Disease relevance of Hydroxymethylfurfural

• [reaction: see text] A practical, one-pot, two-step catalytic method is described for the synthesis of 2,5-diformylfuran (DFF) from fructose via dehydration to 5-(hydroxymethyl)furfural (HMF), followed by in situ catalytic air-oxidation [1].
• Toxicity of 5-hydroxymethylfurfural and furfural to Daphnia magna [2].
• When the three methods were compared the overlap between normals and diabetics was found to be less, using the 5-hydroxymethylfurfural HPLC method, suggesting that this procedure, although more time consuming, seems to be more useful in the management of diabetes mellitus [3].

High impact information on Hydroxymethylfurfural

• Total glycosylated haemoglobin, measured by the colorimetric thiobarbiturate method (mmol hydroxymethylfurfural/mol haemoglobin), was lower in cord than maternal blood (mean 18.7 +/- 1.7 versus 26.5 +/- 2.1, mean +/- SD, p less than 0.001) [4].
• The brown diet (BD) was rich and the white diet (WD) was poor in MRP content (hydroxymethylfurfural: 3.87 and 0.94 mg/kg; fluorescence intensity: 21.04% and 7.31%, respectively) [5].
• 5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural [6].
• After a 5-h hydrolysis at 100 degrees C, about 85% of the hexose is released, and the analytical recovery of 5-hydroxymethylfurfural is constant over a wide range of glycosylated hemoglobin concentrations [7].
• Glycosylation of hemoglobin was expressed as micromoles of hydroxymethylfurfuraldehyde per gram of globin protein (the "HMF index") [8].

Chemical compound and disease context of Hydroxymethylfurfural

• In the presence of the amorphous form of zirconium phosphate, about 80% of fructose was decomposed in sub-critical water at 240 degrees C after 120s, and the selectivity of the dehydration reaction of fructose to 5-hydroxymethylfurfural rose to 61% [9].
• The chemical formation, toxicity, and pharmacokinetics of 5-hydroxymethylfurfural (HMF) and certain other decomposition products found in parenteral solutions are reviewed [10].

Biological context of Hydroxymethylfurfural

• Erythritol also reduced the elevated serum 5-hydroxymethylfurfural level that is glycosylated with protein as an indicator of oxidative stress [11].
• Alternatively, reductive amination of 5-(hydroxymethyl)-2-furaldehyde with Raney-Ni/hydrogen and l- or d-alanine followed by mild oxidation led to (+)-(S)-1 and (-)-(R)-1, respectively [12].
• Unlike laboratory strains, gene expression response of the ethanologenic yeast to furfural and HMF was not transient, but a continued dynamic process involving multiple genes at the genome level [13].
• Enhanced biotransformation of furfural and hydroxymethylfurfural by newly developed ethanologenic yeast strains [14].
• Coniochaeta ligniaria NRRL30616, an Ascomycete that metabolizes furfural and 5-hydroxymethylfurfural, is a unique strain that may be useful for detoxifying biomass sugars [15].

Anatomical context of Hydroxymethylfurfural

• Influence of 5-hydroxymethylfurfural (5-HMF) on the overall metabolism of human blood cells [16].
• The level of nonenzymatic glycosylation, determined by hydroxymethylfurfuraldehyde (HMF) generation, in glomerular basement membrane (GMB) collagen purified from rats with streptozotocin diabetes was significantly greater than that of nondiabetic GMB [17].

Associations of Hydroxymethylfurfural with other chemical compounds

• Simultaneous determination of 5-hydroxymethylfurfural and patulin in apple juice by reversed-phase liquid chromatography [18].
• Comparison of the kinetic composition of these carrot stocks with that of model sugar solutions leads to the proposal that the changes in stock composition result from sugar diffusion, sucrose hydrolysis, and hydroxymethylfurfural (HMF) formation [19].
• The ethanologenic yeast Saccharomyces cerevisiae demonstrated a dose-dependant inhibition by the inhibitors and has the potential to transform furfural and HMF into less toxic compounds of furfuryl alcohol and 2,5-bis-hydroxymethylfuran (also termed as furan-2,5-dimethanol (FDM)), respectively [13].
• Changes in the content of low molecular weight phenolic compounds (hydroxybenzoic and hydroxycinnamic acids, aldehydes, and their esterified derivatives, tyrosol and 5-(hydroxymethyl)-2-furaldehyde) during the aging of three different classes of Sherry wine, Fino, Oloroso, and Amontillado, have been studied [20].
• Liquid chromatography was used for quantitation of sugars (glucose, fructose, sucrose, and sorbitol), nonvolatile acids (malic, quinic, citric, shikimic, and fumaric), and phenolics (chlorogenic acid and hydroxymethylfurfural [HMF]) [21].

Gene context of Hydroxymethylfurfural

• 5-(Hydroxymethyl)-2-furfural: a selective inhibitor of DNA polymerase lambda and terminal deoxynucleotidyltransferase [22].
• The AGE level was determined from the 5-hydroxymethyl-2-furaldehyde (5-HMF) content of penis samples and iNOS expression was assessed by immunohistochemistry [23].
• 5-Hydroxymethylfurfural (5-HMF) which was released from aortic elastin by acid, was assayed after STZ treatment as an index of early stage glycation [24].
• 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 [25].

Analytical, diagnostic and therapeutic context of Hydroxymethylfurfural

• HPLC analysis of the light caramel colored product showed that it contained 1% 5-hydroxymethyl-2-furaldehyde (HMF), confirmed by mass and NMR spectroscopy [26].
• A comparison of composition before and after optimal overliming revealed a substantial reduction in furfural, hydroxymethylfurfural, and three unidentified high-performance liquid chromatography (HPLC) peaks [27].
• A new, simple and selective method for the analysis of 5-hydroxymethylfurfural (HMF) in foods by gas chromatography coupled to mass spectrometry (GC-MS) is proposed [28].
• Supercritical fluid extraction of 5-hydroxymethyl-2-furaldehyde from raisins [29].
• Both the extract and 5-hydroxymethylfurfural showed significant cytotoxic activities in a brine shrimp bioassay and the LC(50) values were found to be 14.96 microg/mL and 23.71 microg/mL, respectively [30].

References