A semisynthetic approach for the simultaneous reaction of grape seed polymeric procyanidins with catechin and epicatechin to obtain oligomeric procyanidins in large scale. (25th April 2019)

• Record Type: Journal Article
• Authors: Bai, Ruifang; Cui, Yan; Luo, Lanxin; Yuan, Danbing; Wei, Zongmin; Yu, Weichao; Sun, Baoshan
• Is Part Of: Food chemistry. Volume 278(2019)
• Page Start: 609
• Page End: 616
• Publication Date: 2019-04-25
• Subjects: (+)-Catechin (PubChem CID: 107957) -- (−)-Epicatechin (PubChem CID: 72276) -- Procyanidin B1 3-gallate (PubChem CID: 72193635) -- Procyanidin B3 (PubChem CID: 146798) -- Procyanidin B4 (PubChem CID: 147299) -- Procyanidin B2 (PubChem CID: 122738) -- Procyanidin B1 (PubChem CID: 11250133) -- Procyanidin C1 (PubChem CID: 169853); Semisynthesis -- Catechin -- Epicatechin -- Polymeric procyanidins -- Grape seed -- HSCCC; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2018.11.091
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Grape seed PPCs were converted into OPCs by simultaneous reaction with C and EC. The semisynthetic method was efficient and simple to gain dimers and trimers. 13 individual procyanidins were obtained by one-step HSCCC and prep-HPLC. The method could be applied to grape pomace and other procyanidin-rich plants. Abstract: Polymeric procyanidins (PPCs) were the major constituents of procyanidins, while they have poor bioactivity. To better utilize PPCs, a semisynthetic approach for converting PPCs to oligomeric procyanidins (OPCs) was proposed. Grape seed PPCs were simultaneously reacted with catechin (C) and epicatechin (EC) under acid condition. Combining response surface methodology (RSM) and single-factor experiments, an optimized semisynthetic condition was confirmed with the ratio of PPCs with C and EC of 1:1:1, temperature of 40 °C, reaction time of 20 min and 0.1 M methanolic HCl. High-speed counter-current chromatography (HSCCC) was adopted to obtain three fractions from semisynthetic products and preparative-HPLC was used to isolate individual procyanidins. Thirteen B-type procyanidins including monomers, dimers and trimers were got with high yield of 0.8–17.8 mg from 200 mg semisynthetic products and high purity over 91%. The developed semisynthesis combined with separation method was efficient to obtain individual OPCs in preparative scale.