Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex

Autores
Martínez Medina, Juan José; Naso, Luciana; Pérez, Ana L.; Rizzi, Alberto; Ferrer, Evelina Gloria; Williams, Patricia Ana María
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Based on the known antioxidant effect of flavonoids, baicalin (baic) found in roots of Scutellaria has been selected. Its coordination complex with the oxidovanadium(IV) cation, Na4[VO(baic)2].6H2O (VIVO(baic)), was synthesized at pH 9 in ethanol and characterized by physicochemical methods. Spectrophotometric studies at pH 9 showed a ligand: metal stoichiometry of 2:1. By vibrational spectroscopy a coordination mode through the cis 5-OH and 6-OH deprotonated groups is inferred. EPR spectroscopy shows an environment of four aryloxide (ArO−) groups in the equatorial plane of the V=O moiety, both in solution and in the solid complex. The antioxidant capacity against superoxide and peroxyl radicals of VIVO(baic) resulted greater than for baicalin and correlated with previous results obtained for other VOflavonoid complexes. The coordination mode produces delocalization of the electron density and the stabilization of the radical formed by interaction with external radicals. The complex and the ligand displayed no toxic (Artemia salina test) and no mutagenic (Ames test) effects. The complex improved the ability of the ligand to reduce cell viability of human lung cancer cell lines (A549) generating reactive oxygen species (ROS) in cells, being this effect reversed by pre-incubation of the cells with antioxidants such as vitamins C and E. The addition of NAC (N-acetyl-L-cysteine, a sequestering agent of free radicals) suppresses the anticancer effect, confirming the oxidative stress mechanism. The complex interacted with bovine serum albumin (BSA) with stronger binding than baicalin and the mechanisms involved H bonding and van der Waals interactions.
Centro de Química Inorgánica
Materia
Química
BSA binding
Oxidovanadium (IV) complex
Baicalin
Antioxidant
Anticancer
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/103793

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network_name_str SEDICI (UNLP)
spelling Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complexMartínez Medina, Juan JoséNaso, LucianaPérez, Ana L.Rizzi, AlbertoFerrer, Evelina GloriaWilliams, Patricia Ana MaríaQuímicaBSA bindingOxidovanadium (IV) complexBaicalinAntioxidantAnticancerBased on the known antioxidant effect of flavonoids, baicalin (baic) found in roots of <i>Scutellaria</i> has been selected. Its coordination complex with the oxidovanadium(IV) cation, Na<sub>4</sub>[VO(baic)<sub>2</sub>].6H<sub>2</sub>O (V<sup>IV</sup>O(baic)), was synthesized at pH 9 in ethanol and characterized by physicochemical methods. Spectrophotometric studies at pH 9 showed a ligand: metal stoichiometry of 2:1. By vibrational spectroscopy a coordination mode through the cis 5-OH and 6-OH deprotonated groups is inferred. EPR spectroscopy shows an environment of four aryloxide (ArO−) groups in the equatorial plane of the V=O moiety, both in solution and in the solid complex. The antioxidant capacity against superoxide and peroxyl radicals of V<sup>IV</sup>O(baic) resulted greater than for baicalin and correlated with previous results obtained for other VOflavonoid complexes. The coordination mode produces delocalization of the electron density and the stabilization of the radical formed by interaction with external radicals. The complex and the ligand displayed no toxic (<i>Artemia salina</i> test) and no mutagenic (Ames test) effects. The complex improved the ability of the ligand to reduce cell viability of human lung cancer cell lines (A549) generating reactive oxygen species (ROS) in cells, being this effect reversed by pre-incubation of the cells with antioxidants such as vitamins C and E. The addition of NAC (N-acetyl-L-cysteine, a sequestering agent of free radicals) suppresses the anticancer effect, confirming the oxidative stress mechanism. The complex interacted with bovine serum albumin (BSA) with stronger binding than baicalin and the mechanisms involved H bonding and van der Waals interactions.Centro de Química Inorgánica2016-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf150-161http://sedici.unlp.edu.ar/handle/10915/103793enginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0162013416303762?via%3Dihubinfo:eu-repo/semantics/altIdentifier/issn/0162-0134info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2016.11.005info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-03T10:54:48Zoai:sedici.unlp.edu.ar:10915/103793Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-03 10:54:49.107SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
title Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
spellingShingle Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
Martínez Medina, Juan José
Química
BSA binding
Oxidovanadium (IV) complex
Baicalin
Antioxidant
Anticancer
title_short Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
title_full Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
title_fullStr Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
title_full_unstemmed Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
title_sort Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex
dc.creator.none.fl_str_mv Martínez Medina, Juan José
Naso, Luciana
Pérez, Ana L.
Rizzi, Alberto
Ferrer, Evelina Gloria
Williams, Patricia Ana María
author Martínez Medina, Juan José
author_facet Martínez Medina, Juan José
Naso, Luciana
Pérez, Ana L.
Rizzi, Alberto
Ferrer, Evelina Gloria
Williams, Patricia Ana María
author_role author
author2 Naso, Luciana
Pérez, Ana L.
Rizzi, Alberto
Ferrer, Evelina Gloria
Williams, Patricia Ana María
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Química
BSA binding
Oxidovanadium (IV) complex
Baicalin
Antioxidant
Anticancer
topic Química
BSA binding
Oxidovanadium (IV) complex
Baicalin
Antioxidant
Anticancer
dc.description.none.fl_txt_mv Based on the known antioxidant effect of flavonoids, baicalin (baic) found in roots of <i>Scutellaria</i> has been selected. Its coordination complex with the oxidovanadium(IV) cation, Na<sub>4</sub>[VO(baic)<sub>2</sub>].6H<sub>2</sub>O (V<sup>IV</sup>O(baic)), was synthesized at pH 9 in ethanol and characterized by physicochemical methods. Spectrophotometric studies at pH 9 showed a ligand: metal stoichiometry of 2:1. By vibrational spectroscopy a coordination mode through the cis 5-OH and 6-OH deprotonated groups is inferred. EPR spectroscopy shows an environment of four aryloxide (ArO−) groups in the equatorial plane of the V=O moiety, both in solution and in the solid complex. The antioxidant capacity against superoxide and peroxyl radicals of V<sup>IV</sup>O(baic) resulted greater than for baicalin and correlated with previous results obtained for other VOflavonoid complexes. The coordination mode produces delocalization of the electron density and the stabilization of the radical formed by interaction with external radicals. The complex and the ligand displayed no toxic (<i>Artemia salina</i> test) and no mutagenic (Ames test) effects. The complex improved the ability of the ligand to reduce cell viability of human lung cancer cell lines (A549) generating reactive oxygen species (ROS) in cells, being this effect reversed by pre-incubation of the cells with antioxidants such as vitamins C and E. The addition of NAC (N-acetyl-L-cysteine, a sequestering agent of free radicals) suppresses the anticancer effect, confirming the oxidative stress mechanism. The complex interacted with bovine serum albumin (BSA) with stronger binding than baicalin and the mechanisms involved H bonding and van der Waals interactions.
Centro de Química Inorgánica
description Based on the known antioxidant effect of flavonoids, baicalin (baic) found in roots of <i>Scutellaria</i> has been selected. Its coordination complex with the oxidovanadium(IV) cation, Na<sub>4</sub>[VO(baic)<sub>2</sub>].6H<sub>2</sub>O (V<sup>IV</sup>O(baic)), was synthesized at pH 9 in ethanol and characterized by physicochemical methods. Spectrophotometric studies at pH 9 showed a ligand: metal stoichiometry of 2:1. By vibrational spectroscopy a coordination mode through the cis 5-OH and 6-OH deprotonated groups is inferred. EPR spectroscopy shows an environment of four aryloxide (ArO−) groups in the equatorial plane of the V=O moiety, both in solution and in the solid complex. The antioxidant capacity against superoxide and peroxyl radicals of V<sup>IV</sup>O(baic) resulted greater than for baicalin and correlated with previous results obtained for other VOflavonoid complexes. The coordination mode produces delocalization of the electron density and the stabilization of the radical formed by interaction with external radicals. The complex and the ligand displayed no toxic (<i>Artemia salina</i> test) and no mutagenic (Ames test) effects. The complex improved the ability of the ligand to reduce cell viability of human lung cancer cell lines (A549) generating reactive oxygen species (ROS) in cells, being this effect reversed by pre-incubation of the cells with antioxidants such as vitamins C and E. The addition of NAC (N-acetyl-L-cysteine, a sequestering agent of free radicals) suppresses the anticancer effect, confirming the oxidative stress mechanism. The complex interacted with bovine serum albumin (BSA) with stronger binding than baicalin and the mechanisms involved H bonding and van der Waals interactions.
publishDate 2016
dc.date.none.fl_str_mv 2016-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
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status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/103793
url http://sedici.unlp.edu.ar/handle/10915/103793
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language eng
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info:eu-repo/semantics/altIdentifier/issn/0162-0134
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2016.11.005
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
150-161
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instname:Universidad Nacional de La Plata
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instname_str Universidad Nacional de La Plata
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repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
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