Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: a comparative study.
Many terpenes are used therapeutically, and as flavor and fragrance materials. (R)-(-)-Carvone, the main constituent of spearmint oil, and (S)-(+)-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)-(+)-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)-(+)- and (R)-(-)-carvone caused a significant decrease in ambulation. (R)-(-)-Carvone appeared to be more effective than its corresponding enantiomer at 0.5 and 2.0 h after administration. However, (S)-(+)-carvone was slightly more potent at 1 h. In potentiating pentobarbital sleeping time, (R)-(-)-carvone was more effective than (S)-(+)-carvone at 100 mg/kg, but was less potent at 200 mg/kg compared to the (+)-enantiomer, indicating a sedative action. (S)-(+)-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)-(+)-carvone and (R)-(-)-carvone have depressant effect in the CNS. (S)-(+)-Carvone appears to have anticonvulsant-like activity.
de Sousa
Damião Pergentino
DP
Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000 São Cristóvão, Sergipe, Brazil.
de Farias Nóbrega
Franklin Ferreira
FF
de Almeida
Reinaldo Nóbrega
RN
D000700:Analgesics / Q000494:pharmacology; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects*; D002490:Central Nervous System / Q000187:drug effects*; D000081005:Cyclohexane Monoterpenes; D008297:Male; D051379:Mice; D008956:Models, Chemical; D039821:Monoterpenes / Q000737:chemistry*; D009043:Motor Activity; D009822:Oils, Volatile / Q000737:chemistry; D010424:Pentobarbital / Q000737:chemistry / Q000494:pharmacology; D012640:Seizures / Q000139:chemically induced*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000700:Analgesics; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D009822:Oils, Volatile; C006923:carvone; D010424:Pentobarbital