(±)-Pratenone A (1), the first representative of natural 3-(1-naphthyl)-2-benzofuran-1(3H)-one polyketides, was isolated from a marine-derived Streptomyces pratensis strain KCB-132 together with three other new analogues (2−4). Its structure was assigned by spectroscopic analysis, and the absolute configurations of the two enantiomers separated by high-performance liquid chromatography were determined by single-crystal X-ray diffraction and electronic circular dichroism calculations. The solvent-induced racemization of 1 and a proposed biogenetic pathway to 1−4 from the co-isolated angucyclinone precursor, as well as their biological activity, are also discussed.
Isolation, stereochemical study, and racemization of (±)-pratenone A, the first naturally occurring 3-(1-naphthyl)-2-benzofuran-1(3H)-one polyketide from a marine-derived actinobacterium
Pescitelli G.
Penultimo
;
2020-01-01
Abstract
(±)-Pratenone A (1), the first representative of natural 3-(1-naphthyl)-2-benzofuran-1(3H)-one polyketides, was isolated from a marine-derived Streptomyces pratensis strain KCB-132 together with three other new analogues (2−4). Its structure was assigned by spectroscopic analysis, and the absolute configurations of the two enantiomers separated by high-performance liquid chromatography were determined by single-crystal X-ray diffraction and electronic circular dichroism calculations. The solvent-induced racemization of 1 and a proposed biogenetic pathway to 1−4 from the co-isolated angucyclinone precursor, as well as their biological activity, are also discussed.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
