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dc.contributor.author
Santi, María Daniela
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dc.contributor.author
Bouzidi, C.
dc.contributor.author
Gorod, Noelia Stefania
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dc.contributor.author
Puiatti, Marcelo
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dc.contributor.author
Michel, S.
dc.contributor.author
Grougnet, R.
dc.contributor.author
Ortega, María Gabriela
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dc.date.available
2020-07-14T17:11:28Z
dc.date.issued
2019-02
dc.identifier.citation
Santi, María Daniela; Bouzidi, C.; Gorod, Noelia Stefania; Puiatti, Marcelo; Michel, S.; et al.; In vitro biological evaluation and molecular docking studies of natural and semisynthetic flavones from Gardenia oudiepe (Rubiaceae) as tyrosinase inhibitors; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 82; 2-2019; 241-245
dc.identifier.issn
0045-2068
dc.identifier.uri
http://hdl.handle.net/11336/109236
dc.description.abstract
Hyperpigmentation disorders are difficult to treat without causing permanent depigmentation or irritation. The most effective hypopigmenting agents are tyrosinase inhibitors, however some of those currently used have shown serious side effects. As several classes of flavonoids have already demonstrated ability to inhibit tyrosinase, a library of natural polymethoxyflavones isolated (1?7) from the bud exudate of Gardenia oudiepe and semi-synthetic derivatives (8,9) were evaluated. IC50 of the most active compounds were in the micromolar range. The strongest inhibitors 1, 2 and 3 all shared a 3′,4′-dimethoxy-5′-hydroxy trisubstituted B ring. These SAR conclusions were confirmed by molecular docking studies. The mode of interaction with the enzyme was elucidated, and important interactions between the most active compounds and catalytic residues of tyrosinase were observed. All of these data provided a library of compounds as potential leaders for the design of new depigmenting agents and formulations.Graphical abstractDownload high-res image (213KB)Download full-size imagePrevious article in issueNext article in issueKeywordsGardenia oudiepePolymethoxylated flavonesTyrosinase inhibitory activityStructure-activity relationshipsMolecular docking1. IntroductionMelanin biosynthesis is one of the most important factors in mammal skin color determination. This pigment protects against UV radiation, preventing mutations in cellular DNA, which could cause abnormal conformations in the expression of DNA [1], [2], [3], [4], [5]. An overproduction of melanin leads to hyperpigmentary disorders, such as lentigo, ephelides, nevus and other skin diseases. These pathologies result in devastating conditions for many patients, strongly impacting the quality of life [6], [7], [8]. Besides, agents currently used to reduce for hyperpigmentation, such as hydroquinone or kojic acid, have undesirable effects such as carcinogenesis, hepatotoxicity, dermatitis [9], [10]. Tyrosinase is responsible for the first two steps on melanin synthesis, and could be thus considered as a key-enzyme in the melanogenic cascade [9], [11], [12]. Flavonoids show a high potential for tyrosinase inhibition [6], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20] and may be an important source of depigmenting agents. We have recently reported the ability of nine polymethoxyflavones (PMF) isolated and semi-synthetized from the bud exudate of Gardenia oudiepe Vieill. (syn. G. cerifera S. Moore) to inhibit xanthine oxidase [21]. The potentiality of these compounds to interact in active sites of enzymes drove us to evaluate their monophenolase mushroom tyrosinase inhibitory activity, in order to establish some structure-activity relationships and to elucidate a plausible binding mode through molecular docking studies.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Academic Press Inc Elsevier Science
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dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
GARDENIA OUDIEPE
dc.subject
FLAVONES
dc.subject
TYROSINASE
dc.subject
DOCKING
dc.subject.classification
Otras Ciencias Biológicas
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dc.subject.classification
Ciencias Biológicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
In vitro biological evaluation and molecular docking studies of natural and semisynthetic flavones from Gardenia oudiepe (Rubiaceae) as tyrosinase inhibitors
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-07-13T16:11:46Z
dc.journal.volume
82
dc.journal.pagination
241-245
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Santi, María Daniela. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia. Cátedra de Farmacognosia; Argentina. 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
dc.description.fil
Fil: Bouzidi, C.. Université Paris Descartes; Francia
dc.description.fil
Fil: Gorod, Noelia Stefania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.description.fil
Fil: Puiatti, Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.description.fil
Fil: Michel, S.. Université Paris Descartes; Francia
dc.description.fil
Fil: Grougnet, R.. Université Paris Descartes; Francia
dc.description.fil
Fil: Ortega, María Gabriela. 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. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia. Cátedra de Farmacognosia; Argentina
dc.journal.title
Bioorganic Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S004520681830258X
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1016/j.bioorg.2018.10.034
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