- Danilo Ercolini (1)
- Vincenzo Fogliano (2)
- V. Fogliano (1)
- L.W. Kroh (1)
- S.I.F.S. Martins (1)
- T. Oliviero (1)
- H.A. Schols (1)
- G. Smit (1)
- Hao Zhang (1)
- Hui Zhang (1)
Melanoidins from Coffee, Cocoa, and Bread Are Able to Scavenge α-Dicarbonyl Compounds under Simulated Physiological Conditions
Zhang, Hao ; Zhang, Hui ; Troise, Antonio Dario ; Fogliano, Vincenzo - \ 2019
Journal of Agricultural and Food Chemistry (2019). - ISSN 0021-8561 - p. 10921 - 10929.
coffee - dicarbonyls - Maillard reaction - melanoidins - polyphenols
Free amino residues react with α-dicarbonyl compounds (DCs) contributing to the formation of advanced glycation end products (AGEs). Phenolic compounds can scavenge DCs, thus controlling the dietary carbonyl load. This study showed that high-molecular weight cocoa melanoidins (HMW-COM), HMW bread melanoidins (HMW-BM), and especially HMW coffee melanoidins (HMW-CM) are effective DC scavengers. HMW-CM (1 mg/mL) scavenged more than 40% DCs within 2 h under simulated physiological conditions, suggesting some physiological relevance. Partial acid hydrolysis of HMW-CM decreased the dicarbonyl trapping capacity, demonstrating that the ability to react with glyoxal, methylglyoxal (MGO), and diacetyl was mainly because of polyphenols bound to macromolecules. Caffeic acid (CA) and 3-caffeoylquinic acid showed a DC-scavenging kinetic profile similar to that of HMW-CM, while mass spectrometry data confirmed that hydroxyalkylation and aromatic substitution reactions led to the formation of a stable adduct between CA and MGO. These findings corroborated the idea that antioxidant-rich indigestible materials could limit carbonyl stress and AGE formation across the gastrointestinal tract.
Food Design to Feed the Human Gut Microbiota
Ercolini, Danilo ; Fogliano, Vincenzo - \ 2018
Journal of Agricultural and Food Chemistry 66 (2018)15. - ISSN 0021-8561 - p. 3754 - 3758.
food ingredients - food processing - Mediterranean diet - melanoidins - metabolism - phytochemicals
The gut microbiome has an enormous impact on the life of the host, and the diet plays a fundamental role in shaping microbiome composition and function. The way food is processed is a key factor determining the amount and type of material reaching the gut bacteria and influencing their growth and the production of microbiota metabolites. In this perspective, the current possibilities to address food design toward a better feeding of gut microbiota are highlighted, together with a summary of the most interesting microbial metabolites that can be made from dietary precursors.
Influence of Roasting on the Antioxidant Activity and HMF Formation of a Cocoa Bean Model Systems
Oliviero, T. ; Capuano, E. ; Cämmerer, B. ; Fogliano, V. - \ 2009
Journal of Agricultural and Food Chemistry 57 (2009)1. - ISSN 0021-8561 - p. 147 - 152.
maillard reaction-products - coffee - glycosylation - melanoidins - components - capacity - glycine - lactose - xylose - color
During the roasting of cocoa beans chemical reactions lead to the formation of Maillard reaction (MR) products and to the degradation of catechin-containing compounds, which are very abundant in these seeds. To study the modifications occurring during thermal treatment of fat and antioxidant rich foods, such as cocoa, a dry model system was set up and roasted at 180 °C for different times. The role played in the formation of MR products and in the antioxidant activity of the system by proteins, catechin, and cocoa butter was investigated by varying the model system formulation. Results showed that the antioxidant activity decreased during roasting, paralleling catechin concentration, thus suggesting that this compound is mainly responsible for the antioxidant activity of roasted cocoa beans. Model system browning was significantly higher in the presence of catechin, which contributed to the formation of water-insoluble melanoidins, which are mainly responsible for browning. HMF concentration was higher in casein-containing systems, and its formation was strongly inhibited in the presence of catechin. No effects related to the degree of lipid oxidation could be observed. Data from model systems obtained by replacing fat with water showed a much lower rate of MR development and catechin degradation but the same inhibitory effect of catechin on HMF formation.
Electron Spin Resonance (ESR) Studies on the Formation of Roasting-Induced Antioxidative Structures in Coffee Brews at Different Degrees of Roast
Bekedam, E.K. ; Schols, H.A. ; Cämmerer, B. ; Kroh, L.W. ; Boekel, M.A.J.S. van; Smit, G. - \ 2008
Journal of Agricultural and Food Chemistry 56 (2008)12. - ISSN 0021-8561 - p. 4597 - 4604.
chemical-characterization - thermal-degradation - chlorogenic acids - model systems - melanoidins - capacity - foods - beverages - green
The antioxidative properties of coffee brew fractions were studied using electron spin resonance spectroscopy using 2,2,6,6-tetramethyl-1-piperidin-1-oxyl (TEMPO) and Fremy¿s salt (nitrosodisulfonate) as stabilized radicals. TEMPO was scavenged by antioxidants formed during roasting and not by chlorogenic acid, whereas Fremy¿s salt was scavenged by all antioxidants tested including chlorogenic acid. The stabilized radical TEMPO allowed the exclusive measurement of roasting-induced antioxidants. The roasting-induced antioxidant activity of coffee brews increased with increasing degree of roast, and most of these antioxidants were formed during the initial roasting stage. The majority of these roasting-induced antioxidants were present in the high molecular weight fractions, indicating that the formation of these antioxidants preferably occurs at specific high molecular weight structures, likely being arabinogalactan and/or protein moieties which might be part of the melanoidin complex. It was found that chlorogenic acids most probably do not lose their antioxidant activity and phenolic characteristics upon incorporation in coffee melanoidins. The parameter fast reacting antioxidants (FRA) was introduced as an alternative for the antioxidative potential. FRA levels showed that coffee fractions rich in roasting-induced antioxidants exposed their antioxidant activity relatively slowly, which must be a consequence of its complex structure. Finally, the melanoidin content and the roasting-induced antioxidant activity showed a positive and linear correlation for the coffee brew fractions, showing that roasting-induced antioxidants are present within melanoidins. This is the first time that the formation of roasting-induced antioxidants could be directly correlated with the extent of Maillard reaction and melanoidin formation in a complex product such as coffee.
A kinetic model for the glucose/glycine Maillard reaction pathways
Martins, S.I.F.S. ; Boekel, M.A.J.S. van - \ 2005
Food Chemistry 90 (2005)1-2. - ISSN 0308-8146 - p. 257 - 269.
n-(1-deoxy-d-fructos-1-yl)-glycine degradation pathways - casein systems - amadori compounds - glucose - reversibility - melanoidins - acrylamide - products - (glucose - aldoses
A comprehensive kinetic model for the glucose/glycine Maillard reaction is proposed based on an approach called multiresponse kinetic modelling. Special attention was paid to reactants, intermediates and end products: -fructose, N-(1-deoxy--fructos-1-yl)-glycine (DFG), 1-deoxy-2,3-hexodiulose and 3-deoxy-2-hexosulose, formic and acetic acid, methylglyoxal and 5-hydroxymethylfurfural (HMF). The organic acids were found to be stable end products, 3-deoxy-2-hexosulose was found to be involved in colour formation by reaction with glycine. It is suggested to consider acetic acid as an indicator of the progress of the Maillard reaction at pH 6.8. The significance of reversibility of formation of DFG was studied by kinetic model discrimination. The results suggested that the reaction path from DFG into its parents, glucose and glycine, is not important from a quantitative point of view, even though it does happen. The proposed model was updated and strained by varying one of the most important reaction conditions, the temperature. The estimated rate constants showed an Arrhenius type temperature dependence and the model performed well for all studied temperatures (80, 90, 100, 110 and 120 °C). Striking differences were found in temperature dependencies of the various reaction steps. More than just a fitting procedure, multiresponse modelling was shown to be a powerful tool in unravelling complicated reaction routes as occur in the Maillard reaction.