Secondary metabolites by chemical screening, 41 - Structure and biosynthesis of mutolide, a novel macrolide from a UV mutant of the fungus F-24 ' 707

The 14-membered macrolide, mutolide (1), was discovered by chemical screeni ng of the culture broth of the fungus F-24'707y, obtained after UV mutagene sis of the wild type strain, which normally produces the spirobisnaphthalen e cladospirone bisepoxide (2). The structure of 1 was established by detail ed spectroscopic analysis, X-ray analysis and derivatisation. The biogeneti c origin of the carbon skeleton and the hydroxy groups was verified by feed ing sodium [1-C-13]acetate and O-18(2) to growing cultures of the fungus. M acrolide 1 is generated from acetate/malonate only. The unexpected change o f the normal metabolite pattern of this strain is discussed, and proves the value of the OSMAC method.