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Tyrosinase inhibitors isolated from the edible brown algaEcklonia stolonifera

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Abstract

Extracts from seventeen seaweeds were determined for tyrosinase inhibitory activity using mushroom tyrosinase with L-tyrosine as a substrate. Only one of them,Ecklonia stolonifera Okamura (Laminariaceae) belonging to brown algae, showed high tyrosinase inhibitory activity. Bioassay-guided fractionation of the active ethyl acetate (EtOAc) soluble fraction from the methanolic extract ofE. stolonifera, led us to the isolation of phloroglucinol derivatives [phloroglucinol (1), eckstolonol (2), eckol (3), phlorofucofuroeckol A (4), and dieckol (5)]. Compounds1~5 were found to inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with IC50 values of 92.8, 126, 33.2, 177, and 2.16 μg/mL, respectively. It was compared with those of kojic acid and arbutin, well-known tyrosinase inhibitors, with IC50 values of 6.32 and 112 μg/ mL, respectively. The inhibitory kinetics analyzed from Lineweaver-Burk plots, showed compounds1 and2 to be competitive inhibitors with Ki of 2.3×10-4 and 3.1×10-4 M, and compounds3×5 to be noncompetitive inhibitors with Ki of 1.9×10-5, 1.4×10-3 and 1.5×10-5 M, respectively. This work showed that phloroglucinol derivatives, natural compounds found in brown algae, could be involved in the control of pigmentation in plants and other organisms through inhibition of tyrosinase activity using L-tyrosine as a substrate.

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Authors and Affiliations

  1. Faculty of Food Science and Biotechnology, Pukyong National University, 608-737, Busan, Korea

    Hye Sook Kang, Hyung Rak Kim, Dae Seok Byun, Byeng Wha Son, Taek Jeong Nam & Jae Sue Choi

  2. Department of Chemistry, Pukyong National University, 608-737, Busan, Korea

    Byeng Wha Son

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  1. Hye Sook Kang
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Correspondence to Jae Sue Choi.

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Kang, H.S., Kim, H.R., Byun, D.S. et al. Tyrosinase inhibitors isolated from the edible brown algaEcklonia stolonifera . Arch Pharm Res 27, 1226–1232 (2004). https://doi.org/10.1007/BF02975886

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