718
Views
37
CrossRef citations to date
0
Altmetric
Original Articles

Investigation of targeted pyrrolizidine alkaloids in traditional Chinese medicines and selected herbal teas sourced in Ireland using LC-ESI-MS/MS

, , , &
Pages 940-961 | Received 12 Jan 2014, Accepted 22 Feb 2014, Published online: 14 Apr 2014

References

  • Allis O, Dauphard J, Hamilton B, Ni Shuilleabhain A, Lehane M, James KJ, Furey A. 2007. Liquid chromatography−tandem mass spectrometry application, for the determination of extracellular hepatotoxins in Irish lake and drinking waters. Anal Chem. 79:3436–3447.
  • Avula B, Wang YH, Wang M, Smillie TJ, Khan IA. 2012. Simultaneous determination of sesquiterpenes and pyrrolizidine alkaloids from rhizomes of Petasites hybridus and dietary supplements using UPLC-MS. Planta Med. 78:PI393.
  • Aydın AA, Letzel T. 2013. Simultaneous investigation of sesquiterpenes, pyrrolizidine alkaloids and N-oxides in Butterbur (Petasites hybridus) with an offline 2D-combination of HPLC-UV and LC-MMI-ToF-MS. J Pharmaceut Biomed Anal. 85:74–82.
  • Bach N, Thung SN, Schaffner F. 1989. Comfrey herb tea-induced hepatic veno-occlusive disease. Am J Med. 87:97–99.
  • Bent S. 2008. Herbal medicine in the United States: review of efficacy, safety, and regulation. J Gen Intern Med. 23:854–859.
  • Betz JM, Eppley RM, Taylor WC, Andrzejewski D. 1994. Determination of pyrrolizidine alkaloids in commercial comfrey products (Symphytum sp.). J Pharm Sci. 83:649–653.
  • Bosi CF, Rosa DW, Grougnet R, Lemonakis N, Halabalaki M, Skaltsounis AL, Biavatti MW. 2013. Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides. Rev bras farmacogn [Internet]; [cited 2013 Jul 29]. Available from: http://www.scielo.br/pdf/rbfar/v23n3/aop02513.pdf
  • Bull L, Culvenor CCJ, Dick A. 1968. The pyrrolizidine alkaloids: their chemistry, pathogenicity and other biological properties. Amsterdam: North Holland Publishing.
  • Bull LB, Dick AT. 1959. The chronic pathological effects on the liver of the rat of the pyrrolizidine alkaloids heliotrine, lasiocarpine, and their N-Oxides. J Pathol Bacteriol. 78:483–502.
  • Bunchorntavakul C, Reddy KR. 2013. Review article: herbal and dietary supplement hepatotoxicity. Aliment Pharmacol Ther. 37:3–17.
  • [BfR] Bundesamt für Risiokobewertung. 2011. Analytik und toxizität von pyrrolizidinalkaloiden sowie eine einschätzung des gerundheitlichen risikos durch deren vorkommen in honig; Stellungnahme Nr. 038/2011 des BfR vom 11 Aug 2011 [Internet]. [cited 2013 Sep 3]. Available from: http://www.bfr.bund.de/cm/343/analytik-und-toxizitaet-von-pyrroli zidinalkaloiden.pdf
  • [BfR] Bundesamt für Risiokobewertung. 2013. Pyrrolizidine alkaloids in herbal teas and teas; Stellungnahme Nr. 018/2013 des BfR vom 5 July 2013 [Internet]. [cited 2013 Sep 3]. Available from: http://www.bfr.bund.de/cm/349/pyrrolizidine-alkaloids-in-herbal-teas-and-teas.pdf
  • Bundesanzeiger. Bekanntmachung über die Zulassung und Registrierung von Arzneimitteln vom 05. June 1992 Abwehr von Arzneimitteln – Stufe II, hier: Arzneimittel, die Pyrrolizidin-Alkaloide mit einem 1,2-ungesättigtem Necin-Gerüst enthalten. BAnz, 1992. 111: p. 4805.
  • Cao Y, Colegate SM, Edgar JA. 2008. Safety assessment of food and herbal products containing hepatotoxic pyrrolizidine alkaloids: interlaboratory consistency and the importance of N-oxide determination. Phytochem Anal. 19:526–533.
  • Capriotti AL, Foglia P, Gubbiotti R, Roccia C, Samperi R, Laganà A. 2010. Development and validation of a liquid chromatography/atmospheric pressure photoionization-tandem mass spectrometric method for the analysis of mycotoxins subjected to commission regulation (EC) No. 1881/2006 in cereals. J Chromatogr A. 1217:6044–6051.
  • Cheeke PR. 1988. Toxicity and metabolism of pyrrolizidine alkaloids. J Anim Sci. 66:2343–2350.
  • [COT] Committee on Toxicity. 2008. Committee on Toxicity of chemicals in food, consumer products and the environment. COT statement on pyrrolizidine alkaloids in food [Internet]; [cited 2011 Dec 13]. Available from: http://cot.food.gov.uk/pdfs/cotstatementpa200806.pdf
  • Crews C, Berthiller F, Krska R. 2010. Update on analytical methods for toxic pyrrolizidine alkaloids. Anal Bioanal Chem. 396:327–338.
  • Dübecke A, Beckh G, Lüllmann C. 2011. Pyrrolizidine alkaloids in honey and bee pollen. Food Addit Contam: Part A. 28:348–358.
  • Edgar JA, Colegate SM, Boppré M, Molyneux RJ. 2011. Pyrrolizidine alkaloids in food: a spectrum of potential health consequences. Food Addit Contam: Part A. 28:308–324.
  • European Commission. 2002. 2002/657/EC. Commission decision implementing council directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Commun L. 221:8–36.
  • European Commission. 2004. 2004/24/EC. Commission directive amending, as regards traditional herbal medicinal products, directive 2001/83/EC on the Community code relating to medicinal products for human use. Off J Eur Commun L. 136:85–90.
  • [EFSA] European Food Safety Authority. 2011. Scientific opinion on pyrrolizidine alkaloids in food and feed. EFSA panel on contaminants in the food chain (CONTAM). EFSA J. 9:1–134.
  • Fernández Puente P, Fidalgo Sáez MJ, Hamilton B, Lehane M, Ramstad H, Furey A, James KJ. 2004. Rapid determination of polyether marine toxins using liquid chromatography–multiple tandem mass spectrometry. J Chromatogr A. 1056:77–82.
  • Fragoso-Serrano M, Figueroa-González G, Castro-Carranza E, Hernández-Solis F, Linares E, Bye R, Pereda-Miranda R. 2012. Profiling of alkaloids and eremophilanes in miracle tea (Packera candidissima and P. bellidifolia) Products. J Nat Prod. 75:890–895.
  • Fu PP, Chiang HM, Xia QS, Chen T, Chen BH, Yin JJ, Wen KC, Lin G, Yu HT. 2009. Quality assurance and safety of herbal dietary supplements. J Environ Sci Health, Part C: Environ Carcinog Ecotoxicol Rev. 27:91–119.
  • Fu PP, Xia QS, Lin G, Chou MW. 2004. Pyrrolizidine alkaloids - genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metab Rev. 36:1–55.
  • Fu PP, Yang YC, Xia QS, Chou MW, Cui YY, Lin G. 2002. Pyrrolizidine alkaloids – Tumorigenic components in Chinese herbal medicines and dietary supplements. J Food Drug Anal. 10:198–211.
  • Furey A, Moriarty M, Bane V, Kinsella B, Lehane M. 2013. Ion suppression; a critical review on causes, evaluation, prevention and applications. Talanta. 115:104–122.
  • Gao H, Li N, Wang JY, Zhang SC, Lin G. 2012. Definitive diagnosis of hepatic sinusoidal obstruction syndrome induced by pyrrolizidine alkaloids. J Dig Dis. 13:33–39.
  • Gilbert-López B, García-Reyes JF, Molina-Díaz A. 2012. Determination of fungicide residues in baby food by liquid chromatography–ion trap tandem mass spectrometry. Food Chem. 135:780–786.
  • Gray DE, Porter A, O’Neill T, Harris RK, Rottinghaus GE. 2004. A rapid cleanup method for the isolation and concentration of pyrrolizidine alkaloids in comfrey root. J AOAC Int. 87:1049–1057.
  • Griffin CT, Danaher M, Elliott CT, Kennedy DG, Furey A. 2013. Detection of pyrrolizidine alkaloids in commercial honey using liquid chromatography-ion trap mass spectrometry. Food Chem. 136:1577–1583.
  • Gritti F, Leonardis I, Shock D, Stevenson P, Shalliker A, Guiochon G. 2010. Performance of columns packed with the new shell particles, Kinetex-C18. J Chromatogr A. 1217:1589–1603.
  • Hoogenboom LAP, Mulder PPJ, Zeilmaker MJ, van den Top HJ, Remmelink GJ, Brandon EFA, Klijnstra M, Meijer GAL, 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.
  • Huxtable RJ. 1980. Herbal teas and toxins: novel aspects of pyrrolizidine poisoning in the United States. Perspect Biol Med. 24:1–14.
  • [ICH] International Conference on Harmonisation. 2005. Validation of analytical procedures: text and methodology Q2 (R1). ICH harmonized tripartite guideline [Internet]; [cited 2011 Dec 13]. Available from: http://www.ich.org/LOB/media/MEDIA417.pdf
  • [IPCS] International Programme on Chemical Safety. 1988. Pyrrolizidine alkaloids. Environmental Health Criteria 80. Geneva: WHO [Internet]; [cited 2011 Dec 13]. Available from: http://www.inchem.org/documents/ehc/ehc/ehc080.htm
  • Jiang Z, Liu F, Goh JJ, Yu L, Li SF, Ong ES, Ong CN. 2009. Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry. Talanta. 79:539–546.
  • Kakar F, Akbarian Z, Leslie T, Mustafa ML, Watson J, van Egmond HP, Omar MF, Mofleh J. 2011. An outbreak of hepatic veno-occlusive disease in western Afghanistan associated with exposure to wheat flour contaminated with pyrrolizidine alkaloids. J Toxicol. 139:728–735.
  • Kempf M, Wittig M, Schönfeld K, Cramer L, Schreier P, Beuerle T. 2011a. Pyrrolizidine alkaloids in food: downstream contamination in the food chain caused by honey and pollen. Food Addit Contam: Part A. 28:325–331.
  • Khokhar S, Magnusdottir SG. 2002. Total phenol, catechin, and caffeine contents of teas commonly consumed in the United Kingdom. J Agric Food Chem. 50:565–570.
  • Kinsella B, Byrne P, Cantwell H, McCormack M, Furey A, Danaher M. 2011. Determination of the new anthelmintic monepantel and its sulfone metabolite in milk and muscle using a UHPLC–MS/MS and QuEChERS method. J Chromatogr B. 879:3707–3713.
  • Kumana CR, Ng M, Lin HJ, Ko W, Wu PC, Todd D. 1983. Hepatic veno-occlusive disease due to toxic alkaloid in herbal tea. Lancet. 322:1360–1361.
  • Lebada R, Schreier A, Scherz S, Resch C, Krenn L, Kopp B. 2000. Quantitative analysis of the pyrrolizidine alkaloids senkirkine and senecionine in Tussilago farfara L. by capillary electrophoresis. Phytochem Anal. 11:366–369.
  • Lehane M, Fidalgo Sáez MJ, Magdalena AB, Ruppén Cañás I, Díaz Sierra M, Hamilton B, Furey A, James KJ. 2004. Optimised liquid chromatography – multiple tandem mass spectrometry method for the determination of azaspiracids, including hydroxyl analogues in shellfish. J Chromatogr A. 1024:62–70.
  • Lewis CJ. 2001. FDA advises dietary supplement manufacturers to remove Comfrey products from the market. Silver Spring (MD): FDA [Internet]; [cited 2011 Dec 13]. Available from: http://www.fda.gov/Food/RecallsOutbreaksEmergencies/SafetyAlertsAdvisories/ucm111219.htm
  • Li SL, Lin G, Fu PP, Chan CL, Li M, Jiang ZH, Zhao ZZ. 2008. Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang). Rapid Commun Mass Spectrom. 22:591–602.
  • Liu F, Wan SY, Jiang Z, Li SF, Ong ES, Osorio JC. 2009. Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry. Talanta. 80:916–923.
  • Mattocks AR. 1986. Chemistry and toxicology of pyrrolizidine alkaloids. London: Academic Press.
  • Mattocks AR, Cabral JR. 1982. Carcinogenicity of some pyrrolic pyrrolizidine alkaloid metabolites and analogues. Cancer Lett. 17:61–66.
  • McGaw LJ, Steenkamp V, Eloff JN. 2007. Evaluation of Athrixia bush tea for cytotoxicity, antioxidant activity, caffeine content and presence of pyrrolizidine alkaloids. J Ethnopharmacol. 110:16–22.
  • Mehta NJ, Karmody AM, McKneally MF. 1986. Mediastinal veno-occlusive disease associated with herbal tea ingestion. N Y State J Med. 86:604–605.
  • Molyneux RJ, Gardner DL, Colegate SM, Edgar JA. 2011. Pyrrolizidine alkaloid toxicity in livestock: a paradigm for human poisoning?. Food Addit Contam: Part A. 28:293–307.
  • Mroczek T, Widelski J, Glowniak K. 2006. Optimization of extraction of pyrrolizidine alkaloids from plant material. Chem Anal. 51:567–580.
  • Oberlies NH, Kim NC, Brine DR, Collins BJ, Handy RW, Sparacino CM, Wani MC, Wall ME. 2004. Analysis of herbal teas made from the leaves of comfrey (Symphytum officinale): reduction of N-oxides results in order of magnitude increases in the measurable concentration of pyrrolizidine alkaloids. Publ Health Nutr. 7:919–924.
  • Pak E, Esrason KT, Wu VH. 2004. Hepatotoxicity of herbal remedies: an emerging dilemma. Prog Transplant. 14:91–96.
  • Pittler MH, Ernst E. 2003. Systematic review: hepatotoxic events associated with herbal medicinal products. Aliment Pharmacol Ther. 18:451–471.
  • Prakash AS, Pereira TN, Reilly PE, Seawright AA. 1999. Pyrrolizidine alkaloids in human diet. Mutat Res/Gen Tox En. 443:53–67.
  • Qi X, Wu B, Cheng Y, Qu H. 2009. Simultaneous characterization of pyrrolizidine alkaloids and N-oxides in Gynura segetum by liquid chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom. 23:291–302.
  • Rasenack R, Müller C, Kleinschmidt M, Rasenack J, Wiedenfeld H. 2003. Veno-occlusive disease in a fetus caused by pyrrolizidine alkaloids of food origin. Fetal Diagn Ther. 18:223–225.
  • Ridker PM, Ohkuma S, McDermott WV, Trey C, Huxtable RJ. 1985. Hepatic venocclusive disease associated with the consumption of pyrrolizidine-containing dietary supplements. Gastroenterology. 88:1050–1054.
  • Roeder E. 2000. Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie. 55:711–726.
  • Roulet M, Laurini R, Rivier L, Calame A. 1988. Hepatic veno-occlusive disease in newborn infant of a woman drinking herbal tea. J Pediatr. 112:433–436.
  • Ruan J, Li N, Xia Q, Fu PP, Peng S, Ye Y, Lin G. 2012. Characteristic ion clusters as determinants for the identification of pyrrolizidine alkaloid N-oxides in pyrrolizidine alkaloid-containing natural products using HPLC-MS analysis. J Mass Spectrom. 47:331–337.
  • Rubert J, Soler C, Mañes J. 2012. Application of an HPLC–MS/MS method for mycotoxin analysis in commercial baby foods. Food Chem. 133:176–183.
  • Smith LW, Culvenor CCJ. 1981. Plant sources of hepatotoxic pyrrolizidine alkaloids. J Nat Prod. 44:129–152.
  • Soleimany F, Jinap S, Abas F. 2012. Determination of mycotoxins in cereals by liquid chromatography tandem mass spectrometry. Food Chem. 130:1055–1060.
  • Soler C, Hamilton B, Furey A, James KJ, Mañes J, Picó Y. 2006. Optimization of LC–MS/MS using triple quadrupole mass analyzer for the simultaneous analysis of carbosulfan and its main metabolites in oranges. Anal Chim Acta. 571:1–11.
  • Stegelmeier BL, Edgar JA, Colegate SM, Gardner DR, Schoch TK, Coulombe RA, Molyneux RJ. 1999. Pyrrolizidine alkaloid plants, metabolism and toxicity. J Nat Toxins. 8:95–116.
  • Stewart MJ, Steenkamp V. 2001. Pyrrolizidine poisoning: a neglected area in human toxicology. Ther Drug Monit. 23:698–708.
  • Stickel F, Patsenker E, Schuppan D. 2005. Herbal hepatotoxicity. J Hepatol. 43:901–910.
  • Stickel F, Seitz HK. 2000. The efficacy and safety of comfrey. Publ Health Nutr. 3:501–508.
  • Stuart KL, Bras G. 1955. Clinical observations on veno-occlusive disease of the liver in Jamaican adults. Br Med J. 2:348–352.
  • Tang J, Cheng M, Hattori M. 2012. Pyrrolizidine alkaloid profile in a traditional Chinese herbal medicine Chuan Zi Wan (Ligulariae Radix et Rhizoma) by liquid chromatography/electrospray ionization ion trap mass spectrometry. Anal Methods. 4:2797–2808.
  • Tittlemier SA, Lau BP, Ménard C, Corrigan C, Sparling M, Gaertner D, Pepper K, Feeley M. 2009. Melamine in infant formula sold in Canada: occurrence and risk assessment. J Agric Food Chem. 57:5340–5344.
  • Walpole SC, Prieto-Merino D, Edwards P, Cleland J, Stevens G, Roberts I. 2012. The weight of nations: an estimation of adult human biomass. BMC Publ Health. 12:439.
  • Wang D, Huang l, Chen S. 2013. Senecio scandens Buch.-Ham.: a review on its ethnopharmacology, phytochemistry, pharmacology, and toxicity. J Ethnopharmacol. 149:1–23.
  • Whelan M, Bloemhoff Y, Furey A, Sayers R, Danaher M. 2011. Investigation of the persistence of nitroxynil residues in milk from lactating dairy cows by ultra performance liquid chromatography tandem mass spectrometry. J Agric Food Chem. 59:7793–7797.
  • Wiedenfeld H. 2011. Plants containing pyrrolizidine alkaloids: toxicity and problems. Food Addit Contam: Part A. 28:282–292.
  • Windono T, Jenie UA, Kardono LBS. 2012. Isolation and elucidation of pyrrolizidine alkaloids from tuber of Gynura pseudo-china (L.) DC. J App Pharma Sci. 2:5–9.
  • Wuilloud JC, Gratze SR, Gamble BM, Wolnik KA. 2004. Simultaneous analysis of hepatotoxic pyrrolizidine alkaloids and N-oxides in comfrey root by LC-ion trap mass spectrometry. Analyst. 129:150–156.
  • Zhang F, Wang CH, Wang W, Chen LX, Ma HY, Zhang CF, Zhang M, Bligh SW, Wang ZT. 2008. Quantitative analysis by HPLC-MS2 of the pyrrolizidine alkaloid adonifoline in Senecio scandens. Phytochem Anal. 19:25–31.
  • Zhou J, Ouedraogo M, Qu F, Duez P. 2013. Potential genotoxicity of traditional Chinese medicinal plants and phytochemicals: an overview. Phytother Res. 27:1745–1755.
  • Zhou Y, Li N, Choi FF, Qiao CF, Song JZ, Li SL, Liu X, Cai ZW, Fu PP, Lin G, Xu HX. 2010. A new approach for simultaneous screening and quantification of toxic pyrrolizidine alkaloids in some potential pyrrolizidine alkaloid-containing plants by using ultra performance liquid chromatography-tandem quadrupole mass spectrometry. Anal Chim Acta. 681:33–40.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.