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Study On The Secondary Metabolites Of Streptomyces Scopuliridis And S.Glaucus

Posted on:2016-10-13Degree:MasterType:Thesis
Country:ChinaCandidate:R H LiuFull Text:PDF
GTID:2371330542986744Subject:Organic Chemistry
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Actinomycetes are extremely valuable resource for bioactive natural products.Currently,about 70%of the widely used antibiotics are produced by strains of actinomycetes,which have important significance in the pharmaceutical industry.Streptomycesbelongs to gram-positive bacteria and it could synthesis a large number of characteristic secondary metabolites.Those compounds derived from Streptomyces possess a broad range ofbiological activities,such as antimicrobial,antitumer,and enzyme-inhibiting activities.Currently,streptomyces has become an important source to find new lead compoundsThe fermentations of Streptomyces scopuliridis(YIM 32460)and Streptomyces glaucus(YIM 33872)have shown strong cytotoxic activity.In order to discover the novel lead drugs from streptomyces resource,we investigate systematicallysecondary metabolites of the two strains.Their fermentation broth was separated by a variety of chromatographic methods,including silica gel column chromatography,reverse silica gel column chromatography,sephadex LH-20 column chromatography,silica gel thin-layer chromatography and preparative HPLC method.The structures of these compounds were determined on the basis of spectral analysis.Nine compounds were isolated from the secondary metabolites of S.scopuliridis.They were elucidated as 6,10-epoxy-3,7,11-trimethyldodec-2-ene-1,7,11-triol(1*),(6R*,7 R*,10R*)-7,10-epoxy-3,7,11-trimethyldodec-2-ene-1,6,11-triol(2*),5-(6-hydroxy-6-methyl heptyl)-2(5H)-Furanone(3),5-(6-hydroxy-6-methyloctyl)-2-(5H)-Furanone(4),(+)-(2S,4S)-4-Hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydro-pyran(5),(1aR,7S,E)-7-ethylidene-la,2,3,4,4a,7-hexahydrocyclopenta[b]oxireno[2,3-c]pyridine(6),(1R,4aR,5R,7S,8aS)-5,8a-dime thyl-decahydronaphthalene-1,4a,7-tri-ol(7),(+)-(3S,5S,8E)-1,3,5-Trihydroxy-8-decene(8),and streptenol A(9).Eight compounds were isolated from the secondary metabolites of S.glaucus.The structures of these compounds were identified as 3,5,5-trimethyl-4-(3-oxobutyl)-2-cyclohexene-1-one(10),decahydro-2-(1-hydroxy-1-methylethyl)-4a,8-dimet hyl-1,5-naphthalenediol(11),1H-indole-3-acetamide(12),1H-pyrrole-2-carboxamide(13),5-(hydroxymethyl)-4-methoxy-3-methyl-2(5H)-furanone(14),(E)-3-(methylthio)-acrylic a cid(15),hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(16),and isatan(17).Among them,compound 1*and compound 2*are new compounds.In this topic,compositions of secondary metabolites from the two strains wereexp licitly put forward.These results provided experimental basis fordisco-very of theantitu mor lead compounds.
Keywords/Search Tags:Streptomyces, Streptomyces scopuliridis, Streptomyces glaucus, NMR spectraanalysis, chemical composition
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