Trypanocidal activity of triterpenes from Arrabidaea triplinervia and derivatives.
Ethanol extract from Arrabidaea triplinervia leaves showed in vitro activity (ED100 5.0 mg/ml) against trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas; disease. Bioactivity-directed fractionation of this extract led to the isolation of ursolic and oleanolic acids as trypanocidal compounds besides pomolic acid (not tested) and alpinetine (inactive). A series of natural and synthetic derivatives of ursolic and oleanolic acids was simultaneously assayed for structure activity relationships (SAR) studies. Ursolic acid (ED100 0.4 mg/ml) was four times more active than oleanolic acid (ED100 1.6 mg/ml). The presence of free hydroxy and/or carboxy groups is necessary for the trypanocidal activity as could be deduced from the effect of the acetates, methyl ester, and aldehyde derivatives.
Leite
João Paulo V
JP
Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, UFMG, Brazil.
Oliveira
Alaíde B
AB
Lombardi
Júlio A
JA
Filho
José Dias S
JD
Chiari
Egler
E
D000818:Animals; D029402:Bignoniaceae / Q000737:chemistry*; D014355:Chagas Disease / Q000097:blood / Q000469:parasitology / Q000517:prevention & control; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000187:drug effects / Q000469:parasitology; D013058:Mass Spectrometry / Q000379:methods; D051379:Mice; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D021261:Parasitic Sensitivity Tests / Q000379:methods; D008517:Phytotherapy / Q000379:methods; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects / Q000254:growth & development; D000097245:Ursolic Acid
D009828:Oleanolic Acid; D010936:Plant Extracts; D014315:Triterpenes; D014344:Trypanocidal Agents; D000097245:Ursolic Acid