Antitumor Agents. 282. 2'-(R)-O-acetylglaucarubinone, a quassinoid from Odyendyea gabonensis as a potential anti-breast and anti-ovarian cancer agent.
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.
Usami
Yoshihide
Y
Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7568, USA.
Nakagawa-Goto
Kyoko
K
Lang
Jing-Yu
JY
Kim
Yoon
Y
Lai
Chin-Yu
CY
Goto
Masuo
M
Sakurai
Nobuko
N
Taniguchi
Masahiko
M
Akiyama
Toshiyuki
T
Morris-Natschke
Susan L
SL
Bastow
Kenneth F
KF
Cragg
Gordon
G
Newman
David J
DJ
Fujitake
Mihoyo
M
Takeya
Koichi
K
Hung
Mien-Chie
MC
Lee
Eva Y-H P
EY
Lee
Kuo-Hsiung
KH
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
C552903:2'-(R)-O-acetylglaucarubinone; D000970:Antineoplastic Agents; D036702:Quassins