Isolation, Chiral-Phase Resolution, and Determination of the Absolute Configurations of a Complete Series of Stereoisomers of a Rearranged Acetophenone with Three Stereocenters.

Published on Apr 18, 2019in Journal of Natural Products3.779
· DOI :10.1021/ACS.JNATPROD.8B00003
Jin-Fang Xu6
Estimated H-index: 6
(CPU: China Pharmaceutical University),
Chao Han11
Estimated H-index: 11
(CPU: China Pharmaceutical University)
+ 5 AuthorsLing-Yi Kong58
Estimated H-index: 58
(CPU: China Pharmaceutical University)
A synthesis-inspired chemical investigation of the leaves of Melicope ptelefolia led to the isolation of evodialones A–D (1–4), four rearranged acetophenone stereoisomers possessing a prenylated acylcyclopentenone skeleton with three stereogenic carbons. Evodialones C and D (3 and 4) are new minor constituents. The chiral-phase HPLC resolution gave (+)-1–4 and (−)-1–4, eight enantiomers forming a complete stereoisomer library. Their absolute configurations were elucidated via extensive spectroscopic data and a modified Mosher’s method. The relationship between the chiral structures and their NMR and ECD data is discussed. Compounds (±)-1, -2, and -4 have significant protective effects on high-glucose-induced oxidative stress in human vein endothelial cells.
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