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Planta Med 2013; 79(8): 628-633
DOI: 10.1055/s-0032-1328402
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Evaluation and Theoretical Study on the Anti-inflammatory Mechanism of 1-Nitro-2-phenylethane

Joyce K. L. Vale
1   Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil
,
Anderson B. Lima
1   Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil
,
Bruno G. Pinheiro
1   Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil
,
Alessandra S. Cardoso
2   Faculdade de Farmácia, Universidade Federal do Pará, Belém, PA, Brasil
,
Joyce K. R. Silva
3   Faculdade de Engenharia Química, Universidade Federal do Pará, Belém, PA, Brasil
,
José G. S. Maia
3   Faculdade de Engenharia Química, Universidade Federal do Pará, Belém, PA, Brasil
,
Gloria E. P. de Sousa
4   Faculdade de Ciências Farmacêutica de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brasil
,
Albérico B. F. da Silva
5   Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brasil
,
Pergentino J. C. Sousa
1   Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil
,
Rosivaldo S. Borges
1   Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil
5   Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brasil
› Author Affiliations
Further Information

Publication History

received 29 May 2012

accepted 04 March 2013

Publication Date:
13 May 2013 (online)

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Abstract

In this study, 1-nitro-2-phenylethane was evaluated with respect to its effects in edema models of acute inflammation induced with carrageenan, dextran, and croton oil. 1-Nitro-2-phenylethane produced inhibition of rat paw edema induced by carrageenan and dextran at the doses of 25 and 50 mg/kg. The same doses caused an inhibition of croton oil-induced ear edema in mice. Our results suggest that 1-nitro-2-phenylethane has anti-inflammatory activity, probably of peripheral origin, acting in the synthesis and/or release of inflammatory mediators. A conformational study of 1-nitro-2-phenylethane was carried out using density functional theory calculations, showing three different groups of conformers corresponding to energy minimum geometries. The stereoelectronic repulsions are responsible for conformational preferences and the one most stable conformer. The prostaglandin endoperoxide synthase mechanism is related more to electrophilic than nucleophilic properties.

Key words

anti-inflammatory - Lauraceae - Aniba canelilla - DFT - 1-nitro-2-phenylethane - SAR
 

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