New Cytotoxic Alkyl Phloroglucinols fromProtorhus thouvenotii

Abstract

Two new cytotoxic alkylene phloroglucinols and one known compound were isolated through chromatographic separation from the methanolic extract of the dried fruits of Protorhus thouvenotii (Anacardiaceae). The compounds showed marginal in vitro cytotoxicity in the A2780 ovarian cancer cell line assay with an IC50 of 11 microg/mL.

Chlorabietols A–C, Phloroglucinol-Diterpene Adducts from the Chloranthaceae Plant Chloranthus oldhamii

“…Similar to 1, both the two double bonds in the side chain have the Z geometry according to the 13 C NMR chemical shifts of the bisallylic methylene carbon C-12" (δ C 25.6) and the two allylic carbons C-9" (δ C 27.2) and C-15" (δ C 27.2). 7,9 Actually, the NMR spectroscopic data of unit B in 3 were found to be in full agreement with those of thouvenol B 7 (7, Figure 1). As expected, subsequent analyses of the coupling constants, ROE correlations, and experimental ECD data ( Figure S4) revealed that 3 has the same absolute configuration as that of 2.…”

“…9 This was supported by the upfield 13 C NMR resonances for the two bisallylic methylene carbons [δ C 25.6 (C-11") and 25.5 (C-14")] and the two allylic carbons [δ C 27.3 (C-8") and 20.5 (C-17")], which were in full agreement with those of reported resorcinols with two or more Z-configured double bonds in their alkenyl units. 7,9 These NMR data were superimposable on those of moniliferanone C (5) just isolated from the brown algae Cystophora subfarcinata. 6 The planar structure of unit B was then verified to be the same as 5 by further COSY and HMBC experiments ( Figure 2).…”

“…7 Thus, this is the first report regarding their occurrence in the Chloranthus genus. In this study, we present the isolation and structure elucidation of 1-3, as well as the inhibitory effects of compounds 1-7 on protein tyrosine phosphatase 1B (PTP1B).…”

“…of an acylphloroglucinol moiety. [6][7][8][9] A linear C 17 alkene with three double bonds was thereafter elucidated based on the remainder carbon signals: one methyl at δ C 14.3, ten sp 3 methylenes at δ C 20.5-42.9 and six well-resolved olefinic carbons at δ C 127. 1, 127.8, 128.2, 128.3, 130.3 and 132.0 ( Table 1).…”

Geranyl Derivative of Phloroacetophenone Induces Cancer Cell-Specific Apoptosis through Bax-Mediated Mitochondrial Pathway in MCF-7 Human Breast Cancer Cells

“…Phloroacetophenone derivatives such as thouvenol A and thouvenol B are reported to have cytotoxic activity against A2780 ovarian cancer cells. 30) In a recent report by Basabe et al, 2) the cytotoxic activities of various derivatives of phloroacetophenone in several cancer cell lines, HT-29, A549, HeLa, and HL-60 have been compared. Geranyl-phloroacetophenone was the most effective in inhibiting cell viability than farnesyl, oleyl, or stearyl derivatives.…”