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. 2015 Oct 29;20(11):19660-73.
doi: 10.3390/molecules201119649.

Comparative Anticonvulsant Study of Epoxycarvone Stereoisomers

Paula Regina Rodrigues Salgado  1 , Diogo Vilar da Fonsêca  2 , Renan Marinho Braga  3 , Cynthia Germoglio Farias de Melo  4 , Luciana Nalone Andrade  5 , Reinaldo Nóbrega de Almeida  6   7 , Damião Pergentino de Sousa  8   9
Affiliations

Comparative Anticonvulsant Study of Epoxycarvone Stereoisomers

Paula Regina Rodrigues Salgado et al. Molecules. .

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.

Keywords: anticonvulsant; carvone; enantiomers; essential oils; natural products; para-menthanes; pentylenetetrazole; seizures; stereoisomers; terpene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Preparation of epoxycarvone stereoisomers. Reagents and Conditions: a. H2O2 30%, KOH, MeOH, 4 h, 0 °C; b. NaBH4, CeCl3.7 H2O, MeOH, 5 min., 20 °C; c. m-CPBA in CH2Cl2, 6 h, 0 °C; d. PCC, Pyr, 30 h, r.t.
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References

    1. Fisher R.S., Acevedo C., Arzimanoglou A., Bogacz A., Cross H., Elger C.E., Engel J., Jr., Forsgren L., French J.A., Glynn M., et al. A practical clinical definition of epilepsy. Epilepsia. 2014;55:475–482. doi: 10.1111/epi.12550. - DOI - PubMed
    1. Engel J. Concepts of epilepsy. Epilepsia. 1995;36:23–30. doi: 10.1111/j.1528-1157.1995.tb01648.x. - DOI - PubMed
    1. Kwan P., Brodie M.J. Refractory epilepsy: Mechanisms and solutions. Expert Rev. Neurother. 2006;6:397–406. doi: 10.1586/14737175.6.3.397. - DOI - PubMed
    1. Motamedi G., Meador K. Epilepsy and cognition. Epilepsy Behav. 2003;4:25–38. doi: 10.1016/j.yebeh.2003.07.004. - DOI - PubMed
    1. Fortini S., Corredera L., Pastrana A.L., Reyes G., Fasulo L., Caraballo R.H. Encephalopathy with hemi-status epilepticus during sleep or hemi-continuous spikes and waves during slow sleep syndrome: A study of 21 patients. Seizure. 2013;22:565–571. doi: 10.1016/j.seizure.2013.04.006. - DOI - PubMed

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