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Open AccessArticle

Tyrosinase Inhibition and Kinetic Details of Puerol A Having But-2-Enolide Structure from Amorpha fruticosa

1
Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University, Jinju 52828, Korea
2
Division of Applied Life Science (BK21 plus), PMBBRC, Gyeongsang National University, Jinju 52828, Korea
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2020, 25(10), 2344; https://doi.org/10.3390/molecules25102344
Received: 26 April 2020 / Revised: 14 May 2020 / Accepted: 14 May 2020 / Published: 18 May 2020
Puerol A (1) from Amorpha fruticosa showed highly potent inhibition against both monophenolase (IC50 = 2.2 μM) and diphenolase (IC50 = 3.8 μM) of tyrosinase. We tried to obtain a full story of enzyme inhibitory behavior for inhibitor 1 because the butenolide skeleton has never been reported as a tyrosinase inhibitor. Puerol A was proved as a reversible, competitive, simple slow-binding inhibitor, according to the respective parameters; k3 = 0.0279 μM−1 min−1 and k4 = 0.003 min−1. A longer lag-phase and a reduced static-state activity of the enzyme explained that puerol A had a tight formation of the complex with Emet. Dose-dependent inhibition was also confirmed by high-performance liquid chromatography (HPLC) analysis using N-acetyl-l-tyrosine as a substrate, which was completely inhibited at 20 μM. A high binding affinity of 1 to tyrosinase was confirmed by fluorescence quenching analysis. Moreover, puerol A decreased melanin content in the B16 melanoma cell dose-dependently with an IC50 of 11.4 μM. View Full-Text
Keywords: Amorpha fruticosa; puerol A; tyrosinase; binding affinity; anti-pigmentation Amorpha fruticosa; puerol A; tyrosinase; binding affinity; anti-pigmentation
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Kim, J.H.; Jang, D.H.; Lee, K.W.; Kim, K.D.; Shah, A.B.; Zhumanova, K.; Park, K.H. Tyrosinase Inhibition and Kinetic Details of Puerol A Having But-2-Enolide Structure from Amorpha fruticosa. Molecules 2020, 25, 2344.

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