Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled

Francene M. Steinberg, Roberta R. Holt, Harold H. Schmitz, Carl L Keen

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Cocoa flavan-3-ols (catechin, epicatechin and oligomeric procyanidins) were tested for their ability to decrease LDL oxidative susceptibility and spare α-tocopherol (α-toc) in vitro. Physiologic concentration (0.10-0.50 μM) of flavanols were used. The flavanols increased LDL conjugated diene lag times dose-dependently from 23-207% and 15-143% in response to copper and AAPH oxidation, respectively, and delayed α-toc consumption. Sparing of LDL α-toc represents a possible mechanism for flavanols to enhance the resistance of plasma and LDL to oxidative stress. Procyanidins decreased LDL oxidative susceptibility with increasing chain length. However, when based on equivalent amounts of monomeric units, they inhibited LDL oxidation to a similar extent. This suggests that antioxidant activity of procyanidins with biologic substrates is not attributable to chain length or charge delocalization through polymeric linkages, but primarily to ring structures and catechol groups. Additionally, human plasma was analyzed for the presence of oligomeric procyanidins following consumption of a flavanol-rich cocoa product. Procyanidin dimers were detected in plasma concordant with the appearance of monomeric flavanols, with a peak of 0.08 ± 0.01 μmol/L (n = 6) at two hours after consumption. Thus, this paper confirms the occurrence of procyanidins in human plasma, and extends previous structure-function observations regarding flavanoid protection of LDL.

Original languageEnglish (US)
Pages (from-to)645-652
Number of pages8
JournalJournal of Nutritional Biochemistry
Volume13
Issue number11
DOIs
StatePublished - Nov 1 2002

Fingerprint

Cocoa
Chain length
Proanthocyanidins
Monomers
Oxidation
Plasma (human)
Catechin
Plasmas
Oxidative stress
Tocopherols
oxidized low density lipoprotein
procyanidin
Dimers
Copper
Oxidative Stress
Antioxidants
Substrates

Keywords

  • Alpha-tocopherol
  • Cocoa
  • Flavanol
  • LDL
  • Oxidation
  • Procyanidin

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology, Diabetes and Metabolism

Cite this

Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled. / Steinberg, Francene M.; Holt, Roberta R.; Schmitz, Harold H.; Keen, Carl L.

In: Journal of Nutritional Biochemistry, Vol. 13, No. 11, 01.11.2002, p. 645-652.

Research output: Contribution to journalArticle

Steinberg, Francene M. ; Holt, Roberta R. ; Schmitz, Harold H. ; Keen, Carl L. / Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled. In: Journal of Nutritional Biochemistry. 2002 ; Vol. 13, No. 11. pp. 645-652.
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AU - Holt, Roberta R.

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N2 - Cocoa flavan-3-ols (catechin, epicatechin and oligomeric procyanidins) were tested for their ability to decrease LDL oxidative susceptibility and spare α-tocopherol (α-toc) in vitro. Physiologic concentration (0.10-0.50 μM) of flavanols were used. The flavanols increased LDL conjugated diene lag times dose-dependently from 23-207% and 15-143% in response to copper and AAPH oxidation, respectively, and delayed α-toc consumption. Sparing of LDL α-toc represents a possible mechanism for flavanols to enhance the resistance of plasma and LDL to oxidative stress. Procyanidins decreased LDL oxidative susceptibility with increasing chain length. However, when based on equivalent amounts of monomeric units, they inhibited LDL oxidation to a similar extent. This suggests that antioxidant activity of procyanidins with biologic substrates is not attributable to chain length or charge delocalization through polymeric linkages, but primarily to ring structures and catechol groups. Additionally, human plasma was analyzed for the presence of oligomeric procyanidins following consumption of a flavanol-rich cocoa product. Procyanidin dimers were detected in plasma concordant with the appearance of monomeric flavanols, with a peak of 0.08 ± 0.01 μmol/L (n = 6) at two hours after consumption. Thus, this paper confirms the occurrence of procyanidins in human plasma, and extends previous structure-function observations regarding flavanoid protection of LDL.

AB - Cocoa flavan-3-ols (catechin, epicatechin and oligomeric procyanidins) were tested for their ability to decrease LDL oxidative susceptibility and spare α-tocopherol (α-toc) in vitro. Physiologic concentration (0.10-0.50 μM) of flavanols were used. The flavanols increased LDL conjugated diene lag times dose-dependently from 23-207% and 15-143% in response to copper and AAPH oxidation, respectively, and delayed α-toc consumption. Sparing of LDL α-toc represents a possible mechanism for flavanols to enhance the resistance of plasma and LDL to oxidative stress. Procyanidins decreased LDL oxidative susceptibility with increasing chain length. However, when based on equivalent amounts of monomeric units, they inhibited LDL oxidation to a similar extent. This suggests that antioxidant activity of procyanidins with biologic substrates is not attributable to chain length or charge delocalization through polymeric linkages, but primarily to ring structures and catechol groups. Additionally, human plasma was analyzed for the presence of oligomeric procyanidins following consumption of a flavanol-rich cocoa product. Procyanidin dimers were detected in plasma concordant with the appearance of monomeric flavanols, with a peak of 0.08 ± 0.01 μmol/L (n = 6) at two hours after consumption. Thus, this paper confirms the occurrence of procyanidins in human plasma, and extends previous structure-function observations regarding flavanoid protection of LDL.

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