title: Antitumor Agents. 282. 2'-(R)-O-acetylglaucarubinone, a quassinoid from Odyendyea gabonensis as a potential anti-breast and anti-ovarian cancer agent.
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 (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.
authors.affiliation: Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7568, USA.
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Usami
authors.forename: Kyoko
authors.initials: K
authors.lastname: Nakagawa-Goto
authors.forename: Jing-Yu
authors.initials: JY
authors.lastname: Lang
authors.forename: Yoon
authors.initials: Y
authors.lastname: Kim
authors.forename: Chin-Yu
authors.initials: CY
authors.lastname: Lai
authors.forename: Masuo
authors.initials: M
authors.lastname: Goto
authors.forename: Nobuko
authors.initials: N
authors.lastname: Sakurai
authors.forename: Masahiko
authors.initials: M
authors.lastname: Taniguchi
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Akiyama
authors.forename: Susan L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.forename: Kenneth F
authors.initials: KF
authors.lastname: Bastow
authors.forename: Gordon
authors.initials: G
authors.lastname: Cragg
authors.forename: David J
authors.initials: DJ
authors.lastname: Newman
authors.forename: Mihoyo
authors.initials: M
authors.lastname: Fujitake
authors.forename: Koichi
authors.initials: K
authors.lastname: Takeya
authors.forename: Mien-Chie
authors.initials: MC
authors.lastname: Hung
authors.forename: Eva Y-H P
authors.initials: EY
authors.lastname: Lee
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004195:Disease Models, Animal; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D007624:KB Cells; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D036702:Quassins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: C552903:2'-(R)-O-acetylglaucarubinone; D000970:Antineoplastic Agents; D036702:Quassins