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DOI: 10.1055/s-0029-1186002
© Georg Thieme Verlag KG Stuttgart · New York
Ent-Kaurane Diterpenoids from Rabdosia rubescens and Their Cytotoxic Effects on Human Cancer Cell Lines
Publication History
received March 5, 2009
revised May 18, 2009
accepted June 29, 2009
Publication Date:
03 August 2009 (online)
![](https://www.thieme-connect.de/media/plantamedica/201002/lookinside/thumbnails/10.1055-s-0029-1186002-1.jpg)
Abstract
Two new ent-kaurane diterpenoids, 16,17-exo-epoxide-oridonin (1) and 11,15-O,O-diacetyl-rabdoternins D (2), together with thirteen known ones, were isolated from the aerial parts of Rabdosia rubescens. Their structures were established on the basis of high-field 1D and 2D NMR methods supported by HRMS. All diterpenoids were tested for cytotoxicity against human Hep G2, COLO 205, MCF-7, and HL-60 cancer cells. The compounds oridonin (3), 14-O-acetyl-oridonin (4), 1,14-O,O-diacetyl-oridonin (5), rosthorin (6), effusanin E (7), and ponicidin (8), as well as six α-methylene γ-ketone bearing diterpenoids, were modestly active in these assays.
Key words
Rabdosia rubescens - Labiatae - ent‐kaurane - cytotoxicity - antitumor
References
- 1 The Health Department and National Chinese Medicine Management Office .Zhong Hua Ben Cao, Vol. 7. Shanghai; Shanghai Science and Technology Press 1999: 150-154
- 2 Takeda Y, Otsuka H. Recent advances in the chemistry of diterpenoids from Rabdosia species. Stud Nat Prod Chem. 1995; 15 111-185
- 3 Liu C, Zhao Z. Advances in research of Rabdosia rubescens (Hemsl.) Hara. Zhongguo Yaoxue Zazhi (Beijing). 1998; 33 577-581
- 4 Sun H D, Lin Z W, Qin C Q, Chao J H, Zhao Q Z. Studies on the chemical constituents of antitumor plant Rabdosia rubescens (Hemsl.) Hara. Yun-nan Chih Wu Yen Chiu. 1981; 3 95-100
- 5 Sun H D, Chao J H, Lin Z W, Marunaka T, Minami Y, Fujita T. The structure of rubescensin C: a new minor diterpenoid isolated from Rabdosia rubescens. Chem Pharm Bull. 1982; 30 341-343
- 6 Taiho Pharmaceutical Co., Ltd., Japan .Rubescensin C. JP 57179185 A2 19821104 1982
- 7 Liu Z, Yue Z. Study on chemical constituent of Rabdosia racemosa. Zhongcaoyao. 1997; 28 334-337
- 8 Taiho Pharmaceutical Co., Ltd., Japan .Rubescensin D. JP 58152838 A2 19830910 1983
- 9 Li J, Liu C, Sun H, Lin Z. Structures of lushanrubescensin B and C: new diterpenoids from Rabdosia rubescens f. lushanensis. Yunnan Zhiwu Yanjiu. 1986; 8 93-97
- 10 Li J, Sun H, Lin Z. The structure of lushanrubescensin E. Yunnan Zhiwu Yanjiu. 1987; 9 485-488
- 11 Mosmann J. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65 55-63
- 12 Fujita E, Fujita T, Katayama H, Shibuya M, Shingu T. Terpenoids. XV. Structure and absolute configuration oridonin isolated from Isodon japonicus and Isodon trichocarpus. JCS. 1970; 12 1674-1681
- 13 Mori S, Shudo K, Ageta T, Koizumi T, Okamoto T. Constituents of Isodon trichocarpus. I. Isolation of the constituents and the structures of isodonol, enmedol, and enmenol. Chem Pharm Bull. 1970; 18 871-883
- 14 Li G, Wang Y. Studies on the diterpenoids of Rabdosia rosthornii (Diels) Hara. Yaoxue Xuebao. 1984; 19 590-592
- 15 Hou A J, Zhao Q S, Li M L, Jiang B, Lin Z W, Sun H D, Zhou Y P, Lu Y, Zheng Q T. Cytotoxic 7,20-epoxy ent-kauranoids from Isodon xerophilus. Phytochemistry. 2001; 58 179-183
- 16 Xu M, Tang M, Cheng P. Studies on the antitumor constituents of Rabdosia nervosa. Zhongcaoyao. 1985; 16 51-52
- 17 Fujita T, Takeda Y, Shingu T, Ueno A. Structures of effusanins, antibacterial diterpenoids from Rabdosia effusa. . Chem Lett. 1980; 12 1635-1638
- 18 Wang X R, Wang H P, Hu H P, Sun H D, Wang S Q, Ueda S, Kuroda Y, Fujita T. Structures of macrocalyxin B, F, G and H, and maoyerabdosin from Isodon macrocalyx. Phytochemistry. 1995; 38 921-926
- 19 Liu H M, Yan X B, Kiuchi F, Liu Z Z. A new diterpene glycoside from Rabdosia rubescens. Chem Pharm Bull. 2000; 48 148-149
- 20 Takeda Y, Takeda K, Fujita T, Sun H D, Minami Y. Rabdoternins D–G, ent-7β,20-epoxykaurenes from Rabdosia ternifolia. Phytochemistry. 1994; 35 1513-1516
- 21 Takeda Y, Takeda K, Fujita T, Sun H D, Minami Y. Studies on the diterpenoid constituents of Rabdosia ternifolia: structural elucidation of new diterpenoids, rabdoternins A, B and C. Chem Pharm Bull. 1990; 38 439-442
- 22 Han Q B, Li R T, Li M L, Mou Y K, Tian Q E, Li S W, Sun H D. Ent-kauranoids from Isodon rubescens var. taihangensis. J Asian Nat Prod Res. 2005; 7 31-36
- 23 Ho C T, Bai N S, Dong Z G, Bode A M, Dushenkov S. Bioactive compounds and methods of uses thereof. US Patent 7353739 2008
- 24 Nagashima F, Kondoh M, Uematsu T, Nishiyama A, Saito S, Sato M, Asakawa Y. Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata NEES. Chem Pharm Bull. 2002; 50 808-813
Chi-Tang Ho
Department of Food Science
Rutgers University
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Email: ho@aesop.rutgers.edu