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Inhibition of β-glucuronidase by chlorinated hydroquinones and benzoquinones

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Abstract

An earlier study of the metabolism of pentachlorophenol has shown that a metabolite, tetrachloro-p-hydroquinone, possessed pronounced inhibitory action on the activity of β-glucuronidase from bacterial origin. Several other chlorinated hydroquinones and benzoquinones have now been studied with regard to their ability to inhibit β-glucuronidase of various origin in vitro and in vivo.

All the studied chlorinated hydroquinones and benzoquinones were found to be potent inhibitors of β-glucuronidase of bacterial origin. D-glucaric acid-1.4-lactone was included for comparison and was found to be less active than the other studied compounds. The inhibition was found to be competitive in nature.

No inhibitory effect of the benzo- and hydroquinones studied in vitro or in vivo could be demonstrated on β-glucuronidase from livers. The result calls for precaution when using bacterial β-glucuronidase to split urinary conjugates of glucuronic acid.

Zusammenfassung

Eine frühere Studie des Metabolismus von Pentachlorphenol hat gezeigt, daß ein Metabolit, Tetrachlor-p-hydrochinon, eine ausgesprochene Hemmwirkung auf die Aktivität der Bakterien-β-Glucuronidase besitzt. Verschiedene andere chlorierte Hydrochinone und Benzochinone sind jetzt auf ihre Fähigkeit, β-Glucuronidase anderen Ursprungs zu hemmen, in vitro und in vivo, untersucht worden.

Alle die untersuchten chlorierten Hydrochinone und Benzochinone zeigten sich als starke Hemmer der Bakterien β-Glucuronidase. D-Glucarsäure-1.4-Lakton wurde zum Vergleich einbezogen und wurde weniger aktiv als die anderen Verbindungen befunden. Die Hemmung war kompetitiver Art.

Kein Hemmungseffekt von Hydro-oder Benzochinonen konnte in vitro oder in vivo auf Leber-β-Glucuronidase gezeigt werden. Das Resultat mahnt zur Vorsieht, wenn Bakterien β-Glucuronidase zur Spaltung von Harnkonjugaten der Glucuronsäure angewandt wird.

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References

  1. Ahlborg, U. G., Lindgren, J.-E., Mercier, M.: Metabolism of pentachlorophenol. Arch. Toxicol. 32, 271–281 (1974)

  2. Ahlborg, U. G., Larsson, K.: Metabolism of tetrachlorophenols in the rat. To be published (1977)

  3. Graebe, C.: Untersuchungen über die Chinongruppe. Ann. Chem. Pharm. 146, 22–30 (1868)

  4. Hayashi, M.: Distribution of β-glucuronidase activity in rat tissues employing the naphtol AS-BI glucuronide hexazonium pararosanilin method. J. Histochem. Cytochem. 12, 659–669 (1964)

  5. Kuwahara, M., Kato, N., Munakata, K.: The photochemical reaction products of pentachlorophenol. Agr. Biol. Chem. (Japan) 29, 880 (1965)

  6. Kuwahara, M., Kato, N., Munakata, K.: The photochemical reaction of pentachlorophenol. Part I. The structure of the yellow compound. Agr. Biol. Chem. (Japan) 30, 232 (1966a)

  7. Kuwahara, M., Kato, N., Munakata, K.: The photochemical reaction of pentachlorophenol. Part II. The chemical structure of minor products. Agr. Biol. Chem. (Japan) 30, 239 (1966b)

  8. Lowry, O. H., Rosebrough, N. J., Farr, A. L., Randall, R. J.: Protein measurement with the folin phenol reagent. J. biol. Chem. 193, 265–275 (1951)

  9. Miller, G. L.: Protein determination for large numbers of samples. Anal. Chem. 31, 964 (1959)

  10. Tashiro, S., Sasmoto, T., Aikawa, T., Tokunaga, S., Taniguchi, E., Morifusa, E.: Metabolism of pentachlorophenol in mammals. J. Agric. Chem. Soc. Japan 44 (3), 124–129 (1970) (In Japanese)

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Correspondence to Ulf G. Ahlborg.

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Ahlborg, U.G., Manzoor, E. & Thunberg, T. Inhibition of β-glucuronidase by chlorinated hydroquinones and benzoquinones. Arch Toxicol 37, 81–87 (1977). https://doi.org/10.1007/BF00293856

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Key words

  • β-Glucuronidase
  • Inhibition
  • Chlorobenzoquinones
  • Chlorohydroquinones