Subscribe to RSS
DOI: 10.1055/s-2005-873141
Cytotoxic Arylnaphthalide Lignan Glycosides from the Aerial Parts of Phyllanthus taxodiifolius
Publication History
Received: March 16, 2005
Accepted: May 30, 2005
Publication Date:
14 October 2005 (online)
Abstract
The arylnaphthalide lignan glycosides, taxodiifoloside (1), cleistanthoside A (2), cleistanthin A (3) and cleistanthin A methyl ether (4), together with a triterpene, glochidone (5), have been isolated from the aerial parts of Phyllanthus taxodiifolius. The structures were established using spectral and chemical methods. Compounds 3 and 4, as well as the derivatives 2a and 3a exhibited potent cytotoxic activities with GI50 values in the range of 10-7 - 10-9 M in five cultured mammalian cancer cell lines while the new compound 1 showed moderate activity (GI50 in the order of 10-6 M). Compounds 2 and 5 were inactive in all tested cell lines.
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Smitinand T. Thai Plant Names. Revised Edition by the Forest Herbarium, Bangkok Pra Cha Chon Co Ltd 2001: p 412
- 2 Sastry K V, Rao E V. Isolation and structure of cleistanthoside A. Planta Med. 1983; 47 227-9
- 3 Govindachari T R, Sathe S S, Viswanathan N, Pai B R, Srinivasan M. Chemical constituents of Cleistanthus collinus (Roxb.) Tetrahedron. 1969; 25 2815-21
- 4 Anjaneyulu A SR, Atchuta Ramaiah P, Ramachandra Row L, Venkateswarlu R. New lignans from the heartwood of Cleistanthus collinus . Tetrahedron. 1981; 37 3641-52
- 5 Ramesh C, Ravindranath N, Ram T S, Das B. Arylnaphthalide lignans from Cleistanthus collinus . Chem Pharm Bull. 2003; 51 1299-300
- 6 Ganguly A K, Govindachari T R, Mohamed P A, Rahimtulla A D, Viswanathan N. Chemical constituents of Glochidion hohemnackeri . Tetrahedron. 1966; 22 1513-9
- 7 Srivastava R, Kulshreshtha D K. Triterpenoids from Glochidion heyneanum . Phytochemistry. 1988; 27 3575-8
-
8 Copies of the original spectra are obtainable from the author of correspondence . .
- 9 Charlton J L, Oleschuk C J, Chee G -L. Hindered rotation in arylnaphthalene lignans. J Org Chem. 1996; 61 3452-7
- 10 Pradheepkumar C P, Shanmugam G. Anticancer potential of cleistanthin A isolated from the tropical plant Cleistanthus collinus . Oncol Res. 1999; 11 225-32
- 11 Pradheepkumar C P, Panneerselvam N, Shanmugam G. Cleistanthin A causes DNA strand breaks and induces apoptosis in cultured cells. Mutat Res. 2000; 464 185-93
- 12 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxic assay for anticancer-drug screening. J Natl Cancer Inst. 1990; 82 1107-12
Dr. Patoomratana Tuchinda
Department of Chemistry
Faculty of Science
Mahidol University
Rama 6 Road
Bangkok 10400
Thailand
Fax: +66-02-3547151
Email: scptc@mahidol.ac.th
- www.thieme-connect.de/ejournals/toc/plantamedica