Biotransformations of putative phytoecdysteroid biosynthetic precursors in tissue cultures of Polypodium vulgare

European Journal of Biochemistry

Volumn 266, Issue 2, 1999, Pages 608-615

  Reixach, Natàlia ^a   Lafont, René ^b   Camps, Francisco ^a   Casas, Josefina ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

20 hydroxyecdysone; Fern; Hydroxycholesterol derivatives; In vitro cultures; Induction

Indexed keywords

ECDYSTEROID; ECDYSTERONE; OXYGENASE; PLANT EXTRACT; PONASTERONE A; 2,25 DIDEOXYECDYSONE; 2,25-DIDEOXYECDYSONE; 25 DEOXYECDYSONE; 25-DEOXYECDYSONE; CHOLESTEROL DERIVATIVE; DRUG DERIVATIVE; ECDYSONE; STEROID;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; HYDROXYLATION; PLANT; PRIORITY JOURNAL; STEROID METABOLISM; CHEMICAL MODEL; CHEMISTRY; METABOLISM; POLYPODIUM; PROTEIN BINDING; TEMPERATURE; TIME;

POLYPODIUM VULGARE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ECDYSONE; ECDYSTEROIDS; ECDYSTERONE; HYDROLYSIS; HYDROXYCHOLESTEROLS; MODELS, CHEMICAL; POLYPODIUM; PROTEIN BINDING; STEROIDS; TEMPERATURE; TIME FACTORS;

EID: 1842787903     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1999.00905.x     Document Type: Article

References (41)

1. 1. Bergamasco, R. & Horn, D.H.S. (1983) Distribution and role of insect hormones in plants. In Invertebrate Endocrinology, Vol. 1, Endocrinology of Insects (Downer, R.G.H. & Laufer, H., eds), pp. 627-654. Liss, New York.
2. 2. Camps, F. (1991) Plant ecdysteroids and their interaction with insects. In Ecological Chemistry and Biochemistry of Plant Terpenoids (Harborne, J.B. & Tomas-Barberan, F.A., eds), pp. 331-376. Oxford Science, Oxford.
3. 3. Horn, D.H.S. & Bergamasco, R. (1985) Chemistry of ecdysteroids. In Comprehensive Insect Physiology, Biochemistry and Pharmacology, Vol. 7 (Kerkut, G.A. & Gilbert, L.I., eds), pp. 185-248. Pergamon Press, Oxford.
4. 4. Lafont, R. & Horn, D.H.S. (1989) Phytoecdysteroids: structure and occurrence. In Ecdysone: from Chemistry to Mode of Action (Koolman, J., ed.), pp. 39-64. Georg Thieme-Verlag, Stuttgart.
5. 5. Lafont, R. (1998) Phytoecdysteroids in the world flora: diversity, distribution, biosynthesis and evolution. Russian J. Plant Physiol. 45, 326-346.
6. 6. Lafont, R., Bouthier, A. & Wilson, I.D. (1991). Phytoecdysteroids: structures, occurrence, biosynthesis and possible ecological significance. In Insect Chemical Ecology (Hardy, I., ed.), pp. 197-214. Academia Praha and SBP Academic Publishers, Praha.
7. 3H]cholesterol in Taxus baccata. Phytochemistry 12, 569-572.
8. 8. Nagakari, M., Kushiro, T., Matsumoto, T., Tanaka, N., Kakinuma, K. & Fujimoto, Y. (1994) Incorporation of acetate and cholesterol into 20-hydroxyecdysone by hairy root clone of Ajuga reptans var. atropurpurea. Phytochemistry 36, 907-910.
9. 9. Adler, J.H. & Grebenok, R.J. (1995) Biosynthesis and distribution of insect-molting hormones in plants. A review. Lipids 30, 257-262.
10. 10. de Souza, N.J., Ghisalberti, E.L., Rees, H.H. & Goodwin, T.W. (1970) Studies on insect moulting hormones: Biosynthesis of ecdysone, ecdysterone and 5β-hydroxyecdysone in Polypodium vulgare. Phytochemistry 9, 1247-1252.
11. 11. Davies, T.G., Lockley, W.J.S., Boid, R., Rees, H.H. & Goodwin, T.W. (1980) Mechanism of formation of the A/B cis ring junction of ecdysteroids in Polypodium vulgare. Biochem. J. 190, 537-544.
12. 12. Nagakari, M., Kushiro, T., Yagi, T., Tanaka, N., Matsumoto, T., Kakinuma, K. & Fujimoto, Y. (1994) 3β-Hydroxy-5β-cholest-7-en-6-one as an intermediate of 20-hydroxyecdysone biosynthesis in a hairy root culture of Ajuga reptans var. atropurpurea. J. Chem. Soc. Chem. Commun., 1761-1762.
13. 13. Sipahimalani, A.T., Banerji, A. & Chadha, M.S. (1972) Biosynthesis and interconversion of phytoecdysones in Sesuvium portulacastrum L. J. Chem. Soc. Chem. Commun., 692-693.
14. 14. Grebenok, R.J. & Adler, J.H. (1993) Ecdysteroid biosynthesis during the ontogeny of spinach leaves. Phytochemistry 33, 341-347.
15. 15. Grebenok, R.J., Venkatachari, S. & Adler, J.H. (1994) Biosynthesis of ecdysone and ecdysone phosphates in spinach. Phytochemistry 36, 1399-1408.
16. 16. Lafont, R., Koolman, J. & Rees, H. (1993) Standardized abbreviations for common ecdysteroids. Insect Biochem. Mol. Biol. 23, 207-209.
17. 17. Tomita, Y. & Sakurai, E. (1974) Biosynthesis of phytoecdysone: incorporation of 2β,3β, I4α-trihydroxy-5β-cholest-7-en-6-one into β-ecdysone and inokosterone in Achyranthes fauriei. J. Chem. Soc. Chem. Commun., 434-435.
18. 18. Rees, H.H. (1995) Ecdysteroid biosynthesis and metabolism in relation to function. Eur. J. Entomol. 92, 9-39.
19. 19. Camps, F., Claveria, E., Coll, J., Marco, M.P., Messeguer, J. & Melé, E. (1990) Ecdysteroid production in tissue cultures of Polypodium vulgare. Phytochemistry 29, 3819-3821.
20. 20. Coll, J., Reixach, N., Sanchez-Baeza, F., Casas, J. & Camps, F. (1994) New ecdysteroids from Polypodium vulgare. Tetrahedron 50, 7247-7252.
21. 21. Reixach, N., Irurre-Santilari, J., Casas, J., Melé, E., Messeguer, J. & Camps, F. (1996) Biosynthesis of ecdysteroids in in vitro prothalli cultures of Polypodium vulgare. Phytochemistry 43, 597-602.
22. 22. Reixach, N., Irurre-Santilari, J., Camps, F., Melé, E., Messeguer, J. & Casas, J. (1997) Phytoecdysteroid overproduction in Polypodium vulgare prothalli. Phytochemistry 46, 1183-1187.
23. 23. Messeguer, J., Melé, E., Reixach, N., Irurre-Santilari, J. & Casas, J. (1998) Polypodium vulgare L. (Wood Fern): in vitro culture and the production of phytoecdysteroids. In Biotechnology in Agriculture and Forestry, Vol. 41, Medicinal and Aromatic Plants X (Bajaj, Y.P.S., ed.), pp. 333-348. Springer-Verlag, Berlin.
24. 24. Böcking, D., Dauphin-Villemant, C., Sedlmeier, D., Blais, C. & Lafont, R. (1993) Ecdysteroid biosynthesis in molting glands of the crayfish Orconectes limosus: evidence for the synthesis of 3-dehydroecdysone by in vitro synthesis and conversion studies. Insect Biochem. Mol. Biol. 23, 57-63.
25. 25. Böcking, D., Dauphin-Villemant, C., Toullec, J.Y., Blais, C. & Lafont, R. (1994) Ecdysteroid formation from 25-hydroxycholesterol by arthropod molting glands in vitro. C.R. Acad. Sci. Paris, Sér. III 317, 891-898.
26. 4 intermediates in ecdysteroid biosynthesis. Biochem. J. 320, 413-419.
27. 27. Dinan, L. & Rees, H.H. (1978) Preparation of 3-epi-ecdysone and 3-epi-20-hydroxyecdysone. Steroids 32, 629-638.
28. 28. Milner, N.P. & Rees, H.H. (1985) Involvement of 3-dehydroecdysone in the 3-epimerization of ecdysone. Biochem. J. 231, 369-374.
29. 29. Grieneisen, M.L. (1994) Recent advances in our knowledge of ecdysteroid biosynthesis in insects and crustaceans. Insect Biochem. Mol. Biol. 24, 115-132.
30. 30. Clouse, S.D. & Sasse, J.M. (1998) Brassinosteroids: Essential regulators of plant growth and development. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49, 427-451.
31. 31. Kreis, W., Hensel, A. & Stuhlemmer, U. (1998) Cardenolide biosynthesis in foxglove. Planta Med. 64, 491-499.
32. 32. Hai, T., Schneider, B., Porzel, A. & Adam, G. (1996) Metabolism of 24-epi-castasterone in cell suspension cultures of Lycopersicon esculentum. Phytochemistry 41, 197-201.
33. 33. Lafont, R. & Wilson, I.D. (1996). The Ecdysone Handbook. 2nd edn. The Chromatographic Society Press, Nottingham.
34. 34. Jizba, J., Dolejs, L., Herout, V. & Sorm, F. (1971) The structure of osladin - the sweet principle of the rhizomes of Polypodium vulgare L. Tetrahedron Lett. 18, 1329-1332.
35. 35. Jizba, J., Dolejs, L., Herout, V., Sorm, F., Fehlhaber, H.W., Snatzke, G., Tschesche, R. & Wulff, G. (1971) Polypodosaponin, ein Saponintyp aus Polypodium vulgare L. Chem. Ber. 104, 837-846.
36. 36. Dauphin-Villemant, C., Böcking, D., Blais, C., Toullec, J.-Y. & Lafont, R. (1997) Involvement of a 3β-hydroxysteroid dehydrogenase activity in ecdysteroid biosynthesis. Mol. Cell. Endocrinol. 128, 139-149.
37. 37. Li, J., Nagpal, P., Vitart, V., McMorris, T.C. & Chory, J. (1996) A role for brassinosteroids in light-dependent development of Arabidopsis. Science 272, 398-401.
38. 38. Grebenok, R.J., Galbraith, D.W., Benveniste, I. & Feyereisen, R. (1996) Ecdysone 20-monooxygenase, a cytochrome P450 enzyme from spinach, Spinacia oleracea. Phytochemistry 42, 927-933.
39. 39. Corio-Costet, M.-F., Chapuis, L. & Delbecque, J.-P. (1996) Serratula tinctoria L. (Dyer's Savory): in vitro culture and the production of ecdysteroids and other secondary metabolites. In Biotechnology in Agriculture and Forestry, Vol. 37, Medicinal and Aromatic Plants IX (Bajaj, Y.P.S., ed.), pp. 384-401. Springer-Verlag, Berlin.
40. 40. Matsumoto, T. & Tanaka, N. (1991) Production of phytoecdysteroids by hairy root cultures of Ajuga reptans var. atropurpurea. Agric. Biol. Chem. Tokyo 55, 1019-1025.
41. 41. Tomás, J., Camps, F., Coll, J., Melé, E. & Messeguer, J. (1993) Phytoecdysteroid production by Ajuga reptans tissue cultures. Phytochemistry 32, 317-324.