Low Plasma Appearance of (+)-Catechin and (−)-Catechin Compared with Epicatechin after Consumption of Beverages Prepared from Nonalkalized or Alkalized Cocoa—A Randomized, Double-Blind Trial (original) (raw)
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The American journal of clinical nutrition, 2002
Epidemiologic studies have linked flavonoid-rich foods with a reduced risk of cardiovascular mortality. Some cocoas are flavonoid-rich and contain the monomeric flavanols (-)-epicatechin and (+)-catechin and oligomeric procyanidins formed from these monomeric units. Both the monomers and the oligomers have shown potential in favorably influencing cardiovascular health in in vitro and preliminary clinical studies. Although previous investigations have shown increasing concentrations of (-)-epicatechin in human plasma after cocoa consumption, no information is available in the published literature regarding the presence of procyanidins in human plasma. This study sought to determine whether procyanidins can be detected and quantified in human plasma after acute consumption of a flavanol-rich cocoa. Peripheral blood was obtained from 5 healthy adult subjects before (baseline, 0 h) and 0.5, 2, and 6 h after consumption of 0.375 g cocoa/kg body wt as a beverage. Plasma samples were analy...
The American Journal of Clinical Nutrition, 2002
Background: Epidemiologic studies have linked flavonoid-rich foods with a reduced risk of cardiovascular mortality. Some cocoas are flavonoid-rich and contain the monomeric flavanols (Ϫ)-epicatechin and (+)-catechin and oligomeric procyanidins formed from these monomeric units. Both the monomers and the oligomers have shown potential in favorably influencing cardiovascular health in in vitro and preliminary clinical studies. Although previous investigations have shown increasing concentrations of (Ϫ)-epicatechin in human plasma after cocoa consumption, no information is available in the published literature regarding the presence of procyanidins in human plasma. Objective: This study sought to determine whether procyanidins can be detected and quantified in human plasma after acute consumption of a flavanol-rich cocoa. Design: Peripheral blood was obtained from 5 healthy adult subjects before (baseline, 0 h) and 0.5, 2, and 6 h after consumption of 0.375 g cocoa/kg body wt as a beverage. Plasma samples were analyzed for monomers and procyanidins with the use of reversedphase HPLC with coulometric electrochemical array detection and liquid chromatography-tandem mass spectrometry. Results: Procyanidin dimer, (Ϫ)-epicatechin, and (+)-catechin were detected in the plasma of human subjects as early as 0.5 h (16 ± 5 nmol/L, 2.61 ± 0.46 mol/L, and 0.13 ± 0.03 mol/L, respectively) after acute cocoa consumption and reached maximal concentrations by 2 h (41 ± 4 nmol/L, 5.92 ± 0.60 mol/L, and 0.16 ± 0.03 mol/L, respectively). Conclusion: Dimeric procyanidins can be detected in human plasma as early as 30 min after the consumption of a flavanol-rich food such as cocoa.
Journal of Agricultural and Food Chemistry, 2007
Cocoa is a food rich in polyphenols, mainly the flavonoid procyanidins and flavan-3-ols. The improvement of the cardiovascular function in humans upon cocoa consumption has been specifically linked to the presence of flavan-3-ol derived metabolites in plasma, especially epicatechin glucuronide. In this context, a flavonoid-enriched cocoa-derived product could potentially exert stronger health benefits. The aim of the present study was to obtain a cocoa powder with a higher flavonoid content (mainly enriched in monomer compounds) and assess its flavonoid bioavailability in humans. For this purpose, an unfermented, nonroasted, and blanch-treated cocoa powder (A) was obtained. The powder contained four times more procyanidins than a conventional (B) cocoa powder. Powder A contained eight times more epicatechin and procyanidin B2 than powder B. Cocoa milk drinks were prepared with powder A (MDA) and B (MDB). The bioavailability of flavonoids in both drinks was assessed in a crossover intervention with healthy volunteers. The content of epicatechin glucuronide, the main metabolite detected in plasma, was five-fold higher upon consumption of MDA as compared with MDB. The urinary excretion of metabolites, mainly methyl epicatechin sulfate, was higher upon MDA consumption as compared with MDB, ranging from two-to 12-fold higher depending on the metabolite. These results, together with previous reports regarding the cardiovascular benefits linked to the presence of procyanidin metabolites in plasma, suggest that further clinical trials to validate the health benefits of a flavonoid-enriched cocoa powder are warranted.
Analytical and Bioanalytical Chemistry, 2010
Cocoa is well-known to be rich in flavan-3-ols. Previous analyses have established that alkaline treatment of cocoa beans results in epimerization of (−)-epicatechin to (−)-catechin and (+)-catechin to (+)-epicatechin. Now, the question is whether both epimers can be absorbed by the human organism. This paper describes sample preparation and an HPLC method for chiral determination of (+)/(−)catechin from sulfated and glucuronidated metabolites in human plasma. The sample preparation includes enzymatic hydrolysis of the catechin metabolites, and solid-phase extraction (SPE). A PM-γ-cyclodextrin column is used with a coulometric electrode-array detection (CEAD) system. The recovery of catechin ranges from 89.9 to 96.8%. The limit of detection is 5.9 ng mL −1 for (−)-catechin and 6.8 ng mL −1 for (+)-catechin, and the limit of quantification is 12.8 ng mL −1 for (−)-catechin and 16.9 ng mL −1 for (+)catechin. The relative standard deviation of the method ranges from 0.9 to 1.5%. This method was successfully applied to human plasma after consumption of a cocoa drink. In one human self-experiment, (+)-catechin and (−)catechin were found in human plasma, but metabolism of the two enantiomers differed. Keywords Flavanols. Cocoa. Chiral. Human plasma. Electrochemical detection. HPLC Benno F. Zimmermann was involved in the development of the SPE sample preparation.
Molecular Nutrition & Food Research, 2013
Cocoa is an important source of polyphenols, which comprise 12-18% of its total dry weight. The major phenolic compounds in cocoa and cocoa products are mainly flavonoids such as epicatechin, catechin, and proanthocyanidins. These products contain higher amounts of flavonoids than other polyphenol-rich foods. However, the bioavailability of these compounds depends on other food constituents and their interactions with the food matrix. Many epidemiological and clinical intervention trials have concluded that the ingestion of flavonoids reduces the risk factors of developing cardiovascular disease. This review summarizes the new findings regarding the effects of cocoa and chocolate consumption on cardiovascular risk factors. The mechanisms involved in the cardioprotective effects of cocoa flavonoids include reduction of oxidative stress, inhibition of low-density lipoproteins oxidation and platelet aggregation, vasodilatation of blood vessels, inhibition of the adherence of monocytes to vascular endothelium, promotion of fibrinolysis, and immunomodulatory and anti-inflammatory activity. Scientific evidence supports a cause and effect relationship between consumption of cocoa flavonoids and the maintenance of normal endothelium-dependent vasodilation, which contributes to normal blood flow. However, larger randomized trials are required to definitively establish the impact of cocoa and cocoa products consumption on hard cardiovascular outcomes.
Journal of Agricultural and Food Chemistry, 2010
The impact of carbohydrates and milk on the bioavailability of catechin (C) and epicatechin (EC) from chocolate has been previously studied. However, little data exists regarding potential modulation of the phase-II metabolism by these chocolate matrix factors. The objectives of this study were to assess the impact of matrix composition on qualitative and quantitative profiles of circulating catechins and their metabolites following administration of commercially relevant chocolate confections. Sprague-Dawley rats were fed 1.5 g of a confection (reference dark, high sucrose, or milk chocolate) by intragastric gavage, and plasma samples were collected over 8 h. HPLC-MS analysis was performed to quantify C, EC and their metabolites. The predominant metabolites were O-glucuronides (2 metabolites), and O-Me-O-glucuronides (3 metabolites). Plasma concentrations of metabolites were generally the highest for high sucrose treatment and lowest for milk treatment, while reference dark treatment generally resulted in intermediate concentrations. The O-Me-(±)-C/ EC-O-β-glucuronide (peak 4) was significantly higher for the high sucrose treatment (2325 nM*h) versus the milk treatment (1300 nM*h). Additionally, C MAX values for (±)-C/EC-O-β-glucuronide (peak 3), and two O-Me-(±)-C/EC-O-β-glucuronides (peaks 4 and 6) were significantly higher for high sucrose treatment (4012, 518, and 2518 nM, respectively) versus the milk treatment (2590, 240, and 1670 nM, respectively). Milk and sucrose appear to modulate both metabolism and plasma pharmacokinetics, and to a lesser extent, the overall bioavailability of catechins from chocolate confections.
Nutrients, 2019
Cocoa is continuously drawing attention due to growing scientific evidence suggesting its effects on health. Flavanols and methylxanthines are some of the most important bioactive compounds present in cocoa. Other important bioactives, such as phenolic acids and lactones, are derived from microbial metabolism. The identification of the metabolites produced after cocoa intake is a first step to understand the overall effect on human health. In general, after cocoa intake, methylxanthines show high absorption and elimination efficiencies. Catechins are transformed mainly into sulfate and glucuronide conjugates. Metabolism of procyanidins is highly influenced by the polymerization degree, which hinders their absorption. The polymerization degree over three units leads to biotransformation by the colonic microbiota, resulting in valerolactones and phenolic acids, with higher excretion times. Long term intervention studies, as well as untargeted metabolomic approaches, are scarce. Contra...
Food effects on the absorption and pharmacokinetics of cocoa flavanols
Life Sciences, 2003
Macronutrients in food and gastric acid are known to have a pronounced effect on the metabolism of many xenobiotics, an effect that impacts their efficacy as bioactive agents. In this investigation we assessed the impact of select food treatments and the histamine H(2)-receptor antagonist Famotidine (Pepcid-AC) on flavanol absorption and metabolism. Four crossover intervention studies were conducted with 6 subjects each. Volunteers consumed sugar-free, flavanol-rich cocoa (0.125 g/kg body wt) alone, with macronutrient-rich foods (8.75 or 17.5 kJ/kg subject body wt) or Famotidine (Pepcid-AC). Blood samples were drawn at 5 time points including baseline. Plasma samples were analyzed for epicatechin and catechin flavanols by HPLC. Pharmacokinetic parameters were assessed using non-compartmental methodology. When provided at 17.5 kJ/kg subject body weight (approximately 4 kcal/kg), sugar and bread test meals increased flavanol area under the curve (AUC) values to 140% of control values (P < 0.05). A corresponding tendency for plasma antioxidant capacity to increase was observed for the cocoa treatment at 1.5 and 2.5 h (P < 0.17, P < 0.06, respectively). The ability of treatment meals to affect AUC values was positively correlated with treatment carbohydrate content (r = 0.83; P< 0.02). In contrast to carbohydrate rich meals, lipid and protein rich meals and Famotidine treatment had minimal effects on flavanol absorption. Based on C(max) and AUC values, this data suggests that the uptake of flavanols can be increased significantly by concurrent carbohydrate consumption.