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Fitoterapia ; 117: 34-40, 2017 Mar.
Article in English | MEDLINE | ID: mdl-28065696

ABSTRACT

A comprehensive reinvestigation of chemical constituents from CHCl3-soluble extract of Cipadessa baccifera led to the isolation of two new limonoids 1, 2 together with six known compounds 3-8. Their structures were established on the basis of extensive analysis of spectroscopic (IR, MS, 2D NMR) data. Further, a series of cipaferen G (3) derivatives were efficiently synthesized utilizing Yamaguchi esterification (2, 4, 6-trichlorobenzoyl chloride, Et3N, THF, DMAP, toluene) at the C-3 position of the limonoids core, which is being reported for the first time. The anti-proliferative activity of the isolates and the synthetic analogues were studied against HeLa, PANC 1, HepG2, SKNSH, MDA-MB-231 and IMR32 cancer cells using the sulphorodamine B assay. Among the tested compounds, 13d and 13h manifested potent activity against IMR32, HepG2 cell lines with GI50 0.013 and 0.01µM, respectively.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Limonins/chemistry , Meliaceae/chemistry , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Humans , Insecticides/chemistry , Insecticides/isolation & purification , Limonins/isolation & purification , Molecular Structure , Plant Extracts/chemistry , Seeds/chemistry , Spodoptera
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