Diversity of Ecdysteroids in Animal Species

  • René Lafont
  • Jan Koolman

Arthropods contain a significant diversity of ecdysteroids which are used to control their development and reproduction. This diversity is for one part connected with the diversity of the sterol precursors used. Outside Arthropods, ecdysteroids or/and closely related molecules have been found in most other Invertebrates and also in Tunicates. Definite proof for their endogenous origin is however still lacking, and their physiological functions (if any) remain to be established. It is hoped that thanks to the availability of whole genome sequencing of an increasing species number, tools will become available for answering these questions.


Ecdysone 20-hydroxyecdysone makisterone insect arthropod crustacean arachnid mollusc echinoderm tunicate annelid nematode nemertine platyhelminth cnidarian porifera 


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  1. Aiello A, Fattorusso E, Magno S, Menna M (1991) Isolation of five new 5α-hydroxy-6-keto-Δ7 sterols from the marine sponge Oscarella lobularis. Steroids 56:337–340.PubMedGoogle Scholar
  2. Aiello A, Fattorusso E, Menna M (1999) Steroids from sponges: recent reports. Steroids 64:687–714.PubMedGoogle Scholar
  3. Aldrich JR, Svoboda JA, Thompson MJ (1981) Cuticle synthesis and inhibition of vitellogenesis: makisterone A is more active than 20-hydroxyecdysone than 20-hydroxyecdysone in female milkweed bugs. J Exp Zool 218:133–137.Google Scholar
  4. Amagata T, Minoura K, Numata A (1998) Gymnasterones, novel cytotoxic metabolites produced by a fungal strain from a sponge. Tetrahedron Lett 39:3773–3774.Google Scholar
  5. Aribi N, Pitoizet N, Quennedey A, Delbecque JP (1997) 2-Deoxyecdysone is a circulating ecdys-teroid in the beetle Zophobas atratus. Biochim Biophys Acta 1335:246–252.PubMedGoogle Scholar
  6. Barker GC, Rees HH (1990) Ecdysteroids in Nematodes. Parasitol Today 6:384–387.PubMedGoogle Scholar
  7. Barker GC, Chitwood DJ, Rees HH (1990) Ecdysteroids in helminths and annelids. Invertebr Reprod Dev 18:1–11.Google Scholar
  8. Barker GC, Mercer JG, Rees HH, Howells RE (1991) The effect of ecdysteroids on the microfilarial production of Brugia pahangi and the control of meiotic reinitiation in the oocytes of Dirofilaria immitis. Parasitol Res 77:65–71.PubMedGoogle Scholar
  9. Beckstead RB, Thummel CS (2006) Indicted: worms caught using steroids. Cell 124:1137–1140.PubMedGoogle Scholar
  10. Bellés X (1998) Endocrine effectors in insect vitellogenesis. In: Coast GM, Webster SG (eds), Recent Advances in Arthropod Endocrinology. Cambridge University Press, Cambridge, pp 71–90.Google Scholar
  11. Blais C, Lafont R (1991) Biosynthèse des ecdystéroïdes par les glandes prothoraciques de Pieris brassicae (Insecte Lépidoptère). Conversion in vitro d'un précurseur radioactif de la 3-déhy-droecdysone. C R Acad Sci Paris Sér III 313:359–364.Google Scholar
  12. Blais C, Dauphin-Villemant C, Kovganko N, Girault JP, Descoins C Jr, Lafont R (1996) Evidence for the involvement of 3-oxo-Δ4 intermediates in ecdysteroid biosynthesis. Biochem J 320: 413–419.PubMedGoogle Scholar
  13. 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.Google Scholar
  14. Broué F, Liere P, Kenyon C, Baulieu EE (2007) A steroid hormone that extends the lifespan of Caenorhabditis elegans. Aging Cell 6:87–94.PubMedGoogle Scholar
  15. Bückmann D (1984) The phylogeny of hormones and hormonal systems. Nova Acta Leopold NF 56:437–452.Google Scholar
  16. Bückmann D, Starnecker G, Tomaschko KH, Wilhelm E, Lafont R, Girault JP (1986) Isolation and identification of major ecdysteroids from the pycnogonid Pycnogonum litorale Ström (Arthropoda, Pantopoda). J Comp Physiol 156B:759–765.Google Scholar
  17. Butenandt A, Karlson P (1954) Über die Isolierung eines Metamorphosehormons der Insekten in kristallisierter Form. Z Naturforsch 9b:389–391.Google Scholar
  18. Cafieri F, Fattorusso E, Taglialatela-Scafati O (1998) Novel bromopyrrole alkaloids from the sponge Agelas dispar. J Nat Prod 61:122–125.PubMedGoogle Scholar
  19. Campbell RK, Satoh N, Degnan BM (2004) Piecing together evolution of the vertebrate endocrine system. Trends Genet 8:359–366.Google Scholar
  20. Chadha MS, Joshi HK, Mamdapur VR, Sipahimalani AT (1970) C-21 steroids in the defensive secretions of some indian water beetles -II. Tetrahedron 26:2061–2064.Google Scholar
  21. Chapman JC, Lockley WJS, Rees HH, Goodwin TW (1977) Stereochemistry of olefinic bond formation in defensive steroids of Acilius sulcatus (Dysticidae). Eur J Biochem 81:293–298.PubMedGoogle Scholar
  22. Chitwood D (1999) Biochemistry and function of Nematode steroids. Crit Rev Biochem Mol Biol 34:273–284.PubMedGoogle Scholar
  23. Chitwood DJ, Feldlaufer MF (1990) Ecdysteroids in axenically propagated Caenorhabditis elegans. Dev Biol 114:109–118.Google Scholar
  24. Chitwood DJ, McClure MA, Feldlaufer MF, Lusby WR, Oliver JE (1987) Sterol composition and ecdysteroid content of eggs of the root-knot nematodes Meloidogyne incognita and M. arenaria. J Nematol 19:352–360.Google Scholar
  25. Clark AJ, Bloch K (1959) The absence of sterol synthesis in insects. J Biol Chem 234: 2578–2582.PubMedGoogle Scholar
  26. Cleveland LR, Burke AW (1960) Modification induced in the sexual cycles of the protozoa of Cryptocercus by change of host. J Protozool 7:240–245.Google Scholar
  27. Cleveland LR, Burke AW Jr, Karlson P (1960) Ecdysone-induced modifications of the sexual cycles of the protozoa of Cryptocercus. J Protozool 7:229–239.Google Scholar
  28. Connat J-L, Dotson EM, Diehl PA (1988) Apolar conjugates of ecdysteroids are not used as a storage form of molting hormone on the argasid tick Ornithodoros moubata. Arch Insect Biochem Physiol 9:221–235.Google Scholar
  29. Costantino V, Dell'Aversano C, Fattorusso E, Mangoni A (2000) Ecdysteroids from the Caribbean sponge Iotrochota birotulata. Steroids 65:138–142.PubMedGoogle Scholar
  30. Dauphin-Villemant C, Toullec J Y, Böcking D, Blais C, Lafont R (1994) Ecdysteroid biosynthesis by crustacean molting glands: in vitro analysis using dissociated cells of Carcinus maenas Y organs. Communication presented at the XI Ecdysone Workshop, Ceske Budejovice, Abstracts booklet, p 46.Google Scholar
  31. Delbecque J-P, Weidner K, Hoffmann KH (1990) Alternative sites for ecdysteroid production in insects. Invertebr Reprod Dev 18:29–42.Google Scholar
  32. De Mendonça RL, Escrivá H, Bouton, VD, Laudet V, Pierce RJ (2000) Hormones and nuclear receptors in Schistosome development. Parasitol Today 16:233–240.PubMedGoogle Scholar
  33. Dennis RD (1977a) On ecdysone-binding proteins and ecdysone-like material in nematodes. Int J Parasitol 7:181–188.Google Scholar
  34. Dennis RD (1977b) Partial characterization of and the effect of insect growth hormones on the ribosomes and polyribosomes of the nematode Panagrellus redivivus. Int J Parasitol 7: 171–179.Google Scholar
  35. Descamps M, Lafont R (1993) Conversion of different putative ecdysteroid precursors in Lithobius forficatus L. (Myriapoda, Chilopoda). Insect Biochem Mol Biol 23:481–489.Google Scholar
  36. Dinan L (2001) Phytoecdysteroids: biological aspects. Phytochemistry 57:325–339.PubMedGoogle Scholar
  37. Dinan L, Hormann RE (2005) Ecdysteroid agonists and antagonists. In: Gilbert LI, Iatrou K, Gill S (eds), Comprehensive Molecular Insect Science. Elsevier, Oxford, UK vol 3, pp 197–242.Google Scholar
  38. Dinan L, Bourne PC, Meng Y, Sarker SD, Tolentino RB, Whiting P (2001) Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities. Cell Mol Life Sci 58:321–342.PubMedGoogle Scholar
  39. Diop M, Samb A, Costantino V, Fattorusso E, Mangoni A (1996) A new iodinated metabolite and a new alkyl sulfate from the Senegalese sponge Ptilocaulis spiculifer. J Nat Prod 58:2761–2762.Google Scholar
  40. Enmark E, Gustafsson JA (2001) Comparing nuclear receptors in worms, flies and humans. Trends Pharmacol Sci 22:611–615.PubMedGoogle Scholar
  41. Feldlaufer MF, Svoboda JA, (1986) Makisterone A : a 28-carbon insect ecdysteroid. Insect Biochem 16: 45–48.Google Scholar
  42. Feldlaufer MF (1989) Diversity of molting hormones in Insects. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 308–312.Google Scholar
  43. Feldlaufer MF, Weirich GF, Lusby WR, Svoboda JA (1991) Makisterone C: a 29-carbon ecdys-teroid from developing embryos of the cotton stainer bug, Dysdercus fasciatus. Arch Insect Biochem Physiol 18: 71–79.Google Scholar
  44. Feldlaufer MF, Buchmann SL, Lusby WR, Weirich GF, Svoboda JV (1993) Neutral sterols and ecdysteroids of the solitary cactus bee Diadasia rinconis Cockerell (Hymenoptera: Anthophoridae). Arch Insect Biochem Physiol 23:91–98.Google Scholar
  45. Foster JM, Mercer JG, Rees HH (1992) Analysis of ecdysteroids in the trematodes, Schistosoma mansoni and Fasciola hepatica. Trop Med Parasitol 43: 239–244.PubMedGoogle Scholar
  46. Fraenkel G (1935) A hormone causing pupation in the blowfly, Calliphora erythrocephala. Proc Roy Soc B 118:1–12.Google Scholar
  47. Franke S, Käuser G (1989) Occurrence and hormonal role of ecdysteroids in non-arthropods. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 296–307.Google Scholar
  48. Fujimoto Y, Miyasaka S, Ikeda T, Ikekawa N, Ohnishi E, Mizuno T, Watanabe K (1985) An unusual ecdysteroid (20S)-cholesta-7,14-diene-3β,5α,6α,20,25-pentaol (bombycosterol) from the ovaries of the silkworm, Bombyx mori. J Chem Soc Chem Commun, 10–12.Google Scholar
  49. Fukuzawa A, Miyamoto NM, Kumagai Y, Masamune T (1986) Ecdysone-like metabolites, 14α-hydroxypinnasterols, from the red alga Laurencia pinnata. Phytochemistry 25:1305–1307.Google Scholar
  50. Gaillet N (1985) Mise en évidence et rôle physiologique des ecdystéroïdes chez les Néréidiens (Annélides Polychètes), Thesis, Université de Lille, France, 70 pp.Google Scholar
  51. Galbraith MN, Horn DHS, Hocks P, Schulz G, Hoffmeister H (1967) The identity of 20-hydrox-yecdysones from various sources. Naturwissenschaften 54:471–472.PubMedGoogle Scholar
  52. Galbraith MN, Horn DHS, Middleton EJ, Thomson JA, Siddall JB, Hafferl W (1969). The catabolism of crustecdysone in the blowfly Calliphora stygia. J Chem Soc Chem Commun, 1134–1135.Google Scholar
  53. Garcia M, Girault JP, Lafont R (1986) Ecdysteroid metabolism in the terrestrial snail, Cepaea nemoralis. Invertebr Reprod Dev 9:43–58.Google Scholar
  54. Garcia M, Gharbi J, Girault JP, Hétru C, Lafont R (1989) Ecdysteroid metabolism in leeches. Invertebr Reprod Dev 15:57–68.Google Scholar
  55. Garcia M, Griffond B, Lafont R (1995) What are the origins of ecdysteroids in gastropods? Gen Comp Endocrinol 97:76–85.PubMedGoogle Scholar
  56. Gissendanner CR, Crossgrove K; Kraus KA, Maina CV, Sluder AE (2004) Expression and function of conserved nuclear receptor genes in Cænorhabditis elegans. Dev Biol 15:399–416.Google Scholar
  57. Gomot A (1984). Recherche d'ecdystéroïdes chez l'escargot Helix aspersa Müller, Diploma, University of Franche-Comté Besançon, 32 pp.Google Scholar
  58. Goudey-Perrière F, Fokam-Simo B, Maccario J, Perrière C, Gayral P (1992) Effects of ecdysteroids on reproductive physiology of Nippostrongylus brasiliensis (Nematoda) in vivo. Comp Biochem Physiol 103C:105–109.Google Scholar
  59. Guerriero A, Pietra F (1985) Isolation in large amounts of the rare plant ecdysteroid ajugasterone C from the mediterranean zoanthid Gerardia savaglia. Comp Biochem Physiol 80B:277–278.Google Scholar
  60. Guerriero A, Traldi P, Pietra F (1986) Gerardiasterone, a new ecdysteroid with a 20,22,23,25-tet-rahydroxylated side chain from the mediterranean zoanthid Gerardia savaglia. J Chem Soc Chem Commun, 40–41.Google Scholar
  61. Hagedorn HH (1989) Physiological roles of hemolymph ecdysteroids in the adult insect. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 279–295.Google Scholar
  62. Hagedorn HH, O'Connor JD, Fuchs MS, Sage B, Schlaeger DA, Böhm MK (1975). The ovary as a source of α-ecdysone in an adult mosquito. Proc Natl Acad Sci USA 72:3255–3259.PubMedGoogle Scholar
  63. Hampshire F, Horn DHS (1966) Structure of crustecdysone, a crustacean moulting hormone. J Chem Soc Chem Commun 2:37–38.Google Scholar
  64. Hayakawa Y, Furihata K, Shin-ya K, Mori T (2003) Gymnasterol, a new antitumor steroid against IGF-dependent cells from Gymnascella dankaliensis. Tetrahedron Lett 44:1165–1166.Google Scholar
  65. Hikino H, Ohizumi U, Takemoto T (1975). Steroid metabolism in Bombyx mori. I. Catabolism of ponasterone A and ecdysterone in Bombyx mori. Hoppe Seyler's Z Physiol Chem 356: 309–314.PubMedGoogle Scholar
  66. Hitcho PJ, Thorson RE (1971) Possible moulting and maturation controls of Trichinella spiralis. J Parasitol 57:787–793.PubMedGoogle Scholar
  67. Hoffmann, JA, Charlet M (1985) Les ecdystéroïdes chez les Invertébrés. Ann Sci Nat, Zool 13ème Série 7:215–228.Google Scholar
  68. Honda T, Fujii I, Hirayama N, Ishikawa D, Kawagishi H, Song KS, Yoo ID (1996) (14α,22E)-14-Hydroxyergosta-4,7,22-triene-3,6-dione, C28H40O3. Acta Cryst C 52: 1550–1552.Google Scholar
  69. Hopkins PM (1992) Hormonal control of the molt cycle in the fiddler crab Uca pugilator. Am Zool 32:450–458.Google Scholar
  70. Horn DHS (1989) Historical introduction. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 8–19.Google Scholar
  71. Horn DHS, Middleton EJ, Wunderlich JA (1966) Identity of the moulting hormones of Insects and Crustaceans. J Chem Soc Chem Commun, 339–341.Google Scholar
  72. Horn DHS, Wilkie JS, Thomson JA (1974) Isolation of β-ecdysone (20-hydroxyecdysone) from the parasitic nematode Ascaris lumbricoides. Experientia 30:1109–1110.PubMedGoogle Scholar
  73. Huber R, Hoppe W (1965) Die Kristall- und Molekül-strukturanalyse des Insektenverpuppung-shormons Ecdyson mit der automatisierten Faltmolekülmethode. Chem Ber 98: 2403–2424.PubMedGoogle Scholar
  74. Isaac RE, Slinger AJ (1989) Storage and excretion of ecdysteroids. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 250–253.Google Scholar
  75. Jarvis TD, Earley FGP, Rees HH (1994) Ecdysteroid biosynthesis in larval testes of Spodoptera littoralis. Insect Biochem Mol Biol 24:531–537.Google Scholar
  76. Jegla TC (1990) Evidence for ecdysteroids as molting hormones in chelicerata, crustacea, and myriapoda. In: Gupta AP (ed), Morphogenetic Hormones of Arthropods. Rutgers University Press, New Brunswick, NJ, vol 1, pp 229–273.Google Scholar
  77. Jenkins SP, Brown MR, Lea AO (1992) Inactive prothoracic glands in larvae and pupae of Aedes aegypti: ecdysteroid release by tissues in the thorax and the abdomen. Insect Biochem Mol Biol 22:553–559.Google Scholar
  78. Kalarani V, Reddy DC, Habibi HR, El-Shimy N, Davies DR (1995) Occurrence and hormonal action of ecdysone on gametogenesis and energy utilization in the leech Nephelopsis obscura (Erpobdellidae). J Exp Zool 273:511–518.Google Scholar
  79. Kaplanis JN, Dutky SR, Robbins WE, Thompson MJ, Lindquist EI (1975) Makisterone A: a new 28-carbon hexahydroxy moulting hormone from the embryo of the milkweed bug. Science 190:681–682PubMedGoogle Scholar
  80. Karlson P, Stamm-Menéndez MD (1956) Notiz über den Nachweis von Metamorphose-Hormon in den Imagines von Bombyx mori. Hoppe Seyler's Z Physiol Chem 306:109–111.PubMedGoogle Scholar
  81. Karlson P, Hoffmeister H, Hoppe W, Huber R (1963) Zur Chemie des Ecdysons. Justus Liebigs Ann Chem 662:1–20.Google Scholar
  82. Käuser G (1989) On the evolution of ecdysteroid hormones. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 327–336.Google Scholar
  83. Kiriishi S, Rountree DB, Sakurai S, Gilbert LI (1990) Prothoracic gland synthesis of 3-dehydro-ecdysone and its hemolymph 3β-reductase-mediated conversion to ecdysone in representative insects. Experientia 46:716–721.PubMedGoogle Scholar
  84. Koolman J (1990) Zooecdysteroids. Zool Sci 7:563–580.Google Scholar
  85. Koolman J, Moeller H (1986) Diagnosis of major helminth infections by RIA detection of ecdys-teroids in urine and serum. Insect Biochem 16:287–291.Google Scholar
  86. Koolman J, Scheller K, Bodenstein H (1979) Ecdysteroids in the adult male blowfly, Calliphora vicina. Experientia 35:134–135.Google Scholar
  87. Koolman J, Walter J, Zahner H (1984) Ecdysteroids in Helminths. In: Hoffmann J, Porchet M (eds), Biosynthesis, Metabolism and Mode of Action of Invertebrate Hormones. Springer, Berlin, pp 323–330.Google Scholar
  88. Krishnakumaran A, Schneiderman HA (1968) Chemical control of molting in arthropods. Nature 221:601–603.Google Scholar
  89. Lachaise F (1989) Diversity of Molting Hormones in Crustacea. Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 313–318.Google Scholar
  90. Lachaise F (1990) Synthesis, metabolism, and effects on molting of ecdysteroids in Crustacea, Chelicerata, and Myriapoda. In: Gupta AP (ed), Morphogenetic Hormones of Arthropods. Rutgers University Press, New Brunswick, NJ, vol 1, pp 275–323.Google Scholar
  91. Lachaise F, Le Roux A, Hubert M, Lafont R (1993) The molting glands of Crustaceans: localization, activity, and endocrine control (review). J Crustacean Biol 13:198–234.Google Scholar
  92. Lafont R (1991) Reverse endocrinology, or “hormones” seeking functions. Insect Biochem 21: 697–721.Google Scholar
  93. Lafont R (1997) Ecdysteroids and related molecules from plants and animals. Arch Insect Biochem Physiol 35:3–20.Google Scholar
  94. Lafont R, Harmatha J, Marion-Poll F, Dinan L, Wilson ID (2002) Ecdybase — The Ecdysone Handbook, 3rd Edition, Cybersales, Praha, 2002, online
  95. Lafont R (2000) The endocrinology of Invertebrates. Ecotoxicology 9:41–57.Google Scholar
  96. Lafont R, Mathieu M (2007) Steroids in aquatic invertebrates. Ecotoxicology 16:109–130.PubMedGoogle Scholar
  97. Lafont R, Connat J-L, Delbecque J-P, Dauphin-Villemant C, Blais C, Garcia M (1995) Comparative studies on Ecdysteroids. In: Ohnishi E, Takahashi S Y, Sonobe H (eds), Recent Advances in Insect Biochemistry and Molecular Biology. Nagoya University Press, Nagoya, pp 45–91.Google Scholar
  98. Lafont R, Dauphin-Villemant C, Warren J, Rees HH (2005) Ecdysteroid chemistry and biochemistry. In: Gilbert LI, Iatrou K, Gill S (eds), Comprehensive Molecular Insect Science. Elsevier, Oxford, UK vol 3, pp 125–195.Google Scholar
  99. Laudet V, Bonneton F (2005) Evolution of nuclear hormone receptors in Insects. In: Gilbert LI, Iatrou K, Gill S (eds), Comprehensive Molecular Insect Science. Elsevier, Oxford, UK vol 3, pp 287–318.Google Scholar
  100. Laurent P, Braekman JC, Daloze D, Pasteels JM (2003) An ecdysteroid (22-acetyl-20-hydrox-yecdysone) from the defense gland secretion of an insect: Chrysolina carnifex (Coleoptera: Chrysomelidae). Chemoecology 13:109–111.Google Scholar
  101. Loeb MJ, Woods CW, Brandt EP, Borkovec AB (1982) Larval testes of the tobacco budworm. A new source of insect ecdysteroids. Science 218:896–898.PubMedGoogle Scholar
  102. Lord JC, Hall DW (1983) Sporulation of Amblyospora (Microspora) in female Culex salinarius: induction by 20-hydroxyecdysone. Parasitology 87:377–383.Google Scholar
  103. Malorni A, Minale L, Riccio L (1978) Steroids from sponges: occurrence of steroidal Δ4,7−3,6-dike-tones in the marine sponge Raphidostila incisa. Nouv J Chimie 2:351–354.Google Scholar
  104. Matsumoto E, Matsui M, Tamura H (2003) Purification of sulfotransferase for 20-hydroxyecdys-one from the larval fat body of a fleshfly, Sarcophaga peregrina. Biosci Biotechnol Biochem 67:1780–1785.PubMedGoogle Scholar
  105. Mauchamp B, Royer C, Kerhoas L, Einhorn J (1993) MS/MS analyses of ecdysteroids in developing eggs of Dysdercus fasciatus. Insect Biochem Mol Biol 23:199–205.Google Scholar
  106. Maurer P, Girault JP, Larchevêque M, Lafont R (1993) 24-Epi-makisterone A (not makister-one A) is the major ecdysteroid in the leaf-cutting ant Acromyrmex octospinosus (Reich) (Hymenoptera, Formicidae: Attini). Arch Insect Biochem Physiol 23:29–35.Google Scholar
  107. Meaney S (2005) Is C-26 hydroxylation an evolutionarily conserved steroid inactivation mechanism? FASEB J 19:1220–1224.PubMedGoogle Scholar
  108. Mendis AHW, Rose ME, Rees HH, Goodwin TW (1983) Ecdysteroids in adults of the nematode, Dirofilaria immitis. Mol Biochem Parasitol 9:209–226.PubMedGoogle Scholar
  109. Mendis AHW, Rees HH, Goodwin TW (1984) The occurrence of ecdysteroids in the cestode, Moniezia expansa. Mol Biochem Parasitol 10:123–138.PubMedGoogle Scholar
  110. Mercer JG, Munn AE, Rees HH (1987). Echinococcus granulosus: occurrence of ecdysteroids in protoscoleces and hydatid cyst fluid. Mol Biochem Parasitol 24:203–214.PubMedGoogle Scholar
  111. Mercer JG, Barker GC, McCall JW, Howells RE, Rees HH (1989) Studies on the biosynthesis and fate of ecdysteroids in filarial nematodes. Trop Med Parasitol 40:429–433.PubMedGoogle Scholar
  112. Miyata Y, Diyabalanage T, Amsler CD, McClintock JB, Valeriote FA, Baker BJA (2007) New ecdysteroids from the antarctic Tunicate Synoicum adareanum. J Nat Prod 70:1859–1864PubMedGoogle Scholar
  113. Mizuta T, Kubokawa K (2007) Presence of sex steroids and cytochrome P450 genes in Amphioxus. Endocrinology 148:3554–3565.PubMedGoogle Scholar
  114. Motola DL, Cummins CL, Rottiers V, Sharma KK, Li T, Li Y, Suino-Powell K, Xu, HE, Auchus RJ, Antebi A, Mangelsdorf DJ (2006) Identification of ligands for DAF-12 that govern dauer formation and reproduction in C. elegans. Cell 124:1209–1223.PubMedGoogle Scholar
  115. Mukai ST, Steel CGH, Saleuddin ASM (2001) Partial characterization of the secretory material from the dorsal bodies in the snail Helisoma duryi (Mollusca: Pulmonata), and its effects on reproduction. Invertebr Biol 120:149–161.Google Scholar
  116. Nes WR, McKean ML (1977) Occurrence, physiology and ecology of sterols. In: Biochemistry of Steroids and Other Isopentenoids, University Park Press, Baltimore, MD, pp. 411–533.Google Scholar
  117. Nirdé P, Torpier G, De Reggi ML, Capron A (1983). Ecdysone and 20-hydroxyecdysone: new hormones for the human parasite Schistosoma mansoni. FEBS Lett 151:223–227.PubMedGoogle Scholar
  118. Nirdé P, De Reggi ML, Tsoupras G, Torpier G, Fressancourt P, Capron A (1984a) Excretion of ecdysteroids by schistosomes as a marker of parasite infection. FEBS Lett 168:235–240.Google Scholar
  119. Nirdé P, Torpier G, Capron A, Delaage M, De Reggi ML (1984b) Ecdysteroids in schistosomes and host-parasite relationship. In: Hoffmann J, Porchet M (eds), Biosynthesis, Metabolism and Mode of Action of Invertebrate Hormones. Springer, Berlin, pp 331–337.Google Scholar
  120. Nolte A, Koolman J, Dorlöchter M, Straub H (1986) Ecdysteroid in the dorsal bodies of Pulmonates (Gastropoda): synthesis and release of ecdysone. Comp Biochem Physiol 84A:777–782.Google Scholar
  121. O'Hanlon GM, Howarth OW, Rees HH (1987) Identification of ecdysone-25-O-β-D-glucopyranoside as a new metabolite of ecdysone in the nematode Parascaris equorum. Biochem J 248:305–307.PubMedGoogle Scholar
  122. Okazaki RK, Snyder MJ, Chang ES (1988) Ecdysteroids in Nemerteans: presence and physiological role. Hydrobiologia 156:153–160.Google Scholar
  123. Okazaki RK, Snyder MJ, Grimm CC, Chang ES (1998) Ecdysteroids in Nemerteans: further characterization and identification. Hydrobiologia 365:281–285.Google Scholar
  124. Parameswaran PS, Naik CG, Gonsalves C, Achuthankutty CT (2001) Isolation of 2-deoxy-ecdysterone, a novel oxytocic agent from a marine Zoanthus sp. J Indian Inst Sci 81: 169–173.Google Scholar
  125. Pondeville E, Maria A, Jacques JC, Bourgouin C, Dauphin-Villemant C (2007) Ecdysteroid biosynthesis in adult male and female Anopheles gambiae. J Insect Sci 7:13.Google Scholar
  126. Porchet M, Gaillet N, Sauber F, Charlet M, Hoffmann JA (1984) Ecdysteroids in Annelids. In: Hoffmann J, Porchet M (eds), Biosynthesis, Metabolism and Mode of Action of Invertebrate Hormones. Springer, Berlin, pp 346–348.Google Scholar
  127. Ramaro M, Kemper B (1995) Substitution at residue 473 confers progesterone 21-hydroxylase activity to cytochrome P450 2C2. Mol Pharmacol 48:417–424.Google Scholar
  128. Redfern CPF (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 USA 81:5643–5647.PubMedGoogle Scholar
  129. Redfern CPF (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
  130. Redfern CPF (1989) Ecdysiosynthetic tissues. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 182–187.Google Scholar
  131. Rees HH (1989) Zooecdysteroids: structures and occurrence. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 28–38.Google Scholar
  132. Rees HH, Mendis AHW (1984) The occurrence and possible physiological significance of ecdysteroids during nematode and cestode development. In: Hoffmann JA, Porchet M (eds) Biosynthesis, Metabolism and Mode of Action of Invertebrate Hormones. Springer, Berlin, pp 338–345.Google Scholar
  133. Regali A (1996) Contribution à l ‘étude des besoins alimentaires en stéroïdes de Bombus terrestris (L.), Thesis, University of Mons-Hainaut, Belgium, 143 pp.Google Scholar
  134. Reuland M, Sauber F, Boilly Y, Charlet M (1987) Further investigations on ecdysteroids in Annelids: predominance of 2-deoxyecdysone-like ecdysteroids in the three classes of Annelids, Polychaeta, Oligochaeta and Hirudinea. Communication presented at the VIII Ecdysone Workshop, Marburg, Germany.Google Scholar
  135. Rewitz KF, O'Connor MB, Gilbert LI (2007) Molecular evolution of the insect Halloween family of cytochrome P450s: phylogeny, gene organization and functional conservation. Insect Biochem Mol Biol 37:741–753.PubMedGoogle Scholar
  136. Romer F (1979) Ecdysteroids in snails. Naturwissenschaften 66:471.Google Scholar
  137. Romer F, Gnatzy W (1981) Arachnid oenocytes: ecdysone synthesis in the legs of harvestmen (Opilionidae). Cell Tissue Res 216:449–453.PubMedGoogle Scholar
  138. Rottiers V, Motola DL, gerisch B, Cummins CL, Nishiwaki K, Mangelsdorf DJ, Antebi A (2006) Hormonal control of C. elegans dauer formation and life span by a Rieske-like oxygenase. Dev Cell 10:473–482.PubMedGoogle Scholar
  139. Rudolph PH, Spaziani E (1992) Formation of ecdysteroids by Y organs of the crab, Menippe mercenaria. II. Incorporation of cholesterol into 7-dehydrocholesterol and secretion products in vitro. Gen Comp Endocrinol 88:235–242.PubMedGoogle Scholar
  140. Sarma NS, Sri Rama Krishna M, Ramakrishna Rao S (2005) Sterol ring system oxidation pattern in marine sponges. Mar Drugs 3:84–111.Google Scholar
  141. Sauber F, Reuland M, Berchtold JP, Hétru C, Tsoupras G, Luu B, Moritz ME, Hoffmann, JA (1983) Cycle de mue et ecdystéroïdes chez une Sangsue, Hirudo medicinalis. C R Acad Sci Sér III 296:413–418.Google Scholar
  142. Schildknecht H, Siewerdt R, Maschwitz U (1967) Über Arthropodenabwehrstoffe, XXIII. Cybisteron, ein neues Arthropoden-Steroid. Liebigs Ann Chem 703:182–189.Google Scholar
  143. Searle PA, Molinski TF (1995) 4-Dehydroecdysterone, a new ecdysteroid from the zoanthid Parazoanthus sp. J Nat Prod 58:264–268.PubMedGoogle Scholar
  144. Shampengtong L, Wong KP (1989) An in vitro assay of 20-hydroxyecdysone sulfotransferase in the mosquito, Aedes togoi. Insect Biochem 19:191–196.Google Scholar
  145. Shigemori H, Sato Y, Kagata T, Kobayashi J (1999) Palythoalones A and B, new ecdysteroids from the marine zoanthid Palythoa australiae. J Nat Prod 62:372–374.PubMedGoogle Scholar
  146. Sieglaff DH, Adams Duncan K, Brown MR (2005) Expression of genes encoding proteins involved in ecdysteroidogenesis in the female mosquito, Aedes aegypti. Insect Biochem Mol Biol 35:471–490.PubMedGoogle Scholar
  147. Simon P, Koolman J (1989) Ecdysteroids in Vertebrates : pharmacological apsects. In: Koolman J (ed), Ecdysone, from chemistry to mode of action, Georg Thieme Verlag, Stuttgart. pp 254–259.Google Scholar
  148. Snyder MJ, Okazaki RK, Chang ES (1992) Nemertean ecdysteroids: relationship to reproduction. Invertebr Reprod Dev 21:7–13.Google Scholar
  149. Sonobe H, Yamada R (2004) Ecdysteroids during early embryonic development in silkworm Bombyx mori: metabolism and functions. Zool Sci 21:503–516PubMedGoogle Scholar
  150. Spaziani E, Rees HH, Wang WL, Watson RD (1989) Evidence that Y-organs of the crab Cancer antennarius secrete 3-dehydroecdysone. Mol Cell Endocrinol 66:17–25.PubMedGoogle Scholar
  151. Spindler KD (1988) Parasites and hormones. In: Mehlhorn H (ed), Parasites. Springer, New York, pp 465–476.Google Scholar
  152. Spindler KD (1989) Hormonal role of ecdysteroids in Crustacea, Chelicerata and other Arthropods. In: Koolman J (ed), Ecdysone, from Chemistry to Mode of Action. Georg Thieme Verlag, Stuttgart, pp 290–295.Google Scholar
  153. Sturaro A, Guerriero A, Declauser R, Pietra F (1982) A new, unexpected marine source of a moulting hormone: isolation of ecdysterone in large amounts from the zoanthid Gerardia savaglia. Experientia 38:1184–1185.Google Scholar
  154. Suksamrarn A, Jankam A, Tarnchompoo B, Putchakarn S (2002) Ecdysteroids from a Zoanthus sp. J Nat Prod 65:1194–1197.PubMedGoogle Scholar
  155. Takemoto T, Ogawa S, Nishimoto N, Hoffmeister H (1967) Steroide mit Häutungshormon-4ktivität aus Tieren und Pflanzen. Z Naturforsch B 22: 681–682.PubMedGoogle Scholar
  156. Thompson MJ, Svoboda JA, Lusby WR, Rees HH, Oliver JE, Weirich GF, Wilzer KR (1985) Biosynthesis of a C21 steroid conjugate in an insect: the conversion of [14C]cholesterol to 5-[14C]pregnen-3α,20α-diol glucoside in the tobacco hornworm, Manduca sexta. J Biol Chem 260:15410–15412.PubMedGoogle Scholar
  157. Thornton JW, Need E, Crews D (2003) Resurrecting the ancestral receptor: ancient origin of estrogen signalling. Science 301:1714–1717.PubMedGoogle Scholar
  158. Tomaschko K-H (1994) Defensive secretion of ecdysteroids in Pycnogonum litorale (Arthropoda, Pantopoda). Z Naturforsch 49c:367–371.Google Scholar
  159. Tomaschko K-H (1995) Autoradiographic and morphological investigations of the defensive ecdysteroid glands in adult Pycnogonum litorale (Arthropoda: Pantopoda). Eur J Entomol 92:105–112.Google Scholar
  160. Tomaschko K-H (1999) Nongenomic effect of ecdysteroids. Arch Insect Biochem Physiol 41:89–98.Google Scholar
  161. Walgraeve HRMA, Verhaert PDEM (1988) Presence and function of ecdysteroids in Invertebrates. ISI Atl Sci 1:164–172.Google Scholar
  162. Wang YS, Crews P (1996) Geodisterol, a novel polyoxygenated sterol with an aromatic A ring from the tropical marine sponge Geodia sp. Tetrahedron Lett 37:8145–8146.Google Scholar
  163. Warbrick EV, Barker GC, Rees HH, Howells RE (1993) The effect of invertebrate hormones and potential hormone inhibitors on the third larval moult of the filarial nematode, Dirofilaria immitis, in vitro. Parasitology 107:459–463.PubMedGoogle Scholar
  164. Warren JT, Sakurai S, Rountree DB, Gilbert LI (1988) Synthesis and secretion of ecdysteroids by the prothoracic glands of Manduca sexta. J Insect Physiol 34:571–576.Google Scholar
  165. Whitehead DL (1977) Steroids enhance shell regeneration in an aquatic gastropod (Biomphalaria glabrata). Comp Biochem Physiol 58C:137–141.Google Scholar
  166. Whitehead DL, Saleuddin ASM (1978) Steroids promote shell regeneration in Helix aspersa (Gastropoda: Pulmonata). Comp Biochem Physiol 59C:5–10.Google Scholar
  167. Whitehead DL, Sellheyer K (1982) The identification of ecdysterone (20-hydroxyecdysone) in 3 species of molluscs (Gastropoda: Pulmonata). Experientia 38:1249–1251.Google Scholar
  168. Williams DE, Ayer SW, Andersen J (1986) Diaulusterols A and B from the skin extracts of the dorid nudibranch Diaulula sandiegensis. Can J Chem 64:1527–1529.Google Scholar
  169. Zhu XX, Oliver JH Jr, Dotson EM (1991) Epidermis as the source of ecdysone in an argasid tick. Proc Natl Acad Sci USA 88:3744–3647.PubMedGoogle Scholar
  170. Zipser B, Bradford JJ, Hollingsworth RI (1998) Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis. Comp Biochem Physiol 120C:269–282.Google Scholar

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© Springer Science + Business Media B.V 2009

Authors and Affiliations

  1. 1.Laboratoire de Biochimie Structurale et Fonctionnelle des ProtéinesUniversité Pierre et Marie CurieParis cedex 05France
  2. 2.Physiologisch-Chemisches InstitutUniversity of MarburgMarburgGermany

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