Synthesis of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant activity.
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.
Spasova
Maya
M
South-West University N. Rilsky, Blagoevgrad 2700, Iv.Mihajlov str. 66, Bulgaria.
Kortenska-Kancheva
Vessela
V
Totseva
Iskra
I
Ivanova
Galya
G
Georgiev
Lyubomir
L
Milkova
Tsenka
T
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
D000577:Amides; D000975:Antioxidants; D002934:Cinnamates; D003373:Coumaric Acids; C029010:cinnamic acid; C004999:ferulic acid