Production of prostaglandins, isoprostanes and thromboxane by Aspergillus fumigatus: Identification by gas chromatography-tandem mass spectrometry and quantification by enzyme immunoassay

Molecular Immunology

Volumn 49, Issue 4, 2012, Pages 621-627

  Kupfahl, Claudio ^a   Tsikas, Dimitrios ^b   Niemann, Jonas ^b   Geginat, Gernot ^a   Hof, Herbert ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

A. fumigatus; Eicosanoids; Pulmonary disease

Indexed keywords

ACETYLSALICYLIC ACID; BRONCHOCONSTRICTING AGENT; EBSELEN; ICOSANOID; INDOMETACIN; ISOPROSTANE; LIPOXYGENASE; NORDIHYDROGUAIARETIC ACID; PROSTACYCLIN; PROSTAGLANDIN; PROSTAGLANDIN F1 ALPHA; PROSTAGLANDIN F2 ALPHA; PROSTAGLANDIN SYNTHASE; THROMBOXANE; THROMBOXANE B2;

ARTICLE; ASPERGILLUS FUMIGATUS; BIOSYNTHESIS; CELL LYSATE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS REACTION; DERIVATIZATION; ENZYME ACTIVITY; ENZYME IMMUNOASSAY; GAS CHROMATOGRAPHY; HYDROLYSIS; LIMIT OF QUANTITATION; LUNG DISEASE; NONHUMAN; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ARACHIDONIC ACID; ASPERGILLOSIS; ASPERGILLUS FUMIGATUS; AZOLES; EICOSANOIDS; ETHER, ETHYL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; IMMUNOENZYME TECHNIQUES; ISOPROSTANES; ORGANOSELENIUM COMPOUNDS; PROSTAGLANDINS; TANDEM MASS SPECTROMETRY; THROMBOXANES;

ASPERGILLUS FUMIGATUS; FUNGI; MAMMALIA;

EID: 84655167113     PISSN: 01615890     EISSN: 18729142     Source Type: Journal    
DOI: 10.1016/j.molimm.2011.10.010     Document Type: Article

References (28)

1. Barnes P.J., Chung K.F., Page C.P. Inflammatory mediators of asthma: an update. Pharmacol. Rev. 1998, 50:515-596.
2. Birch M., Robson G., Law D., Denning D.W. Evidence of multiple extracellular phospholipase activities of Aspergillus fumigatus. Infect. Immun. 1996, 64:751-755.
3. Butovich I.A., Luk'yanova S.M., Reddy C.C. Oxidation of linoleyl alcohol by potato tuber lipoxygenase: kinetics and positional, stereo, and geometrical (cis, trans) specificity of the reaction. Arch. Biochem. Biophys. 2000, 378:65-77.
4. Butovich I.A., Reddy C.C. Enzyme-catalyzed and enzyme-triggered pathways in dioxygenation of 1-monolinoleoyl-rac-glycerol by potato tuber lipoxygenase. Biochim. Biophys. Acta 2001, 1546:379-398.
5. Erb-Downward J.R., Huffnagle G.B. Cryptococcus neoformans produces authentic prostaglandin E2 without a cyclooxygenase. Eukaryot. Cell 2007, 6:346-350.
6. Erb-Downward J.R., Noverr M.C. Characterization of prostaglandin E2 production by Candida albicans. Infect. Immun. 2007, 75:3498-3505.
7. Funk C.D. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001, 294:1871-1875.
8. Gao L., Zackert W.E., Hasford J.J., Danekis M.E., Milne G.L., Remmert C., Reese J., Yin H., Tai H.H., Dey S.K., Porter N.A., Morrow J.D. Formation of prostaglandins E2 and D2 via the isoprostane pathway: a mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J. Biol. Chem. 2003, 278:28479-28489.
9. Gibson P.G. Allergic bronchopulmonary aspergillosis. Semin. Respir. Crit. Care Med. 2006, 27:185-191.
10. Kraemer R., Delosea N., Ballinari P., Gallati S., Crameri R. Effect of allergic bronchopulmonary aspergillosis on lung function in children with cystic fibrosis. Am. J. Respir. Crit. Care Med. 2006, 174:1211-1220.
11. Lu J.M., Nurko J., Weakley S.M., Jiang J., Kougias P., Lin P.H., Yao Q., Chen C. Molecular mechanisms and clinical applications of nordihydroguaiaretic acid (NDGA) and its derivatives: an update. Med. Sci. Monit. 2010, 16:RA93-RA100.
12. Maiorino M., Roveri A., Coassin M., Ursini F. Kinetic mechanism and substrate specificity of glutathione peroxidase activity of ebselen (PZ51). Biochem. Pharmacol. 1988, 37:2267-2271.
13. Miller S.B. Prostaglandins in health and disease: an overview. Semin. Arthritis Rheum. 2006, 36:37-49.
14. Morrow J.D. The isoprostanes - unique products of arachidonate peroxidation: their role as mediators of oxidant stress. Curr. Pharm. Des. 2006, 12:895-902.
15. Noverr M.C., Erb-Downward J.R., Huffnagle G.B. Production of eicosanoids and other oxylipins by pathogenic eukaryotic microbes. Clin. Microbiol. Rev. 2003, 16:517-533.
16. Noverr M.C., Toews G.B., Huffnagle G.B. Production of prostaglandins and leukotrienes by pathogenic fungi. Infect. Immun. 2002, 70:400-402.
17. Parnham M.J., Kindt S. A novel biologically active seleno-organic compound. III. Effects of PZ 51 (ebselen) on glutathione peroxidase and secretory activities of mouse macrophages. Biochem. Pharmacol. 1984, 33:3247-3250.
18. Rolin S., Masereel B., Dogne J.M. Prostanoids as pharmacological targets in COPD and asthma. Eur. J. Pharmacol. 2006, 533:89-100.
19. Schewe T. Molecular actions of ebselen-an antiinflammatory antioxidant. Gen. Pharmacol. 1995, 26:1153-1169.
20. Schmidt L.M., Belvisi M.G., Bode K.A., Bauer J., Schmidt C., Suchy M.T., Tsikas D., Scheuerer J., Lasitschka F., Grone H.J., Dalpke A.H. Bronchial epithelial cell-derived prostaglandin E2 dampens the reactivity of dendritic cells. J. Immunol. 2011, 186:2095-2105.
21. Sies H., Masumoto H. Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite. Adv. Pharmacol. 1997, 38:229-246.
22. Stichtenoth D.O., Marhauer V., Tsikas D., Gutzki F.M., Frolich J.C. Effects of specific COX-2-inhibition on renin release and renal and systemic prostanoid synthesis in healthy volunteers. Kidney Int. 2005, 68:2197-2207.
23. Tsikas D. Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to assess in vivo synthesis of prostaglandins, thromboxane, leukotrienes, isoprostanes and related compounds in humans. J. Chromatogr. B: Biomed. Sci. Appl. 1998, 717:201-245.
24. 2 through derivatization by O-(2,3,4,5,6-pentafluorobenzyl)hydroxyl amine. Anal. Biochem. 1998, 261:230-232.
25. Tsikas D., Schwedhelm E., Suchy M.T., Niemann J., Gutzki F.M., Erpenbeck V.J., Hohlfeld J.M., Surdacki A., Frolich J.C. Divergence in urinary 8-iso-PGF(2alpha) (iPF(2alpha)-III, 15-F(2t)-IsoP) levels from gas chromatography-tandem mass spectrometry quantification after thin-layer chromatography and immunoaffinity column chromatography reveals heterogeneity of 8-iso-PGF(2alpha). Possible methodological, mechanistic and clinical implications. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2003, 794:237-255.
26. Tsitsigiannis D.I., Bok J.W., Andes D., Nielsen K.F., Frisvad J.C., Keller N.P. Aspergillus cyclooxygenase-like enzymes are associated with prostaglandin production and virulence. Infect. Immun. 2005, 73:4548-4559.
27. Tsitsigiannis D.I., Keller N.P. Oxylipins as developmental and host-fungal communication signals. Trends Microbiol. 2007, 15:109-118.
28. Vancheri C., Mastruzzo C., Sortino M.A., Crimi N. The lung as a privileged site for the beneficial actions of PGE2. Trends Immunol. 2004, 25:40-46.