CN110982700A - Polyketide with anti-helicobacter pylori activity and preparation method and application thereof - Google Patents
Polyketide with anti-helicobacter pylori activity and preparation method and application thereof Download PDFInfo
- Publication number
- CN110982700A CN110982700A CN201911038386.4A CN201911038386A CN110982700A CN 110982700 A CN110982700 A CN 110982700A CN 201911038386 A CN201911038386 A CN 201911038386A CN 110982700 A CN110982700 A CN 110982700A
- Authority
- CN
- China
- Prior art keywords
- helicobacter pylori
- strain
- compound
- shsl21
- preparation
- 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.)
- Granted
Links
Images
Classifications
-
- 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
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/77—Fusarium
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Mycology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Botany (AREA)
- Rheumatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a Fusarium equiseti (Fusarium equiseti) strain Shsl21 with the preservation number of CGMCC No. 18550. The invention also provides a compound prepared by the strain Shsl21, which has better anti-helicobacter pylori (H.pylori BHKS159) activity and is suitable for research of anti-helicobacter pylori lead compounds or preparation of anti-helicobacter pylori medicaments.
Description
Technical Field
The present invention belongs to the field of polyketide compound technology with activity of resisting helicobacter pylori.
Background
Helicobacter pylori (Helicobacter pylori) is a microaerophilic spiral gram-negative bacterium which can be planted on gastric mucosa for a long time, the infection rate of the Helicobacter pylori reaches over 50% of the global population, China is also a country with higher infection rate, and the infection rate is 40-90% according to statistics. Helicobacter pylori is an important causative agent in the pathogenesis of chronic gastritis, streptococcal disease, gastric cancer and mucosa-associated lymphoid tissue lymphoma. The world health organization/international agency for research on cancer has listed helicobacter pylori as a human class i carcinogen. Therefore, the research and development of high-efficiency and low-toxicity helicobacter pylori medicines are in the forefront.
Disclosure of Invention
The invention aims to provide a compound with anti-helicobacter pylori activity, which has a structural formula shown as a formula I:
the second purpose of the invention is to provide a Fusarium equiseti strain Shsl21 which is preserved in the common microorganism center of China Committee for culture Collection of microorganisms (CGMCC for short, with the address of No. 3 Hospital No.1 West Lu of the sunward district in Beijing city) in 19 months in 2019, and the registration number of the preservation center is CGMCC No. 18550.
A third object of the present invention is to provide a method for preparing a compound, comprising the steps of:
activated strain Shsl 21;
a solid fermentation strain Shsl 21;
leaching the solid fermentation product with ethyl acetate to obtain a crude extract;
performing reduced pressure silica gel column chromatography to obtain eluate;
separating with reverse silica gel chromatography to obtain reverse eluate;
separating with gel chromatography to obtain gel eluate;
separating by reverse phase HPLC to obtain HPLC eluent.
The strain and the compound provided by the invention have better anti-helicobacter pylori (H.pylori BHKS159) activity, and are suitable for research of anti-helicobacter pylori lead compounds or preparation of anti-helicobacter pylori medicaments.
Drawings
FIG. 1 is a drawing of a compound1H nuclear magnetic resonance spectrum.
FIG. 2 is a drawing of a compound13C nuclear magnetic resonance spectrum.
Detailed Description
The following examples are given to facilitate a better understanding of the invention, but do not limit the invention. The experimental procedures in the following examples are conventional unless otherwise specified. The test materials used in the following examples were purchased from a conventional biochemical reagent store unless otherwise specified. The quantitative tests in the following examples were all set up for 3 replicates and the results were averaged.
Example 1
Isolation and characterization of Strain Shsl21
Collection and separation of strain Shsl21
A strain named as Shsl21 was isolated from flowers of the northern regional Tung-Hua tree in Guangxi defense harbor in 2015.
The strain Shsl21 is a mangrove endophytic fungus.
II, identification of strain Shsl21
1. Molecular identification
The partial sequence of 18S ribosomal RNA of the strain Shsl21 is shown in sequence 1 of the sequence table, for example, the sequence similarity of GENBANKACCESSION NO. MN443741 is the highest, and the similarity is 99%.
According to the above identification results, the strain Shsl21 belongs to Fusarium equiseti (Fusarium equiseti).
Third, preservation of Strain Shsl21
The strain Shsl21 belongs to Fusarium equiseti (Fusarium equiseti), and has been deposited in China general microbiological culture Collection center (CGMCC for short, with the address of CGMCC No. 3 of Beijing city Kogyo No.1 of North Chen West Lu of the Indormiton) in 19 months in 2019, and the preservation number is CGMCC No. 18550.
Example 2
Preparation of the Compounds
PDA culture medium: mixing potato 200g, glucose 20g, agar 15g and water 1000mL, and sterilizing with high pressure steam at 121 deg.C for 30 min.
Seed culture medium: glucose 4.0g, wort 10.0g, yeast extract 4.0g and water 1000mL were mixed well, pH was adjusted to 6.5, 50mL was added to each 250mL Erlenmeyer flask and sterilized at 121 ℃ for 30 min.
Rice culture medium: 80g of rice and 120mL of water were put into a 500mL Erlenmeyer flask, soaked overnight, and autoclaved at 121 ℃ for 30 min.
1 solid fermentation of Strain Shsl21
1.1 activation of Strain Shsl21
Culturing the strain Shsl21 on a PDA plate for 5 days, and after the colony grows to fill the plate, culturing 5 colonies with the length of 1cm2The pellet of the size was inoculated into a 250mL Erlenmeyer flask containing 50mL of seed medium together with the medium, and cultured on a shaker (25 ℃, 200rpm) for 7 days to serve as a seed culture solution.
1.2 solid fermentation of Strain Shsl21
Inoculating 5mL of seed culture solution into a triangular flask containing rice culture medium, and performing aseptic culture at 25 deg.C for 30 d.
2 extraction of the Compound
2.1 Add 1.0L of ethyl acetate to the flask (containing the solid fermentation) obtained in step 1.2, leach at room temperature for 24h, collect the first supernatant.
2.2 Add 1.0L of ethyl acetate again to the Erlenmeyer flask of step 2.1, leach at room temperature for 24h, collect the second supernatant.
2.3 Add 1.0L of ethyl acetate again to the Erlenmeyer flask of step 2.2, leach at room temperature for 24h, collect the third supernatant.
2.4 Add 1.0L of ethyl acetate again to the Erlenmeyer flask of step 2.3, leach at room temperature for 24h, collect the fourth supernatant.
2.5 the first supernatant of step 2.1, the second supernatant of step 2.2, the third supernatant of step 2.3 and the fourth supernatant of step 2.4 are combined and distilled to dryness under reduced pressure to give 14.0g of crude extract.
3. Separation and purification of compounds
3.1 vacuum silica gel column chromatography to obtain the eluent
And (3) carrying out reduced pressure silica gel column chromatography on the crude extract obtained in the step 2.5.
The types of the columns are as follows: 8 × 30 cm;
the fillers are: thin layer chromatography silica gel H and column chromatography silica gel (refined);
the elution process is as follows:
(1) eluting with 1000mL of eluent A (composed of 6 parts by volume of petroleum ether and 4 parts by volume of ethyl acetate) in sequence;
(2) eluting with 1000mL of eluent B (composed of 5 parts by volume of petroleum ether and 5 parts by volume of ethyl acetate);
(3) eluting with 1000mL of eluent C (composed of 4 parts by volume of petroleum ether and 6 parts by volume of ethyl acetate);
(4) eluting with 1000mL of eluent D (composed of 3 parts by volume of petroleum ether and 7 parts by volume of ethyl acetate);
(5) eluting with 1000mL of eluent E (consisting of 2 parts by volume of petroleum ether and 8 parts by volume of ethyl acetate);
the flow rate is 50mL/min, and the eluent A-E is collected after passing through the column.
3.2 reverse silica gel chromatographic separation of the chromatographic eluent to obtain reverse eluent
The parameters of the reverse silica gel chromatographic separation are as follows:
the types of the columns are as follows: 3 × 60 cm;
the fillers are: c18;
the mobile phase was 500mL eluent (composed of 6 parts by volume methanol and 4 parts by volume water) at a flow rate of 0.5 mL/min;
collecting the eluent in reverse direction after passing through the column.
3.3 subjecting the reverse eluent to gel chromatography to obtain a gel eluent
The parameters of the gel chromatographic separation are as follows:
the types of the columns are as follows: 3 × 60 cm;
the fillers are: sephadex LH-20;
the mobile phase is a methanol organic solvent with the percentage content of 100 percent, and the flow rate is 0.5 mL/min;
collecting the gel eluent with the retention volume of 80-100 mL.
3.4 reverse phase HPLC separation is carried out on the gel eluent to obtain HPLC eluent
The parameters of the reverse phase HPLC separation are as follows:
the types of the columns are as follows: a Kramosil C18 column (10 μm; 10X 250 mm);
the elution process is as follows: eluting with 57-59% methanol water solution for 30min at flow rate of 2 mL/min.
The collection retention time is 20.6-21.0min (retention time of peak value t)R20.8min) of the eluate after passing through the column.
3.5 distillation under reduced pressure of the HPLC eluent collected in step 3.4 to dryness gives 5.5mg of product.
4 confirmation of Compound
And (3) carrying out organic mass spectrometry and nuclear magnetic resonance spectrum analysis on the product of the step 3.5.
The characterization data of the product are as follows:
yellow needle-shaped;
the molecular formula is as follows: c14H20O6(ii) a Molecular weight: 284;
1the H nuclear magnetic resonance spectrum is shown in figure 1,13the C NMR spectrum is shown in FIG. 2;
based on the above characterization data and the physicochemical data and profile of the above compound, the product of step 3.5 is a compound of formula (I).
Example 3
Inhibitory Effect of the Compound represented by the formula (I) against helicobacter pylori (H.pylori BHKS159)
The minimum inhibitory concentration (MIC, 100 μ L system) of the compound represented by formula (I) against h.pylori BHKS159 was examined by microdilution.
Parallel experiments were performed with metronidazole (aladin) as a positive control for the compounds.
The bacteria used in this example were: anti-helicobacter pylori (h. pylori BHKS 159).
The experiment comprises the following specific steps:
1. preparation of MIC plates
Adding a brain heart extract culture medium (BHI) (specific components comprise peptone, dehydrated calf brain extract powder, dehydrated calf heart extract powder, sodium chloride, glucose and disodium hydrogen phosphate, and the pH value is 7.4) to 173.6 mu L of the BHI in the 1 st hole, adding 6.4 mu L of a compound to be detected, and diluting to the 7 th hole in a multiple ratio; no addition was made in well 8, and 90. mu.L of the medium was retained as a control with no addition of test compound.
2. Preparation of bacterial liquid
Preparing anti-helicobacter pylori (H.pylori BHKS159) growing in logarithmic phase on a solid plate into bacterial suspension by using BHI culture medium, and adjusting the concentration OD600Is 0.3 (1X 10)8CFU/mL), 10-fold dilution at 1X 107CFU/mL, spare.
3. Inoculated bacterial liquid
Adding 10 μ L into 1-8 th well (the concentration of bacteria liquid in each well is about 1.0 × 10)6CFU/mL). And culturing for 72h to judge the result. The compound concentrations in wells 1 to 7 were 64, 32, 16, 8, 4, 2, 1. mu.g/mL, respectively.
4. Result judgment
MIC is the lowest concentration of compound of formula (I) that completely inhibits bacterial growth in the wells.
The test is meaningful when the bacteria grow significantly in the 8 th well (i.e., no antibiotic) of the positive control well.
When a single jump hole occurs in the microdilution method, the highest concentration of the compound of formula (I) that inhibits bacterial growth should be recorded. If a plurality of jump holes appear, the result should not be reported, and the test needs to be repeated.
The bacteriostatic action of the compound of formula (I) against h.pylori BHKS159 was repeated 3 times.
The MIC value of the compound of formula (I) against H.pylori BHKS159 was 8. mu.g/mL.
Metronidazole has a MIC value against H.pylori BHKS159 of greater than 16 μ g/mL.
Sequence listing
<110> institute of microbiology of Chinese academy of sciences
<120> polyketide with anti-helicobacter pylori activity, and preparation method and application thereof
<160>1
<170>SIPOSequenceListing 1.0
<210>1
<211>481
<212>DNA
<213> Fusarium (Fusarium equiseti)
<400>1
acggcgtggc cgcgacgatc accagtaacg aggtgtatga ttactacgct atggaagctc 60
gacgtgaccg ccaatcgatt tggggaacgc gggttaccgc gagtcccaac accaagctga 120
gcttgagggt tgaaatgacg ctcgaacagg catgcccgcc agaatactgg cgggcgcaat 180
gtgcgttcaa agattcgatg attcactgaa ttctgcaatt cacattactt atcgcatttt 240
gctgcgttct tcatcgatgc cagaaccaag agatccgttg ttgaaagttt tgatttattt 300
gtttgtttta ctcagaagtt ccactaaaaa cagagtttag gggtcctcgg gcgggccgtc 360
ccgttttacg gggcgcgggc tgatccgccg aggcaacgta taggtatgtt cacaggggtt 420
tgggagttgt aaactcggta atgatccctc cgctggttca ccaacggaga ccttgttacg 480
a 481
Claims (5)
1. Fusarium equiseti (Fusarium equiseti) strain Shsl21 CGMCC No. 18550.
3. a process for the preparation of a compound according to claim 2, comprising the steps of:
activated strain Shsl 21;
a solid fermentation strain Shsl 21;
leaching the solid fermentation product with ethyl acetate to obtain a crude extract;
performing reduced pressure silica gel column chromatography to obtain eluate;
separating with reverse silica gel chromatography to obtain reverse eluate;
separating with gel chromatography to obtain gel eluate;
separating by reverse phase HPLC to obtain HPLC eluent.
4. Use of the compound of claim 2 for inhibiting anti-helicobacter pylori activity.
5. The use of claim 4, wherein the compound inhibits bacterial growth at a maximum concentration of 8 μ g/mL.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911038386.4A CN110982700B (en) | 2019-10-29 | 2019-10-29 | Polyketide with anti-helicobacter pylori activity and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911038386.4A CN110982700B (en) | 2019-10-29 | 2019-10-29 | Polyketide with anti-helicobacter pylori activity and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110982700A true CN110982700A (en) | 2020-04-10 |
CN110982700B CN110982700B (en) | 2021-11-12 |
Family
ID=70082521
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201911038386.4A Active CN110982700B (en) | 2019-10-29 | 2019-10-29 | Polyketide with anti-helicobacter pylori activity and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110982700B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112694406A (en) * | 2020-07-03 | 2021-04-23 | 中国地质大学(北京) | Preparation method and application of two dimeric hexyl itaconic acid derivatives |
CN114292193A (en) * | 2021-12-28 | 2022-04-08 | 浙江工业大学 | Depside cyclic ether compound, strain, preparation method and application |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109467579A (en) * | 2018-11-01 | 2019-03-15 | 海南大学 | A kind of PKS I type polyketides and its preparation method and application with immunosuppressive activity |
CN109553600A (en) * | 2018-12-04 | 2019-04-02 | 海南师范大学 | Isocoumarin class compound and the preparation method and application thereof in a kind of mangrove endogenetic fungus |
-
2019
- 2019-10-29 CN CN201911038386.4A patent/CN110982700B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109467579A (en) * | 2018-11-01 | 2019-03-15 | 海南大学 | A kind of PKS I type polyketides and its preparation method and application with immunosuppressive activity |
CN109553600A (en) * | 2018-12-04 | 2019-04-02 | 海南师范大学 | Isocoumarin class compound and the preparation method and application thereof in a kind of mangrove endogenetic fungus |
Non-Patent Citations (5)
Title |
---|
BURMEISTER等: "Antibiotic Produced by Fusarium equiseti NRRL 5537", 《ANTIMICROBIAL AGENTS AND CHEMOTHERAPY》 * |
CHUNYU等: "A new cyclohexenone from the tin mine tailingsderived fungus Aspergillus flavus YIM DT 10012", 《NATURAL PRODUCT RESEARCH》 * |
REGISTRY: "152204-32-5", 《STN数据库》 * |
YANG等: "Flavusides A and B, Antibacterial Cerebrosides from the Marine-Derived Fungus Aspergillus flavus", 《CHEM. PHARM. BULL.》 * |
ZHANG等: "Enzyme-catalysed [6+4] cycloadditions in the biosynthesis of natural products", 《NATURE》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112694406A (en) * | 2020-07-03 | 2021-04-23 | 中国地质大学(北京) | Preparation method and application of two dimeric hexyl itaconic acid derivatives |
CN114292193A (en) * | 2021-12-28 | 2022-04-08 | 浙江工业大学 | Depside cyclic ether compound, strain, preparation method and application |
CN114292193B (en) * | 2021-12-28 | 2024-04-12 | 浙江工业大学 | Depsipeptide cyclic ether compound, bacterial strain, preparation method and application |
Also Published As
Publication number | Publication date |
---|---|
CN110982700B (en) | 2021-11-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110982700B (en) | Polyketide with anti-helicobacter pylori activity and preparation method and application thereof | |
CN107475146A (en) | A kind of application of streptomycete and its metabolite piericidin class compound in anti-kidney | |
CN110951620B (en) | Compound for resisting activity of helicobacter pylori, preparation method and application thereof | |
CN112226470B (en) | Active substance for preventing and treating orobanche coerulescens, and extraction method and application thereof | |
CN110951619B (en) | Anthraquinone compound with anti-helicobacter pylori activity and application thereof | |
CN114380814B (en) | Oxazole siderophore compound and preparation method and application thereof | |
CN114380764B (en) | Thiazoline siderophore compound and preparation method and application thereof | |
CN113493750B (en) | Marine actinomycetes and application thereof | |
CN111748489B (en) | Marine streptomyces griseofulensis HN60 and application thereof | |
CN115109023A (en) | Macrolide compound FWYZ52-A, and fermentation strain, fermentation method and application thereof | |
CN110092758B (en) | Novel alkaloid compound and wart spore strain for preparing compound by fermentation | |
CN113881602A (en) | High yield C21Steroid compound bacillus cereus X-32 and application thereof | |
CN115466241B (en) | Compound with helicobacter pylori resisting activity and application thereof | |
CN114469908B (en) | Preparation method and application of acinetobacter baumanii-resistant compound stephol | |
CN110241029A (en) | One plant of coptis soil ferulic acid degradation bacteria and application thereof | |
CN112694406B (en) | Preparation method and application of two dimeric hexyl itaconic acid derivatives | |
CN112107602B (en) | A pair of twin-nitrogen containing alkaloid enantiomers, preparation and application thereof | |
CN113151000B (en) | Marine fungus and application thereof in production of dibutyl phthalate | |
CN113980819B (en) | Taxus chinensis needle leaf endophytic fungus strain and application thereof | |
CN118271277A (en) | Depsipeptide cyclic ether compounds with antibacterial activity and preparation method thereof | |
CN111320597B (en) | Anti-plant virus pyriminomycin and preparation process and application thereof | |
CN113173904B (en) | Novel bacteriostatic compounds and aspergillus for preparing the same | |
CN115247131B (en) | Trichoderma atroviride and metabolite and application thereof | |
CN116694478A (en) | Aspergillus strain and application of cyclic depsipeptide compound thereof | |
CN108424404B (en) | Compound for resisting sweet potato black spot germs as well as preparation method and application 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 |