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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
Author(s) -
Zhang ShuMin,
Zhang Lu,
Kou LiJuan,
Yang QiaoLi,
Qu Bo,
Pescitelli Gennaro,
Xie ZePing
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23178
Subject(s) - chemistry , racemization , polyketide , enantiomer , circular dichroism , benzofuran , stereochemistry , absolute configuration , chiral column chromatography , organic chemistry , biosynthesis , enzyme
(±)‐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.