26-Hydroxylation of ecdysteroids is catalyzed by a typical cytochrome P-450-dependent oxidase and related to ecdysteroid resistance in an insect cell line

European Journal of Biochemistry

Volumn 248, Issue 3, 1997, Pages 707-716

  Kayser, Hartmut ^a   Winkler, Tammo ^a   Spindler Barth, Margarethe ^b  

^a NOVARTIS PHARMA AG   (Switzerland)

^b HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

26 Hydroxylase; Cytochrome P 450; Insect; Resistance; Steroid hormone

Indexed keywords

CYTOCHROME P450; ECDYSTEROID; ECDYSTERONE;

ANIMAL CELL; ARTICLE; CELL LINE; CONTROLLED STUDY; DRUG METABOLISM; DRUG RESISTANCE; ENZYME ACTIVITY; EPITHELIUM CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INSECT; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

ANIMALIA; CHIRONOMUS TENTANS; DIPTERA; INSECTA;

EID: 0030804224     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00707.x     Document Type: Article

References (42)

1. Beydon, P., Girault, J. P. & Lafont, R. (1987) Ecdysone metabolism in Pieris brassicae during the feeding last larval instar, Arch. Insect Biochem. Physiol. 4, 139-149.
2. Beydon, P., Permana, A.-D., Colardeau, J., Morinière, M. & Lafont, R. (1989) Ecdysteroids from developing eggs of Pieris brassicae, Arch. Insect Biochem. Physiol. 11, 1-11.
3. Chen, J.-H., Kabbouh, M., Fisher, M. J. & Rees, H. H. (1994) Induction of an inactivation pathway for ecdysteroids in larvae of the cotton leafworm, Spodoptera littoralis, Biochem. J. 301, 89-95.
4. Dinan, L., Spindler-Barth, M. & Spindler, K.-D. (1990) Insect cell lines as tools for studying ecdysteroid action, Invert. Reprod. Dev. 18, 43-53.
5. Feyereisen, R. & Durst, F. (1978) Ecdysterone biosynthesis: a microsomal cytochrome-P-450-linked ecdysone 20-monooxygenase from tissues of the african migratory locust, Eur J. Biochem. 88, 37-47.
6. Galbraith, M. N. & Horn, D. H. S. (1969) Insect moulting hormones: crustecdysone (20-hydroxyecdysone) from Podocarpus elatus, Aust. J. Chem. 22, 1045-1057.
7. Galbraith, M. N., Horn, D. H. S., Middleton, E. J., Kaplanis, J. N. & Thompson, M. J. (1973) Structure of podecdysone C, a steroid with moulting hormone activity from the bark of Podocamus elatus, R. Br., Experientia (Basel) 29, 782.
8. Gelman, D. B., Woods, C. W. & Borkovec, A. J. (1988) Ecdysteroid profiles for hemolymph and testes from larvae, pupae, and pharate adults of the European corn borer, Ostrinia nubilalis Hubner, Arch. Insect Biochem. Physiol. 7, 267-279.
9. 3H]-ecdysone in Schistocerca gregaria: formation of ecdysteroid acids together with free and phosphorylated ecdysteroid acetates, Arch. Insect Biochem. Physiol. 1, 385-407.
10. 1H-NMR assignment of ecdysone and 20-hydroxyecdysone, J. Insect Physiol. 34, 701-706.
11. Grau, V. & Lafont, R. (1994) Metabolism of ecdysone and 20-hydroxyecdysone in adult Drosophila melanogaster, Insect Biochem. Mol. Biol. 24, 49-58.
12. Grieneisen, M. L. (1994) Recent advances in our knowledge of ecdysteroid biosynthesis in insects and crustaceans, Insect Biochem. Mol. Biol. 24, 115-132.
13. Guengerich, F. P. (1991) Reactions and significance of cytochrome P-450 enzymes, J. Biol. Chem. 266, 10019-10022.
14. Halliday, W. R., Farnsworth, D. E. & Feyereisen, R. (1986) Hemolymph ecdysteroid titer and midgut ecdysone 20-monooxygenase activity during the last larval stage of Diploptera punctata, Insect. Biochem. 16, 627-634.
15. Henrich, V. C. & Brown, N. E. (1995) Insect nuclear receptors: a developmental and comparative perspective, Insect Biochem. Mol. Biol. 25, 881-897.
16. Koolman, J. & Karlson, P. (1985) Regulation of ecdysteroid titer:degradation, in Comprehensive insect physiology, biochemistry and pharmacology (Kerkut, G. A. & Gilbert, L. I., eds) vol. 7, pp. 343-361, Pergamon Press, Oxford.
17. Lafont, R., Beydon, P., Sommé-Martin, G. & Blais, C. (1980) High-performance liquid chromatography of ecdysone metabolites applied to the cabbage butterfly, Pieris brassicae L., Steroids 36, 185-206.
18. Lafont, R., Blais, C., Beydon, P., Modde, J.-F., Enderle, U. & Koolman, J. (1983) Conversion of ecdysone and 20-hydroxyecdysone into 26-oic derivatives is a major pathway in larvae and pupae of species from three insect orders, Arch. Insect Biochem. Physiol. 1, 41-58.
19. Lafont, R. & Wilson, I. D. (1996) The ecdysone handbook, 2nd edn. The Chromatographic Society, Nottingham, UK.
20. Lambert, J. B. & Vagenas, A. R. (1981) Dependence of the γ carbon-13 shielding effect on the dihedral angle, Org. Magn. Reson. 17, 265-269.
21. Loeb, M. J. & Woods, C. W. (1989) Metabolism of ecdysteroids by testes of the tobacco budworm, Heliothis virescens, Arch. Insect Biochem. Physiol. 10, 83-92.
22. 14C]cholesterol in Manduca sexta pupae: isolation and identification of sterol sulfates, free ecdysteroids, and ecdysteroid acids, Arch. Insect Biochem. Physiol. 7, 249-266.
23. Ludwig, M., Spindler-Barth, M. & Spindler, K.-D. (1991) Properties of chitin synthase in homogenates from Chironomus cells, Arch. Insect Biochem. Physiol. 18, 251-263.
24. Mori, H., Tsuneda, K., Shibata, K. & Sawai, M. (1967) Synthesis of ecdysone. II. Synthesis of and stereochemistry of 2β,3β-dihydroxycholestan-6-ones and their derivatives, Pharm. Bull. 15, 466-473.
25. Omura, T. & Sato, R. (1964) The carbon monoxide-bindung pigment of liver microsomes - I. Evidence for its hemoprotein nature, J. Biol. Chem. 239, 2370-2378.
26. Rees, H. H. (1995) Ecdysteroid biosynthesis and inactivation in relation to function, Eur J. Entomol. 92, 9-39.
27. Robinson, P. L., Barry, C. N., Kelly, J. W. & Evans, S. A. Jr (1985) Diethoxytriphenylphosphorane: a mild, regioselective cyclodehydrating reagent for conversion of diols to cyclic ethers, Stereochemistry, synthetic utility, and scope, J. Am. Chem. Soc. 107, 5210-5219.
28. Rodrigues, A. D., Gibson, G. G., Ioannides, C. & Parke, D. V. (1987) Interactions of imidazole antifungal agents with purified cytochrome P-450 proteins, Biochem. Pharmacol. 36, 4277-4281.
29. Schenkman, J. B. & Jansson, I. (1995) Introduction to cytochrome P-450, NATO ASI (Adv. Sci. Inst.) Ser. Ser. H Cell Biol. 90, 1-19.
30. Sheets, J. J., Mason, J. I., Wise, C. A. & Estabrook, R. W. (1986) Inhibition of rat liver microsomal cytochrome P-450 steroid hydroxylase reactions by imidazole antimycotic agents, Biochem. Pharmacol. 35, 487-491.
31. Sommé-Martin, G., Colardeau, J., Beydon, P., Blais, C., Lepesant, J. A. & Lafont, R. (1990) P1 gene expression in Drosophila larval fat body: induction by various ecdysteroids, Arch. Insect Biochem. Physiol. 15, 43-56.
32. Sommé-Martin, G., Lafont, R., Colardeau, J., Coudouël, N., Oberlander, H. & Porcheron, P. (1992) Uptake and metabolism of ecdysone and 20-hydroxyecdysone in an lepidopteran cell line derived from wing discs of Plodia interpunctella, Insect Biochem. Mol. Biol. 22, 137-141.
33. Spindler, K.-D. & Spindler-Barth, M. (1991) Ecdysteroid production and metabolism by an epithelial cell line from Chironomus tentans, Naturwissenschaften 78, 78-79.
34. Spindler-Barth, M. & Spindler, K.-D. (1997) Ecdysteroid resistant subclones of the epithelial cell line from Chironomus tentans (Insecta, Diptera). I. Selection and characterization of resistant clones, In Vitro Cell Dev. Biol. Anim., in the press.
35. 14C]cholesterol, Arch. Insect Biochem. 7, 157-172.
36. Ward, G. B., Beydon, P., Lafont, R. & Mayer, R. T. (1990) Metabolism of ecdysteroids by a chitin-synthesizing insect cell line, Arch. Insect Biochem. Physiol. 15, 137-148.
37. Warren, J. T., Steiner, B., Dorn, A., Pak, M. & Gilbert, L. I. (1986) Metabolism of ecdysteroids during the embryogenesis of Manduca sexta, J. Liq. Chromatogr. 9, 1759-1782.
38. Weirich, G. F. & Adams, J. R. (1984) Microsomal marker enzymes of Manduca sexta (L.) midgut, Arch. Insect Biochem. Physiol. 1, 311-321.
39. Wikvall, K. (1993) Sterol 26-hydroxylase, Handb. Exp. Pharmacol. 105, 705-718.
40. 3 metabolites, Helv. Chim. Acta 63, 1609-1614.
41. Wyss, C. (1982) Chironomus tentans epithelial cell lines sensitive to ecdysteroid, juvenile hormones, insulin and heat shock, Exp. Cell Res. 139, 309-319.
42. HDM purified from Saccharomyces cerevisiae microsomes, Biochem. Pharmacol. 36, 229-235.