Chemical composition of aspidosperma ulei markgr. and antiplasmodial activity of selected indole alkaloids

Molecules

Volumn 18, Issue 6, 2013, Pages 6281-6297

  Dos Santos Torres, Zelina Estevam ^a,b   Silveira, Edilberto Rocha ^b   Rocha E Silva, Luiz Francisco ^a,c   Lima, Emerson Silva ^c   De Vasconcellos, Marne Carvalho ^c   De Andrade Uchoa, Daniel Esdras ^b   Filho, Raimundo Braz ^d   Pohlit, Adrian Martin ^a  

^a INSTITUTO NACIONAL DE PESQUISAS DA AMAZÔNIA   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c FEDERAL UNIVERSITY OF AMAZONAS   (Brazil)

^d UNIVERSIDADE ESTADUAL DO NORTE FLUMINENSE DARCY RIBEIRO   (Brazil)

Author keywords

Antiplasmodial; Apocynaceae; Aspidosperma ulei; Cytotoxic evaluation; Dasycarpane; Indole alkaloids; Murine fibroblasts; NMR; Plasmodium falciparum K1

Indexed keywords

ANTIMALARIAL AGENT; INDOLE ALKALOID; PLANT EXTRACT;

3T3 CELL LINE; ANIMAL; ASPIDOSPERMA; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SENSITIVITY; IC50; ISOLATION AND PURIFICATION; MOUSE; PLASMODIUM FALCIPARUM; TOXICITY; ARTICLE; CELL STRAIN 3T3; DRUG EFFECT; IC 50;

ANIMALS; ANTIMALARIALS; ASPIDOSPERMA; INDOLE ALKALOIDS; INHIBITORY CONCENTRATION 50; MICE; MOLECULAR STRUCTURE; NIH 3T3 CELLS; PARASITIC SENSITIVITY TESTS; PLANT EXTRACTS; PLASMODIUM FALCIPARUM;

EID: 84879678652     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18066281     Document Type: Article

References (43)

1. World Malaria Report; World Health Organization: Geneva, Switzerland, 2011.
2. Willcox, M.L.; Bodeker, G. Clinical Review. Traditional herbal medicines for malaria. Med. J. 2004, 329, 1156-1159.
3. Milliken, W. Plants for Malaria. Plants for Fever; The Royal Botanic Gardens: Kew, UK, 1997.
4. Dolabela, M.F.; Oliveira, S.G.; Peres, J.M.; Nascimento, J.M.S.; Póvoa, M.M.; Oliveira, A.B. In vitro antimalarial activity of six Aspidosperma species from the state of Minas Gerais (Brazil). An. Acad. Bras. Ciên. 2012, 84, 899-910.
5. Pereira, M.M.; Jácome, L.R.P.; Alcântara, A.F.C.; Alves, R.B.; Raslan, D.S. Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae). Quím. Nova 2007, 30, 970-983.
6. Oliveira, V.B.; Freitas, M.S.M.; Mathias, L.; Braz-Filho, R.; Vieira, I.J.C. Atividade biológica e alcalóides indólicos do gênero Aspidosperma (Apocynaceae): uma revisão. Rev. Bras. Plantas Med. 2009, 11, 92-99.
7. Henrique, M.C.; Nunomura, S.M.; Pohlit, A.M. Alcalóides indólicos das cascas de Aspidosperma vargasii e A. desmanthum. Quím. Nova 2010, 33, 2284-2287.
8. Büchi, G.; Warnhoff, E.W. The structure of uleine. J. Am. Chem. Soc. 1959, 81, 4433-4434.
9. Büchi, G.; Gould, S.J.; NäF, F. Stereospecific syntheses of uleine and epiuleine. J. Am. Chem. Soc. 1971, 93, 2492-2501.
10. Mitaine-Offer, A.C.; Sauvain, M.; Valentin, A.; Callapa, J.; Mallié, M.; Zèches-Hanrot, M. Antiplasmodial activity of Aspidosperma indole alkaloids. Phytomedicine 2002, 9,142-145.
11. Dominique, M.; Roland, M. Use of uleine for the prevention and/or the treatment of infectious diseases. PCT Int. Appl. WO 2011160684 A1 20111229, 2011.
12. Oliveira, A.B. Standardized extracts and fractions of husks of Aspidosperma parvifolium and/or ulein for pharmaceutical use. Brazilian Patent PI BR 20095584 A2 20110823, 2011.
13. Oliveira, A.B.; Dolabela, M.; Póvoa, M.; Santos, C.A.M.; Varotti, F.P. Antimalarial activity of ulein and proof of its action on the Plasmodium falciparum digestive vacuole. Malaria J. 2010, 9, Oral Presentation O9.
14. Andrade-Neto, V.F.; Pohlit, A.M.; Pinto, A.C.; Silva, E.C.; Nogueira, K.L.; Melo, M.R.; Henrique, M.C.; Amorim, R.C.; Silva, L.F.; Costa, M.R.; et al. In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants. Mem. Inst. Oswaldo Cruz 2007, 102, 359-365.
15. Rocha e Silva, L.F.; Montoia, A.; Amorim, R.C.N.; Melo, M.R.; Henrique, M.C.; Nunomura, S.M.; Costa, M.R.F.; Andrade Neto, V.F.; Costa, D.S.; Dantas, G.; et al. Comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog. Phytomedicine 2012, 20, 71-76.
16. Uchoa, D.E.A. Aplicação de técnicas contemporâneas de ressonância magnética nuclear no estudo fitoquímico de Aspidosperma ulei Markgf. Ph.D. Thesis, Universidade Federal do Ceará, Fortaleza, Brazil, 2006.
17. Ondetti, M.A.; Deulofeu, V. Alkaloids from Aspidosperma australe Mull Argov. Relationship of olivacine to u-alkaloid C. The structure of olivacine and u-alkaloid C (guatambuine). Tetrahedron Lett. 1959, 7, 1-4.
18. Seebacher, W.; Simic, N.; Weis, R.; Saf, R.; Kunert, O. Spectral assignments and reference data. Magn. Reson. Chem. 2003, 41, 636-638.
19. Lemes, G.F.; Ferri, P.H.; Lopes, M.N. Constituintes químicos de Hyptidendron canun (Pohl ex Benth.) R. Harley (Lamiaceae). Quím. Nova 2011, 34, 39-42.
20. Endringer, D.C.; Pezzuto, J.M.; Soares, C.M.; Braga, F.C. L-(+)-Bornesitol. Acta Crystallogr. Sect. E 2007, 63, 1067-1068.
21. Waschsmuth, R; Matusch, R. Anhydronium bases from Rauvolfia serpentina. Phytomedicine 2002, 61, 705-709.
22. 13C nuclear magnetic resonance spectral analysis. J. Am. Chem. Soc. 1976, 98, 3645-3655.
23. Passemar, C.; Saléry, M.; Soh, P.N.; Linas, M.-D.; Ahond, A.; Poupat, C.; Benoit-Vical, F. Indole and aminoimidazole moieties appear as key structural units in antiplasmodial molecules. Phytomedicine 2011, 18, 1118-1125.
24. Hu, Y.; Coates, A.R.M. Novel combination for treatment of microbial infections. Patent PCT Int. Appl. WO 2012032360 CA 2809203, 2012.
25. Pascale, C.; Richard, B.; Deverre, J.R.; Sevenet, T.; Zeches, M.; Le Men-Oliver, L. Alkaloids from leaves and root bark of Ervatamia hirta. Phytomedicine 1991, 30, 3785-3792.
26. Bartlett, M.F.; Korzun, B.; Sklar, R.; Smith, A.F.; Taylor, W.I. The alkaloids of Hunteria eburnea Pichon. II: The quaternary bases. J. Org. Chem. 1963, 28, 1445-1449.
27. Burnell, R.H.; Chapelle, A.; Khalil, M.F. Hunteracine: The crystal structure of a quaternary alkaloid from Hunteria eburnea Pichon. J. Chem. Soc. Chem. Comm. 1970, 12, 722-723.
28. Burnell, R.H.; Chapelle, A.; Khalil, M.F. Quaternary bases from Hunteria eburnea Pichon. Can. J. Chem. 1974, 52, 2327-2330.
29. Marini-Bettolo, G.B.; Nicoletti, M.; Messana, I.; Patamia, M.; Galeffi, C.; Oguakwa, J.U.; Portalone, G.; Vaciago, A. Research on Africa medicinal plants-IV: Boonein, a new C-9 terpenoid lactone from Alstonia boonei: A possible precursor in the indole alkaloid biogenesis. Tetrahedron 1983, 39, 323-329.
30. Borris, R.P.; Larris, D.C.; Cordell, G.A. Studies on the uleine alkaloids I. Carbon-13-NMR studies on uleine, 20-epiuleine and (4S)-uleine-Nb-oxide. J. Nat. Prod. 1983, 46, 200-205.
31. Jácome, R.L.R.P.; Oliveira, A.B.; Raslan, D.S.; Wagner, H. Estudo químico e perfil cromatográfico de Aspidosperma parvifolium A. DC. ("pau-pereira"). Quím. Nova 2004, 27, 897-900.
32. Amat, M.; Pérez, M.; Llor, N.; Escolano, C.; Luque, F.J.; Molins, E.; Bosch, J. Conjugate additions to phenylglycinol-derived unsaturated δ-lactams enantioselective synthesis of uleine alkaloids. J. Org. Chem. 2004, 69, 8681-8693.
33. Forns, P.; Diez, A.; Rubiralta, M. Synthetic applications of 2-(1,3-dithian-2-yl) indoles VI. Synthesis of 20-epidasycarpidone. Tetrahedron 1996, 52, 3564-3574.
34. Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. Total synthesis of uleine-type and Strychnos alkaloids through a common intermediate. J. Org. Chem. 1994, 59, 3939-3951.
35. Figueiredo, E.R.; Vieira, I.J.C.; Souza, J.J.; Braz-Filho, R.; Mathias, L.; Kanashiro, M.M.; Côrtes, F.H. Isolamento, identificação e avaliação da atividade antileucêmica de alcalóides indólicos monoterpênicos de Tabernaemontana salzmannii (A. DC.), Apocynaceae. Rev. Bras. Farmacogn. 2010, 20, 675-681.
36. Kobayashi, J.; Sekiguchi, M.; Shimamoto, S.; Shigemori, H.; Ishiyama, H.; Ohsaki, A. Subicanadines A-C, novel quaternary índole alkaloids from Aspidosperma subincanum. J. Org. Chem. 2002, 67, 6449-6455.
37. Amat, M.; Coll, M.-D.; Passarella, D.; Bosch, J. An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline. Tetrahedron-Asymmetry 1996, 7, 2775-2778.
38. Amat, M.; Coll, M.D.; Bosch, J.; Espinosa, E.; Molins, E. Total synthesis of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine and (-)-19,20-dihydroakuammicine. Tetrahedron-Asymmetr. 1997, 8, 935-948.
39. Milborrow, B.V.; Djerassi, C. Alkaloids studies: Part LXI: The structure of twelve new alkaloids from Aspidosperma cylindrocarpon. J. Chem. Soc. C 1969, 417-424.
40. 13C-NMR data of the simplest plumeran indole alkaloids isolated from Aspidosperma species. Molecules 2012, 17, 3025-3043.
41. Trager, W.; Jensen, J.B. Human malaria parasites in continuous culture. Science 1976, 193, 673-675.
42. Rocha e Silva, L.F.; Lima, E.S.; Vasconcellos, M.C.; Aranha, E.S.P.; Costa, D.S.; Santos, E.V.M.; Silva, T.C.M.; Morais, S.K.R.; Quignard, E.L.J.; Alecrim, M.G.C.; et al. In vitro and in vivo antimalarial activity and cytotoxicity of extracts, fractions and a substance isolated from the Amazonian plant Tachia grandiflora (Gentianaceae). Mem. Inst. Oswaldo Cruz 2013, 108, in press.
43. Ahmed, S.A.; Gogal, R.M., Jr.; Walsh, J.E. A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: An alternative to [3H] thymidine incorporation assay. J. Immunol. Meth. 1994, 15, 15211-15224.