Anthranoid Compounds with Antiprotozoal Activity from Vismia orientalis

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