Proanthocyanidins: from semisynthesis to isolation.
Abstract
A semisynthetic approach has been used for the preparative formation of eight dimeric procyanidins from B-type. As starting material for the semisynthesis, polymeric procyanidins from industrial by-products were applied. Under acidic conditions the interflavanoid linkages of the polymeric procyanidins are cleaved and the liberated (-)-epicatechin can react with nucleophiles, such as (+)- catechin or (-)-epicatechin. In this way, dimeric procyanidins are formed. The reaction mixtures of the semisynthesis can be successfully fractionated with high-speed countercurrent chromatography (HSCCC), and the structure elucidation was done by NMR spectroscopy. Moreover, a first approach to semisynthesize A-Type procyanidins from B-types will be shown.
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