The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach

Abstract

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 1 to 4 (luteolinidin, deoxymalvidin, cyanidin-, and malvidin-3-O-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.

In SilicoInteractions of the Components from theSchinus terebinthifoliusExtract with Human Tyrosinase

“…However, MM-PBSA calculations (Figure 7) indicate that there are ligand-copper interactions for 17, suggesting a competitive inhibition. Previous experimental studies with mushroom tyrosinase [50] indicate that 17 exhibit a competitive type of inhibition, thus supporting MM-PBSA results.…”

Natural Melanogenesis Inhibitor, Antioxidant, and Collagen Biosynthesis Stimulator of Phytochemicals in Rice Bran and Husk Extracts from Purple Glutinous Rice (Oryza sativa L. cv. Pieisu 1 CMU) for Cosmetic Application

“…In consequence, kinetic studies revealed that cyanidin-3- O -glucoside acts as a competitive inhibitor for tyrosinase, with an inhibition constant of 40.31 ± 3.61 µM. In addition, molecular simulations demonstrated that the oxygen atom at ring A of cyanidin-3- O -glucoside can interact with the central Cu 2+ of the human tyrosinase enzyme with the lowest binding energy of −10.8 kcal/mol [ 37 ]. Although Lee et al reported that cyanidin-3- O -glucoside slightly reduced the activity of murine tyrosinase enzyme by comparison to arbutin as a positive control [ 38 ].…”

Behind the Scenes of Anthocyanins—From the Health Benefits to Potential Applications in Food, Pharmaceutical and Cosmetic Fields

“…This effect was also recently explored using cyanidin- and malvidin-3- O -glucosides pure standards and also elderberry and red wine ACNs extracts [ 247 ]. Overall, most of the compounds were found to exhibit UV-filter capacity, attenuate the production of reactive oxygen species in human skin keratinocytes and fibroblasts and showed inhibitory activity of skin-degrading enzymes (Tyrosinase, elastase, hyaluronidase, and collagenase) in the absence of cytotoxic effects [ 247 , 248 ]. Considering the described features of these compounds, a formulation containing them would benefit from a dual function of photoprotection blended with an anti-aging effect.…”