Article

Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa

Sandra V. VerstraetenIQUIFIB-Department of Biological Chemistry (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Mars Incorporated, Hackettstown, New Jersey 07840, USA, and Department of Nutrition, University of California, One Shields Avenue, Davis, California 95616, USA, and Physical Chemistry-PRALIB, (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Department ofJohn F. HammerstoneIQUIFIB-Department of Biological Chemistry (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Mars Incorporated, Hackettstown, New Jersey 07840, USA, and Department of Nutrition, University of California, One Shields Avenue, Davis, California 95616, USA, and Physical Chemistry-PRALIB, (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Department ofCarl L. KeenIQUIFIB-Department of Biological Chemistry (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Mars Incorporated, Hackettstown, New Jersey 07840, USA, and Department of Nutrition, University of California, One Shields Avenue, Davis, California 95616, USA, and Physical Chemistry-PRALIB, (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Department ofCésar G. FragaIQUIFIB-Department of Biological Chemistry (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Mars Incorporated, Hackettstown, New Jersey 07840, USA, and Department of Nutrition, University of California, One Shields Avenue, Davis, California 95616, USA, and Physical Chemistry-PRALIB, (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Department ofPatricia I. OteizaIQUIFIB-Department of Biological Chemistry (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Mars Incorporated, Hackettstown, New Jersey 07840, USA, and Department of Nutrition, University of California, One Shields Avenue, Davis, California 95616, USA, and Physical Chemistry-PRALIB, (UBA-CONICET), School of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113-Buenos Aires, Argentina, and Department of

2005en

ABI

Abstract

The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33-5 microM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water-lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer.

Identifiers

DOI: 10.1021/jf058018m

Citations and references

Cited by 20 references

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