title: Synthesis of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant activity.
abstract: Fifteen amides of cinnamic, ferulic and sinapic acids with natural and unnatural C-protected amino acids have been synthesized. The amides (E)-N-(feruloyl)-L-tyrosine methyl ester (10), (E)-N-(feruloyl)-L-phenylalanine t-butyl ester (11), (E)-N-(sinapoyl)-L-tyrosine methyl ester (13) and (E)-N-(sinapoyl)-L-phenylalanine t-butyl ester (15) with a free carboxyl group of amino acids have been found in nature. The rest of the compounds are unknown. The hydroxycinnamoyl amino acid conjugates have been studied for their antioxidant activity (AOA) in bulk phase lipid autoxidation. The highest AOA has been found for the compounds 11 and 15, which contain the same phenylalanine moiety.
authors.affiliation: South-West University N. Rilsky, Blagoevgrad 2700, Iv.Mihajlov str. 66, Bulgaria.
authors.forename: Maya
authors.initials: M
authors.lastname: Spasova
authors.forename: Vessela
authors.initials: V
authors.lastname: Kortenska-Kancheva
authors.forename: Iskra
authors.initials: I
authors.lastname: Totseva
authors.forename: Galya
authors.initials: G
authors.lastname: Ivanova
authors.forename: Lyubomir
authors.initials: L
authors.lastname: Georgiev
authors.forename: Tsenka
authors.initials: T
authors.lastname: Milkova
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000595:Amino Acid Sequence; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002934:Cinnamates / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry*; D015227:Lipid Peroxidation / Q000187:drug effects; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000975:Antioxidants; D002934:Cinnamates; D003373:Coumaric Acids; C029010:cinnamic acid; C004999:ferulic acid