Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach
Flavonoids are widely distributed in plants and constitute the most common polyphenolic phytoconstituents in the human diet. In this study, the in vitro inhibitory activity of 44 different flavonoids (1–44) against mushroom tyrosinase was studied, and an in silico study and type of inhibition for th...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2022-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | http://dx.doi.org/10.1080/14756366.2021.2014832 |
| _version_ | 1818754688903806976 |
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| author | Katarzyna Jakimiuk Suat Sari Robert Milewski Claudiu T. Supuran Didem Şöhretoğlu Michał Tomczyk |
| author_facet | Katarzyna Jakimiuk Suat Sari Robert Milewski Claudiu T. Supuran Didem Şöhretoğlu Michał Tomczyk |
| author_sort | Katarzyna Jakimiuk |
| collection | DOAJ |
| description | Flavonoids are widely distributed in plants and constitute the most common polyphenolic phytoconstituents in the human diet. In this study, the in vitro inhibitory activity of 44 different flavonoids (1–44) against mushroom tyrosinase was studied, and an in silico study and type of inhibition for the most active compounds were evaluated too. Tyrosinase inhibitors block melanogenesis and take part in melanin production or distribution leading to pigmentation diseases. The in vitro study showed that quercetin was a competitive inhibitor (IC50=44.38 ± 0.13 µM) and achieved higher antityrosinase activity than the control inhibitor kojic acid. The in silico results highlight the importance of the flavonoid core with a hydroxyl at C7 as a strong contributor of interference with tyrosinase activity. According to the developed statistical model, the activity of molecules depends on hydroxylation at C3 and methylation at C8, C7, and C3 in the benzo-γ-pyrane ring of the flavonoids. |
| first_indexed | 2024-12-18T05:27:14Z |
| format | Article |
| id | doaj.art-49f0bba030924193a71ddae437471e85 |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-12-18T05:27:14Z |
| publishDate | 2022-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-49f0bba030924193a71ddae437471e852022-12-21T21:19:30ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742022-12-0137142743610.1080/14756366.2021.20148322014832Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approachKatarzyna Jakimiuk0Suat Sari1Robert Milewski2Claudiu T. Supuran3Didem Şöhretoğlu4Michał Tomczyk5Department of Pharmacognosy, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of BiałystokDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe UniversityDepartment of Statistics and Medical Informatics, Faculty of Health Science, Medical University of BiałystokNeurofarba Department, Universita degli Studi di FirenzeDepartment of Pharmacognosy, Faculty of Pharmacy, Hacettepe UniversityDepartment of Pharmacognosy, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of BiałystokFlavonoids are widely distributed in plants and constitute the most common polyphenolic phytoconstituents in the human diet. In this study, the in vitro inhibitory activity of 44 different flavonoids (1–44) against mushroom tyrosinase was studied, and an in silico study and type of inhibition for the most active compounds were evaluated too. Tyrosinase inhibitors block melanogenesis and take part in melanin production or distribution leading to pigmentation diseases. The in vitro study showed that quercetin was a competitive inhibitor (IC50=44.38 ± 0.13 µM) and achieved higher antityrosinase activity than the control inhibitor kojic acid. The in silico results highlight the importance of the flavonoid core with a hydroxyl at C7 as a strong contributor of interference with tyrosinase activity. According to the developed statistical model, the activity of molecules depends on hydroxylation at C3 and methylation at C8, C7, and C3 in the benzo-γ-pyrane ring of the flavonoids.http://dx.doi.org/10.1080/14756366.2021.2014832flavonoidmolecular dockingtyrosinasestructure-activity relationshipstatistical analysis |
| spellingShingle | Katarzyna Jakimiuk Suat Sari Robert Milewski Claudiu T. Supuran Didem Şöhretoğlu Michał Tomczyk Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach Journal of Enzyme Inhibition and Medicinal Chemistry flavonoid molecular docking tyrosinase structure-activity relationship statistical analysis |
| title | Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach |
| title_full | Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach |
| title_fullStr | Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach |
| title_full_unstemmed | Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach |
| title_short | Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach |
| title_sort | flavonoids as tyrosinase inhibitors in in silico and in vitro models basic framework of sar using a statistical modelling approach |
| topic | flavonoid molecular docking tyrosinase structure-activity relationship statistical analysis |
| url | http://dx.doi.org/10.1080/14756366.2021.2014832 |
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