CN109251145B - Phthalate, and preparation method, strain and application thereof - Google Patents

Phthalate, and preparation method, strain and application thereof Download PDF

Info

Publication number
CN109251145B
CN109251145B CN201810994356.XA CN201810994356A CN109251145B CN 109251145 B CN109251145 B CN 109251145B CN 201810994356 A CN201810994356 A CN 201810994356A CN 109251145 B CN109251145 B CN 109251145B
Authority
CN
China
Prior art keywords
zzp
culture
fermentation
colletotrichum
phthalate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201810994356.XA
Other languages
Chinese (zh)
Other versions
CN109251145A (en
Inventor
章华伟
张玮月
王鸿
华熠
潘瑞
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang University of Technology ZJUT
Original Assignee
Zhejiang University of Technology ZJUT
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang University of Technology ZJUT filed Critical Zhejiang University of Technology ZJUT
Priority to CN201810994356.XA priority Critical patent/CN109251145B/en
Publication of CN109251145A publication Critical patent/CN109251145A/en
Application granted granted Critical
Publication of CN109251145B publication Critical patent/CN109251145B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi

Abstract

The invention discloses phthalate and a preparation method, a strain and application thereof, wherein fermentation liquor obtained by fermentation culture of Colletotrichum melegueta ZZP-L1 is filtered or centrifuged, filtrate or supernatant is extracted by ethyl acetate or dichloromethane, an organic layer is concentrated until no liquid flows out, the concentrate is separated and purified by reversed-phase high performance liquid chromatography, peaks of 6 th and 14 th minutes are respectively collected, and a solvent is removed to respectively obtain the phthalate shown as a formula (I) or a formula (II). The phthalate (I) has an inhibiting effect on Candida albicans (Candida albicans), can be used as a novel antibiotic, and is expected to be applied to preparation of medicaments for treating related diseases caused by the Candida albicans; the two phthalates are produced by fermenting the liquid of the colletotrichum gloeosporioides ZZP-L1, the operation process is simple, the period is short, the cost is low, and the source is ensured; the invention is synthesized by a biological method, and has no pollution to the environment.

Description

Phthalate, and preparation method, strain and application thereof
(I) technical field
The invention relates to two phthalates, a biological preparation method and application thereof, and a symbiotic fungus-Colletotrichum coccodes ZZP-L1 for producing the phthalates.
(II) background of the invention
The discovery of new antimicrobial drug lead compounds has been a focus of attention by medicinal chemists. The plant symbiotic bacteria are special microorganisms which live in the intercellular space or tissue of healthy plants, do not cause any obvious disease symptoms of host plants and form a reciprocal symbiotic relationship with the host. A large number of chemical studies show that the plant symbiotic fungi have rich chemical diversity and can metabolize compounds with unique chemical structures and remarkable biological activities. The living environment of the coastal plants is very special, and the symbiotic fungi of the coastal plants have different living and metabolic mechanisms with the terrestrial microorganisms. The method deeply develops the chemical research of the symbiotic bacteria of the coastal plants and has important significance for searching a guide with remarkable antibacterial effect. The phthalate is a common plasticizer, has the effect of interfering the endocrine system of a human body, and also has certain biological activities such as antibiosis and the like. At present, phthalic acid ester is mainly produced by chemical synthesis, and is prepared by esterifying phthalic anhydride and alcohol under the catalysis of acid, and although the yield is high, the production method has the problems of side reactions such as dehydration, oxidation and the like, unstable target products, difficult waste liquid treatment and the like.
Disclosure of the invention
The invention aims to provide phthalate, a biological preparation method and application thereof, and a symbiotic fungus-Colletotrichum coccoides ZZP-L1 for producing the phthalate.
The technical scheme adopted by the invention is as follows:
the invention provides phthalic acid ester shown in formula (I) or formula (II),
Figure BDA0001781535050000011
the invention also provides a preparation method of the phthalate, which comprises the following steps: filtering or centrifuging fermentation liquor obtained by fermenting and culturing the Colletotrichum melegueta ZZP-L1, extracting filtrate or supernatant with ethyl acetate or dichloromethane, concentrating an organic layer until no liquid flows out, separating and purifying the concentrate by reverse phase high performance liquid chromatography, respectively collecting peaks at 6 th and 14 th minutes, and removing the solvent to respectively obtain the phthalate shown in formula (I) or formula (II).
Further, the separation and purification conditions are as follows: a liquid phase instrument UV-VIS, a detector is Shimadzu SPD-10AV, and a high performance liquid phase infusion pump is Shimadzu LC-10 AD; chromatographic conditions are as follows: c18The chromatographic column is 250 multiplied by 9.4mm, the flow rate is 3.0mL/min, the column temperature is 30 ℃, and the detection wavelength is 203 nm; the mobile phase comprises double distilled water and acetonitrile in a volume ratio of 10: 90.
Further, the fermentation liquor is prepared by the following method:
(1) slant culture: inoculating the colletotrichum gloeosporioides strain ZZP-L1 to a slant culture medium, and performing moisture-preserving culture at 28 ℃ for 3-4 days to obtain a thallus slant; the final concentration of the slant culture medium is as follows: 20g/L of sucrose, 200g/L of potato, 15-20g/L of agar and distilled water as a solvent, wherein the pH is natural;
(2) seed culture: selecting one strain of the thallus from the thallus slope, inoculating the thallus to 100mL of seed culture medium, and performing shake culture at 200rpm and 28 ℃ for 3 days to obtain a seed solution; the final concentration of the seed culture medium is as follows: 100-200g/L of potato, 10-20g/L of cane sugar, distilled water as solvent and natural pH; preferably, the final concentration composition of the seed culture medium is as follows: 200g/L of potato, 20g/L of cane sugar and distilled water as a solvent, wherein the pH value is natural;
(3) fermentation culture: inoculating the seed solution obtained in the step (2) into 200mL of fermentation medium by an inoculation amount with the volume concentration of 10%, performing shake culture for 8-15 days at the temperature of 28 ℃ at 200rpm to obtain fermentation liquid, wherein the final concentration of the fermentation medium is the same as the seed culture medium.
In addition, the invention also provides application of the phthalate shown in the formula (I) in preparing an antibacterial agent, preferably the antibacterial agent is Candida albicans (Candida albicans), more preferably Candida albicans ATCC10231 antibacterial agent. The effective concentration of the phthalate of the formula (I) against Candida albicans (Candida albicans) was 50. mu.M.
The invention also relates to a Colletotrichum coccoides ZZP-L1 strain for preparing the phthalate, which is preserved in China general microbiological culture Collection center (CGMCC), the preservation date is 2018, 6 and 28 days, the preservation number is CGMCC No:16083, the address is as follows: : western road No.1, north chen west road, north kyo, chaoyang, institute of microbiology, china academy of sciences, zip code 100101.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a Colletotrichum coccineum ZZP-L1 for producing the phthalate;
(2) the phthalate (I) has an inhibiting effect on Candida albicans (Candida albicans), can be used as a novel antibiotic, and is expected to be applied to preparation of medicaments for treating related diseases caused by the Candida albicans;
(3) the two phthalates are produced by fermenting the liquid of the colletotrichum gloeosporioides ZZP-L1, the operation process is simple, the period is short, the cost is low, and the source is ensured;
(4) the invention is synthesized by a biological method, and has no pollution to the environment.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1 isolation and characterization of Colletotrichum coccoides (Colletotrichum coccodes) ZZP-L1
1. Isolation of Strain ZZP-L1
The final concentration of the slant culture medium (i.e., PDA culture medium) was composed of: 20g/L of sucrose, 200g/L of potato, 20g/L of agar, distilled water as a solvent and natural pH value.
The final concentration of the seed medium (i.e., PDB medium) consisted of: 200g/L of potato, 20g/L of cane sugar and distilled water as a solvent, and the pH value is natural.
The strain ZZP-L1 is obtained by first separating coastal plant Stephania amabilis (Rumex obliifolius Linn) by the Shiwa teacher of Zhejiang university of industry by adopting a common symbiotic bacteria separation technology (the specific operation refers to Bangladesh Journal of Pharmacology, 2012,7: 120-.
2. Identification of Strain ZZP-L1
(1) Morphological characteristics: inoculating ZZP-L1 strain to PDA culture medium, activating at 28 deg.C for 3-4 days, picking activated colony with inoculating loop, culturing at 28 deg.C. The ZZP-L1 strain grows slowly, the colony is initially white, the villi is thick, and then the color gradually changes from red to black from the middle. The hyphae are long and twisted, have a large number of branches and are short. Conidiophores are cylindrical and sometimes slightly curved or branched.
(2) Molecular biological identification
The 18S rDNA of the strain ZZP-L1 is extracted and amplified by a molecular biological means, and the nucleotide sequence is determined to be shown in SEQ ID NO.1 by a DNA second generation sequencing technology (Biomek NX).
According to the colony morphological characteristics of the strain ZZP-L1 and the analysis result (Clustal X and MEGA software analysis) of the 18S rDNA sequence (GenBank numbering MF376146), the strain ZZP-L1 is identified as Colletotrichum coccoides (Colletotrichum coccodes) named as Colletotrichum coccoides ZZP-L1, the strain is preserved in the China general microbiological culture Collection center (CGMCC), the preservation date is 28 days 6 months in 2018, the preservation number is CGMCC No.16083, the preservation address is Beijing City sunward region North Chen West Lu No.1 institute of China academy of sciences microbial research, No. 3, and the postal code is 100101.
Example 2: preparation of fermentation culture solution of Colletotrichum melegueta ZZP-L1
(1) Slant culture: inoculating the Colletotrichum melegueta ZZP-L1 to a slant culture medium, and performing moisture-preserving culture in an incubator at 28 ℃ for 3-4 days to obtain a thallus slant; the final concentration composition of the slant medium was the same as in example 1.
(2) Seed culture: selecting one strain of the thallus from the thallus slope, inoculating the thallus to a seed culture medium, and performing shake culture at the conditions of 200rpm and 28 ℃ for 3 days to obtain a seed solution; the final concentration composition of the seed medium was the same as in example 1.
(3) Fermentation culture: inoculating the seed solution obtained in the step (2) to a fermentation culture medium by an inoculation amount with the volume concentration of 10%, performing shake culture at the temperature of 28 ℃ and 200rpm for 10 days to obtain a fermentation culture solution, wherein the final concentration of the fermentation culture medium constitutes the same seed culture medium.
Example 3: extraction, separation and identification of two phthalic acid esters
1. Extraction and separation of two phthalic acid esters
Filtering the fermentation liquor obtained in the example 2, extracting the filtrate for 2 times at normal temperature by using ethyl acetate (volume ratio is 1:1), taking an upper layer organic phase, carrying out vacuum concentration at low temperature (35 ℃, 0.01MPa) until no liquid flows out, and drying at 40 ℃ to obtain a brown crude extract F; separating the crude extract F methanol solution by reversed phase high performance liquid chromatography (RP-HPLC), respectively collecting peaks at 6 th and 14 th minutes, and removing mobile phase at low temperature under vacuum (35 deg.C, 0.01MPa) to obtain compound (I) and compound (II).
Liquid phase apparatus: UV-VIS, detector: shimadzu SPD-10 AV; high-efficiency liquid-phase infusion pump: shimadzu LC-10 AD; chromatographic conditions are as follows: c18The chromatographic column is 250 multiplied by 9.4mm, the flow rate is 3.0mL/min, the column temperature is 30 ℃, and the detection wavelength is 203 nm; mobile phase composition double distilled water (a): acetonitrile (B) ═ 10:90 (volume ratio).
2. Structural characterization of Compound (I)
The obtained objective compound (I) was subjected to mass spectrometry and nuclear magnetic resonance spectroscopy.
(1) The mass spectrum data is: ESI-MS M/z 301[ M + Na ]]+(ii) a Determination of the formula C16H22O4(ii) a The nuclear magnetic data are shown in table 1.
Table 1: process for preparing compound (I)1H-NMR Nuclear magnetic data and attribution
Figure BDA0001781535050000041
In summary, the structural formula of the target product (I) is shown as the formula (I):
Figure BDA0001781535050000042
the compound was named: di-isobutyl phthalate (diisobutylphthalate).
3. Structural identification of Compound (II)
The obtained objective compound (II) was subjected to mass spectrometry and nuclear magnetic resonance spectroscopy.
The mass spectrum data is: ESI-MS M/z 391[ M + H ]]+、413[M+Na]+(ii) a Determination of the formula C24H38O4(ii) a The nuclear magnetic data is shown in Table 2.
TABLE 2 preparation of Compound (II)1H-NMR Nuclear magnetic data and attribution
Figure BDA0001781535050000051
In summary, the structural formula of the target product is shown as formula (II):
Figure BDA0001781535050000052
the compound was named: bis (6-methylheptyl) phthalate (10, 10' -dimethyl-diheptyl phthalate).
Example 4: evaluation of two phthalate antibacterial Activity
The activity of the two compounds was evaluated by concentration gradient dilution, 6 replicates for each assay, and the test pathogens included Escherichia coli (Escherichia coli) ATCC25922, Staphylococcus aureus (Staphylococcus aureus) ATCC 25923, and Candida albicans (Candida albicans) ATCC 10231.
The specific method comprises the following steps:
1. the three indicator bacteria are activated and then transferred into a liquid culture medium, the bacteria (escherichia coli and staphylococcus aureus) are inoculated into an LB culture medium (1000 mL of distilled water, 10g of tryptone, 5g of yeast extract, 10g of sodium chloride and natural pH value), and the culture is carried out for 24 hours at 37 ℃; culturing fungus (Candida albicans) in PD culture medium (1000 mL distilled water, 200g potato, 20g glucose, natural pH value) at 28 deg.C for 48 hr, and diluting with fresh culture medium to thallus density of 105-106cfu/mL of bacterial suspension for use.
2. Amikacin Sulfate (Amikacin Sulfate) was precisely weighed and dissolved in sterile water (100. mu.M), and Ampicillin Sodium (Ampicillin Sodium) and amphotericin B (Amphotericin B) were dissolved in dimethyl sulfoxide (100. mu.M) for further use.
3. Each sample solution was pipetted into a 96-well plate so that the volume of the sample solution in the first well was 200. mu.L and the initial concentration was 100. mu.M. After stirring uniformly, sucking 100 μ L from the first well and adding to the next well, and so on (adding 100 μ L of bacterial suspension in advance to the rest of wells except the first well), so that the sample concentration corresponding to each well is: 100. 50, 25, 12.5, 6.25, 3.125, 1.56, 0.78, 0.39, 0.195. mu.M. DMSO was used as a negative control (no test sample added), a blank medium was used as a blank (no DMSO and test sample added), and the drug was used as a positive control (amikacin sulfate, ampicillin sodium, or amphotericin B added). Culturing the bacteria at 37 ℃ for 24h, culturing the fungi at 28 ℃ for 48h, observing, detecting the light absorption value of the indicator bacteria culture solution at 600nm by using a microplate reader, recording data, analyzing the result, and performing 3 groups of experiments in parallel. The lowest concentration for inhibiting the growth of the indicator bacteria is found, namely the minimum inhibitory concentration of the compound, and the result is shown in table 3.
TABLE 3 MIC values for the inhibition of 3 pathogenic indicators by the compounds
Figure BDA0001781535050000061
The antibacterial activity evaluation result shows that the compound (I) has a certain growth inhibition effect on C.albican, and the compound (II) has no growth inhibition activity on three pathogenic bacteria, so that the compound (I) has a certain application prospect in preparation of antibacterial agents.
Sequence listing
<110> Zhejiang industrial university
<120> phthalate, preparation method thereof, bacterial strain and application
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 1679
<212> DNA
<213> Colletotrichum coccodes (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 (7)

1. A preparation method of phthalate shown in formula (I) is characterized by comprising the following steps: filtering or centrifuging fermentation liquor obtained by fermenting and culturing the Colletotrichum melegueta ZZP-L1, extracting filtrate or supernatant with ethyl acetate or dichloromethane, concentrating an organic layer until no liquid flows out, separating and purifying the concentrate by reversed-phase high performance liquid chromatography, collecting the peak at the 6 th minute, and removing the solvent to obtain phthalate shown in the formula (I); the anthrax coccobacillus ZZP-L1 is preserved in China general microbiological culture Collection center of China Committee for culture Collection of microorganisms, the preservation date is 2018, 6 and 28 days, the preservation number is CGMCC No.16083, and the address: the microbial research institute of the national academy of sciences, No. 3, west road, north west of the area facing the sun, beijing, zip code 100101;
Figure FDA0002802870150000011
2. the method according to claim 1, wherein the conditions for separation and purification by reverse phase high performance liquid chromatography are as follows: a liquid phase instrument UV-VIS, a detector is Shimadzu SPD-10AV, and a high performance liquid phase infusion pump is Shimadzu LC-10 AD; chromatographic conditions are as follows: c18The chromatographic column is 250 multiplied by 9.4mm, the flow rate is 3.0mL/min, the column temperature is 30 ℃, and the detection wavelength is 203 nm; the mobile phase comprises double distilled water and acetonitrile in a volume ratio of 10: 90.
3. The process according to claim 1, wherein the fermentation conditions of Colletotrichum sphaericum ZZP-L1 are: inoculating the Colletotrichum melegueta ZZP-L1 into a fermentation medium, and performing shake culture at the temperature of 28 ℃ and the rpm of 200 for 8-15 days to obtain a fermentation liquid; the final concentration of the fermentation medium is as follows: 100-200g/L of potato, 10-20g/L of cane sugar, distilled water as a solvent and natural pH.
4. The method according to claim 3, wherein before fermentation culture, the Colletotrichum melegueta ZZP-L1 is subjected to slant culture and seed culture, and then the seed solution is inoculated to the fermentation medium in an inoculum size of 10% by volume concentration, wherein the slant culture is: inoculating the Colletotrichum mellea ZZP-L1 to a slant culture medium, and carrying out moisture-preserving culture in an incubator at 28 ℃ for 3-4 days to obtain a thallus slant; the final concentration composition of the slant culture medium is as follows: 20g/L of sucrose, 200g/L of potato, 15-20g/L of agar, distilled water as a solvent and natural pH value; the seed culture comprises the following steps: selecting one strain of the thallus from the thallus slope, inoculating the thallus to a seed culture medium, and performing shake culture at the conditions of 200rpm and 28 ℃ for 3 days to obtain a seed solution; the seed culture medium composition is the same as the fermentation culture medium composition.
5. An application of phthalate shown in formula (I) in preparing candida albicans antibacterial agent,
Figure FDA0002802870150000021
6. the use according to claim 5, wherein said Candida albicans is Candida albicans ATCC 10231.
7. The anthrax (ZZP-L1) strain for producing phthalate shown in formula (I) is preserved in China general microbiological culture Collection center (CGMCC), the preservation date is 2018, 6 months and 28 days, the preservation number is CGMCC No.16083, and the preservation address is as follows: the microbial research institute of the national academy of sciences, No. 3, west road, north west of the area facing the sun, beijing, zip code 100101;
Figure FDA0002802870150000022
CN201810994356.XA 2018-08-29 2018-08-29 Phthalate, and preparation method, strain and application thereof Active CN109251145B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810994356.XA CN109251145B (en) 2018-08-29 2018-08-29 Phthalate, and preparation method, strain and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810994356.XA CN109251145B (en) 2018-08-29 2018-08-29 Phthalate, and preparation method, strain and application thereof

Publications (2)

Publication Number Publication Date
CN109251145A CN109251145A (en) 2019-01-22
CN109251145B true CN109251145B (en) 2021-02-02

Family

ID=65048953

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810994356.XA Active CN109251145B (en) 2018-08-29 2018-08-29 Phthalate, and preparation method, strain and application thereof

Country Status (1)

Country Link
CN (1) CN109251145B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN105733148A (en) * 2016-04-27 2016-07-06 苏州圣谱拉新材料科技有限公司 Antibacterial water treatment material and preparing method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN105733148A (en) * 2016-04-27 2016-07-06 苏州圣谱拉新材料科技有限公司 Antibacterial water treatment material and preparing method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
厚皮甜瓜果皮中预合成抗菌物质的提取、分离和鉴定;葛永红 等;《食品工业科技》;20110801;第32卷(第8期);第98-104页 *

Also Published As

Publication number Publication date
CN109251145A (en) 2019-01-22

Similar Documents

Publication Publication Date Title
CN109957515B (en) Phomopsis strain and application thereof in biotransformation of tripterine
CN104277982B (en) Tricyclic sesquiterpenoid compound as well as preparation method and applications thereof
CN107964557B (en) Fermentation method for increasing yield of antibacterial lipopeptide of bacillus
CN110776518B (en) Azaphilone spiro compounds and preparation method and application thereof
CN114606134A (en) Sponge epiphyte and application thereof in preparation of oxaanthraquinone compounds
CN103255061A (en) Penicillium griseofulvum, antibacterial active compound generated thereby and application
CN106810601B (en) Destruxin depsipeptide derivative and preparation method and application thereof
CN112795609B (en) Method for efficiently preparing cyclodepsipeptide, cyclodepsipeptide and application
CN103408550B (en) Derive from 2,5-diketopiperazines dipeptides and the Synthesis and applications thereof producing the molten bacillus of enzyme
CN109251145B (en) Phthalate, and preparation method, strain and application thereof
CN107686817B (en) Chrysanthemum bud endophytic fungus CYSK-4 and application of Ascomylactam compound produced by same
CN114317290B (en) Bacterial strain capable of degrading diuron and application thereof
CN113444131B (en) N-acetylglucosamine compounds, and preparation method and application thereof
CN106701602B (en) Fusarium chlamydosporia and application thereof
CN113621526B (en) Marine fungus aspergillus versicolor M-7-SW9, mixed source terpenoid and extraction method and application thereof
CN108794502B (en) Trichothecene compound and preparation method and application thereof
CN109182216B (en) Marine streptomyces SCFJ-05 with inhibition effect on succulent plant stem rot
CN108486011B (en) Terphenyl compound, preparation method and application thereof
CN108503534B (en) Extraction method and application of p-hydroxybenzoic acid
CN110642823A (en) Pyran derivative and preparation method and application thereof
CN106397459B (en) Thio diketopiperazine compound and its application
CN113278545B (en) Streptomyces mutant and application thereof
CN113493750B (en) Marine actinomycetes and application thereof
CN113980821B (en) Aspergillus niger capable of converting hesperidin and application thereof
CN117510441B (en) Ketone compound penlactone A with plant pathogen resisting activity and preparation method thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant