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Relationship between acrylamide and thermal-processing indexes in commercial breakfast cereals: a survey of Spanish breakfast cereals.

Breakfast cereals are significant contributors to the daily intake of food-derived acrylamide in Western countries. Acrylamide was determined by LC-MS in 60 commercial breakfast cereals marketed in Spain. Several SPE cartridges were evaluated for clarification of the aqueous extract. LOQ was 62 microg/kg . Acrylamide content ranged from < 62-803 microg/kg (average 292 microg/kg , and median 258 microg/kg , with an estimated acrylamide intake from breakfast cereals of 2.68 microg acrylamide/person/day. According to the German concept of minimization, a signal value 450 microg/kg was calculated. Relationships among acrylamide and some parameters of the studied samples such as type of cereal, its physical form (puffed and flaked) or certain ingredients in the formulation (proteins and dietary fibre content) were also investigated. Wheat-based cereals contained significantly higher levels of acrylamide, as did samples with higher fibre or protein content. In addition, puffed breakfast cereals also contained significantly higher levels of acrylamide. There was no significant correlation between acrylamide levels and contents of 5-hydroxymethylfurfural, furosine or cereal browning.

Acrylamide↗

In vitro anti-tyrosinase activity of 5-(hydroxymethyl)-2-furfural isolated from Dictyophora indusiata.

The inhibition of mushroom tyrosinase by methanolic extract of Dictyophora indusiata was evaluated and the bioactive component was characterized and identified as 5-(hydroxymethyl)-2-furfural (HMF) by chromatographic and spectroscopic means. Kinetic studies revealed it to be a noncompetitive inhibitor for the oxidation of L-DOPA. On the basis of these findings some related analogues were also tested for their anti-tyrosinase activity, in order to gain more insight into structure and activity relationship among these heterocyclic compounds.

Agaricales↗

A 5-hydroxymethyl furfural reducing enzyme encoded by the Saccharomyces cerevisiae ADH6 gene conveys HMF tolerance.

The fermentation of lignocellulose hydrolysates by Saccharomyces cerevisiae for fuel ethanol production is inhibited by 5-hydroxymethyl furfural (HMF), a furan derivative which is formed during the hydrolysis of lignocellulosic materials. The inhibition can be avoided if the yeast strain used in the fermentation has the ability to reduce HMF to 5-hydroxymethylfurfuryl alcohol. To enable the identification of enzyme(s) responsible for HMF conversion in S. cerevisiae, microarray analyses of two strains with different abilities to convert HMF were performed. Based on the expression data, a subset of 15 reductase genes was chosen to be further examined using an overexpression strain collection. Three candidate genes were cloned from two different strains, TMB3000 and the laboratory strain CEN.PK 113-5D, and overexpressed using a strong promoter in the strain CEN.PK 113-5D. Strains overexpressing ADH6 had increased HMF conversion activity in cell-free crude extracts with both NADPH and NADH as co-factors. In vitro activities were recorded of 8 mU/mg with NADH as co-factor and as high as 1200 mU/mg for the NADPH-coupled reduction. Yeast strains overexpressing ADH6 also had a substantially higher in vivo conversion rate of HMF in both aerobic and anaerobic cultures, showing that the overexpression indeed conveyed the desired increased reduction capacity.

Aerobiosis↗

Furfural, a precursor of the cytokinin hormone kinetin, and base propenals are formed by hydroxyl radical damage of DNA.

Recently, we have detected kinetin (N6-furfuryladenine), a well known cytokinin plant hormone, in commercially available DNA, in freshly extracted cellular DNA and in plant cell extracts. We had suggested that the furfuryl moiety of kinetin originates from furfural which is one of the primary oxidation products of deoxyribose in DNA. Here we show that the human cell extracts treated with O-(2,3,4,5,6-pentafluorobenzyl) hydroxylamine (PFBHA) give rise to oxime derivatives of various aldehydes present in the cell. Mass spectrometric analysis of silylated oximes showed several mass signals of different species, one of which was identified as furfural. Furthermore, detailed inspection of the mass spectra of DNA showed the mass signals of 165, 180, 189 and 206 m/z which correspond to cytosine-propenal, thymine-propenal, adenine-propenal and guanine-propenal, respectively. The presence of furfural, along with four base-propenals in the cell extract, as the primary oxidation products of deoxyribose, suggests that degradation of sugar residues in DNA is one of the major routes of cellular damage in addition to the modification of nucleic acid bases.

Adenine↗

Non-enzymatic glycosylation of urinary proteins in type 1 (insulin-dependent) diabetes: correlation with metabolic control and the degree of proteinuria.

In 18 control subjects and in 41 Type 1 (insulin-dependent) diabetic patients (13 with normal proteinuria, group A; 15 with microproteinuria, group B; and 13 with clinical proteinuria, group C), mean blood glucose, glycosylated haemoglobin and non-enzymatic glycosylated serum and urinary proteins, expressed as 5-hydroxymethylfurfural (5-HMF), were measured. In each group of diabetic patients, the levels of mean daily blood glucose, glycosylated haemoglobin and serum 5-HMF/mg protein were higher than in the control subjects. The urinary 5-HMF/mg proteinuria and the urinary/serum 5-HMF concentration ratio values were raised in group A and reduced in groups B and C. Moreover, they showed a negative correlation with 24-h urinary protein excretion in the control subjects and in each group of diabetic patients. The urinary 5-HMF/day in groups A, B and C was greater than in the control subjects. The urinary 5-HMF/day did not correlate with the mean daily blood glucose levels and, only in group A, did it correlate with serum 5-HMF and glycosylated haemoglobin. This suggests that, in this group, functional factors result in the increased renal elimination of 5-HMF and, therefore, of non-enzymatically glycosylated proteins. However, in the other groups of patients, this elimination depends on the degree of proteinuria.

Blood Glucose↗

[Sensory and chemical changes of dried foods under the influence of extreme storage conditions. 3. Chemical changes (authors transl)].

The content of free amino acids and free fatty acids of dried infant foods is clearly decreasing during the storage under extreme conditions, whilst the percentage composition of the fatty acids in the triglycerides remains nearly unchanged. The content of hydroxymethylfurfural is connected with the sensory changes. For the single foods as well a high increase as a strong decrease of the HMF-content can be combined with distinct sensory changes. The vitamin C-content decreases during the storage, the permeability of the packing material for oxygen and water vapor has an unfavourable effect. Furthermore the pH-value of the investigated products is lowered during the storage period.

Amino Acids↗

Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates.

Acid pretreatment of lignocellulosic biomass releases furan and phenolic compounds, which are toxic to microorganisms used for subsequent fermentation. In this study, we isolated new microorganisms for depletion of inhibitors in lignocellulosic acid hydrolysates. A sequential enrichment strategy was used to isolate microorganisms from soil. Selection was carried out in a defined mineral medium containing a mixture of ferulic acid (5 mM), 5-hydroxymethylfurfural (5-HMF, 15 mM), and furfural (20 mM) as the carbon and energy sources, followed by an additional transfer into a corn stover hydrolysate (CSH) prepared using dilute acid. Subsequently, based on stable growth on these substrates, six isolates--including five bacteria related to Methylobacterium extorquens, Pseudomonas sp, Flavobacterium indologenes, Acinetobacter sp., Arthrobacter aurescens, and one fungus, Coniochaeta ligniaria--were chosen. All six isolates depleted toxic compounds from defined medium, but only C. ligniaria C8 (NRRL 30616) was effective at eliminating furfural and 5-HMF from CSH. C. ligniaria NRRL 30616 may be useful in developing a bioprocess for inhibitor abatement in the conversion of lignocellulosic biomass to fuels and chemicals.

Acids↗

Response to different environmental stress conditions of industrial and laboratory Saccharomyces cerevisiae strains.

Two sets of Saccharomyces cerevisiae strains were compared for their physiological responses to different stress conditions. One group is composed of three strains adapted to controlled laboratory conditions (CEN.PK, LR88 and RS58), whereas the other consisted of five industrial strains (IND1101, SuperStart, LO24, LO41 and Azteca). Most industrial strains showed higher tolerance to heat shock and to an oxidative environment than laboratory strains. Excluding CEN.PK, a similar behavior was observed regarding ethanol production in high sugar concentrations (180 g/l glucose). Addition of acetate (10 g/l) or furfural (2 g/l), in concentrations similar to those found in sugar cane bagasse hydrolysates, decreased cell mass formation and growth rate in almost all strains. CEN.PK and SuperStart showed the highest sensitivity when grown in furfural-containing medium. Acetic acid treatment severely affected cell mass formation and reduced growth rate in all strains; CEN.PK and LO24 were the most resistant. The specific ethanol production rate was not affected by furfural addition. However, specific ethanol production rates decreased in response to acetic acid in four industrial strains, and increased in all laboratory strains and in LO24. No significant correlation was found between the stress tolerance of the strains tested and the transcript accumulation of genes selected by their involvement in the response to each of the stressful environments applied.

Acetic Acid↗