Investigation of the metabolism of ergot alkaloids in cell culture by fourier transformation mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 14, 2011, Pages 7798-7807

  Mulac, Dennis ^a   Grote, Anna Karina ^a   Kleigrewe, Karin ^a   Humpf, Hans Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

cell lines; ergot alkaloids; FTMS; HepG2; HT 29; metabolism; primary cells

Indexed keywords

CELL LINES; ERGOT ALKALOIDS; FTMS; HEPG2; HT-29; PRIMARY CELLS;

ANIMAL CELL CULTURE; BIOMOLECULES; CELLS; FOURIER ANALYSIS; FOURIER TRANSFORMS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; NITROGEN COMPOUNDS; PHYSIOLOGY; TOXIC MATERIALS;

METABOLITES;

ERGOT ALKALOID; MYCOTOXIN;

BIOLOGICAL MODEL; CELL CULTURE; CELL STRAIN HEPG2; CELL STRAIN HT29; CONFERENCE PAPER; CYTOLOGY; EVALUATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; KIDNEY; LIVER; MASS SPECTROMETRY; METABOLISM; METHODOLOGY;

CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERGOT ALKALOIDS; HEP G2 CELLS; HT29 CELLS; HUMANS; KIDNEY; LIVER; MASS SPECTROMETRY; MODELS, BIOLOGICAL; MYCOTOXINS;

CLAVICEPS PURPUREA; FUNGI; SECALE CEREALE;

EID: 79960609691     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2012024     Document Type: Conference Paper

References (30)

1. Tfelt-Hansen, P.; Saxena, P. R.; Dahlof, C.; Pascual, J.; Lainez, M.; Henry, P.; Diener, H.; Schoenen, J.; Ferrari, M. D.; Goadsby, P. J. Ergotamine in the acute treatment of migraine: a review and european consensus Brain 2000, 123 (Part 1) 9-18 (Pubitemid 30037964)
2. Griffith, R. W.; Grauwiler, J.; Hodel, C.; Leist, K. H.; Matter, B. Toxicologic considerations. In Ergot Alkaloids and Related Compounds; Berde, B.,; Schild, H. O., Eds.; Springer Verlag: Berlin, Germany, 1978; pp 805-851.
3. Schiff, P. L. Ergot and its alkaloids Am J. Pharm. Educ. 2006, 70, 98
4. Eich, E.; Pertz, H. Ergot alkaloids as lead structures for differential receptor systems Pharmazie 1994, 49, 867-877 (Pubitemid 24381203)
5. EFSA Opinion of the scientific panel on contaminants in food chain on a request from the commission related to ergot as undesirable substance in animal feed. EFSA J. 2005, 225, 1-27.
6. Testa, B.; Kramer, S. D. The biochemistry of drug metabolism - an introduction: part 5. Metabolism and bioactivity Chem. Biodivers. 2009, 6, 591-684
7. Eckert, H.; Kiechel, J. R.; Rosenthaler, J.; Schmidt, R.; Schreier, E. Biopharmaceutical aspects, analytical methods, pharmacokinetics, metabolism and bioavailability. In Ergot Alkaloids and Related Compounds; Berde, B.;; Schild, H. O., Eds.; Springer Verlag: Berlin, Germany, 1978; pp 719-803.
8. Maurer, G.; Frick, W. Elucidation of the structure and receptor binding studies of the major primary, metabolite of dihydroergotamine in man Eur. J. Clin. Pharmacol. 1984, 26, 463-470 (Pubitemid 14149126)
9. Duringer, J. M.; Lewis, R.; Kuehn, L.; Fleischmann, T.; Craig, A. M. Growth and hepatic in vitro metabolism of ergotamine in mice divergently selected for response to endophyte toxicity Xenobiotica 2005, 35, 531-548 (Pubitemid 41242912)
10. Moubarak, A. S.; Rosenkrans, C. F., Jr. Hepatic metabolism of ergot alkaloids in beef cattle by cytochrome P450 Biochem. Biophys. Res. Commun. 2000, 274, 746-749 (Pubitemid 30663691)
11. Nimmerfall, F.; Rosenthaler, J. Ergot alkaloids: hepatic distribution and estimation of absorption by measurement of total radioactivity in bile and urine J. Pharmacokinet. Biopharm. 1976, 4, 57-66
12. Slaytor, M. B.; Wright, S. E. The metabolites of ergometrine and lysergic acid diethylamide in rat bile J. Med. Pharm. Chem. 1962, 91, 483-491
13. Komarova, E. L.; Tolkachev, O. N. Medicinal plants: the chemistry of peptide ergot alkaloids. Part 1. Classification and chemistry of ergot peptides Pharm. Chem. J. 2001, 35, 504-513 (Pubitemid 34406547)
14. Stadler, P. A.; Sturmer, E. Comparative studies on the pharmacological properties of stereoisomers of ergotamine and dihydro-ergotamine Naunyn Schmiedebergs Arch. Pharmakol. 1970, 266, 457-458
15. Shappell, N. W.; Smith, D. J. Ergovaline movement across Caco-2 cells In Vitro Cell Dev. Biol. Anim. 2005, 41, 245-251 (Pubitemid 43104608)
16. Mulac, D.; Humpf, H. U. Cytotoxicity and accumulation of ergot alkaloids in human primary cells Toxicology 2011, 282, 112-121
17. Franzmann, C.; Wachter, J.; Dittmer, N.; Humpf, H. U. Ricinoleic acid as a marker for ergot impurities in rye and rye products J. Agric. Food Chem. 2010, 58, 4223-4229
18. Uhlig, S.; Vikoren, T.; Ivanova, L.; Handeland, K. Ergot alkaloids in norwegian wild grasses: a mass spectrometric approach Rapid Commun. Mass Spectrom. 2007, 21, 1651-1660 (Pubitemid 46827114)
19. Königs, M.; Mulac, D.; Schwerdt, G.; Gekle, M.; Humpf, H. U. Metabolism and cytotoxic effects of T-2 toxin and its metabolites on human cells in primary culture Toxicology 2009, 258, 106-115
20. Aellig, W. H.; Nuesch, E. Comparative pharmacokinetic investigations with tritium-labeled ergot alkaloids after oral and intravenous administration man Int. J. Clin. Pharmacol. Biopharm. 1977, 15, 106-112 (Pubitemid 8093835)
21. Sanders, S. W.; Haering, N.; Mosberg, H.; Jaeger, H. Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing Eur. J. Clin. Pharmacol. 1986, 30, 331-334 (Pubitemid 16084209)
22. Ala-Hurula, V.; Myllyla, V. V.; Arvela, P.; Heikkila, J.; Karki, N.; Hokkanen, E. Systemic availability of ergotamine tartrate after oral, rectal and intramuscular administration Eur. J. Clin. Pharmacol. 1979, 15, 51-55 (Pubitemid 9235754)
23. Stange, K.; Pohlmeier, H.; Lübbesmeyer, A.; Gumbinger, G.; Schmitz, W.; Baumgart, P. Vaskulärer Ergotismus durch Getreidestaubinhalation Dtsch. Med. Wschr. 1998, 123, 1547-1550
24. Little, P. J.; Jennings, G. L.; Skews, H.; Bobik, A. Bioavailability of dihydroergotamine in man Br. J. Clin. Pharmacol. 1982, 13, 785-790 (Pubitemid 13139859)
25. Lehner, A. F.; Craig, M.; Fannin, N.; Bush, L.; Tobin, T. Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds J. Mass Spectrom. 2005, 40, 1484-1502 (Pubitemid 41667211)
26. Klotz, J. L.; Kirch, B. H.; Aiken, G. E.; Bush, L. P.; Strickland, J. R. Bioaccumulation of ergovaline in bovine lateral saphenous veins in vitro J. Anim. Sci. 2009, 87, 2437-2447
27. Mohamed, R.; Gremaud, E.; Tabet, J. C.; Guy, P. A. Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments Rapid Commun. Mass Spectrom. 2006, 20, 2787-2799 (Pubitemid 44526614)
28. Zaia, J. Mass spectrometry of oligosaccharides Mass Spectrom. Rev. 2004, 23, 161-227
29. Doostdar, H.; Duthie, S. J.; Burke, M. D.; Melvin, W. T.; Grant, M. H. The influence of culture medium composition on drug metabolising enzyme activities of the human liver derived Hep G2 cell line FEBS Lett. 1988, 241, 15-18 (Pubitemid 19004974)
30. Yoshitomi, S.; Ikemoto, K.; Takahashi, J.; Miki, H.; Namba, M.; Asahi, S. Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology Toxicol. In Vitro 2001, 15, 245-256 (Pubitemid 32476834)