Three 4-monosubstituted butyrolactones from a regulatory gene mutant of Streptomyces rochei 7434AN4

Abstract

Extensive metabolite analysis of Streptomyces rochei 7434AN4 was performed to discover uncharacterized secondary metabolites. A mutant strain of S. rochei, in which two regulatory genes srrC (a tetR-type repressor) and srrY (SARP-type activator) were inactivated, accumulated three 4-monosubstituted γ-butyrolactones YT02-A, YT02-B, and KH01-A, which were not detected in the parent strain. Their structures were identified as 4,10-dihydroxy-10-methyldodecan-4-olide, 4,10-dihydroxy-10-methylundecan-4-olide, and 4-hydroxy-11-oxo-10-methyldodecan-4-olide. A structural comparison indicated that the three butanolides and the signaling molecules, termed S.rochei butenolides (SRBs), could share common C12 or C13 fatty acids for their biosynthesis intermediates, however, these three butanolides did not induce antibiotic production even at 50μM concentration (1000-folds of the minimum antibiotic-inducing concentration of SRBs) in S.rochei.