A semisynthetic approach for the simultaneous reaction of grape seed polymeric procyanidins with catechin and epicatechin to obtain oligomeric procyanidins in large scale.
Food Chem
; 278: 609-616, 2019 Apr 25.
Article
in En
| MEDLINE
| ID: mdl-30583419
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 111, temperature of 40⯰C, reaction time of 20â¯min and 0.1â¯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 0.8-17.8â¯mg from 200â¯mg semisynthetic products and high purity over 91%. The developed semisynthesis combined with separation method was efficient to obtain individual OPCs in preparative scale.
Key words
(+)-Catechin (PubChem CID: 107957); (−)-Epicatechin (PubChem CID: 72276); Catechin; Epicatechin; Grape seed; HSCCC; Polymeric procyanidins; Procyanidin B1 (PubChem CID: 11250133); Procyanidin B1 3-gallate (PubChem CID: 72193635); Procyanidin B2 (PubChem CID: 122738); Procyanidin B3 (PubChem CID: 146798); Procyanidin B4 (PubChem CID: 147299); Procyanidin C1 (PubChem CID: 169853); Semisynthesis
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Catechin
/
Vitis
/
Biflavonoids
/
Proanthocyanidins
Language:
En
Journal:
Food Chem
Year:
2019
Document type:
Article
Affiliation country: