Furofuran lignans display schistosomicidal and trypanocidal activities

• Published in: Phytochemistry (Oxford) 2014-11, Vol.107, p.119-125
• Main Authors: e Silva, Márcio Luis Andrade, Esperandim, Viviane Rodrigues, Ferreira, Daniele da Silva, Magalhães, Lizandra Guidi, Lima, Thais Coelho, Cunha, Wilson Roberto, Nanayakkara, Dhammika N.P., Pereira, Ana Carolina, Bastos, Jairo Kenupp
• Format: Article
• Language: English
• Subjects: Animals; Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis; Bridged Bicyclo Compounds, Heterocyclic - chemistry; Furans - chemical synthesis; Furans - chemistry; Furans - pharmacology; Furofuran lignan; Humans; Inhibitory Concentration 50; Lactones - chemical synthesis; Lactones - chemistry; Leishmania - drug effects; Leishmania amazonensis; Leishmania mexicana - drug effects; Lignans - chemical synthesis; Lignans - chemistry; Lignans - pharmacology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Parasitic Sensitivity Tests; Schistosoma mansoni; Schistosoma mansoni - drug effects; Schistosomicidal activity; Schistosomicides - chemical synthesis; Schistosomicides - chemistry; Schistosomicides - pharmacology; Trypanocidal activity; Trypanocidal Agents - chemical synthesis; Trypanocidal Agents - chemistry; Trypanocidal Agents - pharmacology; Trypanosoma cruzi; Trypanosoma cruzi - drug effects
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2014.08.010

This paper describes schistosomicidal, trypanocidal, and leishmanicidal activities of dehydrodiferulic acid dilactone 1 and dehydrodisinapic acid dilactone 2. Antiparasitic activities were evaluated in vitro against Schistosoma mansoni adult worms, trypomastigote and amastigotes forms of Trypanosoma cruzi, and promastigote forms of Leishmania amazonensis. •Two furofuran lignans were obtained by oxidative coupling.•Schistosomicidal, trypanocidal, and leishmanicidal activities were evaluated.•Dehydrodiferulic dilactone display potent trypanocidal activity.•Dehydrodisinapic dilactone had trypanocidal and schistosomicidal activities.•Furofuran lignans are potentially useful for antiparasitic drugs development. Parasitic diseases continue to be a major worldwide health problem, and there is an urgent need for development of therapeutic drugs. This paper describes synthesis of dehydrodiferulic acid dilactone 1 and dehydrodisinapic acid dilactone 2 furofuran lignans by oxidative coupling of ferulic and sinapic acids, respectively. Their schistosomicidal, trypanocidal, and leishmanicidal activities were evaluated in vitro against Schistosoma mansoni adult worms, trypomastigote and amastigotes forms of Trypanosoma cruzi, and promastigote forms of Leishmania amazonensis. Compound 1 did not display significant schistosomicidal activity, but it presented potent trypanocidal activity, since it induced death of trypomastigotes and amastigotes with IC50/24h of 9.3μM and 7.3μM, respectively. Compound 2 had slight trypanocidal and schistosomicidal activities. None of the compounds were active against L. amazonensis. These results demonstrated that furofuran lignans are potentially useful for anti-parasitic drugs development and should be further investigated.