Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059

The Journal of Antibiotics
Myrna A DeseoP G Waterman

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)-4beta,8-dihydroxy-3alpha-hydroxymethyl-4alpha-methyl-1,2,3,4-tetrahydronaphthalene1-one (1), 4xi8-dihydroxy-3-hydroxymethyl-4xi-methyl-1,4-dihydronaphthalene-1-one (2) and (rel)-4beta,8-dihydroxy-3alpha-O-[alpha-glucopyranosyl]hydroxymethyl-4alpha-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.

References

Oct 1, 1971·Journal of General Microbiology·E J Friend, D A Hopwood
Jul 10, 1999·Natural Product Reports·A TrefzerA Bechthold
Oct 17, 2001·Trends in Biotechnology·C Méndez, J A Salas

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Citations

Jul 16, 2016·The Journal of Organic Chemistry·Zhuo ShangRobert J Capon
Mar 5, 2015·Chemical Society Reviews·Sherif I ElshahawiJon S Thorson
Oct 1, 2015·Organic & Biomolecular Chemistry·E M RigsbeeM K Brown
Jul 17, 2007·The Journal of Biological Chemistry·Wenjun ZhangYi Tang
May 28, 2009·Chembiochem : a European Journal of Chemical Biology·Peng WangYi Tang

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