Structure⁻Activity Relationship of the Tyrosinase Inhibitors Kuwanon G, Mulberrofuran G, and Albanol B from Species: A Kinetics and Molecular Docking Study

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Jun 13

PMID 29891812

Citations 15

Authors

Prashamsa Koirala

Su Hui Seong

Yajuan Zhou

Srijan Shrestha

Hyun Ah Jung

Jae Sue Choi

Affiliations

Soon will be listed here.

Abstract

Kuwanon G (KG) and benzofuran flavonoids such as mulberrofuran G (MG) and albanol B (AB) isolated from sp. are reported to exhibit anti-Alzheimer’s disease, anti-inflammatory, fungicidal, anti-cancer, anti-bacterial, and anti-tyrosinase properties. We investigated the inhibition of mono- and diphenolase activity of mushroom tyrosinase by KG, MG, and AB. KG and MG displayed acceptable inhibition activity compared to kojic acid. AB did not show any activity up to 350 µM. MG displayed six-fold higher inhibition of -tyrosine oxidation (IC = 6.35 ± 0.45 µM) compared to kojic acid (IC = 36.0 µM). Kinetic studies revealed that KG and MG inhibited monophenolase activity of tyrosinase in a competitive manner. Docking simulations of KG and MG demonstrated favorable binding energies with amino acid residues of the active sites of tyrosinase. Our investigation of the structure-activity relationship of the fused benzofuran flavonoids (MG vs. AB) implicated the methyl cyclohexene ring moiety in tyrosinase inhibition. The enzyme substrate and relative structural analyses demonstrated that KG and MG from sp. could be useful natural tyrosinase inhibitors in foods or cosmetics.

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