Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity.
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.
Saito
Akiko
A
Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan.
Doi
Yuki
Y
Tanaka
Akira
A
Matsuura
Nobuyasu
N
Ubukata
Makoto
M
Nakajima
Noriyuki
N
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
D000975:Antioxidants; D044945:Proanthocyanidins; D002392:Catechin