Effect of the dietary brominated phenol, lanasol, on chemical biotransformation enzymes in the gumboot chiton Cryptochiton stelleri (Middendorf, 1846)

Comparative Biochemistry and Physiology - C Pharmacology Toxicology and Endocrinology

Volumn 127, Issue 2, 2000, Pages 133-142

  Debusk, Bryan C ^a   Chimote, Shukrit S ^a   Rimoldi, John M ^a   Schenk, Dan ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Cytochrome P450; ECOD; GST; Steroid hydroxylase; Sulfotransferase; UDPGT

Indexed keywords

BROMINE DERIVATIVE; CYTOCHROME P450 3A; CYTOCHROME P450 CYP1A; CYTOCHROME P450 CYP2; CYTOCHROME P450 ISOENZYME; ESTRADIOL; GLUCURONOSYLTRANSFERASE; LANASOL; OXYGENASE; PHENOL DERIVATIVE; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONJUGATION; DIETARY INTAKE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; HOST RESISTANCE; MOLLUSC; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ADMINISTRATION, ORAL; ANIMAL; BIOTRANSFORMATION; CATECHOLS; CYTOCHROME P-450 ENZYME SYSTEM; DIET; DINITROCHLOROBENZENE; ENZYME INHIBITORS; ESTRADIOL DEHYDROGENASES; EXOCRINE GLANDS; GLUCURONOSYLTRANSFERASE; GLUTATHIONE TRANSFERASE; ISOENZYMES; MICROSOMES; MOLLUSCA; SULFOTRANSFERASES;

CRYPTOCHITON STELLERI; ODONTHALIA DENTATA;

EID: 0033829769     PISSN: 07428413     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0742-8413(00)00141-9     Document Type: Article

References (40)

1. Beckman J.D. Continuous fluorometric assay of phenol sulfotransferase. Anal. Biochem. 197:1991;408-411.
2. Black, S.D., Coon, M.J., 1986. Comparative structures of P-450 cytochromes. In: Monetellano Prod (Ed.), Cytochrome P-450: Structure, Mechanism, and Biochemistry. Plenum, New York.
3. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
4. Carlson D.J. Fine-scale variability of lanosol and its disulfate ester in the temperate red alga Neorhodomela larix. J. Chem. Ecol. 15(4):1987;1321-1333.
5. Das M., Bickers D.R., Mukhtar H. Plant phenols as invitro inhibitors of gluathione S-transferase(s). Biochem. Biophys. Res. Commun. 120:1984;427-433.
6. Dierckx P.J. Glutathione S-transferase in aquatic macroinvertebrates and its interaction with different organic micropollutants. Sci. Total Envir. 40:1984;93-102.
7. Fenical W. Halogenation in the Rhodophyta: a review. J. Phycol. 11:1975;245-259.
8. Ford P.W., Narbut M.R., Belli J., Davidson B.S. Synthesis and structural properties of the benzotathiepins varacin and isolissoclinotoxin A. J.Org. Chem. 59:1984;5955-5960.
9. Gonzalez F.J. The molecular biology of cytochrome P450s. Pharm. Rev. 40:1989;243-288.
10. Habig W.H., Pabst M.J., Jakoby W.B. Glutathione S-transferases: The first enzymatic step in mercapturic acid formation. J. Biol. Chem. 249:1974;7130-7139.
11. Hay, M.E., Steinberg, P.D., 1992. The chemical ecology of plant-herbivore interactions in marine versus terrestrial communities. In: Rosenthal, G.A., Berenbaum, M.R. (Eds.), Herbivores: Their Interactions with Secondary Plant Metabolites, vol. II. Academic Press, San Diego, CA, pp. 371-413.
12. James M.O. Conjugation of organic pollutants in aquatic species. Envir. Health Persp. 71:1987;97-103.
13. James M.O. Cytochrome P450 monooxygenases in crustaceans. Xenobiotica. 19:1989;1063-1076.
14. James, M.O., Fouts J.R., Bend J.R., 1974. Xenobiotic metabolizing enzymes in marine fish. In: Kahn, M.A. (Ed.), Pesticides in the Aquatic Environment. Plenum, New York.
15. Katsui, N., Suzuki, Y., Kitamura, S., Irie, T., 1967. 5,6-Dibromoprotocatechualdehyde and 2,3-dibromo-4,5-dihydroxybenzyl methyl ether. Tetrahedron 1185-1188.
16. Kurata K., Taniguchii K. Feeding-deterrent bromophenols from Odonthalia corymbifera. Phytochemistry. 45(3):1997;485-487.
17. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227:1970;680-685.
18. Livingstone, D.R., 1991. Organic xenobiotic metabolism in marine invertebrates. In: Giles, R. (Ed.), Advances in Comparitive Environmental Physiology. Springer-Verlag, Berlin, pp. 46-185.
19. Lundgren L., Olsson K., Theander O. Synthesis of some bromophenols present in red algae. Acta. Chem. Scand. B33:1979;105-108.
20. Miranda C.L., Wang J.L. Purification and characterization of hepatic steroid hydroxylases from untreated rainbow trout. Arch. Biochem. Biophys. 268:1989;227-238.
21. Miranda C.L., Yang Y.H. Comparison of rainbow trout and mammalian cytochrome P450 enzymes; evidence for structural similarity between trout P450 LMC5 and human P450IIIA4. Biochem. Biophys. Res. Commun. 176:1991;558-563.
22. Morcillo Y., Ronis M.J.J. Effects of tributyltin on the cytochrome P-450 monooxygenase system and sex steroid metabolism in the clam Ruditapes decussata. Mar. Envir. Res. 46(1):1998;583-586.
23. Oberdorster E., Rittschof D. Induction of cytochrome P450 3A and heat shock protein by tributyltin in blue crab, Callinectes sapidus. Aquat. Toxicol. 41:1998;83-100.
24. Paul, V.J., 1992. Ecological Roles of Marine Natural Products. Cornell University Press, Ithaca, NY.
25. Pawlik J.R., Chanas B., Toonen R.J., Fenical W. Defenses of Caribbean sponges against predatory reef fish: I. Chemical deterrency. Mar. Ecol. Prog. Ser. 127:1995;183-194.
26. Pedersen M., Saenger P., Fries L. Simple brominated phenols in red algae. Phytologia. 13:1974;2273-2279.
27. Perkins, E.J., DeBusk, B.C., Schlenk, D., 2000 (submitted). Isolation of a novel hepatic CYP2-related protein from channel catfish, Ictalurus Punctatus. Arch. Biochem. Biophys.
28. Phillips D.W., Towers G.H.N. Chemical ecology of red algal bromophenols. I. Temporal, interpopulational and within-thallus measurements of lanosol levels in Rhodomela larix (Turner) C. Agardh. J. Exp. Mar. Biol. Ecol. 58(2-3):1982;285-293.
29. Phillips D.W., Towers G.H.N. Chemical ecology of red algal bromophenols. II. Exudation of bromophenols by Rhodomela larix (Turner) C. Agardh. J. Exp. Mar. Biol. Ecol. 58(2-3):1982;295-302.
30. Prough R.A., Burke M.D., Mayer R.T. Direct fluorometric methods for measuring mixed-function oxidase activity. Methods Enzymol. 52:1978;372-377.
31. Sato, R., Omura, T., 1978. Cytochrome P-450. Academic Press, New York.
32. Schlenk D., Buhler D.R. Cytochrome P-450 and phase II activities in the gumboot chiton Cryptochiton stelleri. Aquat. Toxicol. 13:1988;167-182.
33. Schlenk D., Buhler D.R. Determination of multiple forms of cytochrome P-450 in microsomes from the digestive gland of Cryptochiton stelleri. Biochem. Biophys. Res. Commun. 163:1989;476-480.
34. Schlenk D., Buhler D.R. Role of flavin-containing monooxygenase in the in vitro biotransformation of aldicarb in rainbow trout (Oncorhynchus mykiss). Xenobiotica. 21:1991;1583-1589.
35. Schuler M.A. The role of cytochrome P450 monooxygenases in plant-insect interactions. Plant Physiol. 112:1996;1411-1419.
36. Sudalai A., Krishna R.G.S. Synthesis of some hydroxymethylbromophenols of marine origin. Ind. J. Chem. 28B:1989;858-859.
37. Towbin, H., Staehelin, T., Gordon, J., 1979. Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc. Natl. Acad. Sci. USA.
38. Vrolijk, N.H., Targett, N.M., 1991. Cytochrome P450 and glutathione transferase GST activity in Cyphoma gibosum. Evidence for detoxification of gorgonian allelochemicals. Annual Meeting of the American Society of Zoologists, American Microscopical Society, Animal Behavior Society, the Crustacean Society, and the International Association of Astacology, Atlanta, GA.
39. Yates, K.R., 1989. The feeding ecology of the gumboot chiton, Cryptochiton stelleri (Middendorff, 1846). Zoology. Oregon State University, Corvallis.
40. Zhang K., Das N.P. Inhibitory effects of plant polyphenols on rat liver glutathione S-transferases. Biochem. Pharm. 47:1994;2063-2068.