Biosynthesis of the macrolide antibiotic patulolides by penicillium urticae S11R59: Identification of the origin of carbon atoms by 13C NMR spectroscopy.

Abstract

Patulolides are 12-membered macrolides produced by Penicillium urticae S11R59, and they are the simplest macrolide antibiotics. All carbon signals, including six methylene signals of patulolides A (1), B (2), and C (3), were completely assigned by use of the 13C two-dimensional INADEQUATE. The biosynthesis of patulolides was investigated with 13C labeled acetate. Feeding of [l-13C]acetate to a culture of P. urticae SI 1R59 gave patulolides A (1), B (2), and C (3), each of which showed enrichment at carbons 1, 3, 5, 7, 9, and 11; enrichment at carbons 2, 4, 6, 8, 10, and 12 was observed upon feeding of [2-13C]acetate. These results showed that patulolides A (1), B (2), and C (3) are pure acetogenic hexaketides derived from six acetate units coupled in head-to-tail fashion. © 1988, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.