HMF can form in sugar-containing food, particularly as a result of heating or cooking. Subsequently, HMF can penetrate the erythrocytes and form stable a Schiff-base adduct with the N terminal V11 nitrogen of HbS in a symmetrical fashion. Hydroxymethyl Furfural Content of Concentrated Food Products Reactivities Involved in the Seliwanoff Reaction - ResearchGate 5:219233, Spano N et al (2006) An RP-HPLC determination of 5-hydroxymethylfurfural in honey: the case of strawberry tree honey. CyTA J Food 11:713, Monien BH, Engst W, Barknowitz G, Seidel A, Glatt H (2012) Mutagenicity of 5-hydroxymethylfurfural in V79 cells expressing human SULT1A1: identification and mass spectrometric quantification of DNA adducts formed. Factors affecting the rate of HMF formation include temperature, pH [62], type of sugar [93], concentration of divalent cations [64] and water activity [63, 90] in the medium. HMF is barely detectable in freshly centrifuged honey, but increases at 2-3 . Many studies have revealed that different cells respond to 5-HM-induced cytotoxicity differently. Hypoxia may be induced by many factors, including altitude and self-related conditions such as ischemia, atherosclerosis and cancer [126]. Makowska et al. Reflectoquant Hydroxymethylfurfural (HMF) Test, MilliporeSigma - VWR Introduction Hydroxymethylfurfural (5-hydroxymethyl-2-furaldehyde, HMF), a by-product of non-enzymatic browning reaction between an amino acid and reducing sugar, is a well-known intermediate compound of the Maillard reaction ( Ariffin, Ghazali, & Kavousi, 2014). 117952. Anticancer Res 29:19211926, Terrab A, Gonzlez AG, Dez MJ, Heredia FJ (2003) Characterisation of moroccan unifloral honeys using multivariate analysis. [125] indicated that orally administered HMF is converted to reactive SMF after being absorbed through the gastrointestinal tract. The freshness of honey is determined by measuring its hydroxymethylfurfural (HMF) content. [27] This is a problem for American beekeepers because they use HFCS as a source of sugar when there are not enough nectar sources to feed honeybees, and HMF is toxic to them. J Agric Food Chem 61:1020910214, Anese M, Suman M, Nicoli MC (2010) Acrylamide removal from heated foods. Procedure of Anthrone Test. The ring of the structure is centered on furan moieties, whereas the two functional groups, i.e., formyl and hydroxy-methyl groups, are linked at the second and fifth positions, respectively (Fig. HMF also reduces the levels of caspases 3 and 9 (executioner of apoptosis) in these cells [178]. Its formation has been the topic of significant study as HMF was regarded as being potentially carcinogenic to humans. The mitochondrial membrane potential is also reduced and negatively affects hypoxic cells [75]. Therefore, HMF may be a potent anti-allergic compound [7]. The test solutions were observed to be stable within 9 days of preparation while the stock solution could last up to 23 days (Figure 4). These events lead to Ca2+ influx and the release of mediators by degranulation, MAPK phosphorylation, upregulation of cytokine gene expression and increased ROS generation [23, 83, 84, 154]. Food Chem Toxicol 48:644649, Ayansola AA, Banjo AD (2011) Physico-chemical Evaluation of the Authenticity of Honey Marketed in Southwestern Nigeria. Eur Food Res Technol 228:311319, Chefrour C, Draiaia R, Tahar A, Kaki YA, Bennadja S, Battesti M (2009) Physicochemical characteristics and pollen spectrum of some north-east algerian honeys. In his newer spectrophotometric method, White utilized a clarified honey sample containing 0.1% sodium bisulfate as a reference and as honey solution without sodium bisulfate as a sample [180]. Therefore, bee keepers must use alternative sources to replenish the carbohydrate demand of bees, such as sucrose, high fructose corn syrup (HFCS), various fruit sugars and invert sugars [117]. Elsevier, Amsterdam, pp 7481, Gomes S, Dias LG, Moreira LL, Rodrigues P, Estevinho L (2010) Physicochemical, microbiological and antimicrobial properties of commercial honeys from Portugal. Provided by the Springer Nature SharedIt content-sharing initiative. A quick and simple paper-based method for detection of furfural and 5 Seliwanoff's Test uses 6M HCl as dehydrating agent and resoncinol as condensation reagent. Test-kits for rapid analyses are also available (e.g. In fact, the authors also reported that Tg sickle mice pre-treated with HMF survived longer under hypoxic conditions than did untreated mice, indicating the potential of HMF as an anti-sickling agent. All references to Merck refer to Merck KGaA, Darmstadt, Germany. 5-Hydroxymethylfurfural | C6H6O3 | CID 237332 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Eur Food Res Technol 225:815820, Goldberg MA, Brugnara C, Dover GJ, Schapira L, Lacroix L, Bunn HF (1992) Hydroxyurea and erythropoietin therapy in sickle cell anemia. Merck KGaA, Darmstadt, Germany, 2014. 1. [108] reported the mean HMF concentration in Malaysian honeys stored for 2months at 45C to be 35.98mg/kg. Toxicology 15:219232, Friedberg EC, Feaver WJ, Gerlach VL (2000) The many faces of DNA polymerases: strategies for mutagenesis and for mutational avoidance. Mutat Res Genet Toxicol Environ Mutagen 580:4152, Glatt H, Schneider H, Murkovic M, Monien BH, Meinl W (2011) Hydroxymethyl-substituted furans: mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases. Basophils and mast cells participate in the pathogenesis and manifestations of allergic reactions such as asthma, atopic dermatitis and allergic rhinitis. Food Chem 58:129133, Singh N, Singh S, Bawa A, Sekhon K (1988) Honeyits food uses. HMF is a cyclic aldehyde produced by sugar degradation through the Maillard reaction (a non-enzymatic browning reaction) during food processing or long storage of honey [102]. A new class of spectrophotometers for water analysis. In another study conducted on four honey samples (eucalyptus, sulla orange and chestnut), Fellico et al. Proc Natl Acad Sci 97:56815683, Fromowitz M et al (2012) Bone marrow genotoxicity of 2, 5-dimethylfuran, a green biofuel candidate. HMF is easily absorbed from food through the gastrointestinal tract and, upon being metabolized into different derivatives, is excreted via urine. In the related Bial's test for pentoses, the hydroxymethylfurfural from hexoses may give a muddy-brown or gray solution, but this is easily distinguishable from the green color of pentoses. Seminars in oncology. J Apic Res 24:120124, Xiao PG, Xing ST, Wang LW (1993) Immunological aspects of Chinese medicinal plants as antiageing drugs. Anal Bioanal Chem 405:47374745, Ramadan K, Maga G, Shevelev IV, Villani G, Blanco L, Hbscher U (2003) Human DNA polymerase possesses terminal deoxyribonucleotidyl transferase activity and can elongate RNA primers: implications for novel functions. BMC Complement Altern Med 13:43, Morales FJ (2008) Hydroxymethylfurfural (HMF) and related compounds process-induced food toxicants: occurrence, formation, mitigation, and health risks. Nutr Metabol 1:10, Hie AH, Svendsen C, Brunborg G, Glatt H, Alexander J, Meinl W, Husy T (2015) Genotoxicity of three food processing contaminants in transgenic mice expressing human sulfotransferases 1A1 and 1A2 as assessed by the in vivo alkaline single cell gel electrophoresis assay. Enolization is believed to be the rate-determining step of HMF production. Accurate quantitative analysis of HMF is of great importance because HMF is a marker of quality deterioration, thermal processing and other adulteration practices. J Argent Chem Soc 96:3341, Capuano E, Ferrigno A, Acampa I, Ait-Ameur L, Fogliano V (2008) Characterization of the Maillard reaction in bread crisps. In their study on Malaysian honey samples [81], showed that honey samples stored for 36months had HMF values below the International Honey Commission (IHC) limit for tropical honey (<80g/kg); however, samples stored for 1224months had HMF concentrations above the recommended level. Second, fructose forms an equilibrium mixture of difructoses and dianhydrides and thus internally blocks most reactive groups, leading to the formation of certain by-products. Honey is considered both nutritional and medicinal, although the presence of certain constituents, for example, heavy metals (even in trace amounts), some alkaloids, and HMF and its derivatives may contribute to honeys toxicity [77, 152]. [190] established the TDI for HMF as 132mg/day using a 40-fold safety margin. Many agents also exhibit reduced bioavailability in minimal doses and react to non-target proteins. Res Rural Dev 23:190, Kitts DD, Chen X-M, Jing H (2012) Demonstration of antioxidant and anti-inflammatory bioactivities from sugaramino acid Maillard reaction products. 215:173, Escriche I, Visquert M, Carot JM, Domenech E, Fito P (2008) Effect of honey thermal conditions on hydroxymethylfurfural content prior to pasteurization. J Agric Res 70:640645, Alvarez-Suarez JM et al (2010) Antioxidant and antimicrobial capacity of several monofloral Cuban honeys and their correlation with color, polyphenol content and other chemical compounds. Preliminary in vivo studies using transgenic sickle mice showed that orally administered 5HMF inhibits the formation of sickled cells in the blood. There is no particular strategy for mitigating the formation of HMF in honey due to the numerous precursors of HMF and the types of reaction orders involved [35]. [8][9] It is also produced industrially on a modest scale[10] as a carbon-neutral feedstock for the production of fuels[11] and other chemicals.[12]. Krainer et al. The human genome encodes 16 DNA-dependent DNA polymerases. It is concluded that there are no heat-processed food products that are free of HMF. Chem Rev 106:40444098, Hunter JS (1959) Determination of optimum operating conditions by experimental methods. Hydroxymethylfurfural (HMF) Test | 117952 - Merck Solayman&Md. Molecules 17:1119911215, Kim K, Kim Y, Kim HY, Ro JY, Jeoung D (2008) Inhibitory mechanism of anti-allergic peptides in RBL2H3 cells. J Mol Biol 339:395404, Ramirez-Jimenez A, Guerra-Hernndez E, Garca-Villanova B (2000) Browning indicators in bread. Acta Vet Brno 74:147152, Mehryar L, Esmaiili M, Hassanzadeh A (2013) Evaluation of some physicochemical and rheological properties of iranian honeys and the effect of temperature on its viscosity. BMC Complement Altern Med 12:177, Islam M, Khalil M, Gan SH (2014) Toxic compounds in honey. Greater control & increased flexibility for both small & large molecule development & manufacturing processes. Deletion of pgi gene in E. coli increases tolerance to furfural and 5 Pioneering excellence with Steritest Symbio Pumps. The mice had a mutant copy of the tumor suppressor gene adenomatous polyposis coli (APC). In addition, because water molecules are the main target of this mechanism, heat is generated in the portion of food containing water [195]. Therefore, food processors must know the effects of different factors so that necessary precautions can be adopted previously to limit and/or optimize the synthesis of HMF in food. Replaces. . 5-Hydroxymethylfurfural. Similar chemistry is seen with 5-carbon sugars (pentoses), which react with aqueous acid to form furfural. [38], which is based on the operating principle of the Winkler method and provides a detection range of 540ppm. Method 5-(Hydroxymethyl)furfural (5-hydroxymethyl- 2-furan-carbaldehyde, HMF) reacts with a barbi-turic acid derivative and an aminophenazone derivative to form a red-violet compound that is determined reflectometrically. Arch Toxicol 86:701711, Beaven MA, Metzger H (1993) Signal transduction by Fc receptors: the Fc&RI case. Biochem Biophys Res Commun 251:137141, Olga E, Mara F-G, Carmen SM (2012) Differentiation of blossom honey and honeydew honey from Northwest Spain. Hydroxymethylfurfural (HMF) Test reflectometric, 1.0-60.0 mg/L J Agric Food Chem 18:295297, Florian S, Bauer-Marinovic M, Taugner F, Dobbernack G, Monien BH, Meinl W, Glatt H (2012) Study of 5-hydroxymethylfurfural and its metabolite 5-sulfooxymethylfurfural on induction of colonic aberrant crypt foci in wild-type mice and transgenic mice expressing human sulfotransferases 1A1 and 1A2. Springer Nature. Nishi et al. Wilderness Environ Med 16:172175, Paulsen JE, Lberg EM, lstrn HB, Knutsen H, Steffensen I-L, Alexander J (2005) Flat dysplastic aberrant crypt foci are related to tumorigenesis in the colon of azoxymethane-treated rat. Hydroxymethylfurfural (HMF) . Uric acid is the end product of purine catabolism. Reflectoquant HMF, Merck KGaA).[36][37]. In these foods it is also slowly generated during storage. Previous studies have reported that honey stored at low temperatures and/or under fresh conditions has low or minimal HMF concentrations, while aged and/or honey stored at comparatively higher or medium temperature has high HMF concentrations. volume12, Articlenumber:35 (2018) To evaluate the contribution of a food to HMF intake, its consumption-pattern has to be considered. HFCS is produced commercially from corn starch by using enzymes such as alpha amylase, amylo-glucosidase and invertase [26, 29], whereas sucrose is produced by acid hydrolysis alone [18]. A unique and efficient rapid screening technique is direct analysis in real time (DART) coupled with time-of-flight mass spectrometry (TOF-MS), which has been reported to yield a chromatogram with high resolution [134]. The obtained results ranged from .02mg/kg (honey Acacia) to 27.40mg/kg (medow). HMF also induces skin papilloma. Starch Strke 42:314321, Lee HS, Nagy S (1990) Relative reactivities of sugars in the formation of 5-hydroxymethylfurfural in sugar-catalyst model systems1. Following the formation of such an adduct, HMF allosterically shifts the oxygen equilibrium curve to the left and prevents the sickling of erythrocytes. Indian Food Packer 42:1525, Sodr GdS, Marchini LC, Moreti ACdCC, Otsuk IP, Carvalho CALd (2011) Physicochemical characteristics of honey produced by Apis mellifera in the Picos region, state of Piau. Unlike for honey, in the processing of other foodstuffs, comparatively higher temperatures (during baking, roasting), longer duration times, and different additives are required, which profoundly affect the HMF content in the foods. Environ Mol Mutagen 56:709714, Hossain SA, Pal PK, Sarkar PK, Patil GR (1999) Sensory characteristics of dudh churpi in relation to its chemical composition. The extent of HMF formation in cereal products is heavily dependent on many factors, including temperature, dough fermentation process, water activity and the presence of fruits, grains and other flavorings or additives (such as cocoa, malt, sucrose, glucose, salt, and honey). Hydroxymethylfurfural (HMF), is also known as furfural 5-hydroxymethyl, formed by the degradation of polysaccharide sugar in an organic compound. Forschung 192:1923, Kroh LW (1994) Caramelisation in food and beverages. Codex Stan 12:1982, Alizadeh M, Khodaei H, Mesgari Abbasi M, Saleh-Ghadimi S (2017) Assessing the effect of 5-hydroxymethylfurfural on selected components of immune responses in mice immunised with ovalbumin. Beschreibung quantitative Qualittsniveau 100 specific analyte (s) hydroxymethylfurfural (Hmf) reaction suitability reaction type: enzymatic reaction measuring range 1.0-60.0 mg/L (hydroxymethylfurfural (HMF)) Kompatibilitt RQflex 10 Plus RQflex 10 RQflex 20 for use with REFLECTOQUANT detection method HMF is an organic compound that arises from the dehydration of fructose, e.g. HMF is an organic compound that arises from the dehydration of fructose, e.g. Cite this article. Biochem Pharmacol 78:414419, Ball DW (2007) The chemical composition of honey. 1.17952.0007. In addition to being directly produced when heating sugar from the degradation of hexoses under acidic conditions at high temperatures and/or during the Maillard reaction [15], HMF is produced from the oligo- and polysaccharides that can yield hexoses upon hydrolysis. Nature 239:217219, Makowska D, Majak I, Bartos A, Sowianek M, cka A, Leszczyska J (2017) 5-hydroxymethylfurfural content in selected gluten-and gluten-free cereal food products, Markowicz DB, Monaro E, Siguemoto E, Sfora M, Valdez B (2012) Maillard reaction products in processed foods: pros and cons. Moniruzzaman et al. The productivity of apiculture is highly dependent on the health, survival and quality of honey bees. ROS are produced as toxic by-products of the bodys aerobic metabolism. Reagents required in the tests and assay for U.S. Pharmacopeia and National Formulary articles and those required only in determining the quality of other reagents are listed in this section, with specifications appropriate to their intended uses. J Food Process Eng 23:2555. HMF is an organic compound that arises from the dehydration of fructose, e.g. Zaitzev et al. In this method, a single and sharp reduction signal was created at 1100mV versus argentum or argentum chloride, while borate was used as a supporting electrolyte. accomplished a satisfactory result of the proficiency test. 1.17952.0007. Take a tube labeled as one as blank containing 1ml of just distilled water and the rest of the tubes labeled 2 . The classical approach tends to suffer from poor yields as HMF continues to react in aqueous acid, forming levulinic acid. Solved 1. The color reactions used in these experiments - Chegg Another study using human embryonic kidney cells (HEK293) that constitutively express OAT1 and OAT2 transporters supports this mechanism [19]. Ibrahim Khalil, Department of Biochemistry, Primeasia University, Banani, 1213, Bangladesh, School of Medical Sciences, Universiti Sains Malaysia, 16150, Kubang Kerian, Kelantan, Malaysia, School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor, Malaysia, You can also search for this author in Moreover, it was shown that heating honey samples collected from Anatolia in Turkey at 135C for 100s produced similar amounts of HMF as that yielded by heating samples to 150C for 40s. According to [150], there is a logarithmic relationship between the storage time and HMF levels in honey. HMF concentrations were highest in dates (1000mg/kg) and plums (11002200mg/kg). Hydroxymethylfurfural (HMF) Test | 117952 - Merck Mol Immunol. In this technology, depending on the physical and chemical properties of the compounds to be removed, the temperature, pressure and time can be adjusted. 1). Replaces. The reagent used in Seliwanoff's test consists of resorcinol and concentrated hydrochloric acid . In: Valdez B (ed) Food industrial processes-methods and equipment, 1st edn. Our portfolio of innovative products, services and solutions. Your privacy choices/Manage cookies we use in the preference centre. It is almost ubiquitous in everyday food products such as cereals, bread, dairy products, honey, juices, and liqueurs in varying concentrations. To our knowledge, this is the first study to extensively report on HMF in honey from all over the world and to provide a general overview to explore its effects on both bee and human health. Ordez-Santos et al. Food and Chemical Toxicology, 46 (2008), pp. Hydroxymethylfurfural (HMF) Test | 117952 - Merck Food Chem Toxicol 48:24902499, Ameur LA, Mathieu O, Lalanne V, Trystram G, Birlouez-Aragon I (2007) Comparison of the effects of sucrose and hexose on furfural formation and browning in cookies baked at different temperatures. Schoental et al. Albal-Hurtado et al. Hydroxymethylfurfural (HMF) Test reflectometric, 1.0-60.0 mg/L (hydroxymethylfurfural (HMF)), for use with REFLECTOQUANT; Synonyms: Hydroxymethylfurfural (HMF) chemical test strips,Hydroxymethylfurfural (HMF) test strip for instrument reader; find Supelco-117952 MSDS, related peer-reviewed papers, technical documents, similar products & more . Fresh cookies baked at 300C and with saccharose added during processing have been reported to contain as much as 1100mg/kg HMF. Adv Protein Chem 69:137165, Belay A, Solomon W, Bultossa G, Adgaba N, Melaku S (2013) Physicochemical properties of the Harenna forest honey, Bale, Ethiopia. Green Chem 13:754793, Roychoudhury R, Jay E, Wu R (1976) Terminal labeling and addition of homopolymer tracts to duplex DNA fragments by terminal deoxynudeotidyl transferase.
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