title: Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant.
abstract: We previously reported that caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) acted as both a good antioxidant and tyrosinase inhibitor, in particular when caffeic acid was conjugated with proline or amino acids having aromatic ring like phenylalanine. Here, various hydroxycinnamic acid (HCA) derivatives were further conjugated with phenylalanyl hydroxamic acid and prolyl hydroxamic acid (HCA-Phe-NHOH and HCA-Pro-NHOH) to study the structure and activity relationship as both antioxidants and tyrosinase inhibitors. When their biological activities were evaluated, all HCA-Phe-NHOH and HCA-Pro-NHOH exhibited enhanced antioxidant activity compared to HCA alone. Moreover, derivatives of caffeic acid, ferulic acid, and sinapic acid inhibited lipid peroxidation more efficiently than vitamin E analogue (Trolox). In addition, derivatives of caffeic acid and sinapic acid efficiently inhibited tyrosinase activity and reduced melanin content in melanocytes Mel-Ab cell.
authors.affiliation: School of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea.
authors.forename: Seon-Yeong
authors.initials: SY
authors.lastname: Kwak
authors.forename: Jin-Kyoung
authors.initials: JK
authors.lastname: Yang
authors.forename: Hye-Ryung
authors.initials: HR
authors.lastname: Choi
authors.forename: Kyung-Chan
authors.initials: KC
authors.lastname: Park
authors.forename: Young-Bu
authors.initials: YB
authors.lastname: Kim
authors.forename: Yoon-Sik
authors.initials: YS
authors.lastname: Lee
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010649:Phenylalanine / Q000031:analogs & derivatives*; D011392:Proline / Q000031:analogs & derivatives*; D017382:Reactive Oxygen Species; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D003373:Coumaric Acids; D004791:Enzyme Inhibitors; D017382:Reactive Oxygen Species; D010649:Phenylalanine; D011392:Proline; D014442:Monophenol Monooxygenase