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Molecules 2015, 20(11), 19660-19673; https://doi.org/10.3390/molecules201119649

Comparative Anticonvulsant Study of Epoxycarvone Stereoisomers

1
Instituto de Pesquisa em Fármacos e Medicamentos, Universidade Federal da Paraíba, CP 5009, João Pessoa, CEP 58051-900, PB, Brazil
2
Departamento de Farmácia, Universidade Federal de Sergipe, São Cristóvão-SE, CEP 49100-000, Brazil
3
Departamento de Fisiologia e Patologia, Universidade Federal da Paraíba, CP 5009, João Pessoa, CEP 58051-900, PB, Brazil
4
Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, CP 5009, João Pessoa, CEP 58051-900, PB, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Katalin Prokai-Tatrai
Received: 27 August 2015 / Revised: 12 October 2015 / Accepted: 20 October 2015 / Published: 29 October 2015
(This article belongs to the Section Natural Products Chemistry)
Full-Text   |   PDF [341 KB, uploaded 29 October 2015]   |  

Abstract

Stereoisomers of the monoterpene epoxycarvone (EC), namely (+)-cis-EC, (−)-cis-EC, (+)-trans-EC, and (−)-trans-EC, were comparatively evaluated for anticonvulsant activity in specific methodologies. In the pentylenetetrazole (PTZ)-induced anticonvulsant test, all of the stereoisomers (at 300 mg/kg) increased the latency to seizure onset, and afforded 100% protection against the death of the animals. In the maximal electroshock-induced seizures (MES) test, prevention of tonic seizures was also verified for all of the isomers tested. However, the isomeric forms (+) and (−)-trans-EC showed 25% and 12.5% inhibition of convulsions, respectively. In the pilocarpine-induced seizures test, all stereoisomers demonstrated an anticonvulsant profile, yet the stereoisomers (+) and (−)-trans-EC (at 300 mg/kg) showed a more pronounced effect. A strychnine-induced anticonvulsant test was performed, and none of the stereoisomers significantly increased the latency to onset of convulsions; the stereoisomers probably do not act in this pathway. However, the stereoisomers (+)-cis-EC and (+)-trans-EC greatly increased the latency to death of the animals, thus presenting some protection. The four EC stereoisomers show promise for anticonvulsant activity, an effect emphasized in the isomers (+)-cis-EC, (+)-trans-EC, and (−)-trans-EC for certain parameters of the tested methodologies. These results serve as support for further research and development of antiepileptic drugs from monoterpenes. View Full-Text
Keywords: anticonvulsant; carvone; stereoisomers; terpene; natural products; essential oils; pentylenetetrazole; seizures; para-menthanes; enantiomers anticonvulsant; carvone; stereoisomers; terpene; natural products; essential oils; pentylenetetrazole; seizures; para-menthanes; enantiomers
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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MDPI and ACS Style

Salgado, P.R.R.; Da Fonsêca, D.V.; Braga, R.M.; De Melo, C.G.F.; Andrade, L.N.; De Almeida, R.N.; De Sousa, D.P. Comparative Anticonvulsant Study of Epoxycarvone Stereoisomers. Molecules 2015, 20, 19660-19673.

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