Antileishmanial activity evaluation of adunchalcone, a new prenylated dihydrochalcone from Piper aduncum L.

Fitoterapia

Volumn 97, Issue , 2014, Pages 28-33

  Dal Picolo, Camilla R ^a   Bezerra, Mariana P ^a   Gomes, Kaio S ^a   Passero, Luiz Felipe D ^b   Laurenti, Marcia D ^b   Martins, Euder Glendes A ^b   Sartorelli, Patricia ^a   Lago, João Henrique G ^a  

^a FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Adunchalcone; Antileishmanial; Dihydrochalcone; Piper aduncum; Piperaceae

Indexed keywords

ADUNCHALCONE; ALCOHOL; AMPHOTERICIN B; ANTILEISHMANIAL AGENT; CHALCONE; DIHYDROCHALCONE; UNCLASSIFIED DRUG; ANTIPARASITIC AGENT; CHALCONE DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE;

AMASTIGOTE; ANIMAL EXPERIMENT; ANTILEISHMANIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY ASSAY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRACTIONATION; HETERONUCLEAR MULTIPLE BOND CORRELATION; LEISHMANIA; LEISHMANIA BRAZILIENSIS; LEISHMANIA CHAGASI; LEISHMANIA SHAWI; LEISHMANIASIS; MOUSE; NONHUMAN; PERITONEUM MACROPHAGE; PIPER (PLANT); PIPER ADUNCUM; PLANT LEAF; PRENYLATION; PRIORITY JOURNAL; PROMASTIGOTE; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; BAGG ALBINO MOUSE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST;

ANIMALS; ANTIPARASITIC AGENTS; CHALCONES; HYDROXYBENZOATES; LEISHMANIA; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; PIPER;

EID: 84902197288     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2014.05.009     Document Type: Article

References (29)

1. B. Liese, M. Rosenberg, and A. Schratz Programmes, partnerships, and governance for elimination and control of neglected tropical diseases Lancet 375 2010 67 76
2. World Health Organization (WHO) Leishmaniasis http://www.who.int/ leishmaniasis/en/ 2013
3. K. Stuart, R. Brun, S.L. Croft, A.H. Fairlamb, R.E. Gürtler, and J. McKerrow et al. Kinetoplastids: related protozoan pathogens, different diseases J Clin Invest 118 2008 1301 1310 (Pubitemid 351500422)
4. S.S. Grecco, J.Q. Reimão, A.G. Tempone, P. Sartorelli, P. Romoff, and M.J.P. Ferreira et al. Isolation of an antileishmanial and antitrypanosomal flavanone from the leaves of Baccharis retusa DC. (Asteraceae) Parasitol Res 106 2010 1245 1248
5. S.L. Croft, S. Sundar, and A.H. Fairlamb Drug resistance in leishmaniasis Clin Microbiol Rev 19 2006 111 126 (Pubitemid 43157649)
6. R.J. Soares-Bezerra, L. Leon, and M. Genestra Recentes avanços da quimioterapia das leishmanioses: moléculas intracelulares como alvo de fármacos Braz J Pharm Sci 40 2004 139 149 (Pubitemid 39128396)
7. E. Rosenthal, and P.J. Marty Recent understanding in the treatment of visceral leishmaniasis Postgrad Med 49 2003 61 68 (Pubitemid 36758270)
8. N. Flores, I.A. Jiménez, A. Giménez, G. Ruiz, D. Gutiérrez, and G. Bourdy et al. Benzoic acid derivatives from Piper species and their antiparasitic activity J Nat Prod 71 2008 1538 1543
9. N. Flores, I.A. Jimenez, A. Gimenez, G. Ruiz, D. Gutierrez, and G. Bourdy et al. Antiparasitic activity of prenylated benzoic acid derivatives from Piper species Phytochemistry 70 2009 621 627
10. P.J.C. Sousa, C.A.L. Barros, J.C.S. Rocha, D.S. Lira, G.M. Monteiro, and J.G.S. Maia Avaliação toxicológica do óleo essencial de Piper aduncum L Braz J Pharmacogn 18 2008 217 221
11. J.H.G. Lago, C.S. Ramos, D.C.C. Casanova, A.A. Morandim, D.C.B. Bergamo, and A.J. Cavalheiro et al. Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum J Nat Prod 67 2004 1783 1788 (Pubitemid 39602351)
12. V.S. Parmar, S.C. Jain, K.S. Bisht, R. Jain, P. Taneja, and A. Jha et al. Phytochemistry of the genus Piper Phytochemistry 46 1997 597 673 (Pubitemid 27483827)
13. A. Hermoso, I.A. Jiménez, Z.A. Mamani, I.L. Bazzocchi, J.E. Piñero, and A.G. Ravelo et al. Antileishmanial activities of dihydrochalcones from Piper elongatum and synthetic related compounds. Structural requirements for activity Bioorg Med Chem 11 2003 3975 3980 (Pubitemid 36970124)
14. B.J. Cabanillas, A. Le-Lamer, D. Castillo, J. Arevalo, Y. Estevez, and R. Rojas et al. Dihydrochalcones and benzoic acid derivatives from Piper dennisii Planta Med 78 2012 914 918
15. H. Lorenzi, and F.J.A. Matos Plantas medicinais do Brasil 2002 Nova Odessa, Instituto Plantarum São Paulo 544
16. F.G. Braga, M.L.M. Bouzada, R.L. Fabrib, M.O. Matosa, F.O. Moreira, and E. Sciob et al. Antileishmanial and antifungal activity of plants used in traditional medicine in Brazil J Ethnopharmacol 111 2007 396 402 (Pubitemid 46546458)
17. E.C. Torres-Santos, D.L. Moreira, M.A.C. Kaplan, M.N. Meirelles, and B. Rossi-Bergmann Selective effect of 2′,6′-dihydroxy-4′- methoxychalcone isolated from Piper aduncum on Leishmania amazonensis Antimicrob Agents Chemother 43 1999 1234 1241 (Pubitemid 29214753)
18. A. Rea, A.G. Tempone, E.G. Pinto, J.T. Mesquita, L.G. Silva, and E. Rodrigues et al. Lago JHG Soulamarin isolated from Calophyllum brasiliense (Clusiaceae) induces plasma membrane permeabilization of Trypanosoma cruzi and mytochondrial dysfunction PLoS Negl Trop Dis 7 2013 e2556
19. E.S. Yamamoto, B.L.S. Campos, M.D. Laurenti, J.H.G. Lago, and L.F.D. Passero Treatment with triterpenic fraction purified from Baccharis uncinella leaves inhibits Leishmania (Leishmania) amazonensis spreading and improves Th1 immune response in infected mice Parasitol Res 113 2014 333 339
20. S.S. Grecco, J.Q. Reimão, A.G. Tempone, P. Sartorelli, R.L.O.R. Cunha, and P. Romoff et al. In vitro antileishmanial and antitrypanosomal activities of flavanones from Baccharis retusa DC. (Asteraceae) Exp Parasitol 130 2012 141 145
21. A.S. Joshi, X.C. Li, A.C. Nimrod, H.N. El-Sohly, L.A. Walker, and A.M. Clark Dihydrochalcones from Piper longicaudatum Planta Med 67 2001 186 188 (Pubitemid 32234693)
22. S.C. Huang, G.C. Yen, L.W. Chang, W.J. Yen, and P.D. Duh Identification of an antioxidant, ethyl protocatechuate, in peanut seed testa J Agric Food Chem 51 2003 2380 2383
23. J. Orjala, C.A. Erdelmeier, A.D. Wright, T. Rali, and O. Sticher Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves Planta Med 59 1993 546 551 (Pubitemid 24019546)
24. S. Franceschelli, M. Pesce, I. Vinciguerra, A. Ferrone, G. Riccioni, and A. Patruno et al. Licocalchone-C extracted from Glycyrrhiza glabra inhibits lipopolysaccharide-Interferon-γ inflammation by improving antioxidant conditions and regulating inducible nitric oxide synthase expression Molecules 16 2011 5720 5734
25. S.F. Nielsen, A. Kharazmi, and S.B. Christensen Modifications of the α, β-double bond in chalcones only marginally affect the antiprotozoal activities Bioorg Med Chem 6 1998 937 945 (Pubitemid 28464523)
26. O. Kayser, and A. Kiderlen In vitro leishmanicidal activity of naturally occurring chalcones Phytother Res 15 2001 148 152
27. S.J. Green, M.S. Meltzer, J.B. Hibbs, and C.A. Nacy Activated macrophages destroy intracellular Leishmania major amastigotes by an l-arginine-dependent killing mechanism J Immunol 144 1990 278 283 (Pubitemid 20030489)
28. F. Poorrajab, S.K. Ardestani, A. Foroumadi, S. Emami, A. Kariminia, and M. Behrouzi-Fardmoghadam et al. Selective leishmanicidal effect of 1,3,4-thiadiazole derivatives and possible mechanism of action against Leishmania species Exp Parasitol 121 2009 323 330
29. L.F.D. Passero, J.V. Sacomori, T.Y. Tomokane, C.E. Corbett, F.T. da Silveira, and M.D. Laurenti Ex vivo and in vivo biological behavior of Leishmania (Viannia) shawi Parasitol Res 105 2009 1741 1747