The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach
Tyrosinase is the central enzyme involved in the highly complex process of melanin formation, catalyzing the rate-limiting steps of this biosynthetic pathway. Due to such a preponderant role, it has become a major target in the treatment of undesired skin pigmentation conditions and also in the prev...
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MDPI AG
2021-06-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/12/6192 |
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| author | Patrícia Correia Hélder Oliveira Paula Araújo Natércia F. Brás Ana Rita Pereira Joana Moreira Victor de Freitas Nuno Mateus Joana Oliveira Iva Fernandes |
| author_facet | Patrícia Correia Hélder Oliveira Paula Araújo Natércia F. Brás Ana Rita Pereira Joana Moreira Victor de Freitas Nuno Mateus Joana Oliveira Iva Fernandes |
| author_sort | Patrícia Correia |
| collection | DOAJ |
| description | Tyrosinase is the central enzyme involved in the highly complex process of melanin formation, catalyzing the rate-limiting steps of this biosynthetic pathway. Due to such a preponderant role, it has become a major target in the treatment of undesired skin pigmentation conditions and also in the prevention of enzymatic food browning. Numerous phenolic-based structures from natural sources have been pointed out as potential tyrosinase inhibitors, including anthocyanins. The aim of the present study was to individually assess the tyrosinase inhibitory activity of eight purified compounds with a variable degree of structural complexity: native anthocyanins, deoxyanthocyanins, and pyranoanthocyanins. The latter two, the groups of anthocyanin-related compounds with enhanced stability, were tested for the first time. Compounds <b>1</b> to <b>4</b> (luteolinidin, deoxymalvidin, cyanidin-, and malvidin-3-<i>O</i>-glucoside) revealed to be the most effective inhibitors, and further kinetic studies suggested their inhibition mechanism to be of a competitive nature. Structure–activity relationships were proposed based on molecular docking studies conducted with mushroom tyrosinase (mTYR) and human tyrosinase-related protein 1 (hTYRP1) crystal structures, providing information about the binding affinity and the different types of interactions established with the enzyme’s active center which corroborated the findings of the inhibition and kinetic studies. Overall, these results support the applicability of these compounds as pigmentation modulators. |
| first_indexed | 2024-03-10T10:36:45Z |
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| id | doaj.art-0ddc4bceb9ed47978823e9f4944a6952 |
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| language | English |
| last_indexed | 2024-03-10T10:36:45Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-0ddc4bceb9ed47978823e9f4944a69522023-11-21T23:15:25ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-06-012212619210.3390/ijms22126192The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico ApproachPatrícia Correia0Hélder Oliveira1Paula Araújo2Natércia F. Brás3Ana Rita Pereira4Joana Moreira5Victor de Freitas6Nuno Mateus7Joana Oliveira8Iva Fernandes9LAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLaboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculty of Pharmacy of the University of Porto, Rua Jorge Viterbo Ferreira nº 228, 4050-313 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalLAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalTyrosinase is the central enzyme involved in the highly complex process of melanin formation, catalyzing the rate-limiting steps of this biosynthetic pathway. Due to such a preponderant role, it has become a major target in the treatment of undesired skin pigmentation conditions and also in the prevention of enzymatic food browning. Numerous phenolic-based structures from natural sources have been pointed out as potential tyrosinase inhibitors, including anthocyanins. The aim of the present study was to individually assess the tyrosinase inhibitory activity of eight purified compounds with a variable degree of structural complexity: native anthocyanins, deoxyanthocyanins, and pyranoanthocyanins. The latter two, the groups of anthocyanin-related compounds with enhanced stability, were tested for the first time. Compounds <b>1</b> to <b>4</b> (luteolinidin, deoxymalvidin, cyanidin-, and malvidin-3-<i>O</i>-glucoside) revealed to be the most effective inhibitors, and further kinetic studies suggested their inhibition mechanism to be of a competitive nature. Structure–activity relationships were proposed based on molecular docking studies conducted with mushroom tyrosinase (mTYR) and human tyrosinase-related protein 1 (hTYRP1) crystal structures, providing information about the binding affinity and the different types of interactions established with the enzyme’s active center which corroborated the findings of the inhibition and kinetic studies. Overall, these results support the applicability of these compounds as pigmentation modulators.https://www.mdpi.com/1422-0067/22/12/6192anthocyaninsdeoxyanthocyaninspyranoanthocyaninstyrosinasepigmentationenzymatic inhibition |
| spellingShingle | Patrícia Correia Hélder Oliveira Paula Araújo Natércia F. Brás Ana Rita Pereira Joana Moreira Victor de Freitas Nuno Mateus Joana Oliveira Iva Fernandes The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach International Journal of Molecular Sciences anthocyanins deoxyanthocyanins pyranoanthocyanins tyrosinase pigmentation enzymatic inhibition |
| title | The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach |
| title_full | The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach |
| title_fullStr | The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach |
| title_full_unstemmed | The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach |
| title_short | The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach |
| title_sort | role of anthocyanins deoxyanthocyanins and pyranoanthocyanins on the modulation of tyrosinase activity an in vitro and in silico approach |
| topic | anthocyanins deoxyanthocyanins pyranoanthocyanins tyrosinase pigmentation enzymatic inhibition |
| url | https://www.mdpi.com/1422-0067/22/12/6192 |
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