Comparative study on the metabolism of the ergot alkaloids ergocristine, ergocryptine, ergotamine, and ergovaline in equine and human S9 fractions and equine liver preparations

References

• Bauermeister A, Aguiar FA, Marques LM, et al. (2016). In vitro metabolism evaluation of the ergot alkaloid dihydroergotamine: application of microsomal and biomimetic oxidative model. Planta Med 82:1368–73.
   PubMed Web of Science ®Google Scholar
• Bicalho B, Giolo JM, Lilla S, DE Nucci G. (2008). Identification and human pharmacokinetics of dihydroergotoxine metabolites in man: preliminary results. Biopharm Drug Dispos 29:17–28.
   PubMed Web of Science ®Google Scholar
• Bicalho B, Guzzo GC, Lilla S, et al. (2005). Pharmacokinetics of dihydroergocristine and its major metabolite 8′-hydroxy-dihydroergocristine in human plasma. Curr Drug Metab 6:519–29.
   PubMed Web of Science ®Google Scholar
• Bony S, Durix A, Leblond A, Jaussaud P. (2001). Toxicokinetics of ergovaline in the horse after an intravenous administration. Vet Res 32:509–13.
   PubMed Web of Science ®Google Scholar
• Chen G, Daaro I, Pramanik BN, Piwinski JJ. (2009). Structural characterization of in vitro rat liver microsomal metabolites of antihistamine desloratadine using LTQ-Orbitrap hybrid mass spectrometer in combination with online hydrogen/deuterium exchange HR-LC/MS. J Mass Spectrom 44:203–13.
   PubMed Web of Science ®Google Scholar
• Coles R, Kharasch ED. (2007). Stereoselective analysis of bupropion and hydroxybupropion in human plasma and urine by LC/MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci 857:67–75.
   PubMed Web of Science ®Google Scholar
• Cross DL, Redmond LM, Strickland JR. (1995). Equine fescue toxicosis: signs and solutions. J Anim Sci 73:899–908.
   PubMed Web of Science ®Google Scholar
• Duringer JM, Lewis R, Kuehn L, et al. (2005). Growth and hepatic in vitro metabolism of ergotamine in mice divergently selected for response to endophyte toxicity. Xenobiotica 35:531–48.
   PubMed Web of Science ®Google Scholar
• Garner GB, Rottinghaus GE, Cornell CN, Testereci H. (1993). Chemistry of compounds associated with endophyte grass interaction - ergovaline-related and ergopeptine-related alkaloids. Agric Ecosyst Environ 44:65–80.
   Web of Science ®Google Scholar
• Gooneratne SR, Patchett BJ, Wellby M, Fletcher LR. (2012). Excretion of loline alkaloids in urine and faeces of sheep dosed with meadow fescue (Festuca pratensis) seed containing high concentrations of loline alkaloids. N Z Vet J 60:176–82.
   PubMed Web of Science ®Google Scholar
• Holcapek M, Kolarova L, Nobilis M. (2008). High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites. Anal Bioanal Chem 391:59–78.
   PubMed Web of Science ®Google Scholar
• Klotz JL, Kirch BH, Aiken GE, et al. (2008). Effects of selected combinations of tall fescue alkaloids on the vasoconstrictive capacity of fescue-naive bovine lateral saphenous veins. J Anim Sci 86:1021–8.
   PubMed Web of Science ®Google Scholar
• Knych HKD, Shields CD, Buckpitt AR, Stanley SD. (2009a). Equine cytochrome P450 2C92: cDNA cloning, expression and initial characterization. Arch Biochem Biophys 485:49–55.
   PubMed Web of Science ®Google Scholar
• Knych HKD, Shields CED, Stanley SD. (2009b). Characterization of CYP3A mediated metabolism in the equine liver. J Vet Pharmacol Ther 32:84–5.
   Web of Science ®Google Scholar
• Knych HKD, Stanley SD. (2008). Complementary DNA cloning, functional expression and characterization of a novel cytochrome P450, CYP2D50, from equine liver. Biochem Pharmacol 76:904–11.
   PubMed Web of Science ®Google Scholar
• Kwok KY, Chan GHM, Kwok WH, et al. (2017). In vitro phase I metabolism of selective estrogen receptor modulators in horse using ultra-high performance liquid chromatography-high resolution mass spectrometry. Drug Test Anal 9:1349–62.
   PubMed Web of Science ®Google Scholar
• Lehner AF, Craig M, Fannin N, et al. (2004). Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry. J Mass Spectrom 39:1275–86.
   PubMed Web of Science ®Google Scholar
• Martinez-Ramirez JA, Walther G, Peters FT. (2015). Studies on drug metabolism by fungi colonizing decomposing human cadavers. Part II: biotransformation of five model drugs by fungi isolated from post-mortem material. Drug Test Anal 7:265–79.
   PubMed Web of Science ®Google Scholar
• Mas-Chamberlin C, Bromet N, Olgiati V, et al. (1997). Metabolism study of dihydro-alpha-ergocryptine,9,10-[9,10-3H(N)] in rat and human hepatocyte cultures and rat, monkey, and human microsomes. Am J Ther 4:291–9.
   PubMedGoogle Scholar
• Maurer G, Frick W. (1984). Elucidation of the structure and receptor binding studies of the major primary, metabolite of dihydroergotamine in man. Eur J Clin Pharmacol 26:463–70.
   PubMed Web of Science ®Google Scholar
• Maurer G, Schreier E, Delaborde S, et al. (1982). Fate and disposition of bromocriptine in animals and man. I: structure elucidation of the metabolites. Eur J Drug Metab Pharmacokinet 7:281–92.
   PubMed Web of Science ®Google Scholar
• Meyer MR, Maurer HH. 2011. Current knowledge of the isoenzymes involved in the metabolism and transport of frequently abused opioids, anesthetics, cognitive enhancers, plant-derived hallucinogens, and of nicotine with aspects on pharmacogenomics. Pharmacogenomics 12:215.
   PubMed Web of Science ®Google Scholar
• Michely JA, Brandt SD, Meyer MR, Maurer HH. (2017). Biotransformation and detectability of the new psychoactive substances N,N-diallyltryptamine (DALT) derivatives 5-fluoro-DALT, 7-methyl-DALT, and 5,6-methylenedioxy-DALT in urine using GC-MS, LC-MSn, and LC-HR-MS/MS . Anal Bioanal Chem 409:1681–95.
   PubMed Web of Science ®Google Scholar
• Michely JA, Helfer AG, Brandt SD, et al. (2015). Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS. Anal Bioanal Chem 407:7831–42.
   PubMed Web of Science ®Google Scholar
• Moubarak AS, Rosenkrans CF. JR. (2000). Hepatic metabolism of ergot alkaloids in beef cattle by cytochrome P450. Biochem Biophys Res Commun 274:746–9.
   PubMed Web of Science ®Google Scholar
• Mulac D, Grote AK, Kleigrewe K, Humpf HU. (2011). Investigation of the metabolism of ergot alkaloids in cell culture by fourier transformation mass spectrometry. J Agric Food Chem 59:7798–807.
   PubMed Web of Science ®Google Scholar
• Orton DA, Richardson RJ. (1982). Ergotamine absorption and toxicity. Postgrad Med J 58:6–11.
   PubMed Web of Science ®Google Scholar
• Passie T, Halpern JH, Stichtenoth DO, et al. (2008). The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther 14:295–314.
   PubMed Web of Science ®Google Scholar
• Peiris DM, Lam W, Michael S, Ramanathan R. (2004). Distinguishing N-oxide and hydroxyl compounds: impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions. J Mass Spectrom 39:600–6.
   PubMed Web of Science ®Google Scholar
• Ramanathan R, Su AD, Alvarez N, et al. (2000). Liquid chromatography/mass spectrometry methods for distinguishing N-oxides from hydroxylated compounds. Anal Chem 72:1352–9.
   PubMed Web of Science ®Google Scholar
• Richter LHJ, Flockerzi V, Maurer HH, Meyer MR. (2017). Pooled human liver preparations, HepaRG, or HepG2 cell lines for metabolism studies of new psychoactive substances? A study using MDMA, MDBD, butylone, MDPPP, MDPV, MDPB, 5-MAPB, and 5-API as examples. J Pharm Biomed Anal 143:32–42.
   PubMed Web of Science ®Google Scholar
• Rudolph W, Remane D, Wissenbach DK, Peters FT. (2018). Development and validation of an ultrahigh performance liquid chromatography-high resolution tandem mass spectrometry assay for nine toxic alkaloids from endophyte-infected pasture grasses in horse serum. J Chromatogr A 1560:35–44.
   PubMed Web of Science ®Google Scholar
• Sauer C, Peters FT, Haas C, et al. (2009). New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J Mass Spectrom 44:952–64.
   PubMed Web of Science ®Google Scholar
• Schmitz A, Zielinski J, Dick B, Mevissen M. (2014). In vitro metabolism of testosterone in the horse liver and involvement of equine CYPs 3A89, 3A94 and 3A95. J Vet Pharmacol Ther 37:338–47.
   PubMed Web of Science ®Google Scholar
• Schumann B, Lebzien P, Ueberschär K-H, Dänicke S. (2009). Effects of the level of feed intake and ergot contaminated concentrate on ergot alkaloid metabolism and carry over into milk. Mol Nutr Food Res 53:931–8.
   PubMed Web of Science ®Google Scholar
• Staack RF, Maurer HH. (2005). Metabolism of designer drugs of abuse. Curr Drug Metab 6:259–74.
   PubMed Web of Science ®Google Scholar
• Strickland JR, Aiken GE, Spiers DE, et al. (2009). Physiological basis of fescue toxicosis. In: Fribourg HA, Hannaway DB, West CP, eds. Tall fescue for the twenty-first century. Agronomy monographs 53. Madison: American Society of Agronomy, Crop Science Society of America, Soil Science Society of America, p. 203–27.
   Google Scholar
• Strickland JR, Looper ML, Matthews JC, et al. (2011). Board-invited review: St. Anthony’s Fire in livestock: causes, mechanisms, and potential solutions. J Anim Sci 89:1603–26.
   PubMed Web of Science ®Google Scholar
• Stuedemann JA, Hill NS, Thompson FN, et al. (1998). Urinary and biliary excretion of ergot alkaloids from steers that grazed endophyte-infected tall fescue. J Anim Sci 76:2146–54.
   PubMed Web of Science ®Google Scholar
• Tyden E, Lofgren M, Hakhverdyan M, et al. (2013). The genes of all seven CYP3A isoenzymes identified in the equine genome are expressed in the airways of horses. J Vet Pharmacol Ther 36:370–5.
   PubMed Web of Science ®Google Scholar
• Xue W, Warshawsky D. (2005). Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: a review. Toxicol Appl Pharmacol 206:73–93.
   PubMed Web of Science ®Google Scholar