Browse > Article

Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity  

Tapondjou, Leon Azefack (Department of Chemistry, Faculty of Science, University of Dschang)
Lontsi, David (Department of Organic Chemistry, Faculty of Science, University of Yaounde)
Sondengam, Beiham Luc (Department of Organic Chemistry, Faculty of Science, University of Yaounde)
Choudhary, Muhammad Iqbal (International Center for Chemical Sciences, HEJ Research Institute of Chemistry, University of Karachi)
Park, Hee-Juhn (Division of Applied Plant Sciences, Sangji University)
Choi, Jong-Won (College of Pharmacy, Kyungsung University)
Lee, Kyung-Tae (College of Pharmacu, Kyung Hee University)
Publication Information
Archives of Pharmacal Research / v.25, no.3, 2002 , pp. 270-274 More about this Journal
Abstract
Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.
Keywords
Mitragyna stipulosa; Triterpenoid; Ursane-type; Cytotoxicity; Structure-activity relationship;
Citations & Related Records

Times Cited By Web Of Science : 8  (Related Records In Web of Science)
Times Cited By SCOPUS : 10
연도 인용수 순위
1 Ahmad, V. U. and Rahman, A. U., Handbook of Natural Products Data, Vol II, pp. 835-836, Elsevier Science, Amsterdam (1994)
2 Safir, O, Fkih-Tetounai, S, De Tommasi, N, and Aquino, R. Saponins from Zygophylum gaetulum. Journal of Natual Products. 61,130-4 (1998)   DOI   ScienceOn
3 Park, H. J., Kwon, S. H., Lee, J. H., Lee, K. H., Miyamoto, K., and Lee, K. T., Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides. Planta Medica, 67,118-121 (2001)   DOI   ScienceOn
4 Aquino, Q., Simone, F. D., Pizza, C., Cerri, R. and de Mello, J. F., Plant metabolites. Structure and in vitro antiviral activity of quinovic acid glycosides from Uncaria tomentosa and Guettarda platypoda. Journal of Natural Products 52, 679-685 (1989)   DOI   PUBMED
5 Park, H. J., Lee, M. S., Young, H. S., Choi, J. S., and Jung, W. T., Phytochemical study for botanical utilization of the fruits of Malus baccata. Korean Journal of Pharmacognosy, 24, 282-288(1993)
6 Kim, Y. K., Yoon, S. K., Ryu, S., Cytotoxic triterpenes from stem bark of Physocarpus intermedius. Planta Medica, 66, 485-486(2000)   DOI   ScienceOn
7 Lee, K. T., Sohn I. C., Park, H. J., Kim, D.W., Jung, G. O. and Park. K. Y., Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides Isolated from the stem bark of Kalopanax pictus. Planta Medica, 66, 329-332 (2000)   DOI   ScienceOn
8 Denizot, F and Lang, R. J., Rapid colorimetric assay for cell growth and survival: modification to the tetrazolium dye procedure giving improved sensitivity and reliability. Journal of Immunological Methods, 89, 271-277 (1996)   DOI   ScienceOn
9 Ahmad, V. U. and Basha, A., Spectroscopic data of saponins- The triterpenoid glycosides Vol. III, pp. 2839-2839, CRC press, New York (2000)