Antimalarial compounds from traditionally used medicinal plants

Bioactive Natural Products: Detection, Isolation, and Structural Determination, Second Edition

Volumn , Issue , 2007, Pages 491-529

  Mambu, Lengo ^a   Grellier, Philippe ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85028572165     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (150)

1. Snow, R.W., Guerra, C.A., Noor, A.M., Myint, H.Y., and Hay, S.I., The global distribution of clinical episodes of Plasmodium falciparum malaria, Nature, 434, 214, 2005.
2. Ridley, R.G., Medical need, scientific opportunity and the drive for antimalarial drugs, Nature, 415, 686, 2002.
3. Phillipson, J.D. and Wright, C.W., Can ethnopharmacology contribute to the development of antimalarial agents? J. Ethnopharmacol., 32, 155, 1991.
4. Meshnick, S.R. and Dobson, M.J., The history of antimalarials drugs, in Antimalarials Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery, Rosenthal, P.J., Ed., Humana Press, Totowa, NJ, 2001, p. 15.
5. Tilley, L., Loria, P., and Foley, M., Chloroquine and other quinoline antimalarials, in Antimalarials Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery, Rosenthal, P.J., Ed., Humana Press, Totowa, NJ, 2001, p. 87.
6. Meshnick, S.R., Artemisinin and its derivatives, in Antimalarials Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery, Rosenthal, P.J., Ed., Humana Press, Totowa, NJ, 2001, p. 191.
7. Trager, W. and Jensen, J., Human malaria parasites in continuous culture, Science, 193, 673, 1976.
8. Tona, L., Ngimbi, N.P., Tsakala, M., Mesia, K., Cimanga, K., Apers, S., De Bruyne, T., Pieters, L., Totté, J., and Vlietinck, A.J., Antimalarial activity of 20 crude extracts from nine African medicinal plants used in Kinshasa, Congo, J. Ethnopharmacol., 68, 193, 1999.
9. Pink, R., Hudson, A., Mouriès, M.-A., and Bendig, M., Opportunities and challenges in antiparasitic drug discovery, Nat. Rev. Drug Discov., 4, 727, 2005.
10. Frappier, F., Jossang, A., Soudon, J., Calvo, F., Rasoanaivo, P., Rastimamanga-Urveg, S., Saez, J., Schrevel, J., and Grellier, P., Bisbenzylisoquinolines as modulators of chloroquine resistance in Plasmodium falciparum and multidrug resistance in tumor cells, Antimicrob. Agents Chemother., 6, 1476, 1996.
11. Desjardins, R.E., Canfield, C.J., Haynes, J.D., and Chulay, J.D., Quantitative assessment of antimalarial activity by a semi-automated microdilution technique, Antimicrob. Agents Chemother., 16, 710, 1979.
12. Geary, T.G., Divo, A.A., and Jensen, J.B., Effect of calmodulin inhibitors on viability and mitochondrial potential of Plasmodium falciparum in culture, Antimicrob. Agents Chemother., 30, 785, 1986.
13. Elabbadi, N., Ancelin, M.L., and Vial, H.J., Use of radioactive ethanolamine incorporation into phospholipids to assess in vitro antimalarial activity by the semiautomated microdilution technique, Antimicrob. Agents Chemother., 36, 50, 1992.
14. Makler, M.T., Ries, J.M., Williams, J.A., Bancroft, J.E., Piper, R.C., and Gibbins, B.L., Parasite lactate dehydrogenase as an assay for Plasmodium falciparum drug sensitivity, Am. J. Trop. Med. Hyg., 48, 739, 1993.
15. Delhaes, L., Lazaro, J.E., Gay, F., Thellier, M., and Danis, M., The microculture tetrazolium assay (MTA): Another colorimetric method of testing Plasmodium falciparum chemosensitivity, Ann. Trop. Med. Parasitol., 93, 31, 1999.
16. Bennett, T.N., Paguio, M., Gligorijevic, B., Seudieu, C., Kosar, A.D., Davidson, E., and Roepe, P.D., Novel, rapid, and inexpensive cell-based quantification of antimalarial drug efficacy, Antimicrob. Agents Chemother., 48, 1807, 2004.
17. Grellier, P., Valentin, A., Millerioux, V., Schrevel, J., and Rigomier, D., 3-Hydroxy-3-methylglutaryl coenzyme A reductase inhibitors lovastatin and simvastatin inhibit in vitro development of Plasmodium falciparum and Babesia divergens in human erythrocytes, Antimicrob. Agents Chemother., 38, 1144, 1994.
18. Schrevel, J., Sinou, V., Grellier, P., Frappier, F., Guénard, D., and Potier, P., Interactions between docetaxel (Taxotere) and Plasmodium falciparum-infected erythrocytes, Proc. Natl. Acad. Sci., 91, 8472, 1994.
19. Jacquemond-Collet, I., Benoit-Vical, F., Mustofa, Valentin, A., Stanislas, E., Mallié, M., and Fourasté, I., Antiplasmodial and cytotoxic activity of galipinine and other tetrahydroquinolines from Galipea officinalis, Planta Med., 68, 68, 2002.
20. Ringwald, P., Meche, F.S., Bickii, J., and Basco, L.K., In vitro culture and drug sensitivity assay of Plasmodium falciparum with nonserum substitute and acute-phase sera, J. Clin. Microbiol., 37, 700, 1999.
21. The Malaria Research and Reference Reagent Resources Center (MR4), Methods in Malaria Research, www.mr4.org/MR4_Protocols.html (accessed 12 September 2006).
22. Peters, W. and Robinson, B.L., Malaria, in Handbook of Animal Models of Infection, Zak, O. and Sande, M.A., Eds., Academic Press, London, 1999, p. 757.
23. Moreno, A., Badell, E., Van Rooijen, N., and Druilhe, P., Human malaria in immunocompromised mice: New in vivo model for chemotherapy studies, Antimicrob. Agents Chemother., 45, 1847, 2001.
24. Mazier, D., Beaudoin, R.L., Mellouk, S., Druilhe, P., Texier, B., Trosper, J., Miltgen, F., Landau, I., Paul, C., Brandicourt, O., Guguen-Guillouzo, C., and Langlois, P., Complete development of hepatic stages of Plasmodium falciparum in vitro, Science, 227, 440, 1985.
25. Mahmoudi, N., Ciceron, L., Franetich, J.F., Farhati, K., Silvie, O., Eling, W., Sauerwein, R., Danis, M., Mazier, D., and Derouin, F., In vitro activities of 25 quinolones and fluoroquinolones against liver and blood stage Plasmodium spp., Antimicrob. Agents Chemother., 47, 2636, 2003.
26. Mazier, D., Franetich, J.F., Carraz, M., Silvie, O., and Pino, P., Models for studying effects of herbal antimalarials at different stages of the Plasmodium life cycle, in Traditional Medicinal Plants and Malaria, Willcox, M., Bodeker, G., and Rasoanaivo, P., Eds., CRC Press, Boca Raton, 2004, p. 271.
27. Gego, A., Silvie, O., Franetich, J.F., Farhati, K., Hannoun, L., Luty, A.J., Sauerwein, R.W., Boucheix, C., Rubinstein, E., and Mazier, D., New approach for high-throughput screening of drug activity on Plasmodium liver stages, Antimicrob. Agents Chemother., 50, 1586, 2006.
28. http://www.plasmodb.org/plasmo/home.jsp (accessed 12 September 2006).
29. de Koning-Ward, T.F., Janse, C.J., and Waters, A.P., The development of genetic tools for dissecting the biology of malaria parasites, Annu. Rev. Microbiol., 54, 157, 2000.
30. Carvalho, T.G. and Menard, R., Manipulating the Plasmodium genome, Curr. Issues Mol. Biol., 7, 39, 2005.
31. Hall, N., Karras, M., Raine, J.D., Carlton, J.M., Kooij, T.W., Berriman, M., Florens, L., Janssen, C.S., Pain, A., Christophides, G.K., James, K., Rutherford, K., Harris, B., Harris, D., Churcher, C., Quail, M.A., Ormond, D., Doggett, J., Trueman, H.E., Mendoza, J., Bidwell, S.L., Rajandream, M.A., Carucci, D.J., Yates, III J.R., Kafatos, F.C., Janse, C.J., Barrell, B., Turner, C.M., Waters, A.P., and Sinden R.E., A comprehensive survey of the Plasmodium life cycle by genomic, transcriptomic, and proteomic analyses, Science, 30, 82, 2005.
32. Johnson, J.R., Florens, L., Carucci, D.J., and Yates III, J.R., Proteomics in malaria, J. Proteome Res., 3, 296, 2004.
33. Sims, P.F. and Hyde, J.E., Proteomics of the human malaria parasite Plasmodium falciparum, Expert Rev. Proteomics, 3, 87, 2006.
34. Fidock, D.A., Rosenthal, P.J., Croft, S.L., Brun, R., and Nwaka, S., Antimalarial drug discovery: Efficacy models for compound screening, Nat. Rev. Drug. Discov., 3, 509, 2004.
35. Rosenthal, P.J., Antimalarial drug discovery: Old and new approaches, J. Exp. Biol., 206, 3735, 2003.
36. Biagini, G.A., O’Neill, P.M., Nzila, A., Ward, S.A., and Bray, P.G., Antimalarial chemotherapy: Young guns or back to the future? Trends Parasitol., 19, 479, 2003.
37. Rosenthal, P.J., Cysteine proteases of malaria parasites, Int. J. Parasitol., 34, 1489, 2004.
38. Ersmark, K., Samuelsson, B., and Hallberg, A., Plasmepsins as potential targets for new antimalarial therapy, Med. Res. Rev., 26, 626, 2006.
39. Roos, D.S., Crawford, M.J., Donald, R.G., Fraunholz, M., Harb, O.S., He, C.Y., Kissinger, J.C., Shaw, M.K., and Striepen, B., Mining the Plasmodium genome database to define organellar function: What does the apicoplast do? Philos. Trans. R. Soc. Lond. B Biol. Sci., 357, 35, 2002.
40. Wiesner, J. and Seeber, F., The plastid-derived organelle of protozoan human parasites as a target of established and emerging drugs, Expert Opin. Ther. Targets, 9, 23, 2005.
41. Ralph, S.A., D’Ombrain, M.C., and McFadden, G.I., The apicoplast as an antimalarial drug target, Drug Resist. Updat., 4, 145, 2001.
42. Hyde, J.E., Exploring the folate pathway in Plasmodium falciparum, Acta Trop., 94, 191, 2005.
43. Wichmann, O., Muehlberger, N., Jelinek, T., Alifrangis, M., Peyerl-Hoffmann, G., Muhlen, M., Grobusch, M.P., Gascon, J., Matteelli, A., Laferl, H., Bisoffi, Z., Ehrhardt, S., Cuadros, J., Hatz, C., Gjorup, I., McWhinney, P., Beran, J., da Cunha, S., Schulze, M., Kollaritsch, H., Kern, P., Fry, G., and Richter, J., Screening for mutations related to atovaquone/proguanil resistance in treatment failures and other imported isolates of Plasmodium falciparum in Europe, J. Infect. Dis., 190, 1541, 2004.
44. Conners, R., Schambach, F., Read, J., Cameron, A., Sessions, R.B., Vivas, L., Easton, A., Croft, S.L., and Brady, R.L., Mapping the binding site for gossypol-like inhibitors of Plasmodium falciparum lactate dehydrogenase, Mol. Biochem. Parasitol., 142, 137, 2005.
45. Wengelnik, K., Vidal, V., Ancelin, M.L., Cathiard, A.M., Morgat, J.L., Kocken, C.H., Calas, M., Herrera, S., Thomas, A.W., and Vial, H.J., A class of potent antimalarials and their specific accumulation in infected erythrocytes, Science, 295, 1311, 2002.
46. Staines, H.M., Ellory, J.C., and Chibale, K., The new permeability pathways: Targets and selective routes for the development of new antimalarial agents, Comb. Chem. High Throughput Screen, 8, 81, 2005.
47. Doerig, C., Protein kinases as targets for anti-parasitic chemotherapy, Biochim. Biophys. Acta, 1697, 155, 2004.
48. Uzureau, P., Barale, J.C., Janse, C.J., Waters, A.P., and Breton, C.B., Gene targeting demonstrates that the Plasmodium berghei subtilisin PbSUB2 is essential for red cell invasion and reveals spontaneous genetic recombination events, Cell Microbiol., 6, 65, 2004.
49. Buckner, F.S., Eastman, R.T., Yokoyama, K., Gelb, M.H., and Van Voorhis, W.C., Protein farnesyl transferase inhibitors for the treatment of malaria and African trypanosomiasis, Curr. Opin. Invest. Drugs, 6, 791, 2005.
50. Newman, D.J., Cragg, G.M., and Snader, K.M., Natural products as a source of new drugs over the period 1981-2002, J. Nat. Prod., 66, 1002, 2003.
51. Koehn, F.E. and Carter, G.T., The evolving role of natural products in drug discovery, Nat. Rev. Drug Discov., 4, 206, 2005.
52. Soejarto, D.D., Fong, H.H.S., Tan, G.T., Zhang, H.J., Ma, C.Y., Franzblau, S.G., Gyllenhaal, C., Riley, M.C., Kadushin, M.R., Pezzuto, J.M., Xuan, L.T., Hiep, N.T., Hung, N.V., Vu, B.M., Loc, P.K., Dac, L.X., Binh, L.T., Chien, N.Q., Hai, N.V., Bich, T.Q., Cuong, N.M., Southavong, B., Sydara, K., Bouamanivong, S., Ly, H.M., Thuy, T.V., Rose, W.C., and Dietzman, G.R., Ethnobotany/ethnopharmacology and mass bioprospecting: Issues on intellectual property and benefit-sharing, J. Ethnopharmacol., 100, 15, 2005.
53. http://www.biodiv.org/convention/articles.asp (accessed: 12 September 2006).
54. Cragg, G.C. and Newman, D.J., Plants as source of anti-cancer agents, J. Ethnopharmacol., 100, 72, 2005.
55. Bringmann, G., From tropical lianas to novel antiplasmodial agents: The naphthyliso-quinoline alkaloids, in Guidelines and Issues for the Discovery and Drug Development Against Tropical Diseases, Vial, H., Fairlamb, A., and Ridley, R., Eds., World Health Organization, Geneva, 2003, p. 145.
56. Krettli, A.U., Adrade-Neto, V.F., Brandão, M.G.L., and Ferrari, V.M.S., The search for new antimalarial drugs from plants used to treat fever and malaria or randomly selected: A review, Mem. Int. Oswaldo Cruz, 96, 1033, 2001.
57. Adrade-Neto, V.F., Brandão, M.G.L., Stehmann, J.R., Oliveira, L.A., and Krettli, A.U., Antimalarial activity of cinchona-like plants used to treat fever and malaria in Brazil, J. Ethnopharmacol., 87, 253, 2003.
58. Vigneron, M., Deparis, X., Deharo, E., and Bourdy, G., Antimalarial remedies in French Guiana: A knowledge, attitudes and practices study, J. Ethnopharmacol., 98, 351, 2005.
59. Rasoanaivo, P., Deharo, E., Ratshimamanga-Urveg, S., and Frappier, F., Guidelines for the non-clinical evaluation of the efficacy of traditional antimalarials, in Traditional Medicinal Plants and Malaria, Willcox, M., Bodeker, G., and Rasoanaivo, P., Eds., CRC Press, Boca Raton, 2004, p. 255.
60. Bertani, S., Bourdy, G., Landau, I., Robinson, J.C., Esterre, P., and Deharo, E., Evaluation of French Guiana traditional antimalarial remedies, J. Ethnopharmacol., 98, 45, 2005.
61. Zirihi, N.G., Mambu, L., Guédé-Guina, F., Bodo, B., and Grellier, P., In vitro antiplasmodial activity and cytotoxicity of 33 West African plants used for treatment of malaria, J. Ethnopharmacol., 98, 281, 2005.
62. Bringmann, G., Messer, K., Wohlfarth, M., Krauss, J., Dumbuya, K., and Rückert, M., HPLC-CD on-line coupling in combination with HPLC-NMR and HPLC-MS/MS for the determination of the full absolute stereostructure of new metabolites in plant extracts, Anal. Chem., 71, 2678, 1999.
63. Wolfender, J.-L., Queiroz, E.F., and Hostettmann, K., Phytochemistry in the microgram domain-a LC-NMR perspective, Magn. Reson. Chem., 43, 697, 2005.
64. Christensen, S.B. and Kharazmi, A., Antimalarial natural products, in Bioactive Compounds from Natural Sources, Tringali, C., Ed., Taylor and Francis, London, New York, 2001, p. 379.
65. Kayser, O., Kiderlen, A., and Croft, S.L., Natural products as potential antiparasitic drugs, in Studies in Natural Products Chemistry, Volume 26 (Bioactive natural Products), Atta-Ur-Rahman, Ed., 2002, p. 779.
66. Schwikkard, S. and Van Heerden, F.R., Antimalarial activity of plant metabolites, Nat. Prod. Rep., 19, 675, 2002.
67. Caniato, R. and Puricelli, L., Natural antimalarial agents (1995-2001), Crit. Rev. Plant Sci., 22, 79, 2003.
68. Saxena, S., Pant, N., Jain, D.C., and Bhakuni, R.S., Antimalarial agents from plants sources, Curr. Sci., 85, 1314, 2003.
69. Zhang, H.-J., Tamez, P.A., Aydogmus, Z., Tan, G.T., Saikawa, Y., Hashimoto, K., Nakata, M., Hung, N.V., Xuan, L.T., Cuong, N.M., Soejarto, D.D., Pezzuto, J.M., and Fong, H.H.S., Antimalarial agents from plants. III. Trichothecenes from Ficus fistulosa and Rhaphidophora decursiva, Planta Med., 68, 1088, 2002.
70. Singh, A. and Rosenthal, P.J., Comparison of efficacies of cysteine protease inhibitors against five strains of Plasmodium falciparum, Antimicrob. Agents Chemother., 45, 949, 2001.
71. Isaka, M., Punya, J., Lertwerawat, Y., Tanticharoen, M., and Thebtaranonth, Y., Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria, J. Nat. Prod., 62, 329, 1999.
72. Ramanandraibe, V., Martin, M.-T., Rakotondramanana, D., Mambu, L., Ramanitraha-simbola, D., Labaïed, M., Grellier, P., Rasoanaivo, P., and Frappier, F., Pseudoguaianolide sesquiterpene lactones from Vernoniopsis caudata and their antiplasmodial activities, J. Nat. Prod., 68, 800, 2005.
73. Rasoanaivo, P., Ramanitrahasimbola, D., Rafatro, H., Rakotondramanana, D., Robijaona, B., Rakotozafy, A., Ratshimamanga-Urveg, S., Labaïed, M., Grellier, P., Allorge, L., Mambu, L., and Frappier, F., Screening plant extracts of Madagascar for the search of antiplasmodial compounds, Phytother. Res., 18, 742, 2004.
74. Heilmann, J., Wasescha, M.R., and Schmidt T.J., The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells, Bioorg. Med. Chem., 9, 2189, 2001.
75. Clarkson, C., Campbell, W.E., and Smith, P., In vitro antiplasmodial activity of abietane and totarane diterpenoids from Harpagophytum procumbens (Devil’s claw), Planta Med., 69, 720, 2003.
76. Ziegler, H.L., Staerk, D., Christensen, J., Hviid, L., Hägerstrand, H., and Jaroszewski, J.W., In vitro Plasmodium falciparum drug sensitivity assay: Inhibition of parasite growth by incorporation of stomatocytogenic amphiphiles into the erythrocyte membrane, Antimicrob. Agents Chemother., 46, 1441, 2002.
77. Ziegler, H.L., Jensen, T.H., Christensen, J., Staerk, D., Hägerstrand, H., Sittie, A.A., Olsen, C.E., Staalsø, T., Ekpe, P., and Jaroszewski, J.W., Possible artefacts in the in vitro determination of antimalarial activity of natural products that incorporate into lipid bilayer: Apparent antiplasmodial activity of dehydroabietinol, a constituent of Hyptis suaveolens, Planta Med., 68, 547, 2002.
78. Clarkson, C., Musonda, C.C., Chibale, K., Campbell, W.E., and Smith, P., Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity, Bioorg. Med. Chem., 11, 4417, 2003.
79. Loyola, L.A., Bórquez, J., Morales, G., San-Martín, A., Darias, J., Flores, N., and Giménez, A., Mulinane-type diterpenoids from Azorella compacta display antiplasmodial activity, Phytochemistry, 65, 1931, 2004.
80. Linn, T.Z., Awale, S., Tezuka, Y., Banskota, A.H., Kalauni, S.K., Attamimi, F., Ueda, J.-Y., Asih, P.B.S., Syafruddin, D., Tanaka, K., and Kadota, S., Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum, J. Nat. Prod., 68, 706, 2005.
81. Banskota, A.H., Attamimi, F., Linn, T.Z., Usia, T., Tezuka, Y., Kalauni, S.K., and Kadota, S., Novel norcassane-type diterpene from the seed kernels of Caesalpinia crista, Tetrahedron Lett., 44, 6879, 2003.
82. Bringmann, G., Saeb, W., Aké Assi, L., François, G., Narayanan, A.S., Peters, K., and Peters, E-M., Betulinic acid: Isolation from Triphyophyllum peltatum and Ancistrocladus heyneanus, antimalarial activity and crystal structure of the benzyl ester, Planta Med., 63, 255, 1997.
83. Alves, T.M.A., Nagem, T.J., Carvalho, L.H., Krettli, A.U., and Zani, C.L., Antiplasmodial triterpene from Vernonia brasiliana, Planta Med., 63, 554, 1997.
84. Steele, J.C., Warhurst, D.C., Kirby, G.C., and Simmonds, M.S.J., In vitro and in vivo evaluation of betulinic acid as an antimalarial, Phytother. Res., 13, 115, 1999.
85. Suksamrarn, A., Tanachatchairatana, T., and Kanokmedhakul, S., Antiplasmodial triterpenes from twigs of Gardenia saxatilis, J. Ethnopharmacol., 88, 275, 2003.
86. Mambu, L., Grellier, P., Florent, L., Martin, M.-T., Ramanitrahasimbola, D., Rasoanaivo, P., and Frappier, F., Clerodane and labdane diterpenoids from Nuxia sphaerocephala, Phytochemistry, 67, 444, 2006.
87. Ziegler, H.L., Franzyk, H., Sairafianpour, M., Tabatabai, M., Tehrani, M.D., Bagherzadeh, K., Hägerstrand, H., Staerk, D., and Jaroszewski, J.W., Erythrocyte membrane modifying agents and the inhibition of Plasmodium falciparum growth: Structure-activity relationships for betulinic acid analogues, Bioorg. Med. Chem., 12, 119, 2004.
88. Muhammad, I., Bedir, E., Khan, S.I., Tekwani, B.L., Khan, I.A., Takamatsu, S., Pelletier, J., and Walker, L.A., A new antimalarial quassinoid from Simaba orinocensis, J. Nat. Prod., 67, 772, 2004.
89. Chan, K-L., Choo, C-Y., Abdullah, N.R., and Ismail, Z., Antiplasmodial studies of Eurycoma longifolia Jack using the lactate dehydrogenase assay of Plasmodium falciparum, J. Ethnopharmacol., 92, 223, 2004.
90. Chan, K-L., Choo, C-Y., and Abdullah, N.R., Synthetic 15-O-acyl- and 1,15-di-O-acylurycomanones from Eurycoma longifolia as potential antimalarials, Planta Med., 71, 967, 2005.
91. Krief, S., Martin, M.-T., Grellier, P., Kasenene, J., and Sevenet, T., Novel antimalarial compounds isolated in a survey of self-medicative behavior of wild chimpanzees in Uganda, Antimicrob. Agents Chemother., 48, 3196, 2004.
92. Roy, A. and Saraf, S., Limonoids: Overview of significant bioactive triterpenes distributed in plants kingdom, Biol. Pharm. Bull., 29, 191, 2006.
93. Verotta, L., Dell’Agli, M., Giolito, A., Guerrini, M., Cabalion, P., and Bosisio, E., 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)-β-d-glucopyranoside, J. Nat. Prod., 64, 603, 2001.
94. Dell’Agli, M., Parapini, S., Basilico, N., Verotta, L., Taramelli, D., Berry, C., and Bosisio, E., In vitro studies on the mechanism of action of two compounds with antiplasmodial activity: Ellagic acid and 3,4,5-trimethoxyphenyl-(6′-O-galloyl)-β-d-glucopyranoside, Planta Med., 69, 162, 2003.
95. Zhang, H.-J., Tamez, P.A., Hoang, V.D., Tan, G.T., Hung, N.V., Xuan, L.T., Huong, L.M., Cuong, N.M., Thao, D.T., Soejarto, D.D., Fong, H.H.S., and Pezzuto, J.M., Antimalarial compounds from Rhaphidophora decursiva, J. Nat. Prod., 64, 772, 2001.
96. Kraft, C., Jenett-Siems, K., Köhler, I., Tofern-Reblin, B., Siems, K., Bienzle, U., and Eich, E., Antiplasmodial activity of sesquilignans and sesquineolignans from Bonamia spectabilis, Phytochemistry, 60, 167, 2002.
97. Skytte, D.M., Nielsen, S.F., Chen, M., Zhai, L., Olsen, C.E., and Christensen, S.B., Antimalarial and antiplasmodial activities of norneolignans. Syntheses and SAR., J. Med. Chem., 49, 436, 2006.
98. Oketch-Rabah, H.A., Dossaji, S.F., Christensen, S.B., Frydenvang, K., Lemmich, E., Cornett, C., Olsen, C.E., Chen, M., Kharazmi, A., and Theander, T., Antiprotozoal compounds from Asparagus africanus, J. Nat. Prod., 60, 1017, 1997.
99. Kayser, O., Kiderlen, A., Folkens, U., and Kolodziej, H., In vitro leishmanicidal activity of aurones, Planta Med., 65, 316, 1998.
100. Beldjoudi, N., Mambu, L., Labaïed, M., Grellier, P., Rasoanaivo, P., Martin, M.-T., and Frappier, F., Flavonoids from Dalbergia louvelii and their antiplasmodial activity, J. Nat. Prod., 66, 1447, 2003.
101. Yenesew, A., Induli, M., Derese, S., Midiwo, J.O., Heydenreich, M., Peter, M.G., Akala, H., Wangui, J., Liyala, P., and Waters, N.C., Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica, Phytochemistry, 65, 3029, 2004.
102. Kirmizibekmez, H., Calis, I., Perozzo, R., Brun, R., Dönmez, A.A., Linden, A., Rüedi, P., and Tasdemir, D., 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, 2004.
103. Weniger, B., Vonthron-Sénéchau, C., Arango, G.J., Kaiser, M., Brun, R., and Anton, R., A bioactive biflavonoid from Campnosperma panamense, Fitoterapia, 75, 764, 2004.
104. Nunome, S., Ishiyama, A., Kobayashi, M., Otoguro, K., Kiyohara, H., Yamada, H., and Omura, S., In vitro antimalarial activity of biflavonoids from Wikstroemia indica, Planta Med., 70, 76, 2004.
105. Ignatushchenko, M.V., Winter, R.W., Bächinger, H.P., Hinrichs, D.J., and Riscoe, M.K., Xanthones as antimalarial agents: Studies of a possible mode of action, FEBS Lett., 409, 67, 1997.
106. Ignatushchenko, M.V., Winter, R.W., and Riscoe, M.K., Xanthones as antimalarial agents: Stage specificity, Am. J. Trop. Med. Hyg., 62, 77, 2000.
107. Ngouela, S., Lenta, B.N., Noungoue, D.T., Ngoupayo, J., Boyom, F.F., Tsamo, E., Gut, J., Rosenthal, P.J., and Connolly, J.D., Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f., Phytochemistry, 67, 302, 2006.
108. Hay, A.-E., Hélesbeux, J.-J., Duval, O., Labaïd, M., Grellier, P., and Richomme, P., Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii, Life Sci., 75, 3077, 2004.
109. Azebase, A.G., Meyer, M., Valentin, A., Nguemfo, E.L., Fomum, Z.T., and Nkengfack, A.E., Prenylated xanthone derivatives with antiplasmodial activity from Allanblackia monticola Staner L.C., Chem. Pharm. Bull., 54, 111, 2006.
110. Dua, V.K., Ojha, V.P., Roy, R., Joshi, B.C., Valecha, N., Devi, C.U., Bhatnagar, M.C., Sharma, V.P., and Subbarao, S.K., Anti-malarial activity of some xanthones isolated from the roots of Andrographis paniculata, J. Ethnopharmacol., 95, 247, 2004.
111. Wube, A.A., Bucar, F., Asres, K., Gibbons, S., Rattray, L., and Croft, S.L., Antimalarial compounds from Kniphofia foliosa roots, Phytother. Res., 19, 472, 2005.
112. Abegaz, B.M., Bezabih, M., Msuta, T., Brun, R., Menche, D., Mühlbacher, J., and Brigmann, G., Gaboroquinones A and B and 4′-O-demethylknipholone-4′-β-d-glucoside, phenylanthraquinones from the roots of Bulbine frutescens, J. Nat. Prod., 65, 1117, 2002.
113. Onegi, B., Kraft, C., Köhler, I., Freund, M., Jenett-Siems, K., Siems, K., Beyer, G., Melzig, M.F., Bienzle, U., and Eich, E., Antiplasmodial activity of naphthoquinones and one anthraquinone from Stereospermum kunthianum, Phytochemistry, 60, 39, 2002.
114. Kumura, N., Izumi, M., Nakajima, S., Shimizu, S., Kim, H.-S., Wataya, Y., and Baba, N., Synthesis and biological activity of fatty acid derivatives of quinine, Biosci. Biotechnol. Biochem., 69, 2250, 2005.
115. Zirihi, G.N., Grellier, P., Guédé-Guina, F., Bodo, B., and Mambu, L., Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf, Bioorg. Med. Chem. Lett., 15, 2637, 2005.
116. Angerhofer, C.K., Guinaudeau, H., Wongpanich, V., Pezzuto, J.M., and Cordell, G.A., Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids, J. Nat. Prod., 62, 59, 1999.
117. Tshibangu, J.N., Chifundera, K., Kaminsky, R., Wright, A.D., and Köning, G.M., Screening of African medicinal plants for antimicrobial and enzyme inhibitory activity, J. Ethnopharmacol., 80, 25, 2002.
118. Tshibangu, J.N., Chifundera, K., Wright, A.D., and Köning, G.M., HPLC isolation of the antiplasmodially active bisbenzylisoquinone alkaloids present in roots of Cissampelos mucronata, Phytochem. Anal., 14, 13, 2003.
119. Mambu, L., Martin, M.-T., Razafimahefa, D., Ramanitrahasimbola, D., Rasoanaivo, P., and Frappier, F., Spectral characterisation and antiplasmodial activity of bisbenzylisoquinolines from Isolona ghesquiereina, Planta Med., 66, 537, 2000.
120. Lohombo-Ekomba, M.-L., Okusa, P.N., Penge, O., Kabongo, C., Choudhary, M.I., and Kasende, O.E., Antibacterial, antifungal, antiplasmodial, and cytotoxic activities of Albertisia villosa, J. Ethnopharmacol., 93, 331, 2004.
121. Bringmann, G. and Feineis, D., Stress-related polyketide metabolism of Dioncophyllaceae and Ancistrocladaceae, J. Exp. Bot., 52, 2015, 2001.
122. Bringmann, G., Messer, K., Wolf, K., Mühlbacher, J., Grüne, M., Brun, R., and Louis, A.M., Dioncophylline E from Dioncophyllum thollonii, the first 7,3′-coupled dioncophyllaceous naphthylisoquinoline alkaloid, Phytochemistry, 60, 389, 2002.
123. Bringmann, G., Wohlfarth, M., Rischer, H., Schlauer, J., and Brun, R., Extract screening by HPLC coupled to MS-MS, NMR, and CD: A dimeric and three monomeric naphthylisoquinoline alkaloids from Ancistrocladus griffithii, Phytochemistry, 61, 195, 2002.
124. Bringmann, G., Wohlfarth, M., Rischer, H., Heubes, M., Saeb, W., Diem, S., Herderich, M., and Schlauer, J., A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural elucidation of a dimer in crude plant extracts, by the, LC-MS/LC-NMR/LC-CD triad, Anal. Chem., 73, 2571, 2001.
125. Bringmann, G., Messer, K., Schwöbel, B., Brun, R., and Aké Assi, L., Habropetaline A, an antimalarial naphthylisoquinoline alkaloid from Triphyophyllum peltatum, Phytochemistry, 62, 345, 2003.
126. Martin, S.K., Oduola, A.M.J., and Milhous, W.K., Reversal of chloroquine resistance in Plasmodium falciparum by verapamil, Science, 899, 1987.
127. Oduola, A.M., Omitowoju, G.O., Gerena, L., Kyle, D.E., Milhous, W.K., Sowunmi, A., and Salako, L.A., Reversal of mefloquine resistance with penfluridol in isolates of Plasmodium falciparum from South-West Nigeria, Trans. Royal Soc. Trop. Med. Hyg., 87, 81, 1993.
128. Kyle, D.E., Milhous, W.K., and Rossan, R.N., Reversal of Plasmodium falciparum resistance to chloroquine in Panamanian Aotus monkeys, Am. J. Trop. Med. Hyg., 48, 126, 1993.
129. Rasoanaivo, P., Ratsimamanga-Urveg, S., Milijaona, R., Rafatro, H., Rakoto-Ratsimamanga, A., Galeffi, C., and Nicoletti, M., In vitro and in vivo chloroquine-potentiating action of Strychnos myrtoides alkaloids against chloroquine-resistant strains of Plasmodium malaria, Planta Med., 60, 13, 1996.
130. Rafatro, H., Ramanitrahasimbola, D., Rasoanaivo, P., Ratsimamanga-Urveg, S., Rakoto-Ratsimamanga, A., and Frappier, F., Reversal activity of the naturally occurring chemosensitizer malagashanine in Plasmodium malaria, Biochem. Pharmacol., 59, 1053, 2000.
131. Ramanitrahasimbola, D., Rasoanaivo, P., Ratsimamanga-Urveg, S., and Vial, H., Malagashanine potentiates chloroquine antimalarial activity in drug resistant Plasmodium malaria by modifying both its efflux and influx, Mol. Biochem. Parasitol., 146, 58, 2006.
132. Frédérich, M., Hayette, M.-P., Tits, M., De Mol, P., and Angenot, L., Reversal of chloroquine and mefloquine resistance in Plasmodium falciparum by the two monoindole alkaloids, icajine and isoretuline, Planta Med., 67, 523, 2001.
133. Mitaine-Offer, A.-C., Sauvain, M., Valentin, A., Callapa, J., Mallié, M., and Zèches-Hanrot, M., Antiplasmodial activity of Aspidosperma indole alkaloids, Phytomedicine, 9, 142, 2002.
134. Tamez, P.A., Lantvit, D., Lim, E., and Pezzuto, J.M., Chemosensitizing action of cepharanthine against drug-resistant human malaria, Plasmodium falciparum, J. Ethnopharmacol., 98, 137, 2005.
135. Grellier, P., Ramiaramanana, L., Millerioux, V., Deharo, E., Schrével, J., Frappier, F., Trigalo, F., Bodo, B., and Pousset, J.-L., Antimalarial activity of cryptolepine and isocryptolepine, alkaloids isolated from Cryptolepis sanguinolenta, Phytother. Res., 10, 317, 1996.
136. Onyeibor, O., Croft, S.L., Dodson, H.I., Feiz-Haddad, M., Kendrick, H., Millington, N.J., Parapini, S., Phillips, R.M., Seville, S., Shnyder, S.D., Taramelli, D., and Wright, C.W., Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities, and consideration of their antimalarial mode of action, J. Med. Chem., 48, 2701, 2005.
137. Jonckers, T.H., Van Miert, S., Cimanga, K., Bailly, C., Colson, P., De Pauw-Gillet, M.C., Van den Heuvel, H., Claeys, M., Lemiere, F., Esmans, E.L., Rozenski, J., Quirijnen, L., Maes, L., Dommisse, R., Lemiere, G.L., Vlietinck, A.K., and Pieters, L., Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives, J. Med. Chem., 45, 3497, 2002.
138. Philippe, G., Angenot, L., De Mol, P., Goffin, E., Hayette, M.-P., Tits, M., and Frédérich, M., In vitro screening of some Strychnos species for antiplasmodial activity, J. Ethnopharmacol., 97, 535, 2005.
139. Frédérich, M., Jacquier, M.-J., Thépenier, P., De Mol, P., Tits, M., Philippe, G., Delaude, C., Angenot, L., and Zèches-Hanrot, M., Antiplasmodial activity of alkaloids from various Strychnos species, J. Nat. Prod., 65, 1381, 2002.
140. Frédérich, M., Tits, M., Goffin, E., Philippe, G., Grellier, P., De Mol, P., Hayette, M.-P., and Angenot, L., In vitro and in vivo antimalarial properties of isostrychnopentamine, an indolomonoterpenic alkaloid from Strychnos usambarensis, Planta Med., 70, 520, 2004.
141. Muhammad, I., Dunbar, D.C., Khan, S.I., Tekwani, B.L., Bedir, E., Takamatsu, S., Ferreira, D., and Walker, L.A., Antiparasitic alkaloids from Psychotria klugii, J. Nat. Prod., 66, 962, 2003.
142. Ovenden, S.P.B., Cao, S., Leong, C., Flotow, H., Gupta, M.H., Buss, A.D., and Butler, M.S., Spermine alkaloids from Albizia adinocephala with activity against Plasmodium falciparum plasmepsin II, Phytochemistry, 60, 175, 2002.
143. do Céu de Madureira, M., Paula Martins, A., Gomes, M., Paiva, J., Proenca da Cunha, A., and do Rosario, V., Antimalarial activity of medicinal plants used in traditional medicine in S. Tome and Principe islands, J. Ethnopharmacol., 81, 23, 2002.
144. Ratsimamanga-Urveg, S., Rasoanaivo, P., Ramiaramanana, L., Milijaona, R., Rafatro, H., Verdier, F., Rakoto-Ratsimamanga, A., and Lebras, J., In vitro antimalarial activity and chloroquine potentiating action of two bisbenzylisoquinoline enantiomer alkaloids isolated from Strychnopsis thouarsii and Spirospermum penduliflorum, Planta Med., 58, 540, 1992.
145. Mazier, D., Carraz, M., Franetich, J.F., Jossang, A., Joyeau, R., Rasoanaivo, P., and Frappier, F., Alkaloid compounds and their use as antimalarial drugs, International Patent Application N° PCT/EP2005/005239, 21 April 2005.
146. Bourget-Kondracki, M.-L. and Kornprobst, J.-M., Marine pharmacology: Potentialities in the treatment of infectious diseases, osteoporosis and Alzheimer’s disease, Adv. Biochem. Eng. Biotechnol., 97, 105, 2005.
147. Copp, B.R., Kayser, O., Brun, R., and Kiderlen, A.F., Antiparasitic activity of marine pyridoacridone alkaloids related to the ascididemins, Planta Med., 69, 527, 2003.
148. Laurent, D., Jullian, V., Parenty, A., Knibiehler, M., Dorin, D., Schmitt, S., Lozach, O., Lebouvier, N., Frostin, M., Alby, F., Maurel, S., Doerig, C., Meijer, L., and Sauvain, M., Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp., Bioorg. Med. Chem., 14, 4477, 2006.
149. Waller, R.F., Ralph, S.A., Reed, M.B., Su, V., Douglas, J.D., Minnikin, D.E., Cowman, A.F., Besra, G.S., and McFadden, G.I., A type II pathway for fatty acid biosynthesis presents drug targets in Plasmodium falciparum, Antimicrob. Agents Chemother., 47, 297, 2003.
150. Choi, S.J., Parent, R., Guillaume, C., Deregnaucourt, C., Delabre, C., Ojcius, D.M., Montagne, J.J., Celerier, M.L., Phelipot, A., Amiche, M., Molgo, J., Camadro, J.M., and Guette, C., Isolation and characterization of psalmopeotoxin I and II: Two novel antimalarial peptides from the venom of the tarantula Psalmopoeus cambridgei, FEBS Lett., 572, 109, 2004.