Posted 30 March 2008 - 02:49 AM
My recollection is that we determined that casein's proline groups bind only to polyphenols with a gallate group, like ECG and EGCG and oligomers of these catechins. Resveratrol should be safe.
J Agric Food Chem. 2002 Feb 27;50(5):1184-7.
Interactions between flavonoids and proteins: effect on the total antioxidant capacity.
Arts MJ, Haenen GR, Wilms LC, Beetstra SA, Heijnen CG, Voss HP, Bast A.
Department of Pharmacology and Toxicology, Faculty of Medicine, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The Netherlands. Mariken.Arts@farmaco.unimaas.nl
Flavonoids are potent antioxidants. It is also known that flavonoids bind to proteins. The effect of the interaction between tea flavonoids and proteins on the antioxidant capacity was examined. Their separate and combined antioxidant capacities were measured with the Trolox equivalent antioxidant capacity (TEAC) assay. It was observed that the antioxidant capacity of several components of green and black tea with alpha-, beta-, and kappa-casein or albumin is not additive; that is, a part of the total antioxidant capacity is masked by the interaction. This masking depends on both the protein and the flavonoid used. Components in green and black tea, which show the highest masking in combination with beta-casein, are epigallocatechin gallate and gallic acid. The results demonstrate that the matrix influences the efficacy of an antioxidant.
PMID: 11853501
J Food Sci. 2007 Apr;72(3):S230-3.
The effect of milk protein on the bioavailability of cocoa polyphenols.
Keogh JB, McInerney J, Clifton PM.
CSIRO Human Nutrition, PO Box 10041 Adelaide BC, South Australia 5000, Australia. jennifer.keogh@csiro.au
In order to determine whether milk proteins interact with cocoa polyphenols to modulate the uptake and concentration of polyphenols in plasma, 24 middle-aged men and women consumed 2 g of chocolate polyphenols, plus sugar and cocoa butter in 200 mL water, on 2 occasions. On 1 occasion, the chocolate mix contained 2.45 g of milk proteins. Blood samples were taken fasting and at regular intervals for 8 h. Catechin and epicatechins levels were measured in these samples and no differences were seen in average concentrations between the 2 treatments. Milk protein caused a slight increase in concentration at the early time points and a decrease at the later time points. In conclusion, milk powder did not influence the average concentration of polyphenols. While it slightly accelerated absorption, this is of no physiological significance.
PMID: 17995820
J Agric Food Chem. 2007 Oct 31;55(22):9235-40. Epub 2007 Sep 12.
Interactions between flavan-3-ols and poly(L-proline) studied by isothermal titration calorimetry: effect of the tannin structure.
Poncet-Legrand C, Gautier C, Cheynier V, Imberty A.
UMR1083 Sciences pour l'Knologie, INRA, Université Montpellier 1, France. celine.poncet@supagro.inra.fr
Interactions of proline-rich proteins (PRPs) with flavan-3-ols was studied using poly(L-proline) as a model protein by means of isothermal titration calorimetry (ITC). Several parameters were varied: (i) the galloylation and B-ring trihydroxylation of the flavan-3-ols (catechin, epicatechin, epicatechin gallate, and epigallocatechin gallate) and (ii) the degree of polymerization (monomers were compared to a mixture of oligomers with average degree of polymerization of 3.85). Large differences were observed between the flavan-3-ol monomers: no enthalpy change was measured when catechin and epicatechin were titrated by poly(L-proline), whereas thermodynamic parameters were determined in the case of galloylated monomers and mixture of oligomers. Stoichiometry ranged from 1 oligomer bound for each 12 proline units to 1 galloylated monomer for each 8 or 10 proline units. Association constants were in the range of 10(4)-10(5) M(-1), indicating a relatively high affinity of galloylated flavanols toward poly(L-proline), and the coexistence of both enthalpy- and entropy-driven phenomena was suggested. Finally, the binding of grape seed tannins to proteins was shown to be a cooperative process.
PMID: 17850090