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1 Rep.Nat l.foodres.inst No.72, Hiroyuki Nakagawa, Mayumi Ohnishi Kameyama, Yuki Sago, Hiroshi Yada, Masayo Kushiro, and Hitoshi Nagashima National Food Research Institute, Kannon dai, Tsukuba, Ibaraki Aflatoxins (AFs) are the most potent carcinogenic and toxic compounds among many kinds of substances in the nature, and benzo a pyrene (BaP) is known as a hardly degradable compound and also recognized as a carcinogen. Simultaneous detection of AFs (AFB, AFB, AFG, and AFG ) and BaP was performed by liquid chromatography /tandem mass spectrometry (LC/MS /MS) equipped with an atomospheric pressure photo ionization (APPI) probe. Mixtures of AFs and BaP were applied to multi functional columns suggested for the purification on an official method for AFs determination, and both of them were well eluted through an Autoprep MF A1000 column. In the aim of practical usage for food analysis, AFs and BaP were added to olive oil at the concentration of 4.0 g/kg and 40 g/kg, respectively, and analyzed with LC/ MS/MS. When AFs and BaP were purified from olive oil with a sosid phase extraction column Autoprep MF A1000, the mean recovery of BaP was low (12.8 %) in contrast to that of AFs ( %). The cause of low recovery of BaP was its low extraction efficiency from olive oil with the solvent of acetonitrile water (90: 10). If the purification process is improved to increase the extraction efficiency of BaP from olive oil, our method must be useful for the analysis of AFs and BaP contaminated in various foods. AF s Aspergillusflavus Aspergillusparasiticus Aspergillusnomius Aspergil lutamarii AFs AFs BAFB BAFB G AFG GAFG 4 1 AFB AFB 10ppb AFB Corresponding author, Hiroyuki Nakagawa
2 polycyclic aromatic hydrocarbon spah s 2 4 PAHs, a BaP 1 PAHs PAHs PAH BaP IARC FAO WHO EU 2.0ppb 10ppb BaP 2.0ppb WHO 0.7ppb BaP PAH PAHs BaP PAHs AFs BaP LC/MS/MS AFs AFs BaP PAHs AFs AFs PAHs atomospheric pressure photo ionization, APPI LC/MS/MS AF 4 BG Acrosorganics BG BaP AccuStandard 4AFB AFG 2030 LI BRORLM 20 1mg LC/MS 10ml 20ml Arrow 20ml AFs 20BaP 4 30
3 AFs 4 BaP AFs BaP 1 ppm 1 ml 500 l 200 l 100 l 10 ml AFs BaP ppb 50 ppb 1 ml 400 l 200 l 100 l 10 ml AFs BaP ppb 2 ppb 1 ml 500 l 10 ml AFs BaP ppb LC/MS/MS Agilent 1100 Agilent Technologies APPI 4000QTRAP LC/MS/ MS Applied Biosystems LC A 0.1 B 0.1 ZOR BAX Eclipse Plus C182.1mm 150mm 3.5 micron, Agilent Technologies 0.20 ml B B B B B AFBAFB AFGAFG BaP APPI HPLC 0.02 ml/ 625 V500 10psi30 psi 10psi MRM AFs BaP M H MS/MS HPLC AFs BaP AFs BaP AFs AF AF 3 AFs4 BaP AutoprepMF A1000 Multisep 226 AflaZonRomerLabs Multisep 228 AflaPat 1 AFs BaP 1ppm 1ml 10ml 1ml 90 Autoprep MF A1000 2ml 20ml 3.2ml 84 Multisep 226 AflaZon Multisep 228 AflaPat AFs BaP 100ppb AFs AFs AFs AFs Varian 1.0ml 7 0.5ml/1.0ml /7ml GL 1.0ml
4 m/z m/z AFB AFB AFG AFG BaP DP:Declusteringpotential V CE:Collisionenergy V DP CE Agilent Technologies LC/MS/MS AFs Papachristou BaP AFs BaP AFs4 BaP AFs 50ml 35mm 110mm 2.5g AFs4 0.1ppm BaP 1 ppm 100 l AFs4 4.0 g/kg BaP 40 g/kg ml KM ShakerV DX 300rpm 30 15ml 16.5mm 125mm3000 g 10 Varian 1.0 ml GL l Agilent LC/MS/MS 3 Agilent 3 2.5g AFs BaP 100 l 2 AFs BaP M H LC/MS/MS AFs4 BaP 1 AFs 4 BaP ppb AFBAFG ppb AFBAFG ppb BaP ppb S/N 3 S/N 10 AFB 0.2ppb 0.5ppb AFB 0.5 ppb 1.0 ppb AFG 0.2 ppb 0.5 ppb AFG 0.5 ppb 1.0 ppb BaP 1.0 ppb 2.0 ppb AFs BaP AFs BaP 100ppb 3 AutoprepMF A1000 Multisep 226 AflaZonMultisep 228
5 49 表2 多機能カラム Autoprep MF A1000 における AFs と BaP の流出パターン a 濃度 ppb フラクション番号 1 AFB AFB AFG1 AFG2 BaP a AFs と BaP を各 100ppb ずつ含む 90 アセトニトリルを負荷し 1 ml ずつ分取した 図2 LC/MS/MS による AFs と BaP の同時分析の MS/MS クロマトグラム AflaPat に負荷したところ AFs はいずれのカラム ラムのベッドボリュームが異なるので充. 剤の材質だ においてもフラクション 1 本目から ppb 負 けに依存するとは限らないが AFs と BaP の同時精 荷濃度の 相当 の流出が確認された 製には Autoprep MF A1000 を用いるのが適当である これに対して BaP は AutoprepMF A1000 ではフラク と判断した 表 2 に Autoprep MF A1000 における AFs ション 3 本目以降で ppb 負荷濃度の 88.2 および BaP の流出パターンを示す 104 相当 Multisep226 ではフラクション 6 本目 以降で ppb 負荷濃度の 相当 3 オリーブ油への添加回収試験 の流出が確認された 一方 Multisep228 ではフラク オリーブ油への添加回収試験は最も良好な流出パタ ション 7 本目まで BaP の溶出が確認されず 流出速 ーンを示した Autoprep MF A1000 を用いて精製を行っ 度も遅かったため AFs と BaP の同時精製には不適 た 抽出はアセトニトリル 水混合液 を用 当であると判断した データ省略 以上より 各カ いて行った 表 2 の結果より BaP はフラクション 4
6 AFB AFB AFG AFG BaP Spiked levelg/kg Mean Recovery %n Relative standard deviation RSD AFs BaP 4 4 MS/MS AFBAFBAFGAFG RSD BaP g 100 l AFs BaP AFs BaP LC/MS/MS AFs APPI LC/MS Takino PAHs APPI LC/MS/MS Moriwaki PAHs PAHs PAHs GC/MS GC MS/MS LC/MS/MS APPI LC/MS/MS PAHs LC/MS/MS GC/MS /MS OH COOH LC/MS/MS APPI LC/MS/MS AFs 4 BaP PAHs LC/MS/MS PAHs APPI LC/MS/MS Moriwaki BaP 1.0 ppb Moriwaki BaP M H M AFs BaP M H BaP M LC 0.1 M H AFs BaP Autoprep MF A1000 AFs BaP AFs AF Autoprep MF A BaP 12.8AFs AFs BaP 2 BaP BaP Autoprep MF A Autoprep MF A1000
7 AFs BaP AFs AFB 6 10ppb BaP EU 2.0ppb 2.0ppb LC/MS/MS AFs BaP 100ppb AFs BaP 100 ppb BaP 2.0ppb Papachristou AFs A OTA OTA BaP OTA BaP LC/MS/MS OTA Multisep 229 Ochra Romer Labs BaP APPI LC/MS/ MS OTA BaP OTA AF BaP AFs BaP APPI LC/ MS/MS AFs 4 AFB, AFB, AFG, AFG a BaP AFs BaP AF 3 Autoprep MF A1000 AFs BaP AFs BaP 4.0 g/kg 40 g/kg Autoprep MF A1000 AFs BaP BaP AFs 1) Dvorackova, I. (1990) Aflatoxins and Human Health. CRC Press, Boca Raton, FL. 2) Bhatnagar, D., Cleveland, T. E., Brown, R. L., Cary, J. W., Yu, J., and Chang, P. K., Preharvest aflatoxin contamination: elimination through biotechnology. In: Dhaliwal GS, Arora R, Randh
8 awa NS, Dhawan AR (eds) Ecological agriculture and sustainable development, vol. 1. Indian Eco logical Society. Ludhiana, India, pp (1997). 3) Cleveland, T. E. and Bhatnagar, D., Molecular strategies for reducing aflatoxin levels in crops before preharvest. In: Bhatnagar D, Cleveland TE (eds) Molecular approaches to improving food quality and safety. Van Nostrand Reinhold, New York, pp (1992). 4) Guillen, M., D., Sopelana, P., Partearroyo, M. A., Food as a source of polycyclic aromatic carcino gens. Rev. Environ. Health, 12, (1997). 5) 39, (1998). 6) Ilidas, K., N., Zotos, A., Taylor, A., KD., and Petridis, D., Effect of pre treatment and smoking process (cold and hot) on chemical, microbiological and sensory quality of mackerel (Scomber scombrus). J. Sci. Food Agric., 84, (2004). 7) Strelli, M., M., Stuffler, R., G., and Marcotrigiano, G., O., Polycyclic aromatic hydrocarbons, polych lorinated biphenyls, chlorinated pesticides (DDTs), hexacyclohexane, and hexachlorobenzene residues in smoked seafood. J. Food Prot., 66, (2003). 8) Anastasio, A., Mercogliano, R., Vollano, L., Pepe, T., and Cortesi, M. L., Levels of benzo [a] pyrene (BaP) in Mozzarella di Bufala Campana cheese smoked according to different procedures. J. Agric. Food Prot., 52, (2004). 9) Purcaro, G., Navas, J., A., Guardiola, F., Conte, L., S., and Moret, S., Polycylcic aromatic hydrdocarbons in frying oils and snacks. J. Food Prot., 69, (2006). 10) Kazerouni, N., Sinha, R., Hsu, C H., Greenberg, A., and Rothman, N., Analysis of 200 food items for benzo [a] pyrene and estimation of its intake an epidemiologic study. Food and Chem., Toxicol., 39, (2001). 11) Rhee, K. S. and Bratzler, L. J., Benzo [a] pyrene in smoked meat products. J. Food Sci., 35, (1970). 12) Howard, J. W. and Fazio, T., Review of polycyclic aromatic hydrocarbons in foods. Analytical meth ology and reported findings of polycyclic aromatic hydrocarbons in foods. J. Assoc. Off. Anal. Chem., 63, (1980). 13) Bjorseth, A., Handbook of polycyclic aromatic hydrocarbons. Mercel Dekker, New York (1983). 14) Papachristou, A. and Markaki, P., Determination of ochratoxin A in virgin olive oils of Greek origin by immunoaffinity column clean up and high performance liquid chromatography. Food Addit. Contam., 21, (2004). 15) Takino, M., Tanaka, T., Yamaguchi, K., and Nakahara, T., Atomospheric pressure photo ionization liquid chromatography/mass spectrometric determination of aflatoxins in food. Food Addit. Contam., 21, (2004). 16) Moriwaki, H., Ishitake, M., Yoshikawa, S., Miya koda, H., and Alary, J F., Determination of polycyclic aromatic hydrocarbons in sediment by liquid chromatography atomosphere pressure photoionization mass spectrometry. Anal. Sci. Feb., 20, (2004).
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