Novel flavan-3-ol-glutathione conjugates from the degradation of proanthocyanidins as highly bioactive antioxidants. (22nd April 2020)

• Record Type: Journal Article
• Authors: Bai, Ruifang; Luo, Siqi; Luo, Lanxin; Zhao, Jian; Zhang, Shuting; Li, Lingxi; Cui, Yan
• Is Part Of: New journal of chemistry. Volume 44:Number 17(2020)
• Page Start: 7158
• Page End: 7168
• Publication Date: 2020-04-22
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c9nj06207f
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Synthesis, preparation and antioxidant capacity evaluation of flavan-3-ol-glutathione conjugates. Abstract : A new degradation method was developed for converting polymeric proanthocyanidins into highly bioactive flavan-3-ol derivatives in the presence of glutathione (GSH) as a nucleophile. Combining single-factor experiments and Box–Behnken factorial design (BBD), optimized degradation conditions were established. Grape seed proanthocyanidins were reacted with GSH at a ratio of 1 : 3 with 0.2 M methanolic HCl, a temperature of 55 °C and a reaction time of 30 min. The degradation products were largely isolated and prepared by one-step high-speed counter-current chromatography (HSCCC) and preparative HPLC. Three monomeric proanthocyanidins and four novel GSH conjugates were obtained with a high yield (85%) and high purity (over 91%). Also, the protective effects of all these compounds against H2 O2 -induced oxidative stress in PC-12 neuroblastoma cells were investigated. GSH conjugates were shown to be better at increasing the antioxidative effect than their underivatized monomers and GSH, indicating their better neuroprotective effects against oxidative stress.