Biosynthesis of Patulin; in Vitro Conversion of Gentisyl Alcohol into Patulin by Microsomal Enzyme(S) and Retention of One of the Carbinol Protons in this Reaction

Abstract

The late stage of patulin biosynthesis was studied using cell-free preparations of Penicillium patulum NRRL 2159A. The substrate for the ring cleavage reaction was established to be gentisyl alcohol, which was converted into patulin by a microsomal enzyme(s). Incubation of [1’-14C, 3H2]-gentisy1 alcohol with the microsomal preparation revealed that one of the carbinol protons of this substrate is retained in patulin. This answers the long-standing question why the side chain protons of aromatic intermediates are not incorporated into patulin in feeding experiments. © 1986, The Pharmaceutical Society of Japan. All rights reserved.