title: Schistosomicidal and trypanocidal structure-activity relationships for (±)-licarin A and its (-)- and (+)-enantiomers.
abstract: (±)-Licarin A (1) was obtained by oxidative coupling, and its enantiomers, (-)-licarin A (2) and (+)-licarin A (3), were resolved by chiral HPLC. Schistosomicidal and trypanocidal activities of these compounds were evaluated in vitro against Schistosoma mansoni adult worms and trypomastigote forms of Trypanosoma cruzi. The racemic mixture (1) displayed significant schistosomicidal activity with an LC₅₀ value of 53.57 μM and moderate trypanocidal activity with an IC₅₀ value of 127.17 μM. On the other hand, the (-)-enantiomer (2), displaying a LC₅₀ value of 91.71 μM, was more active against S. mansoni than the (+)-enantiomer (3), which did not show activity. For the trypanocidal assay, enantiomer 2 showed more significant activity (IC₅₀ of 23.46 μM) than enantiomer 3, which showed an IC₅₀ value of 87.73 μM. Therefore, these results suggest that (±)-licarin A (1) and (-)-licarin A (2) are promising compounds that could be used for the development of schistosomicidal and trypanocidal agents.
authors.affiliation: Grupo de Pesquisas em Produtos Naturais, Núcleo de Ciências Exatas e Tecnológicas, Universidade de Franca, Avenida Dr. Armando Salles de Oliveira 2001, 14404-600 Franca, SP, Brazil.
authors.forename: A C
authors.initials: AC
authors.lastname: Pereira
authors.forename: L G
authors.initials: LG
authors.lastname: Magalhães
authors.forename: U O
authors.initials: UO
authors.lastname: Gonçalves
authors.forename: P P
authors.initials: PP
authors.lastname: Luz
authors.forename: A C G
authors.initials: AC
authors.lastname: Moraes
authors.forename: V
authors.initials: V
authors.lastname: Rodrigues
authors.forename: P M
authors.initials: PM
authors.lastname: da Matta Guedes
authors.forename: A A
authors.initials: AA
authors.lastname: da Silva Filho
authors.forename: W R
authors.initials: WR
authors.lastname: Cunha
authors.forename: J K
authors.initials: JK
authors.lastname: Bastos
authors.forename: N P D
authors.initials: NP
authors.lastname: Nanayakkara
authors.forename: M L A
authors.initials: ML
authors.lastname: e Silva
mesh_terms: D000818:Animals; D002522:Chlorocebus aethiops; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D005260:Female; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000737:chemistry / Q000494:pharmacology*; D008297:Male; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D058451:Oxidative Coupling; D012550:Schistosoma mansoni / Q000187:drug effects*; D012556:Schistosomicides / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000737:chemistry* / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects*; D014709:Vero Cells
chemical_list: D017705:Lignans; D012556:Schistosomicides; D014344:Trypanocidal Agents; C432503:licarin A