1-Amino-1-deoxy-d-fructose (“Fructosamine”) and its Derivatives

Mossine, Valeri V.; Mawhinney, Thomas P.

doi:10.1016/s0065-2318(10)64006-1

Cited by 71 publications

(56 citation statements)

References 387 publications

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“…The similar concentration at 12 days depends on the two different kinetics since in the control sample at 12 days the furosine decrease is due to its conversion into more advanced glycation end products with development of color and off-flavor. The reactivity of fructose-lysine at 37°C can promote the a-fragmentation or the b-cleavage of the sugar moiety with the consequent formation of dicarbonyls and other MRPs such as CML, CEL or the formation of cross link products such as pyrraline, pentosidine, crossline (Mossine & Mawhinney, 2010).…”

Section: Discussionmentioning

confidence: 99%

“…In milk, APs originating from the reaction of amino group with disaccharide lactose or other reducing sugars are involved in further degradation promoting the formation of cross-link products, a-dicarbonyls, hydroxycarbonyls, deoxyosones, such as 1-deoxyosone or 3-deoxyosone, 1-amino-1,4-dideoxyosones and Strecker degradation (Henle, 2005;Nursten, 2005). Also free amino acids react in milk with reducing carbonyls, contributing to formation of N-(1-deoxy-D-fructos-1-yl)-L-amino acids, or fructose-amino acids which cause an overall reduction of milk nutritive value (Mossine & Mawhinney, 2010;Pischetsrieder & Henle, 2012) and lead to the formation of volatile off-flavor and undesired molecules (van Boekel, 1998).…”

Section: Introductionmentioning

confidence: 99%

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Evolution of protein bound Maillard reaction end-products and free Amadori compounds in low lactose milk in presence of fructosamine oxidase I

et al. 2016

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Thermal treatments and storage influence milk quality, particularly in low lactose milk as the higher concentration of reducing sugars can lead to the increased formation of the Maillard reaction products (MRPs). The control of the Amadori products (APs) formation is the key step to mitigate the Maillard reaction (MR) in milk. The use of fructosamine oxidases, (Faox) provided promising results. In this paper, the effects of Faox I were evaluated by monitoring the concentration of free and bound MRPs in low lactose milk during shelf life. Results showed that the enzyme reduced the formation of protein-bound MRPs down to 79% after six days at 37°C. Faox I lowered the glycation of almost all the free amino acids resulting effective on basic and polar amino acids. Data here reported corroborate previous findings on the potentiality of Faox enzymes in controlling the early stage of the MR in foods.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evolution of protein bound Maillard reaction end-products and free Amadori compounds in low lactose milk in presence of fructosamine oxidase I

et al. 2016

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“…FruArg belongs to the class of fructosamines, which originate from a non-enzymatic reaction between glucose and arginine [9]; they modify proteins in vivo and are widely used as a diagnostic marker of long-term glucose concentration in diabetics. Fructosamine derivatives are formed in foods upon storage or dehydration and are regarded as a functional food [9].…”

Section: Introductionmentioning

confidence: 99%

“…Fructosamine derivatives are formed in foods upon storage or dehydration and are regarded as a functional food [9]. There is evidence that fructose-amino acids can act as immune-stimulants and inhibit tumorigenesis and metastasis in animal models of cancer [10]–[13].…”

Section: Introductionmentioning

confidence: 99%

Proteomic Analysis of the Effects of Aged Garlic Extract and Its FruArg Component on Lipopolysaccharide-Induced Neuroinflammatory Response in Microglial Cells

Zhou

Mossine

et al. 2014

PLoS ONE

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Aged garlic extract (AGE) is widely used as a dietary supplement, and is claimed to promote human health through anti-oxidant/anti-inflammatory activities with hypolipidemic, antiplatelet and neuroprotective effects. Prior studies of AGE have mainly focused on its organosulfur compounds, with little attention paid to its carbohydrate derivatives, such as N-α-(1-deoxy-D-fructos-1-yl)-L-arginine (FruArg). The goal of this study is to investigate actions of AGE and FruArg on antioxidative and neuroinflammatory responses in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells using a proteomic approach. Our data show that both AGE and FruArg can significantly inhibit LPS-induced nitric oxide (NO) production in BV-2 cells. Quantitative proteomic analysis by combining two dimensional differential in-gel electrophoresis (2D-DIGE) with mass spectrometry revealed that expressions of 26 proteins were significantly altered upon LPS exposure, while levels of 20 and 21 proteins exhibited significant changes in response to AGE and FruArg treatments, respectively, in LPS-stimulated BV-2 cells. Notably, approximate 78% of the proteins responding to AGE and FruArg treatments are in common, suggesting that FruArg is a major active component of AGE. MULTICOM-PDCN and Ingenuity Pathway Analyses indicate that the proteins differentially affected by treatment with AGE and FruArg are involved in inflammatory responses and the Nrf2-mediated oxidative stress response. Collectively, these results suggest that AGE and FruArg attenuate neuroinflammatory responses and promote resilience in LPS-activated BV-2 cells by suppressing NO production and by regulating expression of multiple protein targets associated with oxidative stress.

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“…Fructosamines resulting from the reaction of glucose with free amino acids or proteins is common in nature. Fructoselysine occurs in dehydrated fruits, grains, and vegetables, including raisins, prunes, dates, figs, apricots, onion, cereal, and carrots (11). Other fructosamines are found in rotting fruits and vegetables, accounting for as much as 7% of the fresh mass (12).…”

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confidence: 99%

A Mannose Family Phosphotransferase System Permease and Associated Enzymes Are Required for Utilization of Fructoselysine and Glucoselysine in Salmonella enterica Serovar Typhimurium

et al. 2015

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Salmonella enteric serovar Typhimurium, a major cause of food-borne illness, is capable of using a variety of carbon and nitrogen sources. Fructoselysine and glucoselysine are Maillard reaction products formed by the reaction of glucose or fructose, respectively, with the -amine group of lysine. We report here that S. Typhimurium utilizes fructoselysine and glucoselysine as carbon and nitrogen sources via a mannose family phosphotransferase (PTS) encoded by gfrABCD (glucoselysine/fructoselysine PTS components EIIA, EIIB, EIIC, and EIID; locus numbers STM14_5449 to STM14_5454 in S. Typhimurium 14028s). Genes coding for two predicted deglycases within the gfr operon, gfrE and gfrF, were required for growth with glucoselysine and fructoselysine, respectively. GfrF demonstrated fructoselysine-6-phosphate deglycase activity in a coupled enzyme assay. The biochemical and genetic analyses were consistent with a pathway in which fructoselysine and glucoselysine are phosphorylated at the C-6 position of the sugar by the GfrABCD PTS as they are transported across the membrane. The resulting fructoselysine-6-phosphate and glucoselysine-6-phosphate subsequently are cleaved by GfrF and GfrE to form lysine and glucose-6-phosphate or fructose-6-phosphate. Interestingly, although S. Typhimurium can use lysine derived from fructoselysine or glucoselysine as a sole nitrogen source, it cannot use exogenous lysine as a nitrogen source to support growth. Expression of gfrABCDEF was dependent on the alternative sigma factor RpoN ( 54 ) and an RpoN-dependent LevR-like activator, which we designated GfrR. IMPORTANCESalmonella physiology has been studied intensively, but there is much we do not know regarding the repertoire of nutrients these bacteria are able to use for growth. This study shows that a previously uncharacterized PTS and associated enzymes function together to transport and catabolize fructoselysine and glucoselysine. Knowledge of the range of nutrients that Salmonella utilizes is important, as it could lead to the development of new strategies for reducing the load of Salmonella in food animals, thereby mitigating its entry into the human food supply. Salmonella enterica serovar Typhimurium is one of the leading causes of food-borne illness. Salmonella causes 11% of all infections caused by bacterial food-borne pathogens in the United States and is responsible for an estimated 1 million cases of salmonellosis in the United States each year, which result in approximately 19,000 hospitalizations and 400 deaths (1). S. Typhimurium causes gastroenteritis in humans but is capable of colonizing a wide range of animals with few or no disease symptoms. S. Typhimurium utilizes a broad array of carbon and nitrogen sources (2), which may contribute to the wide host range of this bacterium. Chadhuri and coworkers found that genes encoding enzymes in a variety of catabolic processes appear to be important for S. Typhimurium colonization of the chicken, pig, and calf (3). Among those catabolic genes, some encoded phosphoenolp...

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1-Amino-1-deoxy-d-fructose (“Fructosamine”) and its Derivatives

Cited by 71 publications

References 387 publications

Evolution of protein bound Maillard reaction end-products and free Amadori compounds in low lactose milk in presence of fructosamine oxidase I

Evolution of protein bound Maillard reaction end-products and free Amadori compounds in low lactose milk in presence of fructosamine oxidase I

Proteomic Analysis of the Effects of Aged Garlic Extract and Its FruArg Component on Lipopolysaccharide-Induced Neuroinflammatory Response in Microglial Cells

A Mannose Family Phosphotransferase System Permease and Associated Enzymes Are Required for Utilization of Fructoselysine and Glucoselysine in Salmonella enterica Serovar Typhimurium

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