Pyrrolizidine alkaloids in food and feed on the Belgian market

References

• [ANZFA] Australia New Zealand Food Authority. 2001. Pyrrolizidine alkaloids in food. A toxicological review and risk assessment. Available from: http://www.anzfa.gov.au
   Google Scholar
• Avula B, Wang Y-H, Wang M, Smillie TJ, Khan IA. 2012. Simultaneous determination of sesquiterpenes and pyrrolizidine alkaloids from the rhizomes of Petasites hybridus (L.) G.M. et Sch. and dietary supplements using UPLC-UV and HPLC-TOF-MS methods. J Pharm Biomed Anal. 70:53–63.
   PubMed Web of Science ®Google Scholar
• Beales KA, Betteridge K, Colegate SM, Edgar JA. 2004. Solid-phase extraction and LC−MS analysis of pyrrolizidine alkaloids in honeys. J Agric Food Chem. 52:6664–6672.
   PubMed Web of Science ®Google Scholar
• Berset D, Brenneisen R, Mathieu C. 2010. Analysis of llicit and illicit drugs in waste, surface and lake water samples using large volume direct injection high performance liquid Chromatography-Electrospray tandem mass spectrometry (HPLC–MS/MS). Chemosphere. 81:859–866.
   PubMed Web of Science ®Google Scholar
• Betteridge K, Cao Y, Colegate SM. 2005. Improved method for extraction and LC-MS analysis of pyrrolizidine alkaloids and their N-oxides in honey: application to Echium vulgare honeys. J Agric Food Chem. 53:1894–1902.
   PubMed Web of Science ®Google Scholar
• BfR. 2011. Chemical analysis and toxicity of pyrrolizidine alkaloids and assessment of the health risks posed by their occurrence in honey. Opinion No. 038/2011 of the BfR from 11 August 2011. Berlin: Bundesamt für Risikobewertung.
   Google Scholar
• BfR. 2013. Pyrrolizidine alkaloids in herbal teas and teas. BfR Opinion No. 018/2013. Berlin: Bundesamt für Risikobewertung.
   Google Scholar
• Bodi D, Ronczka S, Gottschalk C, Behr N, Skibba A, Wagner M, Lahrssen-Wiederholt M, Preiss-Weigert A, These A. 2014. Determination of pyrrolizidine alkaloids in tea, herbal drugs and honey. Food Addit Contam: Part A. 31:1886–1895.
   PubMed Web of Science ®Google Scholar
• Boix C, Ibáñez M, Sancho J, Rambla J, Aranda J, Ballester S, Hernández F. 2015. Fast determination of 40 drugs in water using large volume direct injection liquid chromatography-tandem mass spectrometry. Talanta. 131:719–727.
   PubMed Web of Science ®Google Scholar
• Bolechová M, Čáslavský J, Pospíchalová M, Kosubová P. 2015. UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed. Food Chem. 170:265–270.
   PubMed Web of Science ®Google Scholar
• Boppré M, Colegate SM, Edgar JA. 2005. Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen. J Agric Food Chem. 53:594–600.
   PubMed Web of Science ®Google Scholar
• Bosi CF, Rosa DW, Grougnet R, Lemonakis N, Halabalaki M, Skaltsounis AL, Biavatti MW. 2013. Pyrrolizidine alkaloids in medicinal tea ofAgeratum conyzoides. Rev Bras Farmacogn. 23:425–432.
   Google Scholar
• Bundesgesetzblatt. 1994. Verordnung des Bundesministers für Gesundheit, Sport und Konsumentenschutz vom 21. Juli 1994 betreffend Arzneimittel, die nicht in Verkehr gebracht werden dürfen. 555/1994. Vienna: Bundesanziger Verlag.
   Google Scholar
• Candrian U, Zweifel U, Luethy J, Schlatter C. 1991. Transfer of orally administered 3H-seneciphylline into cow’s milk. J Agric Food Chem. 39:930–933.
   Web of Science ®Google Scholar
• Cao Y, Colegate SM, Edgar JA. 2013. Persistence of echimidine, a hepatotoxic pyrrolizidine alkaloid, from honey into mead. J Food Compos Anal. 29:106–109.
   Web of Science ®Google Scholar
• Cheeke PR. 1985. Toxicity and metabolism of pyrrolizidine alkaloids. J Anim Sci. 66:2343–2350.
   Google Scholar
• Cheng D, Kirk H, Vrieling K, Mulder PP, Klinkhamer PG. 2011. The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F2 hybrids of jacobaea vulgaris and jacobaea aquatica. J Chem Ecol. 37:1071–1080.
   PubMed Web of Science ®Google Scholar
• Chiaia AC, Banta-Green C, Field J. 2008. Eliminating solid phase extraction with large-volume injection LC/MS/MS: analysis of illicit and legal drugs and human urine indicators in U.S. wastewaters. Environ Sci Technol. 42:8841–8848.
   PubMed Web of Science ®Google Scholar
• Commission directive. 2002. Directive 2002/32/EC of the European parliament and of the council of 7 May 2002 on undesirable substances in animal feed [Internet]. European Parliament, Council of the European Union [cited 2015 Oct 13]. Available from: http://eur-lex.europa.eu/legal-content/EN/TXT/HTML/?uri=URISERV:l12069&from=NL
   Google Scholar
• COT. 2008. COT statement on pyrrolizidine alkaloids in food. Committee on toxicity of chemicals in food, consumer products and the environment. Available from: cot.food.gov.uk/pdfs/cotstatementpa200806.pdf
   Google Scholar
• Couet CE, Crews C, Hanley AB. 1996. Analysis, separation and bioassay of pyrrolizidine alkaloids from comfrey (Symphytum officinale). Nat Toxins. 4:163–167.
   PubMedGoogle Scholar
• Court M. 2013. Canine Cytochrome P-450 Pharmacogenetics. Vet Clin North Am Small Anim Pract. 43:1027–1038.
   PubMed Web of Science ®Google Scholar
• Cramer L, Schiebel H-M, Ernst L, Beuerle T. 2013. Pyrrolizidine alkaloids in the food chain: development, validation, and application of a new HPLC-ESI-MS/MS sum parameter method. J Agric Food Chem. 61:11382–11391.
   PubMed Web of Science ®Google Scholar
• Crews C, Startin JR, Clarke PA. 1997. Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS. Food Addit Contam. 14:419–428.
   PubMedGoogle Scholar
• Culvenor CC, Edgar JA, Jago MV, Outteridge A, Peterson JE, Smith LW. 1976. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure. Chem Biol Interact. 12:299–324.
   PubMed Web of Science ®Google Scholar
• Culvenor CC, Edgar JA, Smith LW, Kumana CR, Lin HJ. 1986. Heliotropium lasiocarpum Fisch and Mey identified as cause of veno-occlusive disease due to a herbal tea. Lancet. 327:978.
   Google Scholar
• de Nijs M, Elbers IJW, Mulder PPJ. 2014. Inter-laboratory comparison study for pyrrolizidine alkaloids in animal feed using spiked and incurred material. Food Addit Contam: Part A. 31:288–299.
   PubMed Web of Science ®Google Scholar
• Dübecke A, Beckh G, Lüllmann C. 2011. Pyrrolizidine alkaloids in honey and bee pollen. Food Addit Contam: Part A. 28:348–358.
   Web of Science ®Google Scholar
• Edgar JA, Roeder E, Molyneux RJ. 2002. Honey from plants containing pyrrolizidine alkaloids: a potential threat to health. J Agric Food Chem. 50:2719–2730.
   PubMed Web of Science ®Google Scholar
• EFSA. 2007. Opinion of the scientific panel on contaminants in the food chain on a request from the European Commission related to pyrrolizidine alkaloids as undesirable substances in animal feed. The EFSA J. 447:1–51.
   Google Scholar
• EFSA. 2011. Scientific opinion on pyrrolizidine alkaloids in food and feed. EFSA J. 9:2406.
   Google Scholar
• European Commission. 2002. Commission Decision 2002/657/EC, Commission Decision of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results [Internet]. European Parliament, Council of the European Union [cited 2015 Oct 13]. Available from: http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32002D0657&from=IT
   Google Scholar
• European Commission. 2006. Commission Decision 401/2006/EC Commission regulation (EC) No 401/2006 of 23 February 2006 laying down the methods of sampling and analysis for the official control of the levels of mycotoxins in foodstuffs [Internet]. European Parliament, Council of the European Union [cited 2015 Oct 13]. Available from: http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32006R0401&from=EN
   Google Scholar
• [FAO/WHO] Food and Agriculture Organization/World Health Organization. 2011. Discussion paper on pyrrolizidine alkaloids, Joint FAO/WHO food standards programme, CODEX Committee on Contaminants in Foods, 5th Session; 2011 Mar 21–25; The Hague. Available from: ftp://ftp.fao.org/codex/meetings/CCCF/cccf5/cf05_INF.pdf
   Google Scholar
• Fu PP, Xia Q, Lin G, Chou MW. 2002. Genotoxic pyrrolizidine alkaloids — mechanisms leading to DNA adduct formation and tumorigenicity. Int J Mol Sci. 3:948–964.
   Web of Science ®Google Scholar
• Fu PP, Xia Q, Lin G, Chou MW. 2004. Pyrrolizidine alkaloids—genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metabol Revs. 36:1–55.
   PubMed Web of Science ®Google Scholar
• Gardner DR, Thorne S, Molyneux RJ, Pfister JA, Seawright AA. 2006. Pyrrolizidine alkaloids in Senecio madagascariensis from Australia and Hawaii and assessment of possible livestock poisoning. Biochem Syst Ecol. 34:736–744.
   Web of Science ®Google Scholar
• Goeger PR, Cheeke JA, Schmitz DR, Buhler DR. 1983. Effect of feeding milk from goats fed tansy ragwort (Senecio jacobaea) to rats and calves. Am J Vet Res. 43:1631–1633.
   Web of Science ®Google Scholar
• Griffin CT, Danaher M, Elliott CT, Glenn KD, Furey A. 2013. Detection of pyrrolizidine alkaloids in commercial honey using liquid chromatography-ion trap mass spectrometry. Food Chem. 136:1577–1583.
   PubMed Web of Science ®Google Scholar
• Griffin CT, Gosetto F, Danaher M, Sabatini S, Furey A. 2014. Development of a fast isocratic LC-MS/MS method for the high-throughput analysis of pyrrolizidine alkaloids in Australian honey. Food Addit Contam: Part A. 31:940–961.
   PubMed Web of Science ®Google Scholar
• Hoogenboom LA, Mulder PP, Zeilmaker MJ, Van Den Top HJ, Remmelink GJ, Brandon EF, Klijnstra M, Meijer GA, Schothorst R, Van Egmond HP. 2011. Carry-over of pyrrolizidine alkaloids from feed to milk in dairy cows. Food Addit Contam: Part A. 28:359–372.
   Web of Science ®Google Scholar
• Kempf M, Beuerle T, Bühringer M, Denner M, Trost D, Von Der Ohe K, Bhavanam VB, Schreier P. 2008. Pyrrolizidine alkaloids in honey: risk analysis by gas chromatography-mass spectrometry. Mol Nutr Food Res. 52:1193–1200.
   PubMed Web of Science ®Google Scholar
• Kempf M, Wittig M, Schönfeld K, Cramer L, Schreier P, Beuerle T. 2011. Pyrrolizidine alkaloids in food: downstream contamination in the food chain caused by honey and pollen. Food Addit Contam: Part A. 28:325–331.
   Web of Science ®Google Scholar
• Lebada R, Schreier A, Scherz S, Resch C, Krenn L, Kop B. 2000. Quantitative analysis of the pyrrolizidine alkaloids senkirkine and senecionine in Tussilago farfara L. by capillary electrophoresis. Phytochem Anal. 11:366–369.
   Web of Science ®Google Scholar
• Martinello M, Cristofoli C, Gallina A, Mutinelli F. 2014. Easy and rapid method for the quantitative determination of pyrrolizidine alkaloids in honey by ultra performance liquid chromatography-mass spectrometry: an evaluation in commercial honey. Food Control. 37:146–152.
   Web of Science ®Google Scholar
• Martínez Bueno MJ, Uclés S, Hernando MD, Fernández-Alba AR. 2011. 2011 development of a solvent-free method for the simultaneous identification/quantification of drugs of abuse and their metabolites in environmental water by LC–MS/MS. Talanta. 85:157–166.
   PubMed Web of Science ®Google Scholar
• Mathon C, Edder P, Bieri S, Christen P. 2014. Survey of pyrrolizidine alkaloids in teas and herbal teas on the Swiss market using HPLC-MS/MS. Anal Bioanal Chem. 406:7345–7354.
   PubMed Web of Science ®Google Scholar
• Matuszewski BK, Constanzer ML, Chavez-Eng CM. 2003. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC−MS/MS. Anal Chem. 75:3019–3030.
   PubMed Web of Science ®Google Scholar
• Mol HG, VanDam RC, Zomer P, Mulder PP. 2011. Screening of plant toxins in food, feed and botanicals using full-scan high-resolution (Orbitrap) mass spectrometry. Food Addit Contam: Part A. 28:1405–1423.
   PubMed Web of Science ®Google Scholar
• Mulder PP, Beumer B, Oosterink E, De Jong J 2009. Dutch survey pyrrolizidine alkaloids in animal forage. Available from: https://www.google.be/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=0CCQQFjAA&url=http%3A%2F%2Fwww.vwa.nl%2Ftxmpub%2Ffiles%2F%3Fp_file_id%3D2000465&ei=PkbsVOXHBIPsO5GZgagK&usg=AFQjCNEPiHXhaS0U781LcjjWF8Xy8A3ULA&bvm=bv.86475890,d.ZWU
   Google Scholar
• Orantes-Bermejo FJ, Serra Bonvehí J, Gómez-Pajuelo A, Megías M, Torres C. 2013. Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper’s bugloss (Echium spp.). Food Addit Contam: Part A. 30:1799–1806.
   PubMed Web of Science ®Google Scholar
• Prakash AS, Pereira TN, Reilly PEB, Seawright AA. 1999. Pyrrolizidine alkaloids in human diet. Mutation Res. 443:53–67.
   PubMed Web of Science ®Google Scholar
• Ridker PM, McDermott WV. 1989. Comfrey herb tea and hepatic veno-occlusive disease. Lancet. 333:657–658.
   Google Scholar
• Robinson B, Gummow B. 2015. A field investigation into a suspected outbreak of pyrrolizidine alkaloid toxicosis in horses in western Queensland. Prev Vet Med. 118:378–386.
   PubMed Web of Science ®Google Scholar
• Roeder E. 2000. Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie. 55:711–772.
   PubMed Web of Science ®Google Scholar
• Schoental R. 1968. Toxicology and carcinogenic action of pyrrolizidine alkaloids. Cancer Res. 28:2237–2246.
   PubMed Web of Science ®Google Scholar
• Schulz M, Meins J, Diemert S, Zagermann-Muncke P, Goebel R, Schrenk D, Schubert-Zsilavecz M, Abdel-Tawab M. 2015. Detection of pyrrolizidine alkaloids in German licensed herbal medicinal teas. Phytomedicine. 22:648–656.
   PubMed Web of Science ®Google Scholar
• Segall HJ. 1978. Pyrrolizidine alkaloids derived from Senecio jacobaea. Toxicol Lett. 1:279–284.
   Web of Science ®Google Scholar
• Stegelmeier BL, Edgar JA, Colegate SM, Gardner DR, Schoch TK, Coulombe RA, Molyneux RJ. 1999. Pyrrolizidine alkaloid plants, metabolism and toxicity. J Natural Toxins. 8:95–116.
   PubMedGoogle Scholar
• These A, Bodi D, Ronczka S, Lahrssen-Wiederholt M, Preiss-Weigert A. 2013. Structural screening by multiple reaction monitoring as a newapproach for tandem mass spectrometry: presented for the determination of pyrrolizidine alkaloids in plants. Anal Bioanal Chem. 405:9375–9383.
   PubMed Web of Science ®Google Scholar
• Van Beusekom CD, Fink-gremmels J, Schrickx JA. 2014. Comparing the glucuronidation capacity of the feline liver with substrate-specific glucuronidation in dogs. J Vet Pharmacol Therap. 37:18–24.
   PubMed Web of Science ®Google Scholar
• WHO. 1988. Pyrrolizidine alkaloids. Environmental health criteria 80. Geneva: World Health Organization.
   Google Scholar
• Wiedenfeld H. 2011. Plants containing pyrrolizidine alkaloids: toxicity and problems. Food Addit Contam: Part A Chem. 28:282–292.
   Web of Science ®Google Scholar
• Wiedenfeld H, Edgar J. 2011. Toxicity of pyrrolizidine alkaloids to humans and ruminants. Phytochem Rev. 10:137–151.
   Web of Science ®Google Scholar
• Xia Q, Chou MW, Edgar JA, Doerge DR, Fu PP. 2006. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. Cancer Lett. 231:138–145.
   PubMed Web of Science ®Google Scholar
• Xia Q, Chou W, Lin G, Fu P. 2004. Metabolic formation of DHP-derived DNA adducts from a representative otonecine type pyrrolizidine alkaloid clivorine and the extract of Ligularia hodgsonnii hook. Chem Res Toxicol. 17:702–708.
   PubMed Web of Science ®Google Scholar
• Xia Q, Ma L, He X, Cai L, Fu P. 2015. 7-Glutathione pyrrole adduct: a potential DNA reactive metabolite of pyrrolizidine alkaloids. Chem Res Toxicol. 28:615–620.
   PubMed Web of Science ®Google Scholar
• Xia Q, Zhao Y, Von Tungeln L, Doerge D, Lin G, Cai L, Fu P. 2013. Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. Chem Res Toxicol. 26:1384–1396.
   PubMed Web of Science ®Google Scholar
• Yoon SH, Kim M-S, Kim SH, Park HM, Pyo H, Lee YM, Lee K-T, Hong J. 2015. Effective application of freezing lipid precipitation and SCX-SPE for determination of pyrrolizidine alkaloids in high lipid foodstuffs by LC-ESI-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 992:56–66.
   PubMed Web of Science ®Google Scholar
• Zhang F, Wanga C, Xionga A, Wanga W, Yanga L, Branford-White C, Wanga Z, Bligh S. 2007. Quantitative analysis of total retronecine esters-type pyrrolizidine alkaloids in plant by high performance liquid chromatography. Anal Chim Acta. 605:94–101.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Xia Q, Gamboa Da Costa G, Yu H, Cai L, Fu P. 2012. Full structure assignments of pyrrolizidine alkaloid DNA adducts and mechanism of tumor initiation. Chem Res Toxicol. 25:1985–1996.
   PubMed Web of Science ®Google Scholar