Skip to main content
SpringerLink
Log in

Steroids in aquatic invertebrates

  • Published:
Ecotoxicology Aims and scope Submit manuscript

Abstract

Steroid molecules are present in all invertebrates, and some of them have established hormonal roles: this is the case for ecdysteroids in arthropods and, to a lesser extent, for vertebrate-type steroids in molluscs. Steroids are not only hormones, they may also fulfill many other functions in chemical communication, chemical defense or even digestive physiology. The increasing occurrence of endocrine disruption problems caused by environmental pollutants, which interfere in particular with reproductive physiology of vertebrates but also of invertebrates has made necessary to better understand the endocrine physiology of the latter and the role of steroids in these processes. So many attempts are being made to better understand the endocrine roles of steroids in arthropods and molluscs, and to establish whether they also fulfill similar functions in other invertebrate phyla. At the moment, both the precise identification of these steroids, the determination of their origin (endogenous versus exogenous) and of their mechanism of action are under active investigation. This research takes profit of the development of genome sequencing programs on many invertebrate species, which allow the identification of receptors and/or biosynthetic enzymes, when related to their vertebrate counterparts, but the story is not so simple, as will be exemplified by estrogen receptors of molluscs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Agafonova IG, Aminin DI, Shubina LK, Fedorov SN (2002) Influence of polyhydroxysteroids on [Ca2+]i. Steroids 67:695–701

    Article  CAS  Google Scholar 

  • Aiello A, Fattorusso E, Menna M (1999) Steroids from sponges: recent reports. Steroids 64:687–714

    Article  CAS  Google Scholar 

  • Atkinson S, Atkinson MJ (1992) Detection of estradiol-17β during a mass coral spawn. Coral Reefs 11:33–35

    Article  Google Scholar 

  • Atkinson S, Atkinson MJ, Tarrant AM (2003) Estrogens from sewage in coastal marine environments. Environ Health Perspect 111:531–535

    Article  CAS  Google Scholar 

  • Baker ME (1995) Endocrine activity of plant-derived compounds: an evolutionary perspective. Proc Soc Exp Biol Med 208:131–138

    CAS  Google Scholar 

  • Baker ME (1997) Steroid receptor phylogeny and vertebrate origins. Mol Cell Endocrinol 135:101–107

    Article  CAS  Google Scholar 

  • Barker GC, Chitwood DJ, Rees HH (1990) Ecdysteroids in helminths and annelids. Invertebr Reprod Dev 18:1–11

    CAS  Google Scholar 

  • Barker MF, Xu RA (1993) Effects of estrogens on gametogenesis and steroid levels in the ovaries and pyloric caeca of Scleracterias mollis (Echinodermata: Asteridae). Invertebr Reprod Dev 24:53–58

    CAS  Google Scholar 

  • 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 

  • Bettin C, Oehlmann J, Stroben E (1996) TBT-induced imposex in marine gastropods is mediated by an increasing androgen level. Helgolander Meeresunter 50:299–317

    Article  Google Scholar 

  • Blanchet M-F, Ozon R, Meusy J-J (1972) Metabolism of steroids, in vitro, in the male crab Carcinus maenas Linné. Comp Biochem Physiol B 41:251–261

    Article  CAS  Google Scholar 

  • Blumberg B, Sabbagh W Jr, Juguilon H, Bolado J Jr, van Meter CM, Ong ES, Evans RM (1998) SXR, a novel steroid and xenobiotic sensing nuclear receptor. Genes Dev 12:3195–3205

    CAS  Google Scholar 

  • Botticelli CR, Hisaw FL Jr, Wotiz HH (1960) Estradiol-17β and progesterone in ovaries of starfish (Pisaster ochraceous). Proc Soc Exp Biol Med 103:875–877

    CAS  Google Scholar 

  • Botticelli CR, Hisaw FL Jr, Wotiz HH (1961) Estrogens and progesterone in the sea urchin (Strongylocentrotus fransciscanus) and Pecten (Pecten hericius). Proc Soc Exp Biol Med 106:887–889

    CAS  Google Scholar 

  • Breitholtz M, Bengtson BE (2001) Oestrogens have no hormonal effect on the development and reproduction of the harpacticoid copepod Nitocra spinipes. Mar Pollut Bull 42:879–886

    Article  CAS  Google Scholar 

  • Briggs MH (1972) Metabolism of steroid hormones by schistosomes. Biochim Biophys Acta 280:481–485

    CAS  Google Scholar 

  • Bückmann D (1984) The phylogeny of hormones and hormonal systems. Nova Acta Leopold NF56:437–452

    Google Scholar 

  • Bückmann D, Starnecker G, Tomaschko K-H, Wilhelm E, Lafont R, Girault J-P (1986) Isolation and identification of major ecdysteroids from the pycnogonid Pycnogonum litorale Ström (Arthropoda, Pantopoda). J Comp Physiol 156B:759–765

    Google Scholar 

  • Burns B-O, Sangalang GD, Freeman HC, McMenemy M (1984) Isolation and identification of testosterone from serum and testes of American lobster (Homarus americanus). Gen Comp Endocrinol 54:429–432

    Article  CAS  Google Scholar 

  • Cafieri F, Fattorusso E, Taglialatela-Scafati O (1998) Novel bromopyrrole alkaloids from the sponge Agelas dispar. J Nat Prod 61:122–125

    Article  CAS  Google Scholar 

  • Canesi L, Ciacci C, Betti M, Lorusso LC, Marchi B, Burattini S, Falcieri E, Gallo G (2004) Rapid effect of 17β-estradiol on cell signaling and function of Mytilus edulis. Gen Comp Endocrinol 136:58–71

    Article  CAS  Google Scholar 

  • Cardoso AM, Barros CMF, Ferrer Correia AJ, Cardoso JM, Cortez A, Carvalho F, Baldaia L (1997) Identification of vertebrate type steroid hormones in the shrimp Penaeus japonicus by tandem mass spectrometry and sequential product ion scanning. J Am Soc Mass Spectrom 8:365–370

    Article  CAS  Google Scholar 

  • Carreau S, Drosdowsky M (1977) The in vitro biosynthesis of steroids by the gonad of the cuttlefish Sepia officinalis. Gen Comp Endocrinol 33:554–565

    Article  CAS  Google Scholar 

  • Chaix SM, De Reggi M (1982) Ecdysteroid levels during ovarian development and embryogenesis in the spider crab Acanthonyx lunulatus. Gen Comp Endocrinol 47:7–14

    Article  CAS  Google Scholar 

  • Chang ES, Kaufman WR (2005) Endocrinology of crustacea and chelicerata. In: Gilbert LI, Iatrou K, Gill SS (eds), Comprehensive molecular insect science, vol 3. Elsevier/Pergamon, Amsterdam, pp 805–842

    Google Scholar 

  • Chitwood DJ (1999) Biochemistry and function of Nematode steroids. Crit Rev Biochem Mol Biol 34:273–284

    Article  CAS  Google Scholar 

  • Chung ACK, Durica DS, Clifton SW, Roe BA, Hopkins PM (1998) Cloning of crustacean ecdysteroid receptor and retinoid-X receptor gene homologs and elevation of retinoid-X receptor mRNA by retinoic acid. Mol Cell Endocrinol 139:209–227

    Article  CAS  Google Scholar 

  • Colombo L, Belvedere P (1976) Gonadal steroidogenesis in echinoderms. Gen Comp Endocrinol 29:255–256

    Google Scholar 

  • Costantino V, Dell’Aversano C, Fattorusso E, Mangoni A (2000) Ecdysteroids from the Caribbean sponge Iotrochota birotulata. Steroids 65:138–142

    Article  CAS  Google Scholar 

  • Couch EF, Hagino N, Lee JW (1987) Changes in estradiol and progesterone immunoreactivity in tissues of the lobster (Homarus americanus) with developing and immature ovaries. Comp Biochem Physiol A 87:765–770

    Article  Google Scholar 

  • D’Aniello A, Di Cosmo A, Di Cristo C, Assisi L, Botte V, Di Fiore MM (1996) Occurrence of sex steroid hormones and their binding proteins in Octopus vulgaris Lam. Biochem Biophys Res Commun 227:782–788

    Article  CAS  Google Scholar 

  • Das S, Thomas P (1999) Pesticides interfere with the nongenomic action of a progestogen on meiotic maturation by binding to its plasma membrane receptor in fish oocytes. Endocrinology 140:1953–1956

    Article  CAS  Google Scholar 

  • Davies KA, Fischer JM (1994) On hormonal control of moulting in Aphelenchus avenae (Nematoda: Aphelenchida). Int J Parasitol 24:649–655

    Article  CAS  Google Scholar 

  • deFur P (2004) Use and role of invertebrate models in endocrine disruptor research and testing. ILAR J 45:484–492

    CAS  Google Scholar 

  • deFur PI, Crane M, Ingersoll C, Tattersfield L (1999) Endocrine disruption in invertebrates: endocrinology, testing, and assessment. SETAC Press, Pensacola, 303pp

    Google Scholar 

  • DeLongcamp D, Lubet P, Drosdowsky M (1974) The in vitro biosynthesis of steroids by the gonad of the mussel (Mytilus edulis). Gen Comp Endocrionol 22:116–127

    Article  CAS  Google Scholar 

  • Dettner K (1987) Chemosystematics and evolution of beetle chemical defenses. Ann Rev Entomol 32:17–48

    Article  CAS  Google Scholar 

  • De Waal M, Portman J, Voogt PA (1982) Steroid receptors in invertebrates: a specific 17β-estradiol binding protein in a seastar. Mar Biol Lett 3:317–323

    Google Scholar 

  • Di Cosmo A, Di Cristo C, Paolucci M (2002) An estradiol-17β receptor in the reproductive system of the female of Octopus vulgaris: characterization and immunolocalization. Mol Reprod Dev 61:367–375

    Article  CAS  Google Scholar 

  • Dinan L (2001) Phytoecdysteroids: biological aspects. Phytochemistry 57:325–329

    Article  CAS  Google Scholar 

  • Dinan L, Bourne C, Meng Y, Sarker SD, Tolentino RB, Whiting P (2001a) Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities. Cell Mol Life Sci 58:321–342

    Article  CAS  Google Scholar 

  • Dinan L, Bourne P, Whiting P, Dhadialla TS, Hutchinson TH (2001b) Screening of environmental contaminants for edysteroid agonist and antagonists activity using the Drosophila melanogaster B(II) cell in vitro assay. Environ Toxicol Chem 20:2038–2046

    Article  CAS  Google Scholar 

  • 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 

  • Donahue JK (1940) Occurrence of estrogens in the ovaries of certain invertebrates. Endocrinology 27:149–152

    CAS  Google Scholar 

  • Donahue JK, Jennings EW (1937) The occurrence of estrogenic substances in the ovaries of echinoderm. Endocrinology 21:875–877

    Article  Google Scholar 

  • Durham PJ (1978) Sex pheromones in crustacea. Biol Rev 53:555–583

    Google Scholar 

  • Durica DS, Wu XH, Anilkumar G, Hopkins PM, Chung ACK (2002) Characterization of crab EcR and RXR homologs and expression during limb regeneration and oocyte maturation. Mol Cell Endocrinol 189:59–76

    Article  CAS  Google Scholar 

  • Elmogy M, Iwami M, Sakurai S (2004) Presence of membrane ecdysone receptor in the anterior silk gland of the silkworm Bombyx mori. Eur J Biochem 271:3171–3179

    Article  CAS  Google Scholar 

  • Fairs NJ, Evershed RP, Quinlan PT, Goad LI (1989) Detection of unconjugated and conjugated steroids in the ovary, eggs, and haemolymph of the decapod crustacean Nephrops norvegicus. Gen Comp Endocrinol 74:199–208

    Article  CAS  Google Scholar 

  • Fingerman M (1997) Crustacean endocrinology: a retrospective, prospective and introspective analysis. Physiol Zool 70:257–269

    CAS  Google Scholar 

  • Fingerman M, Nababhushanam K, Sarojini R (1993) Vertebrate-type hormones in Crustaceans, localization, identification and functional significance. Zool Sci 10:13–29

    CAS  Google Scholar 

  • Francke S, Käuser G (1989) Occurrence and hormonal role of ecdysteroids in non-arthropods. In:Koolman J (eds) Ecdysone, from chemistry to mode of action. Georg Thieme Verlag, Stuttgart, pp 296–307

    Google Scholar 

  • Fujimoto Y, Miyasaka S, Ikeda T, Ikekawa N, Ohnishi E, Mizuno T, Watanabe K (1985) An unusual ecdysteroid (20 S)-cholesta-7,14-diene-3β,5α,6α,20,25-pentalol (bombycosterol) from the ovaries of the silkworm, Bombyx mori. J Chem Soc Chem Commun 10–12

  • Fukuzawa A, Kumagai Y, Masamune T, Furusaki A, Katayama C, Matsumoto T (1981) Acetylpinnasterol and pinnasterol, ecdysone-like metabolites from the marine red alga Laurencia pinnata Yamada. Tetrahedron Lett 22:4085–4086

    Article  CAS  Google Scholar 

  • Gaffney J, Goad LJ (1974) Progesterone metabolism by the echinoderm Asterias rubens and Marthasterias glacialis. Biochem J 138:309–311

    CAS  Google Scholar 

  • Gagné F, Blaise C, Pellerin J, Pelletier E, Douville M, Gauthier-Clerc S, Viglino L (2003) Sex alteration in soft-shell clams (Mya arenaria) in an intertidal zone of the Saint Lawrence River (Quebec, Canada). Comp Biochem Physiol C 134:189–198

    Article  Google Scholar 

  • Garcia M, Gharbi J, Girault J-P, Hétru C, Lafont R (1989) Ecdysteroid metabolism in leeches. Invertebr Reprod Dev 15:57–68

    CAS  Google Scholar 

  • Garcia M, Griffond B, Lafont R (1995) What are the origins of ecdysteroids in Gastropods? Gen Comp Endocrinol 97:76–85

    Article  CAS  Google Scholar 

  • Gassman NJ, Kennedy CJ (1992) Cytochrome P-450 content and xenobiotic metabolizing enzyme activities in the scleractinian coral, Favia fragum (Esper). Bull Mar Sci 50:320–330

    Google Scholar 

  • Gauthier-Clerc S, Pellerin J, Amiard JC (2006) Estradiol-17β and testosterone concentrations in male and female Mya arenaria (Mollusca bivalva) during the reproductive cycle. Gen Comp Endocrinol (in press)

  • Ghosh D, Ray AK (1993) 17β-Hydroxysteroid dehydrogenase activity of ovary and hepato-pancreas of Macrobrachium rosenbergii: relation to ovarian condition and estrogen treatment. Gen Comp Endocrinol 89:248–254

    Article  CAS  Google Scholar 

  • Gilbert LI (2004) Halloween genes encode P450 enzymes that mediate steroid hormone biosynthesis in Drosophila melanogaster. Mol Cell Endocrinol 215:1–10

    Article  CAS  Google Scholar 

  • Gissendanner CR, Crossgrove K, Kraus KA, Maina CV, Sluder AE (2004) Expression and function of conserved nuclear receptor genes in Caenorhabditis elegans. Dev Biol 266:399–416

    Article  CAS  Google Scholar 

  • Gooding MP, Wilson VS, Folmar LC, Marcovich DT, LeBlanc GA (2003) The biocide tributyltin reduces the accumulation of testosterone as fatty acid esters in the mud snail (Ilyanassa obsoleta). Environ Health Perspect 111:426–430

    Article  CAS  Google Scholar 

  • Guerriero A, Traldi P, Pietra F (1986) Gerardiasterone, a new ecdysteroid with a 20,22,23,25-tetrahydroxylated side chain from the mediterranean zoanthid Gerardia savaglia. J Chem Soc Chem Commun 40–41

  • Hathaway RR (1965) Conversion of estradiol-17β by sperm preparations of sea urchins and oysters. Gen Comp Endocrinol 5:504–508

    Article  CAS  Google Scholar 

  • Hawkins MB, Thorton JW, Crews D, Skipper JK, Dotte A, Thomas P (2000) Identification of a third distinct estrogen receptor and reclassification of estrogen receptors in teleosts. Proc Natl Acad Sci USA 97:10751–10756

    Article  CAS  Google Scholar 

  • Hines GA, Watts SA, Sower SA, Walker CW (1992a) Sex steroid levels in the testes, ovaries, and pyloric caeca during gametogenesis in the sea star Asterias vulgaris. Gen Comp Endocrinol 87:451–460

    Article  CAS  Google Scholar 

  • Hines GA, Watts SA, Walker CW, Voogt PA (1992b) Androgen metabolism in somatic and gonadal tissues of the sea star Asterias vulgaris. Comp Biochem Physiol B 102:521–526

    Article  CAS  Google Scholar 

  • Hines GA, Watts SA, McClintock JB (1994) Biosynthesis of estrogen derivatives in the echinoid Litechinus variegatus Lamarck. In: David B, Guille A, Feral J-P, Roux M (eds) Echinoderms through time. Balkema, Rotterdam, pp 711–716

    Google Scholar 

  • Homola E, Chang ES (1997) Methyl farnesoate: crustacean juvenile hormone in search of functions. Comp Biochem Physiol B 117:347–356

    Article  Google Scholar 

  • Hsu H-J, Liang M-R, Chen C-T, Chung B-C (2006) Pregnenolone stabilizes microtubules and promotes zebrafish embryonic cell movement. Nature 439:480–483

    Article  CAS  Google Scholar 

  • Hu R, Wu W, Niles EG, Lo Verde PT (2006) Isolation and characterization of Schistosoma mansoni constitutive androstane receptor. Mol Biochem Parasitol 148:31–43

    Article  CAS  Google Scholar 

  • Huberman A (2000) Shrimp endocrinology: a review. Aquaculture 191:191–208

    Article  CAS  Google Scholar 

  • Hutchinson TH (2002) Reproductive and developmental effects of endocrine disrupters in invertebrates: in vitro and in vivo approaches. Toxicol Lett 131:75–81

    Article  CAS  Google Scholar 

  • Idler DR, Sangalang GB, Kanazawa A (1969) Steroid desmolase in gonads of a marine invertebrate, Placopecten magellanicus Gmelin. Gen Comp Endocrinol 12:222–230

    Article  CAS  Google Scholar 

  • Ikegami S (1976) Role of saterosaponin A in starfish spawning induced by gonad-stimulating substance and 1-methyladenine. J Exp Zool 198:359–366

    Article  CAS  Google Scholar 

  • Janer G, LeBlanc GA, Porte C (2005) A comparative study on androgen metabolism in three invertebrate species. Gen Comp Endocrinol 143:211–221

    Article  CAS  Google Scholar 

  • Janer G, Mesia-Vela S, Porte C, Kauffman FC (2004) Esterification of vertebrate-type steroids in the Eastern oyster (Crassostrea virginica). Steroids 69:129–136

    Article  CAS  Google Scholar 

  • Javitt NB (2004) Oxysteroids: a new class of steroids with autocrine and paracrine functions. Trends Endocrinol Metab 15:393–397

    Article  CAS  Google Scholar 

  • Jegla TC (1990) Evidence for ecdysteroids as molting hormones in chelicerata, crustacea, and myriapoda. In: Gupta AP (ed), Morphogenetic hormones of arthropods. vol 1. Rutgers University Press, New Brunswick, NJ, pp 229–273

    Google Scholar 

  • Jeng SS, Wan WC, Chang CF (1978) Existence of an estrogen-like compound in the ovary of the shrimp Parapenaeus fissurus. Gen Comp Endocrinol 36:211–214

    Article  CAS  Google Scholar 

  • Jobling S, Casey D, Rodgers-Gray T, Oehlmann J, Schulte-Oehlmann U, Pawlowski S, Baunbeck T, Turner AP, Tyler CR (2004) Comparative responses of molluscs and fish to environmental estrogens and an estrogenic effluent. Aquat Toxicol 66:207–222

    Article  CAS  Google Scholar 

  • Kajiwara M, Kuraku S, Kurokawa T, Kato K, Toda S, Hirose H, Takahashi S, Shibata Y, Iguchi T, Matsumoto T, Miyata T, Miura T, Takahashi Y (2006) Tissue preferential expression of estrogen receptor gene in the marine snail Thais clavigera. Gen Comp Endocrinol 148:315–326

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Kaloyianni M, Stamatiou R, Dalianis S (2005) Zinc and 17β-estradiol induce modifications in Na+/H+ exchanger and pyruvate kinase activity through protein kinase C in isolated mantle/gonad cells of Mytilus galloprovincialis. Comp Biochem Physiol C 141C:257–266

    CAS  Google Scholar 

  • Karlson P (1983) Eighth Adolf Butenandt Lecture. Why are so many hormones steroids? Hoppe Seylers Z Physiol Chem 364(Suppl):1067–1087

    CAS  Google Scholar 

  • Kashian DR, Dodson SI (2004) Effect of vertebrate hormones on development and sex determination in Daphnia magna. Environ Toxicol Chem 23:1282–1288

    Article  CAS  Google Scholar 

  • 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 

  • Kicha AA, Ivanchina NV, Stonik VA (2003) Seasonal variations in the levels of polyhydroxysteroids and related glycosides in the digestive tissues of the starfish Patiria (-Asterina) pectinifera. Comp Biochem Physiol B 136:897–903

    Article  CAS  Google Scholar 

  • Keay J, Bridgham JT, Thornton JW (2006) The Octopus vulgaris estrogen receptor is a constitutive transcriptional activator: evolutionary and functional implications. Endocrinology 147:3861–3869

    Article  CAS  Google Scholar 

  • Kim H-W, Chang ES, Mykles DL (2005) Three calpains and ecdysone receptor in the land crab Gecarcinus lateralis: sequences, expression and effects of elevated ecdysteroid induced by eyestalk ablation. J Exp Biol 208:3177–3197

    Article  CAS  Google Scholar 

  • Kime DE (1987) The steroids. In: Chester-Jones I, Ingleton PM, Phillips JG (eds) Fundamentals of vertebrate endocrinology. Plenum Press, New York, pp 3–56

    Google Scholar 

  • Kime DE (1993) Classical and non-classical reproductive steroids in fish. Rev Fish Biol Fish 3:160–180

    Article  Google Scholar 

  • Kittredge JS, Terry M, Takahashi FT (1971) Sex pheromone activity of the moulting hormone, crustecdysone, on male crabs. Fish Bull Calif 69:337–343

    Google Scholar 

  • Koskela RW, Greenwood JG, Rothlisberg PC (1992) The influence of prostaglandin E2 and the steroid hormones, 17α-hydroxyprogesterone and 17β-estradiol on moulting and ovarian development in the tiger prawn, Penaeus esculentus Haswell, 1879 (Crustacea: Decapoda). Comp Biochem Physiol A 101:295–299

    Article  Google Scholar 

  • Kretschmer XC, Baldwin WS (2005) CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact 155:111–128

    Article  CAS  Google Scholar 

  • Kurzchalia TV, Ward S (2003) Why do worms need cholesterol? Nature Cell Biol 5:684–688

    Article  CAS  Google Scholar 

  • Lachaise F (1990) Synthesis, metabolism, and effects on molting of ecdysteroids in Crustacea, Chelicerata, and Myriapoda. In: Gupta AP (ed) Morphogenetic hormones of arthropods, vol 1. Rutgers University Press, New Brunswick, NJ, pp 275–323

    Google Scholar 

  • Lachaise F, Le Roux A, Hubert M, Lafont R (1993) The molting gland of crustaceans: localization, activity and endocrine control. J Crustacean Biol 13:198–234

    Article  Google Scholar 

  • Lafont R (1991) Reverse endocrinology, or “hormones” seeking functions. Insect Biochem 21:697–721

    Article  CAS  Google Scholar 

  • Lafont R (1997) Ecdysteroids and related molecules in animals and plants. Arch Insect Biochem Physiol 35:3–20

    Article  CAS  Google Scholar 

  • Lafont R (2000) The endocrinology of invertebrates. Ecotoxicology 9:42–57

    Article  Google Scholar 

  • Lafont R, Dinan L (2003) Practical uses for ecdysteroids in Mammals and Humans: an update. J Insect Sci 3:7. http://www.insectscience.org/3.7/

  • Lafont R, Connat JL, Delbecque JP, Porcheron P, Dauphin-Villemant C, Garcia M (1995) Comparative studies on ecdysteroids. In: Ohnishi E, Sonobe H Takahashi SY (eds) Recent advances in insect biochemistry and molecular biology. University of Nagoya Press, Nagoya, pp 45–91

    Google Scholar 

  • Lafont R, Dauphin-Villemant C, Warren JT, Rees HH (2005) Ecdysteroid chemistry and biochemistry. In: Gilbert LI, Iatrou K, Gill SS (eds) Comprehensive molecular insect science. vol 3, Elsevier/Pergamon, Amsterdam, pp 125–195

    Google Scholar 

  • Lanot R, Clédon P (1989) Ecdysteroids and meiotic reinitiation in Palæmon serratus (Crustacea Decapoda Natantia) and in Locusta migratoria (Insecta Orthoptera). A comparative study. Invertebr Reprod Dev 16:169–175

    CAS  Google Scholar 

  • Lathe R (2002) Steroid and sterol 7-hydroxylation: ancient pathways. Steroids 67:967–977

    Article  CAS  Google Scholar 

  • Laufer H, Borst DW, Foley TA, Landau M (1988) Ecdysteroid titers in vitellogenic Libinia emarginata. J Insect Physiol 34:615–617

    Article  CAS  Google Scholar 

  • Laufer H, Ahl J, Rotllant G, Baclaski B (2002) Evidence that ecdysteroids and methyl farnesoate control allometric growth and differentiation in a crustacean. Insect Biochem Mol Biol 32:205–210

    Article  CAS  Google Scholar 

  • Laurent P, Braekman J-C, Daloze D, Pasteels JM (2003) An ecdysteroid (22-acetyl-20-hydroxyecdysone) from the defense gland secretion of an insect: Chrysolina carnifex (Coleoptera: Chrysomelidae). ChemoEcology 13:109–111

    Article  CAS  Google Scholar 

  • LeBlanc GA, McLachlan JB (1999) Molt-independent growth inhibition of Daphnia magna by vertebrate antiandrogen. Environ Toxicol Chem 18:1450–1455

    Article  CAS  Google Scholar 

  • Le Curieux-Belfond O, Moslemi S, Mathieu M, Séralini GE (2001) Androgen metabolism in oyster Crassostrea gigas: evidence for 17β-HSD activities and characterization of an aromatase-like activity inhibited by pharmacological compounds and a marine pollutant. J Steroid Biochem Mol Biol 78:359–366

    Article  CAS  Google Scholar 

  • Le Curieux-Belfond O, Fievet B, Séralini GE, Mathieu M (2005) Short-term bioaccumulation, circulation and metabolism of estradiol-17β in the oyster Crassostrea gigas. J Exp Mar Biol Ecol 325:125–133

    Article  CAS  Google Scholar 

  • Lehoux J-G, Sandor T (1970) The occurrence of steroids and steroid-metabolizing systems in invertebrates: a review. Steroids 16:141–171

    Article  CAS  Google Scholar 

  • Li Q, Osada M, Suzuki T, Mori K (1998) Changes in vitellin during oogenesis and effect of estradiol 17β on vitellogenesis in the Pacific oyster Crassostrea gigas. Invertebr Reprod Dev 33:87–93

    Google Scholar 

  • Liebig M, Egeler P, Oehlmann J, Knacker T (2005) Bioaccumulation of 14C-17α-ethinylestradiol by the aquatic oligochaete Lumbriculus variegatus in spiked artificial sediment. Chemosphere 59:271–280

    Article  CAS  Google Scholar 

  • Lockyer AE, Noble LR, Rollinson D, Jones CS (2005) Isolation and characterization of the full-length cDNA encoding a member of a novel cytochrome p450 family (CYP320A1) from the tropical freshwater snail Biomphalaria glabrata, intermediate host for Schistosoma mansoni. Mem Inst Oswaldo Cruz 100:259–262

    Article  CAS  Google Scholar 

  • Mackevieciene G, Chibisova N (1995) Concentration of steroid hormones at different stages of the intermoult cycle in the crayfish Astacus astacus and Pacifastacus leniusculus. Freshw Crayfish 10:267–273

    Google Scholar 

  • Mackie AM, Singh HT, Turner AB (1977) Studies on distribution, biosynthesis and function of steroidal saponins in echinoderms. Comp Biochem Physiol B 56:9–14

    Article  CAS  Google Scholar 

  • Mao H, Kaufman WR (1998) DNA binding properties of the ecdysteroid receptor in the salivary gland of the female ixodid tick, Amblyomma hebraeum. Insect Biochem Mol Biol 28:947–957

    Article  CAS  Google Scholar 

  • Matsumoto T, Osada M, Osawa Y, Mori K (1997) Gonadal estrogen profile and immunohistochemical localization of steroidogenic enzymes in the oyster and scallop during sexual maturation. Comp Biochem Physiol B 118:811–817

    Article  Google Scholar 

  • Matsumoto T, Nakamura AM, Mori K, Kayano T (2003) Molecular characterization of a cDNA encoding putative vitellogenin from the Pacific oyster Crassostrea gigas. Zool Sci 20:37–42

    Article  CAS  Google Scholar 

  • Matyash V, Entchev EV, Mende F, Wilsch-Bräuninger M, Thiele C, Schmidt AW, Knölker H-J, Ward S, Kurzchalia TV (2004) Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16. PloS Biol 2:1561–1571

    Article  CAS  Google Scholar 

  • Meane S (2005) Is C-26 hydroxylation an evolutionarily conserved steroid inactivation mechanism? FASEB Journal 19:1220–1224

    Article  CAS  Google Scholar 

  • Meinwald J, Huang Q, Vrkoc J, Herath KB, Yang Z-C, Schröder F, Attygalle AB, Iyengar VK, Morgan RC, Eisner T (1998) Mirasorvone: a masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus). Proc Natl Acad Sci USA 95:2733–2737

    Article  CAS  Google Scholar 

  • Mellon SH, Griffin LD (2002) Neurosteroids: biochemistry and clinical significance. Trends Endocrinol Metab 13:35–43

    Article  CAS  Google Scholar 

  • Miller JR Mumma RO (1973) Defensive agents of the american water beetles Agabus seriatus and Graphoderus liberus. J Insect Physiol 19:917–925

    Article  Google Scholar 

  • Morcillo Y, Ronis MJJ, Solé M Porte C (1998) Effects of tributyltin on the cytochrome P450 monooxygenase system and sex steroid metabolism in the clam Ruditapes decussata. Mar Environ Res 46:583–586

    Article  CAS  Google Scholar 

  • Mori K, Tamate H, Imai T (1966) Histochemical study on the change of 17β-hydroxysteroid dehydrogenase activity in the oyster during the stages of sexual maturation and spawning. Tohoku J Agri Res 17:179–187

    CAS  Google Scholar 

  • Mori K, Muramatsu T, Nakamura Y (1969) Effect of steroids: III. Sex reversal from male to female in Crasssostrea gigas by estradiol-17β. Bull Japan Soc Sci Fish 35:1072–1076

    CAS  Google Scholar 

  • Morrison DD, van de Waa EA, Bennett JL (1986) Effect of steroids and steroid synthesis inhibitors on the fecundity of Schistosoma mansoni in vitro. J Chem Ecol 12:1901–1908

    Article  CAS  Google Scholar 

  • Moss SM (1989) Effects of exogenous androgens on growth, biochemical composition and reproduction of the coot clam Mulinia lateralis. Pac Sci 43:200

    Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Mouneyrac C, Pellerin J, Moukrim A, Ait Alla A, Duron C, Viault N (2006). In situ relationship between energy reserves and steroid hormone levels in Nereis diversicolor (O.F. Müller) from clean and contaminated sites. Ecotoxicol Environ Saf (in press)

  • Mu X, LeBlanc GA (2002) Developmental toxicity of testosterone in the crustacean Daphnia magna involves anti-ecdysteroidal activity. Gen Comp Endocrinol 129:127–133

    Article  CAS  Google Scholar 

  • Nadal A, Ropero AB, Fuentes E, Soria B, Ripoll C (2004) Estrogen and xenoestrogen actions on endocrine pancreas: from ion channel modulation to activation of nuclear function. Steroids 69:531–536

    Article  CAS  Google Scholar 

  • Nagabushanam R, Kulkarni GK (1981) Effect of exogenous testosterone on the androgenic gland and testis of a marine penaeid prawn, Parapenaeopsis hardwickii (Miers) (Crustacea, Decapoda, Penaeidae). Aquaculture 23:19–27

    Article  Google Scholar 

  • Nagahama Y (1997) 17α,20β-Dihydroxy-4-pregnen-3-one, a maturation-inducing hormone in fish oocytes: mechanisms of synthesis and action. Steroids 62:190–196

    Article  CAS  Google Scholar 

  • Nishikawa J-I, Mamiya S, Kanayama T, Nishikawa T, Shiraishi F, Horiguchi T (2004) Involvement of the Retinoid X receptor in the development of imposex caused by organotins in Gastropods. Environ Sci Technol 38:6271–6276

    Article  CAS  Google Scholar 

  • Nolte A, Koolman J, Dörlochter M, Straub H (1986) Ecdysteroid in the dorsal bodies of Pulmonates (Gastropoda): synthesis and release of ecdysone. Comp Biochem Physiol A 84:777–782

    Article  Google Scholar 

  • Norman AW, Mizwicki MT, Norman DPG (2004) Steroid-hormone rapid actions, membrane receptors and a conformational ensemble model. Nat Rev 3:27–41

    CAS  Google Scholar 

  • Novak FJS, Lambert JGD (1989) Progesterone, testosterone and estradiol in the migratory locust Locusta migratoria; a gas chromatographical-mass spectrometrical study. Gen Comp Endocrinol 76:73–82

    Article  CAS  Google Scholar 

  • Novak F, Van Beek E, Lambert J, De Loof A (1990) Pregnenolone and estradiol identification in the brine shrimp, Artemia sp., by means of gas-chromatographical-mass spectrometrical analysis. Comp Biochem Physiol B 95:565–568

    Article  Google Scholar 

  • Oberdörster E, Clay MA, Cottam DM, Wilmot FA, McLachlan JA, Milner MJ (2001) Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. J Steroid Biochem Mol Biol 77:229–238

    Article  Google Scholar 

  • Oehlmann J, Bettin C (1996) TBT-induced imposex and the role of steroids in marine snails. Malacol Rev 6:157–161

    Google Scholar 

  • Oehlmann J, Schulte-Oehlmann U (2003) Endocrine disruption in invertebrates. Pure Appl Chem 75:2207–2218

    CAS  Google Scholar 

  • Oetken M, Bachmann J, Schulte-Oehlmann U, Oehlmann J (2004) Evidence for endocrine disruption in invertebrates. Int Rev Cytol 236:1–44

    CAS  Google Scholar 

  • Okazaki RK, Snyder MJ, Chang ES (1988) Ecdysteroids in nemerteans: presence and physiological role. Hydrobiologia 156:153–160

    Article  CAS  Google Scholar 

  • Okumura T, Han CH, Suzuki Y, Aida K, Hanyu I (1992) Changes in hemolymph vitellogenin and ecdysteroid levels during the reproductive and non-reproductive molt cycles in the freshwater prawn, Macrobrachium nipponense. Zool Sci 9:37–45

    CAS  Google Scholar 

  • Ollevier F, De Clerck D, Diederick H, De Loof A (1986) Identification of nonecdysteroid steroids in hemolymph of both male and female Astacus leptodactylus (Crustacea) by gas chromatography-mass spectrometry. Gen Comp Endocrinol 61:214–218

    Article  CAS  Google Scholar 

  • Oppermann UCT, Maser E, Hermans JJR, Koolman J, Netter KJ (1992) Homologies between enzymes involved in steroid and xenobiotic carbonyl reduction in vertebrates, invertebrates and procaryonts. J Steroid Biochem Mol Biol 43:665–675

    Article  CAS  Google Scholar 

  • Osada M, Nomura T (1989) Estrogen effect on the seasonal levels of catecholamines in the scallop Patinopecten yessoensis. Comp Biochem Physiol 93:349–353

    Google Scholar 

  • Osada M, Mori K, Nomura Y (1992a) In vitro effects of estrogen and serotonin on release of eggs from the ovary of the scallop. Nippon Suisan Gakkai Shi 58:223–227

    CAS  Google Scholar 

  • Osada M, Unuma T, Mori K (1992b) Purification and characterization of a yolk protein from the scallop ovary. Nippon Suisan Gakkai Shi 58:2283–2289

    CAS  Google Scholar 

  • Osada M, Takamura T, Sato H, Mori K (2003) Vitellogenin synthesis in the ovary of scallop, Patinopecten yessoensis: control by estradiol-17β and the central nervous system. J Exp Zool 299A:172–179

    Article  CAS  Google Scholar 

  • Osada M, Tawarayama H, Mori K (2004) Estrogen synthesis in relation to gonadal development of Japanese scallop, Patinopecten yessoensis: gonadal profile and immunolocalization of P450 aromatase and estrogen. Comp Biochem Physiol B 139:123–128

    Article  CAS  Google Scholar 

  • Panter GH, Thompson RS, Beresford N, Sumpter JP (1999) Transformation of a non-oestrogenically active substance by minimal bacterial activity. Chemosphere 38:3579–3596

    Article  CAS  Google Scholar 

  • Paolucci M (2002) Progesterone receptor: an evolutionary perspective. Trends Comp Biochem Physiol 9:185–190

    CAS  Google Scholar 

  • Paolucci M, Di Cristo C, Di Cosmo A (2002) Immunological evidence for progesterone and estradiol receptors in the freshwater crayfish Austropotamobius pallipes. Mol Reprod Dev 63:55–62

    Article  CAS  Google Scholar 

  • Payne AH, Hales DB (2004) Overview of steroidogenic enzymes in the pathway from cholesterol to active steroid hormones. Endocr Rev 25:947–970

    Article  CAS  Google Scholar 

  • Pernet V, Anctil M (2002) Annual variations and sex-related differences in estradiol-17β levels in the Anthozoan Renilla koellikeri. Gen Comp Endocrinol 129:63–68

    Article  CAS  Google Scholar 

  • Pollio A, Pinto G, Della Greca M, Di Maio A, Fiorentino A, Previtera L (1994) Progesterone bioconversion by microalgal cultures. Phytochemistry 37:1269–1272

    Article  CAS  Google Scholar 

  • 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-Verlag, Berlin, pp 346–348

    Google Scholar 

  • Pounds NA, Hutchinson TH, Williams TD, Whiting P, Dinan L (2002) Assessment of putative endocrine disrupters in an in vivo crustacean assay and an in vitro insect assay. Mar Environ Res 54:709–713

    Article  CAS  Google Scholar 

  • Prokof’eva NG, Chaikina EL, Kicha AA, Ivanchina NV (2003) Biological activities of steroid glycosides from starfish. Comp Biochem Physiol B 134:695–701

    Article  CAS  Google Scholar 

  • Qi J, Ojika M, Sakagami Y (2002) Linckosides A and B, two new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorg Med Chem 10:1961–1966

    Article  CAS  Google Scholar 

  • Qi J, Ojika M, Sakagami Y (2004) Linckosides C-E, three new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorg Med Chem 12:4259–4265

    Article  CAS  Google Scholar 

  • Quinitio ET, Hara A, Yamauchi K, Nakao S (1994) Changes in the steroid hormone and vitellogenin levels during the gametogenic cycle of the giant tiger shrimp, Penaeus monodon. Comp Biochem Physiol C 109:21–26

    Google Scholar 

  • Reis-Henriques MA, Coimbra J (1990) Variations in the levels of progesterone in Mytilus edulis during the annual reproductive cycle. Comp Biochem Physiol A 95:343–348

    Article  Google Scholar 

  • Reis-Henriques MA, Le Guellec D, Rémy-Martin JP, Adessi GL (1990) Studies on endogenous steroids from the marine mollusc Mytilus edulis L. by gas chromatography and mass spectrometry. Comp Biochem Physiol B 95:303–309

    Article  Google Scholar 

  • Remoué F, Mani J-C, Pugnière M, Schacht A-M, Capron A, Riveau G (2002) Functional specific binding of testosterone to Schistosoma hematobium 20-kilodalton glutathione S-transferase. Infect Immun 70:601–605

    Article  CAS  Google Scholar 

  • Revankar CM, Cimino DF, Sklar LA, Arterburn JB, Prossnitz ER (2005) A transmembrane intracellular estrogen receptor mediates rapid cell signaling. Science 307:1625–1630

    Article  CAS  Google Scholar 

  • Rewitz KF, Styrishave B, Lobner-Olesen A, Andersen O (2006) Membrane invertebrate cytochrome P450: emerging insights from vertebrate and insect analogies. Comp Biochem Physiol C 143:636–381

    Google Scholar 

  • Roepke TA, Snyder MJ, Cherr GN (2005) Estradiol and endocrine disrupting compounds adversely affect development of sea urchin embryos at environmentally relevant concentrations. Aquat Toxicol 71:155–173

    Article  CAS  Google Scholar 

  • Ronis MJJ, Mason AZ (1996) The metabolism of testosterone by the periwinckle (Littorina littorea) in vitro and in vivo: effects of tributyltin. Mar Environ Res 42:161–166

    Article  CAS  Google Scholar 

  • Rothschild M, Ford B (1966) Hormones of the vertebrate host controlling ovarian regression and copulation of the rabbit flea. Nature 211:261–266

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Sagi A, Karp L, Milner Y, Cohen D, Kuris AM, Chang ES (1991) Testicular thymidine incorporation in the prawn Macrobrachium rosenbergii: molt cycle variation and ecdysteroid effects in vitro. J Exp Zool 259:229–237

    Article  CAS  Google Scholar 

  • Sandor T (1981) Steroids in invertebrates. In: Clark WH Jr, Adams TS (eds) Advances in invertebrate reproduction. Elsevier/North-Holland, New York, pp 81–96

    Google Scholar 

  • Santos MM, Castro LFC, Vieira MN, Micael J, Morabito R, Massanisso P, Reis-Henriques MA (2005) New insights into the mechanism of imposex induction in the dogwhelk Nucella lapillus. Comp Biochem Physiol C 141:101–109

    CAS  Google Scholar 

  • Sauber F, Reuland M, Berchtlod J-P, Hétru C, Tsoupras G, Luu B, Moritz M-E, Hoffmann JA (1983) Cycle de mue et ecdystéroïdes chez une Sangsue, Hirudo medicinalis. C R Acad Sci III 296:413–418

    CAS  Google Scholar 

  • Schaaf O, Dettner K (2000) Transformation of steroids by Bacillus strains isolated from the foregut of water beetles (Coleoptera: Dytiscidae): II. Metabolism of 3β-hydroxypregn-5-en-20-one (pregnenolone). J Steroid Biochem Mol Biol 75:187–199

    Article  CAS  Google Scholar 

  • Schaaf O, Baumgarten J, Dettner K (2000) Identification and function of prothoracic exocrine gland steroids of the Dysticid beetles Graphoderus cinereus and Laccophilus minutus. J Chem Ecol 26:2291–2305

    Article  CAS  Google Scholar 

  • Schallig HDFH, Glasmeier A, de Jong-Brink M (1992) Vertebrate-type steroids in cercariae of the Schistosome Trichobilharzia ocellata. Parasitol Res 78:709–711

    Article  Google Scholar 

  • Schildknecht H (1970) The defensive chemistry of land and water beetles. Angew Chem, Int Ed 9:1–9

    Article  CAS  Google Scholar 

  • Schoenmakers HJN (1979) In vitro biosynthesis of steroids from cholesterol by the ovaries and pyloric caeca of the starfish Asterias rubens. Comp Biochem Physiol B 63:179–184

    Article  Google Scholar 

  • Schoenmakers HJN (1981) The possible role of steroids in vitellogenesis in the starfish Asterias rubens. In: Clark WH Jr, Adams TS (eds) Advances in invertebrate reproduction. Elsevier/North-Holland, New York, pp 127–150

    Google Scholar 

  • Schoenmakers HJN, Dieleman SJ (1981) Progesterone and estrone levels in the ovaries, pyloric caeca, and perivisceral fluid during the annual reproductive cycle of starfish, Asterias rubens. Gen Comp Endocrinol 43:63–70

    Article  CAS  Google Scholar 

  • Schoenmakers HJN, Voogt PA (1980) In vitro biosynthesis of steroids from progesterone by the ovaries and pyloric caeca of the starfish Asterias rubens. Gen Comp Endocrinol 41:408–416

    Article  CAS  Google Scholar 

  • Schoenmakers HJN, Voogt PA (1981) In vitro biosynthesis of steroids from androstenedione by the ovaries and pyloric caeca of the starfish, Asterias rubens. Gen Comp Endocrinol 45:242–248

    Article  CAS  Google Scholar 

  • Schoenmakers HJN, Van Bohemen CG, Dieleman SJ (1981) Effect of estradiol-17β on the ovaries of the starfish Asterias rubens. Dev Growth Differ 23:125–135

    Article  CAS  Google Scholar 

  • Schoner W (2002) Endogenous cardiac glycosides, an new class of steroid hormones. Eur J Biochem 269:2440–2448

    Article  CAS  Google Scholar 

  • Schroepfer GJ Jr (2000) Oxysterols: modulators of cholesterol metabolism and other processes. Physiol Rev 80:361–554

    CAS  Google Scholar 

  • Searle PA, Molinski TF (1995) 4-Dehydroecdysterone, a new ecdysteroid from the zoanthid Parazoanthus sp. J Nat Prod 58:264–268

    Article  CAS  Google Scholar 

  • Shafqat N, Marschall H-U, Filling C, Nordling E, Wu X-Q, Björk L, Thyberg J, Mårtensson E, Salim S, Jörnvall H, Oppermann U (2003) Expanded susbtrate screenings of human and Drosophila type10 17β-hydroxysteroid dehydrogenases (HSDs) reveal multiple specificities in bile acid and steroid hormone metabolism: characterization of multifunctional 3α/7α/7β/17β/20β/21-HSD. Biochem J 376:49–60

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Shih J-T, Liao C-F (1998) Conversion of cholesterol to sex steroid-like substances by tissues of Mictyris brevidactylus in vitro. Zool Stud 37:102–110

    CAS  Google Scholar 

  • Shih J-T, Tseng S-S (1999) Progesterone-like substance in ovary and hepatopancreas of Uca vocans borealis. Zool Stud 38:458–465

    CAS  Google Scholar 

  • Shubina LK, Fedorov SN, Levina EV, Andriyaschenko PV, Kalinovsky AI, Stonik VA, Smirnov IS (1998) Comparative study on polyhydroxylated steroids from echinoderms. Comp Biochem Physiol B 119:505–511

    Article  Google Scholar 

  • Siah A, Pellerin J, Benosman A, Gagné JP, Amiard JC (2002) Seasonal gonad progesteron pattern in the soft-shell clam Mya arenaria. Comp Biochem Physiol A 132:499–511

    Article  CAS  Google Scholar 

  • Slattery M, Hines GA, Starmer J, Paul VJ (1999) Chemical signals in gametogenesis, spawning, and larval settlement and defense of the soft coral Sinularia polydactyla. Coral Reefs 18:75–84

    Article  Google Scholar 

  • Smith AG, Goad LJ (1971) Metabolism of cholesterol in the enchinoderms Asterias rubens and Solaster papposus. FEBS Lett 12:233–235

    Article  CAS  Google Scholar 

  • Snyder MJ, Okazaki RK, Chang ES (1992) Nemertean ecdysteroids: relationship to reproduction. Invertebr Reprod Dev 21:7–13

    CAS  Google Scholar 

  • Spencer M, Case JF (1984) Exogenous ecdysteroids elicit low threshold sensory responses in spiny lobsters. J Exp Zool 229:163–166

    Article  CAS  Google Scholar 

  • Spindler K-D (1988) Parasites and hormones. In: Mehlhorn H (ed) Parasitology in focus—facts and trends. Springer-Verlag, Berlin, pp 465–476

    Google Scholar 

  • Spindler K-D (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 

  • Spooner N, Gibbs P, Bryan G, Goad L (1991) The effects of tributyltin upon steroid titres in the female dog-whelk, Nucella lapillus, and the development of imposex. Mar Environ Res 32:37–49

    Article  CAS  Google Scholar 

  • Srivastava DP, Yu EJ, Kennedy K, Chatwin H, Reale V, Hamon M, Smith T, Evans PD (2005) Rapid, nongenomic responses to ecdysteroids and catecholamines mediated by a novel Drosophila G-protein-coupled receptor. J Neurosci 25:6145–6155

    Article  CAS  Google Scholar 

  • Stefano GB, Cadet P, Mantione K, Cho JJ, Jones D, Zhu W (2003) Estrogen signaling at the cell surface coupled to nitric oxide release in Mytilus edulis nervous system. Endocrinology 144:1234–1240

    Article  CAS  Google Scholar 

  • Sturaro A, Guerriero A, De Clause R, Pietra F (1982) A new, unexpected marine source of a molting hormone. Isolation of ecdysterone in large amounts from the zoanthid Gerardia savaglia. Experientia 38:1184–1185

    Article  CAS  Google Scholar 

  • Subramoniam T (2000) Crustacean ecdysteroids in reproduction and embryogenesis. Comp Biochem Physiol C 125:135–156

    CAS  Google Scholar 

  • Suganthi AS, Anilkumar G (1999) Moult-related fluctuation in ecdysteroid titre and spermatogenesis in the crab, Metopograpsus messor (Brachyura: Decapoda). Zool Stud 38:314–321

    Google Scholar 

  • Suksamrarn A, Jankam A, Tarnchompoo B, Putchakarn S (2002) Ecdysteroids from a Zoanthus sp. J Nat Prod 65:1194–1197

    Article  CAS  Google Scholar 

  • Summavielle T, Rocha Monteiro PR, Reis-Henriques MA, Coimbra J (2003) In vitro metabolism of steroid hormones by ovary and hepatopancreas of the crustacean peneid shrimp Marsupenaeus japonicus. Sci Mar (Barcelona) 67:299–306

    Google Scholar 

  • Summavielle T, Silva L, Reis-Henriques MA, Baldaia L, Coimbra J (1995) Hemolymph unconjugated and conjugated steroids during reproduction in Penaeus japonicus (Crustacea Decapoda). Neth J Zool 45:64–67

    Article  Google Scholar 

  • Suzuki T, Hara A, Yamaguchi K, Mori K (1992) Purification and immunolocalization of a vitellin-like protein from the Pacific oyster Crassostrea gigas. Mar Biol 113:239–245

    CAS  Google Scholar 

  • Swevers L, Lambert JGD, De Loof A (1991a) Synthesis and metabolism of vertebrate-type steroids by tissues of insects, a critical evaluation. Experientia 47:687–698

    Article  CAS  Google Scholar 

  • Swevers L, Lambert JGD, De Loof A (1991b) Metabolism of vertebrate-type steroids by tissues of three crustacean species. Comp Biochem Physiol B 99:35–41

    Article  Google Scholar 

  • Takahashi N, Kanatani H (1981) Effect of 17β-estradiol on growth of oocytes in cultured ovarian fragments of the starfish, Asterina pectinifera. Dev Growth Differ 23:565–569

    Article  Google Scholar 

  • Tarrant AM (2005) Endocrine-like signaling in Cnidarians: current understanding and implications for ecophysiology. Integr Comp Biol 45:201–214

    Article  CAS  Google Scholar 

  • Tarrant AM, Atkinson MJ, Atkinson S (2001) Uptake of estrone from the water column by a coral community. Mar Biol 139:321–325

    Article  CAS  Google Scholar 

  • Tarrant AM, Atkinson S, Atkinson MJ (1999) Estrone and estradiol-17β concentration in tissue of the scleractinian coral, Montipora verrucosa. Comp Biochem Physiol A 122:85–92

    Article  CAS  Google Scholar 

  • Tarrant AM, Atkinson MJ, Atkinson S (2004) Effect of steroidal estrogens on coral growth and reproduction. Mar Ecol Prog Ser 269:121–129

    CAS  Google Scholar 

  • Tarrant AM, Blomquist CH, Lima PH, Atkinson MJ, Atkinson S (2003) Metabolism of estrogens and androgens by scleractinian corals. Comp Biochem Physiol B 136:473–485

    Article  CAS  Google Scholar 

  • Teshima S-I, Kanazawa A (1971). Bioconversion or progesterone by the ovaries of the crab, Portunus trituberculatus. Gen Comp Endocrinol 17:152–157

    Article  CAS  Google Scholar 

  • Thiboutot D, Jabara S, McAllister JM, Sivarajah A, Gilligand K, Cong Z, Clawson G (2003) Human skin is a steroidogenic tissue: steroidogenic enzymes and cofactors are expressed in epidermis, normal sebocytes, and an immortalized sebocyte cell line (SEB-A). J Investig Dermatol 120:905–914

    Article  CAS  Google Scholar 

  • 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

    CAS  Google Scholar 

  • Thornton JW, Need E, Crews D (2003) Resurrecting the ancestral steroid receptor: ancient origin of estrogen signaling. Sci 301:1714–1717

    Article  CAS  Google Scholar 

  • Thummel CS, Chory J (2002) Steroid signaling in plants and insects—common themes, different pathways. Genes Dev 16:3113–3129

    Article  CAS  Google Scholar 

  • Tomaschko KH (1994) Ecdysteroids from Pycnogonum litorale (Arthropoda, Pantopoda) act as a chemical defense against Carcinus mænas (Crustacea, Decapoda). J Chem Ecol 20:1445–1455

    Article  CAS  Google Scholar 

  • Tomaschko KH (1999) Nongenomic effect of ecdysteroids. Arch Insect Biochem Physiol 41:89–98

    Article  CAS  Google Scholar 

  • Tominaga N, Ura K, Kawakami M, Kawaguchi T, Kohra S, Mitsui Y, Iguchi T, Arizono K (2003) Caenorhabditis elegans responses to specific steroid hormones. J Health Sci 49:28–33

    Article  CAS  Google Scholar 

  • Twan W-H, Hwang J-S, Chang C-F (2003) Sex steroids in scleractinian coral, Euphyllia ancora: implication in mass spawning. Biol Reprod 68:2255–2260

    Article  CAS  Google Scholar 

  • Van Beek E, De Loof A (1988) Radioimmunological determinations of concentrations of six C21, C19 and C18 steroids during the reproductive cycle of female Artemia sp. (Crustacea, Anostraca). Comp Biochem Physiol A 89:595–599

    Google Scholar 

  • Van der Plas AJ, Koenderman AHL, Deibel-Van Schijndel GJ, Voogt PA (1982) Effect of oestradiol-17β on the synthesis of RNA, proteins and lipids in the pyloric caeca of the female starfish Asterias rubens. Comp Biochem Physiol B 73:965–970

    Article  Google Scholar 

  • Veitia RA, Hurst LD (2001) Accelerated molecular evolution of insect orthologues of ERG28/C14orf1: a link with ecdysteroid metabolism? J Genet 80:17–21

    CAS  Google Scholar 

  • Venkatachalam KV (2005) Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey. BioEssays 27:222–228

    Article  CAS  Google Scholar 

  • Verjovski-Almeida S, DeMarco R, Martins EAL, Guimaraes PEM, Ojopi EPB et al (2003) Transcriptome analysis of the acoelomate human parasite Schistosoma mansoni. Nat Genet 35:148–157

    Google Scholar 

  • Verslycke T, De Wasch K, De Brabander HF, Janssen CR (2002) Testosterone metabolism in the estuarine mysid Neomysis integer (Crustacea; Mysidacea): identification of testosterone metabolites and endogenous Vertebrate-type steroids. Gen Comp Endocrinol 126:190–199

    Article  CAS  Google Scholar 

  • Voogt PA, Dieleman SJ (1984) Progesterone and oestrone levels in the gonad and pyloric caeca of the male sea star Asterias rubens: a comparison with the corresponding levels in the female sea star. Comp Biochem Physiol A 79:635–639

    Article  Google Scholar 

  • Voogt PA, den Besten PJ, Jansen M (1990) The Δ5-pathway in steroid metabolism in the sea star Asterias rubens L. Comp Biochem Physiol B 97:555–562

    Article  Google Scholar 

  • Voogt PA, Oudejans RCHM, Broertjes JJS (1984) Steroids and reproduction in starfish. In: Engels W, et al (eds) Advances in invertebrate reproduction 3. Elsevier Science Publishers B.V., Amsterdam, pp 151–161

    Google Scholar 

  • Wang C, Croll RP (2004) Effects of sex steroids on gonadal development and gender determination in the sea scallop, Placopecten magellanicus. Aquaculture 238:483–498

    Article  CAS  Google Scholar 

  • Warren JT, Dai J-D, Gilbert LI (1999) Can the insect nervous system synthesize ecdysteroids? Insect Biochem Mol Biol 29:571–579

    Article  CAS  Google Scholar 

  • Warrier SR, Tirumalai R, Subramoniam T (2001) Occurrence of vertebrate steroids, estradiol 17β and progesterone in the reproducing females of the mud crab Scylla serrata. Comp Biochem Physiol A 130:283–294

    Article  CAS  Google Scholar 

  • Wasson KM, Watts SA (2000) Progesterone metabolism in the ovaries and testes of the echinoid Lytechinus variegatus Lamarck (Echinodermata). Comp Biochem Physiol C 127:263–272

    CAS  Google Scholar 

  • Wasson KM, Gower BA, Hines GA, Watts SA (2000a) Levels of progesterone, testosterone and estradiol, and androstenedione metabolism in the gonads of Lytechnicus variegatus (Echinodermata: echinoidea). Comp Biochem Physiol C 126:153–165

    CAS  Google Scholar 

  • Wasson KM, Gower BA, Watts SA (2000b) Responses of the ovaries and testes of Lytechinus variegatus (Echinodermata: Echinoidea) to dietary administration of progesterone, testosterone, and estradiol. Mar Biol 137:245–255

    Article  CAS  Google Scholar 

  • Watanabe M, Houten SM, Mataki C, Christoffolete MA, Kim BW, Sato H, Messaddeq N, Harney JW, Ezaki O, Kodama T, Schoonjans K, Bianco AC, Auwerx J (2006) Bile acids induce energy expenditure by promoting intracellular thyroid hormone activation. Nature 439:484–489

    Article  CAS  Google Scholar 

  • Watts SA, Lawrence JM (1987) The effects of 17β-estradiol and estrone on intermediary metabolism of the pyloric caeca of the asteroid Luidia clathrata (Say) maintained under different nutritional regimes. Dev Growth Differ 29:153–160

    Article  CAS  Google Scholar 

  • Welter V, Charlet M, Reuland M, Sauber F, Hoffmann JA (1986) Recherches sur les ecdystéroïdes présents dans les cocons de la sangsue Hirudo medicinalis au cours de l’embryogenèse. Int J Invertebr Reprod Dev 9:321–331

    CAS  Google Scholar 

  • Whitehead DL (1977) Steroids enhance shell regeneration in an aquatic gastropod (Biomphalaria glabrata). Comp Biochem Physiol C 58:137–141

    Article  CAS  Google Scholar 

  • Wright AD, Goclik E, König GM (2003) Oxygenated analogues of gorgosterol and ergosterol from the soft coral Capnella lacertiliensis. J Nat Prod 66:157–160

    Article  CAS  Google Scholar 

  • Xu RA (1991) Annual changes in the steroid levels in the testis and the pyloric caeca of Scleractias mollis (Hutton) (Echinodermata, Asteroidea) during the reproductive cycle. Invertebr Reprod Dev 20:147–152

    CAS  Google Scholar 

  • Xu RA, Barker MF (1990) Annual changes in the steroid levels in the ovaries and the pyloric caeca of Scleractinias mollis (Hutton 1872) (Echinodermata: Asteroidea) during the reproductive cycle. Comp Biochem Physiol A 95:127–133

    Article  Google Scholar 

  • Yano I (1985) Induced ovarian maturation and spawning in greasyback shrimp Metapenaeus ensis, by progesterone. Aquaculture 47:223–229

    Article  Google Scholar 

  • Yano I (1987) Effect of 17-α-OH-progesterone on vitellogenin secretion in kuruma prawn, Penaeus japonicus. Aquaculture 61:46–57

    Article  Google Scholar 

  • Yoshida M, Murata M, Inaba K, Morisawa M (2002) A chemoattractant for ascidian spermatozoa is a sulfated steroid. Proc Natl Acad Sci USA 99:14831–14836

    Article  CAS  Google Scholar 

  • Yoshikawa K, Kanekuni S, Hanahusa M, Arihara S, Ohta T (2000) Polyhydroxylated sterols from the octocoral Dendronephthya gigantea. J Nat Prod 63:670–672

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Zhu W, Mantione K, Jones D, Salamon E, Cho JJ, Cadet P, Stefano B (2003) The presence of 17-β estradiol in Mytilus edulis gonadal tissue—evidence for estradiol isoforms. Neuroendocrinol Lett 24:137–140

    CAS  Google Scholar 

  • Zhu Y, Rice CD, Pang Y, Pace M, Thomas P (2003) Cloning, expression and characterization of a membrane progestin receptor and evidence for its intermediary in meiotic maturation of fish oocytes. Proc Natl Acad Sci USA 100:2231–2236

    Article  CAS  Google Scholar 

  • 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 C 120:269–282

    Article  CAS  Google Scholar 

  • Zou E, Fingerman M (1997) Synthetic estrogenic agents do not interfere with sex differentiation but do inhibit molting of the cladoceran Daphnia magna. Bull Environ Contam Toxicol 58:596–602

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biochimie Structurale et Fonctionnelle des Protéines, CNRS FRE 2852, Université Pierre et Marie Curie, Case Courrier no. 29, 75252, Paris Cedex 05, France

    René Lafont

  2. Biologie et Biotechnologie Marines, UMR Ifremer Physiologie et Ecophysiologie des Mollusques Marins, IBFA, Université de Caen Basse-Normandie, F-14032, Caen Cedex, France

    Michel Mathieu

Authors
  1. René Lafont
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michel Mathieu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to René Lafont.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lafont, R., Mathieu, M. Steroids in aquatic invertebrates. Ecotoxicology 16, 109–130 (2007). https://doi.org/10.1007/s10646-006-0113-1

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10646-006-0113-1

Keywords

Search

Navigation