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

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• 作者：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 Cragg
• 刊名：Journal of Natural Products
• 出版年：2010
• 出版时间：September 24, 2010
• 年：2010
• 卷：73
• 期：9
• 页码：1553-1558
• 全文大小：278K
• 年卷期：v.73,no.9(September 24, 2010)
• ISSN：1520-6025

文摘

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 ¹H and ¹³C 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.