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Phenols Displaying Tyrosinase Inhibition From Humulus Lupulus

Phenols Displaying Tyrosinase Inhibition From Humulus Lupulus

Dae Wook Kim, Hyun Sim Woo, Jeong Yoon Kim, Jin Ah Ryuk, Ki Hun Park, Byoung Seob Ko

J Enzyme Inhib Med Chem. 2016 Oct;31(5):742-7.

PMID: 26162028

Abstract:

Tyrosinase is the rate-limiting enzyme for the production of melanin and other pigments via the oxidation of l-tyrosine. The methanol extract from Humulus lupulus showed potent inhibition against mushroom tyrosinase. The bioactivity-guided fractionation of this methanol extract resulted in the isolation of seven flavonoids (1-7), identified as xanthohumol (1), 4'-O-methylxanthohumol (2), xanthohumol C (3), flavokawain C (4), xanthoumol B (5), 6-prenylnaringenin (6) and isoxanthohumol (7). All isolated flavonoids (1-7) effectively inhibited the monophenolase (IC50s = 15.4-58.4 µM) and diphenolase (IC50s = 27.1-117.4 µM) activities of tyrosinase. Kinetic studies using Lineweaver-Burk and Dixon-plots revealed that chalcones (1-5) were competitive inhibitors, whereas flavanones (6 and 7) exhibited both mixed and non-competitive inhibitory characteristics. In conclusion, this study is the first to demonstrate that the phenolic phytochemicals of H. lupulus display potent inhibitory activities against tyrosinase.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP37308751	Flavokawain C		37308-75-1	Price

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