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

被引：18

作者：

Usami, Yoshihide ^{[1
]}

Nakagawa-Goto, Kyoko ^{[1
]}

Lang, Jing-Yu ^{[2
]}

Kim, Yoon ^{[3
]}

Lai, Chin-Yu ^{[1
]}

Goto, Masuo ^{[4
]}

Sakurai, Nobuko ^{[1
]}

Taniguchi, Masahiko ^{[1
]}

Akiyama, Toshiyuki ^{[1
]}

Morris-Natschke, Susan L. ^{[1
]}

Bastow, Kenneth F. ^{[5
]}

Cragg, Gordon ^{[6
]}

Newman, David J. ^{[6
]}

Fujitake, Mihoyo ^{[7
]}

Takeya, Koichi ^{[8
]}

Hung, Mien-Chie ^{[2
]}

Lee, Eva Y. -H. P. ^{[3
]}

Lee, Kuo-Hsiung ^{[1
,9
]}

机构：

[1] Univ N Carolina, Nat Prod Res Labs, Eshelman Sch Pharm, Chapel Hill, NC 27599 USA

[2] Univ Texas MD Anderson Canc Ctr, Houston, TX 77030 USA

[3] Univ Calif Irvine, Coll Med, Irvine, CA 92697 USA

[4] Univ N Carolina, Sch Med, Chapel Hill, NC 27599 USA

[5] Univ N Carolina, Div Med Chem & Nat Prod, Eshelman Sch Pharm, Chapel Hill, NC 27599 USA

[6] NCI, Frederick Canc Res & Dev Ctr, Frederick, MD 21702 USA

[7] Osaka Univ Pharmaceut Sci, Takatsu Ki, Osaka 5691094, Japan

[8] Tokyo Univ Pharm & Life Sci, Tokyo 1920355, Japan

[9] China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung, Taiwan

来源：

JOURNAL OF NATURAL PRODUCTS | 2010年 / 73卷 / 09期

关键词：

PROTEIN-SYNTHESIS; CELLS; BRUCEANTIN; BRUSATOL; (-)-GLAUCARUBOLONE; (-)-CHAPARRINONE; DIFFERENTIATION; SIMAROUBACEAE; INHIBITION; ALKALOIDS;

D O I：

10.1021/np100406d

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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.

引用

页码：1553 / 1558

页数：6

共 2 条

[1] Antitumor agents.: 239.: isolation, structure elucidation, total synthesis, and anti-breast cancer activity of neo-tanshinlactone from Salvia miltiorrhiza
Wang, XH
Bastow, KF
Sun, CM
Lin, YL
Yu, HJ
Don, MJ
Wu, TS
Nakamura, S
Lee, KH
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (23) : 5816 - 5819
[2] Antitumor Agents. 289. Design, Synthesis, and Anti-Breast Cancer Activity in Vivo of 4-Amino-2H-benzo[h]chromen-2-one and 4-Amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one Analogues with Improved Water Solubility
Dong, Yizhou
Nakagawa-Goto, Kyoko
Lai, Chin-Yu
Morris-Natschke, Susan L.
Bastow, Kenneth F.
Kim, Yoon
Lee, Eva Y-H. P.
Lee, Kuo-Hsiung
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (03): : 370 - 377

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