title: Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity.
abstract: A systematic synthesis of four natural epicatechin series procyanidin trimers [[4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2,3-trans-(-)-epi-catechin-(-)-epicatechin-(+)-catechin, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2,3-cis-tri-(-)-epicatechin: procyanidin C1, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2,3-trans-(-)-epicatechin-(+)-catechin-(+)-catechin: procyanidin C4, and [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2,3-cis-(-)-epicatechin-(+)-catechin-(-)-epicatechin] is described. Condensation of (2R,3R,4S)-5,7,3'4'-tetra-O-benzyl-4-(2"-ethoxyethyloxy)flavan derived from (-)-epicatechin as an electrophile with the dimeric nucleophiles in the presence of TMSOTf followed by deprotection yielded trimers. Inhibitory activities on the Maillard reaction and antioxidant activity on lipid peroxide of the synthesized oligomers were also investigated.
authors.affiliation: Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan.
authors.forename: Akiko
authors.initials: A
authors.lastname: Saito
authors.forename: Yuki
authors.initials: Y
authors.lastname: Doi
authors.forename: Akira
authors.initials: A
authors.lastname: Tanaka
authors.forename: Nobuyasu
authors.initials: N
authors.lastname: Matsuura
authors.forename: Makoto
authors.initials: M
authors.lastname: Ubukata
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Nakajima
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D002392:Catechin / Q000138:chemical synthesis* / Q000494:pharmacology; D015416:Maillard Reaction / Q000187:drug effects*; D044945:Proanthocyanidins / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D044945:Proanthocyanidins; D002392:Catechin