RSS-Feed abonnieren
DOI: 10.1055/s-2004-827199
© Georg Thieme Verlag KG Stuttgart · New York
Anthranoid Compounds with Antiprotozoal Activity from Vismia orientalis
Publikationsverlauf
Received: January 5, 2004
Accepted: May 15, 2004
Publikationsdatum:
24. August 2004 (online)
Abstract
A phytochemical investigation of the 80% ethanolic extract of stem bark of Vismia orientalis Engl. (Guttiferae or Clusiaceae), a plant used in traditional medicine in Tanzania, resulted in the isolation and spectroscopic characterisation of 3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone, emodin, vismione D and bianthrone A1. Vismione D exhibited a broad range of antiprotozoal activities against Trypanosoma brucei rhodesiense and T. cruzi (IC50 < 10 μg/mL), Leishmania donovani (IC50 0.37 μg/mL) and Plasmodium falciparum strain K1 (IC50 1.0 μg/mL). However, it was also slightly cytotoxic against human L6 cells (IC50 4.1 μg/mL). Emodin showed antileishmanial activity (IC50 2.0 μg/mL), while its IC50 against L6 cells was 20.3 μg/mL. Other antiprotozoal activities observed for emodin against both Trypanosoma species and P. falciparum, for bianthrone A1 against T. b. rhodesiense and P. falciparum, and for 3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone against T. b. rhodesiense, L. donovani and P. falciparum were in the range of 10 to 50 μg/mL. None of the compounds showed antibacterial or antiviral (including also HIV) activity.
Key words
Vismia orientalis - Guttiferae - Clusiaceae - 3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone - bianthrone A1 - emodin - vismione D - Plasmodium falciparum - Leishmania - Trypanosoma
References
- 1 Polhill R M. Guttiferae. In: Flora of Tropical East Africa. 1978: p. 32
- 2 Duke J A. In: Amazonian Ethnobotanical Dictionary. 1994: p 181
- 3 Schultes R E. De Plantis toxicaris e mundo novo tropicale commentationes. XXX. Biodynamic guttiferous plants of the Northwestern Amazon. Bot Mus Leafl Harv Univ. 1983; 29 49-57
- 4 Barrett B. Medicinal plants of Nicaragua’s Atlantic coast. Econ Bot. 1994; 48 8-20
- 5 Weenen H, Nkunya M HH, Bray D H, Mwasumbi L B, Kinabo L S. Antimalarial activity of Tanzanian medicinal plants. Planta Medica. 1990; 56 368-70
- 6 Botta B, Delle Monache F, Delle Monache G, Marini Bettolo G B, Oguakwa J U. 3-Geranyloxy-6-methyl-1,8-dihydroxyanthraquinone and vismiones C, D and E from Psorospermum febrifugum . Phytochemistry. 1983; 22 539-42
- 7 Cohen P A, Towers G HN. Anthraquinones and phenanthroperylenequinones from Nephroma laevigatum . J Nat Prod. 1995; 58 520-6
- 8 Marston A, Chapuis J -C, Sordat B, Msonthi J D, Hostettmann K. Anthracenic derivatives from Psorospermum febrifugum and their in vitro cytotoxicities to a human colon carcinoma cell line. Planta Medica. 1986; 52 207-10
- 9 Baltz T, Baltz D, Giroud C, Crockett J. Cultivation in a semi-defined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense . EMBO J. 1985; 4 1273-7
- 10 Räz B, Iten M, Grether-Bühler Y, Kaminsky R and Brun R. The Alamar blue assay to determine drug sensitivity of African trypanosomes (T. b. rhodesiense and T. b. gambiense) in vitro . Acta Trop. 1997; 68 139-47
- 11 Cunningham I. New culture medium for maintenance of tsetse tissues and growth of trypanosomatids. J Protozool. 1977; 24 325-9
-
12 Matile H, Pink J RL. Plasmodium falciparum malaria parasite cultures and their use in immunology. In: Lefkovits I, Pernis B, editors
Immunological Methods . San Diego; Academic Press 1990: pp 221-34 - 13 Cos P, Hermans N, De Bruyne T, Apers S, Sindambiwe J B. Vanden Berghe D, Pieters L, Vlietinck AJ. Further evaluation of Rwandan medicinal plant extracts for their antimicrobial and antiviral activities. J Ethnopharmacol. 2002; 79 155-63
- 14 Cos P, Hermans N, De Bruyne T, Apers S, Sindambiwe J B, Witvrouw M, De Clercq E, Vanden Berghe D, Pieters L, Vlietinck A J. Antiviral activity of Rwandan medicinal plants against human immunodeficiency virus type-1. Phytomedicine. 2002; 9 62-8
- 15 Meyer B N, Ferrigni E, Putnam J E, Jacobsen L B, Nichols D E, McLaughlin J L. Brine shrimp: A convenient general bioassay for and active plant constituents. Planta Medica. 1982; 45 31-4
- 16 Botta B, Delle Monache F, Delle Monache G, Marini Bettolo G B, Msonthi J D. Prenylated bianthrones and vismione F from Psorospermum febrifugum . Phytochemistry. 1985; 24 827-30
- 17 Sibanda S, Nyanyira C, Nicoletti M, Galeffi C. Ochnabianthrone: A trans-9,9’-bianthrone from Ochna pulchra . Phytochemistry. 1990; 29 3974-6
- 18 Del Rayo Camacho M, Kirby G C, Warhurst D C, Croft S L, Phillipson J D. Oxaporphine alkaloids and quinones from Stephania dinklagei and evaluation of their antiprotozoal activities. Planta Medica. 2000; 66 478-80
- 19 Sittie A A, Lemmich E, Olsen C E, Hviid L, Kharazmi A, Nkrumah F K, Christensen S B. Structure-activity studies: In vitro antileishmanial and antimalarial activities of anthraquinones from Morinda lucida . Planta Medica. 1999; 65 259-61
- 20 Hamburger M, Marston A, Hostettmann K. Search for new drugs of plant origin. Adv Drug Res. 1991; 20 167-215
- 21 François G, Steenackers T, Aké Assi L, Seglich W, Lamottke K, Holenz J, Bringmann G. Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum: structure-activity relationships. Parasitol Res. 1999; 85 582-8
Zakaria H. Mbwambo
Institute of Traditional Medicine
Muhimbili University College of Health Sciences
P. O. Box 65001
Dar es Salaam
Tanzania
eMail: zmbwambo@muchs.ac.tz