Structure, degree of polymerization, and starch hydrolase inhibition activities of bird cherry (Prunus padus) proanthocyanidins.

The structure of proanthocyanidins extracted from bird cherry fruits was characterized by HPLC-ESI/MS and MALDI-TOF/MS analyses, and their subunits and mean degree of polymerization (mDP) were investigated by thiolysis reaction, and the inhibition activity against starch hydrolases measured using the high-throughput turbidity assay. This is the first mass spectrometric analysis to thoroughly investigate the structure and mDP of proanthocyanidins in bird cherry fruits. Bird cherry proanthocyanidins were categorized as oligomeric proanthocyanidins (mDP = 5.6), which constituted of (epi)gallocatechins and (epi)catechins. The proanthocyanidins increased from a (epi)gallocatechin-[(epi)catechin] tetramer to a (epi)gallocatechin-[(epi)catechin] dodecamer through the addition of one (epi)catechin with both A-type and B-type linkages. The proanthocyanidins had potent α-amylase and α-glucosidase inhibition activities with IC values of 0.19 ± 0.01 µg/mL and 0.18 ± 0.006 µg/mL, comparing favorably to commercial drug acarbose. Bird cherry oligomeric proanthocyanidins are a promising starch hydrolase inhibitor for the application of potential functional food components.