CN109251145A - A kind of phthalic acid ester and preparation method thereof, bacterial strain and application - Google Patents
A kind of phthalic acid ester and preparation method thereof, bacterial strain and application Download PDFInfo
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- CN109251145A CN109251145A CN201810994356.XA CN201810994356A CN109251145A CN 109251145 A CN109251145 A CN 109251145A CN 201810994356 A CN201810994356 A CN 201810994356A CN 109251145 A CN109251145 A CN 109251145A
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- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
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Abstract
The invention discloses a kind of phthalic acid ester and preparation method thereof, bacterial strain and applications, the filtering fermentation liquor that the fermented culture of ball anthrax-bacilus ZZP-L1 is obtained or centrifugation, filtrate or supernatant ethyl acetate or methylene chloride is taken to extract, organic layer is taken to be concentrated into no liquid outflow, the inverted high performance liquid chromatography separation purifying of concentrate, the peak for collecting the 6th and 14 minute respectively, removes solvent, respectively obtains phthalic acid ester shown in formula (I) or formula (II).Phthalic acid ester (I) of the invention has inhibiting effect to Candida albicans (Candida albicans), can be used as new antibiotic, is expected to be applied to the drug of the preparation treatment microbial related disease of Candida albicans；Two kinds of phthalic acid esters of the invention are produced from ball anthrax-bacilus ZZP-L1 liquid fermentation, and operating procedure is simple, and the period is short, and at low cost, source is guaranteed；The present invention is synthesized using bioanalysis, no pollution to the environment.
Description
(1) technical field
The present invention relates to two kinds of phthalic acid esters and its biological preparation method and purposes, and produce the phthalic acid
The symbiotic effects of ester-ball anthrax-bacilus (Colletotrichum coccodes ZZP-L1).
(2) background technique
The discovery of novel antibacterial lead compound is always the hot spot of Pharmaceutical Chemist concern.Plant symbiosis bacterium is one
The special microorganism of class lives between health plant histocyte or in tissue, does not cause any obvious disease of host plant
Evil symptom, forms the relationship of mutualistic symbiosis with host.A large amount of chemical research show that plant symbiosis fungi has chemistry abundant more
Sample, being capable of metabolic chemistry unique structure, the significant compound of bioactivity.Strand plant life environment is very special, is total to
Raw fungi has and the different existence of land microorganism and metabolic mechanism.Carry out strand plant symbiosis bacterium chemical research in a deep going way,
It is of great significance to the significant primer of antibacterial is found.Phthalic acid ester is a kind of common plasticiser, has interference people
The effect of internal excretory system, it may have the bioactivity such as certain antibacterial.Currently, production phthalic acid ester is mainly that chemistry closes
At being esterified under the catalysis of acid by phthalic anhydride and alcohol, although yield is high, it is secondary instead that there is dehydration, oxidations etc.
It answers, the problems such as target product is unstable, liquid waste processing is difficult.
(3) summary of the invention
It is an object of the present invention to provide a kind of phthalic acid ester and biological preparation method and applications, and this adjacent benzene of production
The symbiotic effects of dicarboxylic acid esters-ball anthrax-bacilus (Colletotrichum coccodes ZZP-L1).
The technical solution adopted by the present invention:
The present invention provides phthalic acid ester shown in a kind of formula (I) or formula (II),
The present invention also provides a kind of preparation method of phthalic acid ester, the methods are as follows: by ball anthrax-bacilus ZZP-
The filtering fermentation liquor or centrifugation that the fermented culture of L1 obtains, take filtrate or supernatant ethyl acetate or methylene chloride to extract, take
Organic layer is concentrated into no liquid outflow, and the inverted high performance liquid chromatography separation purifying of concentrate is collected the 6th and 14 minute respectively
Peak removes solvent, respectively obtains phthalic acid ester shown in formula (I) or formula (II).
Further, the purification condition are as follows: liquid phase instrument UV-VIS, detector are Shimadzu SPD-10AV, efficient liquid
Phase infusion pump is Shimadzu LC-10AD；Chromatographic condition: C18250 × 9.4mm of chromatographic column, flow velocity 3.0mL/min, 30 DEG C of column temperature, detection
Wavelength 203nm；Flow the distilled water of phase composition volume ratio 10:90: acetonitrile.
Further, the fermentation liquid is prepared as follows:
(1) inclined-plane culture: being seeded to slant medium for ball anthrax bacterial strain ZZP-L1,28 DEG C moisturizing culture 3-4 days, obtain
Thallus inclined-plane；The slant medium final concentration composition are as follows: sucrose 20g/L, potato 200g/L, agar 15-20g/L, solvent
For distilled water, pH nature；
(2) seed culture: being seeded in 100mL seed culture medium from one oese thallus of thallus inclined-plane picking,
200rpm, shaking table culture 3 days under the conditions of 28 DEG C, seed liquor is obtained；The seed culture medium final concentration composition are as follows: potato 100-
200g/L, sucrose 10-20g/L, solvent are distilled water, and pH is natural；It is preferred that the seed culture medium final concentration composition are as follows: potato
200g/L, sucrose 20g/L, solvent are distilled water, and pH is natural；
(3) seed liquor that step (2) obtain fermented and cultured: is seeded to 200mL hair with the inoculum concentration of volumetric concentration 10%
In ferment culture medium, shaking table culture 8-15 days under the conditions of 200rpm, 28 DEG C, fermentation liquid, fermentation medium final concentration composition are obtained
It is formed with seed culture medium.
In addition, the present invention also provides phthalic acid esters shown in a kind of formula (I) to prepare the application in antibacterial agent, it is excellent
Selecting the antibacterial agent is Candida albicans (Candida albicans) antibacterial agent, and more preferable Candida albicans ATCC10231 is anti-
Microbial inoculum.Phthalic acid ester shown in formula (I) is 50 μM to the effective concentration of Candida albicans (Candida albicans).
The invention further relates to a kind of ball anthrax bacterial strain (Colletotrichum for being used to prepare the phthalic acid ester
Coccodes) ZZP-L1 is preserved in China Committee for Culture Collection of Microorganisms's common micro-organisms center, the deposit date is
On June 28th, 2018, deposit number be CGMCC No:16083, address:: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3, in
Institute of microbiology of the academy of sciences of state, postcode 100101.
Compared with prior art, the beneficial effects are mainly reflected as follows:
(1) present invention provides a kind of ball anthrax-bacilus ZZP-L1 for producing the phthalic acid ester；
(2) phthalic acid ester of the invention (I) has inhibiting effect to Candida albicans (Candida albicans), can
As new antibiotic, it is expected to be applied to the drug of the preparation treatment microbial related disease of Candida albicans；
(3) two kinds of phthalic acid esters of the invention are produced from ball anthrax-bacilus ZZP-L1 liquid fermentation, operating procedure
Simply, the period is short, at low cost, and source is guaranteed；
(4) present invention is synthesized using bioanalysis, no pollution to the environment.
(4) specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This:
Embodiment 1: the separation and identification of ball anthrax-bacilus (Colletotrichum coccodes) ZZP-L1
1, bacterial strain ZZP-L1 is separated
Slant medium (i.e. PDA culture medium) final concentration composition are as follows: sucrose 20g/L, potato 200g/L, agar 20g/L,
Solvent is distilled water, natural ph.
Seed culture medium (i.e. PDB culture medium) final concentration composition are as follows: potato 200g/L, sucrose 20g/L, solvent are distillation
Water, pH are natural.
By Zhejiang Polytechnical University teacher Zhang Huawei, using common fungal component isolation technics, (concrete operations refer to bacterial strain ZZP-L1
Bangladesh Journal of Pharmacology, 2012,7:120-123) for the first time from the invaluable (Rumex of strand plant
Obtusifolius Linn.) in it is isolated, and be inoculated in slant medium.
2, bacterial strain ZZP-L1 is identified
(1) morphological feature: bacterial strain ZZP-L1 is inoculated into PDA culture medium, and 28 DEG C activate 3-4 days, with oese picking
Bacterium colony is activated in new PDA culture medium, 28 DEG C of constant temperature incubations.ZZP-L1 strain growth is slow, and bacterium colony is just white, villus
Relatively slightly, black is gradually become from red from centre beginning after.The elongated winding of mycelia, there is a large amount of branches, and branch is short.Conidiophore
Cylindrical shape, it is sometimes slightly curved or have branch.
(2) molecular biology identification
The 18S rDNA that bacterial strain ZZP-L1 is extracted and expanded using molecular biology method, through DNA bis- generations sequencing technologies
(Biomek NX) measures its nucleotides sequence and is classified as shown in SEQ ID NO.1.
Result is analyzed according to bacterial strain ZZP-L1 colony morphology characteristic and 18S rDNA sequence (GenBank number MF376146)
(analysis of Clustal X and MEGA software) identifies that bacterial strain ZZP-L1 is ball anthrax-bacilus (Colletotrichum coccodes),
It is named as ball anthrax-bacilus (Colletotrichum coccodes) ZZP-L1, which is preserved in Chinese microorganism strain preservation
Administration committee's common micro-organisms center (CGMCC), the deposit date is on June 28th, 2018, deposit number CGMCC
No.16083, preservation address Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3 Institute of Microorganism, Academia Sinica, postcode
100101。
Embodiment 2: the preparation of ball anthrax-bacilus ZZP-L1 fermentation culture
(1) inclined-plane culture: being seeded to slant medium for ball anthrax-bacilus ZZP-L1,28 DEG C incubator moisturizing culture 3-4 days,
Obtain thallus inclined-plane；The slant medium final concentration composition is the same as embodiment 1.
(2) seed culture: it is seeded to seed culture medium from one oese thallus of thallus inclined-plane picking, in 200rpm, 28 DEG C
Under the conditions of shaking table culture 3 days, obtain seed liquor；The seed culture medium final concentration composition is the same as embodiment 1.
(3) seed liquor that step (2) obtain fermented and cultured: is seeded to fermented and cultured with the inoculum concentration of volumetric concentration 10%
Base obtains fermentation culture shaking table culture 10 days under the conditions of 200rpm, 28 DEG C, and fermentation medium final concentration forms same seed
Culture medium.
The extraction of 3: two kinds of phthalic acid esters of embodiment with separate, identify
1, the extraction of two kinds of phthalic acid esters with separate
After filtering by 2 gained fermentation liquid of embodiment, filtrate is extracted 2 times with ethyl acetate (volume ratio 1:1) room temperature, is taken
Layer organic phase, cryogenic vacuum are concentrated (35 DEG C, 0.01MPa) to no liquid and flow out, and 40 DEG C of dryings obtain brown coarse extract F；Thick leaching
The the 6th, 14 minute peak, cryogenic vacuum (35 are collected in the inverted high performance liquid chromatography of cream F methanol solution (RP-HPLC) separation respectively
DEG C, 0.01MPa) removal mobile phase obtain compound (I), compound (II).
Liquid phase instrument: UV-VIS, detector: Shimadzu SPD-10AV；Efficient liquid phase infusion pump: Shimadzu LC-10AD；Chromatostrip
Part: C18250 × 9.4mm of chromatographic column, flow velocity 3.0mL/min, 30 DEG C of column temperature, Detection wavelength 203nm；Flow phase composition distilled water
(A): acetonitrile (B)=10:90 (volume ratio).
2, the Structural Identification of compound (I)
The purpose compound (I) of acquisition is subjected to mass spectrum and nuclear magnetic resonance spectroscopy.
(1) mass spectrometric data are as follows: ESI-MS m/z 301 [M+Na]+；Determine molecular formula C16H22O4；Nuclear magnetic data ownership is shown in Table
1。
Table 1: compound (I)1H-NMR nuclear magnetic data and ownership
In conclusion target product (I) structural formula is shown in formula (I):
The Compound nomenclature are as follows: di-isobutyl phthalate (diisobutyl phthalate).
3, the Structural Identification of compound (II)
The purpose compound (II) of acquisition is subjected to mass spectrum and nuclear magnetic resonance spectroscopy.
Mass spectrometric data are as follows: ESI-MS m/z 391 [M+H]+、413[M+Na]+；Determine that molecular formula is C24H38O4；Nuclear-magnetism number
2 are shown in Table according to ownership.
2 compound of table (II)1H-NMR nuclear magnetic data and ownership
In conclusion target product structural formula is shown in formula (II):
The Compound nomenclature are as follows: bis (6-methylheptyl) phthalate (phthalic acid -10,10`- dimethyl -
Two heptyl esters).
4: two kinds of phthalic acid ester bacteriostatic activity evaluations of embodiment
Described two compound activity evaluations use concentration gradient dilution method, and measurement is repeated 6 times every time, tests bacterium bag of causing a disease
Include Escherichia coli (Escherichia coli) ATCC25922, staphylococcus aureus (Staphylococcus aureu)
ATCC 25923 and Candida albicans (Canidia albicans) ATCC10231.
The specific method is as follows:
1, it is transferred in fluid nutrient medium after three plants of indicator bacterias are activated, bacterium (Escherichia coli, staphylococcus aureus)
It is seeded to LB culture medium (distilled water 1000mL, tryptone 10g, yeast extract 5g, sodium chloride 10g, pH value are natural), 37 DEG C
Culture is for 24 hours；(distilled water 1000mL, potato 200g, glucose 20g, pH value is certainly to PD culture medium for fungi (Candida albicans)
So), 28 DEG C of culture 48h, and being diluted to cell density with corresponding fresh culture is 105-106The bacteria suspension of cfu/mL, it is standby
With.
2, precision weighs amikacin sulfate (Kanamycin A Sulfate Sulfate) and is dissolved (100 μM), ammonia benzyl with sterile water
Benzylpenicillin sodium salt (Ampicillin Sodium) and amphotericin B (Amphotericin B) dmso solution (100 μ
M), spare.
3, each sample solution is drawn to be added in 96 orifice plates, so that the sample solution volume in the first hole is 200 μ L, it is initial dense
Degree is 100 μM.After mixing evenly, be added in next hole from drawing 100 μ L in the first hole, and so on (in addition to the first hole its
The bacteria suspension of 100 μ L is added in remaining a few holes in advance) so that the corresponding sample concentration in every hole are as follows: 100,50,25,12.5,6.25,
3.125,1.56,0.78,0.39,0.195μM.Using DMSO as negative control group (not adding test sample), blank cultures
As blank control group (not adding DMSO and test sample), drug is as positive controls (addition amikacin sulfate, ammonia benzyl
Benzylpenicillin sodium salt or amphotericin B).It cultivates for 24 hours, is observed after cultivating 48h at 28 DEG C of fungi, and use microplate reader at 37 DEG C of bacterium
Light absorption value of the detection instruction bacteria culture fluid 600nm at, records data, analyze as a result, every group of experiment do 3 groups it is parallel.Find suppression
Indicator bacteria processed grows minimum concentration, the as minimal inhibitory concentration of the compound, and the results are shown in Table 3.
Inhibiting effect MIC value of 3 compound of table to 3 kinds of cause of disease indicator bacterias
Bacteriostatic activity evaluation result shows that compound (I) has certain growth inhibition effect to C.albican, and changes
Object (II) is closed to three kinds of pathogenic bacteria without growth inhibitory activity, shows that compound (I) has in preparing antibacterial agent and centainly answers
Use prospect.
Sequence table
<110>Zhejiang Polytechnical University
<120>a kind of phthalic acid ester and preparation method thereof, bacterial strain and application
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 1679
<212> DNA
<213>ball anthrax-bacilus (Colletotrichum coccodes)
<400> 1
ataagccatt atacagcgaa actgcgaatg gctcattata taagttatcg tttatttgat 60
agtaccttac tacttggata accgtggtaa ttctagagct aatacatgct aaaaatcccg 120
acttcggaag ggatgtattt attagattaa aaaccaatgc ccttcggggc tcactggtga 180
ttcataataa cttctcgaat cgcatggcct tgcgccggcg atggttcatt caaatttctt 240
ccctatcaac tttcgatgct agagtagtgt tctagcatgg ttacaacggg taacggaggg 300
ttagggctcg accccggaga aggagcctga gaaacggcta ctacatccaa ggaaggcagc 360
aggcgcgcaa attacccaat cccgacacgg ggaggtagtg acgataaata ctgatacagg 420
gctcttttgg gtcttgtaat tggaatgagt acaatttaaa tcccttaacg aggaacaatt 480
ggagggcaag tctggtgcca gcagccgcgg taattccagc tccaatagcg tatattaaag 540
ttgttgtggt taaaaagctc gtagtagaac cttgggcctg gctggccggt ccgcctcacc 600
gcgtgcactg gtccggccgg gcctttccct ctgtggaacc gcatgccctt cactgggtgt 660
gccggggaaa caggactttt actttgaaaa aattagagtg ctccaggcag gcctatgctc 720
gaatacatta gcatggaata atagaatagg acgtgtggtt ctattttgtt ggtttctagg 780
accgccgtaa tgattaatag ggacagtcgg gggcatcagt attcaattgt cagaggtgaa 840
attcttggat ttattgaaga ctaactactg cgaaagcatt tgccaaggat gttttcattt 900
atcaggaacg aaagttaggg gatcgaagac gatcagatac cgtcgtagtc ttaaccataa 960
actatgccga ctagggatcg gacgatgtta ttttttgact cgttcggcac cttacgagaa 1020
atcaaagtgc ttgggctcca gggggagtat ggtcgcaagg ctgaaactta aagaaattga 1080
cggaagggca ccaccagggg tggagcctgc ggcttaattt gactcaacac ggggaaactc 1140
accaggtcca gacacaatga ggattgacag attgagagct ctttcttgat tttgtgggtg 1200
gtggtgcatg gccgttctta gttggtggag tgatttgtct gcttaattgc gataacgaac 1260
gagaccttaa cctgctaaat agcccgtatt gctttggcag tacgccggct tcttagaggg 1320
actatcggct caagccgatg gaagtttgag gcaataacag gtctgtgatg cccttagatg 1380
ttctgggccg cacgcgcgtt acactgacgg agccagcgag tactcccttg gccggaaggc 1440
ccgggtaatc ttgttaaact ccgtcgtgct ggggatagag cattgcaatt attgctcttc 1500
aacgaggaat ccctagtaag cgcaagtcat cagcttgcgt tgattacgtc cctgcccttt 1560
gtacacaccg cccgtcgcta ctaccgattg aatggctcag tgaggctttc ggactggccc 1620
agagaggtgg gcaactacca ctcagggccg gaaagttatc caaactcggt catttagag 1679
Claims (9)
1. phthalic acid ester shown in a kind of formula (I),
2. a kind of preparation method of phthalic acid ester described in claim 1, it is characterised in that the method are as follows: by ball anthrax-bacilus
The filtering fermentation liquor or centrifugation that the fermented culture of (Colletotrichum coccodes) ZZP-L1 obtains, take filtrate or supernatant
Liquid ethyl acetate or methylene chloride extraction, take organic layer to be concentrated into no liquid outflow, the inverted high performance liquid chromatography of concentrate
It isolates and purifies, collects the 6th minute peak, remove solvent, obtain phthalic acid ester shown in formula (I)；The ball anthrax-bacilus ZZP-
L1 is preserved in China Committee for Culture Collection of Microorganisms's common micro-organisms center, the deposit date is on June 28th, 2018,
Deposit number is CGMCC No:16083, and address: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3 Chinese Academy of Sciences microorganism is ground
Study carefully institute, postcode 100101.
3. preparation method as claimed in claim 2, it is characterised in that reversed-phase high performance liquid chromatography purification condition are as follows: liquid phase
Instrument UV-VIS, detector are Shimadzu SPD-10AV, and efficient liquid phase infusion pump is Shimadzu LC-10AD；Chromatographic condition: C18Chromatographic column
250 × 9.4mm, flow velocity 3.0mL/min, 30 DEG C of column temperature, Detection wavelength 203nm；Flow double steamings of phase composition volume ratio 10:90
Water: acetonitrile.
4. preparation method as claimed in claim 2, it is characterised in that ball anthrax-bacilus ZZP-L1 fermentation culture conditions are as follows: by ball charcoal
Subcutaneous ulcer bacterium ZZP-L1 is seeded in fermentation medium, shaking table culture 8-15 days under the conditions of 200rpm, 28 DEG C, obtains fermentation liquid；Hair
Ferment culture medium final concentration composition are as follows: 100~200g/L of potato, 10~20g/L of sucrose, solvent are distilled water, and pH is natural.
5. preparation method as claimed in claim 4, it is characterised in that first carry out inclined-plane before ball anthrax-bacilus ZZP-L1 fermented and cultured
Culture and seed culture, then seed liquor is seeded to fermentation medium, the inclined-plane culture with the inoculum concentration of volumetric concentration 10%
Are as follows: ball anthrax-bacilus ZZP-L1 is seeded to slant medium, 28 DEG C incubator moisturizing culture 3~4 days, obtain thallus inclined-plane；Tiltedly
Face culture medium final concentration composition are as follows: sucrose 20g/L, potato 200g/L, 15~20g/L of agar, solvent are distilled water, natural pH
Value；The seed culture are as follows: seed culture medium is seeded to from one oese thallus of thallus inclined-plane picking, in 200rpm, 28 DEG C of items
Shaking table culture 3 days under part obtain seed liquor；The seed culture medium composition is formed with fermentation medium.
6. phthalic acid ester described in a kind of claim 1 is preparing the application in antibacterial agent.
7. application as claimed in claim 6, it is characterised in that the antibacterial agent is Candida albicans antibacterial agent.
8. the use as claimed in claim 7, it is characterised in that the Candida albicans is Candida albicans (Canidia
albicans)ATCC10231。
9. a kind of ball anthrax-bacilus (Colletotrichum coccodes) for producing phthalic acid ester described in claim 1
ZZP-L1 is preserved in China Committee for Culture Collection of Microorganisms's common micro-organisms center, and the deposit date is June 28 in 2018
Day, deposit number is CGMCC No.16083, and preservation address: the Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3 Chinese Academy of Sciences is micro-
Biological study institute, postcode 100101.
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| CN103014078A (en) * | 2012-11-16 | 2013-04-03 | 淮海工学院 | Method for extracting DEHP (di(2-ethylhexyl)phthalate) from fermentation product of ocean paenibacillus polymyxa L1-9 and application |
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| 葛永红 等: "厚皮甜瓜果皮中预合成抗菌物质的提取、分离和鉴定", 《食品工业科技》 * |
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