Molecular docking studies of a phlorotannin, dieckol isolated from Ecklonia cava with tyrosinase inhibitory activity SCIE SCOPUS

Cited 46 time in WEB OF SCIENCE Cited 54 time in Scopus
Title
Molecular docking studies of a phlorotannin, dieckol isolated from Ecklonia cava with tyrosinase inhibitory activity
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)
Publication Year
2012-01-01
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.
ISSN
0968-0896
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/3646
DOI
10.1016/j.bmc.2011.10.078
Bibliographic Citation
BIOORGANIC & MEDICINAL CHEMISTRY, v.20, no.1, pp.311 - 316, 2012
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Subject
MUSHROOM TYROSINASE; IN-VITRO; HUMAN MELANOCYTES; MELANOGENESIS; ACTIVATION; IDENTIFICATION; MECHANISM
Keywords
Dieckol; Tyrosinase; Melanin synthesis; Molecular docking
Type
Article
Language
English
Document Type
Article
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Related Researcher
Research Interests

Marine Biotechnology,Marine Natural Products,Bioactivities,해양생물공학,해양천연물학,생리활성

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