Polyphenols with Antiglycation Activity and Mechanisms of Action: a Review of Recent findings
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journal of food and drug analysis xxx (2016) 1e9 Available online at www.sciencedirect.com ScienceDirect journal homepage: www.jfda-online.com Review Article Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings * Wan-Ju Yeh a,1, Shih-Min Hsia a,1, Wei-Hwa Lee b,1, Chi-Hao Wu a,c, a School of Nutrition and Health Sciences, College of Nutrition, Taipei Medical University, Taipei, Taiwan b Department of Pathology, Taipei Medical University-Shuang Ho Hospital, Taipei, Taiwan c Nutrition Research Centre, Taipei Medical University Hospital, Taipei, Taiwan article info abstract Article history: Advanced glycation end products (AGEs) are substances composed of amino groups of Received 23 September 2016 proteins and reducing sugars. The initial and propagation phases of the glycation process Received in revised form are accompanied by the production of a large amount of free radicals, carbonyl species, and 6 October 2016 reactive dicarbonyl species, of which, methylglyoxal (MG) is the most reactive and can Accepted 12 October 2016 cause dicarbonyl stress, influencing normal physiological functions. In the advanced Available online xxx phase, the production of AGEs and the interaction between AGEs and their receptor, RAGE, are also considered to be among the causes of chronic diseases, oxidative stress, and in- Keywords: flammatory reaction. Till date, multiple physiological activities of polyphenols have been advanced glycation end products confirmed. Recently, there have been many studies discussing the ability of polyphenols to antiglycation suppress the MG and AGEs formation, which was also confirmed in some in vivo studies. flavonoid This review article collects recent literatures concerning the effects of polyphenols on the phenolic acid generation of MG and AGEs through different pathways and discusses the feasibility of the polyphenols inhibition of glycative stress and dicarbonyl stress by polyphenols. Copyright © 2016, Food and Drug Administration, Taiwan. Published by Elsevier Taiwan LLC. This is an open access article under the CC BY-NC-ND license (http:// creativecommons.org/licenses/by-nc-nd/4.0/). food have been confirmed to cause many chronic diseases in 1. Introduction organisms, including diabetes mellitus (DM) [2] and kidney diseases [3], and are among the causes of the development The spontaneous post-translational modification of proteins and malignancy of tumors [4]. Therefore, there have already or amino acids through reducing sugars is called the Maillard been many studies investigating various factors in the appli- reaction or nonenzymatic glycation, and the products result- cation of the Maillard reaction in food chemistry, physiology, ing after the exposure to reducing sugars are called as and toxicology. advanced glycation end products (AGEs) [1]. In the course of The production of dicarbonyl compounds during the food processing, heating, and storage, the Maillard reaction Maillard reaction is an important step in the production of can enhance food flavor and color; however, excessive AGEs in AGEs [5], among which methylglyoxal (MG) is one of the * Corresponding author. 250 Wuxing Street, Taipei City 110, Taiwan. E-mail address: [email protected] (C.-H. Wu). 1 These authors contribute equally to this work. http://dx.doi.org/10.1016/j.jfda.2016.10.017 1021-9498/Copyright © 2016, Food and Drug Administration, Taiwan. Published by Elsevier Taiwan LLC. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). Please cite this article in press as: Yeh W-J, et al., Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings, Journal of Food and Drug Analysis (2016), http://dx.doi.org/10.1016/j.jfda.2016.10.017 2 journal of food and drug analysis xxx (2016) 1e9 most highly reactive carbonyl species (RCS) in the human body [6]. In addition to investigating the effects of AGEs, recent studies have also addressed the effects of MG on many chronic diseases and aging-related diseases in clinical practice [7]. The MG concentration in the blood of DM pa- tients is reported to be significantly higher than that in non- DM patients, reaching 400mM [8]. Additionally, endogenous MG is produced in the bodies of organisms. Under patho- logical conditions, an even higher concentration of MG will be accumulated in the body, which might be associated with the imbalance of the antiglycation system, known as the glyoxalase system [9]. Therefore, the accumulation of RCS, such as MG, in organisms and the associated metabolic imbalance will result in the development of many human diseases. Recently, antiglycation has been considered as an effective strategy to slow down human aging and disease development. The inhibition of glycation can suppress inflammasome acti- vation to reduce the development of inflammatory reactions [3,10]. The antioxidant and anti-inflammation abilities of polyphenol substances have been extensively studied, and their antiglycation functions have been screened in many e in vitro experimental platforms. The results show that poly- Figure 1 Pathway for AGE formation. The N-terminal phenols can inhibit the biosynthesis of AGEs through their amino groups of protein and reducing sugar form antioxidant properties, metal-chelating ability, protein inter- dicarbonyls including methylglyoxal, glyoxal, and 3- action, MG trapping, and/or blocking the receptor for deoxyglucosone through polyol pathway, glycolysis, or advanced glycation end products (RAGE) [11,12]. Polyphenols autoxidation of reducing sugar, leading to generation of ¼ were classified into four large groups in this article, phenolic pathological AGEs. AGE advanced glycation end product; ¼ -3 ¼ 3 acids, stilbenes, lignans, and flavonoids, and different anti- CEL N carboxyethyllysine; CML N -carboxymethyl- ¼ ¼ glycation functions of polyphenols found in recent years were lysine; 3-dG 3-deoxyglucosone; DOLD 3- ¼ examined to evaluate the antiglycation potential of deoxyglucosone lysine dimer; GO glyoxal; ¼ ¼ polyphenols. GOLD glyoxal-lysine dimer; MG methylglyoxal; MG- H ¼ MG-derived-hydroimidazalone; MOLD ¼ methylglyoxal-lysine dimer. 2. AGEs formation The Maillard reaction is a nonenzymatic glycation function. It involves many steps, and the reaction usually requires several 2.3. Advanced phase days or even several weeks to complete (Figure 1). The advanced phase is the last phase of the Maillard reaction. 2.1. Initial phase In the advanced phase, dicarbonyl compounds form isomers with the arginine and lysine residues of proteins, called AGEs. In the initial phase of the Maillard reaction, reducing sugars, They are characterized by thermal stability. The major AGEs such as glucose, fructose, or ribose, will act on the terminal are classified into 3 groups: (1) fluorescent crosslinking AGEs, amino groups of proteins, nucleic acids, or phospholipids to such as crossline and pentosidine; (2) nonfluorescent cross- form unstable Schiff bases, which will further become more linking AGEs, such as imidazolium dilysine crosslinks; and (3) stable keto-amines, also called Amadori products, after rear- nonfluorescent non-crosslinking AGEs, such as rangement. The reactions in this phase are all reversible, and N -3 carboxyethyllysine (CEL) and N -carboxymethyl-lysine3 depending on the substrate concentrations and reaction time, (CML). Except for pyrraline and pentosidine, the production of these reactions have different effects. In addition, Schiff bases AGEs is irreversible. are prone to oxidation to produce free radicals, resulting in the formation of active carbonyl intermediate products [13]. 3. Carbonyl stress mediated by MG 2.2. Propagation phase The propagation phase of the glycation process produces RCS, During the process of Amadori rearrangement, the oxidation which are considered as precursors for the formation of AGEs. function induced by the catalytic function of metal ions or MG is a highly reactive substance and is considered as one of oxygen will produce many carbonyl compounds, including the most reactive precursors of AGEs, which can be produced MG, glyoxal, and 3-deoxyglucosone. This stage is the inter- by endogenous enzymatic reactions or nonenzymatic re- mediate phase of the Maillard reaction. actions [14]. MG can produce many types of AGEs through the Please cite this article in press as: Yeh W-J, et al., Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings, Journal of Food and Drug Analysis (2016), http://dx.doi.org/10.1016/j.jfda.2016.10.017 journal of food and drug analysis xxx (2016) 1e9 3 modification of arginine or lysine residues of proteins, cerevisiae produce MG through the malolactic fermentation including Nd-(5-methyl-4-imidazolon-2-yl)-L-ornithine, 2- process [19]. Many natural plants also have high concentra- amino-5-(2-amino-5-hydro-5-methyl-4-imidazolon-1-yl) pen- tions of MG; additionally, in the presence of stress factors, tanoic acid, 2-amino-5-(2-amino-4-hydro-4-methyl-5- such as a harsh environment, the MG concentration increases imidazolon-1-yl) pentanoic acid, CEL, argpyrinidine, 4- significantly [20]. methyl-imidazolium (methylglyoxal-lysine dimer, MOLD), Once MG is produced in food, its uptake into the body may and 2-ammonio-6-({2-[4-ammonio-5-oxido-5-oxopent-ly) cause negative effects. The results of one study showed that amino]-4-methyl-4,5-dihydro-1H-imidazol-5-ylidene}amino) after the application of 50 mg MG/kg body weight/day in the hexanoate (Figure 2). The above AGEs derived from MG are all drinking water of mice for 5 months, a large amount of col- found in the bodies of organisms and are considered to be lagens accumulated in the kidney. The fluorescent staining of associated with DM and related to large and small blood vessel kidney sections showed that the accumulation of collagen in diseases as well as aging-related diseases [15]. mice fed with MG water was approximately twice the amount in healthy mice [21]. With the progressive application of 50e75 mg MG/kg body weight/day in the drinking water of rats for 7 weeks, the serum creatinine and total cholesterol con- 4.