Molecular docking studies of a phlorotannin, dieckol isolated from Ecklonia cava with tyrosinase inhibitory activity
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Title
- Molecular docking studies of a phlorotannin, dieckol isolated from Ecklonia cava with tyrosinase inhibitory activity
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Author(s)
- Kang, Sung-Myung; Heo, Soo-Jin; Kim, Kil-Nam; Lee, Seung-Hong; Yang, Hae-Mi; Kim, Areum-Daseul; Jeon, You-Jin
- KIOST Author(s)
- Heo, Soo Jin(허수진)
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Alternative Author(s)
- 허수진
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Publication Year
- 2012-01-01
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Abstract
- In this study, the phlorotannin dieckol, which was isolated from the brown alga Ecklonia cava, was examined for its inhibitory effects on melanin synthesis. Tyrosinase inhibitors are important agents for cosmetic products. We therefore examined the inhibitory effects of dieckol on mushroom tyrosinase and melanin synthesis, and analyzed its binding modes using the crystal structure of Bacillus megaterium tyrosinase (PDB ID: 3NM8). Dieckol inhibited mushroom tyrosinase with an IC(50) of 20 mu M and was more effective as a cellular tyrosinase having melanin reducing activities than the commercial inhibitor, arbutin, in B16F10 melanoma cells, and without apparent cytotoxicity. It was found that dieckol behaved as a non-competitive inhibitor with L-tyrosine substrates. For further insight, we predicted the 3D structure of tyrosinase and used a docking algorithm to simulate binding between tyrosinase and dieckol. These molecular modeling studies were successful (calculated binding energy value: -126.12 kcal/mol), and indicated that dieckol interacts with His208, Met215, and Gly46. These results suggest that dieckol has great potential to be further developed as a pharmaceutical or cosmetic agent for use in dermatological disorders associated with melanin. (C) 2011 Elsevier Ltd. All rights reserved.
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ISSN
- 0968-0896
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/3646
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DOI
- 10.1016/j.bmc.2011.10.078
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Bibliographic Citation
- BIOORGANIC & MEDICINAL CHEMISTRY, v.20, no.1, pp.311 - 316, 2012
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Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
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Subject
- MUSHROOM TYROSINASE; IN-VITRO; HUMAN MELANOCYTES; MELANOGENESIS; ACTIVATION; IDENTIFICATION; MECHANISM
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Keywords
- Dieckol; Tyrosinase; Melanin synthesis; Molecular docking
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Type
- Article
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Language
- English
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Document Type
- Article
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