Skip to main content
SpringerLink
Log in

Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica

  • Short Communication
  • Published:
Naturwissenschaften Aims and scope Submit manuscript

Abstract

Chemical investigation of the deepwater sponge Macandrewia azorica, collected from the flanks of the Gettysburg and Ormonde Sea Mount, North Atlantic, from a depth of 600 m, has led to the isolation of a new sterol with an unusual side chain (1), along with S-methylergothioneine (2). The structures of compounds 1 and 2 were established by employing spectroscopic techniques (NMR, MS, UV, IR and polarimetry). This is the first report of metabolites of a sponge belonging to the genus Macandrewia.

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 a
Fig. 2

References

  • Aiello A, Fattorusso E, Menna M, Carniccio R, Iuvone T (1995) New cytotoxic steroids from the marine sponge Dysidea fragilis coming from the lagoon of Venice. Steroids 60:666–673

    CAS  PubMed  Google Scholar 

  • Almeida Leone P de, Redburn J, Hooper JNA, Quinn RJ (2000) Polyoxygenated Dysidea sterols that inhibit the binding of [I125] IL-8 to the human recombinant IL-8 receptor type A. J Nat Prod 63:694–697

    PubMed  Google Scholar 

  • Aruoma OI, Spencer JPE, Mahmood N (1999) Protection against oxidative damage and cell death by the natural antioxidant ergothioneine. Food Chem Toxicol 37:1043–1053

    CAS  PubMed  Google Scholar 

  • Asmus KD, Bensasson RV, Bernier JL, Houssin R, Land EJ (1996) One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C. Biochem J 315:625–629

    CAS  PubMed  Google Scholar 

  • Blunt JW, Stothers JB (1977) 13C N.M.R. spectra of steroids: a survey and commentary. Org Magn Reson 9:439–464

    CAS  Google Scholar 

  • Creasey SS, Rogers AD (1999) Population genetics of bathyal and abyssal organisms. In: Southward AJ, Tyler PA, Young CM (eds) Advances in marine biology. Academic Press, San Diego, pp 1–151

  • De Luca P, De Rosa M, Minale L, Sodano G (1972) Marine sterols with a new pattern of side-chain alkylation from the sponge Aplysina (= Verongia) aerophoba. J Chem Soc Perkin 1:2132–2135

    Google Scholar 

  • Djerassi C (1981) Recent studies in the marine sterol field. Pure Appl Chem 53:873–890

    CAS  Google Scholar 

  • Funel C, Berrué F, Roussakis C, Rodriguez RF, Amade P (2004) New cytotoxic steroids from the Indian Ocean sponge Axinella cf. bidderi. J Nat Prod 67:491–494

    Article  CAS  PubMed  Google Scholar 

  • Hoffmann F, Janussen D, Dröse W, Arp G, Reitner J (2003) Histological investigation of organisms with hard skeletons: a case study of siliceous sponges. Biotech Histochem 78:191–199

    CAS  PubMed  Google Scholar 

  • Ikekawa N (1985) Structures, biosynthesis and function of sterols in invertebrates. In: Danielsson H, Sjövall J (eds) Sterols and bile acids. Elsevier, Amsterdam, pp 199–230

  • Ishikawa Y, Israel SE, Melville DB (1974) Participation of an intermediate sulfoxide in the enzymatic thiolation of the imidazole ring of hercynine to form ergothioneine. J Biol Chem 249:4420–4427

    CAS  PubMed  Google Scholar 

  • Kerr RG, Kerr SL, Pettit GR, Herald DL, Groy TL, Djerassi C (1991) Sterols of marine invertebrates. 63. Isolation and structure elucidation of sutinasterol, the major sterol of the marine sponge Xestospongia sp. J Org Chem 56:58–62

    CAS  Google Scholar 

  • Keyzers RA, Northcote PT, Webb V (2002) Clathriol, a novel polyoxygenated 14β steroid isolated from the New Zealand marine sponge Clathria lissosclera. J Nat Prod 65:598–600

    CAS  PubMed  Google Scholar 

  • Konno K, Shirahama H, Matsumoto T (1984) Clithioneine, an amino acid betaine from Clitocybe acromelalga. Phytochemistry 23:1003–1006

    Article  CAS  Google Scholar 

  • Matsuo M, Sato K, Kitani S, Satomura Y (1967) Isolation and structure of sclerothionine, a metabolite of Sclerotinia fungus. Agric Biol Chem 31:353–356

    CAS  Google Scholar 

  • Melville DB (1959) Ergothioneine. In: Harris RS, Marrian GF, Thimann KV (eds) Vitamins and hormones: advances in research and applications, vol XVII. Academic Press, New York, pp 155–204

  • Motohashi N, Mori I, Sugiura Y (1976) 13C-nuclear magnetic resonance and Raman spectroscopic studies on ionization and mercury complex of ergothioneine. Chem Pharm Bull 24:1737–1741

    CAS  Google Scholar 

  • Nes WR, McKean ML (1977) Biochemistry of steroids and other isoterpenoids. University Park Press, Baltimore, Md., pp 325–410

  • Pisera A, Lévi C (2002) “Lithistid” Demospongiae. In: Hooper JNA, van Soest RWM (eds) Systema Porifera: a guide to the classification of sponges. Kluwer, New York, pp 299–387

  • Pretsch E, Bühlmann P, Affolter C, Badertscher M (2001) Spektroskopische Daten zur Strukturaufklärung organischer Verbindungen. Springer, Berlin Heidelberg New York, p 156

  • Qureshi A, Faulkner JD (2000) 7α-Hyxdroxytheonellasterol, a cytotoxic 4-methylene sterol from the Philippines sponge Theonella swinhoei. J Nat Prod 63:841–841

    Article  CAS  PubMed  Google Scholar 

  • Reitner J (1993) Modern cryptic microbialite/metazoan facies from Lizard Island (Great Barrier Reef, Australia): formation and concepts. Facies 29:3-40

    Google Scholar 

  • Richer de Forges B, Koslow JA, Poore GCB (2000) Diversity and endemism of the benthic seamount fauna in the southwest Pacific. Nature 405:944–947

    Article  PubMed  Google Scholar 

  • Rudi A, Yosief T, Loya S, Hizi A, Schleyer M, Kashman Y (2001) Clathsterol, a novel anti-HIV-1 RT sulfated sterol from the sponge Clathria species. J Nat Prod 64:1451–1453

    Article  CAS  PubMed  Google Scholar 

  • Santafé G, Paz V, Rodriguez J, Jiménez C (2002) Novel cytotoxic oxygenated C29 sterols from the Colombian marine sponge Polymastia tenax. J Nat Prod 65:1161–1164

    Article  PubMed  Google Scholar 

  • Shen Y, Burgoyne DL (2002) Efficient synthesis of IPL576,092: a novel anti-asthma agent. J Org Chem 67:3908–3910

    Article  CAS  PubMed  Google Scholar 

  • Shoji N, Umeyama A, Shin K, Takeda K, Arihara S, Kobayashi J, Takei M (1992) Two unique pentacyclic steroids with cis C/D junction from Xestospongia bergquistia Fromont, powerful inhibitors of histamine release. J Org Chem 57:2996–2997

    CAS  Google Scholar 

  • Shubina LK, Makar’eva TN, Kalinovskii AI, Stonik VA (1985) Steroid compounds of marine sponges. IV. New sterols with unusual side chains from the fungus Halichondria sp. Chem Nat Compd (English translation) 21:217–223 / Khim Prir Soedin 2:232–239

    Google Scholar 

  • Su J, Yu X, Zeng L, Mak TCW (1989) Novel polyhydroxylated sterols from the soft coral Sinularia numerosa. J Nat Prod 52:934–940

    CAS  Google Scholar 

  • Xu J, Yadan JC (1995) Synthesis of L(+)-ergothioneine. J Org Chem 60:6296–6301

    CAS  Google Scholar 

Download references

Acknowledgement

We are grateful to G. Eckhardt, Institute for Chemistry, University of Bonn, and P. Janning, Max Planck Institute for Molecular Physiology, Dortmund, for EIMS and HRFABMS measurements. This paper respresents publication no. 48 of the research program BOSMAN 03FO358D. Financial support was provided by the Bundesministerium für Bildung und Forschung (BMBF).

Author information

Authors and Affiliations

  1. Pharmazeutische Biologie, Universität Bonn, Nussallee 6, 53115, Bonn, Germany

    Harald Gross & Gabriele M. König

  2. Göttinger Zentrum Geowissenschaften GZG, Abteilung Geobiologie, Universität Göttingen, Goldschmidtstrasse 3, 37077, Göttingen, Germany

    Joachim Reitner

Authors
  1. Harald Gross
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joachim Reitner
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gabriele M. König
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gabriele M. König.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gross, H., Reitner, J. & König, G.M. Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica. Naturwissenschaften 91, 441–446 (2004). https://doi.org/10.1007/s00114-004-0552-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00114-004-0552-6

Keywords

Search

Navigation