furaldehyde

Summary

Summary: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.

Top Publications

  1. Liu Z, Slininger P, Dien B, Berhow M, Kurtzman C, Gorsich S. Adaptive response of yeasts to furfural and 5-hydroxymethylfurfural and new chemical evidence for HMF conversion to 2,5-bis-hydroxymethylfuran. J Ind Microbiol Biotechnol. 2004;31:345-52 pubmed
    ..The ability of yeasts to adapt to and transform furfural and HMF offers the potential for in situ detoxification of these inhibitors and suggests a genetic basis for further development of highly tolerant strains for biofuel production...
  2. Keating J, Panganiban C, Mansfield S. Tolerance and adaptation of ethanologenic yeasts to lignocellulosic inhibitory compounds. Biotechnol Bioeng. 2006;93:1196-206 pubmed
    ..Though ethanologenic capacity was preserved, a net loss of performance was evident from both strains, indicating the absence of adaptation to the substrates, regardless of the sequence in which the SSL types were employed...
  3. Lin F, Tan Y, Yuan Y. Temporal quantitative proteomics of Saccharomyces cerevisiae in response to a nonlethal concentration of furfural. Proteomics. 2009;9:5471-83 pubmed publisher
    ..The expressions of 18 proteins related to stress response showed increased trends, including several highly induced heat shock proteins and proteins related to cellular signaling pathways...
  4. Liu Z, Moon J. A novel NADPH-dependent aldehyde reductase gene from Saccharomyces cerevisiae NRRL Y-12632 involved in the detoxification of aldehyde inhibitors derived from lignocellulosic biomass conversion. Gene. 2009;446:1-10 pubmed publisher
    ..YGL039W, YDR541C, and YOL151W (GRE2) appeared to be the similar type of enzymes falling into the same category of the intermediate subfamily...
  5. Koopman F, Wierckx N, de Winde J, Ruijssenaars H. Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14. Proc Natl Acad Sci U S A. 2010;107:4919-24 pubmed publisher
    ..These results pave the way for in situ detoxification of lignocellulosic hydrolysates, which is a major step toward improved efficiency of utilization of lignocellulosic feedstock...
  6. Ma M, Liu Z. Comparative transcriptome profiling analyses during the lag phase uncover YAP1, PDR1, PDR3, RPN4, and HSF1 as key regulatory genes in genomic adaptation to the lignocellulose derived inhibitor HMF for Saccharomyces cerevisiae. BMC Genomics. 2010;11:660 pubmed publisher
  7. Khalil M, Sulaiman S, Gan S. High 5-hydroxymethylfurfural concentrations are found in Malaysian honey samples stored for more than one year. Food Chem Toxicol. 2010;48:2388-92 pubmed publisher
    ..19-1131.76 mg/kg). Therefore, it is recommended that honey should generally be consumed within one year, regardless of the type...
  8. Heer D, Heine D, Sauer U. Resistance of Saccharomyces cerevisiae to high concentrations of furfural is based on NADPH-dependent reduction by at least two oxireductases. Appl Environ Microbiol. 2009;75:7631-8 pubmed publisher
    ..By overexpressing the ADH7 gene and the ORF YKL071W, we inversely engineered significantly increased furfural resistance in the parent strain, thereby demonstrating that these two enzymes are key elements of the resistance phenotype...
  9. Miller E, Jarboe L, Turner P, Pharkya P, Yomano L, York S, et al. Furfural inhibits growth by limiting sulfur assimilation in ethanologenic Escherichia coli strain LY180. Appl Environ Microbiol. 2009;75:6132-41 pubmed publisher

More Information

Publications62

  1. Ding X, Wang M, Yao Y, Li G, Cai B. Protective effect of 5-hydroxymethylfurfural derived from processed Fructus Corni on human hepatocyte LO2 injured by hydrogen peroxide and its mechanism. J Ethnopharmacol. 2010;128:373-6 pubmed publisher
  2. Wierckx N, Koopman F, Bandounas L, de Winde J, Ruijssenaars H. Isolation and characterization of Cupriavidus basilensis HMF14 for biological removal of inhibitors from lignocellulosic hydrolysate. Microb Biotechnol. 2010;3:336-43 pubmed publisher
    ..This unique substrate profile makes C. basilensis HMF14 extremely well suited for biological removal of inhibitors from lignocellulosic hydrolysates prior to their use as fermentation feedstock...
  3. Li Q, Metthew Lam L, Xun L. Biochemical characterization of ethanol-dependent reduction of furfural by alcohol dehydrogenases. Biodegradation. 2011;22:1227-37 pubmed publisher
    ..1 kJ mol(-1). The physiological benefit for ethanol-dependent reduction of furfural is likely to replace toxic and recalcitrant furfural with less toxic and more biodegradable acetaldehyde...
  4. Liu Z, Ma M, Song M. Evolutionarily engineered ethanologenic yeast detoxifies lignocellulosic biomass conversion inhibitors by reprogrammed pathways. Mol Genet Genomics. 2009;282:233-44 pubmed publisher
    ..We present significant gene interactions and regulatory networks involved in NAD(P)H regenerations and functional aldehyde reductions under the inhibitor stress...
  5. Li B, Yuan Y. Transcriptome shifts in response to furfural and acetic acid in Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2010;86:1915-24 pubmed publisher
    ..This research has provided insights into molecular response to furfural and acetic acid in S. cerevisiae, and it will be helpful to construct more resistant strains for cellulosic ethanol production...
  6. Heer D, Sauer U. Identification of furfural as a key toxin in lignocellulosic hydrolysates and evolution of a tolerant yeast strain. Microb Biotechnol. 2008;1:497-506 pubmed publisher
    ..The improved resistance of our evolved strains was based on their capacity to remain viable in a toxic environment during the prolonged, furfural induced lag phase...
  7. Miller E, Jarboe L, Yomano L, York S, Shanmugam K, Ingram L. Silencing of NADPH-dependent oxidoreductase genes (yqhD and dkgA) in furfural-resistant ethanologenic Escherichia coli. Appl Environ Microbiol. 2009;75:4315-23 pubmed publisher
    ..Together, these results suggest that the process of reducing furfural by using an enzyme with a low K(m) for NADPH rather than a direct inhibitory action is the primary cause for growth inhibition by low concentrations of furfural...
  8. Truzzi C, Annibaldi A, Illuminati S, Finale C, Rossetti M, Scarponi G. Determination of very low levels of 5-(hydroxymethyl)-2-furaldehyde (HMF) in natural honey: comparison between the HPLC technique and the spectrophotometric white method. J Food Sci. 2012;77:C784-90 pubmed publisher
  9. Binder J, Raines R. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc. 2009;131:1979-85 pubmed publisher
  10. Trifonova R, Postma J, Verstappen F, Bouwmeester H, Ketelaars J, van Elsas J. Removal of phytotoxic compounds from torrefied grass fibres by plant-beneficial microorganisms. FEMS Microbiol Ecol. 2008;66:158-66 pubmed publisher
    ..fungus depleted 2-furalaldehyde, 2-furan-carboxaldehyde-5-methyl, pyrrole-2-carboxaldehyde, 5-acetoxymethyl-2-furaldehyde and benzaldehyde-3-hydroxy-4-methoxy...
  11. Lin A, Qian K, Usami Y, Lin L, Itokawa H, Hsu C, et al. 5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix. J Nat Med. 2008;62:164-7 pubmed publisher
    ..The presence of these three compounds, particularly 3, which were not found in the unprocessed extract of Rehmanniae Radix, could substantiate the traditional medicinal use of steamed Rehmanniae Radix...
  12. Michail K, Matzi V, Maier A, Herwig R, Greilberger J, Juan H, et al. Hydroxymethylfurfural: an enemy or a friendly xenobiotic? A bioanalytical approach. Anal Bioanal Chem. 2007;387:2801-14 pubmed
    ..The mean recoveries of the assays were 79% and 89%, with acceptable accuracies and reproducibilities. Figure Schematic representation of hydroxymethylfurfural (HMF) in human plasma...
  13. Martin C, Marcet M, Almazán O, Jönsson L. Adaptation of a recombinant xylose-utilizing Saccharomyces cerevisiae strain to a sugarcane bagasse hydrolysate with high content of fermentation inhibitors. Bioresour Technol. 2007;98:1767-73 pubmed
    ..The adapted strain converted the inhibitory furaldehydes 2-furaldehyde (furfural) and 5-hydroxymethyl-2-furaldehyde (HMF) at a faster rate than the non-adapted strain...
  14. Talebnia F, Taherzadeh M. In situ detoxification and continuous cultivation of dilute-acid hydrolyzate to ethanol by encapsulated S. cerevisiae. J Biotechnol. 2006;125:377-84 pubmed
    ..0 h(-1). At this highest rate, ethanol and glycerol were also the major products with yields 0.43 and 0.076 g/g, respectively. The experiments lasted for 18-21 days, and no damage in the capsules was detected...
  15. Gorsich S, Dien B, Nichols N, Slininger P, Liu Z, Skory C. Tolerance to furfural-induced stress is associated with pentose phosphate pathway genes ZWF1, GND1, RPE1, and TKL1 in Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2006;71:339-49 pubmed
    ..These results demonstrate a strong relationship between PPP genes and furfural tolerance and provide additional putative target genes involved in furfural tolerance...
  16. Gheldof N, Wang X, Engeseth N. Identification and quantification of antioxidant components of honeys from various floral sources. J Agric Food Chem. 2002;50:5870-7 pubmed
    ..The phenolic compounds contributed significantly to the antioxidant capacity of honey but were not solely responsible for it...
  17. Nigam J. Ethanol production from wheat straw hemicellulose hydrolysate by Pichia stipitis. J Biotechnol. 2001;87:17-27 pubmed
    ..The hydrolysate used had the following composition (expressed in g x l(-1)): xylose 12.8+/-0.25; glucose 1.7+/-0.3; arabinose 2.6+/-0.21 and acetic acid 2.7+/-0.33...
  18. Palma M, Taylor L. Supercritical fluid extraction of 5-hydroxymethyl-2-furaldehyde from raisins. J Agric Food Chem. 2001;49:628-32 pubmed
    An extraction method based on supercritical CO(2) has been developed for the analysis of 5-hydroxymethyl-2-furaldehyde in raisins. To optimize extraction variables, a fractional factorial experimental design was applied...
  19. Lopez M, Nichols N, Dien B, Moreno J, Bothast R. Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates. Appl Microbiol Biotechnol. 2004;64:125-31 pubmed
    ..C. ligniaria NRRL 30616 may be useful in developing a bioprocess for inhibitor abatement in the conversion of lignocellulosic biomass to fuels and chemicals...
  20. Sárvári Horváth I, Franzén C, Taherzadeh M, Niklasson C, Liden G. Effects of furfural on the respiratory metabolism of Saccharomyces cerevisiae in glucose-limited chemostats. Appl Environ Microbiol. 2003;69:4076-86 pubmed
    ..Thus, during both aerobic growth and anaerobic growth, the ability to tolerate furfural appears to be directly coupled to the ability to convert furfural to less inhibitory compounds...
  21. Yu J, Stahl H. Microbial utilization and biopolyester synthesis of bagasse hydrolysates. Bioresour Technol. 2008;99:8042-8 pubmed publisher
    ..Poly(3-hydroxybutyrate) was the predominant biopolyester formed on the hydrolysates, but the cells could also synthesize co-polyesters that exhibit high ductility...
  22. Modig T, Liden G, Taherzadeh M. Inhibition effects of furfural on alcohol dehydrogenase, aldehyde dehydrogenase and pyruvate dehydrogenase. Biochem J. 2002;363:769-76 pubmed
  23. Liu Z, Slininger P, Gorsich S. Enhanced biotransformation of furfural and hydroxymethylfurfural by newly developed ethanologenic yeast strains. Appl Biochem Biotechnol. 2005;121-124:451-60 pubmed
    ..The development of such tolerant strains provided a basis and useful materials for further studies on the mechanisms of stress tolerance...
  24. Liu Z. Genomic adaptation of ethanologenic yeast to biomass conversion inhibitors. Appl Microbiol Biotechnol. 2006;73:27-36 pubmed
    ..The findings to date provide a strong foundation for future studies on genomic adaptation and manipulation of yeast to aid more robust strain design and development...
  25. Liu Z, Moon J, Andersh B, Slininger P, Weber S. Multiple gene-mediated NAD(P)H-dependent aldehyde reduction is a mechanism of in situ detoxification of furfural and 5-hydroxymethylfurfural by Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2008;81:743-53 pubmed publisher
    ..Conversion pathways of furfural and HMF relevant to glycolysis and ethanol production were refined based on our findings in this study...
  26. Almeida J, Bertilsson M, Gorwa Grauslund M, Gorsich S, Liden G. Metabolic effects of furaldehydes and impacts on biotechnological processes. Appl Microbiol Biotechnol. 2009;82:625-38 pubmed publisher
    ..One group of compounds in this category is the furaldehydes. 2-Furaldehyde (furfural) and substituted 2-furaldehydes--most importantly 5-hydroxymethyl-2-furaldehyde--are the dominant ..
  27. Cerecetto H, Di Maio R, Gonzalez M, Risso M, Sagrera G, Seoane G, et al. Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. structure-activity relationships. Eur J Med Chem. 2000;35:343-50 pubmed
    Several novel semicarbazone derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde and semicarbazides bearing a spermidine-mimetic moiety...
  28. Huber G, Chheda J, Barrett C, Dumesic J. Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science. 2005;308:1446-50 pubmed
    ..These liquid alkanes are of the appropriate molecular weight to be used as transportation fuel components, and they contain 90% of the energy of the carbohydrate and H2 feeds...
  29. Gutierrez T, Ingram L, Preston J. Purification and characterization of a furfural reductase (FFR) from Escherichia coli strain LYO1--an enzyme important in the detoxification of furfural during ethanol production. J Biotechnol. 2006;121:154-64 pubmed
    ..The conversion of relatively toxic furfural to less toxic furfuryl alcohol suggests a beneficial role for this enzyme in mitigating furfural toxicity encountered during ethanol production from lignocellulosic biomass...
  30. Talebnia F, Niklasson C, Taherzadeh M. Ethanol production from glucose and dilute-acid hydrolyzates by encapsulated S. cerevisiae. Biotechnol Bioeng. 2005;90:345-53 pubmed
    ..However, since the hydrolyzates were too toxic, the encapsulated cells lost their activity gradually in sequential batches...
  31. Brustugun J, Tønnesen H, Edge R, Navaratnam S. Formation and reactivity of free radicals in 5-hydroxymethyl-2-furaldehyde--the effect on isoprenaline photostability. J Photochem Photobiol B. 2005;79:109-19 pubmed
    ..When sterilized by heat small amounts of the substance 5-hydroxymethyl-2-furaldehyde (5-HMF) is produced from glucose...
  32. Petersson A, Almeida J, Modig T, Karhumaa K, Hahn Hägerdal B, Gorwa Grauslund M, et al. A 5-hydroxymethyl furfural reducing enzyme encoded by the Saccharomyces cerevisiae ADH6 gene conveys HMF tolerance. Yeast. 2006;23:455-64 pubmed
    ..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...
  33. Almeida J, Roder A, Modig T, Laadan B, Liden G, Gorwa Grauslund M. NADH- vs NADPH-coupled reduction of 5-hydroxymethyl furfural (HMF) and its implications on product distribution in Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2008;78:939-45 pubmed publisher
  34. Nichols N, Mertens J. Identification and transcriptional profiling of Pseudomonas putida genes involved in furoic acid metabolism. FEMS Microbiol Lett. 2008;284:52-7 pubmed publisher
    ..The LysR-family gene appears to act positively, and the GcvR-family gene negatively, in regulating expression of neighboring genes in response to FA...
  35. Lin F, Qiao B, Yuan Y. Comparative proteomic analysis of tolerance and adaptation of ethanologenic Saccharomyces cerevisiae to furfural, a lignocellulosic inhibitory compound. Appl Environ Microbiol. 2009;75:3765-76 pubmed publisher
    ..These insights into the response of yeast to the presence of furfural will benefit the design and development of inhibitor-tolerant ethanologenic yeast by metabolic engineering or synthetic biology...
  36. Moon J, Shibamoto T. Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans. J Agric Food Chem. 2009;57:5823-31 pubmed
    ..The results of the present study suggest that controlling the roasting conditions according to the formation of particular chemicals can prepare a roasted coffee with preferable flavor...
  37. Cheng H, Liu X, Chen K. [Chemical constituents of ethyl acetate extract from Polygonum perfoliatum]. Zhong Yao Cai. 2012;35:1088-90 pubmed
    ..To study the chemical constituents of Polygonum perfoliatum...
  38. He Y, Jiang C, Jiang J, Di J, Liu F, Ding Y, et al. One-pot chemo-enzymatic synthesis of furfuralcohol from xylose. Bioresour Technol. 2017;238:698-705 pubmed publisher
    ..Finally, the yield of FOL from 200mM furfural was achieved to 100% by Escherichia coli CCZU-K14 whole cells after 24h. In conclusion, this strategy show high potential application for the effective synthesis of FOL. ..
  39. Tai C, Li S, Xu Q, Ying H, Huang H, Ouyang P. Chitosan production from hemicellulose hydrolysate of corn straw: impact of degradation products on Rhizopus oryzae growth and chitosan fermentation. Lett Appl Microbiol. 2010;51:278-84 pubmed publisher
    ..To examine the potential use of hemicellulose hydrolysate (HH) for the production of chitosan by Rhizopus oryzae and investigate the influence of contents in HH on mycelia growth and chitosan synthesis...
  40. Franden M, Pienkos P, Zhang M. Development of a high-throughput method to evaluate the impact of inhibitory compounds from lignocellulosic hydrolysates on the growth of Zymomonas mobilis. J Biotechnol. 2009;144:259-67 pubmed publisher
  41. Monavari S, Galbe M, Zacchi G. Impact of impregnation time and chip size on sugar yield in pretreatment of softwood for ethanol production. Bioresour Technol. 2009;100:6312-6 pubmed publisher
  42. Zeng J, Guo Z, Xiao Y, Wang C, Zhang X, Liang X. Purification of polar compounds from Radix isatidis using conventional C18 column coupled with polar-copolymerized C18 column. J Sep Sci. 2010;33:3341-6 pubmed publisher
    ..purified and three of them were identified as 3-methyl-5-vinyloxazolidin-2-one (compound A), 5-hydroxymethyl-2-furaldehyde (compound B) and 3-methylfuran-2-carboxylic acid (compound G) based on the MS, IR and extensive NMR data, ..
  43. Goncalves L, Magalhães P, Valente I, Pacheco J, Dostalek P, Sykora D, et al. Analysis of aldehydes in beer by gas-diffusion microextraction: characterization by high-performance liquid chromatography-diode-array detection-atmospheric pressure chemical ionization-mass spectrometry. J Chromatogr A. 2010;1217:3717-22 pubmed publisher
    ..5%) and linearity as well as good limits of detection (AA-12.3, FA-1.5 and MA 5.4microgL(-1)) and quantification (AA-41, FA-4.9 and MA 18microgL(-1)); it also appears to be competitive in terms of speed and cost of analysis...
  44. Jordan D, Braker J, Bowman M, Vermillion K, Moon J, Liu Z. Kinetic mechanism of an aldehyde reductase of Saccharomyces cerevisiae that relieves toxicity of furfural and 5-hydroxymethylfurfural. Biochim Biophys Acta. 2011;1814:1686-94 pubmed publisher
    ..221, 0.00158, 140) and HMFOH (0.0105, 0.000104, 101)...
  45. Akıllıoglu H, Mogol B, Gökmen V. Degradation of 5-hydroxymethylfurfural during yeast fermentation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011;28:1629-35 pubmed publisher
    ..05). The conversion of HMF into hydroxymethyl furfuryl alcohol seems to be a primary activity of yeast cells, and presence of sugars in the fermentation medium increases this activity...
  46. Hansen T, Woodley J, Riisager A. Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose. Carbohydr Res. 2009;344:2568-72 pubmed publisher
    ..Decreasing the fructose concentration significantly improved the HMF selectivity, but possibly made the production route less attractive from an industrial point of view due to the resultant low throughput...
  47. Price C, Razskazovskiy Y, Bernhard W. Factors affecting the yields of C1' and C5' oxidation products in radiation-damaged DNA: the indirect effect. Radiat Res. 2010;174:645-9 pubmed publisher
    ..In contrast, the existence of an oxygen-independent pathway of 2-dL formation suggests that C1' sugar radicals can also be oxidized by radiation-produced oxidizing intermediates such as electron-loss centers on guanines...
  48. Amiri H, Karimi K, Roodpeyma S. Production of furans from rice straw by single-phase and biphasic systems. Carbohydr Res. 2010;345:2133-8 pubmed publisher
    ..Using THF as an extracting solvent, a relatively high furfural yield, 118.2 g/kg straw, was obtained, and 96% of furfural produced in this system was extracted into THF during the process...
  49. Ricci A, Piccolella S, Pepi F, Patsilinakos A, Ragno R, Garzoli S, et al. Gas-phase basicity of 2-furaldehyde. J Mass Spectrom. 2012;47:1488-94 pubmed publisher
    2-Furaldehyde (2-FA), also known as furfural or 2-furancarboxaldehyde, is an heterocyclic aldehyde that can be obtained from the thermal dehydration of pentose monosaccharides...
  50. Kimura H, Nakahara M, Matubayasi N. Solvent effect on pathways and mechanisms for D-fructose conversion to 5-hydroxymethyl-2-furaldehyde: in situ 13C NMR study. J Phys Chem A. 2013;117:2102-13 pubmed publisher
    ..having one double bond through dehydration, and finally into 5-hydroxymethyl-2-furaldehyde (5-HMF) having two double bonds...
  51. Ra C, Jeong G, Shin M, Kim S. Biotransformation of 5-hydroxymethylfurfural (HMF) by Scheffersomyces stipitis during ethanol fermentation of hydrolysate of the seaweed Gelidium amansii. Bioresour Technol. 2013;140:421-5 pubmed publisher
    ..Biotransformation of HMF to less inhibitory compounds by S. stipitis KCTC 7228 could enhance overall fermentation yields of seaweed hydrolysates to ethanol...
  52. Seo C, Kim J, Shin H. Simultaneous determination of seven constituents in herbal prescription jaeumganghwa-tang using HPLC-PDA. Afr J Tradit Complement Altern Med. 2012;10:113-23 pubmed
    ..of seven components of the traditional herbal prescription Jaeumganghwa-tang (JGT), including 5-hydroxymethyl-2-furaldehyde, albiflorin, paeoniflorin, liquiritin, ferulic acid, nodakenin, and glycyrrhizin...
  53. Kadri S, Zaluski R, Pereira Lima G, Mazzafera P, De Oliveira Orsi R. Characterization of Coffea arabica monofloral honey from Espírito Santo, Brazil. Food Chem. 2016;203:252-257 pubmed publisher
    ..59 ± 154.3 and 343.75 ± 25.56 mg kg(-1), respectively). The caffeine content in coffee nectar (1.64 mg kg(-1)) was approximately 8-fold lower than that in honey (12.02 ± 0.81 mg kg(-1)). ..