Streptomycetes, which belong to the Gram-positive bacteria, produce secondary metabolites and sporulate. The timing of starting the secondary metabolite production and the sporulation depends on environmental conditions such as nitrogen and carbon sources. In order to obtain a tool for understanding the regulation mechanism, we carried out screening for chemical substances that induce secondary metabolism and sporulation in streptomycetes and found an active substance from the culture broth of Streptomyces sp. TP-A0584. This substance designated goadsporin promoted the formation of red pigment and sporulation at a concentration of 1 jim in Streptomyces lividans TK23 which does not produce the pigment under normal growth conditions. Goadsporin is an oligopeptide consisting of 19 amino acids with the molecular formula C72H97N19O20S2. Sporulation and/or secondary metabolite production was induced in 36 streptomycetes strains among 42 strains tested. These results suggest that goadsporin acts on a common regulation pathwayfor sporulation and secondary metabolism in streptomycetes and can be a powerful tool to analyze the regulation mechanism.
Alchivemycin A, a novel polycyclic polyketide, was isolated from the culture extract of a plant-derived actinomycete Streptomyces sp. The structure and relative configuration were elucidated by spectroscopic analysis and X-ray crystallography, and the absolute configuration was determined by a (1)H NMR anisotropy method using MPA ester derivatization. The new compound contains an unprecedented heterocyclic ring system, 2H-tetrahydro-4,6-dioxo-1,2-oxazine. Alchivemycin A showed potent antimicrobial activity against Micrococcus luteus and inhibitory effects on tumor cell invasion.
The structure of goadsporin was determined by using spectroscopic techniques. NMR analysis revealed that goadsporin consists of 19 amino acids, two of which are dehydroalanines (Deala), and six of which are cyclized to oxazoles (Oxz) and thiazoles (Thz) by dehydrative cyclization and dehydrogenation from serine, threonine and cysteine. NMR analysis established seven partial structures, and their sequence was determined by CID-MS/MS'. Negative mode FAB-MS/MS gave product ions arising from charge-remote fragmentation that allowed determination of the sequence of the amino acid components as AcNH-Ala-MeOxz-Val-DealaMeOxz-Ile-Leu-Thz-Ser-Gly-Gly-MeOxz-Leu-Deala-Oxz-Ala-Gly-Thz-Val-OH.The chiral amino acids were determined by the advanced Marfey's method to have L-conflgurations.Goadsporin was discovered from the culture broth of Streptomyces sp. TP-A0584 as a chemical substance that promotes sporulation and secondary metabolism in actinomycetes. Fermentation of the producing strain and isolation and biological properties of goadsporin were described in the preceding paper1}. Weherein report on the physico-chemical properties and structure determination of goadsporin.
Bioactive Microbial Metabolites. Part 36. Alchivemycin A, a Bioactive Polycyclic Polyketide with an Unprecedented Skeleton from Streptomyces sp. -The title compound exhibits potential antimicrobial effects against Micrococcus luteus and shows inhibitory effects on tumor cell invasion. -(IGARASHI*, Y.; KIM, Y.; IN, Y.; ISHIDA, T.; KAN, Y.; FUJITA, T.; IWASHITA, T.; TABATA, H.; ONAKA, H.; FURUMAI, T.; Org. Lett. 12 (2010) 15, 3402-3405,
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