Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059.
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.
Deseo
Myrna A
MA
Centre for Phytochemistry and Pharmacology, Southern Cross University, Lismore, NSW 2480, Australia. mdeseo@scu.edu.au
Hunter
lain S
lS
Waterman
Peter G
PG
D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002850:Chromatography, Gel; D003470:Culture Media; D005285:Fermentation; D005960:Glucosides / Q000096:biosynthesis*; D009682:Magnetic Resonance Spectroscopy; D009284:Naphthols / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000235:genetics* / Q000378:metabolism*
C508792:4,8-dihydroxy-3-O-(glucopyranosyl)hydroxymethyl-4-methyl-1,2,3,4-tetrahydronaphthalene-1-one; C508790:4,8-dihydroxy-3-hydroxymethyl-4-methyl-1,2,3,4-tetrahydronaphthalene-1-one; C508791:4,8-dihydroxy-3-hydroxymethyl-4-methyl-1,4-dihydronaphthalene-1-one; D000900:Anti-Bacterial Agents; D003470:Culture Media; D005960:Glucosides; D009284:Naphthols