Subscribe to RSS
DOI: 10.1055/s-0029-1240689
© Georg Thieme Verlag KG Stuttgart · New York
Isoflavonoids from the Roots of Campylotropis hirtella
Publication History
received July 27, 2009
revised Nov. 11, 2009
accepted Nov. 16, 2009
Publication Date:
14 December 2009 (online)
Abstract
From the dried roots of Campylotropis hirtella (Franch.) Schindl., five novel isoflavonoids, 3(S)-7,2′,4′-trihydroxy-5,5′-dimethoxy-6-(3-methylbut-2-enyl)-isoflavan (1), 3(S)-2′,4′-dihydroxy-5,5′-dimethoxy-(6′′,6′′-dimethylpyrano)-(2′′,3′′:7,6)-isoflavan (2), 3(R)-5,4′-dihydroxy-2′-methoxy-3′-(3-methylbut-2-enyl)-(6′′,6′′-dimethylpyrano)-(7,6 : 2′′,3′′)-isoflavanone (3), 3(R)-5,4′-dihydroxy-2′-methoxy-(6′′,6′′-dimethylpyrano)-(7,6: 2′′,3′′)-isoflavanone (4), and 3(R)-5,4′-dihydroxy-7,2′-dimethoxy-6-geranylisoflavanone (5) were isolated. The structures of the compounds were elucidated on the basis of spectroscopic analysis. All isolates exhibited good immunosuppressive activities on mitogen-induced splenocyte proliferation, and their cytotoxicity on splenic lymphocytes was also tested.
Key words
Campylotropis hirtella - Leguminosae - isoflavonoids - immunosuppressive activities
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Pharmacopoeia Committee of the People's Republic of China Edita .Pharmacopoeia of the People's Republic of China. Beijing; People's Hygiene Press 1977: 30-31
- 2 Lu X Z, Xu W B, Shen J X. Chemical studies on Campylotropis hirtella. Zhongguo Zhongyao Zazhi. 1997; 22 680-683
- 3 Qin L, Chen X M, Chen W X, Yang L, Zhang C K. Study on tannins from Campylotropis hirtella. Tianran Chanwu Yanjiu Yu Kaifa. 1991; 3 31-34
- 4 Han H Y, Wang X H, Wang N L, Ling M T, Wong Y C, Yao X S. Lignans isolated from Campylotropis hirtella (Franch.) Schindl. decreased prostate specific antigen and androgen receptor expression in LNCaP cells. J Agric Food Chem. 2008; 56 6928-6935
- 5 Wen P, Han H Y, Wang N L, Yao X S. Flavonoids from Campylotropis hirtella (Franch.) Schindl. and their bioactivities. J Shenyang Pharm Univ. 2008; 25 448-453
- 6 Han H Y, Wen P, Liu H W, Wang N L, Yao X S. Coumarins from Campylotropis hirtella (Franch.) Schindl. and their inhibitory activity on prostate specific antigen secreted from LNCaP Cells. Chem Pharm Bull. 2008; 56 1338-1341
- 7 Shou Q Y, Fu R Z, Tan Q, Shen Z W. Geranylated flavonoids from the roots of Campylotropis hirtella and their immunosuppressive activities. J Agric Food Chem. 2009; 57 6712-6719
- 8 Shou Q Y, Tan Q, Shen Z W. Hirtellanines A and B, a pair of isomeric isoflavonoid derivatives from Campylotropis hirtella and their immunosuppressive activities. Bioorg Med Chem Lett. 2009; 19 3389-3391
- 9 Sairafianpour M, Kayser O, Christensen J, Asfa M, Witt M, Staerk D, Jaroszewski J W. Leishmanicidal and antiplasmodial activity of constituents of Smirnowia iranica. J Nat Prod. 2002; 65 1754-1758
- 10 Kurosawa K, Ollis W D, Redman B T, Sutherland I O, Alves H M, Gottlieb O R. Absolute configurations of isoflavans. Phytochemistry. 1978; 17 1423-1426
- 11 Versteeg M, Bezuidenhoudt B C B, Ferreira D. Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavans. Tetrahedron. 1999; 55 3365-3376
- 12 Nomura T, Fukai T, Katayanagi M. Studies on the constituents of the cultivated mulberry tree. III. Isolation of four new flavones, Kuwanon A, B, C and oxydihydromorusin from the root bark of Morus alba L. Chem Pharm Bull. 1978; 26 1453-1458
-
13 Nomura T, Fukai T.
Phenolic constituents of licorice (Glycyrrhiza species). Herz W, Kirby GW, Moore RE, Steglich W, Tamm C Progress in the chemistry of organic natural products, Vol. 73. Vienna; Springer 1998: 69-73 - 14 Tanaka H, Oh-Uchi T, Etoh H, Sako M, Asai F, Fukai T, Sato M, Murata J, Tateishi Y. Isoflavonoids from roots of Erythrina zeyheri. Phytochemistry. 2003; 64 753-758
- 15 Miyase T, Sano M, Yoshino K, Nonaka K. Antioxidants from Lespedeza homoloba (III). Phytochemistry. 1999; 52 311-319
- 16 Yahara S, Ogata T, Saijo R, Konishi R, Yamahara J, Miyahara K, Nohara T. Isoflavan and related compounds from Dalbergia odorifera. Chem Pharm Bull. 1989; 37 979-987
- 17 Galeffi C, Rasoanaivo P, Federici E, Palazzino G, Nicoletti M R, Rasolondratovo B. Two prenylated isoflavanones from Millettia pervilleana. Phytochemistry. 1997; 45 189-192
Prof. Dr. Zheng-Wu Shen
School of Pharmacy
Shanghai University of Traditional Chinese Medicine
1200 Cailun Road
201203 Shanghai
People's Republic of China
Phone: + 86 5 13 82 19 80 01
Fax: + 86 5 13 82 19 80 03
Email: jeff_shen_1999@yahoo.com
- www.thieme-connect.de/ejournals/toc/plantamedica