CN106946955A - 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 - Google Patents
真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 Download PDFInfo
- Publication number
- CN106946955A CN106946955A CN201710154256.1A CN201710154256A CN106946955A CN 106946955 A CN106946955 A CN 106946955A CN 201710154256 A CN201710154256 A CN 201710154256A CN 106946955 A CN106946955 A CN 106946955A
- Authority
- CN
- China
- Prior art keywords
- fungi
- category
- compound
- preventing
- medicine
- 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
- 241000233866 Fungi Species 0.000 title claims abstract description 65
- 239000003814 drug Substances 0.000 title claims abstract description 27
- 208000031888 Mycoses Diseases 0.000 title claims abstract description 19
- -1 saccharide ester compound Chemical class 0.000 title claims abstract description 11
- 241000196324 Embryophyta Species 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 18
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 229940125904 compound 1 Drugs 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 10
- 235000020971 citrus fruits Nutrition 0.000 claims description 7
- 241000207199 Citrus Species 0.000 claims description 5
- 240000008790 Musa x paradisiaca Species 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229940126214 compound 3 Drugs 0.000 claims description 5
- 229940125898 compound 5 Drugs 0.000 claims description 5
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 4
- 241000223218 Fusarium Species 0.000 claims description 4
- 235000018290 Musa x paradisiaca Nutrition 0.000 claims description 4
- 241000233614 Phytophthora Species 0.000 claims description 4
- 241000223600 Alternaria Species 0.000 claims description 3
- 241001465180 Botrytis Species 0.000 claims description 3
- 235000004936 Bromus mango Nutrition 0.000 claims description 3
- 244000241235 Citrullus lanatus Species 0.000 claims description 3
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 claims description 3
- 241000222199 Colletotrichum Species 0.000 claims description 3
- 241000223208 Curvularia Species 0.000 claims description 3
- 241000223211 Curvularia lunata Species 0.000 claims description 3
- 241000371644 Curvularia ravenelii Species 0.000 claims description 3
- 241000159512 Geotrichum Species 0.000 claims description 3
- 235000017388 Geotrichum candidum Nutrition 0.000 claims description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 3
- 240000007228 Mangifera indica Species 0.000 claims description 3
- 235000014826 Mangifera indica Nutrition 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 241000228143 Penicillium Species 0.000 claims description 3
- 241000122123 Penicillium italicum Species 0.000 claims description 3
- 241001361634 Rhizoctonia Species 0.000 claims description 3
- 240000003768 Solanum lycopersicum Species 0.000 claims description 3
- 235000009184 Spondias indica Nutrition 0.000 claims description 3
- 241000562399 Ustilaginoidea Species 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 241000198596 Alternaria tomatophila Species 0.000 claims description 2
- 241001443921 Phytophthora litchii Species 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 208000024386 fungal infectious disease Diseases 0.000 claims 2
- 244000168141 Geotrichum candidum Species 0.000 claims 1
- 241000091506 Pezicula sp. Species 0.000 abstract description 11
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 8
- 241001138405 Taxodium distichum Species 0.000 abstract description 4
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 150000001768 cations Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 4
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940089256 fungistat Drugs 0.000 description 4
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241001269238 Data Species 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 241000453701 Galactomyces candidum Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000012271 agricultural production Methods 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000009629 microbiological culture Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 229930000044 secondary metabolite Natural products 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- AMNAZJFEONUVTD-KEWDHRJRSA-N (2s,3s,4s,5r,6r)-6-(4-amino-2-oxopyrimidin-1-yl)-4,5-dihydroxy-3-[[(2s)-3-hydroxy-2-[[2-(methylamino)acetyl]amino]propanoyl]amino]oxane-2-carboxamide Chemical compound O1[C@H](C(N)=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CNC)[C@H](O)[C@@H](O)[C@@H]1N1C(=O)N=C(N)C=C1 AMNAZJFEONUVTD-KEWDHRJRSA-N 0.000 description 1
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 244000153158 Ammi visnaga Species 0.000 description 1
- 235000010585 Ammi visnaga Nutrition 0.000 description 1
- 241000228438 Bipolaris maydis Species 0.000 description 1
- 241000555706 Botryosphaeria dothidea Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 241001529387 Colletotrichum gloeosporioides Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000595503 Geotrichum citri-aurantii Species 0.000 description 1
- 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 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- FEACDOXQOYCHKU-UHFFFAOYSA-N Gougerotin Natural products CNCC(=O)NC1=NC(=O)N(C=C1)C2OC(C(O)C(NC(=O)C(N)CO)C2O)C(=O)N FEACDOXQOYCHKU-UHFFFAOYSA-N 0.000 description 1
- 231100000678 Mycotoxin Toxicity 0.000 description 1
- 244000183278 Nephelium litchi Species 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 238000012408 PCR amplification Methods 0.000 description 1
- 241001546987 Pezicula cinnamomea Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 101100213970 Schizosaccharomyces pombe (strain 972 / ATCC 24843) ypt3 gene Proteins 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 208000035199 Tetraploidy Diseases 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241001474928 Ustilaginoidea virens Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002636 mycotoxin Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 150000003625 trehaloses Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3562—Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Nutrition Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用。本发明从落羽杉枝条内生菌中分离得到无柄盘菌(Pezicula sp.)SC1337，其能够产生五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，因此可以用其制备这五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，用于植物致病真菌的防治和水果的保鲜，具有广阔的应用前景。
Description
技术领域
本发明属于天然产物领域，具体涉及真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用。
背景技术
植物病害一直是农作物优质高产的重要制约因素之一。在植物病害中，70％～80％的病害是病原真菌侵染所引致的。植物真菌病害不仅直接造成农作物产量下降，农产品贮藏和运输期间大量腐烂变质，造成重大损失，而且部分病原真菌在侵染农作物和农产品过程中，可分泌产生多种对人畜有害的真菌毒素与有害代谢物，对农产品的安全性构成极大威胁。目前，农作物真菌病害的控制往往依赖化学防治，杀菌剂的使用不仅增大生产成本，而且其反复施用不可避免地带来环境污染与农产品农药残留问题。我国主要农作物重大真菌病害的化学防治主要依赖少数杀菌剂，病原真菌生产抗药性而导致杀菌剂丧失防治效果的风险性较高。因此，研发新型、高效的真菌抑制剂意义重大。
传统的化学合成的真菌抑制剂由于长期大量使用，病原菌产生部分抗药性，造成药效减弱，且在环境中不易分解，残留药剂会流失到周围环境中，对农林业生态系统及人类健康造成危害。而天然产物真菌抑制剂对防治对象多有较高选择性，且易于降解，残留较低，对人、畜和有益生物相对安全，环境污染较小，是近年植物病害防治研究的重点之一。目前常用的农用真菌抑制剂如井冈霉素、春雷霉素、多抗霉素、中生霉素、宁南霉素和申嗪霉素等，均来源于环境微生物(主要是植物根际土壤防线菌)次生代谢产物，来自真菌的较少。然而，植物内生真菌次生代谢产物种类丰富、结构多样，也是研发微生物源新型、高效的真菌抑制剂的重要资源。
发明内容
本发明的第一个目的是提供五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的三糖酯化合物。
本发明的三糖酯化合物，其为化合物1、2、3、4或5，所述的化合物1的结构式如式1所示，化合物2的结构式如式2所示，化合物3的结构式如式3所示，化合物4的结构式如式4所示，化合物5的结构式如式5所示，
本发明第二个目的是提供了上述化合物1、2、3、4或5在制备防治真菌病害药物中的应用。
所述的防治真菌病害药物是防治植物真菌病害药物。
一种防治植物真菌病害药物，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
优选，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌、Ustilaginoidea属真菌的药物。
所述的防治植物真菌病害药物是防治番茄早疫病、苹果轮纹病、番茄灰霉病、芒果炭疽病、香蕉新月弯孢霉、香蕉、西瓜枯萎病、柑橘白地霉病、玉米小斑病、柑橘青霉病、荔枝霜疫霉、水稻纹枯病或稻曲病的药物。
本发明第三个目的是提供化合物1、2、3、4或5在制备水果保鲜剂中的应用。
一种水果保鲜剂，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
优选，所述的水果保鲜剂为柑橘保鲜剂。
本发明从落羽杉枝条内生菌中分离得到无柄盘菌SC1337，其能够产生五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，因此可以用其制备这五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，用于植物致病真菌的防治和水果的保鲜，具有广阔的应用前景。
无柄盘菌(Pezicula sp.)SC1337于2017年2月15日保藏在广东省微生物菌种保藏中心(简称为GDMCC，地址：广州市先烈中路100号大院59号楼广东省微生物研究所，邮编：510070)，保藏号为GDMCC No：60144。
附图说明：
图1是无柄盘菌(Pezicula sp.)SC1337的菌落形态。
图2是无柄盘菌(Pezicula sp.)SC1337菌丝和孢子形态。
具体实施方式：
以下实施例是对本发明的进一步说明，而不是对本发明的限制。
实施例1：
本发明的无柄盘菌(Pezicula sp.)SC1337是从华南植物园的落羽杉枝条内生菌中分离获得，分离方法为：将采集好的落羽杉枝条样品经75％乙醇表面消毒30s，再经质量分数10％次氯酸钠消毒3min，无菌水冲洗3遍后晾干，接种至PDA培养基上，放至28℃培养箱培养5d，用无菌牙签挑取目标菌落即得，所述PDA培养基每升含马铃薯浸提物6g，葡萄糖20g，琼脂20g，其余为水，pH 6.0～6.5，由此分离得到无柄盘菌(Pezicula sp.)SC1337。
无柄盘菌(Pezicula sp.)SC1337的分类学特征：无柄盘菌(Pezicula sp.)SC1337的菌丝宽2～3μm；孢子长椭圆形，大小为14～22×4～6μm，菌落形态和菌丝(含孢子)的形态如图1和图2所示。菌丝体以经典的CTAB法提取得到DNA，通过以ITS4(5’-3’)：TCC TCC GCTTAT TGA TAT GC和ITS5(5’-3’)：GGA AGT AAA AGT CGT AAC AAG G为引物，在10×PCRbuffer 5μL，Mg2+(25mM)4μL，dNTPs(10mM)1μL，Primers(10μM/each)2μL，Taq酶(5U/μL)0.3μL，模板DNA(10ng/μL)5μL，ddH2O 32.7μL的体系中，在94℃5min，94℃40s，57-52℃1min，72℃1min，cycles 35，72℃6min程序下进行PCR扩增后，经测序得到的DNA核苷酸序列如SEQID NO.1所示。测序结果在Genbank数据库用Blast进行检索和同源性比较，其ITS序列片段(共917bp)同源性与Pezicula cinnamomea的同源性最高，ITS相似性为96％。因此将此菌命名为：无柄盘菌(Pezicula sp.)SC1337，于2017年2月15日保藏在广东省微生物菌种保藏中心(简称为GDMCC，地址：广州市先烈中路100号大院59号楼广东省微生物研究所，邮编510070)，保藏号为GDMCC No：60144。
实施例2：5种三糖酯衍生物的制备及其理化和波谱数据：
将无柄盘菌(Pezicula sp.)SC1337在小麦固体培养基(质量比1:1.5的小麦和水混合组成)上，黑暗中于28℃静置培养12d，得到固体发酵培养物。
将固体发酵培养物(3.6L)用等体积的体积分数95％乙醇水溶液浸泡三次，每次48h，浸泡液合并后过滤，然后减压浓缩除去乙醇，并加水定容至1L，再用等体积乙酸乙酯萃取3次，将得到的乙酸乙酯萃取物合并后，再浓缩得到乙酸乙酯提取物17.6g。
乙酸乙酯提取物上硅胶柱(硅胶为100～200目，300g)，以体积比90:10～70:30的氯仿-甲醇混合溶剂进行梯度洗脱，用薄层层析(硅胶板)检测合并相似的流份，收集薄层板上氯仿-甲醇体积比85:15展开时比移值0.3～0.4的流份，减压浓缩得流份A 1.69g，和比移值0.2～0.3的流份，减压浓缩得流份B 8.50g；
将流份A进行反相硅胶柱层析(Develosil ODS，75μm，150g，日本富士化学公司产品)，以体积分数88％的甲醇水溶液等度洗脱，收集主点集中的流份，合并后在高效液相色谱(LC-6AD型半制备高效液相色谱仪，RID-10A检测器，日本Shimadzu公司生产；层析柱为Shim-pack PRC-ODS，10×250mm，4.5μm)以体积分数88％的甲醇水溶液为流动相，流速为5ml/min，纯化得到白色粉末化合物5(0.030g，tR＝60min)。
取流份B 1.0g进行反相硅胶柱层析(Develosil ODS，75μm，150g)，以体积分数65％～85％的甲醇水溶液梯度洗脱，收集85％洗脱部分浓缩后经高效液相色谱(仪器和层析柱同前)，以体积分数87％的甲醇水溶液为流动相，流速为5ml/min，分离纯化得到四个白色粉末物质，分别为化合物1(0.122g，tR＝55min)，化合物2(0.120g，tR＝45min)，化合物3(0.010g，tR＝33min)和化合物4(0.122g，tR＝28min)。
化合物1，白色粉末，分子式为C41H72O19，正离子HRESIMS m/z 891.4552[M+Na]+(calcdfor C41H72O19Na,891.4560)，正离子ESIMS m/z 891[M+Na]+，907[M+K]+；负离子ESIMSm/z867[M－H]－，903[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物1为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-4-O-(8-甲基癸酰)-2-O-(4-甲基己酰)海藻糖，其结构式如式1所示。
其中化合物2，白色粉末，分子式为C40H70O19，正离子HRESIMS m/z 877.4411[M+Na]+(calcd for C40H70O19Na,877.4404)，正离子ESIMS m/z 877[M+Na]+；负离子ESIMS m/z853[M－H]－，889[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物2为4-O-癸酰-6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)海藻糖，其结构式如式2所示。
其中化合物3，白色粉末，分子式为C39H68O19，正离子HRESIMS m/z 863.4255[M+Na]+(calcd for C39H68O19Na,863.4247)，正离子ESIMS m/z 863[M+Na]+；负离子ESIMS m/z839[M－H]－，875[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物3为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)-4-O-(6-甲基辛酰)海藻糖，其结构式如式3所示。
其中化合物4，白色粉末，分子式为C38H66O19，正离子HRESIMS m/z 849.4088[M+Na]+(calcd for C38H66O19Na,849.4091)，正离子ESIMS m/z 849[M+Na]+；负离子ESIMS m/z825[M－H]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表2。通过以上光谱数据和二维核磁共振等方法鉴定化合物4为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)-4-O-辛酰海藻糖，其结构式如式4所示。
其中化合物5，白色粉末，分子式为C43H74O20，正离子ESIMS m/z 933[M+Na]+，949[M+K]+；负离子ESIMS m/z 909[M－H]－，945[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表2。通过以上光谱数据和二维核磁共振等方法鉴定化合物5为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-4-O-(8-甲基癸酰)-2-O-(4-甲基己酰)-6'-O-乙酰基海藻糖，其结构式如式5所示。
表1化合物1～3的1H和13C NMR数据
*相应位置的暂定信号可以互换
表2化合物4和5的1H和13C NMR数据
*相应位置的暂定信号可以互换
实施例3：实施例2得到的三糖酯(化合物1～5)的对植物常见12种科属的致病真菌的体外抑制活性试验
所用测试菌种包括：1)Alternaria solani番茄早疫病菌；2)Botryospuaeriaberengeriana苹果轮纹病菌；3)Botrytis cinerea番茄灰霉病菌；4)Colletotrichumgloeosporioides芒果炭疽病菌；5)Curvularia lunata香蕉新月弯孢霉；6)Fusariumoxysporium香蕉、西瓜枯萎病菌；7)Geotrichum citri-aurantii柑橘白地霉病菌；8)Helminthosporium maydis玉米小斑病菌；9)Penicillium italicum柑橘青霉病菌；10)Peronophythora litchii荔枝霜疫霉菌；11)Rhizoctonia solani水稻纹枯病菌；12)Ustilaginoidea virens稻曲病菌。
以滤纸片琼脂扩散法测定化合物1～5的抗真菌活性：将活化好的测试菌分别接种到装有PDA固体培养基的培养皿中，用T型涂布器涂均匀备用；待测试样品以甲醇溶解，配成50mg/mL，实验时取10μL滴加到滤纸片(直径为6mm)上，于超净工作台上晾干，使每滤纸片最终含有样品500μg，然后将滤纸片贴放于上述培养皿中，28℃黑暗条件下培养72或96h后测量抑菌宽度(抑菌宽度为抑菌圈平均直径)，以加入等体积甲醇的滤纸片作阴性对照。
结果显示三糖酯提取物和化合物1～5均可以抑制以上所有真菌的生长，抑菌圈宽度为10～22mm，显示出广谱的真菌抑制活性，结果见表3。所述三糖酯提取物为含有化合物1～4的混合物，其中化合物1、2、3、4质量比约为60:35:4:1。
表3三糖酯提取物和化合物1～5对12种植物致病真菌的体外抑制活性
实施例4：实施例2得到的三糖酯提取物对采后柑橘贮藏中保鲜实验
供试样品：实施例2得到的三糖酯提取物(含化合物1、2、3、4质量比约为60:35:4:1)以少量乙醇溶解，用水稀释为200、400、600mg/L作为处理溶液。
将柑橘果实在处理溶液中浸泡5min，晾干后，将果实置于经75％酒精表面灭菌晾干的塑料筐中，用0.02mm的聚乙烯薄膜袋包装密封，于25℃贮藏15天，观察并记录其感病指数，感病指数计算方法为：0为无明显感染；1为轻微感染；2为感染面积为果实的≤1/4；3为感染面积为果实的1/4-1/2；4为感染面积≥1/2，感病指数＝∑(感病等级×相应果实数量)/(5×果实总数量)×100％。每处理设3个重复，每重复用果约60个。
供试水果：砂糖橘采自从化果园。
实验结果如表4所示。该三糖酯提取物对采后柑橘贮藏过程中的真菌发生发展有明显的抑制作用，优于常用化学抗真菌剂福美双，与特克多相当，具有明显的防腐保鲜作用。该三糖酯提取物的抑菌保鲜效果略差于化学抗真菌剂百可得，但百可得由于毒性较高，2004年已被欧盟禁止使用。
表4三糖酯提取物对采后柑橘果实贮藏中对致病真菌的抑制活性
序列表
<110> 中国科学院华南植物园
<120> 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用
<160> 1
<210> 1
<211> 917
<212> DNA
<213> 无柄盘菌（Pezicula sp.）SC1337
<400> 1
CGAGGTCACC TTGATAGATT GGGGGTTGCT GGCCAGCATC CGCCGGGCGT CTGTAGCGAG 60
AGTATGTACT ACGCTTAGAG CCAGACGGCG CCGCCACTGA TTTTAAGGCA CACCGGGACC 120
GGTGACGCCC AAGACCAAGC AGAGCTTGAG GGTGTAATGA CGCTCGAACA GGCATGCCCC 180
CCGGAATACC AAGGGGCGCA ATGTGCGTTC AAAGATTCGA TGATTCACTG AATTCTGCAA 240
TTCACATTAC TTATCGCATT TCGCTGCGTT CTTCATCGAT GCCAGAACCA AGAGATCCGT 300
TGTTGAAAGT TTTAACTATT ATATAGTACT CAGACGACAC TGACATTCAG GTTTGGGAGT 360
CCTCTGGCGG GCGCGCCCTA GCCGGAGCCA GGGGCAGGGC CGGAGCCCCG CGGCCCGCCA 420
AAGCAACAAA GGTATAACGA CACAGGGTGG GAGGTCTACC CGAAGGGCAG AGTCTCTGTA 480
ATGATCCCTC CGCAGGTTCA CCTACGGAGC GGTTTACGTT CTTGCGAATC CCCAGCACGT 540
TTCCGCGCCG GCCCGACTAT ATCTTAAGCA GGAGAACCTC CTACCCACAA CCACTTAGTC 600
TGTGAACGTT CCCCTGGTCT AGGGGCTTCG CTGCGGATCG TCCATTCCAG CACCTGACTG 660
GATCCTCCGG GGTTGTTACT CTACCCTGTG CAGTTAACAC AGGCCCCTAC TGCATCCCTA 720
CAGTAGGTTA GTACCCAGAG GCTTTAGGAC TTCCCCGCAA TTCGATCGTG TTGCAACTCC 780
GCCGTTGGGC GTCGTCACTT GCGTGCCTCC TTATTTAGAG TCGCGAGAGC CCCCTTTCGG 840
GGTGCAAAGG CTTCCTCAAG TTCGCTGCAG AGAGATCACT GCTCTACGGA GACCTTGTAC 900
TTTTTTTTAT TACTTCC 917
Claims (9)
1.三糖酯化合物，其为化合物1、2、3、4或5，所述的化合物1的结构式如式1所示，化合物2的结构式如式2所示，化合物3的结构式如式3所示，化合物4的结构式如式4所示，化合物5的结构式如式5所示，
2.权利要求1中的化合物1、2、3、4或5在制备防治真菌病害药物中的应用。
3.根据权利要求2所述的应用，其特征在于，所述的防治真菌病害药物是防治植物真菌病害药物。
4.根据权利要求3所述的应用，其特征在于，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌或Ustilaginoidea属真菌的药物。
5.一种防治植物真菌病害药物，其特征在于，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
6.根据权利要求5所述的防治植物真菌病害药物，其特征在于，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌或Ustilaginoidea属真菌的药物。
7.根据权利要求5所述的防治植物真菌病害药物，其特征在于，所述的防治植物真菌病害药物是防治番茄早疫病、苹果轮纹病、番茄灰霉病、芒果炭疽病、香蕉新月弯孢霉、香蕉、西瓜枯萎病、柑橘白地霉病、玉米小斑病、柑橘青霉病、荔枝霜疫霉、水稻纹枯病或稻曲病的药物。
8.权利要求1中的化合物1、2、3、4或5在制备水果保鲜剂中的应用。
9.根据权利要求8所述的应用，其特征在于，所述的水果保鲜剂为柑橘保鲜剂。
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710154256.1A CN106946955B (zh) | 2017-03-15 | 2017-03-15 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| PCT/CN2017/102047 WO2018166158A1 (zh) | 2017-03-15 | 2017-09-18 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| US16/322,947 US20190166835A1 (en) | 2017-03-15 | 2017-09-18 | Fungal Trisaccharide Ester Compounds and Use Thereof in Preparing Agents for Preventing and Controlling Plant Fungal Diseases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710154256.1A CN106946955B (zh) | 2017-03-15 | 2017-03-15 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106946955A true CN106946955A (zh) | 2017-07-14 |
| CN106946955B CN106946955B (zh) | 2019-06-21 |
Family
ID=59471988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710154256.1A Active CN106946955B (zh) | 2017-03-15 | 2017-03-15 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US20190166835A1 (zh) |
| CN (1) | CN106946955B (zh) |
| WO (1) | WO2018166158A1 (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018166158A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| WO2018166159A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
| CN110038019A (zh) * | 2019-05-27 | 2019-07-23 | 惠州学院 | 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用 |
| CN110511878A (zh) * | 2019-07-31 | 2019-11-29 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111887056B (zh) * | 2020-06-30 | 2022-11-01 | 阿克苏优能农业科技股份有限公司 | 促糖心防虫害的苹果果树调控剂及应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1269361A (zh) * | 2000-04-28 | 2000-10-11 | 吴忠 | 葡聚烯糖化合物及其合成方法与应用 |
| CN105506029A (zh) * | 2016-01-06 | 2016-04-20 | 西南大学柑桔研究所 | 用柑橘皮制备抗真菌果胶低聚糖的方法及其应用和柑橘保鲜方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE387457T1 (de) * | 2000-08-25 | 2008-03-15 | Eastman Chem Co | Verfahren zur herstellung von disaccharid und trisaccharid c6-c12 fettsäure-estern mit hohem alpha gehalt und materialien davon |
| CN106946955B (zh) * | 2017-03-15 | 2019-06-21 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| CN106867917B (zh) * | 2017-03-15 | 2019-06-21 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
-
2017
- 2017-03-15 CN CN201710154256.1A patent/CN106946955B/zh active Active
- 2017-09-18 WO PCT/CN2017/102047 patent/WO2018166158A1/zh active Application Filing
- 2017-09-18 US US16/322,947 patent/US20190166835A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1269361A (zh) * | 2000-04-28 | 2000-10-11 | 吴忠 | 葡聚烯糖化合物及其合成方法与应用 |
| CN105506029A (zh) * | 2016-01-06 | 2016-04-20 | 西南大学柑桔研究所 | 用柑橘皮制备抗真菌果胶低聚糖的方法及其应用和柑橘保鲜方法 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018166158A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| WO2018166159A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
| CN110038019A (zh) * | 2019-05-27 | 2019-07-23 | 惠州学院 | 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用 |
| CN110511878A (zh) * | 2019-07-31 | 2019-11-29 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
| CN110511878B (zh) * | 2019-07-31 | 2021-06-11 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018166158A1 (zh) | 2018-09-20 |
| US20190166835A1 (en) | 2019-06-06 |
| CN106946955B (zh) | 2019-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106946955B (zh) | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 | |
| CN106867917B (zh) | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 | |
| Rosa et al. | Diversity and biological activities of endophytic fungi associated with micropropagated medicinal plant Echinacea purpurea (L.) Moench | |
| Degani et al. | Diagnosis and control of Harpophora maydis, the cause of late wilt in maize | |
| CN108315267A (zh) | 短密木霉gsaamlshu-1及其应用 | |
| CN109844095B (zh) | 对植物寄生线虫具有杀线虫活性的黑曲霉f22菌株及其用途 | |
| CN104762230B (zh) | 防治作物储藏期黄曲霉菌及毒素的海藻希瓦氏菌及其应用 | |
| CN1248578C (zh) | 蒽醌衍生物作为防治植物病害农药的应用 | |
| CN104450580A (zh) | 放线菌素d的制备方法及其应用 | |
| CN105349455B (zh) | 一株马来西亚链霉菌及其应用 | |
| CN106701623A (zh) | 一株拮抗枸杞根腐病的萎缩芽孢杆菌及其应用 | |
| CN110622975B (zh) | 咪康唑在制备用于防治植物病原菌的杀菌剂中的应用 | |
| Wang et al. | Bacillus amyloliquefaciens FG14 as a potential biocontrol strain against rusty root rot of Panax ginseng, and its impact on the rhizosphere microbial community | |
| CN108220211B (zh) | 一株嗜油不动杆菌nmb17及其在植物病害防治中的应用 | |
| de Carvalho et al. | Diversity and antimicrobial activity of culturable endophytic fungi associated with the neotropical ethnomedicinal plants Copaifera langsdorffii and Copaifera pubiflora | |
| Beed et al. | Biocontrol using Fusarium oxysporum: a critical component of integrated Striga management | |
| CN102027948B (zh) | 丰加霉素在防治黄瓜立枯病中的应用 | |
| Chu et al. | Effects of hexadecanoic acid on Fusarium oxysporum f. sp. niveum control and on growth of watermelon (Citrullus lanatus) | |
| CN111011384B (zh) | 8-羟基喹啉化合物在制备抗香蕉枯萎病和水稻稻曲病病原菌剂中的应用 | |
| Bakeer et al. | Field suppression of Fusarium soil borne diseases of Tomato plants by the combined application of bio agents and Chitosan | |
| CN113287621A (zh) | 咪唑衍生物a在制备防治香蕉枯萎病菌的农药杀菌剂的应用 | |
| Fayadh et al. | Effect of some microelements and biological control agents in control of tomato seedling damping-off caused by Rhizoctonia solani kuhn | |
| Jana et al. | Antagonistic effect of Trichoderma isolates on Sclerotium rolfsii. | |
| CN117511819B (zh) | 一株多粘类芽孢杆菌及其应用 | |
| Zhang et al. | Identification of a novel broad-spectrum anti-fungal strain of Pseudomonas aeruginosa (SU8) and effect of its crude metabolites against Rhizoctonia solani and Pyricularia oryzae. |
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 |