Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity
- Autores
- Peralta, Mariana Andrea; Santi, María Daniela; Agnese, Alicia Mariel; Cabrera, Jose Luis; Ortega, María Gabriela
- Año de publicación
- 2014
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented.
Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina
Fil: Santi, María Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina
Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina
Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina
Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina - Materia
-
Dalea Elegans
Fabaceae
Prenylated Flavonone
C-Methyl Flavonoids
Chemical Reassignment
Antityrosinase Activity - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/13699
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oai:ri.conicet.gov.ar:11336/13699 |
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Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activityPeralta, Mariana AndreaSanti, María DanielaAgnese, Alicia MarielCabrera, Jose LuisOrtega, María GabrielaDalea ElegansFabaceaePrenylated FlavononeC-Methyl FlavonoidsChemical ReassignmentAntityrosinase Activityhttps://purl.org/becyt/ford/1.7https://purl.org/becyt/ford/1In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented.Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; ArgentinaFil: Santi, María Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; ArgentinaFil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; ArgentinaFil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; ArgentinaFil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; ArgentinaElsevier Science2014-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/13699Peralta, Mariana Andrea; Santi, María Daniela; Agnese, Alicia Mariel; Cabrera, Jose Luis; Ortega, María Gabriela; Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity; Elsevier Science; Phytochemistry Letters; 10; 12-2014; 260-2671874-39001876-7486enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytol.2014.10.012info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1874390014001888info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:57:58Zoai:ri.conicet.gov.ar:11336/13699instacron: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 09:57:58.639CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
title |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
spellingShingle |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity Peralta, Mariana Andrea Dalea Elegans Fabaceae Prenylated Flavonone C-Methyl Flavonoids Chemical Reassignment Antityrosinase Activity |
title_short |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
title_full |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
title_fullStr |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
title_full_unstemmed |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
title_sort |
Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
dc.creator.none.fl_str_mv |
Peralta, Mariana Andrea Santi, María Daniela Agnese, Alicia Mariel Cabrera, Jose Luis Ortega, María Gabriela |
author |
Peralta, Mariana Andrea |
author_facet |
Peralta, Mariana Andrea Santi, María Daniela Agnese, Alicia Mariel Cabrera, Jose Luis Ortega, María Gabriela |
author_role |
author |
author2 |
Santi, María Daniela Agnese, Alicia Mariel Cabrera, Jose Luis Ortega, María Gabriela |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
Dalea Elegans Fabaceae Prenylated Flavonone C-Methyl Flavonoids Chemical Reassignment Antityrosinase Activity |
topic |
Dalea Elegans Fabaceae Prenylated Flavonone C-Methyl Flavonoids Chemical Reassignment Antityrosinase Activity |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.7 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented. Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Santi, María Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina |
description |
In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-12 |
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/11336/13699 Peralta, Mariana Andrea; Santi, María Daniela; Agnese, Alicia Mariel; Cabrera, Jose Luis; Ortega, María Gabriela; Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity; Elsevier Science; Phytochemistry Letters; 10; 12-2014; 260-267 1874-3900 1876-7486 |
url |
http://hdl.handle.net/11336/13699 |
identifier_str_mv |
Peralta, Mariana Andrea; Santi, María Daniela; Agnese, Alicia Mariel; Cabrera, Jose Luis; Ortega, María Gabriela; Flavanoids from Dalea elegans: chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity; Elsevier Science; Phytochemistry Letters; 10; 12-2014; 260-267 1874-3900 1876-7486 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytol.2014.10.012 info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1874390014001888 |
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 application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier Science |
publisher.none.fl_str_mv |
Elsevier Science |
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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1842269492831322112 |
score |
13.13397 |