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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

  1. Author:
    Usami, Y.
    Nakagawa-Goto, K.
    Lang, J. Y.
    Kim, Y.
    Lai, C. Y.
    Goto, M.
    Sakurai, N.
    Taniguchi, M.
    Akiyama, T.
    Morris-Natschke, S. L.
    Bastow, K. F.
    Cragg, G.
    Newman, D. J.
    Fujitake, M.
    Takeya, K.
    Hung, M. C.
    Lee, E.
    Lee, K. H.

  2. Author Address

    [Usami, Yoshihide; Nakagawa-Goto, Kyoko; Lai, Chin-Yu; Sakurai, Nobuko; Taniguchi, Masahiko; Akiyama, Toshiyuki; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung] Univ N Carolina, Nat Prod Res Labs, Eshelman Sch Pharm, Chapel Hill, NC 27599 USA. [Lang, Jing-Yu; Hung, Mien-Chic] Univ Texas MD Anderson Canc Ctr, Houston, TX 77030 USA. [Kim, Yoon; Lee, Eva Y. -H. P.] Univ Calif Irvine, Coll Med, Irvine, CA 92697 USA. [Goto, Masuo] Univ N Carolina, Sch Med, Chapel Hill, NC 27599 USA. [Bastow, Kenneth F.] Univ N Carolina, Div Med Chem & Nat Prod, Eshelman Sch Pharm, Chapel Hill, NC 27599 USA. [Cragg, Gordon; Newman, David J.] NCI, Frederick Canc Res & Dev Ctr, Frederick, MD 21702 USA. [Fujitake, Mihoyo] Osaka Univ Pharmaceut Sci, Takatsu Ki, Osaka 5691094, Japan. [Takeya, Koichi] Tokyo Univ Pharm & Life Sci, Tokyo 1920355, Japan. [Lee, Kuo-Hsiung] China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung, Taiwan.;Lee, KH, Univ N Carolina, Nat Prod Res Labs, Eshelman Sch Pharm, Chapel Hill, NC 27599 USA.;khlee@unc.edu
    1. Year: 2010
    2. Date: Sep
  2. Journal: Journal of Natural Products
    1. 73
    2. 9
    3. Pages: 1553-1558
  4. Type of Article: Article
  5. ISSN: 0163-3864
  1. Abstract:

    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 H-1 and C-13 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 Brcal/p53-deficient mice model, 1 also caused significant reduction in mammary duct branching.

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External Sources

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  2. DOI: 10.1021/np100406d
  3. View record in Web of Science®
  4. WOS: 000282038800016

Library Notes

  1. Fiscal Year: FY2009-2010
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