Isolation and structures of nitrogen-free platenolide glycosides. I. The 5-O-(deoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolides I and II.
Four novel nitrogen-free glycosides of platenolides I and II were isolated as secondary shunt metabolites of the turimycin biosynthesis from the culture broth of an industrial strain of Streptomyces hygroscopicus IMET JA 6599. By spectral (MS, 1H and 13C NMR) studies the structures of the glycosides have been settled as 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide I (DDAH-Pl-I), 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide II (DDAH-Pl-II), 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-14-hydroxyl-platenolide II (DDAH-OH-Pl-II) and 5-O-(6'-deoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide II (DAH-Pl-II). A fifth glycoside, 5-O-(6'-deoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide I (DAH-Pl-I) was identified through its MS data.
D000900:Anti-Bacterial Agents / Q000302:isolation & purification*; D006027:Glycosides / Q000302:isolation & purification*; D007933:Leucomycins / Q000096:biosynthesis; D018942:Macrolides; D008968:Molecular Conformation; D013302:Streptomyces / Q000378:metabolism
D000900:Anti-Bacterial Agents; D006027:Glycosides; D007933:Leucomycins; D018942:Macrolides; C016675:platenolide I; C026531:platenolide II