Adriana Farah

Influence of coffee roasting on the incorporation of phenolic compounds into melanoidins and their relationship with antioxidant activity of the brew.

In the present study, the influence of coffee roasting on free and melanoidin-bound phenolic compounds and their relationship with the brews antioxidant activity (AA), evaluated by TRAP, TEAC, and TRAP, were investigated. Changes in the relative content of free chlorogenic acids (CGA), free lactones, and melanoidin-bound phenolic acids during roasting indicate that phenolic compounds were incorporated into melanoidins mainly at early stages of the process, being thereafter partly oxidized to dihydrocaffeic acid, and degraded. Although less than 1% of CGA in green coffee was incorporated into melanoidins during roasting, the relative content of melanoidin-bound phenolic acids increased significantly during this process, reaching up to 29% of total phenolic compounds in brews from dark roasted coffees. Regardless of the AA assay used and considering all roasting degrees, the overall contribution of CGA to the AA of the whole brews was higher than that of melanoidin-bound phenolic compounds. It was estimated that the latter compounds contributed to 25-47% of the AA, depending on the assay used.

Effect of Simultaneous Consumption of Milk and Coffee on Chlorogenic Acids’ Bioavailability in Humans

Different studies have shown that milk may interact with polyphenols and affect their bioavailability in humans. The present study investigated the effect of the simultaneous consumption of coffee and milk on the urinary excretion of chlorogenic acids (CGA) and metabolites. Subjects were submitted to consumption of water, instant coffee (609 mmol of CGA) dissolved in water, and instant coffee dissolved in whole milk. Urine was collected for 24 h after consumption of each treatment for analysis of CGA and metabolites by HPLC/LC-MS. The amount of CGA and metabolites recovered after consumption of combined coffee-milk (40% ± 27%) was consistently lower in all subjects compared to that of coffee alone (68% ± 20%). Concluding, the simultaneous consumption of milk and coffee may impair the bioavailability of coffee CGA in humans.

Modeling Weight Loss and Chlorogenic Acids Content in Coffee during Roasting

Roasting is a key step in the production of a high-quality coffee. Roasting degree is directly related to coffee chemical composition and may be determined objectively by weight loss after roasting. Chlorogenic acids (CGA) are thermally labile phenolic compounds that play an important role in the final cup quality and health benefits of coffee. Considering the interest in finding a reliable method to predict weight loss and CGA content in coffee, models have been developed to estimate these parameters during roasting. Weight loss was successfully modeled (r = 0.99) independent of the instant temperature. CGA degradation followed first-order Arrhenius-compliant kinetic models with good predictability (r = 0.98), especially for light to moderately dark samples. In both cases distinct models for Coffea arabica and Coffea canephora were calculated, because of differences in chemical composition and cell wall structure between these species. The proposed models may become important predictive tools in the coffee industry.

Effects of chronic coffee consumption on glucose kinetics in the conscious rat

Epidemiological studies indicate that regular coffee consumption reduces the risk of developing type 2 diabetes. Despite these findings, the biological mechanisms by which coffee consumption exerts these effects are unknown. The aim of this study was twofold: to develop a rat model that would further delineate the effects of regular coffee consumption on glucose kinetics, and to determine whether coffee, with or without caffeine, alters the actions of insulin on glucose kinetics in vivo. Male Sprague-Dawley rats were fed a high-fat diet for 4 weeks in combination with one of the following: (i) drinking water as placebo (PL), (ii) decaffeinated coffee (2 g/100 mL) (DC), or (iii) alkaloid caffeine (20 mg/100 mL) added to decaffeinated coffee (2 g/100 mL) (CAF). Catheters were chronically implanted in a carotid artery and jugular vein for sampling and infusions, respectively. Recovered animals (5 days postoperative) were fasted for 5 h before hyperinsulinemic-euglycemic clamps (2 mU x kg(-1) x min(-1)). Glucose was clamped at 6 mmol/L and isotopes (2-deoxy-[(14)C]glucose and [3-(3)H]glucose) were administered to obtain indices of whole-body and tissue-specific glucose kinetics. Glucose infusion rates and measures of whole-body metabolic clearance were greater in DC than in PL or CAF, indicating increased whole-body insulin sensitivity. As the only difference between DC and CAF was the addition of alkaloid caffeine, it can be concluded that caffeine antagonizes the beneficial effects of DC. Given these findings, decaffeinated coffee may represent a nutritional means of combating insulin resistance.

4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice

RationaleCinnamoylquinides are formed from the corresponding chlorogenic acids during coffee roasting. Instant coffee has been shown to displace binding of the mu opioid receptor antagonist, [3H]naloxone, but the putative active agent, feruloylquinide, has not been characterized.ObjectivesThe goal was to identify the active agent(s) in coffee by measuring the binding affinity of individual cinnamoyl-1,5-quinides to the human mu opioid receptor, and determine the effects of these compounds on morphine-induced anti-nociceptive behavior in mice.MethodsCinnamoyl-1,5-quinides in extracts of decaffeinated instant coffee were quantified by reverse-phase HPLC comparisons with synthetic samples of 3-coumaroyl-1,5-quinide and 4-coumaroyl-1,5-quinide, 3-caffeoyl-1,5-quinide and 4-caffeoyl-1,5-quinide (4-CQL) 3-feruloyl-1,5-quinide and 4-feruloyl-1,5-quinides and 3,4-dicaffeoyl-1,5-quinide (DICAQ). Affinities of the cinnamoyl-1,5-quinides and decaffeinated instant coffee extract were determined by displacement of [3H]naloxone binding in cultured HEK-MOR cells. Inhibition of the anti-nociceptive activity of morphine (1xa0mg/kg IP) was determined in C57BL/6J mice using the hot plate test at 52°C.ResultsExtract of decaffeinated instant coffee produced a displacement Ki of 42±16xa0mg/l, while the Ki of a synthetic sample of 4-CQL was 4.4±0.4xa0μM. Compounds with a cinnamoyl substituent in the 4-position of the quinide, i.e. 4-CQL, DICAQ, 3,4-diferuloyl-1,5-quinide, and 3,4-dicoumaroyl-1,5-quinide, had affinities for the mu opioid receptor in the low micromolar range. In the hot plate test, coffee extract, containing 0.78% of 4-CQL, reversed the anti-nociceptive effect of morphine at 10xa0mg/kg IP. Two cinnamoyl-1,5-quinides found in roasted coffee, DICAQ, and 4-CQL, were active at 1 and 0.1xa0mg/kg IP, respectively.ConclusionsThese results suggest that the previously reported anti-opioid activity of instant coffee is caused primarily by the presence of 4-CQL, and to lesser extent by other cinnamoyl-1,5-quinides.

Distribution of Major Chlorogenic Acids and Related Compounds in Brazilian Green and Toasted Ilex paraguariensis (Maté) Leaves

Ilex paraguariensis (maté) is one of the best sources of chlorogenic acids (CGA) in nature. When leaves are toasted, some isomers are partly transformed into 1,5-γ-quinolactones (CGL). Both CGA and CGL are important contributors to the brews flavor and are thought to contribute to human health. In this study, we quantified 9 CGA, 2 CGL, and caffeic acid in 20 samples of dried green and toasted maté that are commercially available in Brazil. Total CGA content in green maté varied from 8.7 to 13.2 g/100 g, dry weight (dw). Caffeic acid content varied from 10.8 to 13.5 mg/100 g dw, respectively. Content in toasted maté varied from 1.5 to 4.6 g/100 g and from 1.5 to 7.2 mg/100 g dw, respectively. Overall, caffeoylquinic acid isomers (CQA) were the most abundant CGA in both green and toasted maté, followed by dicaffeoylquinic acids (diCQA) and feruloylquinic acids (FQA). These classes accounted for 58.5%, 40.0%, and 1.5% of CGA, respectively, in green maté and 76.3%, 20.7%, and 3.0%, respectively, in toasted maté. Average contents of 3-caffeoylquinolactone (3-CQL) and 4-caffeoylquinolactone (4-CQL) in commercial toasted samples were 101.5 mg/100 g and 61.8 mg/100 g dw, respectively. These results show that, despite overall losses during the toasting process, CGA concentrations are still substantial in toasted leaves, compared to other food sources of CGA and phenolic compounds in general. In addition to evaluating commercial samples, investigation of changes in CGA profile and formation of 1,5-γ-quinolactones was performed in experimental maté toasting.

Chapter 7:Analysis of Caffeine by Liquid Chromatography-Mass Spectrometry

Caffeine, 1,3,7-trimethyl-xanthine, is a purine-based xanthine alkaloid (Figureu20057.1). Caffeine was first isolated from coffee in 1820 by the German chemist Friedlieb Ferdinand Runge and in 1821 by a team of French chemists, Robiquet, Pelletier and Caventou. Pelletier first conceived the word “cafein...