Isolation and Structure Elucidation of Procyanidin Oligomers from Saskatoon Berries (Amelanchier alnifolia)

Proanthocyanidin oligomers with different degrees of polymerization were isolated from Saskatoon berries (Amelanchier alnifolia) by means of gel adsorption and normal-phase liquid chromatography. The proanthocyanidins were identified using electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, and thiolytic degradation coupled with reversed-phase liquid chromatography. The results established that Saskatoon berries contain proanthocyanidins from dimers through heptamers and higher polymers. Saskatoon proanthocyanidins are essentially of procyanidin type, consisting mainly of epicatechin units linked by B-type bonds. The simple procyanidin profile of Saskatoon berries allowed the procyanidins to be separated precisely according to their degrees of polymerization. In the future they can be used as standard compounds for qualitative and quantitative analysis of procyanidins as well as for elucidation of the biological activities of proanthocyanidins. Keywords: Amelanchier alnifolia; Saskatoon berry; ESI-MS; HPLC; NMR; procyanidins; isolation.