Inhibition characteristics and mechanism of tyrosinase using five citrus flavonoids: A spectroscopic and molecular dynamics simulation study

Journal of Food BiochemistryVolume 46, Issue 12 e14484 ORIGINAL ARTICLE Inhibition characteristics and mechanism of tyrosinase using five citrus flavonoids: A spectroscopic and molecular dynamics simulation study Wenfeng Li, Corresponding Author Wenfeng Li drnaruto@snnu.edu.cn shanxiliwenfeng@163.com orcid.org/0000-0002-3250-3062 School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, China Correspondence Wenfeng Li, 16 Juxian Road, Fuling district, Chongqing, China. Email: drnaruto@snnu.edu.cn; shanxiliwenfeng@163.comSearch for more papers by this authorHua Tian, Hua Tian School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, ChinaSearch for more papers by this authorFuting Guo, Futing Guo School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, ChinaSearch for more papers by this authorYingmei Wu, Yingmei Wu The Chongqing Engineering Laboratory for Green Cultivation and Deep Processing of the Three Gorges Reservoir Area's Medicinal Herbs, College of Biology and Food Engineering, Chongqing Three Gorges University, Chongqing, ChinaSearch for more papers by this author Wenfeng Li, Corresponding Author Wenfeng Li drnaruto@snnu.edu.cn shanxiliwenfeng@163.com orcid.org/0000-0002-3250-3062 School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, China Correspondence Wenfeng Li, 16 Juxian Road, Fuling district, Chongqing, China. Email: drnaruto@snnu.edu.cn; shanxiliwenfeng@163.comSearch for more papers by this authorHua Tian, Hua Tian School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, ChinaSearch for more papers by this authorFuting Guo, Futing Guo School of Life Science and Biotechnology|, Yangtze Normal University, Chongqing, ChinaSearch for more papers by this authorYingmei Wu, Yingmei Wu The Chongqing Engineering Laboratory for Green Cultivation and Deep Processing of the Three Gorges Reservoir Area's Medicinal Herbs, College of Biology and Food Engineering, Chongqing Three Gorges University, Chongqing, ChinaSearch for more papers by this author First published: 14 October 2022 https://doi.org/10.1111/jfbc.14484Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract This work presents a comparative analysis of the tyrosinase inhibitory effects of five citrus flavonoids, namely hesperetin, hesperidin, neohesperidin, naringenin and naringin. Visbile, fluorescence, and fourier transform infrared (FITR) spectroscopies, and molecular dynamic methods were employed to compare the anti-tyrosinase mechanisms of each flavonoid. Hesperetin, neohesperidin, naringenin and naringin exhibited potent inhibitory activities with IC50 values of 0.74 ± 0.05, 2.19 ± 0.03, 7.50 ± 9.82 and 24.94 ± 8.43 μmol/ml, respectively, all of which were higher than that of kojic acid (0.04 ± 0.02 μmol/ml). The enzymatic kinetics results suggested that hesperetin and naringenin were reversible inhibitors on tyrosinase in the mixed-type manner. H-bond and hydrophobic interactions were found to drive the binding of tyrosinase with hesperetin or naringenin, which subsequently changed the FTIR spectroscopy results by decreasing the α-helix ratio and increasing the β-turn, β-sheet and random coil ratio in tyrosinase. Molecular dynamics simulation not only verified some of the experimental results, but also suggested that the binding of hesperetin and naringenin to tyrosinase was spontaneous. The findings of this study indicate that citrus flavonoids are a promising dietary resource for tyrosinase inhibition. Practical applications Hesperetin, hesperidin, neohesperidin, naringenin and naringin were typical citrus flavonoids that have anti-obesity, anti-oxidation, anti-inflammation and anti-diabetes activities. Current study suggested that hesperetin and naringenin were effective reversible inhibitors on tyrosinase in the mixed-type manner. Hesperetin and naringenin might serve as nutritional and chemical agents for regulating the tyrosinase activity to control melanin level in vivo. CONFLICTS OF INTEREST The authors declare no competing financial interest. Open Research DATA AVAILABILITY STATEMENT Research data are not shared. Supporting Information Filename Description jfbc14484-sup-0001-FigureS1-S2.docxWord 2007 document , 48.8 MB Figure S1-S2 Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume46, Issue12December 2022e14484 RelatedInformation