Table of Contents Author Guidelines Submit a Manuscript
The Scientific World Journal
Volume 2014, Article ID 215783, 11 pages
http://dx.doi.org/10.1155/2014/215783
Research Article

2-Pentanone Production from Hexanoic Acid by Penicillium roqueforti from Blue Cheese: Is This the Pathway Used in Humans?

1Department of Clinical Biochemistry, Southampton General Hospital, C level, MP 6, South Block, Tremona Road, Southampton SO16 6YD, UK
2School of Pharmacy and Biomedical Sciences, University of Portsmouth, St Michael’s Building, White Swan Road, Portsmouth PO1 2DT, UK

Received 14 November 2013; Accepted 6 February 2014; Published 27 March 2014

Academic Editors: M. Makishima and H. Yamaza

Copyright © 2014 Valerie Walker and Graham A. Mills. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Walker, J. P. Begley, and E. M. Stansbridge, “2-Pentanone: an indicator of peroxisomal acyl-CoA thioesterase activity?” Journal of Inherited Metabolic Disease, vol. 31, supplement 1, p. 67, 2008. View at Google Scholar
  2. A. Zlatkis, R. S. Brazell, and C. F. Poole, “The role of organic volatile profiles in clinical diagnosis,” Clinical Chemistry, vol. 27, no. 6, pp. 789–797, 1981. View at Google Scholar · View at Scopus
  3. T. Niwa, “Metabolic profiling with gas chromatography-mass spectrometry and its application to clinical medicine,” Journal of Chromatography—Biomedical Applications, vol. 379, pp. 313–345, 1986. View at Google Scholar · View at Scopus
  4. M. Statheropoulos, A. Agapiou, and A. Georgiadou, “Analysis of expired air of fasting male monks at Mount Athos,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 832, no. 2, pp. 274–279, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Yancey, M. L. Holland, R. Stuart, D. Wiesler, and M. Novotny, “Urinary profiles of organic acids and volatile metabolites during the starvation process in rats,” Journal of Chromatography B: Biomedical Sciences and Applications, vol. 382, pp. 3–18, 1986. View at Google Scholar · View at Scopus
  6. G. Rhodes, M. L. Holland, and D. Wiesler, “Excretion of urinary volatile metabolites in response to alloxan induced diabetes of short duration in rats,” Journal of Chromatography, vol. 228, pp. 33–42, 1982. View at Google Scholar · View at Scopus
  7. H. L. Lewis and D. W. Darnall, “Fatty acid toxicity and methyl ketone production in Aspergillus niger,” Journal of Bacteriology, vol. 101, no. 1, pp. 65–71, 1970. View at Google Scholar · View at Scopus
  8. J. E. Kinsella and D. H. Hwang, “Enzymes of Penicillium roqueforti involved in the biosynthesis of cheese flavor,” CRC Critical Reviews of Food Science & Nutrition, vol. 8, no. 2, pp. 191–228, 1976. View at Google Scholar · View at Scopus
  9. L. K. Pannell and N. F. Olson, “Methyl ketone production in milk-fat-coated microcapsules. 2-Methyl ketones from controlled concentrations of free fatty acids,” Journal of Dairy Science, vol. 74, no. 7, pp. 2054–2059, 1991. View at Google Scholar
  10. E. J. Vandamme, “Bioflavours and fragrances via fungi and their enzymes,” Fungal Diversity, vol. 13, pp. 153–166, 2003. View at Google Scholar · View at Scopus
  11. M. F. Baltazar, F. M. Dickinson, and C. Ratledge, “Oxidation of medium-chain acyl-CoA esters by extracts of Aspergillus niger: emzymology and characterization of intermediates by HPLC,” Microbiology, vol. 145, no. 1, pp. 271–278, 1999. View at Google Scholar · View at Scopus
  12. S. Fadda, A. Lebert, S. Leroy-Sétrin, and R. Talon, “Decarboxylase activity involved in methyl ketone production by Staphylococcus carnosus 833, a strain used in sausage fermentation,” FEMS Microbiology Letters, vol. 210, no. 2, pp. 209–214, 2002. View at Publisher · View at Google Scholar · View at Scopus
  13. S. Valenciano, J. R. De Lucas, A. Pedregosa, I. F. Monistrol, and F. Laborda, “Induction of β-oxidation enzymes and microbody proliferation in Aspergillus nidulans,” Archives of Microbiology, vol. 166, no. 5, pp. 336–341, 1996. View at Publisher · View at Google Scholar · View at Scopus
  14. J. Pawlak, B. J. Bahnson, and V. E. Anderson, “DFT/PM3 study of the enoyl-CoA hydratase catalyzed reaction,” Nukleonika, vol. 47, supplement 1, pp. S33–S36, 2002. View at Google Scholar · View at Scopus
  15. B. J. Bahnson, V. E. Anderson, and G. A. Petsko, “Structural mechanism of enoyl-CoA hydratase: three atoms from a single water are added in either an E1cb stepwise or concerted fashion,” Biochemistry, vol. 41, no. 8, pp. 2621–2629, 2002. View at Publisher · View at Google Scholar · View at Scopus
  16. G. A. Mills and V. Walker, “Headspace solid-phase microextraction profiling of volatile compounds in urine: application to metabolic investigations,” Journal of Chromatography B: Biomedical Sciences and Applications, vol. 753, no. 2, pp. 259–268, 2001. View at Publisher · View at Google Scholar · View at Scopus
  17. P. Dirinck and A. De Winne, “Flavour characterisation and classification of cheeses by gas chromatographic-mass spectrometric profiling,” Journal of Chromatography A, vol. 847, no. 1-2, pp. 203–208, 1999. View at Publisher · View at Google Scholar · View at Scopus
  18. G. Yu, T. T. H. Nguyen, Y. Guo et al., “Enzymatic functions of wild tomato methylketone synthases 1 and 2,” Plant Physiology, vol. 15, no. 1, pp. 67–77, 2010. View at Google Scholar
  19. H. B. Lukins and J. W. Foster, “Methyl ketone metabolism in hydrocarbon-utilizing mycobacteria,” Journal of Bacteriology, vol. 85, no. 5, pp. 1074–1087, 1963. View at Google Scholar · View at Scopus
  20. D. H. Hwang, Y. J. Lee, and J. E. Kinsella, “β Ketoacyl decarboxylase activity in spores and mycelium of Penicillium roqueforti,” International Journal of Biochemistry, vol. 7, no. 3-4, pp. 165–171, 1976. View at Google Scholar · View at Scopus
  21. S. Fadda, S. Leroy-Sétrin, and R. Talon, “Preliminary characterization of β-decarboxylase activities in Staphylococcus carnosus 833, a strain used in sausage fermentation,” FEMS Microbiology Letters, vol. 228, no. 1, pp. 143–149, 2003. View at Publisher · View at Google Scholar · View at Scopus
  22. H. Hajjaj, A. Klaébé, G. Goma, P. J. Blanc, E. Barbier, and J. François, “Medium-chain fatty acids affect citrinin production in the filamentous fungus Monascus ruber,” Applied and Environmental Microbiology, vol. 66, no. 3, pp. 1120–1125, 2000. View at Publisher · View at Google Scholar · View at Scopus
  23. T. Yagi, A. Hatano, T. Hatano, F. Fukui, and S. Fukui, “A novel enzyme system: The n-alkane-2-one-forming enzyme system in Penicillium decumbens IFO-7091,” Journal of Fermentation and Bioengineering, vol. 71, no. 6, pp. 439–441, 1991. View at Publisher · View at Google Scholar · View at Scopus
  24. R. Walker, R. J. Flanagan, M. S. Lennard, G. A. Mills, and V. Walker, “Solid-phase microextraction: investigation of the metabolism of substances that may be abused by inhalation,” Journal of Chromatographic Science, vol. 44, no. 7, pp. 387–393, 2006. View at Google Scholar · View at Scopus
  25. F. Björkling, H. Frykman, S. E. Godtfredsen, and O. Kirk, “Lipase catalyzed synthesis of peroxycarboxylic acids and lipase mediated oxidations,” Tetrahedron, vol. 48, no. 22, pp. 4587–4592, 1992. View at Publisher · View at Google Scholar · View at Scopus
  26. P. Chaiyen, M. W. Fraaije, and A. Mattevi, “The enigmatic reaction of flavins with oxygen,” Trends in Biochemical Sciences, vol. 37, no. 9, pp. 373–380, 2012. View at Google Scholar
  27. C. Kendall and E. A. Caldwell, “Fundamentals of stable isotope geochemistry,” in Isotope Tracers in Catchment Hydrology, C. Kendall and J. J. McDowell, Eds., pp. 51–86, Elsevier Science, Amsterdam, The Netherlands, 1998. View at Google Scholar
  28. A. Gurvitz and H. Rottensteiner, “The biochemistry of oleate induction: transcriptional upregulation and peroxisome proliferation,” Biochimica et Biophysica Acta—Molecular Cell Research, vol. 1763, no. 12, pp. 1392–1402, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. J. M. Jones, K. Nau, M. T. Geraghty, R. Erdmann, and S. J. Gould, “Identification of peroxisomal Acyl-CoA thioesterases in yeast and humans,” The Journal of Biological Chemistry, vol. 274, no. 14, pp. 9216–9223, 1999. View at Publisher · View at Google Scholar · View at Scopus
  30. P. P. van Veldhoven, “Biochemistry and genetics of inherited disorders of peroxisomal fatty acid metabolism,” Journal of Lipid Research, vol. 51, no. 10, pp. 2863–2895, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. S. Kersten, J. Seydoux, J. M. Peters, F. J. Gonzalez, B. Desvergne, and W. Wahli, “Peroxisome proliferator-activated receptor α mediates the adaptive response to fasting,” The Journal of Clinical Investigation, vol. 103, no. 11, pp. 1489–1498, 1999. View at Google Scholar · View at Scopus
  32. M. Rakhshandehroo, B. Knoch, M. Müller, and S. Kersten, “Peroxisome proliferator-activated receptor alpha target genes,” PPAR Research, vol. 2010, Article ID 612089, 20 pages, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. B. Vitali, M. Ndagijimana, F. Cruciani et al., “Impact of a synbiotic food on the gut microbial ecology and metabolic profiles,” BMC Microbiology, vol. 10, article 4, 2010. View at Publisher · View at Google Scholar · View at Scopus
  34. P. P. van Veldhoven, G. Vanhove, S. Assselberghs, H. J. Eyssen, and G. P. Mannaerts, “Substrate specificities of rat liver peroxisomal acyl-CoA oxidases: palmitoyl-CoA oxidase (inducible acyl-CoA oxidase), pristanoyl-CoA oxidase (non-inducible acyl-CoA oxidase), and trihydroxycoprostanoyl-CoA oxidase,” The Journal of Biological Chemistry, vol. 267, no. 28, pp. 20065–20074, 1992. View at Google Scholar · View at Scopus
  35. R. J. A. Wanders, P. G. Barth, and H. A. S. Heymans, “Single peroxisomal enzyme deficiencies,” in The Metabolic & Molecular Bases of Inherited Disease, C. R. Scriver, A. L. Beaudet, W. S. Sly, and D. Valle, Eds., vol. 2, pp. 3219–3256, McGraw-Hill, New York, NY, USA, 8th edition, 2001. View at Google Scholar
  36. S. Ferdinandusse, S. Denis, C. W. T. van Roermund, R. J. A. Wanders, and G. Dacremont, “Identification of the peroxisomal β-oxidation enzymes involved in the degradation of long-chain dicarboxylic acids,” Journal of Lipid Research, vol. 45, no. 6, pp. 1104–1111, 2004. View at Publisher · View at Google Scholar · View at Scopus