Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: A comparative study.

Detalhes bibliográficos
Autor(a) principal: SOUSA, Damião Pergentino de.
Data de Publicação: 2007
Outros Autores: NÓBREGA, Franklin Ferreira de Farias., ALMEIDA, Reinaldo Nobrega de.
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.
id UFCG_36d120fd34078457798b9b05546f20ed
oai_identifier_str oai:localhost:riufcg/37244
network_acronym_str UFCG
network_name_str Biblioteca Digital de Teses e Dissertações da UFCG
repository_id_str 4851
spelling 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
_version_ 1809744632841502720