Compounds structurally related to ellagic acid show improved antiplasmodial activity

Antimicrobial Agents and Chemotherapy

Volumn 53, Issue 2, 2009, Pages 622-630

  Sturm, Nicole ^a   Hu, Ying ^a   Zimmermann, Herbert ^b   Fritz Wolf, Karin ^a,b   Wittlin, Sergio ^c   Rahlfs, Stefan ^a   Becker, Katja ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROQUINE; CORULEOELLAGIC ACID; ELLAGIC ACID; FLAVELLAGIC ACID; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE; HEME; OXIDOREDUCTASE; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DOWN REGULATION; ENZYME ACTIVITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; PARASITE SURVIVAL; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; TROPHOZOITE;

ANIMALS; ANTIMALARIALS; CELLS, CULTURED; CHLOROQUINE; DNA, COMPLEMENTARY; DRUG RESISTANCE; ELLAGIC ACID; GLUTATHIONE PEROXIDASE; GLUTATHIONE TRANSFERASE; HEME; HUMANS; KINETICS; PLASMODIUM FALCIPARUM; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

EID: 59749092672     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00544-08     Document Type: Article

References (38)

1. Ahmadi, R., S. Urig, M. Hartmann, B. M. Helmke, S. Koncarevic, B. Allenberger, C. Kienhoefer, M. Neher, H. H. Steiner, A. Unterberg, C. Herold-Mende, and K. Becker. 2006. Antiglioma activity of 2,2′:6′,2″-terpyridineplatinum(II) complexes in a rat model - effects on cellular redox metabolism. Free Radic. Biol. Med. 40:763-778.
2. Banzouzi, J. T., R. Prado, H. Menan, A. Valentin, C. Roumestan, M. Mallie, Y. Pelissier, and Y. Blache. 2002. In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid. J. Ethnopharmacol. 81:399-401.
3. Becker, K., L. Tilley, J. L. Vennerstrom, D. Roberts, S. Rogerson, and H. Ginsburg. 2004. Oxidative stress in malaria parasite-infected erythrocytes: host-parasite interactions. Int. J. Parasitol. 34:163-189.
4. Bohle, D. S., A. D. Kosar, and P. W. Stephens. 2002. Phase homogeneity and crystal morphology of the malaria pigment beta-hematin. Acta Crystallogr. D Biol. Crystallogr. 58:1752-1756.
5. Constantinou, A., G. D. Stoner, R. Mehta, K. Rao, C. Runyan, and R. Moon. 1995. The dietary anticancer agent ellagic acid is a potent inhibitor of DNA topoisomerases in vitro. Nutr. Cancer 23:121-130.
6. Das, M., D. R. Bickers, and H. Mukhtar. 1984. Plant phenols as in vitro inhibitors of glutathione S-transferase(s). Biochem. Biophys. Res. Commun. 120:427-433.
7. Das, M., S. V. Singh, H. Mukhtar, and Y. C. Awasthi. 1986. Differential inhibition of rat and human glutathione S-transferase isoenzymes by plant phenols. Biochem. Biophys. Res. Commun. 141:1170-1176.
8. Dell'Agli, M., S. Parapini, N. Basilico, L. Verotta, D. Taramelli, C. Berry, and E. Bosisio. 2003. In vitro studies on the mechanism of action of two compounds with antiplasmodial activity: ellagic acid and 3,4,5-trimethoxyphenyl(6′-O-aalloyl)-beta-D-glucopyranoside. Planta Med. 69:162-164.
9. Deponte, M., and K. Becker. 2005. Glutathione S-transferase from malarial parasites: structural and functional aspects. Methods Enzymol. 401:241-253.
10. Desjardins, R. E., C. J. Canfield, J. D. Haynes, and J. D. Chulay. 1979. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 16:710-718.
11. Färber, P. M., L. D. Arscott, C. H. Williams, Jr., K. Becker, and R. H. Schirmer. 1998. Recombinant Plasmodium falciparum glutathione reductase is inhibited by the antimalarial dye methylene blue. FEBS Lett. 422:311-314.
12. Fivelman, Q. L., I. S. Adagu, and D. C. Warhurst. 2004. Modified fixed-ratio isobologram method for studying in vitro interactions between atovaquone and proguanil or dihydroartemisinin against drug-resistant strains of Plasmodium falciparum. Antimicrob. Agents Chemother. 48:4097-4102.
13. Fritz-Wolf, K., A. Becker, S. Rahlfs, P. Harwaldt, R. H. Schirmer, W. Kabsch, and K. Becker. 2003. X-ray structure of glutathione S-transferase from the malarial parasite Plasmodium falciparum. Proc. Natl. Acad. Sci. USA 100:13821-13826.
14. Geevananda, Y. A., P. Gunawardana, N. S. Kumar, and M. U. S. Sultanbawa. 1979. Three hydroxy ellagic acid methyl ethers, chrysophanol and scopoletin from Shorea worthingtonii and Vatica obscura. Phytochemistry 18:1017-1019.
15. Gromer, S., L. D. Arscott, C. H. Williams, Jr., R. H. Schirmer, and K. Becker. 1998. Human placenta thioredoxin reductase. Isolation of the selenoenzyme, steady state kinetics, and inhibition by therapeutic gold compounds. J. Biol. Chem. 273:20096-20101.
16. Harwaldt, P., S. Rahlfs, and K. Becker. 2002. Glutathione S-transferase of the malarial parasite Plasmodium falciparum: characterization of a potential drug target. Biol. Chem. 383:821-830.
17. Hayeshi, R., I. Mutingwende, W. Mavengere, V. Masiyanise, and S. Mukanganyama. 2007. The inhibition of human glutathione S-transferases activity by plant polyphenolic compounds ellagic acid and curcumin. Food Chem. Toxicol. 45:286-295.
18. Hiller, N., K. Fritz-Wolf, M. Deponte, W. Wende, H. Zimmermann, and K. Becker. 2006. Plasmodium falciparum glutathione S-transferase - structural and mechanistic studies on ligand binding and enzyme inhibition. Protein Sci. 15:281-289.
19. Ignatushchenko, M. V., R. W. Winter, H. P. Bachinger, D. J. Hinrichs, and M. K. Riscoe. 1997. Xanthones as antimalarial agents; studies of a possible mode of action. FEBS Lett. 409:67-73.
20. Irmler, A., A. Bechthold, E. Davioud-Charvet, V. Hofmann, R. Réau, S. Gromer, R. H. Schirmer, and K. Becker. 2002. Disulfide reductases-current developments, p. 803-815. In S. Chapman, R. Perham, and N. Scrutton (ed.), Flavins and flavoproteins, vol. 14. Walter de Gruyter, New York, NY.
21. Kanzok, S. M., R. H. Schirmer, I. Turbachova, R. Iozef, and K. Becker. 2000. The thioredoxin system of the malaria parasite Plasmodium falciparum. Glutathione reduction revisited. J. Biol. Chem. 275:40180- 40186.
22. Lambros, C., and J. P. Vanderberg. 1979. Synchronization of Plasmodium falciparum erythrocytic stages in culture. J. Parasitol. 65:418-420.
23. Loarca-Piña, G., P. A. Kuzmicky, E. G. de Mejia, and N. Y. Kado. 1998. Inhibitory effects of ellagic acid on the direct-acting mutagenicity of aflatoxin B1 in the Salmonella microsuspension assay. Mutat. Res. 398:183-187.
24. Lobanov, A. V., C. Delgado, S. Rahlfs, S. V. Novoselov, G. V. Kryukov, S. Gromer, D. L. Hatfield, K. Becker, and V. N. Gladyshev. 2006. The Plasmodium selenoproteome. Nucleic Acids Res. 34:496-505.
25. Maerki, S., R. Brun, S. A. Charman, A. Dorn, H. Matile, and S. Wittlin. 2006. In vitro assessment of the pharmacodynamic properties and the partitioning of OZ277/RBx-11160 in cultures of Plasmodium falciparum. J. Antimicrob. Chemother. 58:52-58.
26. Mannervik, B., and U. H. Danielson. 1988. Glutathione transferases - structure and catalytic activity. CRC Crit. Rev. Biochem. 23:283-337.
27. Narayanan, B. A., O. Geoffroy, M. C. Willingham, G. G. Re, and D. W. Nixon. 1999. p53/p21(WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells. Cancer Lett. 136:215-221.
28. Nijhoff, W. A., and W. H. Peters. 1994. Quantification of induction of rat oesophageal, gastric and pancreatic glutathione and glutathione S-transferases by dietary anticarcinogens. Carcinogenesis 15:1769-1772.
29. Nordhoff, A., U. S. Bucheler, D. Werner, and R. H. Schirmer. 1993. Folding of the four domains and dimerization are impaired by the Gly446→Glu exchange in human glutathione reductase. Implications for the design of antiparasitic drugs. Biochemistry 32:4060-4066.
30. Perkin, A. G. 1911. Some Oxidation Products of the hydroxybenxoic acids. J. Chem. Soc. 99:1442-1450.
31. Peters, W. 1987. Chemotherapy and drug resistance in malaria, vol. 1. Academic Press, London, United Kingdom.
32. Pfaffl, M. W. 2001. A new mathematical model for relative quantification in real-time RT-PCR. Nucleic Acids Res. 29:e45.
33. Stoner, G. D., and H. Mukhtar. 1995. Polyphenols as cancer chemopreventive agents. J. Cell Biochem. Suppl. 22:169-180.
34. ter Kuile, F., N. J. White, P. Holloway, G. Pasvol, and S. Krishna. 1993. Plasmodium falciparum: in vitro studies of the pharmacodynamic properties of drugs used for the treatment of severe malaria. Exp. Parasitol. 76:85-95.
35. Tilley, L., T. M. Davis, and P. G. Bray. 2006. Prospects for the treatment of drug-resistant malaria parasites. Future Microbiol. 1:127-141.
36. Trager, W., and J. B. Jensen. 1976. Human malaria parasites in continuous culture. Science 193:673-675.
37. Verotta, L., M. Dell'Agli, A. Giolito, M. Guerrini, P. Cabalion, and E. Bosisio. 2001. In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: ellagic acid and 3,4,5-trimethoxyphenyl-(6′-O-galloyl)-O-beta-D-glucopyranoside. J. Nat. Prod. 64:603-607.
38. Zimmermann, H., J. Billard, H. Gutman, E. J. Wachtel, R. Poupko, and Z. Luz. 1992. Thermotropic liquid crystals derived from benzopyranobenzopyran-dione. Preparation and physical properties. Liquid Crystals 12: 245-262.