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
[31]   Rapid fractionation of grape seed proanthocyanidins [J].
Saucier, C ;
Mirabel, M ;
Daviaud, F ;
Longieras, A ;
Glories, Y .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (12) :5732-5735
[32]   Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica [J].
Shahat, AA ;
Cos, P ;
De Bruyne, T ;
Apers, S ;
Hammouda, FM ;
Ismail, SI ;
Azzam, S ;
Claeys, M ;
Goovaerts, E ;
Pieters, L ;
Vanden Berghe, D ;
Vlietinck, AJ .
PLANTA MEDICA, 2002, 68 (06) :539-541
[33]   Apple (Malus pumila) procyanidins fractionated according to the degree of polymerization using normal-phase chromatography and characterized by HPLC-ESI/MS and MALDI-TOF/MS [J].
Shoji, T ;
Masumoto, S ;
Moriichi, N ;
Kanda, T ;
Ohtake, Y .
JOURNAL OF CHROMATOGRAPHY A, 2006, 1102 (1-2) :206-213
[34]   Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled [J].
Steinberg, FM ;
Holt, RR ;
Schmitz, HH ;
Keen, CL .
JOURNAL OF NUTRITIONAL BIOCHEMISTRY, 2002, 13 (11) :645-652
[35]   Aqueous extract of peanut skin and its main constituent procyanidin Al suppress serum IgE and IgG1 levels in mice-immunized with ovalbumin [J].
Takano, Fumihide ;
Takata, Takanobu ;
Yoshihara, Akio ;
Nakamura, Yuka ;
Arima, Yukiko ;
Ohta, Tomihisa .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2007, 30 (05) :922-927
[36]   Antioxidant and membrane effects of procyanidin dimers and trimers isolated from peanut and cocoa [J].
Verstraeten, SV ;
Hammerstone, JF ;
Keen, CL ;
Fraga, CG ;
Oteiza, PI .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (12) :5041-5048
[37]  
Williamson G, 2005, AM J CLIN NUTR, V81, p243S, DOI 10.1093/ajcn/81.1.243S
[38]   Fractionation of apple procyanidins according to their degree of polymerization by normal-phase high-performance liquid chromatography [J].
Yanagida, A ;
Kanda, T ;
Takahashi, T ;
Kamimura, A ;
Hamazono, T ;
Honda, S .
JOURNAL OF CHROMATOGRAPHY A, 2000, 890 (02) :251-259
[39]   Separation of proanthocyanidins by degree of polymerization by means of size-exclusion chromatography and related techniques [J].
Yanagida, A ;
Shoji, T ;
Shibusawa, Y .
JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 2003, 56 (1-3) :311-322
[40]   Stabilizing effect of ascorbic acid on flavan-3-ols and dimeric procyanidins from cocoa [J].
Zhu, QY ;
Hammerstone, JF ;
Lazarus, SA ;
Schmitz, HH ;
Keen, CL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (03) :828-833