Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059
Issue Date
12-2005
Abstract
Three novel polyketide metabolites were isolated from laboratory-scale fermentation of the Streptomyces rimosus mutant strain R1059. Structural elucidation of the compounds was based on NMR experiments. The compounds were characterized as naphthalene derivatives: (rel)-4β,8-dihydroxy-3α- hydroxymethyl-4α-methyl-1,2,3,4-tetrahydronaphthalene-1-one (1), 4ξ,8-dihydroxy-3-hydroxymethyl-4ξ-methyl-1,4-dihydronaphthalene-1-one (2) and (rel)-4β,8-dihydroxy-3α-O-[α-glucopyranosyl]hydroxymethyl- 4α-methyl-1,2,3,4-tetrahydronaphthalene-1-one (3). The compounds isolated appear to be derived via a shorter polyketide backbone than oxytetracycline (4), the normal end-product made by the parent of this strain. Compound 3 was the glucoside of 1 and must be formed as a post-PKS reaction by the activation of a glycosyl transferase, which has not been reported in this species before. © Japan Antibiotics Research Association.
Source or Periodical Title
Journal of Antibiotics
ISSN
218820
Volume
58
Issue
12
Page
822-827
Document Type
Article
Language
English
Subject
Glycosyl transferase, Mutant, Novel metabolite, Polyketide, Streptomyces rimosus
Recommended Citation
Deseo MA, Hunter lS, Waterman PG. Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059. J Antibiot (2005). 58(12):822-7
Identifier
DOI: 10.1038/ja.2005.110
Digital Copy
YES