Absorption and metabolism of the food contaminant 3-chloro-1,2-propanediol (3-MCPD) and its fatty acid esters by human intestinal Caco-2 cells

Archives of Toxicology

Volumn 85, Issue 10, 2011, Pages 1201-1208

  Buhrke, Thorsten ^a   Weihaar, Rüdiger ^b   Lampen, Alfonso ^a  

^a FEDERAL INSTITUTE FOR RISK ASSESSMENT   (Germany)

^b CVUA Stuttgart   (Germany)

Author keywords

3 MCPD; 3 MCPD fatty acid ester; Caco 2; Food contaminant; Risk assessment

Indexed keywords

3 CHLORO 1,2 PROPANEDIOL 1 MONOESTER; 3 CHLORO 1,2 PROPANEDIOL 1 MONOLAUREATE; 3 CHLORO 1,2 PROPANEDIOL 1 MONOOLEATE; 3 CHLORO 1,2 PROPANEDIOL 1,2 DIESTER; 3 CHLORO 1,2 PROPANEDIOL FATTY ACID ESTER; ALPHA CHLOROHYDRIN; TOXIC SUBSTANCE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CELL DIFFERENTIATION; CELL METABOLISM; CELL STRAIN CACO 2; CELL TRANSPORT; CONCENTRATION RESPONSE; CONTROLLED STUDY; DETOXIFICATION; DIFFUSION; FOOD CONTAMINATION; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; INTESTINE CELL; INTESTINE MUCOSA PERMEABILITY; MONOLAYER CULTURE; PRIORITY JOURNAL; RISK ASSESSMENT; TOXICOKINETICS; TRANSPORT KINETICS; XENOBIOTIC METABOLISM;

CACO-2 CELLS; ESTERS; FOOD CONTAMINATION; GLYCEROL; HUMANS; HYDROLYSIS; INTESTINAL ABSORPTION; INTESTINES; LIPASE; METABOLIC DETOXICATION, DRUG;

RODENTIA;

EID: 80755175927     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-011-0657-6     Document Type: Article

References (30)

1. J Aoki A Inoue K Makide N Saiki H Arai 2007 Structure and function of extracellular phospholipase A1 belonging to the pancreatic lipase gene family Biochimie 89 197 204 17101204 10.1016/j.biochi.2006.09.021 1:CAS:528: DC%2BD2sXhtlaqs7s%3D (Pubitemid 46161954)
2. P Artursson K Palm K Luthman 2001 Caco-2 monolayers in experimental and theoretical predictions of drug transport Adv Drug Deliv Rev 46 27 43 11259831 10.1016/S0169-409X(00)00128-9 1:CAS:528:DC%2BD3MXitVOhs7s%3D
3. M Asai S Higuchi M Kubota K Iguchi S Usui K Hirano 2006 Regulators for blood glucose level affect gene expression of aquaporin 3 Biol Pharm Bull 29 991 996 16651733 10.1248/bpb.29.991 1:CAS:528:DC%2BD28Xmt1ehtLg%3D
4. ST Ballard JH Hunter AE Taylor 1995 Regulation of tight-junction permeability during nutrient absorption across the intestinal epithelium Annu Rev Nutr 15 35 55 8527224 10.1146/annurev.nu.15.070195.000343 1:CAS:528:DyaK2MXntVCjsr4%3D
5. R Buesen M Mock A Seidel J Jacob A Lampen 2002 Interaction between metabolism and transport of benzo[a]pyrene and its metabolites in enterocytes Toxicol Appl Pharmacol 183 168 178 12383708 10.1006/taap.2002.9484 1:CAS:528:DC%2BD38Xntlyhu7g%3D (Pubitemid 35168491)
6. D Chateau T Pauquai F Delers M Rousset J Chambaz S Demignot 2005 Lipid micelles stimulate the secretion of triglyceride-enriched apolipoprotein B48-containing lipoproteins by Caco-2 cells J Cell Physiol 202 767 776 15389567 10.1002/jcp.20173 1:CAS:528:DC%2BD2MXhtFOnu78%3D (Pubitemid 40175852)
7. WS Cho BS Han KT Nam K Park M Choi SH Kim J Jeong DD Jang 2008 Carcinogenicity study of 3-monochloropropane-1, 2-diol in Sprague-Dawley rats Food Chem Toxicol 46 3172 3177 18680782 10.1016/j.fct.2008.07.003 1:CAS:528:DC%2BD1cXhtVKnsbbK
8. WS Cho BS Han H Lee C Kim KT Nam K Park M Choi SJ Kim SH Kim J Jeong DD Jang 2008 Subchronic toxicity study of 3-monochloropropane-1,2-diol administered by drinking water to B6C3F1 mice Food Chem Toxicol 46 1666 1673 18328611 10.1016/j.fct.2007.12.030 1:CAS:528:DC%2BD1cXjs1Khsrs%3D
9. JN Cogburn MG Donovan CS Schasteen 1991 A model of human small intestinal absorptive cells. 1. Transport barrier Pharm Res 8 210 216 2023869 10.1023/A:1015844104539 1:CAS:528:DyaK3MXhtF2isLs%3D
10. PD Collier DDO Cromie AP Davies 1991 Mechanism of formation of chloropropanols present in protein hydrolysates J AOCS 68 785 790 1:CAS:528:DyaK38XhtVClsLY%3D
11. Deutsche Gesellschaft für Fettwissenschaft: DGF Standard Method C III 18 (2009) Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and glycidol (glycidyl esters). Determination in fats and oils by GC-MS. Deutsche Einheitsmethoden zur Untersuchung von Fetten, Fettprodukten, Tensiden und verwandten Stoffen, Wissenschaftliche Verlagsgesellschaft, Stuttgart (Germany)
12. V Divinova B Svejkovska M Dolezal J Velisek 2004 Determination of free and bound 3-Chloropropane-1, 2-diol by gas chromatography with mass spectrometric detection using deuterated 3-chloropropane-1,2-diol as internal standard Czech J Food Sci 22 182 189 1:CAS:528:DC%2BD2MXotFCmtg%3D%3D (Pubitemid 40008125)
13. B Ebert A Seidel A Lampen 2005 Identification of BCRP as transporter of benzo[a]pyrene conjugates metabolically formed in Caco-2 cells and its induction by Ah-receptor agonists Carcinogenesis 26 1754 1763 15917307 10.1093/carcin/bgi139 1:CAS:528:DC%2BD2MXhtVWnt7fN (Pubitemid 41487991)
14. R El Ramy M Ould Elhkim S Lezmi JM Poul 2007 Evaluation of the genotoxic potential of 3-monochloropropane-1,2-diol (3-MCPD) and its metabolites, glycidol and beta-chlorolactic acid, using the single cell gel/comet assay Food Chem Toxicol 45 41 48 16971032 10.1016/j.fct.2006.07.014 1:CAS:528:DC%2BD28Xht1ChsrfP (Pubitemid 44810906)
15. European Commission 2001 Commission Regulation No 466/2001. Setting maximum levels for certain contaminants in foodstuffs Off J Eur Communities 2001 L364 5 24
16. Federal Institute for Risk Assessment (2007) BfR opinion 047/2007. Infant formula and follow-up formula may contain harmful 3-MCPD fatty acid esters. http://www.bfr.bund.de/cm/245/infant-formula-and-follow-up-formula-may-contain- harmful-3-mcpd-fatty-acid-esters.pdf
17. CG Hamlet PA Sadd 2004 Chloropropanols and their esters in baked cereal products Czech J Food Sci 22 259 262 1:CAS:528:DC%2BD2cXhtVaitrfJ
18. CG Hamlet PA Sadd C Crews J Velísek DE Baxter 2002 Occurrence of 3-chloro-propane-1,2-diol (3-MCPD) and related compounds in foods: a review Food Addit Contam 19 619 631 12113657 10.1080/02652030210132391 1:CAS:528: DC%2BD38XlvFens7w%3D (Pubitemid 34823521)
19. AR Jones P Gadiel D Stevenson 1981 The fate of oxalic acid in the Wistar rat Xenobiotica 11 385 390 7293229 10.3109/00498258109045849 1:CAS:528:DyaL38Xjt1Wkug%3D%3D (Pubitemid 11052577)
20. MS Levin VD Talkad JI Gordon WF Stenson 1992 Trafficking of exogenous fatty acids within Caco-2 cells J Lipid Res 33 9 19 1552237 1:CAS:528: DyaK38XhtVehsrY%3D
21. W Liao L Chan 2000 Apolipoprotein B, a paradigm for proteins regulated by intracellular degradation, does not undergo intracellular degradation in CaCo2 cells J Biol Chem 275 3950 3956 10660549 10.1074/jbc.275.6.3950 1:CAS:528:DC%2BD3cXht12gs7Y%3D (Pubitemid 30094621)
22. M Pinto S Robine-Leon MD Appay N Kedinger N Triadou E Dussaulx P Lacroix K Simon-Assman K Haffen J Fogh A Zwiebaum 1983 Enterocyte like differentiation and polarization of the human colon carcinoma cell line Caco-2 in culture Biol Cell 47 323 330 (Pubitemid 14236699)
23. S Robjohns R Marshall M Fellows G Kowalczyk 2003 In vivo genotoxicity studies with 3-monochloropropan-1,2-diol Mutagenesis 18 401 404 12960406 10.1093/mutage/geg017 1:CAS:528:DC%2BD3sXnt1Kisr0%3D (Pubitemid 37098969)
24. W Seefelder N Varga A Studer G Williamson FP Scanlan RH Stadler 2008 Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD Food Addit Contam Part A Chem Anal Control Expo Risk Assess 25 391 400 18348037 1:CAS:528:DC%2BD1cXjtlSrt7g%3D (Pubitemid 351420236)
25. JH Spalinger EG Seidman D Ménard E Levy 1998 Endogenous lipase activity in Caco-2 cells Biochim Biophys Acta 1393 119 127 9714771 1:CAS:528:DyaK1cXkvFOntb0%3D (Pubitemid 28495596)
26. B Sveikovská O Novotny V Divinova Z Reblova M Dolezal J Velísek 2004 Esters of 3-chloropropane-1, 2-diol in foodstuffs Czech J Food Sci 22 190 196
27. PJ Trotter J Storch 1993 Fatty acid esterification during differentiation of the human intestinal cell line Caco-2 J Biol Chem 268 10017 10023 8387510 1:CAS:528:DyaK3sXks1yqsL4%3D (Pubitemid 23150176)
28. J Velísek J Davídek J Hajslová V Kubelka G Janícek B Mánková 1978 Chlorohydrins in protein hydrolysates Z Lebensm Unters Forsch 167 241 244 716635 10.1007/BF01135595
29. J Velísek J Davídek V Kubelka G Janícek Z Svobodová Z Simicová 1980 New chlorine-containing organic compounds in protein hydrolysates J Agric Food Chem 28 1142 1144 7451739 10.1021/jf60232a022
30. Z Zelinková B Svejkovská J Velísek M Dolezal 2006 Fatty acid esters of 3-chloropropane-1,2-diol in edible oils Food Addit Contam 23 1290 1298 17118872 10.1080/02652030600887628 (Pubitemid 44803819)