13C and 2H n.m.r. studies on the biosynthesis of O-methylasparvenone, a hexaketide metabolite of Aspergillus parvulus

Abstract

Incorporations of singly and doubly labelled ¹³C acetates and [²H₃] acetate into O-methylasparvenone, a dihydronaphthalene metabolite of Aspergillus parvulus, and analysis of the resultant enriched samples by high-field ¹³C and ²H n.m.r. spectroscopy indicate a hexaketide biosynthesis and a novel acetate assembly pattern; the ²H-labelling pattern and levels of enrichment provide information on the sequence and mechanisms of the reduction, oxidation, and deoxygenation steps on the biosynthetic pathway.