herba Artemisiae annuae root is cleaned with clear water, is cut into after the segment of 1cm left and right and is soaked in successively volumetric concentration 75% aqueous ethanolic solution 1min, mass concentration 1% aqueous sodium hypochlorite solution 10min, volumetric concentration 75% aqueous ethanolic solution 1min carries out pre-treatment.Getting pretreated Herba Artemisiae annuae root is cultured to bacterium colony with two anti-WA culture medium flat plates and grows from incision, picking colony is forwarded to the separation that the LB substratum carries out endogenetic fungus, through colonial morphology observation and 16S rRNA Molecular Identification, be the product molten bacillus of enzyme (Lysobacter enzymogenes), the called after endogenetic bacteria produces the molten bacillus R-2-1(Lysobacter of enzyme enzymogenes).Two anti-WA substratum final concentrations form: 200IU/mL amphotericin B, 150IU/mL Streptomycin sulphate, 20g agar, 1L distilled water, natural pH value.LB substratum final concentration forms: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, agar 20g/L, solvent are water, pH7.4.
Endogenetic bacteria produces enzyme molten bacillus R-2-1 morphological specificity and cultural characteristic is: bacterium colony is light yellow, G
-, cell is shaft-like, and spore staining is purple, the methyl red test positive, NaCl content range 0～3%, have oxidase activity and hydrolyzed casein, carboxymethyl cellulose activity, (G+C) content 66.9% in DNA, nitrate-free reducing power.
This bacterium 16S rRNA sequence is:
1tgcagtcgaa?cggcagcaca?gaggagcttg?ctccttgggt?ggcgagtggc?ggacgggtga
61ggaatacgtc?ggaatctgcc?tatttgtggg?ggataacgta?gggaaactta?cgctaatacc
121gcatacgacc?tacgggtgaa?agtgggggac?cgcaaggcct?cacgcagata?gatgagccga
181cgtcggatta?gctagttggc?ggggtaaagg?cccaccaagg?cgacgatccg?tagctggtct
241gagaggatga?tcagccacac?tggaactgag?acacggtcca?gactcctacg?ggaggcagca
301gtggggaata?ttggacaatg?ggcgcaagcc?tgatccagcc?atgccgcgtg?tgtgaagaag
361gccttcgggt?tgtaaagcac?ttttgtccgg?aaagaaaagc?ttagggttaa?taaccttgag
421tcatgacggt?accggaagaa?taagcaccgg?ctaacttcgt?gccagcagcc?gcggtaatac
481gaagggtgca?agcgttactc?ggaattactg?ggcgtaaagc?gtgcgtaggt?ggtttgttaa
541gtctgatgtg?aaagccctgg?gctcaacctg?ggaatggcat?tggaaactgg?cttactagag
601tgcggtagag?ggtagcggaa?ttcccggtgt?agcagtgaaa?tgcgtagata?tcgggaggaa
661catctgtggc?gaaggcggct?acctggacca?gcactgacac?tgaggcacga?aagcgtgggg
721agcaaacagg?attagatacc?ctggtagtcc?acgccctaaa?cgatgcgaac?tggatgttgg
781gggcaacttg?gccctcagta?tcgaagctaa?cgcgttaagt?tcgccgcctg?ggaagtacgg
841tcgcaagact?gaaactcaaa?ggaattgacg?ggggcccgca?caagcggtgg?agtatgtggt
901ttaattcgat?gcaacgcgaa?gaaccttacc?tggccttgac?atgtcgagaa?ctttccagag
961atggattggt?gccttcggga?actcgaacac?aggtgctgca?tggctgtcgt?cagctcgtgt
1021cgtgagatgt?tgggttaagt?cccgcaacga?gcgcaaccct?tgtccttagt?tgccagcacg
1081taatggtggg?aactctaagg?agaccgccgg?tgacaaaccg?gaggaaggtg?gggatgacgt
1141caagtcatca?tggcccttac?ggccagggct?acacacgtac?tacaatggta?gggacagagg
1201gctgcaaacc?cgcgagggca?agccaatccc?agaaacccta?tctcagtccg?gattggagtc
1261tgcaactcga?ctccatgaag?tcggaatcgc?tagtaatcgc?agatcagcat?tgctgcggtg
1321aatacgttcc?cgggccttgt?acacaccgcc?cgtcacacca?tgggagtttg?ttgcaccaga
1381agcaggtagc?ttaaccttcg?ggagggcgct?gc。
The invention still further relates to described 2, the preparation method of 5-diketopiperazines dipeptides, described method comprises: will produce filtering fermentation liquor that the molten bacillus of enzyme (Lysobacter enzymogenes) CCTCC NO:M2013203 obtains through fermentation or centrifugal, get filtrate or supernatant liquor ethyl acetate extraction, get organic layer concentrated, gained medicinal extract is through separation and purification, obtain described 2,5-diketopiperazines dipeptides.
Preferably, described separation purification method is as follows: (1) carries out silica gel column chromatography by gained medicinal extract, take chloroform: the solvent of methyl alcohol volume ratio=100:4 carries out wash-out as eluent, collects elutriant, concentrated, obtains medicinal extract 1; (2) medicinal extract 1 is carried out to silica gel column chromatography, take chloroform: the solvent of methyl alcohol volume ratio=100:2 carries out wash-out as eluent, collects elutriant, concentrated, obtains medicinal extract 2; (3) utilize dextrane gel Sephadex LH-20 to carry out column chromatography to medicinal extract 2, take chloroform: the solvent of methyl alcohol volume ratio=1:1 carries out wash-out as eluent, TLC follows the tracks of and detects the part that contains blue-fluorescence point, collect this part elutriant, after merging elutriant, cryogenic vacuum is removed eluent, obtain 2 shown in formula (I), 5-diketopiperazines dipeptides.
The fermented liquid of the molten bacillus of described product enzyme is obtained through conventional fermentation culture in the fermention medium that routine is applicable to produce the molten bacillus of enzyme by the molten bacillus CCTCC of described product enzyme NO:M2013203, usually before fermentation culture, also needs to cultivate and the seed enlarged culturing through slant activation.
Concrete, described fermented liquid preparation method is as follows:
(1) slant culture: will produce the molten bacillus CCTCC of enzyme NO:M2013203 and be seeded to slant medium, and cultivate 1～3 day for 37 ℃, and obtain the thalline inclined-plane; Described slant medium final concentration consists of: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, agar 20g/L, solvent are water, pH7.4;
(2) seed culture: from thalline inclined-plane picking one transfering loop thalline, be seeded to the LB seed culture medium, shaking table was cultivated 1～3 day under 100～200rpm, 37 ℃ of conditions, obtained seed liquor; Described LB seed culture medium final concentration consists of: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, solvent are water, pH7.4;
(3) fermentation culture: the seed liquor that step (2) is obtained is seeded to fermention medium with the inoculum size of volume ratio 1:20, shaking table was cultivated 3～6 days under 100～200rpm, 30～37 ℃ of conditions, obtain fermentation culture, the fermention medium final concentration forms with the LB seed culture medium.
The present invention obtain 2,5-diketopiperazines dipeptides (I) has very strong restraining effect to flavus (Aspergillus flavus) and Candida albicans (Candida albicans), so this dipeptides can be used as the compound with bacteriostatic action, be expected to be applied in preparing sterilant.
The invention still further relates to described 2, the application of 5-diketopiperazines dipeptides in preparing sterilant.
Preferably, described sterilant is for suppressing the sterilant of flavus (Aspergillus flavus) or Candida albicans (Candida albicans).Further, in described sterilant 2,5-diketopiperazines dipeptides effective concentration is 30ug/mL.
Because flavus or Candida albicans are pathogenic bacterium, so the compounds of this invention further can be used for preparing the medicine of the relative disease that treatment flavus or Candida albicans cause.
Concrete, the invention still further relates to described 2, the application of 5-diketopiperazines dipeptides in the medicine of dermatocandidiasis, candidiasis of the mucous membranes (as white mouth, bridou, vaginitis etc.) or internal organ that preparation treatment Candida albicans causes and nervus centralis moniliosis (as pneumonia, gastroenteritis, endocarditis, meningitis, encephalitis etc.).
The invention still further relates to described 2, the application of 5-diketopiperazines dipeptides in the medicine of food poisoning that preparation treatment flavus causes (especially food poisoning cause hepar damnification).
The invention still further relates to and produce described 2, the endogenetic bacteria of 5-diketopiperazines dipeptides---produce the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1, be preserved in Chinese Typical Representative culture collection center, address: China, Wuhan, Wuhan University, postcode 430072, preservation date is on May 14th, 2013, and deposit number is CCTCC NO:M2013203.
Beneficial effect of the present invention is mainly reflected in:
(1) the invention provides a kind of product 2, the molten bacillus R-2-1 of the product enzyme of 5-diketopiperazines dipeptides (I), this bacterium is in the first strain, to produce the molten bacillus of enzyme;
(2) of the present invention 2,5-diketopiperazines dipeptides (I) has very strong restraining effect to flavus (Aspergillus flavus) and Candida albicans (Candida albicans), can be used as new type bactericide, further can be used for preparing the medicine of the relative disease that treatment flavus or Candida albicans cause;
(3) of the present invention 2,5-diketopiperazines dipeptides (I) derives from and produces the production of the molten bacillus R-2-1 of enzyme liquid fermenting, and operating procedure is easy, and the cycle is short, and cost is low, originates guaranteed;
(4) the present invention utilizes biological process synthetic, environmentally safe.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1: endophyte produces the isolation and purification of the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1
Two anti-WA substratum final concentrations form: 200IU/mL amphotericin B, 150IU/mL Streptomycin sulphate, 20g agar, 1L distilled water, natural pH value.
LB substratum final concentration forms: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, agar 20g/L, solvent are water, pH7.4.
Get the Herba Artemisiae annuae root (Artemisia annua Linn., composite family, artemisia, Herba Artemisiae annuae kind) of fresh and healthy, seal mark in the freshness protection package of packing into, in 24h, carry out the endophyte separation.The Herba Artemisiae annuae root is cleaned with clear water, is cut into after the segment of 1cm left and right and is soaked in successively volumetric concentration 75% aqueous ethanolic solution 1min, mass concentration 1% aqueous sodium hypochlorite solution 10min, volumetric concentration 75% aqueous ethanolic solution 1min carries out pre-treatment.Get pretreated Herba Artemisiae annuae root with two anti-WA culture medium flat plates after under 28～37 ℃, cultivating 2～4 days, bacterium colony grows from incision, picking colony is forwarded to the LB substratum to be separated, through colonial morphology observation and 16S rRNA Molecular Identification, be the product molten bacillus of enzyme (Lysobacter enzymogenes), the called after endogenetic bacteria produces the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1, this bacterial strain is preserved in Chinese Typical Representative culture collection center, preservation date on May 14th, 2013, deposit number is CCTCC NO:M2013203.
Endogenetic bacteria produces the molten bacillus R-2-1 of enzyme bacterium colony and is light yellow, G-, and cell is shaft-like, spore staining is purple, the methyl red test positive, NaCl content range 0～3%, have oxidase activity and hydrolyzed casein, carboxymethyl cellulose activity, (G+C) content 66.9% in DNA, nitrate-free reducing power.
This bacterium 16S rRNA sequence is referring to SEQ ID No.1.
Embodiment 2: endophyte produces the preparation of the molten bacillus R-2-1 of enzyme fermentation culture
(1) slant culture: endogenetic fungus is produced to the molten bacillus R-2-1 of enzyme and be seeded to slant medium, cultivated 2 days for 37 ℃, obtain the thalline inclined-plane; Described slant medium final concentration consists of: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, agar 20g/L, solvent are water, pH7.4;
(2) seed culture: from thalline inclined-plane picking one transfering loop thalline, be seeded to the LB seed culture medium, shaking table was cultivated 2 days under 100～200rpm, 37 ℃ of conditions, obtained seed liquor; Described LB seed culture medium final concentration consists of: yeast extract 5g/L, and Tryptones 10g/L, NaCl10g/L, solvent are water, pH7.4;
(3) fermentation culture: the seed liquor that step (2) is obtained is seeded to fermention medium with the inoculum size of volume ratio 1:20, shaking table was cultivated 3～6 days under 100～200rpm, 30～37 ℃ of conditions, obtain fermentation culture, the fermention medium final concentration forms with the LB seed culture medium.
Embodiment 3: alkaloidal extraction with separate, identify
1, alkaloidal extraction with separate
(1) by gained fermentation culture filtered through gauze in embodiment 2, filtrate, with ethyl acetate (volume ratio 1:1) extraction 3 times, merges organic layer, and the cryogenic vacuum concentrate drying obtains brown crude extract F25g;
(2) medicinal extract F is carried out to silica gel column chromatography, with the mixed organic solvents of 10 times of chromatographic column retention volume (chloroform: methyl alcohol, the wash-out of volume ratio=100:4), merge elutriant, cryogenic vacuum is concentrated, obtains medicinal extract F1;
(3) medicinal extract F1 is carried out to silica gel column chromatography, with mixed organic solvents (chloroform: methyl alcohol, 5 retention volume of wash-out of volume ratio=100:2), merge elutriant, cryogenic vacuum is concentrated, obtains medicinal extract F2;
(4) utilize dextrane gel Sephadex LH-20 to carry out column chromatography to medicinal extract F2, eluent is chloroform and the methyl alcohol mixed liquor of volume ratio 1:1, TLC follows the tracks of and detects the part that contains blue-fluorescence point, collect this part elutriant, after the merging elutriant, cryogenic vacuum is removed eluent and is obtained 2 shown in formula (I), 5-diketopiperazines dipeptides (55mg).
2, alkaloidal Structural Identification
The target product that step 1 is obtained carries out mass spectrum and nuclear magnetic resonance spectroscopy.
Mass-spectrometric data is: ESI-MS m/z259[M-H]
+, 518.8[2M-H]; Determine molecular formula C
14N
16N
2O
3 1H and
13C NMR data are in Table 1.
Table 1:2,5-diketopiperazines dipeptides (I)
1H spectrum and
13C spectrum data (500MHz, CDCl
3)
S-is unimodal, d-doublet, m-multiplet
To sum up, the structural formula of described target product is shown in formula (I):
Isosorbide-5-Nitrae in formula I, 7,9,10,11,12,14 is the carbon atom sequence number, this system of compounds called after (3S, 8aS)-3-(4-hydroxybenzyl) hexahydropyrrolo[1,2-a] pyrazine-1,4-dione.
Embodiment 4: the dipeptides anti-microbial activity is estimated
Agar dilution (Letters in Applied Microbiology is adopted in the evaluation of dipeptides anti-microbial activity, 2011,53:546-551), each triplicate of measuring, the test pathogenic bacterium are flavus (Aspergillus flavus) and Candida albicans (Candida albicans), purchased from Beijing North, receive and create connection Bioteknologisk Institut, strain number is respectively ACCC30321, CAU0037.
Concrete grammar is as follows:
1. test the bacterium preparation: pathogenic bacterium, after dull and stereotyped activation culture, are forwarded in the triangular flask that contains the Cha Shi nutrient solution, shake cultivation 48～72h under 100～200rpm, 28 ± 1 ℃ of conditions, and the Cha Shi nutrient solution consists of: sucrose 30g/L, NaNO
32.0g/L, K
2HPO
41.0g/L, KCl0.5g/L, MgSO
47H
2O0.5g/L, FeSO
47H
2O(100g/L) 2,1L distilled water, natural pH value.2. specimen preparation: by the dipeptides powder dissolution in dimethyl sulfoxide (DMSO) (DMSO), adopt the solution of eight concentration of doubling dilution preparation, be respectively 7.5,15,30,60,120,240,480,960 μ g/mL, positive control is amphotericin B, adopt DMSO to dissolve, prepare the solution of the same eight concentration.3. drug sensitive test: each flat board adds 15mL PDA substratum, gets 100 μ L Cha Shi nutrient solutions and evenly coats in the culture dish that contains the PDA substratum, and the PDA substratum consists of: 20g potato, glucose 20g/L, 20g agar, 1L distilled water, natural pH value.Get again 20 μ L specimen and join in culture dish, evenly coating, standing dull and stereotyped 30min, be inverted into flat board in constant incubator (28 ± 1 ℃) and cultivate 72h.Take out culture dish, observe and whether have the pathogenic bacterium bacterium colony to produce, if do not show pathogenic bacterium suppressed growth under this sample concentration, determine that the antibiotic minimum inhibitory concentration of this sample is the MIC value.
Table 2:2, the antibiotic MIC value of 5-diketopiperazines dipeptides (I) and amphotericin B (μ g/mL)
Claims (9)
1. one kind derives from and produces 2 of the molten bacillus of enzyme (Lysobacter enzymogenes), 5-diketopiperazines dipeptides, its structure as shown in the formula (I):
2. prepare claim 1 described 2, the method of 5-diketopiperazines dipeptides, described method comprises: will produce filtering fermentation liquor that the molten bacillus of enzyme (Lysobacter enzymogenes) CCTCC NO:M2013203 obtains through fermentation or centrifugal, get filtrate or supernatant liquor ethyl acetate extraction, get organic layer concentrated, gained medicinal extract is through separation and purification, obtain described 2,5-diketopiperazines dipeptides.
3. method as claimed in claim 2, it is characterized in that described separation purification method is as follows: (1) carries out silica gel column chromatography by gained medicinal extract, take chloroform: the solvent of methyl alcohol volume ratio=100:4 carries out wash-out as eluent, collects elutriant, concentrated, obtains medicinal extract 1; (2) medicinal extract 1 is carried out to silica gel column chromatography, take chloroform: the solvent of methyl alcohol volume ratio=100:2 carries out wash-out as eluent, collects elutriant, concentrated, obtains medicinal extract 2; (3) utilize dextrane gel Sephadex LH-20 to carry out column chromatography to medicinal extract 2, take chloroform: the solvent of methyl alcohol volume ratio=1:1 carries out wash-out as eluent, TLC follows the tracks of and detects the part that contains blue-fluorescence point, collect this part elutriant, after merging elutriant, cryogenic vacuum is removed eluent, obtain 2 shown in formula (I), 5-diketopiperazines dipeptides.
4. claim 1 is described 2, the application of 5-diketopiperazines dipeptides in preparing sterilant.
5. application as claimed in claim 4, is characterized in that described sterilant is for suppressing the sterilant of flavus (Aspergillus flavus) or Candida albicans (Candida albicans).
6. application as claimed in claim 5, is characterized in that in described sterilant 2, and 5-diketopiperazines dipeptides effective concentration is 30ug/mL.
7. claim 1 is described 2, dermatocandidiasis, candidiasis of the mucous membranes or the internal organ that 5-diketopiperazines dipeptides causes at preparation treatment Candida albicans and the application in the oidiomycotic medicine of nervus centralis.
8. claim 1 is described 2, the application of 5-diketopiperazines dipeptides in the medicine of the food poisoning that preparation treatment flavus causes.
9. produce the molten bacillus of enzyme (Lysobacter enzymogenes) R-2-1, be preserved in Chinese Typical Representative culture collection center, address: China, Wuhan, Wuhan University, postcode 430072, preservation date is on May 14th, 2013, and deposit number is CCTCC NO:M2013203.
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| CN109504610A (en) * | 2018-12-12 | 2019-03-22 | 安徽中医药大学 | A kind of plant endogenesis epiphyte Aspergillus sp.MBL1612 extract and application thereof |
| CN113846034A (en) * | 2021-10-27 | 2021-12-28 | 河北科技大学 | Lysobacter enzymogenes L-43 and application thereof |
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Cited By (6)
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| CN109504610A (en) * | 2018-12-12 | 2019-03-22 | 安徽中医药大学 | A kind of plant endogenesis epiphyte Aspergillus sp.MBL1612 extract and application thereof |
| CN109504610B (en) * | 2018-12-12 | 2021-11-19 | 安徽中医药大学 | Endophytic fungus Aspergillus sp.MBL1612 extract and application thereof |
| CN113846034A (en) * | 2021-10-27 | 2021-12-28 | 河北科技大学 | Lysobacter enzymogenes L-43 and application thereof |
| CN113846034B (en) * | 2021-10-27 | 2024-01-16 | 河北科技大学 | Lysobacter enzymogenes L-43 and application thereof |
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