Analysis of selected phytotoxins and mycotoxins in environmental samples

Springer Science and Business Media LLC - Tập 395 - Trang 1261-1289 - 2009
Corinne C. Hoerger1, Judith Schenzel1, Bjarne W. Strobel2, Thomas D. Bucheli1
1Agroscope Reckenholz Tänikon Research Station ART, Zürich, Switzerland
2Department of Basic Sciences and Environment, University of Copenhagen, Frederiksberg C, Denmark

Tóm tắt

Natural toxins such as phytotoxins and mycotoxins have been studied in food and feed for decades, but little attention has yet been paid to their occurrence in the environment. Because of increasing awareness of the presence and potential relevance of micropollutants in the environment, phytotoxins and mycotoxins should be considered and investigated as part of the chemical cocktail in natural samples. Here, we compile chemical analytical methods to determine important phytotoxins (i.e. phenolic acids, quinones, benzoxazinones, terpenoids, glycoalkaloids, glucosinolates, isothiocyanates, phytosterols, flavonoids, coumestans, lignans, and chalcones) and mycotoxins (i.e. resorcyclic acid lactones, trichothecenes, fumonisins, and aflatoxins) in environmentally relevant matrices such as surface water, waste water-treatment plant influent and effluent, soil, sediment, manure, and sewage sludge. The main problems encountered in many of the reviewed methods were the frequent unavailability of suitable internal standards (especially isotope-labelled analogues) and often absent or fragmentary method optimization and validation.

Tài liệu tham khảo

van Egmond HP (2004) Anal Bioanal Chem 378:1152–1160 Krska R, Schubert-Ullrich P, Molinelli A, Sulyok M, Macdonald S, Crews C (2008) Food Addit Contam 25:152–163 Turner NW, Subrahmanyam S, Piletsky SA (2009) Anal Chim Acta 632:168–180 Zollner P, Mayer-Helm B (2006) J Chromatogr A 1136:123–169 Akhtar MH, Abdel-Aal ESM (2006) Curr Pharm Anal 2:183–193 Vacek J, Klejdus B, Lojkova L, Kuban V (2008) J Sep Sci 31:2054–2067 Hannah DJ, Till DG, Truman P (1998) Phycotoxins – A review of chemical and biological methods of analysis. In: Miraglia M, van Egmond HP, Brera C, Gilbert J (eds) Mycotoxins and Phycotoxins – developments in chemistry, toxicology and food safety. Alaken, Inc. Fort Collins, CO Fremy JM, Puech L, Krys S, Dragacci S (1999) J Appl Phycol 11:377–384 Perez S, Aga DS (2005) Trends Anal Chem 24:658–670 Hungerford JM (2006) J AOAC Int 89:248–269 Bernet D, Liedtke A, Bittner D, Eggen RIL, Kipfer S, Kung C, Largiader CR, Suter MJF, Wahli T, Segner H (2008) Chimia 62:383–388 Fate and Toxicity of allelochemicals (natural plant toxins) in relation to environment and consumer (FATEALLCHEM). http://www.fateallchem.dk/. Accessed 17 Aug 2009 Fomsgaard IS (2006) J Agric Food Chem 54:987–990 Rasmussen LH, Kroghsbo S, Frisvad JC, Hansen HCB (2003) Chemosphere 51:117–127 Jensen PH, Strobel BW, Hansen HCB, Jacobsen OS (2009) J Agric Food Chem 57:2862–2867 Hartmann N, Erbs M, Forrer HR, Vogelgsang S, Wettstein FE, Schwarzenbach RP, Bucheli TD (2008) Environ Sci Technol 42:5455–5460 Martens DA (2002) Soil Sci Soc Am J 66:1240–1248 Dalton BR, Weed SB, Blum U (1987) Soil Sci Soc Am J 51:1515–1521 De Scisciolo B, Leopold DJ, Walton DC (1990) J Chem Ecol 16:1111–1130 Wright DA, Dawson R, Cutler SJ, Cutler HG, Orano-Dawson CE, Graneli E (2007) Water Res 41:1294–1302 Girzu M, Fraisse D, Carnat AP, Carnat A, Lamaison JL (1998) J Chromatogr A 805:315–318 Jose S, Gillespie AR (1998) Plant Soil 203:191–197 von Kiparski GR, Lee LS, Gillespie AR (2007) J Environ Qual 36:709–717 Dayan FE, Kagan IA, Rimando AM (2003) J Biol Chem 278:28607–28611 Czarnota MA, Rimando AM, Weston LA (2003) J Chem Ecol 29:2073–2083 Erickson J, Schott D, Reverri T, Muhsin W, Ruttledge T (2001) J Agric Food Chem 49:5537–5542 Trezzi MM, Vidal RA, Dick DP, Peralba MCR, Kruse ND (2006) J Environ Sci Heal B 41:345–356 Macias FA, Oliveros-Bastidas A, Marin D, Castellano D, Simonet AM, Molinillo JMG (2004) J Agric Food Chem 52:6402–6413 Macias FA, Oliveros-Bastidas A, Marin D, Castellano D, Simonet AM, Molinillo JMG (2005) J Agric Food Chem 53:554–561 Gents MB, Nielsen ST, Mortensen AG, Christophersen C, Fomsgaard IS (2005) Chemosphere 61:74–84 Krogh SS, Mensz SJM, Nielsen ST, Mortensen AG, Christophersen C, Fomsgaard IS (2006) J Agric Food Chem 54:1064–1074 Understrup AG, Ravnskov S, Hansen HCB, Fomsgaard IS (2005) J Chem Ecol 31:1205–1222 Etzerodt T, Mortensen AG, Fomsgaard IS (2008) J Environ Sci Heal B 43:1–7 Etzerodt T, Nielsen ST, Mortensen AG, Christophersen C, Fomsgaard IS (2006) J Agric Food Chem 54:1075–1085 Fomsgaard IS, Mortensen AG, Idinger J, Coja T, Blumel S (2006) J Agric Food Chem 54:1086–1092 Eljarrat E, Guillamon M, Seuma J, Mogensen BB, Fomsgaard IS, Olivero-Bastidas A, Macias FA, Stochmal A, Oleszek W, Shakaliene O, Barcelo D (2004) J Chromatogr A 1047:69–76 Villagrasa M, Guillamon M, Navarro A, Eljarrat E, Barcelo D (2008) J Chromatogr A 1179:190–197 Gershenzon J, Dudareva N (2007) Nat Chem Biol 3:408–414 Kanerva S, Kitunen V, Loponen J, Smolander A (2008) Biol Fert Soils 44:547–556 Isidorov VA, Vinogorova VT, Rafalowski K (2003) Atmos Environ 37:4645–4650 Strobel BW, Jensen PH, Rasmussen LH, Hansen HCB (2005) Scan J Forest Res 20:7–11 Smolander A, Ketola RA, Kotiaho T, Kanerva S, Suominen K, Kitunen V (2006) Soil Biol Biochem 38:3436–3442 Asensio D, Owen SM, Llusia J, Penuelas J (2008) Soil Biol Biochem 40:2937–2947 Klausen C, Nicolaisen MH, Strobel BW, Warnecke F, Nielsen JL, Jorgensen NOG (2005) Fems Microbiol Ecol 52:265–278 Jessing K, Bowers T, Strobel BW, Svensmark B, Hansen HC (2009) Intern J Environ Anal Chem 89:1–10 Lapkin AA, Walker A, Sullivan N, Khambay B, Mlambo B, Chemat S (2009) J Pharm Biomed 49:908–915 Tzeng TC, Lin YL, Jong TT, Chang CMJ (2007) Sep Purif Technol 56:18–24 Ferreira JFS, Gonzalez JM (2009) Phytochem Anal 20:91–97 Hanpithakpong W, Kamanikom B, Dondorp AM, Singhasivanon P, White NJ, Day NPJ, Lindegardh N (2008) J Chromatogr B 876:61–68 Hodel EM, Zanolari B, Mercier T, Biollaz J, Keiser J, Olliaro P, Genton B, Decosterd LA (2009) J Chromatogr B 877:867–886 Agnew MP, Lauren DR (1991) J Chromatogr 538:462–468 Ovesen RG, Rasmussen LH, Hansen HCB (2008) Environ Toxicol Chem 27:252–259 Jensen PH, Jacobsen OS, Hansen HCB, Juhler RK (2008) J Agric Food Chem 56:9848–9854 Jensen PH, Jacobsen OS, Henriksen T, Strobel BW, Hansen HCB (2009) Bull Environ Contam Toxicol 82:668–672 Friedman M (2006) J Agric Food Chem 54:8655–8681 Friedman M, McDonald GM (1997) Crit Rev Plant Sci 16:55–132 Jensen PH, Harder BJ, Strobel BW, Svensmark B, Hansen HCB (2007) Intern J Environ Anal Chem 87:813–824 Jensen PH, Pedersen RB, Svensmark B, Strobel BW, Jacobsen OS, Hansen HCB (2009) Chemosphere 76:1150–1155 Jensen PH, Juhler RK, Nielsen NJ, Hansen TH, Strobel BW, Jacobsen OS, Nielsen J, Hansen HCB (2008) J Chromatogr A 1182:65–71 Kirkegaard JA, Sarwar M (1998) Plant Soil 201:71–89 Gardiner JB, Morra MJ, Eberlein CV, Brown PD, Borek V (1999) J Agric Food Chem 47:3837–3842 Brown PD, Morra MJ, Borek V (1994) J Agric Food Chem 42:2029–2034 Gimsing AL, Kirkegaard JA, Hansen HCB (2005) J Agric Food Chem 53:9663–9667 Omirou M, Papastylianou I, Iori R, Papastephanou C, Papadopoulou KK, Ehaliotis C, Karpouzas DG (2009) Phytochem Analysis 20:214–220 Gimsing AL, Sorensen JC, Strobel BW, Hansen HCB (2007) Appl Clay Sci 35:212–217 Gimsing AL, Sorensen JC, Tovgaard L, Jorgensen AMF, Hansen HCB (2006) Environ Toxicol Chem 25:2038–2044 Strobel BW, Hansen HCB, Borggaard OK, Andersen MK, Raulund-Rasmussen K (2001) Biogeochemistry 56:1–26 Westergaard B, Hansen HCB, Borggaard OK (1998) Analyst 123:721–724 Botting CH, Davidson NE, Griffiths DW, Bennett RN, Botting NP (2002) J Agric Food Chem 50:983–988 Fabre N, Poinsot V, Debrauwer L, Vigor C, Tulliez J, Fouraste I, Moulis C (2007) Phytochem Anal 18:306–319 Tian QG, Rosselot RA, Schwartz SJ (2005) Anal Biochem 343:93–99 Laegdsmand M, Gimsing AL, Strobel BW, Sorensen JC, Jacobsen OH, Christian H, Hansen B (2007) Plant Soil 291:81–92 Gimsing AL, Poulsen JL, Pedersen HL, Hansen HCB (2007) Environ Sci Technol 41:4271–4276 Breinholt V, Larsen JC (1998) Chem Res Toxicol 11:622–629 Coldham NG, Dave M, Sivapathasundaram S, McDonnell DP, Connor C, Sauer MJ (1997) Environ Health Perspect 105:734–742 Rosenberg Zand RS, Jenkins DJA, Diamandis EP (2000) Breast Cancer Res Tr 62:35–49 Sivesind E, Seguin P (2005) J Agric Food Chem 53:6397–6402 Cavaliere C, Cucci F, Foglia P, Guarino C, Samperi R, Lagana A (2007) Rapid Commun Mass Spectrom 21:2177–2187 Sjostrom E (1993) Wood Chemistry Fundamentals and Applications. Academic Press, New York Habermehl G, Hammann PE (1992) Naturstoffchemie: Eine Einführung. Springer, Berlin Heidelberg New York Bais HP, Walker TS, Stermitz FR, Hufbauer RA, Vivanco JM (2002) Plant Physiol 128:1173–1179 Mazur W (1998) Bailliere Clin Endoc 12:729–742 Price KR, Fenwick GR (1985) Food Addit Contam 2:73–106 Reinli K, Block G (1996) Nutr Cancer 26:123–148 Lundh T (1995) P Soc Exp Biol Med 208:33–39 Hassett JP, Lee GF (1977) Water Res 11:983–989 Ikonomou MG, Cai SS, Fernandez MP, Blair JD, Fischer M (2008) Environ Toxicol Chem 27:243–251 Ternes TA, Eggert T, Meisenheimer M (2001) Pflanzliche hormonell wirksame Stoffe in der aquatischen Umwelt und deren Verhalten bei der Trinkwasseraufbereitung. Abschlussbericht ESWE-Institut für Wasserforschung und Wassertechnologie GmbH, Wiesbaden Germany Pawlowski S, Ternes TA, Bonerz M, Rastall AC, Erdinger L, Braunbeck T (2004) Toxicol In Vitro 18:129–138 Zaugg SD, Smith SG, Schroeder MP (2006) Determination of wastewater compounds in whole water by continuous liquid–liquid extraction and capillary-column gas chromatography/mass spectrometry. US Geological Survey Techniques and Methods, Book 5, Chap. B4 Kolpin DW, Skopec M, Meyer MT, Furlong ET, Zaugg SD (2004) Sci Total Environ 328:119–130 Focazio MJ, Kolpin DW, Barnes KK, Furlong ET, Meyer MT, Zaugg SD, Barber LB, Thurman ME (2008) Sci Total Environ 402:201–216 Baig S, Hansmann G, Paolini B (2008) Water Sci Technol 58:451–458 Mudge SM, Hooper L, Icely JD (1998) Environ Technol 19:1055–1059 Orrego R, Guchardi J, Hernandez V, Krause R, Roti L, Armour J, Ganeshakumar M, Holdway D (2009) Environ Toxicol Chem 28:181–188 Puglisi E, Nicelli M, Capri E, Trevisan M, Del Re AAM, Trevisan M (2003) J Environ Qual 32:466–471 Quemeneur M, Marty Y (1994) Water Res 28:1217–1226 Simpson IA, van Bergen PF, Perret V, Elhmmali MM, Roberts DJ, Evershed RP (1999) Holocene 9:223–229 Farre M, Kuster M, Brix R, Rubio F, de Alda MJL, Barcelo D (2007) J Chromatogr A 1160:166–175 Lee J, Lee BC, Ra JS, Cho J, Kim IS, Chang NI, Kim HK, Kim SD (2008) Chemosphere 71:1582–1592 Spengler P (2001) Identifizierung und Quantifizierung von Verbindungen mit östrogener Wirkung im Abwasser. Thesis at the Institute for Civil Ingenieering, Water Quality and Waste Economy, Stuttgart Burnison BK, Hartmann A, Lister A, Servos MR, Ternes T, Van Der Kraak G (2003) Environ Toxicol Chem 22:2243–2250 Ferrer I, Barber LB, Thurman EM (2009) J Chromatogr A 1216:6024–6032 Erbs M, Hoerger CC, Hartmann N, Bucheli TD (2007) J Agric Food Chem 55:8839–8345 Farre M, Gros M, Hernandez B, Petrovic M, Hancock P, Barcelo D (2008) Rapid Commun Mass Spectrom 22:41–51 Ribeiro C, Pardal MA, Martinho F, Margalho R, Tiritan ME, Rocha E, Rocha MJ (2009) Environ Monit Assess 149:183–193 Ribeiro C, Tiritan ME, Rocha E, Rocha MJ (2009) Arch Environ Contam Toxicol 56:1–11 Hoerger CC, Wettstein FE, Hungerbühler K, Bucheli TD (2009) Environ Sci Technol 43:6151–6157 Alford ER, Perry LG, Qin B, Vivanco JM, Paschke MW (2007) Soil Biol Biochem 39:1812–1815 Hughes RJ, Croley TR, Metcalfe CD, March RE (2001) Int J Mass Spectrom 210:371–385 Inderjit A, Asakawa C, Dakshini KMM (1999) Can J Bot 77:1419–1424 Perry LG, Thelen GC, Ridenour WM, Callaway RM, Paschke MW, Vivanco JM (2007) J Chem Ecol 33:2337–2344 Perry LG, Thelen GC, Ridenour WM, Weir TL, Callaway RM, Paschke MW, Vivanco JM (2005) J Ecol 93:1126–1135 Tharayil N, Bhowmik PC, Xing BS (2008) J Agric Food Chem 56:3706–3713 Shaw LJ, Hooker JE (2008) Soil Biol Biochem 40:528–536 Ozan A, Safir GR, Nair MG (1997) J Chem Ecol 23:247–258 Kang J, Price WE, Hick LA (2006) Rapid Commun Mass Spectrom 20:2411–2418 Lundgren MS, Novak PJ (2009) Environ Toxicol Chem in press Bennett JW, Kale S, Yu J (2007) Alfatoxins: Background, Toxicology, and Molecular Biology. In: Simjee S (ed) Infectious Disease: Foodborne Diseases. Humana Press, Totowa, NJ Schlatter J (2004) Toxicol Lett 153:83–89 Zinedine A, Soriano JM, Molto JC, Manes J (2007) Food Chem Toxicol 45:1–18 Cigic IK, Prosen H (2009) Int J Mol Sci 10:62–115 Rahmani A, Jinap S, Soleimany F (2009) Compr Rev Food Sci F 8:202–251 Reiter E, Zentek J, Razzazi E (2009) Mol Nutr Food Res 53:508–524 Songsermsakul P, Razzazi-Fazeli E (2008) J Liq Chromatogr Relat Technol 31:1641–1686 Abbas HK, Zablotowicz RM, Weaver MA, Horn BW, Xie W, Shier WT (2004) Can J Microbiol 50:193–199 Benedetti R, Nazzi F, Locci R, Firrao G (2006) Biodegradation 17:31–38 Harrach B, Bata A, Bajmocy E, Benko M (1983) Appl Environ Microb 45:1419–1422 Fernandez MP, Ikonomou MG, Buchanan I (2007) Sci Total Environ 373:250–269 Ternes TA, Stumpf M, Mueller J, Haberer K, Wilken RD, Servos M (1999) Sci Total Environ 225:81–90 Hartmann N, Erbs M, Wettstein FE, Schwarzenbach RP, Bucheli TD (2007) J Chromatogr A 1138:132–140 Lagana A, Fago G, Marino A, Santarelli D (2001) Rapid Commun Mass Spectrom 15:304–310 Russell R, Paterson M (2007) Mycol Prog 6:109–113 Bucheli TD, Wettstein FE, Hartmann N, Erbs M, Vogelgsang S, Forrer HR, Schwarzenbach RP (2008) J Agric Food Chem 56:1029–1034 Gromadzka K, Waskiewicz A, Golinski P, Swietlik J (2009) Water Res 43:1051–1059 Mortensen GK, Strobel BW, Hansen HCB (2003) Anal Bioanal Chem 376:98–101 Hartmann N, Erbs M, Wettstein FE, Hoerger CC, Schwarzenbach RP, Bucheli TD (2008) J Agric Food Chem 56:2926–2932 Lagana A, Bacaloni A, De Leva I, Faberi A, Fago G, Marino A (2004) Anal Chim Acta 501:79–88 Rychlik M, Asam S (2008) Anal Bioanal Chem 390:617–628 Jodlbauer J, Zollner P, Lindner W (2000) Chromatographia 51:681–687 van Bennekom EO, Brouwer L, Laurant EHM, Hooijerink H, Nielen MWF (2002) Anal Chim Acta 473:151–160 Garon D, Richard E, Sage L, Bouchart V, Pottier D, Lebailly P (2006) J Agric Food Chem 54:3479–3484 Mortensen GK, Strobel BW, Hansen HCB (2006) Chemosphere 62:1673–1680 Songsermsakul P, Sontag G, Cichna-Markl M, Zentek J, Razzazi-Fazeli E (2006) J Chromatogr B 843:252–261 Richard E, Heutte N, Bouchart V, Garon D (2009) Anim Feed Sci Tech 148:309–320 Lee PK, Kee SYK, Ng W, Gopalakrishnakone P (1999) J High Resol Chromatogr 22:424–426 Russo MV, Veschetti E, Cinelli G, Avino P (2007) Chromatographia 66:237–242 Madden UA, Stahr HM (1993) Int Biodeter Biodegr 31:265–275 Williams LD, Bacon CW, Meredith FI, Franzluebbers AJ, Wyatt RD, Smith MA, Riley RT (2003) J Agric Food Chem 51:685–690 Monti SM, Fogliano V, Logrieco A, Ferracane R, Ritieni A (2000) J Agric Food Chem 48:3317–3320 Paterson RRM, Kelley J, Gallagher M (1997) Lett Appl Microbiol 25:435–436 Starr JM, Selim MI (2008) J Chromatogr A 1209:37–43 Reichenberg F, Mayer P (2006) Environ Toxicol Chem 25:1239–1245 Weidenhamer JD (2005) J Chem Ecol 31:221–236 Weidenhamer JD (2007) Allelopathy J 19:135–142 Blum U, Wentworth TR, Klein K, Worsham AD, King LD, Gerig TM, Lyu SW (1991) J Chem Ecol 17:1045–1068 Kelley WT, Coffey DL, Mueller TC (1994) J AOAC Intern 77:805–809 Gallet C, Nilsson MC, Zackrisson O (1999) Plant Soil 210:1–9 Sene M, Gallet C, Dore T (2001) J Chem Ecol 27:81–92 Suominen K, Kitunen V, Smolander A (2003) Eur J Soil Sci 54:287–293 Seal AN, Pratley JE, Haig T, An M (2004) J Chem Ecol 30:1647–1662 Weidenhamer JD, Romeo JT (2004) J Chem Ecol 30:1067–1082 Kong CH, Li HB, Hu F, Xu XH, Wang P (2006) Plant Soil 288:47–56 Muscolo A, Sidari M (2006) Plant Soil 284:305–318 Bonadies F, Borzacchiello G, Dezzi S, Nicoletti R, Roperto S (2004) Rapid Commun Mass Spectrom 18:825–828 Jaffe R, Rushdi AI, Medeiros PM, Simoneit BRT (2006) Chemosphere 64:1870–1884 Lahdelma I, Oikari A (2006) J Paleolimnol 35:323–334 Bligh EG, Dyer WJ (1959) Can J Biochem Phys 37:911–917 Pratt C, Warnken J, Leeming R, Arthur JM, Grice DI (2007) Environ Sci Technol 41:792–802 Rogge WF, Medeiros PM, Simoneit BRT (2006) Atmos Environ 40:27–49 Stumpf M, Ternes TA, Haberer K, Baumann W (1996) Vom Wasser 87:251–261 Cook DL, LaFleur L, Parrish A, Jones J, Hoy D (1997) Water Sci Technol 35:297–303 Bätscher R, Studer C, Fent K (1999) Umweltgefährdende Stoffe: Stoffe mit endokriner Wirkung in der Umwelt. BUWAL, p 258 Seguel CG, Mudge SM, Salgado C, Toledo M (2001) Water Res 35:4166–4174 Spengler P, Korner W, Metzger JW (2001) Environ Toxicol Chem 20:2133–2141 Mahmood-Khan Z, Hall ER (2003) J Environ Eng Sci 2:17–26 Noblet JA, Young DL, Zeng EY, Ensari S (2004) Environ Sci Technol 38:6002–6008 Peng XZ, Zhang G, Mai BX, Hu JF, Li KC, Wang ZD (2005) Mar Pollut Bull 50:856–865 Szucs S, Sarvary A, Cain T, Adany R (2006) J Chromatogr Sci 44:70–76 Tyagi P, Edwards DR, Coyne MS (2007) Chemosphere 69:1617–1624 Spring AJ, Bagley DM, Andrews RC, Lemanik S, Yang P (2007) J Environ Eng Sci 6:131–137 Zgheib S, Gromaire MC, Lorgeoux C, Saad M, Chebbo G (2008) Water Sci Technol 57:1705–1712 Metcalfe CD, Nanni ME, Scully NM (1995) Chemosphere 30:1085–1095 Johnston KM, Stern DJ, Waiss AC (1968) J Chromatogr 33:539–541 Kiparissis Y, Hughes R, Metcalfe C, Ternes T (2001) Environ Sci Technol 35:2423–2427 Kawanishi M, Takamura-Enya T, Ermawati R, Shimohara C, Sakamoto M, Matsukawa K, Matsuda T, Murahashi T, Matsui S, Wakabayashi K, Watanabe T, Tashiro Y, Yagi T (2004) Environ Sci Technol 38:6424–6429 Bacaloni A, Cavaliere C, Faberi A, Foglia P, Samperi R, Lagana A (2005) Anal Chim Acta 531:229–237 Beck IC, Bruhn R, Gandrass J, Ruck W (2005) J Chromatogr A 1090:98–106 Furuichi T, Kannan K, Suzuki K, Tanaka S, Giesy JP, Masunaga S (2006) Environ Sci Technol 40:7896–7902 Ribeiro C, Tiritan ME, Rocha E, Rocha MJ (2007) J Liq Chromatogr Relat Technol 30:2729–2746