Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity |
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| Authors: | Saito Akiko Doi Yuki Tanaka Akira Matsuura Nobuyasu Ubukata Makoto Nakajima Noriyuki |
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| Institution: | Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan. |
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| 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. |
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