(-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant

Hui Min Wang, Chung Yi Chen, Chun Yen Chen, Mei Ling Ho, Yi Ting Chou, Hou Chien Chang, Chih Hung Lee, Chau Zen Wang, I. Ming Chu

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Abstract

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.

Original languageEnglish
Pages (from-to)5241-5247
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number14
DOIs
Publication statusPublished - 2010 Jul 15

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Wang, H. M., Chen, C. Y., Chen, C. Y., Ho, M. L., Chou, Y. T., Chang, H. C., Lee, C. H., Wang, C. Z., & Chu, I. M. (2010). (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant. Bioorganic and Medicinal Chemistry, 18(14), 5241-5247. https://doi.org/10.1016/j.bmc.2010.05.045