Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study.
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFCG |
Texto Completo: | http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244 |
Resumo: | Many terpenes are used therapeutically, and as flavor and fragrance materials. (R)-()-Carvone, the main constituent of spearmint oil, and (S)-(þ)-carvone, found as major component of caraway and dill seed oils, have several applications and are used in cosmetic, food, and pharmaceutical preparations. In this study, the effect of enantiomers of carvone on the central nervous system (CNS) was evaluated in mice. The LD50 value was 484.2 mg/kg (358.9–653.2) for (S)-(þ)-carvone, and 426.6 (389.0–478.6) mg/kg for (R)-()-carvone. Both enantiomers caused depressant effects, such as decrease in the response to the touch and ambulation, increase in sedation, palpebral ptosis, and antinociceptive effects. (S)-(þ)- and (R)-()-carvone caused a significant decrease in ambulation. (R)-()-Carvone appeared to be more effective than its corre-sponding enantiomer at 0.5 and 2.0 h after administration. However, (S)-(þ)-carvone was slightly more potent at 1 h. In potentiating pentobarbital sleeping time, (R)-()-car-vone was more effective than (S)-(þ)-carvone at 100 mg/kg, but was less potent at 200 mg/kg compared to the (þ)-enantiomer, indicating a sedative action. (S)-(þ)-Carvone at the dose of 200 mg/kg increased significantly the latency of convulsions induced by PTZ and PIC, but (R)-()-carvone was not effective against these convulsions. These results suggest that (S)-(þ)-carvone and (R)-()-carvone have depressant effect in the CNS. (S)-(þ)-Carvone appears to have anticonvulsant-like activity. Chirality 19:264–268, 2007. |
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Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study.Influência da quiralidade de (R)-(-)- e (S)-(+)-carvona no sistema nervoso central: Um estudo comparativo.Anticonvulsant activitySedative effectSpearmintCarawayp-menthaneEssential oilsMonoterpeneStructure–activity relationshipAtividade anticonvulsivanteEfeito sedativoHortelãAlcaraviap-mentanoÓleos essenciaisMonoterpenoRelação estrutura-atividadeFarmácia.Química.Many terpenes are used therapeutically, and as flavor and fragrance materials. (R)-()-Carvone, the main constituent of spearmint oil, and (S)-(þ)-carvone, found as major component of caraway and dill seed oils, have several applications and are used in cosmetic, food, and pharmaceutical preparations. In this study, the effect of enantiomers of carvone on the central nervous system (CNS) was evaluated in mice. The LD50 value was 484.2 mg/kg (358.9–653.2) for (S)-(þ)-carvone, and 426.6 (389.0–478.6) mg/kg for (R)-()-carvone. Both enantiomers caused depressant effects, such as decrease in the response to the touch and ambulation, increase in sedation, palpebral ptosis, and antinociceptive effects. (S)-(þ)- and (R)-()-carvone caused a significant decrease in ambulation. (R)-()-Carvone appeared to be more effective than its corre-sponding enantiomer at 0.5 and 2.0 h after administration. However, (S)-(þ)-carvone was slightly more potent at 1 h. In potentiating pentobarbital sleeping time, (R)-()-car-vone was more effective than (S)-(þ)-carvone at 100 mg/kg, but was less potent at 200 mg/kg compared to the (þ)-enantiomer, indicating a sedative action. (S)-(þ)-Carvone at the dose of 200 mg/kg increased significantly the latency of convulsions induced by PTZ and PIC, but (R)-()-carvone was not effective against these convulsions. These results suggest that (S)-(þ)-carvone and (R)-()-carvone have depressant effect in the CNS. (S)-(þ)-Carvone appears to have anticonvulsant-like activity. Chirality 19:264–268, 2007.Universidade Federal de Campina GrandeBrasilUFCG20072024-08-09T18:05:17Z2024-08-092024-08-09T18:05:17Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nobrega de. Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. Chirality (New York) , v. 19, p. 264-268, 2007. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244engSOUSA, Damião Pergentino de.NÓBREGA, Franklin Ferreira de Farias.ALMEIDA, Reinaldo Nobrega de.info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFCGinstname:Universidade Federal de Campina Grande (UFCG)instacron:UFCG2024-08-09T18:07:04Zoai:localhost:riufcg/37244Biblioteca Digital de Teses e Dissertaçõeshttp://bdtd.ufcg.edu.br/PUBhttp://dspace.sti.ufcg.edu.br:8080/oai/requestbdtd@setor.ufcg.edu.br || bdtd@setor.ufcg.edu.bropendoar:48512024-08-09T18:07:04Biblioteca Digital de Teses e Dissertações da UFCG - Universidade Federal de Campina Grande (UFCG)false |
dc.title.none.fl_str_mv |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. Influência da quiralidade de (R)-(-)- e (S)-(+)-carvona no sistema nervoso central: Um estudo comparativo. |
title |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
spellingShingle |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. SOUSA, Damião Pergentino de. Anticonvulsant activity Sedative effect Spearmint Caraway p-menthane Essential oils Monoterpene Structure–activity relationship Atividade anticonvulsivante Efeito sedativo Hortelã Alcaravia p-mentano Óleos essenciais Monoterpeno Relação estrutura-atividade Farmácia. Química. |
title_short |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
title_full |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
title_fullStr |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
title_full_unstemmed |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
title_sort |
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. |
author |
SOUSA, Damião Pergentino de. |
author_facet |
SOUSA, Damião Pergentino de. NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nobrega de. |
author_role |
author |
author2 |
NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nobrega de. |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
SOUSA, Damião Pergentino de. NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nobrega de. |
dc.subject.por.fl_str_mv |
Anticonvulsant activity Sedative effect Spearmint Caraway p-menthane Essential oils Monoterpene Structure–activity relationship Atividade anticonvulsivante Efeito sedativo Hortelã Alcaravia p-mentano Óleos essenciais Monoterpeno Relação estrutura-atividade Farmácia. Química. |
topic |
Anticonvulsant activity Sedative effect Spearmint Caraway p-menthane Essential oils Monoterpene Structure–activity relationship Atividade anticonvulsivante Efeito sedativo Hortelã Alcaravia p-mentano Óleos essenciais Monoterpeno Relação estrutura-atividade Farmácia. Química. |
description |
Many terpenes are used therapeutically, and as flavor and fragrance materials. (R)-()-Carvone, the main constituent of spearmint oil, and (S)-(þ)-carvone, found as major component of caraway and dill seed oils, have several applications and are used in cosmetic, food, and pharmaceutical preparations. In this study, the effect of enantiomers of carvone on the central nervous system (CNS) was evaluated in mice. The LD50 value was 484.2 mg/kg (358.9–653.2) for (S)-(þ)-carvone, and 426.6 (389.0–478.6) mg/kg for (R)-()-carvone. Both enantiomers caused depressant effects, such as decrease in the response to the touch and ambulation, increase in sedation, palpebral ptosis, and antinociceptive effects. (S)-(þ)- and (R)-()-carvone caused a significant decrease in ambulation. (R)-()-Carvone appeared to be more effective than its corre-sponding enantiomer at 0.5 and 2.0 h after administration. However, (S)-(þ)-carvone was slightly more potent at 1 h. In potentiating pentobarbital sleeping time, (R)-()-car-vone was more effective than (S)-(þ)-carvone at 100 mg/kg, but was less potent at 200 mg/kg compared to the (þ)-enantiomer, indicating a sedative action. (S)-(þ)-Carvone at the dose of 200 mg/kg increased significantly the latency of convulsions induced by PTZ and PIC, but (R)-()-carvone was not effective against these convulsions. These results suggest that (S)-(þ)-carvone and (R)-()-carvone have depressant effect in the CNS. (S)-(þ)-Carvone appears to have anticonvulsant-like activity. Chirality 19:264–268, 2007. |
publishDate |
2007 |
dc.date.none.fl_str_mv |
2007 2024-08-09T18:05:17Z 2024-08-09 2024-08-09T18:05:17Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244 SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nobrega de. Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. Chirality (New York) , v. 19, p. 264-268, 2007. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244 |
url |
http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244 |
identifier_str_mv |
SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nobrega de. Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study. Chirality (New York) , v. 19, p. 264-268, 2007. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37244 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Campina Grande Brasil UFCG |
publisher.none.fl_str_mv |
Universidade Federal de Campina Grande Brasil UFCG |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFCG instname:Universidade Federal de Campina Grande (UFCG) instacron:UFCG |
instname_str |
Universidade Federal de Campina Grande (UFCG) |
instacron_str |
UFCG |
institution |
UFCG |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFCG |
collection |
Biblioteca Digital de Teses e Dissertações da UFCG |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFCG - Universidade Federal de Campina Grande (UFCG) |
repository.mail.fl_str_mv |
bdtd@setor.ufcg.edu.br || bdtd@setor.ufcg.edu.br |
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1809744632841502720 |