Title
Novel rearranged acetophenone derivatives possessing diverse architectures from the leaves of Melicope ptelefolia
Author
Jin-Fang Xu, Chao Han, Gui-Min Xue, Xiao-Bing Wang, Jun Luo, Ming-Hua Yang, Jian-Guang Luo, Ling-Yi Kong
Year
2019
Journal
Tetrahedron
Abstract
Melicolones C–K (1–9), nine acetophenone derivatives with three unprecedented architectures, were characterized from the leaves of Melicope ptelefolia. Among them, melicolone C (1) was a novel acetophenone analogue possessing a highly rearranged spiro skeleton. Melicolones D-F (2–4) were three novel acetophenone congeners bearing unusual octalactone ring. Melicolones G-K (5–9) were five new prenylated acetophenone derivatives featuring a 9-oxatricyclo [3.2.1.13, 8]nonane core. Their structures were established by extensive spectroscopic analysis and ECD spectra. These different structures were presumably derived from the same precursor via three major biosynthetic pathways. Compounds 5–9 exerted moderate effects to reverse multidrug-resistance in MCF-7/ADR cells with reversal fold values ranging from 6.2 to 13.3.
Instrument
J-810
Keywords
Circular dichroism, Absolute configuration, Natural products, Pharmaceutical