title: (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant.
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 IC50 of 74.3 microM 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 Cu2+ 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.
authors.affiliation: Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, and the Department of Orthopaedics, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan, ROC. davidw@kmu.edu.tw
authors.forename: Hui-Min
authors.initials: HM
authors.lastname: Wang
authors.forename: Chung-Yi
authors.initials: CY
authors.lastname: Chen
authors.forename: Chun-Yen
authors.initials: CY
authors.lastname: Chen
authors.forename: Mei-Ling
authors.initials: ML
authors.lastname: Ho
authors.forename: Yi-Ting
authors.initials: YT
authors.lastname: Chou
authors.forename: Hou-Chien
authors.initials: HC
authors.lastname: Chang
authors.forename: Chih-Hung
authors.initials: CH
authors.lastname: Lee
authors.forename: Chau-Zen
authors.initials: CZ
authors.lastname: Wang
authors.forename: I-Ming
authors.initials: IM
authors.lastname: Chu
mesh_terms: D000363:Agaricales / Q000201:enzymology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D006801:Humans; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects; D031566:Magnolia / Q000737:chemistry*; D008543:Melanins / Q000037:antagonists & inhibitors / Q000378:metabolism; D008544:Melanocytes / Q000166:cytology / Q000187:drug effects / Q000201:enzymology; D008958:Models, Molecular; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D001060:Aporphines; D008543:Melanins; C553481:N-formylanonaine; D010936:Plant Extracts; D014442:Monophenol Monooxygenase