Elsevier

Tetrahedron

Volume 45, Issue 8, 1989, Pages 2307-2321
Tetrahedron

Application of stable isotope labelling methodology to the biosynthesis of the mycotoxin, terretonin, by aspergillus terreus: incorporation of 13C-labelled acetates and methionine, 2H- and 13C, 18O-labelled ethyl 3,5-dimethylorsellinate and oxygen-18 gas

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Abstract

Incorporation of 13C-labelled acetates and methionine, 14C and 2H-labelled ethyl 3,5-dimethylorsellinate into terretonin (5) by cultures of Aspergillus terreus indicated that its biosynthesis proceeds via a mixed polyketide-terpenoid (meroterpenoid) pathway. Incorporation of 18O2 gas and ethyl 3,5-dimethylorsellinate (7) doubly labelled with 13C and 18O in the carbonyl of the carboxyl group and at the C-6 position into terretonin (5) and observation of 18O isotope-induced shifts in the 13C n.m.r. spectra and GC/MS studies of the enriched metabolites determined the origin of all of the oxygen atoms in (5) and provided mechanistic insight into the biosynthetic pathway.

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