Integrated Utilization of Red Radish for the Efficient Production of High-Purity Procyanidin Dimers

Red radish was extracted by methanol to obtain crude radish procyanidin extracts. The purity of procyanidin (PP) and procyanidin dimers (PD) of crude radish procyanidin extracts under different ratios of methanol to radish was optimized to achieve the best extraction performance. Then the crude radish procyanidin extracts was, respectively, processed six macroporous resins separation to separate radish procyanidin oligomers (RPO) and polymers (RPP). Depolymerization of radish procyanidin polymers (RPP) into oligomers was then conducted. N-Acetylneuraminate lyase (NAL) was first used as the enzyme to depolymerize RPP. The depolymerization yield (DY) under different depolymerized conditions was also investigated. Results showed the DY of RPP would achieve 53.24 ± 0.35% at the best conditions. Then the high-purity procyanidin dimers was prepared by depolymerized procyanidin oligomers and PRO. Additionally, the chemical structure of the preparative radish procyanidin dimers was elucidated by high-resolution mass spectrometry and one- and two-dimensional NMR.