Procyanidin dimer B2 [epicatechin-(4β-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa

Holt, Roberta R.; Lazarus, Sheryl A.; Sullards, M. Cameron; Zhu, Qin; Schramm, Derek D.; Hammerstone, John F.; Fraga, César G.; Schmitz, Harold H.; Keen, Carl L.

doi:10.1093/ajcn/76.4.798

Cited by 479 publications

(307 citation statements)

References 41 publications

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“…Since only flavonol monomers and dimeric proanthocyanidins are absorbed [58][59][60][61], systemic effects of proanthocyanidins would be limited to these compounds or eventually to not yet characterized metabolites and/or colonic degradation products from the polymeric molecules [58]. In this context, our findings cannot help to rationalize the cardiovascular protection nor provide a molecular interpretation for the anti-inflammatory effects of pistachio nut diets [20].…”

Section: Conclusive Remarksmentioning

confidence: 89%

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

et al. 2011

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Background Positive effects of pistachio nut consumption on plasma inflammatory biomarkers have been described; however, little is known about molecular events associated with these effects. Purpose We studied the anti-inflammatory activity of a hydrophilic extract from Sicilian Pistacia L. (HPE) in a macrophage model and investigated bioactive components relevant to the observed effects. Methods HPE oligomer/polymer proanthocyanidin fractions were isolated by adsorbance chromatography, and components quantified as anthocyanidins after acidic hydrolysis. Isoflavones were measured by gradient elution HPLC analysis. RAW 264.7 murine macrophages were pre-incubated with either HPE (1-to 20-mg fresh nut equivalents) or its isolated components for 1 h, then washed before stimulating with lipopolysaccharide (LPS) for 24 h. Cell viability and parameters associated with Nuclear Factor-jB (NF-jB) activation were assayed according to established methods including ELISA, Western blot, or cytofluorimetric analysis. Results HPE suppressed nitric oxide (NO) and tumor necrosis factor-a (TNF-a) production and inducible NO-synthase levels dose dependently, whereas inhibited prostaglandin E 2 (PGE 2 ) release and decreased cyclooxygenase-2 content, the lower the HPE amount the higher the effect. Cytotoxic effects were not observed. HPE also caused a dose-dependent decrease in intracellular reactive oxygen species and interfered with the NF-jB activation.Polymeric proanthocyanidins, but not isoflavones, at a concentration comparable with their content in HPE, inhibited NO, PGE 2 , and TNF-a formation, as well as activation of IjB-a. Oligomeric proanthocyanidins showed only minor effects. Conclusions Our results provide molecular evidence of anti-inflammatory activity of pistachio nut and indicate polymeric proanthocyanidins as the bioactive components. The mechanism may involve the redox-sensitive transcription factor NF-jB. Potential effects associated with pistachio nut consumption are discussed in terms of the proanthocyanidin bioavailability.

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Section: Conclusive Remarksmentioning

confidence: 89%

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

et al. 2011

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“…It is known that their bioavailability is low owing to their high molecular weight (Déprez et al, 2001;Donovan et al, 2002;Gonthier et al, 2003). Only procyanidin dimers have been detected in human plasma, but at very low concentrations (Holt et al, 2002). Their poor bioavailability does not exclude systemic effects.…”

Section: Polyphenol-rich Apple and Endothelial Function S Auclair Et Almentioning

confidence: 99%

The regular consumption of a polyphenol-rich apple does not influence endothelial function: a randomised double-blind trial in hypercholesterolemic adults

et al. 2010

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Background/objectives: Epidemiological studies suggest that apple consumption is associated with a reduction in cardiovascular disease risk. Apple polyphenols may contribute to explain these effects. Endothelial dysfunction has been associated with early stage of atherosclerosis and polyphenols from various dietary sources have been shown to reverse it. The aim of the present study was to investigate the effect of the consumption of a polyphenol-rich apple on endothelial function. Subjects/methods: In all, 30 hypercholesterolemic volunteers were included in a double-blind, randomized crossover trial. They successively consumed 40 g of two lyophilized apples, polyphenol-rich and polyphenol-poor, providing respectively 1.43 and 0.21 g polyphenols per day during two 4-week periods separated by a 4-week washout period. Results: Brachial artery flow-mediated vasodilation (FMD) was assessed at the beginning and at the end of each intervention period. FMD did not differ between the polyphenol-rich and the polyphenol-poor apples, neither did the other cardiovascular disease risk factors (plasma lipids, homocysteine, antioxidant capacity). Conclusions: These data suggest that over a 4-week period, the consumption of a polyphenol-rich apple does not improve vascular function in hypercholesterolemic patients.

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“…50) Monomers are easily absorbed; in this respect, epicatechin is more efficient than catechin. 51) While only small amounts of procyanidin dimer are absorbed directly by humans, 52,53) it can be digested into the monomer form before being absorbed. 54) As compared with the other dietary procyanidins, such as those from grape, apple, and cocoa, our results show that the procyanidins present in Chinese hawthorn fruits have lower mDP values and are composed mainly of epicatechin.…”

Section: Protease Inhibitory Activitiesmentioning

confidence: 99%

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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Hawthorn polyphenol (HP) was prepared by ethyl acetate treatment of the ethanol extract (HE) of Chinese hawthorn fruit. The concentrations of 15 polyphenols in the HP, HE, extraction residue (HJ), and a hawthorn leaf extract (HF) were determined by HPLC. For HP, the total content of the 15 polyphenols was 21.4%, comprised of 19.7% of procyanidins, 1.21% of chlorogenic acid, and 0.48% of flavonoids, compared to 2.55% for the HE. The yields of procyanidin monomer, dimer, trimer, tetramer, and pentamer were 50.5%, 30.3%, 23.0%, 14.6%, and 12.5% respectively, and the mean degree of polymerization was reduced to 1.39 (HP) from 1.65 (HE). Seven different physiological actions of the four extracts were investigated. The HP showed strong O 2 À and OH scavenging capacities (IC 50 values of 6.3 g/ml and 1.1 g/ml respectively), as well as selective prolyl endopeptidase inhibition (IC 50 of 60 g/ml). The active constituents appeared to be procyanidins.Key words: Crataegus pinnatifida; HPLC; procyanidin; antioxidant; free radicalsIn Europe, standardized extracts of the leaves and flowers of Crataegus oxyacantha and Crataegus monogyna are used in the therapy for moderate (NYHA II) congestive heart failure. 1,2) These extracts exert several pharmacological and clinical effects, such as antiischemia/reperfusion-injury, anti-arrhythmic, hypolipidemic, and hypotensive effects. 1,2) Flavonoids and procyanidins are considered to be the two main active constituents. 2) Species of Chinese hawthorn, particularly Crataegus pinnatifida and Crataegus pinnatifida Bge. var. major NE Br., have also been used as herbal medicines. 2,3) Studies indicate that Chinese hawthorn extracts have beneficial effects, such as antioxidant, 4,5) anti-inflammatory, 6) and hypolipidemic effects, 7) as well as protective effects on the brain and vascular endothelium 8,9) and endothelium-dependent relaxation. 10) Recently, we analyzed 37 major cultivars of Chinese hawthorn using high performance liquid chromatography (HPLC), and found that procyanidins, which were present in high concentrations, were the main phenolic active constituents in these fruits. 11) In general, the hawthorn found in China is an edible fruit that is popular for its special acidic taste. It is bigger than its European counterpart. Since the content of organic acid in Chinese hawthorn fruits can be up to 5% (fresh weight), they are used to produce various foods, such as jams, jellies, juices, tinned foods, wines, and various sweet foods. However, the high sugar content of these fruits counteracts the benefits of polyphenols for consumers of advanced age or for those who suffer from hypertension, cardiovascular disease, or diabetes. Hence, it is desirable to separate the polyphenol and sugar components. Previously, hawthorn extract (HE) for medical applications were ethanol-extracted from the dried fruit of the Chinese hawthorn. 12) These crude extracts contain many undesirable substances, such as carbohydrates, organic acids, and moisture, which not only reduce the concentration of acti...

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Procyanidin dimer B2 [epicatechin-(4β-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa

Abstract: Dimeric procyanidins can be detected in human plasma as early as 30 min after the consumption of a flavanol-rich food such as cocoa.

Cited by 479 publications

References 41 publications

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells

The regular consumption of a polyphenol-rich apple does not influence endothelial function: a randomised double-blind trial in hypercholesterolemic adults

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

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