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.
One-pot successive Arbuzov/HWE synthesis and preliminary antitumor activity evaluation of 2,4-di((E)-styryl)quinoline-3-carboxylates was described in this study.
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