(-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant.
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.
Wang
Hui-Min
HM
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
Chen
Chung-Yi
CY
Chen
Chun-Yen
CY
Ho
Mei-Ling
ML
Chou
Yi-Ting
YT
Chang
Hou-Chien
HC
Lee
Chih-Hung
CH
Wang
Chau-Zen
CZ
Chu
I-Ming
IM
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
D000975:Antioxidants; D001060:Aporphines; D008543:Melanins; C553481:N-formylanonaine; D010936:Plant Extracts; D014442:Monophenol Monooxygenase