Tyrosinase Inhibitory Activities of Safrole fromMyristica fragransHoutt.

Abstract

Five phenylpropanoids (1-5), a benzofuran neolignan (6), two 8-O-4'-neolignans (7-8), and five tetrahydrofuran lignans (9-13) were isolated from a methanol extract of Myristica fragrans seeds. The structures of 1-13 were determined by 1 Hand 13C-NMR spectroscopic data analyses and a comparison with the literature data. Compound 3 was isolated for the first time from this plant. All the isolated compounds were evaluated for their inhibitory activity against tyrosinase. Among them, safrole (1) showed significant inhibitions against both the monophenolase (IC 50 =32.11 µM) and diphenolase (IC 50 =27.32 µM) activities of tyrosinase. The kinetic analysis shows that safrole (1) is competitive inhibitors for both monophenolase and diphenolase. The apparent inhibition constant (K i ) for safrole (1) binding with free enzyme was determined to be 16.05 and 13.66 µM for monophenolase and diphenolase, respectively.

Functionalized Tyrosinase-Lignin Nanoparticles as Sustainable Catalysts for the Oxidation of Phenols

“…The reactivity of tyrosinase towards lignin is debated. Lignans, the secondary metabolites resembling the dimeric units of lignin, generally showed inhibitory activity against tyrosinase [ 44 , 45 , 46 ], and the catalytic effect of tyrosinase in the oxidation of milled wood lignin was found to be negligible with respect to that of laccase and horseradish peroxidase [ 47 ]. On the other hand, tyrosinase from Agaricus bisporus was reported to cleave the 4- O -5 and Cα-Cβ bonds of some representative dimeric lignin model compounds (4-phenoxylphenol and guaiacyl glycerol-β-guaiacylether) [ 48 ].…”

Plants and Natural Products for the Treatment of Skin Hyperpigmentation – A Review

“…The aerial material of Crataegus azarolus L. (Rosaceae) macerated in MeOH for 10 d followed by further partitioning gave an EtOAc fraction containing ursolic acid (48), hyperoside (49), and virtexin-2″-O-rhamnoside (50) as major constituents. This fraction proved cytotoxic to B16F10 melanoma cells (IC 50 = 50 µg/ mL), and its application resulted in significant decreases in cellular melanin production at 50 µg/mL (p < 0.01) [34].…”

“…This noncytotoxic compound functions by downregulating TYR, TRP-1, and TRP-2 (10-50 µM), with TRP-2 being the most responsive to the compound [47]. In addition, another nutmeg-derived active safrole (75) inhibits the monophenolase and diphenolase activities of mushroom TYR (IC 50 = 32.11 and 27.32 µM, respectively) [48].…”