In vivo and in silico anti-inflammatory mechanism of action of the semisynthetic (-)-cubebin derivatives (-)-hinokinin and (-)-O-benzylcubebin

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Lima, Thais C. ; Lucarini, Rodrigo ; Volpe, Angelica C. ; de Andrade, Carolina Q. J. ; Souza, Alice M. P. ; Pauletti, Patricia M. ; Januario, Ana H. ; Simaro, Guilherme V. ; Bastos, Jairo K. ; Cunha, Wilson R. ; Borges, Alexandre ; Laurentiz, Rosangela da Silva ; Conforti, Valeria A. ; Parreira, Renato L. T. ; Borges, Carly H. G. ; Caramori, Giovanni F. ; Andriani, Karla F. ; e Silva, Marcio L. A.

• Tipo de documento: Artigo Científico
• Fonte: Bioorganic & Medicinal Chemistry Letters; v. 27, n. 2, p. 176-179, JAN 15 2017.
• Citações Web of Science: 6

Resumo

(-)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (-)-hinokinin (HK) and (-)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween (R) 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HI( or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2 - cyclooxygenase-2) interaction in comparison with CUB and HK. (C) 2016 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 11/07623-8 - Utilização de métodos mecânicos-quânticos para estudo das ligações e interações químicas em sistemas auto-organizados com aplicação em catálise, química medicinal, eletrocromismo, armazenamento e conversão de energia
• Beneficiário: Renato Luis Tame Parreira
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 05/00494-7 - Obtencao e investigacao do mecanismo analgesico-antiinflamatorio de alguns derivados de (-)- cubeina, isolada de piper cubeba, obtidos por sintese parcial.
• Beneficiário: Thaís Coelho Lima
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica