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Antitumor Agents. 282. 2′-( R )- O -Acetylglaucarubinone, a Quassinoid from Odyendyea gabonensis As a Potential Anti-Breast and Anti-Ovarian Cancer Agent

2010; American Chemical Society; Volume: 73; Issue: 9 Linguagem: Inglês

10.1021/np100406d

1520-6025

Yoshihide Usami, Kyoko Nakagawa‐Goto, Jing-Yu Lang, Yoon Kim, Chin-Yu Lai, Masuo Goto, Nobuko Sakurai, Masahiko Taniguchi, Toshiyuki Akiyama, Susan L. Morris‐Natschke, Kenneth F. Bastow, Gordon M. Cragg, David Newman, Mihoyo Fujitake, Koichi Takeya, Mien‐Chie Hung, Eva Y.-H.P. Lee, Kuo‐Hsiung Lee,

Multicomponent Synthesis of Heterocycles

A new quassinoid, designated 2'-(R)-O-acetylglaucarubinone (1), and seven known quassinoids (2-8) were isolated, using bioactivity-guided separation, from the bark of Odyendyea gabonensis (Pierre) Engler [syn. Quassia gabonensis Pierre]. The structure of 1 was determined by spectroscopic analysis and by semisynthesis from glaucarubolone. Complete (1)H and (13)C NMR assignments of compounds 1-8 were also established from detailed analysis of two-dimensional NMR spectra, and the reported configurations in odyendene (7) and odyendane (8) were corrected. Compound 1 showed potent cytotoxicity against multiple cancer cell lines. Further investigation using various types of breast and ovarian cancer cell lines suggested that 1 does not target the estrogen receptor or progesterone receptor. When tested against mammary epithelial proliferation in vivo using a Brca1/p53-deficient mice model, 1 also caused significant reduction in mammary duct branching.