Skip to main content
Applied Biological Chemistry
Download PDF
  • Article
  • Published:

In vitro metabolism of flucetosulfuron by artificial gastrointestinal juices

Journal of the Korean Society for Applied Biological Chemistry volume 57, pages 397–405 (2014)Cite this article

Abstract

To investigate the metabolism of pesticides by gastrointestinal (GI) juices, artificial GI juices were incubated with threo- and erythro-isomers of flucetosulfuron. The metabolites produced in each reaction mixture of artificial GI juices were unambiguously identified using liquid chromatography-tandem mass spectrometry. Flucetosulfuron was observed to be stable in saliva. However, in the intestinal juices, approximately 18% of flucetosulfuron was degraded, producing N-(4,6-dimethoxypyrimidin-2-ylcarbomoyl)-2-(2-fluoro-1-hydroxypropyl)pyrimidine-3-sulfonamid (M1). In artificial gastric juices, about 85% of flucetosulfuron was rapidly degraded, producing the metabolites 2-(2-fluoro-1-hydroxypropyl) pyridine-3-sulfonamide (M2), 4,6-dimethoxypyrimidin-2-amine (M3), and 2-fluoro-1-(3-sulfamoylpyridin-2-yl)propyl 2-methoxyacetate (M4). These results indicate that the sulfonylurea bridge and ester bond of flucetosulfuron are hydrolyzed in artificial GI juices. No significant differences were noted in the degradation patterns between the two isomers of flucetosulfuron in the artificial GI juices that were tested. Considering the rapid degradation of flucetosulfuron in vitro by artificial GI juices, it is likely that there would be no significant absorption of flucetosulfuron from the GI tract into the blood stream after oral administration.

References

  • Abass K, Turpeinen M, Rautio A, Hakkola J, and Pelkonen O (2012) Metabolism of pesticides by human cytochrome P450 enzymes in vitro-a survey. In Insecticides-advances in integrated pest management, Perveen F (ed.), pp. 165–94. Intech Europe, Croatia.

    Google Scholar 

  • Abrahamsson B, Albery T, Eriksson A, Gustafsson I, and Sjberg M (2004) Food effects on tablet disintegration. Europ J Pharmaceu Sci 22, 165–72.

    Article  CAS  Google Scholar 

  • Adenugba AA, Mcmartin DW, and Beck AJ (2008) In vitro approaches to assess bioavailability and human gastrointestinal mobilization of foodborne polychlorinated biphenyls (PCBs). J Environ Sci Health 43, 410–21.

    Article  CAS  Google Scholar 

  • Borgström B, Dahlqvist A, Lundh G, and Sjövall J (1957) Studies of intestinal digestion and absorption in the human. J Clin Invest 36, 15–1.

    Article  Google Scholar 

  • Chang SS, Lu TH, Eddleston M, Konradsen F, Sterne JA, Lin JJ et al. (2012) Factors associated with the decline in suicide by pesticide poisoning in Taiwan: A time trend analysis, 1987–2010. Clin Tox 50, 471–80.

    Article  Google Scholar 

  • Esteban M and Castaño A (2009) Non-invasive matrices in human biomonitoring: A review. Environ Int 35, 438–49.

    Article  CAS  Google Scholar 

  • Ganong WF and Barrett KE (2005) Digestion & Absorption. In Review of medical physiology. pp. 384–93. McGraw-Hill Medical New York, USA.

    Google Scholar 

  • Gorbach SL, Barakat S, and Gualtieri L (1992) Survival of Lactobacillus species (strain GG) in human gastrointestinal tract. Digest Diseas Sci 37, 121–8.

    Article  Google Scholar 

  • Gray J and Bucher GR (1941) The composition of gastric juice as a function of the rate of secretion. Americ J Physic-Leg Cont 133, 542–50.

    CAS  Google Scholar 

  • Humphrey SP and Williamson RT (2001) A review of saliva: normal composition, flow, and function. J Prosth Dent 85, 162–9.

    Article  CAS  Google Scholar 

  • Hur SJ, Lim BO, Decker EA, and McClements DJ (2011) In vitro human digestion models for food applications. Food Chem 125, 1–12.

    Article  CAS  Google Scholar 

  • Jei MS (1992) A Study on the Misuses of Pesticides for Suicides. Kor Soc Pub Health Nurs 6, 62–70.

    Google Scholar 

  • Lee HK, Moon JK, Chang CH, Choi H, Park HW, Park BS et al. (2006) Stereoselective metabolism of endosulfan by human liver microsomes and human cytochrome P450 isoforms. Drug Metab Dispos 34, 1090–5.

    Article  CAS  Google Scholar 

  • Lee JH (2008) Fate of boscalid on cucumber and its metabolism in in vitro biological system. MS Thesis, Seoul National University, Korea.

    Google Scholar 

  • Lee MG, Shim JH, Ko S, and Chung HR (2010) Research trends on the development of scientific evidence on the domestic maximum residue limits of pesticides. Food Sci Ind 43, 41–66.

    Google Scholar 

  • Lee S (2010) The occupational diseases of agricultural workers. Hanyang Med Review 30, 305–12.

    Article  Google Scholar 

  • Lee YS, Liu KH, Moon JK, Ko BJ, Choi H, Hwang KS et al. (2014) In vitro metabolism of flucetosulfuron by human liver microsomes. J Agr Food Chem 62, 3057–63.

    Article  CAS  Google Scholar 

  • Lian WC, Hsiao HC, and Chou CC (2003) Viability of microencapsulated bifidobacteria in simulated gastric juice and bile solution. Int J Food Microbiol 86, 293–301.

    Article  Google Scholar 

  • Lu C, Irish R, and Fenske R (2003) Biological monitoring of diazinon exposure using saliva in an animal model. J Toxicol Environ Health 66, 2315–25.

    Article  CAS  Google Scholar 

  • Nigg HN, Stamper JH, and Mallory L (1993) Quantification of human exposure to ethion using saliva. Chemosphere 26, 897–906.

    Article  CAS  Google Scholar 

  • Rao A, Shiwnarain N, and Maharaj I (1989) Survival of microencapsulated Bifidobacterium pseudolongum in simulated gastric and intestinal juices. Canadian Inst Food Sci Tech J 22, 345–9.

    Article  Google Scholar 

  • Roh S (2012) Work-related diseases of agricultural workers in south korea. J Kor Med Assoc 55, 1063–9.

    Article  Google Scholar 

  • Tao S, Li L, Ding J, Zhong J, Zhang D, Lu Y et al. (2010) Mobilization of Soil-Bound Residue of Organochlorine Pesticides and Polycyclic Aromatic Hydrocarbons in an in vitro Gastrointestinal Model. Environ Sci Tech 45, 1127–32.

    Article  Google Scholar 

  • Tao S, Lu Y, Zhang D, Yang Y, Yang Y, Lu X et al. (2009) Assessment of oral bioaccessibility of organochlorine pesticides in soil using an in vitro gastrointestinal model. Environ Sci Tech 43, 4524–9.

    Article  CAS  Google Scholar 

  • Timchalk C, Campbell JA, Liu G, Lin Y, and Kousba AA (2007) Development of a non-invasive biomonitoring approach to determine exposure to the organophosphorus insecticide chlorpyrifos in rat saliva. Toxicol appl Pharm 219, 217–25.

    Article  CAS  Google Scholar 

  • Versantvoort CH, Oomen AG, Van de Kamp E, Rompelberg CJ, and Sips AJ (2005) Applicability of an in vitro digestion model in assessing the bioaccessibility of mycotoxins from food. Food Chem Toxico 43, 31–40.

    Article  CAS  Google Scholar 

  • Virkel G, Carletti M, Cantiello M, Della Donna L, Gardini G, Girolami F et al. (2009) Characterization of xenobiotic metabolizing enzymes in bovine small intestinal mucosa. J Vet Pharm Thera 33, 295–303.

    Article  Google Scholar 

  • Yang AG, Shim KH, Choi OJ, Park JH, Do JH, Hwang IG et al. (2012) Establishment of the Korean total diet study (TDS) model in consideration to pesticide intake. Korean Soc Pest Sci 16, 151–62.

    Google Scholar 

  • Yang SK, Chang WC, and Huang JD (1993) Effects of sodium fluoride and cobalt chloride on the enantioselectivity of microsomal and cytosolic esterases in rat intestinal mucosa. Biochem Pharm 46, 1511–4.

    Article  CAS  Google Scholar 

  • Young J and Schneyer CA (1981) Composition of saliva in mammalia. Austral J Exp Bio Med Sci 59, 1–53.

    Article  CAS  Google Scholar 

  • Zhang J and Li Z (2012) Characteristics of Chinese rural young suicides by pesticides. Int J Soci Psych 59, 655–62.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Agricultural Biotechnology and Research Institute for Agriculture and Life Sciences, Seoul National University, Seoul, 151-742, Republic of Korea

    Yong-Sang Lee, Eunhye Kim & Jeong-Han Kim

  2. School of Plant, Life and Environmental Sciences, Hankyong National University, Ansung, 456-749, Republic of Korea

    Joon-Kwan Moon

  3. College of Pharmacy and Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu, 702-701, Republic of Korea

    Kwang-Hyeon Liu

  4. Ministry of Food and Drug Safety, Cheongwon, 63-951, Republic of Korea

    Hoon Choi

  5. LG Life Sciences, Onsan-eup, Ulsan, 689-896, Republic of Korea

    Yong-Sang Lee

Authors
  1. Yong-Sang Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joon-Kwan Moon
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kwang-Hyeon Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eunhye Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hoon Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jeong-Han Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jeong-Han Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lee, YS., Moon, JK., Liu, KH. et al. In vitro metabolism of flucetosulfuron by artificial gastrointestinal juices. J Korean Soc Appl Biol Chem 57, 397–405 (2014). https://doi.org/10.1007/s13765-014-4027-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13765-014-4027-y

Keywords