TY - JOUR
T1 - (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant
AU - Wang, Hui Min
AU - Chen, Chung Yi
AU - Chen, Chun Yen
AU - Ho, Mei Ling
AU - Chou, Yi Ting
AU - Chang, Hou Chien
AU - Lee, Chih Hung
AU - Wang, Chau Zen
AU - Chu, I. Ming
N1 - Funding Information:
This investigation was financially supported by the National Science Council of Taiwan, ROC under the Grant Numbers of NSC97-2221-E-037-002- , NSC98-2221-E-037-005- , NSC-97-2320-B-242-002-MY3 and NSC 97-2321-B-037-001-MY2 ; Ministry of Economic Affairs , 98-EC-17-A-10-S2-0066 ; and by the Kaohsiung Medical University under Grant Number Q097002 . The authors would like to thank Xiu-Wei Kuo, Ya-Ling Yeh and Yung-Hsiu Chen for their assistance. The authors would also like thank Dr. Yau-Huei Wei and Min-Yii Julie Wang for the English editing.
Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2010/7/15
Y1 - 2010/7/15
N2 - Tyrosinase is the first and rate limiting enzyme in the synthesis of melanin pigments for coloring hair, skin, and eyes. As reported in this study, a natural product, (-)-N-formylanonaine isolated from the leaves of Michelia alba D.C. (Magnolianceae), was found to inhibit mushroom tyrosinase with an IC 50 of 74.3 μM and to have tyrosinase and melanin reducing activities in human epidermal melanocytes without apparent cytotoxicity to human cells, superior to the known tyrosinase inhibitors, such as kojic acid and 1-phenyl-2-thiourea (PTU). Based on homology modeling, the compound binds the active site by coordinating with two Cu 2+ ions. In addition, the compound had antioxidation activities in tests for scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH), reducing power, and chelating metal ions. To our knowledge, this is the first study to reveal the bioactivities of (-)-N-formylanonaine from this plant species.
AB - Tyrosinase is the first and rate limiting enzyme in the synthesis of melanin pigments for coloring hair, skin, and eyes. As reported in this study, a natural product, (-)-N-formylanonaine isolated from the leaves of Michelia alba D.C. (Magnolianceae), was found to inhibit mushroom tyrosinase with an IC 50 of 74.3 μM and to have tyrosinase and melanin reducing activities in human epidermal melanocytes without apparent cytotoxicity to human cells, superior to the known tyrosinase inhibitors, such as kojic acid and 1-phenyl-2-thiourea (PTU). Based on homology modeling, the compound binds the active site by coordinating with two Cu 2+ ions. In addition, the compound had antioxidation activities in tests for scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH), reducing power, and chelating metal ions. To our knowledge, this is the first study to reveal the bioactivities of (-)-N-formylanonaine from this plant species.
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U2 - 10.1016/j.bmc.2010.05.045
DO - 10.1016/j.bmc.2010.05.045
M3 - Article
C2 - 20584613
AN - SCOPUS:77955332765
SN - 0968-0896
VL - 18
SP - 5241
EP - 5247
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 14
ER -