Relative oral bioavailability of glycidol from glycidyl fatty acid esters in rats

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• 作者：Klaus E. Appel (1)
  Klaus Abraham (1)
  Edith Berger-Preiss (2)
  Tanja Hansen (2)
  Elisabeth Apel (2)
  Sven Schuchardt (2)
  Carla Vogt (3)
  Nadiya Bakhiya (1)
  Otto Creutzenberg (2)
  Alfonso Lampen (1)
  
• 关键词：Glycidol ; Glycidyl fatty acid esters ; Relative bioavailability ; Kinetics ; Risk assessment
• 刊名：Archives of Toxicology
• 出版年：2013
• 出版时间：September 2013
• 年：2013
• 卷：87
• 期：9
• 页码：1649-1659
• 全文大小：488KB
• 参考文献：1. Abraham K, Appel KE, Berger-Preiss E, Apel E, Gerling S, Mielke H, Creutzenberg O, Lampen A (2013) Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats. Arch Toxicol 87(4):649鈥?59
  2. Bader M, Rosenberger W, Gutzki FM, Tsikas D (2009) Quantification of N-(3-chloro-2-hydroxypropyl)valine in human haemoglobin as a biomarker of epichlorohydrin exposure by gas chromatography-tandem mass spectrometry with stable-isotope dilution. J Chromatogr B Anal Technol Biomed Life Sci 877(13):1402鈥?410 CrossRef
  3. Bakhiya N, Abraham K, Gurtler R, Appel KE, Lampen A (2011) Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acid esters in food. Mol Nutr Food Res 55:509鈥?21 CrossRef
  4. Belov VN, M眉ller M, Ignatenko O, Hallier E, de Meijere A (2005) Facile access to isotopically labelled valylleucyl anilides as biomarkers for the quantification of hemoglobin adducts to toxic electrophiles. Eur J Org Chem 23:5094鈥?099 CrossRef
  5. BfR (Bundesinstitut f眉r Risikobewertung) (2009) Initial evaluation of the assessment of levels of glycidol fatty acid esters detected in refined vegetable fats, BfR opinion No. 007/2009, 10 March 2009. glycidol_fatty_acid_esters.pdf" class="a-plus-plus">http://www.bfr.bund.de/cm/245/initial_evaluation_of_the_assessment_of_levels_of_glycidol_fatty_acid_esters.pdf. Accessed Nov 2012
  6. Crews C, Chiodini A, Granvogl M, Hamlet C, Hrncirik K, Kuhlmann J, Lampen A, Scholz G, Weisshaar R, Wenzl T, Jasti PR, Seefelder W (2012) Analytical approaches for MCPD esters and glycidyl esters in food and biological samples: a review and future perspectives. Food Addit Contam Part A. doi:10.1080/19440049.2012.720385
  7. DFG (2000) German Research Foundation (DFG) senate commission for the investigation of health hazards of chemical compounds in the work area (MAK commission). Wiley-VCH, Weinheim
  8. Eckert E, Drexler H, G枚en T (2010) Determination of six hydroxyalkyl mercapturic acids in human urine using hydrophilic interaction liquid chromatography with tandem mass spectrometry (HILIC-ESI-MS/MS). J Chromatogr B Anal Technol Biomed Life Sci 878(27):2506鈥?514 CrossRef
  9. Eckert E, Schmid K, Schaller B, Hiddemann-Koca K, Drexler H, Goen T (2011) Mercapturic acids as metabolites of alkylating substances in urine samples of German inhabitants. Int J Hyg Environ Health 214:196鈥?04 CrossRef
  10. Hamlet CG, Asuncion L, Veli拧ek J, Dole藕al M, Zelinkov谩 Z, Crews C (2011) Formation and occurrence of esters of 3-chloro-propane-1,2-diol (3-CPD) in foods: what we know and what we assume. Eur J Lipid Sci Technol 113:279鈥?03 CrossRef
  11. Hinds酶 Landin H, Osterman-Golkar S, Zorcec V, T枚rnqvist M (1996) Biomonitoring of epichlorohydrin by hemoglobin adducts. Anal Biochem 240(1):1鈥? CrossRef
  12. Hinds酶 Landin H, Grummt T, Laurent C, Tates A (1997) Monitoring of occupational exposure to epichlorohydrin by genetic effects and hemoglobin adducts. Mutat Res 381:217鈥?26
  13. Hinds酶 Landin H, Segerb盲ck D, Damberg C, Osterman-Golkar S (1999) Adducts with haemoglobin and DNA in epichlorohydrin-exposed rats. Chem Biol Interact 117:49鈥?4 CrossRef
  14. Hinds酶 Landin H, Tareke E, Rydberg P, Olsson U, T枚rnqvist M (2000) Heating of food and haemoglobin adducts from carcinogens: possible precursor role of glycidol. Food Chem Toxicol 38(11):963鈥?69 CrossRef
  15. Honda H, Fujii K, Yamaguchi T, Ikeda N, Nishiyama N, Kasamatsu T (2012) Glycidol exposure evaluation of humans who have ingested diacylglycerol oil containing glycidol fatty acid esters using hemoglobin adducts. Food Chem Toxicol 50:4163鈥?168 CrossRef
  16. IARC (2000) Some industrial chemicals, IARC monograph on the evaluation of carcinogenic risk of chemicals to humans, vol. 77, International Agency for Research on Cancer, Lyon, France pp. 469鈥?86. http://monographs.iarc.fr/ENG/Monographs/vol77/mono77-19.pdf. Accessed Nov 2012
  17. Jones AR (1975) The metabolism of 3-chloro,-3-bromo- and 3-iodopropan-1,2-diol in rats and mice. Xenobiotica 5(3):155鈥?65 CrossRef
  18. Lynch BS, Bryant DB, Hook GJ, Nestmann ER, Munro LC (1998) Carcinogenicity of monochloro-1,2-propanediol (alpha-chlorohydrin, 3-MCPD). Int J Toxicol 17:47鈥?6
  19. Masukawa Y, Shiro H, Nakamura S, Kondo N, Jin N, Suzuki N, Ooi N, Kudo N (2010) A new analytical method for the quantification of glycidol fatty acid esters in edible oils. J Oleo Sci 59:81鈥?8 CrossRef
  20. Mowrer J, T枚rnqvist M, Jensen S, Ehrenberg L (1986) Modified Edman degradation applied to hemoglobin for monitoring occupational exposure to alkylating agents. Toxicol Environ Chem 11(3):215鈥?31 CrossRef
  21. M眉ller M, Belov V, de Meijere A, B眉nger J, Emmert B, Heutelbeck A, Hallier E (2005) Entwicklung eines neuen Biomonitoringverfahrens zur Bestimmung des H盲moglobinadduktes N-(2,3-Dihydroxypropyl)-Valin nach Epichlorhydrinexposition. Arbeitsmed Sozialmed Umweltmed 40(3):171
  22. Nomeir AA, Silveira DM, Ferrala NF, Markham PM, McComish MF, Ghanayem BI, Chadwick M (1995) Comparative disposition of 2,3-epoxy-1-propanol (glycidol) in rats following oral and intravenous administration. J Toxicol Environ Health 44:203鈥?17 CrossRef
  23. NTP (1990) National Toxicology Program, Toxicology and carcinogenesis studies of glycidol (CAS No. 556-52-5) in F344/N rats and B6C3F1 mice (gavage studies). Technical Report Series No. 374. NIH Publication No. 90-2829. Research Triangle Park, NC. http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr374.pdf. Accessed Nov 2012
  24. Shimizu M, Kudo N, Shiro H, Yasunaga K, Masukawa Y, Katsuragi Y, Yasumasu T (2010) Comparison of indirect and direct quantification of glycidol fatty acid ester in edible oils. J Oleo Sci 59:535鈥?39 CrossRef
  25. Van Sittert NJ (1996) N-2-Cyanoethyl-Valin, N-2-Hydroxyethyl-Valin, N-Methyl-Valin (zum Nachweis einer Belastung/Beanspruchung durch Acrylnitril, Ethylenoxid ssowie methylierende Substanzen). In: Hartwig A (ed) Analytische Methoden zur Pr眉fung gesundheitssch盲dlicher Arbeitsstoffe, Band 2: Analysen in biologischen Material, 12. Lieferung ed, Wiley-VCH, Weinheim, pp 1鈥?1
  26. Wakabayashi K, Kurata Y, Harada T, Tamaki Y, Nishiyama N, Kasamatsu T (2012) Species differences in toxicokinetic parameters of glycidol after a single dose of glycidol or glycidol linoleate in rats and monkeys. J Toxicol Sci 37:691鈥?98 CrossRef
  27. Wei脽haar R (2011) Fatty acid esters of 3-MCPD: overview of occurrence and exposure estimates. Eur J Lipid Sci Technol 113:304鈥?08 CrossRef
  
• 作者单位：Klaus E. Appel (1)
  Klaus Abraham (1)
  Edith Berger-Preiss (2)
  Tanja Hansen (2)
  Elisabeth Apel (2)
  Sven Schuchardt (2)
  Carla Vogt (3)
  Nadiya Bakhiya (1)
  Otto Creutzenberg (2)
  Alfonso Lampen (1)
  
  1. Department of Food Safety, Federal Institute for Risk Assessment (BfR), Max-Dohrn-Str. 8鈥?0, 10589, Berlin, Germany
  2. Fraunhofer Institute for Toxicology and Experimental Medicine, Nikolai-Fuchs-Str. 1, 30625, Hannover, Germany
  3. Institute for Inorganic Chemistry, Leibniz University of Hannover, Callinstr. 9, 30167, Hannover, Germany
  
• ISSN：1432-0738

文摘

In order to quantify the relative bioavailability of glycidol from glycidyl fatty acid esters in vivo, glycidyl palmitoyl ester and glycidol were orally applied to rats in equimolar doses. The time courses of the amounts of glycidol binding to hemoglobin as well as the excretion of 2,3-dihydroxypropyl mercapturic acids were determined. The results indicate that glycidol is released from the glycidyl ester by hydrolysis and rapidly distributed in the organism. In relation to glycidol, there was only a small timely delay in the binding to hemoglobin for the glycidol moiety released from the ester which may be certainly attributed to enzymatic hydrolysis. In both cases, however, an analogous plateau was observed representing similar amounts of hemoglobin binding. With regard to the urinary excretion of mercapturic acids, also similar amounts of dihydroxypropyl mercapturic acids could be detected. In an ADME test using a virtual double tag (3H, 14C) of glycidyl palmitoyl ester, a diverging isotope distribution was detected. The kinetics of the 14C-activity reflected the kinetics of free glycidol released after hydrolysis of the palmitoyl ester. In view of this experimental data obtained in rats, it is at present justified for the purpose of risk assessment to assume complete hydrolysis of the glycidyl ester in the gastrointestinal tract. Therefore, assessment of human exposure to glycidyl fatty acid ester should be regarded as an exposure to the same molar quantity of glycidol.