Stereo-selective activity of menthol on GABA(A) receptor

Autores
Corvalán, Natalia Andrea; Zygadlo, Julio Alberto; Garcia, Daniel Asmed
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Menthol is a naturally occurring compound, which has three chiral centers that define eight possible optically actives stereoisomers. Neuroactivity of menthol and related agents by affecting neuronal intracellular signaling or by modulation of neurotransmitter-gated currents has been reported. Furthermore, stereo-selectivity of menthol in its analgesic activity as well as in its sensory properties and other biological activities was also described. The present study is the first contribution to the description of stereo-selectivity of GABAA receptor against the most possible isomers of menthol, discussed in terms of their chirality. The results showed that only (+)-menthol, among the five stereoisomers analyzed, was active, stimulating in a dose-response manner the binding of an allosteric GABAA receptor ligand. Taking into account these results, and comparing them with those of some active phenolic compounds, it is strongly suggested that the existence of a relative spatial location of its substituents with respect to the ring (equatorial position of all substituents and (1S,2R,5S)-configuration) as well as the presence in the cyclic molecule of an aliphatic non polar group (isopropyl) with free rotation near to a polar group (hydroxyl) are crucial points to demonstrate activity on the receptor.
Fil: Corvalán, Natalia Andrea. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Garcia, Daniel Asmed. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Menthol
Stereo-Isomers
Stereo-Selectivity
Gabaa-Receptor
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/26539
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Stereo-selective activity of menthol on GABA(A) receptorCorvalán, Natalia AndreaZygadlo, Julio AlbertoGarcia, Daniel AsmedMentholStereo-IsomersStereo-SelectivityGabaa-Receptorhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Menthol is a naturally occurring compound, which has three chiral centers that define eight possible optically actives stereoisomers. Neuroactivity of menthol and related agents by affecting neuronal intracellular signaling or by modulation of neurotransmitter-gated currents has been reported. Furthermore, stereo-selectivity of menthol in its analgesic activity as well as in its sensory properties and other biological activities was also described. The present study is the first contribution to the description of stereo-selectivity of GABAA receptor against the most possible isomers of menthol, discussed in terms of their chirality. The results showed that only (+)-menthol, among the five stereoisomers analyzed, was active, stimulating in a dose-response manner the binding of an allosteric GABAA receptor ligand. Taking into account these results, and comparing them with those of some active phenolic compounds, it is strongly suggested that the existence of a relative spatial location of its substituents with respect to the ring (equatorial position of all substituents and (1S,2R,5S)-configuration) as well as the presence in the cyclic molecule of an aliphatic non polar group (isopropyl) with free rotation near to a polar group (hydroxyl) are crucial points to demonstrate activity on the receptor.Fil: Corvalán, Natalia Andrea. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Garcia, Daniel Asmed. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaWiley2009-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/26539Corvalán, Natalia Andrea; Zygadlo, Julio Alberto; Garcia, Daniel Asmed; Stereo-selective activity of menthol on GABA(A) receptor; Wiley; Chirality; 21; 5; 5-2009; 525-5300899-00421520-636XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chir.20631info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chir.20631/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:19Zoai:ri.conicet.gov.ar:11336/26539instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:44:19.44CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereo-selective activity of menthol on GABA(A) receptor
title Stereo-selective activity of menthol on GABA(A) receptor
spellingShingle Stereo-selective activity of menthol on GABA(A) receptor
Corvalán, Natalia Andrea
Menthol
Stereo-Isomers
Stereo-Selectivity
Gabaa-Receptor
title_short Stereo-selective activity of menthol on GABA(A) receptor
title_full Stereo-selective activity of menthol on GABA(A) receptor
title_fullStr Stereo-selective activity of menthol on GABA(A) receptor
title_full_unstemmed Stereo-selective activity of menthol on GABA(A) receptor
title_sort Stereo-selective activity of menthol on GABA(A) receptor
dc.creator.none.fl_str_mv Corvalán, Natalia Andrea
Zygadlo, Julio Alberto
Garcia, Daniel Asmed
author Corvalán, Natalia Andrea
author_facet Corvalán, Natalia Andrea
Zygadlo, Julio Alberto
Garcia, Daniel Asmed
author_role author
author2 Zygadlo, Julio Alberto
Garcia, Daniel Asmed
author2_role author
author
dc.subject.none.fl_str_mv Menthol
Stereo-Isomers
Stereo-Selectivity
Gabaa-Receptor
topic Menthol
Stereo-Isomers
Stereo-Selectivity
Gabaa-Receptor
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Menthol is a naturally occurring compound, which has three chiral centers that define eight possible optically actives stereoisomers. Neuroactivity of menthol and related agents by affecting neuronal intracellular signaling or by modulation of neurotransmitter-gated currents has been reported. Furthermore, stereo-selectivity of menthol in its analgesic activity as well as in its sensory properties and other biological activities was also described. The present study is the first contribution to the description of stereo-selectivity of GABAA receptor against the most possible isomers of menthol, discussed in terms of their chirality. The results showed that only (+)-menthol, among the five stereoisomers analyzed, was active, stimulating in a dose-response manner the binding of an allosteric GABAA receptor ligand. Taking into account these results, and comparing them with those of some active phenolic compounds, it is strongly suggested that the existence of a relative spatial location of its substituents with respect to the ring (equatorial position of all substituents and (1S,2R,5S)-configuration) as well as the presence in the cyclic molecule of an aliphatic non polar group (isopropyl) with free rotation near to a polar group (hydroxyl) are crucial points to demonstrate activity on the receptor.
Fil: Corvalán, Natalia Andrea. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Garcia, Daniel Asmed. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description Menthol is a naturally occurring compound, which has three chiral centers that define eight possible optically actives stereoisomers. Neuroactivity of menthol and related agents by affecting neuronal intracellular signaling or by modulation of neurotransmitter-gated currents has been reported. Furthermore, stereo-selectivity of menthol in its analgesic activity as well as in its sensory properties and other biological activities was also described. The present study is the first contribution to the description of stereo-selectivity of GABAA receptor against the most possible isomers of menthol, discussed in terms of their chirality. The results showed that only (+)-menthol, among the five stereoisomers analyzed, was active, stimulating in a dose-response manner the binding of an allosteric GABAA receptor ligand. Taking into account these results, and comparing them with those of some active phenolic compounds, it is strongly suggested that the existence of a relative spatial location of its substituents with respect to the ring (equatorial position of all substituents and (1S,2R,5S)-configuration) as well as the presence in the cyclic molecule of an aliphatic non polar group (isopropyl) with free rotation near to a polar group (hydroxyl) are crucial points to demonstrate activity on the receptor.
publishDate 2009
dc.date.none.fl_str_mv 2009-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/26539
Corvalán, Natalia Andrea; Zygadlo, Julio Alberto; Garcia, Daniel Asmed; Stereo-selective activity of menthol on GABA(A) receptor; Wiley; Chirality; 21; 5; 5-2009; 525-530
0899-0042
1520-636X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/26539
identifier_str_mv Corvalán, Natalia Andrea; Zygadlo, Julio Alberto; Garcia, Daniel Asmed; Stereo-selective activity of menthol on GABA(A) receptor; Wiley; Chirality; 21; 5; 5-2009; 525-530
0899-0042
1520-636X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chir.20631
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chir.20631/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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