Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: In vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies

Antimicrobial Agents and Chemotherapy

Volumn 50, Issue 4, 2006, Pages 1352-1364

  Tasdemir, Deniz ^a   Kaiser, Marcel ^b   Brun, Reto ^b   Yardley, Vanessa ^c   Schmidt, Thomas J ^d   Tosun, Fatma ^e   Rüedi, Peter ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^d UNIVERSITY OF MÜNSTER   (Germany)

^e GAZI UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYDAIDZEIN; 3 HYDROXYFLAVONE; 3,7 DIHYDROXYFLAVONE; 5,7 DIMETHOXY 8 METHYLFLAVANONE; 6,7 DIHYDROXYFLAVONE; 6,7 DIHYROXYFLAVONE; 7,8 DIHYDROXYFLAVONE; 7,8,3',4' TETRAHYDROXYFLAVONE; AGLYCONE; CAFFEIC ACID; CATECHOL; CHRYSIN DIMETHYL ETHER; CIRSIMARITIN; DIHYDROCAFFEIC ACID; FISETIN; FLAVONOID GLYCOSIDE; FLAVONOL DERIVATIVE; GALLIC ACID; GALLOCATECHIN GALLATE; GENISTEIN; LUTEOLIN; LUTEOLIN 7 GLUCOSIDE; MYRICETIN; PYROGALLOL; QUERCETIN; RHAMNETIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIMICROBIAL ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; CULTURE MEDIUM; DISEASE MODEL; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; FEMALE; IC 50; LEISHMANIA DONOVANI; LEISHMANIASIS; MAMMAL CELL; MOUSE; NONHUMAN; PARASITE CULTIVATION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; STRUCTURE ANALYSIS; TRYPANOSOMA CRUZI; TRYPANOSOMA RHODESIENSE; TRYPANOSOMIASIS;

ANIMALS; ANTIPROTOZOAL AGENTS; CELL LINE; FEMALE; FLAVONOIDS; LEISHMANIA DONOVANI; LEISHMANIASIS; MICE; MICE, INBRED BALB C; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMA CRUZI; TRYPANOSOMIASIS;

EID: 33645755408     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.50.4.1352-1364.2006     Document Type: Article

References (36)

1. Baltz, T., D. Baltz, C. Giroud, and J. Crockett. 1985. Cultivation in a semi-defined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense. EMBO J. 4:1273-1277.
2. Bürgi, C. B. 1991. Isolierung, Strukturaufkiaerung und Synthese von anti-oxidativ wirksamen langkettigen Alkylphenolen aus Plectranthus albidus (Labiatae). Ph.D. thesis. University of Zurich, Zurich, Switzerland.
3. Camacho, M. D. R., J. D. Phillipson, S. L. Croft, D. Marley, G. C. Kirby, and D. C. Warhurst. 2002. Assessment of the antiprotozoal activity of Galphimia glauca and the isolation of new nor-secofriedelanes and nor-friedelanes. J. Nat. Prod. 65:1457-1461.
4. Croft, S. L., and V. Yardley. 1999. Animal models of visceral leishmaniasis, p. 783-787. In O. Zak (ed.), Handbook of animal models of infection. Academic Press, Inc., New York, N.Y.
5. Cunningham, I. 1977. New culture medium for maintenance of tsetse tissues and growth of trypanosomatids. J. Protozool. 24:325-329.
6. Desjeux, P. 2004. Leishmaniasis: current situation and new perspectives. Comp. Immunol. Microbiol. Infect. Dis. 27:305-318.
7. Dias, J. C. P., A. C. Silveira, and C. J. Schofield. 2002. The impact of Chagas disease control in Latin America. A review. Mem. Inst. Oswaldo Cruz 97: 603-612.
8. Fusai, T., Y. Boulard, R. Durand, M. Paul, C. Bories, D. Rivollet, A. Astier, R. Houin, and M. Deniau. 1997. Ultrastructural changes in parasites induced by nanoparticle-bound pentamidine in a Leishmania major/mouse model. Parasite 4:133-139.
9. Grael, C. F., S. Albuquerque, and J. L. Lopes. 2005. Chemical constituents of Lychnophora pohlii and trypanocidal activity of crude plant extracts and of isolated compounds. Fitoterapia 76:73-82.
10. Harborne, J. B., and C. A. Williams. 2000. Advances in flavonoid research since 1992. Phytochemistry 55:481-504.
11. Hollman, P. C. H., J. H. M. de Vries, S. D. van Leeuwen, M. J. B. Mengelers, and M. B. Katan. 1995. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 62:1276-1282.
12. Jordão, C. O., W. Vichnewski, G. E. P. de Souza, S. Albuquerque, and J. L. C. Lopes. 2004. Trypanocidal activity of chemical constituents of Lychnophora salicifolia Mart. Phytother. Res. 18:332-334.
13. Juch, M. 1997. Isolierung, Strukturaufklaerung und Synthese von langkettigen Alkyloxy-catecholen aus Labiaten als Antioxidanten und Inhibitoren von Lipoxygenase. Ph.D. thesis. University of Zurich, Zurich, Switzerland.
14. Kayser, O. 2000. Nanosuspensions for the formulation of aphidicolin to improve drug targeting effects against Leishmania infected macrophages. Int. J. Pharm. 196:253-256.
15. Kayser, O., and A. F. Kiderlen. 2003. Delivery strategies for antiparasitics. Expert Opin. Investig. Drugs 12:197-207.
16. Kennedy, P. G. E. 2004. Human African trypanosomiasis of the CNS: current issues and challenges. J. Clin. Investig. 113:496-504.
17. Kirmizibekmez, H., I. Çalis, R. Perozzo, R. Brun, A. A. Dönmez, A. Linden, P. Rüedi, and D. Tasdemir. 2004. Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP reductase, a crucial enzyme in fatty acid biosynthesis. Planta Med. 70:711-717.
18. Koide, T., M. Nose, M. Inoue, Y. Ogihara, Y. Yabu, and N. Ohta. 1998. Trypanocidal effects of gallic acid and related compounds. Planta Med. 64:27-30.
19. Kolodziej, H., and A. F. Kiderlen. 2005. Antileishmanial activity and immune modulatory effects of tannins and related compounds on Leishmania parasitised RAW 264.7 cells. Phytochemistry 66:2056-2071.
20. Lill, M. A., A. Vedani, and M. Dobler. 2004. Raptor: combining dual-shell representation, induced-fit simulation, and hydrophobicity scoring in receptor modeling: application toward the simulation of structurally diverse ligand sets. J. Med. Chem. 47:6174-6186.
21. Liu, G., and P. Rüedi. 1996. Phyllocladanes (13-beta-kaurenes) from Plectranthus ambiguus. Phytochemistry 41:1563-1568.
22. Livingstone, D. 1995. Data analysis for chemists-applications to QSAR and chemical product design. Oxford University Press, Oxford, United Kingdom.
23. Mamani-Matsuda, M., J. Rambert, D. Malvy, H. Lejoly-Boisseau, S. Daulouède, D. Thiolat, S. Coves, P. Courtois, P. Vincendeau, and M. D. Mossalayi. 2004. Quercetin induces apoptosis of Trypanosoma brucei gambiense and decreases the proinflammatory response of human macrophages. Antimicrob. Agents Chemother. 48:924-929.
24. Manach, C., and J. L. Donovan. 2004. Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic. Res. 38:771-785.
25. Manach, C., A. Scalbert, C. Morand, C. Remesy, and L. Jimenez. 2004. Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 79:727-747.
26. Mittra, B., A. Saha, A. R. Chowdury, C. Pal, S. Mandal, S. Mukhopadhyay, S. Bandyopadhyay, and H. K. Majumder. 2000. Luteolin, an abundant dietary component is a potent anti-leishmanial agent that acts by inducing topoisomerase II-mediated kinetoplast DNA cleavage leading to apoptosis. Mol. Med. 6:527-541.
27. MOE. 2005. MOE Molecular Operating Environment [Online.] http://www .chemcomp.com/. Chemical Computing Group, Montreal, Quebec, Canada.
28. Nikolic, D., and R. B. van Breemen. 2004. New metabolic pathways for flavanones catalyzed by rat liver microsomes. Drug Metab. Dispos. 32:387-397.
29. Paveto, C., M. C. Güida, M. I. Esteva, V. Martino, J. Coussio, M. M. Flawiá, and H. N. Torres. 2004. Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins. Antimicrob. Agents Chemother. 48:69-74.
30. Radtke, O. A., L. Y. Foo, Y. Lu, A. F. Kiderlen, and H. Kolodziej. 2003. Evaluation of sage phenolics for their antileishmanial activity and modulatory effects on interleukin-6, interferon and tumor necrosis factor-α-release in RAW 264.7 cells. Z. Naturforsch. C 58c:395-400.
31. Räz, B., M. Iten, Y. Grether-Bühler, R. Kaminsky, and R. Brun. 1997. The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T. b. rhodesiense and T. b. gambiense) in vitro. Acta Trop. 68:139-147.
32. Takeara, R., S. Albuquerque, N. P. Lopes, and J. L. C. Lopes. 2003. Trypanocidal activity of Lychnophora staavioides Mart. (Vernonieae, Asteraceae). Phytomedicine 10:490-493.
33. Taleb-Contini, S. H., M. J. Salvador, J. M. Balanco, S. Albuquerque, and D. C. R. de Oliveira. 2004. Antiprotozoal effect of crude extracts and flavonoids isolated from Chromolaena hirsuta (Asteraceae). Phytother. Res. 18:250-254.
34. Tasdemir, D., I. Çalis, and O. Sticher. 1998. Labdane diterpenes from Leonurus persicus. Phytochemistry 49:137-143.
35. Tosun, F., and C. Akyüz. 1997. Flavonoids of Gonocytisus angulatus. Pharm. Sci. 3:377-378.
36. Williamson, G., D. Barron, K. Shimoi, and J. Terao. 2005. In vitro biological properties of flavonoid conjugates found in vivo. Free Radic. Res. 39:457-469.