Subscribe to RSS
DOI: 10.1055/s-2006-946639
Quinolizidine Alkaloids with Anti-HBV Activity from Sophora tonkinensis
Publication History
Received: January 14, 2006
Accepted: April 29, 2006
Publication Date:
19 June 2006 (online)
Abstract
A new matrine-type alkaloid, (-)-14β-hydroxyoxymatrine (1), was isolated from the roots and rhizomes of Sophora tonkinensis Gapnep. (Leguminosae), together with five known matrine-type alkaloids, (-)-14β-hydroxymatrine (2), (+)-oxymatrine (3), (+)-matrine (4), (+)-sophoranol (5), and (-)-5α-hydroxysophocarpine (6), as well as with two known cytisine-type alkaloids, (-)-cytisine (7) and (-)-N-methylcytisine (8). Their structures were elucidated by spectroscopic methods. Compounds 1, 5 and 7 showed potent anti-HBV activity with an inhibitory potency against HBsAg secretion of 22.6 %, 31.1 % and 33.2 %, and against HBeAg secretion of 30.4 %, 26.3 % and 27.8 %, respectively.
References
- 1 Ding P L, Liao Z X, Huang H, Zhou P, Chen D F. (+)-12α-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens . Bioorg Med Chem Lett. 2006; 16 1231-5
- 2 State Pharmacopoeia Commission of PRC. Pharmacopoeia of the People’s Republic of China. Vol. 1 Beijing; Chemical Industry Press 2005: p 19-20
- 3 Fan H W, Lu J H, Zhang R. Studies on the antibacterial and antiviral activities of matrine-type alkaloids, and its effect on inducing interferon production. Zhong Yi Yao Xin Xi. 2000; 17 75-6
- 4 Xiao P, Li J S, Kubo H, Saito K, Murakoshi I, Ohmiya S. (-)-14β-Hydroxymatrine, a new lupin alkaloid from the roots of Sophora tonkinensis . Chem Pharm Bull. 1996; 44 1951-3
- 5 Xiao P, Kubo H, Komiya H, Higashiyama K, Yan Y N, Li J S. et al . (-)-14β-Acetoxymatrine and (+)-14α-acetoxymatrine, two new matrine-type lupin alkaloids from the leaves of Sophora tonkinensis . Chem Pharm Bull. 1999; 47 448-50
- 6 Zhang L Z, Li J S, Houghton P J, Jackson S, Twentyman P R. Alkaloids in Sophora alopecuroides seed and relevant tests for activity. Zhongguo Zhong Yao Za Zhi. 1997; 22 740-3
- 7 Zhao Y Y, Pang Q Y, Liu J B, Chen Y Y, Lou Z C. Studies on the alkaloids of Sophora flavescens . Tian Ran Chan Wu Yan Jiu Yu Kai Fa. 1994; 6 10-3
- 8 Saito K, Arai N, Sekine T, Ohmiya S, Kubo H, Otomasu H. et al . (-)-5α-Hydroxysophocarpine, a new lupin alkaloid from the seeds of Sophora flavescens var. angustifolia . Planta Med. 1990; 56 487-8
- 9 Takamatsu S, Saito K, Ohmiya S, Ruangrungsi N, Murakoshi I. Lupin alkaloids from Sophora exigua . Phytochemistry. 1991; 30 3793-5
- 10 Ding P L, Chen D F. The pharmacological activities, clinical applications and side effects of the Chinese drug ‘Shan-dou-gen’ and its preparations. Zhongguo Lin Chuang Yao Xue Za Zhi. 2003; 12 315-8
- 11 Wu T, Huang H, Zhou P. The inhibitory effects of enduracidin on hepatitis B virus in vitro . Zhongguo Bing Du Xue. 1998; 13 45-9
Dr. Dao-Feng Chen
Department of Pharmacognosy
School of Pharmacy
Fudan University
138 Yi Xue Yuan Road
Shanghai 200032
People’s Republic of China
Phone: +86-21-5423-7453
Fax: +86-21-6417-0921
Email: dfchen@shmu.edu.cn