A Labeling Study To Elucidate the Biosynthesis of 4-(4-Hydroxyphenyl)-Butan-2-one (Raspberry Ketone) by Nidula niveo-tomentosa

Abstract

ABSTRACT Submerged cells of the basidiomycete Nidula niveo-tomentosa , a microbial producer of 4-(4-hydroxyphenyl)-butan-2-one, were supplemented with 13 C-labeled l -phenylalanines and with [1- 13 C]glucose. Labeled transformation products were detected by a novel method of analyzing stable isotope-labeled metabolites, gas chromatography (GC) coupled to an atomic emission detector, and by GC-mass spectrometry. A benzoate moiety was side chain elongated according to the poly-β-keto scheme. The presence of an acetyl coenzyme A-carboxylase inhibitor shifted the spectrum of products to benzyl compounds. Hence, the fungal pathway differs from the one established for plant tissues.