Ecdysone biosynthesis: Pathways, enzymes, and the early steps problem

References

• Aldrich , J. R. , Kelly , T. J. and Woods , C. W. 1982 . Larval moulting hormone of trichophoran Hemiptera Heteroptera: makisterone A, not 20-hydroxyecdysone . J. Insect Physiol. , 28 : 857 – 861 .
   Google Scholar
• Bergamasco , R. and Horn , D. H.S. 1981 . “ The biological activities of ecdysteroids and ecdysteroids analogues. ” . In Progress in Ecdysone Research Edited by: Hoffmann , J. A. 299 – 324 . Noth Holland : Elsevier .
   Google Scholar
• Beydon , P. , Permana , A.-D. , Colardeau , J. , Morinière , M. and Lafont , R. 1989 . Ecdysteroids from developing eggs of Pieris brassicae . Arch. Insect Biochem. Physiol. , 11 : 1 – 11 .
   Google Scholar
• Blais , C. and Lafont , R. 1984 . Ecdysteroid metabolism by soluble enzymes from an insect. Metabolic relationships between 3β-hydroxy-, 3α-hydroxy- and 3-oxo-ecdysteroids . Hoppe-Seyler's Z. Physiol. Chem. , 365 : 809 – 817 .
   PubMedGoogle Scholar
• Bollenbacher , W. E. , Galbraith , M. N. , Gilbert , L. I. and Horn , D. H.S. 1977 . In vitro metabolism of 3β-hydroxy-, and 3β, 14α-dihydroxy-[3α3H]-5β-cholest-7-en-6-one by the prothoracic glands of Manduca sexta . Steroids , 29 : 47 – 63 .
   PubMed Web of Science ®Google Scholar
• Bordes-Alléaume , N. and Sami , L. 1987 . Ecdysteroid titres and cuticle deposition in embryos of the dipteran Calliphora erythrocephala . Int. J. Invertebr. Reprod. Dev. , 11 : 109
   Google Scholar
• Clarke , G. S. 1981 . PhD. Thesis, University of Liverpool, U.K
   Google Scholar
• Clayton , R. B. 1964 . The utilization of sterols by insects . J. Lipid Res. , 5 : 3 – 19 .
   PubMed Web of Science ®Google Scholar
• Cook , I. F. , Lloyd-Jones , J. G. , Rees , H. H. and Goodwin , T. W. 1973 . The stereochemistry of hydrogen elimination from C-7 during the biosynthesis of ecdysones in insects and plants . Biochem. J. , 136 : 135 – 145 .
   PubMedGoogle Scholar
• Davies , T. G. , Dinan , L. N. , Lockley , W. J.S. , Rees , H. H. and Goodwin , T. W. 1981 . Mechanism of formation of the A/B cis ring junction of ecdysteroids in the locust, Schistocerca gregaria . Biochem. J. , 194 : 53 – 62 .
   PubMed Web of Science ®Google Scholar
• Delbecque , J. P. , Meister , M. F. and Quennedey , A. 1986 . Conversion of radiolabelled 2,22,25-trideoxyecdysone in Tenebrio pupae . Insect Biochem. , 16 : 57 – 63 .
   Google Scholar
• Espig , W. , Thiry , E. and Hoffmann , K. H. 1989 . Ecdysteroids during ovarian development and embryogenesis in the cricket, Gryllus bimaculatus de Geer . Invert. Reprod. Dev. , 15 : 143 – 154 .
   Web of Science ®Google Scholar
• Faux , A. F. , Horn , D. H.S. , Kinnear , J. F. , Martin , M.-D. , Wilkie , J. S. and Willing , R. I. 1979 . Evaluation of 3β-hydroxy-5β-cholest-7-en-6-one and related steroids as precursors of ecdysteroids in Calliphora stygia . Insect Biochem. , 9 : 101 – 105 .
   Google Scholar
• Feldlaufer , M. F. , Herbert , E. W. , Svoboda , J. A. and Thompson , M. J. 1986a . Biosynthesis of makisterone A and 20-hydroxyecdysone from labeled sterols by the honey bee. Apis mellifera . Arch. Insect Biochem. Physiol. , 3 : 415 – 421 .
   Web of Science ®Google Scholar
• Feldlaufer , M. F. , Svoboda , J. A. and Herbert , E. W. Jr . 1986b . Makisterone A and 24-methylenecholesterol from the ovaries of the honey bee, Apis mellifera L. . Experientia , 42 : 200 – 201 .
   Google Scholar
• Feldlaufer , M. F. , Svoboda , J. A. , Aldrich , J. R. and Lusby , W. R. 1986c . The neutral sterols of Megalotomus quinquespinous (Say) (Hemiptera: Alydidae) and identification of makisterone A as the major free ecdysteroid. . Arch. Insect Biochem. Physiol. , 3 : 423 – 430 .
   Google Scholar
• Feldlaufer , M. F. , Weirich , G. F. , Svoboda , J. A. and Lusby , W. R. 1990 . Molting hormones in the developing embryos of the cotton stainer bug Dysdercus fasciatus, Presented at the IXth Ecdysone Workshop, Paris . Invert. Reprod. Devel. , 18 : 1 – 2 . 112
   Google Scholar
• Fournier , B. and Radallah , D. 1988 . Ecdysteroids in Carausius eggs during embryonic development. . Arch. Insect Biochem. Physiol. , 7 : 211 – 224 .
   Web of Science ®Google Scholar
• Galbraith , M. N. , Horn , D. H.S. , Middleton , E. J. and Thompson , J. A. 1972 . Side chain hydroxylation in the biosynthesis of β-ecdysone (20-hydroxyecdysone) in the blowfly Calliphora stygia . Experientia , 28 : 264
   Google Scholar
• Gelman , D. B. , Thyagaraja , B. S. , Kelly , T. J. , Masler , E. P. , Bell , R. A. and Borkovec , A. B. 1990 . Ecdysiotropic factors in proctodaea of the european corn borer, Ostrinia nubilalis (Hubner) and the gypsy moth, Lymantria dispar. Presented at the IXth Ecdysone Workshop, Paris . Invert. Reprod. Devel. , 18 : 1 – 2 . 112
   Google Scholar
• Gibson , J. M. , Majunder , M. S.I. , Mendis , A. H.W. and Rees , H. H. 1983 . Absence of phytosterol dealkylation and identification of the major ecdysteroid as makisterone A in Dysdercus fasciatus (Heteroptera, Pyrrhocoridae) . Arch. Insect Biochem. Physiol. , 1 : 105 – 120 .
   Google Scholar
• Goodwin , T. W. and Mercer , E. I. 1983 . Introduction to Plant Biochemistry London : Pergamon .
   Google Scholar
• Greenwood , D. R. and Rees , H. H. 1982 . Mechanism of hydroxylation at C-22 during the biosynthesis of ecdysteroids in the locust, Schistocerca gregaria . Biochem. J. , 208 : 857 – 864 .
   PubMedGoogle Scholar
• Greenwood , D. R. , Dinan , L. N. and Rees , H. H. 1982 . Mechanism of hydroxylation at C-2 during the biosynthesis of ecdysone in the ovaries of the locust, Schistocerca gregaria . Biochem. J. , 217 : 783 – 789 .
   Google Scholar
• Haag , T. , Hétru , C. , Nakatani , Y. , Luu , B. , Pichat , L. , Audinot , M. and Meister , M.-F. 1985 . Synthesis of labelled ecdysone precursor: Part I. Tritiated labelled [3H4-22,23,24,25]-3β, 14α-dihydroxy-5β-cholest-7-en-6-one . J. Labelled Comp. Radiopharm. , 22 : 547 – 557 .
   Web of Science ®Google Scholar
• Haag , T. , Meister , M. F. , Hétru , C. , Kappler , C. , Nakatanl , Y. , Beaucourt , J.-P. , Rousseau , B. and Luu , B. 1987 . Synthesis of a labelled putative precursor of ecdysone—II, [3H4]3β-hydroxy-5β-cholest-7-en-6-one: critical reevaluation of its role in Locusta migratoria . Insect Biochem. , 17 : 291 – 301 .
   Google Scholar
• Haag , T. , Hétru , C. , Kappler , C. , Moustier , A. M. , Hoffmann , J. A. and Luu , B. 1988 . Study of the biosynthesis of ecdysone. Part IV: synthesis of high specific activity (3H4-22,23)-2,22-dideoxyecdyosne. Tissue distribution of the C-22 hydroxylase in Locusta migratoria . Tetrahedron , 44 : 1397 – 1408 .
   Web of Science ®Google Scholar
• Hétru , C. , Kappler , C. , Hoffmann , J. A. , Nearn , R. , Luu , B. and Horn , D. H.S. 1982 . The biosynthetic pathway of ecdysone: studies with vitellogenic ovaries of Locusta migratoria (Orthoptera) . Mol. Cell. Endocrinol. , 26 : 51 – 81 .
   PubMed Web of Science ®Google Scholar
• Hétru , C. , Nakatani , Y. , Luu , B. and Hoffmann , J. A. 1983 . Synthesis of high specific activity (23,24)-3H4-2-deoxyecdysone . Nouv. J. Chim. , 7 : 587 – 591 .
   Google Scholar
• Hétru , C. , Dollé , F. , Kappler , C. , Luu , B. and Hoffmann , J. A. 1990 . Synthesis of high specific activity tritiated 7-dehydrocholesterol and conversion studies in Locusta migratoria, Presented at the IXth Ecdysone Workshop . Paris, Invert. Reprod. Devel. , 18 : 1 – 2 . 117
   Google Scholar
• Horn , D. H.S. , Middleton , E. J. , Thompson , J. A. and Wilkie , J. S. 1974 . Metabolism of some possible ecdysone precursors in Calliphora stygia . J. Insect Physiol. , 20 : 2433 – 2445 .
   PubMed Web of Science ®Google Scholar
• Isaac , R. E. , Rees , H. H. and Goodwin , T. W. 1981 . Isolation of 2-deoxy-20-hydroxyecdysone and—epi-2-deoxyecdysone from eggs of the desert locust, Schistocerca gregaria, during embryogenesis . J. Chem. Soc. Chem. Commun. , : 418 – 420 .
   Google Scholar
• Johnson , P. and Rees , H. H. 1977 . Biosynthesis of ecdysone: metabolism of 7-dehydrocholesterol in Schistocerca gregaria . J. Insect Physiol. , 23 : 1387 – 1392 .
   Google Scholar
• Johnson , P. , Cook , I. F. , Rees , H. H. and Goodwin , T. W. 1975 . Mode of formation of cholesta-5, 7-dien-3β-ol from cholest-5-en-3β-ol by larvae of Calliphora erythrocephala . Biochem. J. , 152 : 303 – 311 .
   PubMed Web of Science ®Google Scholar
• Kabbouh , M. , Kappler , C. , Hétru , C. and Durst , F. 1987 . Further characterization of the 2-deoxyecdysone C-2 hydroxylase from Locusta migratoria . Insect Biochem. , 17 : 1155 – 1161 .
   Google Scholar
• Kaplanis , J. N. , Robbins , W. E. , Thompson , M. J. and Baumhover , H. H. 1969 . Ecdysone analog: conversion to alpha ecdysone and 20-hydroxyecdysone by an insect. . Science , 166 : 1540 – 1541 .
   PubMed Web of Science ®Google Scholar
• Kappler , C. , Goltzené , F. , Lagueux , M. , Hetru , C. and Hoffmann , J. A. 1986 . Role of the follicle cells and the oocytes in ecdysone biosynthesis and esterification in vitellogenic females of Locusta migratoria . J. Invert. Reprod. Dev. , 9 : 17 – 34 .
   Web of Science ®Google Scholar
• Kappler , C. , Kabbouh , M. , Hetru , C. , Durst , F. and Hoffmann , J. A. 1988 . Characterization of three hydroxylases involved in the final steps of biosynthesis of the steroid hormone ecdysone in Locusta migratoria (insecta, Orthoptera) . J. Steroid Biochem. , 31 : 891 – 898 .
   PubMedGoogle Scholar
• Karlson , P. and Hoffmeister , H. 1963 . Zur Biogenese des Ecdysons. I: Umwandlung von Cholesterin in Ecdyson . Z. Physiol. Chem. , 331 : 298 – 300 .
   Google Scholar
• Kelly , T. J. , Woods , C. W. , Redfern , R. E. and Borkovec , A. B. 1981 . Makisterone A: the moulting hormone of larval Oncopeltus? . J. Exp. Zool. , 218 : 127 – 232 .
   Google Scholar
• King , D. S. 1972a . Metabolism of α-ecdysone and possible immediate precursors by insects in vivo and in vitro . Gen. Comp. Endocrinol. Suppl. , 3 : 221 – 227 .
   Google Scholar
• King , D. S. 1972b . Ecdysone metabolism in insects . Amer. Zool. , 12 : 343 – 345 .
   Google Scholar
• Kinnear , J. F. , Martin , M.-D. , Faux , A. F. , Horn , D. H.S. and Wilkie , J. S. 1979 . Insect moulting hormones: a study of 4-en-3-one steroids as possible ecdysteroid precursors . Aust. J. Chem. , 32 : 2017 – 2024 .
   Google Scholar
• Lachaise , F. , Meister , M. F. , Hétru , C. and Lafont , R. 1986 . Studies on the biosynthesis of ecdysone by the Y-organs of Carcinus maenas . Molec. Cell. Endocrin. , 45 : 253 – 261 .
   PubMed Web of Science ®Google Scholar
• Lagueux , M. , Hoffmann , J. A. , Goltzené , F. , Kappler , C. , Tsoupras , G. , Hétru , C. and Luu , B. 1984 . “ Ecdysteroids in ovaries and embryos of Locusta ” . In Biosynthesis, metabolism and mode of action of invertebrate hormones Edited by: Hoffmann , J. A. and Porchet , M. 168 – 180 . Berlin-Heidelberg : Springer Verlag .
   Google Scholar
• Lockley , W. J.S. , Boid , R. , Lioyd-Jones , J. G. , Rees , H. H. and Goodwin , T. W. 1975 . Fate of the C-4 hydrogen atoms of cholesterol during its transformation into ecdysones in insects and plants . J. Chem. Commun. , : 346 – 348 .
   Google Scholar
• Milner , N. P. and Rees , H. H. 1985 . Involvement of 3-dehydroecdysone in the 3-epimerization of ecdysone . Biochem. J. , 231 : 369 – 374 .
   PubMed Web of Science ®Google Scholar
• Majunder , M. S.I. 1978 . PhD Thesis, University of Liverpool, U.K
   Google Scholar
• Meister , M. F. , Dimarq , J.-L. , Kappler , C. , Hétru , C. , Lagueux , M. , Lanot , R. , Luu , B. and Hoffmann , J. A. 1985 . Conversion of a radiolabellec precursor 2,22,25-tri-deoxyecdysone by embryonic and larval tissues of Locusta migratoria . Molec. Cell. Endocrinol. , 41 : 27 – 44 .
   PubMed Web of Science ®Google Scholar
• Meister , M. F. , Brandtner , H. M. , Koolman , J. and Hoffmann , J. A. 1987 . Conversion of a radiolabelled putative ecdysone precursor, 2,22,25-trideoxyecdysone (5β-ketodiol) in larvae and pupae of Calliphora vicina . Int. J. Invert. Reprod. Dev. , 12 : 13 – 28 .
   Google Scholar
• Milner , N. P. , Nali , M. , Gibson , J. M. and Rees , H. H. 1986 . Early stages of ecdysone biosynthesis: the role of 7-dehydrocholesterol . Insect Biochem. , 16 : 1723
   Google Scholar
• Morisaki , M. , Ohtaka , H. , Okubayashi , M. , Ikekawa , N. , Horie , Y. and Nakasone , S. 1972 . Fucosterol-24,28-epoxide, as a probable intermediate in the conversion of β-sitosterol to cholesterol in the silkworm . J. Chem. Soc. Commun. , : 1272
   Google Scholar
• Ohnishi , E. , Mizuno , T. , Ikekawa , N. and Ikeda , T. 1981 . Accumulation of 2-deoxy-edysteroids in ovaries of the silkworm Bombyx mori . Insect Biochem. , 11 : 155 – 159 .
   Google Scholar
• Redfern , C. P.F. 1984 . Evidence for the presence of makisterone A in Drosophila larvae and the secretion of 20-deoxymakisterone A by the ring gland . Proc. Natl. Acad. Sci. U.S.A. , 81 : 5643 – 5647 .
   PubMed Web of Science ®Google Scholar
• Redfern , C. P.F. 1986 . Changes in patterns of ecdysteroid secretion by the ring gland of Drosophila in relation to the sterol composition of the diet . Experientia , 42 : 307 – 309 .
   Google Scholar
• Rees , H. H. and Isaac , R. E. 1984 . “ Biosynthesis of ovarian ecdysteroid phosphates and their metabolic fate during embryognesis in Schistocerca gregaria ” . In Biosynthesis, metabolism and mode of action of invertebrate hormones Edited by: Hoffmann , J. A. and Porchet , M. 181 – 195 . 99 Berlin-Heidelberg : Springer Verlag .
   Google Scholar
• Rees , H. H. 1983 . “ Ecdysteroids. ” . In Biosynthesis of Isoprenoid Compounds, Vol 2 Edited by: Porter , J. W. and Spurgeon , S. L. 463 – 505 . New-York : Wiley .
   Google Scholar
• Rees , H. H. 1984 . Biosynthesis of ecdysone . Nova Acta Leopoldina , 56 : 267 – 295 .
   Google Scholar
• Rees , H. H. 1985 . “ Biosynthesis of ecdysone. ” . In Comprehensive Insect Physiology Biochemistry and Pharmacology, Vol 7 Edited by: Kerkut , G. A. and Gilbert , L. I. 249 – 293 . Oxford : Pergamon Press .
   Google Scholar
• Rees , H. H. 1989 . “ Pathways of biosynthesis of ecdysone. ” . In Ecdysone Edited by: Koolman , J. 152 – 160 . Stuttgart : Georg. Thieme Verlag .
   Google Scholar
• Robbins , W. E. , Kaplanis , J. N. , Svoboda , J. A. and Thompson , M. J. 1971 . Steroid metabolism in insects . Annu. Rev. Entomol. , 16 : 53 – 72 .
   Web of Science ®Google Scholar
• Sakurai , S. , Ikekawa , N. , Ohtaki , T. and Chino , H. 1977 . 3β-Hydroxy-5α-cholestan-6-one: a possible precursor of α-ecdysone biosynthesis . Science , 198 : 627 – 629 .
   PubMedGoogle Scholar
• Sakurai , S. , Yonemura , N. , Fujimoto , Y. , Hata , F. and Ikekawa , N. 1986 . 7-Dehydrosterols in prothoracic glands of the silkworm Bombyx mori . Experientia , 42 : 1034 – 1036 .
   Google Scholar
• Sakurai , S. , Warren , J. T. and Gilbert , L. I. 1989 . Mediation of ecdysone synthesis in Manduca sexta by a hemolymph enzyme . Arch Insect Biochem Physiol. , 10 : 179 – 197 .
   Web of Science ®Google Scholar
• Spaziani , E. , Rees , H. H. , Wang , W. L. and Watson , R. D. 1989 . Evidence that Y-organs of the crab Cancer antennarius secrete 3-dehydroecdysone . Molec. Cell. Endocrin. , 66 : 17 – 25 .
   PubMed Web of Science ®Google Scholar
• Spaziani , E. , Rees , H. H. and Wang , W. L. 1990 . Secretion and metabolism of 3-dehydroecdysone by the Y-organs of the crab, Cancer Antennarius, Presented at the IXth Ecdysone Workshop, Paris, Invert. . Reprod. Devel. , 18 : 1 – 2 . 129
   Google Scholar
• Svoboda , J. A. , Kaplanis , J. N. , Robbins , W. E. and Thompson , M. J. 1975 . Recent development in insect steroid metabolism . Annu. Rev. Entomol. , 20 : 205 – 220 .
   PubMed Web of Science ®Google Scholar
• Svoboda , J. A. , Thompson , M. J. , Robbins , W. E. and Kaplanis , J. N. 1978 . Insect steroid metabolism . Lipids , 13 : 742 – 753 .
   PubMed Web of Science ®Google Scholar
• Svoboda , J. A. , Nair , A. M.G. , Agarwal , N. , Agarwal , H. C. and Robbins , W. E. 1979 . The sterols of the khapra beetle, Trogoderma granarium Everts . Experientia , 35 : 1454 – 1455 .
   PubMedGoogle Scholar
• Svoboda , J. A. , Thompson , M. J. , Herbert , E. W. and Shimanuki , H. 1980 . Sterol utilization in honey bees fed a synthetic diet: analysis of prepupal sterols . J. Insect Physiol. , 26 : 291 – 294 .
   Web of Science ®Google Scholar
• Svoboda , J. A. , Herbert , E. W. , Lusby , W. R. and Thompson , M. J. 1983a . Comparison of sterols of pollens, honey bee workers, and prepupae from field sites. . Arch. Insect Biochem. Physiol. , 1 : 25 – 31 .
   Web of Science ®Google Scholar
• Svoboda , J. A. , Herbert , E. W. Jr and Thompson , M. J. 1983b . Definitive evidence for lack of phytosterol dealkylation in honey bees . Experientia , 39 : 1120 – 1121 .
   Google Scholar
• Thomson , J. A. , Hafferl , N. , Galbraith , M. N. , Horn , D. H.S. and Middleton , E. J. 1971 . Possible biosynthetic precursors of b-ecdysone in Calliphora stygia, J. Chem. Soc. . Chem. Commun. , : 1023 – 1024 .
   Google Scholar
• Thompson , M. J. , Kaplanis , J. N. , Robbins , W. E. and Svoboda , J. A. 1973 . Metabolism of steroids in insects . Adv. Lipids Res. , 11 : 219 – 265 .
   PubMedGoogle Scholar
• Thompson , M. J. , Svoboda , J. A. , Lozano , R. and Wilzer , K. R. 1988 . Profile of free and conjugated ecdysteroids and ecdysteroid acids during embryonic development of Manduca sexta (L.) following maternal incorporation of [14C]-cholesterol . Arch. Insect Biochem. Physiol. , 7 : 157 – 172 .
   Web of Science ®Google Scholar
• Warren , J. T. , Steiner , B. , Dorn , A. , Pak , M. and Gilbert , L. I. 1986 . Metabolism of ecdysteroids during the embryogenesis of Manduca sexta . J. Liquid Chrom. , 9 : 1759 – 1782 .
   Web of Science ®Google Scholar
• Warren , J. T. , Sakurai , S. , Rountree , D. B. and Gilbert , L. I. 1988a . Synthesis and secretion of ecdysteroids by the prothoracic glands of Manduca sexta . J. Insect Physiol. , 34 : 571 – 576 .
   Web of Science ®Google Scholar
• Warren , J. T. , Sakurai , S. , Rountree , D. B. , Gilbert , L. I. , Lee , S.-S. and Nakanishi , K. 1988b . Regulation of the ecdysteroid titer of Manduca sexta: reappraisal of the role of the prothoracic glands . Proc. Natl. Acad. Sci. U.S.A. , 85 : 958 – 962 .
   PubMed Web of Science ®Google Scholar
• Warren , J. T. , Grieneisen , M. L. and Gilbert , L. I. 1990 . Incorporation of [3H]-cholesterol into ecdysteroids by prothoracic glands in vitro, Presented at the IXth Ecdysone Workshop, Paris, Invert. . Reprod. Devel. , 18 : 1 – 2 . 131
   Google Scholar
• Welrich , G. P. , Thompson , M. J. and Svoboda , J. A. 1990 . Enzymes of ecdysone 3-epimerization in Manduca sexta, Presented at the IXth Ecdysone Workshop . Paris, Invert. Reprod. Devel. , 18 : 1 – 2 . 132
   Google Scholar