(±)-Licarin A and its semi-synthetic derivatives: In vitro and in silico evaluation of trypanocidal and schistosomicidal activities
| Autor: | Lucas Antonio de Lima Paula, Renato L. T. Parreira, Ana Carolina Pereira, N. P. Dhammika Nanayakkara, Vanderlisa Rita Meleti, Renato Pereira Orenha, Rosângela da Silva Laurentiz, Lúzio Gabriel Bocalon Flauzino, Ana Paula da Rocha Pissurno, Lizandra Guidi Magalhães, Wilson Roberto Cunha, Anna Helena Prizantelli, Márcio Luis Andrade e Silva, Jairo Kenupp Bastos, Viviane Rodrigues Esperandim |
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| Přispěvatelé: | Univ Franca, Universidade de São Paulo (USP), Univ Mississippi, Universidade Estadual Paulista (Unesp), IF Suldeminas |
| Rok vydání: | 2020 |
| Předmět: |
0301 basic medicine
Chagas disease Trypanosoma cruzi Veterinary (miscellaneous) 030231 tropical medicine computational study DEPT Horseradish peroxidase Lignans Schistosomicides 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine parasitic diseases medicine Animals Schistosomiasis Chagas Disease Computer Simulation chemistry.chemical_classification biology Chemistry Schistosoma mansoni 030108 mycology & parasitology medicine.disease biology.organism_classification Trypanocidal Agents In vitro (+/-)-Licarin A Isoeugenol Infectious Diseases Enzyme Biochemistry Insect Science biology.protein Parasitology Semi-synthetic derivatives |
| Zdroj: | Web of Science Repositório Institucional da UNESP Universidade Estadual Paulista (UNESP) instacron:UNESP |
| ISSN: | 0001-706X |
| Popis: | Made available in DSpace on 2020-12-10T19:55:41Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-02-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) This paper reports the synthesis of (+/-)-licarin A 1, a dihydrobenzofuran neolignan, resultant of an oxidative coupling reaction of isoeugenol and horseradish peroxidase (HRP) enzyme. Following, three semi-synthetic derivatives from this compound were obtained: benzylated (+/-)-licarin A 2, methylated (+/-)-licarin A 3 and acetylated (+/-)-licarin A 4. After structural elucidation and assignment by Nuclear Magnetic Resonance of H-1, C-13 and DEPT, all compounds were evaluated in vitro against Trypomastigote forms of Trypanosoma cruzi (T. cruzi), the etiologic agent of Chagas disease, and Schistosoma mansoni (S. mansoni) worms, the etiologic agent of schistosomiasis. Compound (4) was the most active against S. mansoni adult worms, displaying worm viability reduction at 25 mu M and mortality of all worms at 100 and 200 mu M within 24 h. Compound 1 was the second most active, showing worm viability reduction at 50 mu M and mortality of 25% and 100% of worms in 24h at concentrations of 100 and 200 mu M, respectively. In addition, theoretical calculations aiming at finding molecular properties that showed the correlation for schistosomicidal and trypanocidal activities of (+/-)-licarin A and three of its semi-synthetic derivatives were also performed. Univ Franca, Nucleo Ciencias Exatas & Tecnol, Grp Pesquisa Produtos Nat, Ave Dr Armando Salles de Oliveira 201, BR-14404600 Franca, SP, Brazil Univ Sao Paulo, Escola Ciencias Farmaceut Ribeirao Preto, Ave Cafe S-N, BR-14040903 Ribeirao Preto, SP, Brazil Univ Mississippi, Sch Pharm, Dept Pharmacognosy, University, MS 38677 USA Univ Mississippi, Sch Pharm, Res Inst Pharmaceut Sci, Natl Ctr Nat Prod Res, University, MS 38677 USA Univ Estadual Paulista, Fac Engn, Dept Fis & Quim, Ilha Solteira, SP, Brazil IF Suldeminas, Ave Maria da Conceicao Santos,900 Parque Real, BR-37550000 Pouso Alegre, MG, Brazil Univ Estadual Paulista, Fac Engn, Dept Fis & Quim, Ilha Solteira, SP, Brazil FAPESP: 1998/14956-7 FAPESP: 2009/05049-2 FAPESP: 2011/07623-8 FAPESP: 2017/24856-2 |
| Databáze: | OpenAIRE |
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