CN116987052B - Butenolide derivative and preparation method and application thereof - Google Patents
Butenolide derivative and preparation method and application thereof Download PDFInfo
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- CN116987052B CN116987052B CN202310913259.4A CN202310913259A CN116987052B CN 116987052 B CN116987052 B CN 116987052B CN 202310913259 A CN202310913259 A CN 202310913259A CN 116987052 B CN116987052 B CN 116987052B
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- SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical class C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000855 fermentation Methods 0.000 claims abstract description 20
- 230000004151 fermentation Effects 0.000 claims abstract description 20
- 241000223602 Alternaria alternata Species 0.000 claims abstract description 18
- 241001247197 Cephalocarida Species 0.000 claims abstract description 12
- 241000233866 Fungi Species 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000001963 growth medium Substances 0.000 claims description 9
- 238000010898 silica gel chromatography Methods 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 238000004321 preservation Methods 0.000 claims description 8
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 4
- 239000002609 medium Substances 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000001888 Peptone Substances 0.000 claims description 3
- 108010080698 Peptones Proteins 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
- 244000061456 Solanum tuberosum Species 0.000 claims description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 3
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 3
- 239000004223 monosodium glutamate Substances 0.000 claims description 3
- 235000019319 peptone Nutrition 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000002953 preparative HPLC Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- 238000004659 sterilization and disinfection Methods 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 241001558165 Alternaria sp. Species 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 7
- 230000001665 lethal effect Effects 0.000 abstract description 4
- 229930014626 natural product Natural products 0.000 abstract description 4
- 241000223600 Alternaria Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000012271 agricultural production Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100031181 Glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 101100313266 Mus musculus Tead1 gene Proteins 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 229930000044 secondary metabolite Natural products 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 101150084750 1 gene Proteins 0.000 description 1
- KMEVEPGHUURWPL-UHFFFAOYSA-N Alternaric acid Natural products CCC(C)C(O)C(O)(C(O)=O)C=CCC(=C)CCC(=O)C1=C(O)CC(C)OC1=O KMEVEPGHUURWPL-UHFFFAOYSA-N 0.000 description 1
- 241000238582 Artemia Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 108091023242 Internal transcribed spacer Proteins 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 108010059820 Polygalacturonase Proteins 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000853 biopesticidal effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003278 egg shell Anatomy 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 210000001370 mediastinum Anatomy 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
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- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Insects & Arthropods (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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Abstract
The invention relates to the technical field of marine fungus natural products, in particular to a butenolide derivative, a preparation method and application thereof. The butenolide derivative is separated from a fermentation product of marine fungus Alternaria alternata YT-S-1, and has a structure shown in a formula (I) and is named Alternaria alternata acid A. The butenolide derivative alternaria alternata acid A obtained by the invention shows stronger artemia larva lethal activity and has the potential of developing a novel pesticide.
Description
Technical Field
The invention relates to the technical field of marine fungus natural products, in particular to a butenolide derivative, a preparation method and application thereof.
Background
With global warming and frequent extreme weather, the number of pest outbreaks in each year of agricultural production is gradually increased, and huge economic losses are brought to global agricultural production. However, in the agricultural pest control process, as the application amount of chemical pesticides is continuously increased, the high toxicity and non-targeting property of the chemical pesticides to beneficial organisms often cause greater ecological problems. Such as imbalance of the soil micro-ecological system, degradation of biological population, reduction of biological diversity, harm to human and livestock health caused by pesticide residues, and the like. Ultimately, serious hazards are created to the structure and function of the overall ecosystem. Thus, the search and development of environmentally friendly biopesticides from natural products from nature has been a hotspot for scientists to study. The microbial pesticide has the characteristics of high efficiency, safety, environmental compatibility, simple preparation process, easy mass production and the like, and has important strategic positions in agricultural pest control.
At present, products such as multi-antibiotics, validamycin, kasugamycin and the like from microorganism sources are widely applied to various links of agricultural production. The fungus source natural product has the advantages of large yield, novel structure, obvious activity, high creative coefficient and the like, and is always an important source of pesticide lead compounds. Therefore, the novel structure and the novel active secondary metabolite in fungi are deeply excavated, and the novel structure and the novel active secondary metabolite become the break-through for the research and development of novel microbial pesticides.
The butenolide derivative with insecticidal activity is obtained from a marine fungus, and a new source is provided for the development of green pesticides for controlling agricultural diseases and insect pests.
Disclosure of Invention
The invention aims to provide butenolide derivatives, and a preparation method and application thereof. The butenolide derivative alternaria alternata acid A obtained by the invention shows stronger artemia larva lethal activity and has the potential of developing a novel pesticide.
In order to achieve the above object, the present invention is realized by the following technical scheme:
A butenolide derivative, the structure of which is shown in formula (I):
。
the invention provides a preparation method of butenolide derivatives, which comprises the steps of inoculating Alternaria alternata YT-S-1 into a fungus culture medium for fermentation culture, and separating and purifying a fermentation product to obtain butenolide derivatives shown in a formula (I):
。
in the invention, the collection number of Alternaria alternata YT-S-1 is CCTCC NO: M2023660, the collection unit is China center for type culture Collection, the collection date is 2021, the collection address is China, the university of Wuhan and the university of Wuhan, and the classification name is Alternaria alternata, and the strain: YT-S-1.
The preparation method of the butenolide derivative comprises the following specific steps:
1) Inoculating Alternaria alternata YT-S-1 into an improved PDB culture medium for fermentation culture to obtain strain fermentation liquor;
the preparation method of the improved PDB culture medium comprises the following steps: 200g of potato is boiled, filtered by gauze, a filtrate part is taken, 20g of glucose, 6g of mannitol, 6g of sucrose, 3g of monosodium glutamate, 5g of peptone and 5g of yeast powder are added, the volume of purified water is fixed to 1L, after cooling to room temperature, the pH value is adjusted to 8.0-8.5, and high-pressure steam sterilization is carried out for 20min at 121 ℃;
2) Extracting the strain fermentation liquor collected in the step 1) by ethyl acetate, and concentrating under reduced pressure to obtain a fermentation liquor extract;
3) Subjecting the fermentation broth extract obtained in the step 2) to silica gel column chromatography, subjecting to gradient elution by petroleum ether-ethyl acetate (volume ratio of 50:1, 20:1, 10:1, 5:1, 2:1, 1:1, 0:1), and collecting each eluting component to obtain 7 groups of gradient eluting components;
preferably, the fermentation broth extract obtained in the step 2) is subjected to 200-300 mesh silica gel column chromatography.
4) Separating and purifying the petroleum ether-ethyl acetate eluting component with the volume ratio of 2:1 in the step 3) by reversed phase silica gel column chromatography (water-methanol system gradient elution with the volume ratio of 5:1-0:1) and semi-preparative high performance liquid chromatography (water-acetonitrile system gradient elution with the volume ratio of 3:2-1:2), thereby obtaining the butenolide derivative shown in the formula (I).
The invention also provides application of the butenolide derivative as an insecticide in development of biological pesticides; in particular to application in artemia larva control.
Compared with the prior art, the invention has the following advantages:
The butenolide derivative is obtained by fermenting, extracting and separating Alternaria alternata YT-S-1 separated from sponge, and the preparation method is simple, and the strain is easy to expand fermentation culture and is not limited by resources, regions and production conditions. Preliminary biological activity tests show that the compound has 100% lethal activity on artemia larvae at the concentration of 100 mug/mL, and shows good potential in insecticidal aspect.
Drawings
FIG. 1 is a diagram of strain morphological identification;
FIG. 2 is a graph of the hydrogen spectrum (500 MHz, CDCl 3) of butenolide derivatives obtained in the present invention;
FIG. 3 is a graph of the carbon spectrum (125 MHz, CDCl 3) of butenolide derivatives obtained in the present invention.
Detailed Description
The invention will be further described with reference to specific embodiments, and advantages and features of the invention will become apparent from the description. The embodiments are merely exemplary and do not limit the scope of the invention in any way. It will be understood by those skilled in the art that various changes and substitutions of details and forms of the technical solution of the present invention may be made without departing from the spirit and scope of the present invention, but these changes and substitutions fall within the scope of the present invention.
Example 1: identification of Alternaria alternata YT-S-1
The Alternaria alternata (Alternaria) YT-S-1 is obtained by separating from seawater in the peninsula river basin of Shandong in yellow sea, and has the preservation number of CCTCC NO: M2023660, the preservation unit of China center for type culture Collection, the preservation date of 2021, 04 month and 27 days, the preservation address of China, the university of Wuhan and the university of Wuhan, and the classification name of Alternaria asp-YT-S-1.
The Alternaria alternata YT-S-1 biological characteristics are: growing in PDA culture medium, and growing in 9 cm dishes for 5 days; the fungus drop is grey white, and hyphae are isolated; conidia with mediastinum can be produced under medium conditions as shown in figure 1. Ribosome transcriptional spacer sequences (internal transcribed spacer, ITS) were selected for amplification sequencing with elongation factors (translation elongation factor-alpha, TEF 1), glyceraldehyde-3-phosphate dehydrogenase gene (GLYCERALDEHYDE-3-phosphateehydrogenase, GAPDH), cohesive galacturonase gene (endopolygalacturonase, endoPG), alternaria allergen gene (ALTERNARIA MAJOR ALLERGEN GENE, alt al), and the obtained sequence information was analyzed by NCBI alignment (https:// www.ncbi.nlm.nih.gov) and identified as Alternariasp after five gene identifications (Table 1). Morphological identification was consistent with molecular identification results. The sequencing results of the five genes of ITS, TEF 1, GAPDH, endoPG and Alt al are shown as SEQ ID NO.1, SEQ ID NO.2, SEQ ID NO.3, SEQ ID NO.4 and SEQ ID NO. 5.
TABLE 1 Gene identification results Table
Example 2: butenolide derivative and preparation method thereof
The structural formula of the butenolide derivative is shown as the formula (I):
。
a preparation method of butenolide derivative shown in formula (I):
taking a good-growth Alternaria alternata YT-S-1 strain on a PDA flat plate, cutting into small blocks, inoculating into an improved PDB culture medium, wherein each 1L triangular flask contains 300mL of culture medium, standing and fermenting for 30 days at room temperature, extracting a strain fermentation liquor by using ethyl acetate, and concentrating under reduced pressure to obtain a fermentation liquor extract;
The preparation method of the improved PDB culture medium comprises the following steps: 200g of potato is boiled, filtered by gauze, a filtrate part is taken, 20g of glucose, 6g of mannitol, 6g of sucrose, 3g of monosodium glutamate, 5g of peptone and 5g of yeast powder are added, the volume of purified water is fixed to 1L, after cooling to room temperature, the pH is adjusted to 8.0, and high-pressure steam sterilization is carried out for 20min at 121 ℃.
Subjecting the crude extract to 300 mesh silica gel column chromatography, sequentially subjecting to gradient elution with petroleum ether-ethyl acetate with volume ratio of 50:1, 20:1, 10:1, 5:1, 2:1, 1:1 and 0:1, and collecting eluate of each polar section to obtain 7 components (1-7). Eluting component 5, namely petroleum ether-ethyl acetate eluting component with volume ratio of 2:1, by reverse phase silica gel column chromatography, eluting with water-methanol system with volume ratio of 5:1-0:1, collecting water-methanol eluting part with volume ratio of 3:7, gradient eluting with water-acetonitrile system with volume ratio of 3:2-1:2 by semi-preparative high performance liquid chromatography, and collecting single chromatographic peak. The structure of the compound is identified as a novel butenolide derivative through nuclear magnetic resonance spectrum analysis, and the structure is shown as a formula (I) and is named as Alternaria alternata acid A.
。
Test example 1: identification of Alternaria alternata acid A
Physicochemical and spectroscopic data for compound alternaric acid a:
Colorless oily liquid; [ alpha ] 17D-80 (c 0.10, meOH); the hydrogen spectrum (500 MHz, CDCl 3) of the butenolide derivative Alternaria acid A obtained by the invention is shown in figure 2, and the carbon spectrum (125 MHz, CDCl 3) of the butenolide derivative Alternaria acid A obtained by the invention is shown in figure 3.
Test example 2:
experiment of artemia resistance:
hatching artemia: placing 0.5g artemia cysts in a 1000mL beaker, adding 700mL of natural seawater, slowly inflating by a small inflator pump, incubating for 24 hours at room temperature, removing eggshells and unhatched eggs, and continuing inflating culture of artemia larvae for 24 hours for later use.
Artemia lethal activity test method: according to the Solis's modified method, 96-well cell culture plates were prepared by adding 190. Mu.L of seawater containing about 20 artemia larvae per well. The blank combination was set in three replicates for each concentration of sample group. The control group was added with 10. Mu.L of dimethyl sulfoxide (DMSO) solvent, the sample group was added with 10. Mu.L of a solution of butenolide derivative represented by formula (I) (DMSO is solvent), and after incubation for 24 hours at room temperature, the number of artemia dead individuals was counted by observation under a binocular dissecting mirror, and the mortality was calculated.
Experimental results show that the butenolide derivative has a mortality rate of 100% to artemia at a concentration of 100 mug/mL, and shows a strong insecticidal activity.
The foregoing is merely a preferred embodiment of the present invention, and several improvements and modifications to the present invention should be considered as the scope of the present invention for those skilled in the art.
Claims (10)
1. A butenolide derivative, which is characterized in that the structure of the butenolide derivative is shown as a formula (I):
。
2. The method for producing butenolide derivative according to claim 1, wherein the method comprises: inoculating Alternaria alternata YT-S-1 into a fungus culture medium for fermentation culture, and separating and purifying a fermentation product to obtain butenolide derivatives shown in a formula (I); the Alternaria alternata YT-S-1 has a preservation number of CCTCC NO: M2023660, a preservation unit of China center for type culture Collection, a preservation date of 2021, 04 months and 27 days, a preservation address of China university of Wuhan and Wuhan, and a classification designation of Alternaria sp.YT-S-1.
3. The preparation method according to claim 2, characterized by the specific steps of:
1) Inoculating Alternaria alternata YT-S-1 into a PDB culture medium for fermentation culture to obtain strain fermentation liquor;
2) Extracting the strain fermentation liquor collected in the step 1) by ethyl acetate, and concentrating under reduced pressure to obtain a fermentation liquor extract;
3) Subjecting the fermentation broth extract obtained in the step 2) to silica gel column chromatography, subjecting to gradient elution with petroleum ether-ethyl acetate, and collecting the eluting components to obtain 7 groups of gradient eluting components;
4) And (3) separating and purifying the petroleum ether-ethyl acetate eluting component with the volume ratio of 2:1 in the step (3) by reverse phase silica gel column chromatography and semi-preparative high performance liquid chromatography to obtain the butenolide derivative shown in the formula (I).
4. The method of claim 3, wherein the PDB medium in step 1) is a modified PDB medium, and the modified PDB medium is prepared by the following steps: 200g of potato is boiled, filtered by gauze, a filtrate part is taken, 20g of glucose, 6g of mannitol, 6g of sucrose, 3g of monosodium glutamate, 5g of peptone and 5g of yeast powder are added, the volume of purified water is fixed to 1L, after cooling to room temperature, the pH value is adjusted to 8.0-8.5, and high-pressure steam sterilization is carried out for 20min at 121 ℃.
5. The method according to claim 3, wherein the volume ratio of petroleum ether to ethyl acetate in the petroleum ether-ethyl acetate gradient elution in step 3) is sequentially 50:1, 20:1, 10:1, 5:1, 2:1, 1:1, 0:1.
6. The process according to claim 3, wherein in step 3), the fermentation broth extract obtained in step 2) is subjected to 200-300 mesh silica gel column chromatography.
7. The method according to claim 3, wherein the reversed-phase silica gel column chromatography in step 4) is carried out by gradient elution with a water-methanol system having a volume ratio of 5:1, 4:1, 3:1, 2:1, 0:1; and (3) performing gradient elution by a water-acetonitrile system with the volume ratio of 3:2, 2:2 and 1:2 in the high performance liquid chromatography.
8. An insecticide comprising the butenolide derivative according to claim 1.
9. An insecticide comprising the butenolide derivative prepared by the preparation method of any one of claims 2 to 7.
10. Use of the insecticide of claim 8 or 9 for controlling artemia larvae.
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