Isolation and structures of nitrogen-free platenolide glycosides. II. The 5-O-(alpha-mycarosyl)- and 5-O-(3'-demethyl-beta-mycaroxyl)-platenolides I and II.

Three novel glycosides of platenolides I and II containing either mycarose (2,6-dideoxy-3-C-methyl-L-ribohexopyranose) or 3-demethyl-mycarose (2,6-dideoxy-L-ribohexopyranose) were isolated as the shunt products of turimycin biosynthesis by an industrial strain of Streptomyces hygroscopicus IMET JA 6599. By means of MS, 13C and 1H NMR spectroscopic studies, their structures were assigned as 5-O-(alpha-mycarosyl)-platenolide I (MYC-Pl-I), 5-O-(alpha-mycarosyl)-platenolide II (MYC-Pl-II) and 5-O-(3'-demethyl-beta-mycarosyl)-platenolide II (DM-MYC-Pl-II). The occurrence of 3-demethyl-mycaroside amongst the shunt metabolites is discussed in terms of its biosynthesis.