New seco-limonoids from Cipadessa baccifera: Isolation, structure determination, synthesis and their antiproliferative activities

Abstract

A comprehensive reinvestigation of chemical constituents from CHCl-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, EtN, 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 GI 0.013 and 0.01μM, respectively.

Chemistry and Biology of Novel Meliaceae Limonoids

“…At 50 ppm, compound (574) exhibited insecticidal activity against Caenorhabditis elegans with mortality score of 66 while compounds (575, 576, 587, 601, 602, 610, 611) were inactive 284 . Compound (681) at 100 μg/cm 2 and 25 μg/cm 2 , exhibited antifeedant activity against Spodoptera litura with antifeedancy rate of 62.48 and 28.50 % respectively and compound (1386) at 100 and 25 μg/cm 2 exhibited antifeedant activity against Spodoptera litura with antifeedancy rate of 90.32 and 59.5 % respectively 307 . At 1 mM, compound (708) exhibited insect-resistance ability against Drosophila melanogaster with an antifeedant index of 32.8 % while the antifeedant index of blank control and positive control was 14.7 and 28.5 % respectively 313 .…”

“…Cochinchinoid A and B (304 and 305) show the same molecular formula as obtained by using HRESI (-) MS but differ at stereochemistry of two ester substituents at C3 and C7. The ester moieties at C3 and C7 in compound (305) are replaced by tigloyl group in Cochinchinoid C (306) and it is displaced only at C3 in Cochinchinoid D (307). In Cipadesin L (308) hydroxyl group at C1 is acetylated and ester moiety at C3 is replaced by tigloyl group with absence of hydroxyl group at C17, when compared to compound (304).…”

Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones

“…Surprisingly, cleavage of the C-7 and C-8 bond and the oxygen-bridge between the C-1 and C-14 carbons resulted in the activity against IMR32 human neuroblastoma cells being enhanced substantially, as shown by cipaferen G (11m), which was potently cytotoxic against IMR cells, with an IC 50 value of 22 nM (Figure 29). 299 Also, the cytotoxicity against HepG2 human hepatoma cells of cipaferen G (11m) was enhanced more than 10 000-fold, when a Nbenzoylpiperazine unit was linked synthetically to its acetyl group [e.g., 11n, IC 50 = 0.01 μM (HepG2 cells)]. Both 11m and 11n showed some selectivity among the cancer cells tested, 299 and thus, they seem to be promising lead compounds for further investigation.…”

UPLC-MSE Guided Isolation of New Antifeedant Limonoids from Fruits of Trichilia connaroides

“…During the past decade, our group has focused on phytochemical investigations of medicinal plants of the Meliaceae family, resulting in a series of structurally intriguing limonoids with potential biological activities including antifeedant activities. − Recently, we have reported the isolation and characterization of two new seco phragmalin-type limonoids from the CHCl 3 extract from fruits of T. connaroides . In continuation of our efforts to identify new limonoids from Trichilia species, we performed the LC-MS E analysis of chloroform extract from T. connaroides by UPLC-Q-TOF-MS/MS technique, which clearly demonstrated the existence of new limonoids in minor quantities (Figure ).…”