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Isolation and identification of major ecdysteroids from the pycnogonidPycnogonum litorale (Ström) (Arthropoda, Pantopoda)

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Summary

From adults ofPycnogonum litorale (Ström) eight ecdysteroids were isolated by HPLC and identified by mass spectrometry and NMR. One of the compounds is 20-hydroxyecdysone, two further ecdysteroids show no OH-group at C-22 (22-deoxy-20,26-dihydroxyecdysone, 22-deoxy-20-hydroxyecdysone=taxisterone). The five other compounds are esters of ecdysteroids with acetic acid (25R and 25S isomers of 20,26-dihydroxyecdysone 22-acetate, 20-hydroxyecdysone 22-acetate) or with glycolic acid (20-hydroxyecdysone 22-glycolate, ecydsone 22-glycolate). The latter are new among zoo- and phytoecdysteroids. No significant amounts of ecdysone could be detected. The origin of the ecdysteroids inPycnogonum litorale and their biological activity are discussed.

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Abbreviations

RP-HPLC :

Reversed-phase high performance liquid chromatography

NP :

normal phase

RIA :

radioimmunoassay

NMR :

nuclear magnetic resonance

FT :

Fourier transform

CI/D :

chemical ionization/desorption

TFA :

trifluoroacetic acid

E :

ecdysone

20E :

20-hydroxyecdysone

2026E 20 :

26-dihydroxyecdysone

References

  • Bax A, Freeman R (1981) Investigation of complex networks of spin-spin coupling by two-dimensional NMR. J Magn Res 44:542–561

    Google Scholar 

  • Behrens W (1981) Morphologische und hormonphysiologische Untersuchungen an einem Pantopoden,Pycnogonum litorale STRÖM. Dissertation, Universität Ulm

  • Behrens W, Bückmann D (1983) Ecdysteroids in the pycnogonidPyncogonum litorale (STRÖM) (Arthropoda, Pantopoda). Gen Comp Endocrinol 51:8–14

    Google Scholar 

  • Bergamasco R, Horn DHS (1980) The biological activities of ecdysteroids and ecdysteroid analogues. In: Hoffmann JA (ed) Progress in ecdysone research. Elsevier/North-Holland, Amsterdam, pp 299–324

    Google Scholar 

  • Bergström J, Stürmer W, Winter G (1980)Palaeoisopus, Palaeopantopus andPalaeothea, pycnogonid arthropods from the Lower Devonian Hunsrück Slate, West Germany. Paläontol Z 54:7–54

    Google Scholar 

  • Dennis RDW (1977) On ecdysone-binding proteins and ecdysone-like material in nematodes. J Parasitol 7:181–188

    Google Scholar 

  • Diehl PA, Connat JL, Girault JP, Lafont R (1985) A new class of apolar ecdysteroid conjugates: esters of 20-hydroxy-ecdysone with long-chain fatty acids in ticks. Int J Invert Repord Dev 8:1–13

    Google Scholar 

  • Feldlaufer MF, Svoboda JA (1986) Makisterone A, a 28-carbon insect ecdysteroid. Insect Biochem 16:45–48

    Google Scholar 

  • Galbraith MN, Horn DHS, Middleton EJ, Hackney RJ (1969) Moulting hormones in insects and crustanceans: the synthesis of 22-deoxycrustecdysone. Aust J Chem 22:1517–1524

    Google Scholar 

  • Garcia M, Girault JP, Lafont R (1986) Ecdysteroid metabolism in the terrestrial snailCepaea nemoralis (L.). Int J Invert Reprod Dev 9:43–58

    Google Scholar 

  • Gilbert LI, King DS (1973) Physiology of growth and development: Endocrine aspects. In: Rockstein M (ed) The physiology of Insecta, vol 1, 2nd edn. Academic Press, New York, pp 249–370

    Google Scholar 

  • Gilgan MW, Burns BG (1977) Molt induction in lobsters (Homarus americanus) by intramuscular injection of ecdysone triacetate. Experientia 33:1114–1115

    Google Scholar 

  • Guerriero A, Pietra F (1985) Isolation, in large amounts, of the rare plant ecdysteroid ajugasterone-C from the mediterranean zoanthidGerardia savaglia. Comp Biochem Physiol 80B:277–278

    Google Scholar 

  • Habermehl G, Christ B, Krebs HC (1976) Die freien Steroide inMetridium senile. Naturwissenschaften 63:42

    Google Scholar 

  • Hoffmann JA (ed) (1980) Progress in ecdysone research. Elsevier/North Holland, Amsterdam

    Google Scholar 

  • Horn DHS (1971) The ecdysones. In: Jacbsen M, Crosby DG (eds) Naturally occurring insecticides. Marcel Dekker. New York, pp 333–459

    Google Scholar 

  • Horn DHS, Wilkie JS, Thomson JA (1974) Isolation of β-ecdysone (20-hydroxyecdysone) from the parasitic nematodeAscaris lumbricoides. Experientia 30:1109–1110

    Google Scholar 

  • Horn DHS, Bergamasco R (1985) Chemistry of ecdysteroids. In: Kerkut GA, Gilbert LI (eds) Comprehensive insect physiology biochemistry and pharmacology, vol 7. Pergamon Press, Oxford pp 185–248

    Google Scholar 

  • Isaac RE, Rees HH, Goodwin TW (1981) Isolation of ecdysone-3-acetate as a major ecdysteroid from developing eggs of desert locust,Schistocerca gregaria. J Chem Soc, Chem Commun 594–595

  • Isaac RE, Rose ME, Rees HH, Goodwin TW (1982) Identification of ecdysone-22-phosphate and 2-deoxyecdysone-22-phosphate in eggs of the desert locust,Schistocerca gregaria, by fast atom bombardment mass spectrometry and N.M.R. spectroscopy. J Chem Soc, Chem Commun 249–251

  • Lachaise F, Goudeau M, Hetru C, Kappler C, Hoffmann JA (1981) Ecdysteroids and ovarian development in the shore crab,Carcinus maenas. Hoppe-Seyler's Z Physiol Chem 362:521–529

    Google Scholar 

  • Lachaise F, Meister M, Hetru C, Lafont R (1986) Studies on the biosynthesis of ecdysome by the Y-organs ofCarcinus maenas. Mol Cell Endocrinol 45:253–261

    Google Scholar 

  • Lafont R, Martin-Somme G, Chambet JC (1979) Separation of ecdysteroids by using high-pressure liquid chromatography on microparticulate supports. J Chromatogr 170:185–194

    Google Scholar 

  • Lafont R, Beydon P, Mauchamp B, Somme-Martin G, Andrianjafintrimo M, Krien P (1981) Recent progress in ecdysteroids analytical methods. In: Sehnal F, Zabza A, Cymborowski B (eds) Regulation of insect development and behaviour, vol 1. Technical University of Wroclaw Press, Poland, pp 125–144

    Google Scholar 

  • Lafont R, Pennetier JL, Andrianjafintrimo M, Claret J, Modde JF, Blais C (1982) Sample processing for high-performance liquid chromatography of ecdysteroids. J Chromatogr 236:137–149

    Google Scholar 

  • Lafont R, Blais C, Beydon P, Modde JF, Enderle U, Koolman J (1983) Conversion of ecdysone and 20-hydroxyecdysone into 26-oic derivatives is a major pathway in larvae and pupae of species from three insect orders. Arch Insect Biochem Physiol 1:41–58

    Google Scholar 

  • McCarthy JF (1979) Ponasterone A: A new ecdysteroid from the embryos and serum of brachyuran crustaceans. Steroids 34:799–806

    Google Scholar 

  • Mendis AWH, Rose ME, Rees HH, Goodwin TW (1983) Ecdysteroids in adults of the nematode,Dirofilaria immitis. Mol Biochem Parasitol 9:209–226

    Google Scholar 

  • Mendis AHW, Rees HH, Goodwin TW (1984) The occurrence of ecdysteroids in the cestode,Moniezia expansa. Mol Biochem Parasitol 10:123–138

    Google Scholar 

  • Modde JF, Lafont R, Hoffmann JA (1984) Ecdysone metabolism inLocusta migratoria larvae and adults. Int J Invert Reprod Dev 7:161–183

    Google Scholar 

  • Nakanishi K (1971) The ecdysones. Pure Appl Chem 25:167–195

    Google Scholar 

  • Nakano K, Nohara T, Tomimatsu T, Nishikawa M (1982) A phytoecdysteroid, taxisterone, fromTaxus cuspidata. Phytochemistry 21:2749–2751

    Google Scholar 

  • Nirde P, Torpier G, De Reggi ML, Capron A (1983) Ecdysone and 20-hydroxyecdysone: new hormones for the human parasiteSchistosoma mansoni. FEBS Lett 151:223–227

    Google Scholar 

  • Redfern CPF (1984) Evidence for the presence of makisterone A inDrosphila larvae and the secretion of 20-deoxymakisterone A by the ring gland. Proc Natl Acad Sci USA 81:5643–5647

    Google Scholar 

  • Romer F (1979) Ecdysteroids in snails. Naturwissenschaften 66:471–472

    Google Scholar 

  • Russell GB, Price GM (1977) Metabolism of β-ecdysone during the larval and white puparial stage of the blowfly,Calliphora erythrocephala. Insect Biochem 7:197–202

    Google Scholar 

  • Sall C, Tsoupras G, Kappler C, Lagueux M, Zachary D, Luu B, Hoffmann JA (1983) Fate of maternal conjugated ecdysteroids during embryonic development inLocusta migratoria. J Insect Physiol 29:491–507

    Google Scholar 

  • Sauber F, Reuland M, Berchtold JP, Hetru C, Tsoupras G, Luu B, Moritz ME, Hoffmann JA (1983) Cycle de mue et ecdystéroïdes chez une sangsue,Hirudo medicinalis. CR Acad Sci Paris, Sér D 296:413–418

    Google Scholar 

  • Schmidt HW, Bückmann D (1971) Beobachtungen zur Lebensweise vonPycnogonum litorale (STRÖM) (Pantopoda). Oecologia 7:242–248

    Google Scholar 

  • Spindler KD, Beckers C, Gröschel-Steward U, Emmerich H (1978) A radioimmunoassay for arthropod moulting hormones introducing a novel method of immunogen coupling. Hoppe-Seyler's Z Physiol Chem 359:1269–1275

    Google Scholar 

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

    Google Scholar 

  • Takemoto T, Ogawa S, Nishimoto N, Hoffmeister H (1967) Steroide mit Häutungshormon-Aktivität aus Tieren und Pflanzen. Z Naturforsch 22b:681–682

    Google Scholar 

  • Tsoupras G, Hetru C, Luu B, Constantin E (1983a) Identification and metabolic fate of ovarian 22-adenosine monophosphoric ester of 2-deoxyecdysone in ovaries and eggs of an insect,Locusta migratoria. Tetrahedron 39:1789–1796

    Google Scholar 

  • Tsoupras G, Luu B, Hetru C, Muller JF, Hoffmann JA (1983b) Conversion in vitro de 20-hydroxyecdysone en métabolites phosphorylés et acétylés par des complexes tubes digestiftubes de Malpighi de larves deLocusta migratoria. CR Acad Sci, Sér III 296:77–80

    Google Scholar 

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

    Google Scholar 

  • Whitehead DL, Sellheyer K (1982) The identification of ecdysterone (20-hydroxyecdysone) in 3 species of molluscs (Gastropoda: Pulmonata). Experientia 38:1249–1251

    Google Scholar 

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Authors and Affiliations

  1. Abteilung Allgemeine Zoologie, Universität Ulm, D-7900, Ulm, Federal Republic of Germany

    D. Bückmann, G. Starnecker, K. -H. Tomaschko & E. Wilhelm

  2. CNRS UA 686, E.N.S. Laboratoire de Zoologie, 46 rue d'Ulm, F-75230, Paris Cedex 05, France

    R. Lafont

  3. Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, CNRS UA 400, Université René Descartes, F-75270, Paris Cedex 06, France

    J. -P. Girault

Authors
  1. D. Bückmann
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  2. G. Starnecker
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  3. K. -H. Tomaschko
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  4. E. Wilhelm
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  5. R. Lafont
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  6. J. -P. Girault
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Bückmann, D., Starnecker, G., Tomaschko, K.H. et al. Isolation and identification of major ecdysteroids from the pycnogonidPycnogonum litorale (Ström) (Arthropoda, Pantopoda). J Comp Physiol B 156, 759–765 (1986). https://doi.org/10.1007/BF00694248

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