Efficient isolation of major procyanidin A-type dimers from peanut skins and B-type dimers from grape seeds

被引:66
作者
Appeldoorn, Maaike M. [1 ,2 ]
Sanders, Mark [1 ]
Vincken, Jean-Paul [1 ]
Cheynier, Veronique [3 ]
Le Guerneve, Christine [3 ]
Hollman, Peter C. H. [2 ]
Gruppen, Harry [1 ]
机构
[1] Wageningen Univ, Food Chem Lab, NL-6700 EV Wageningen, Netherlands
[2] RIKILT Inst Food Safety, NL-6700 AE Wageningen, Netherlands
[3] INRA, UMR SPO, F-34060 Montpellier, France
关键词
Grape seeds; Peanut skins; Isolation; Procyanidin dimers; Reversed-phase HPLC; LOW-DENSITY-LIPOPROTEIN; NORMAL-PHASE; ANTIOXIDANT ACTIVITY; PROANTHOCYANIDINS; POLYMERIZATION; CHROMATOGRAPHY; FRACTIONATION; SEPARATION; EPICATECHIN-(4-BETA-8)-EPICATECHIN; ASSIGNMENTS;
D O I
10.1016/j.foodchem.2009.04.047
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In order to fully explore the biofunctional potential of proanthocyanidins (PA), isolated and well-characterised PA dimers are of great importance. Current methods to obtain pure A- and B-type dimers are laborious, because they comprise multiple chromatographic steps, often yielding only one or two specific dimers. In the current study, an efficient isolation procedure is described, to isolate a large variety of A-type dimers from peanut skins and B-type dimers from grape seeds. Yields increased 20-400 times for A-type dimers and about 10 times for B-type dimers compared to other methods with a lesser number of chromatographic steps. Dinners isolated from peanut skins were identified as; epicatechin-(2-O-7, 4-8)-catechin (A1), epicatechin-(2-O-7, 4-8)-epicatechin (A2), epicatechin-(2-O-7, 4-6)-catechin, epicatechin-(2-O-7, 4-8)-entcatechin, isolated from peanut skins for the first time, and epicatechin-(4-6)-catechin (B7). Dimers from grape seeds were identified as; epicatechin-(4-8)-catechin (B1), epicatechin-(4-8)-epicatechin (132), catechin-(4-8)-catechin (B3) and catechin-(4-8)-epicatechin (B4). (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:713 / 720
页数:8
相关论文
共 40 条
[1]   Procyanidin Dimers Are Metabolized by Human Microbiota with 2-(3,4-Dihydroxyphenyl)acetic Acid and 5-(3,4-Dihydroxyphenyl)-γ-valerolactone as the Major Metabolites [J].
Appeldoorn, Maaike M. ;
Vincken, Jean-Paul ;
Aura, Anna-Marja ;
Hollman, Peter C. H. ;
Gruppen, Harry .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (03) :1084-1092
[2]   Absorption and urinary excretion of procyanidin B2 [epicatechin-(4β-8)-epicatechin] in rats [J].
Baba, S ;
Osakabe, N ;
Natsume, M ;
Terao, J .
FREE RADICAL BIOLOGY AND MEDICINE, 2002, 33 (01) :142-148
[3]  
Davis AL, 1996, MAGN RESON CHEM, V34, P887, DOI 10.1002/(SICI)1097-458X(199611)34:11<887::AID-OMR995>3.0.CO
[4]  
2-U
[5]   Unambiguous assignments for free dimeric proanthocyanidin phenols from 2D NMR [J].
DeBruyne, T ;
Pieters, LAC ;
Dommisse, RA ;
Kolodziej, H ;
Wray, V ;
Domke, T ;
Vlietnick, AJ .
PHYTOCHEMISTRY, 1996, 43 (01) :265-272
[6]  
Donovan JL, 2002, BRIT J NUTR, V87, P299, DOI 10.1079/BJNBJN2001517
[7]  
Foo LY, 1999, FOOD CHEM, V64, P511
[8]   Accumulation and extractability of grape skin tannins and anthocyanins at different advanced physiological stages [J].
Fournand, David ;
Vicens, Anysia ;
Sidhoum, Louise ;
Souquet, Jean-Marc ;
Moutounet, Michel ;
Cheynier, Veronique .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (19) :7331-7338
[9]   Concentrations of proanthocyanidins in common foods and estimations of normal consumption [J].
Gu, LW ;
Kelm, MA ;
Hammerstone, JF ;
Beecher, G ;
Holden, J ;
Haytowitz, D ;
Gebhardt, S ;
Prior, RL .
JOURNAL OF NUTRITION, 2004, 134 (03) :613-617
[10]   Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods [J].
Gu, LW ;
Kelm, MA ;
Hammerstone, JF ;
Zhang, Z ;
Beecher, G ;
Holden, J ;
Haytowitz, D ;
Prior, RL .
JOURNAL OF MASS SPECTROMETRY, 2003, 38 (12) :1272-1280