Advanced search
Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 53, 2023 - Issue 1
Submit an article Journal homepage
119
Views
3
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

2-Oxidation, 3-methyl hydroxylation, and 6-hydroxylation of skatole, a contributor to the odour of boar-tainted pork meat, mediated by porcine liver microsomal cytochromes P450 1A2, 2A19, 2E1, and 3A22

Yasuhiro Unoa Department of Basic Veterinary Science, Joint Faculty of Veterinary Medicine, Kagoshima University, Kagoshima-city, JapanCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0001-9040-1681View further author information
ORCID Icon,
Saho Morikunib Laboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, JapanView further author information
,
Norie Murayamab Laboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, JapanView further author information
&
Hiroshi Yamazakib Laboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, JapanCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-1068-4261View further author information
ORCID Icon
Pages 60-65 | Received 04 Mar 2023, Accepted 27 Mar 2023, Published online: 05 Apr 2023

References

  • Achour B, Barber J, Rostami-Hodjegan A. 2011. Cytochrome P450 Pig liver pie: determination of individual cytochrome P450 isoform contents in microsomes from two pig livers using liquid chromatography in conjunction with mass spectrometry. Drug Metab Dispos. 39(11):2130–2134.
  • Bæk C, Hansen-Møller J, Friis C, Cornett C, Hansen SH. 1997. Identification of selected metabolites of skatole in plasma and urine from pigs. J Agric Food Chem. 45(6):2332–2340.
  • Buyssens L, De Clerck L, Schelstraete W, Dhaenens M, Deforce D, Ayuso M, Van Ginneken C, Van Cruchten S. 2021. Hepatic cytochrome P450 abundance and activity in the developing and adult gottingen minipig: pivotal data for PBPK modeling. Front Pharmacol. 12:665644.
  • Diaz GJ, Skordos KW, Yost GS, Squires EJ. 1999. Identification of phase I metabolites of 3-methylindole produced by pig liver microsomes. Drug Metab Dispos. 27(10):1150–1156.
  • Diaz GJ, Squires EJ. 2000. Metabolism of 3-methylindole by porcine liver microsomes: responsible cytochrome P450 enzymes. Toxicol Sci. 55(2):284–292.
  • Lin Z, Lou Y, Squires EJ. 2004. Molecular cloning, expression and functional characterization of the cytochrome P450 2A6 gene in pig liver. Anim Genet. 35(4):314–316.
  • Matal J, Matuskova Z, Tunkova A, Anzenbacherova E, Anzenbacher P. 2009. Porcine CYP2A19, CYP2E1 and CYP1A2 forms are responsible for skatole biotransformation in the reconstituted system. Neuro Endocrinol Lett. 30 (Suppl 1):36–40.
  • Millecam J, De Clerck L, Govaert E, Devreese M, Gasthuys E, Schelstraete W, Deforce D, De Bock L, Van Bocxlaer J, Sys S, et al. 2018. The ontogeny of cytochrome P450 enzyme activity and protein abundance in conventional pigs in support of preclinical pediatric drug research. Front Pharmacol. 9:470.
  • Murayama N, Yamazaki H. 2021. Metabolic activation and deactivation of dietary-derived coumarin mediated by cytochrome P450 enzymes in rat and human liver preparations. J Toxicol Sci. 46(8):371–378.
  • Rasmussen MK, Scavenius C, Gerbal-Chaloin S, Enghild J. 2019. Sex dictates the constitutive expression of hepatic cytochrome P450 isoforms in Gottingen minipigs. Toxicol Lett. 314:181–186.
  • Rasmussen MK, Zamaratskaia G. 2014. Regulation of porcine hepatic cytochrome p450 - implication for boar taint. Comput Struct Biotechnol J. 11(19):106–112.
  • Sakai C, Iwano S, Shimizu M, Onodera J, Uchida M, Sakurada E, Yamazaki Y, Asaoka Y, Imura N, Uno Y, et al. 2016. Analysis of gene expression for microminipig liver transcriptomes using parallel long-read technology and short-read sequencing. Biopharm Drug Dispos. 37(4):220–232.
  • Skaanild MT, Friis C. 1999. Cytochrome P450 sex differences in minipigs and conventional pigs. Pharmacol Toxicol. 85(4):174–180.
  • Skaanild MT, Friis C. 2005. Porcine CYP2A polymorphisms and activity. Basic Clin Pharmacol Toxicol. 97(2):115–121.
  • Thornton-Manning J, Appleton ML, Gonzalez FJ, Yost GS. 1996. Metabolism of 3-methylindole by vaccinia-expressed P450 enzymes: correlation of 3-methyleneindolenine formation and protein-binding. J Pharmacol Exp Ther. 276(1):21–29.
  • Uno Y, Jikuya S, Noda Y, Oguchi A, Murayama N, Kawaguchi H, Tsukiyama-Kohara K, Yamazaki H. 2023. Newly identified cytochrome P450 3A genes of tree shrews and pigs are expressed and encode functional enzymes. Comp Biochem Physiol C Toxicol Pharmacol. 267:109579.
  • Uno Y, Morikuni S, Shiraishi M, Asano A, Kawaguchi H, Murayama N, Yamazaki H. 2022. A comprehensive analysis of six forms of cytochrome P450 2C (CYP2C) in pigs. Xenobiotica. 52(9-12):963–972.
  • Uno Y, Murayama N, Ijiri M, Kawaguchi H, Yamato O, Shiraishi M, Asano A, Teraoka H, Mizukawa H, Nakayama SMM, et al. 2022. Cytochrome P450 2J Genes Are Expressed in Dogs, Cats, and Pigs, and Encode Functional Drug-Metabolizing Enzymes. Drug Metab Dispos. 50(11):1434–1441.
  • Uno Y, Ushirozako G, Uehara S, Murayama N, Fujiki Y, Kawaguchi H, Tsukiyama-Kohara K, Yamazaki H. 2022. Newly identified tree shrew cytochrome P450 2B6 (CYP2B6) and pig CYP2B6b are functional drug-metabolising enzymes. Xenobiotica. 52(7):687–696.
  • Ushirozako G, Noda Y, Murayama N, Kawaguchi H, Tsukiyama-Kohara K, Yamazaki H, Uno Y. 2023. Newly identified tree shrew cytochrome P450 2A13 (CYP2A13) is expressed in liver and lung and encodes a functional drug-metabolizing enzyme similar to dog CYP2A13 and Pig CYP2A19. Drug Metab Dispos. https://dmd.aspetjournals.org/content/early/2023/03/06/dmd.122.001152.
  • Wiercinska P, Lou Y, Squires EJ. 2012. The roles of different porcine cytochrome P450 enzymes and cytochrome b5A in skatole metabolism. Animal. 6(5):834–845.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.