Subscribe to RSS
DOI: 10.1055/s-2006-947178
A New Triterpene and Anti-Hepatitis B Virus Active Compounds from Alisma orientalis
Publication History
Received: November 20, 2005
Accepted. May 23, 2006
Publication Date:
20 July 2006 (online)
Abstract
A new triterpenoid named alisol O (1) was isolated from the rhizomes of Alisma orientalis, together with six known compounds: alisol A 24-acetate (2), 25-anhydroalisol A (3), 13β,17β-epoxyalisol A (4), alisol B 23-acetate (5), alisol F (6), and alisol F 24-acetate (7). Based on 1D and 2D-NMR data (HMQC, HMBC, COSY, ROESY), the structure of the new compound was deduced to be 11-dehydroxy-12-dehydroalisol F-24-acetate (1). Compounds 2 - 7 exhibited inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC50 values of 2.3, 11.0, 15.4, 14.3, 0.6 and 7.7 μM, and on HBV e antigen (HBeAg) secretion with IC50 values of 498.1, 17.6, 41.0, 19.9, 8.5 and 5.1 μM, respectively.
References
- 1 Shanghai Medical C ollege. Zhong-Yao-Da-Ci-Dian (The Dictionary of Chinese Crude Drugs). Shanghai; Shanghai Science and Technology Press 1977: p 1461
- 2 Oshima Y, Iwakawa T, Hikino H. Alismol and alismoxide, sesquiterpenoids of Alisma rhizomes. Phytochemistry. 1983; 22 183-5
- 3 Geng P W, Fukuyama Y, Yamada T, Wang R, Bao J X, Nakagawa K. Triterpenes from the rhizome of Alisma plantago-aquatica . Phytochemistry. 1988; 27 1161-4
- 4 Yoshikawa M, Tomohiro N, Murakami T, Ikebata A, Matsuda H, Matsuda H. et al . Studies on alismatis rhizoma. III. Stereostructures of new protostane-type triterpenes, alisols H, I, J-23-acetate, K-23-acetate, L-23-acetate, and N-23-acetate, from the dried rhizome of Alisma orientale . Chem Pharm Bull. 1999; 47 524-8
- 5 Yoshikawa M, Murakami T, Ikebata A, Ishikado A, Murakami N, Yamahara J. et al . Absolute stereostructures of alismalactone 23-acetate and alismaketone-A 23-acetate, new seco-protostane and protostane-type triterpenes with vasorelaxant effects from Chinese Alismatis rhizoma. Chem Pharm Bull. 1997; 45 756-8
- 6 Matsuda H, Kageura T, Toguchida I, Murakami T, Kishi A, Yoshikawa M. Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate. Bioorg Med Chem Lett. 1999; 9 3081-6
- 7 Yoshikawa M, Hatakeyama S, Tanaka N, Fukuda Y, Yamahara J, Murakami N. Crude drugs from aquatic plants. I. On the constituents of Alismatis rhizoma (1). Absolute stereostructures of alisols E 23-acetate, F, and G, three new protostane-type triterpenes from Chinese Alismatis rhizoma. Chem Pharm Bull. 1993; 41 1948-54
- 8 Nakajima Y, Satoh Y, Katsumata M, Tsujiyama K, Ida Y, Shoji J. Terpenoids of Alisma orientale rhizome and the crude drug alismatis rhizoma. Phytochemistry. 1994; 36 119-27
- 9 Yoshikawa M, Fukuda Y, Hatakeyama S, Tanaka N, Matsuda H, Yamahara J. et al . Sulfoorientalols a, b, c, and d, four new biologically active sesquiterpenes from Alismatis rhizoma. Chem Pharm Bull. 1993; 41 1194-6
- 10 Yoshikawa M, Yamaguchi S, Matsuda H, Kohda Y, Ishikawa H, Tanaka N. et al . Crude drugs from aquatic plants. IV. On the constituents of Alismatis rhizoma (2). Stereostructures of bioactive sesquiterpenes, alisol, alismoxide, orientalols A, B, and C, from Chinese Alismatis rhizoma. Chem Pharm Bull. 1994; 42 1813-6
- 11 Yoshikawa M, Hatakeyama S, Tanaka N, Fukuda Y, Murakami N, Yamahara J. Orientals A, B, and C, sesquiterpene constituents from Chinese Alismatis rhizoma, and revised structures of alismol and alismoxide. Chem Pharm Bull. 1992; 40 2582-4
- 12 Peng G P, Lou F C, Huang X F, Tian G. Structure of orientanone from Alisma orientalis, A novel sesquiterpene originating from guaiane-type carbon skeleton by isopropyl shift. Tetrahedron. 2002; 58 9045-8
- 13 Peng G P, Zhu G Y, Lou F C. Two new triterpenoids from Alisma orientalis . Nat Prod Res Dev. 2002; 14 5-8
- 14 Peng G P, Lou F C. The diterpenoids from Alisma orientalis . Acta Pharmacol Sin. 2002; 37 950-4
- 15 Peng G P, Tian G, Huang X F, Lou F C. Guaiane-type sesquiterpenoids from Alisma orientalis . Phytochemistry. 2003; 63 877-81
- 16 Wu J, Xie H Y, Jiang G P, Xu X, Zheng S S. The effecte of mycophenolate acid on hepatitis B virus replication in vitro . Hepatobiliary Pancreat Dis Int. 2003; 2 410-3
- 17 Huang R L, Chen C C, Huang Y L, Hsieh D J, Hu C P, Chen C F. et al . Osthole increases glycosylation of hepatitis B surface antigen and suppresses the secretion of hepatitis B virus in vitro . Hepatology. 1996; 24 508-15
- 18 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65 55-63
- 19 Rukachaisirikul V, Pailee P, Hiranrat A, Tuchinda P, Yoosook C, Kasisit J. et al . Anti-HIV-1 protostane triterpenes and digeranylbenzophenone from trunk bark and stems of Garcinia speciosa . Planta Med. 2003; 69 1141-6
Prof. Dr. Ji-Jun Chen
State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
The Chinese Academy of Sciences
Kunming 650204
Yunnan
People’s Republic of China
Phone: +86-871-5223265
Fax: +86-871-5223265
Email: chenjj@mail.kib.ac.cn