プロアントシアニジンの立体選択的合成研究とその生物活性

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  • 齊藤 安貴子
    独立行政法人理化学研究所 長田抗生物質研究室 富山県立バイオテクノロジーセンター
  • 中島 範行
    富山県立大学生物工学研究センター

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タイトル別名
  • Stereoselective Synthesis of Procyanidin Oligomers and Their Bioactivity
  • プロアントシアニジン ノ リッタイ センタクテキ ゴウセイ ケンキュウ ト ソノ セイブツ カッセイ

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The proanthocyanidins are known as condensed tannins and/or oligomeric flavonoids, and their many biological activities, powerful antioxidant activity, free-radical-scavenging activity and an anti-tumor-promoting effect, have been reported. 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 developed stereoselective condensation method under TMSOTf-catalyzed intermolecular and intramolecular conditions for procyanidin synthesis. The relationships between the structure of proanthocyanidins and their bioactivities (SAR) against the Maillard reaction inhibitory activity, antioxidant activity, DPPH radical scavenging activity, DNA polymerase inhibitory activity and DNA metabolic enzymes inhibitory activity using synthesized procyanidin oligomers including 3-substituted oligomers, were investigated.

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