43(P-5) プロアントシアニジンの化学 : 系統的オリゴマーの合成ならびに構造-活性相関とその応用(ポスター発表の部)

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The proanthocyanidins are known as condensed tannins and/or oligomeric flavonoids, in which flavan-3-ol units are linked together by carbon-carbon bonds from the 4-position of one unit to the 8-position of the next unit. Many biological activities, powerful antioxidant activity, free-radical-scavenging activity and an anti-tumor-promoting effect, have been reported for flavonoids and their investigation is now increasingly important. Proanthocyanidins have been obtained from many kinds of plants, but because they are usually obtained as a complex mixture of structurally related compounds, it is very difficult to isolate them in a pure form. Consequently, we planned to develop efficient synthetic methods leading to procyanidins with a high level of purity and stereoselectivity for biological assay. We previously developed that TMSOTf-catalyzed intermolecular- and intramolecular-condensation and described their inhibitory activity of the Maillard reaction. We report here the simple efficient method to synthesize 3-substituted procyanidin oligomers constituted with (+)-catechin and (-)-epicatechin using TMSOTf-catalyzed intermolecular condensation. And we also report the stereoselection of 3,4-cis and 3,4-trans catechin and catechin condensation under intramolecular coupling method. The inhibitory activity of the Maillard reaction, antioxidant activity, DPPH radical scavenging activity, DNA polymerase inhibitory activity and DNA metabolic enzymes inhibitory activity were tested using synthesized procyanidin oligomers including 3-substituted oligomers. From the results of these activity tests, it became apparent that the oligomer length and the presence of substituted groups at the C-3 position in the proanthocyanidin oligomer were very important for biological activities, however; the antioxidant activity and DPPH scavenging activity of these compounds were not parallel to the other inhibitory activities. Further work is in progress to clarify the relationships between the structure of proanthocyanidins and their bioactivities.
天然有機化合物討論会の論文
2004-10-01

43(P-5) プロアントシアニジンの化学 : 系統的オリゴマーの合成ならびに構造-活性相関とその応用(ポスター発表の部)

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