Anti-tyrosinase and antioxidant activity of meroterpene bakuchiol from Psoralea corylifolia (L.).

Food Chem

University of Bologna, Department of Chemistry "G. Ciamician", Via S. Giacomo 11, 40126 Bologna, Italy; Tecnopolo di Rimini, Via Dario Campana 71, 47922 Rimini, Italy. Electronic address:

Published: March 2023

Bakuchiol is gaining major interest for treatments against skin photoaging. The kinetics of mushroom tyrosinase inhibition by bakuchiol, by real-time oxygen sensing and UV-vis monitoring (475 nm), showed competitive inhibition with average K constant (µM, 30 °C, pH 6.8) of 6.71 ± 1.23 and 1.15 ± 0.34 for monophenolase and diphenolase reactions respectively, with respective IC 37.22 ± 5.18 and 6.91 ± 0.96 ∼ at 1 mM substrate, compared to kojic acid IC 34.02 ± 5.51 and 16.86 ± 3.28 μM. Fluorescence quenching showed a single binding mode with formation constant K 1.02 × 10 M. The antioxidant activity was studied by inhibited autoxidation of styrene and cumene (PhCl, 30 °C) affording inhibition constant k = 18.1 ± 6.6 (10Ms, 30 °C) and of MeLin in Triton™ X-100 micelles giving k = 0.16 ± 0.03 (10Ms, 37 °C). Stoichiometric factor was 1.9 ± 0.1. ReqEPR spectroscopy afforded the BDE(OH) as 81.7 ± 0.1 kcal/mol. Bakuchiol is a potent tyrosinase inhibitor with good antioxidant activity having major potential as natural food preservative against oxidation and food-browning.

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http://dx.doi.org/10.1016/j.foodchem.2022.134953DOI Listing

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