Skip to main content
SpringerLink
Log in

Callyspongynes A and B: New polyacetylenic lipids from a southern australian marine sponge, Callyspongia sp

  • Communication
  • Published:
Lipids

Abstract

A Callyspongia sp. collected by SCUBA off Barwon Heads, Australia, has afforded two new polyacetylenic lipids, callyspongynes A and B, the structures of which were assigned by spectroscopic analysis and chemical derivatization.

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

Similar content being viewed by others

Abbreviations

EI:

electron impact ionization

EIMS:

electron impact mass spectrometry

ESI:

electrospray ionization

HPLC:

high-performance liquid chromatography

IR:

infrared

MS:

mass spectrometry

MTPA:

α-methoxy-α-(trifluoromethyl)phenylacetic acid

NMR:

nuclear magnetic resonance

References

  1. Cimino, G., De Giulio, A., De Rosa, S., and Di Marzo, V. (1989) High Molecular Weight Polyacetylenes from the Petrosia ficiformis: Further Structural Analysis and Biological Activity, Tetrahedron 30, 3563–3566.

    Article  CAS  Google Scholar 

  2. Masamitsu, O., Saori, A., Tatssukawa, A., Hiyoshizo, K., Fukuyama, Y., and Shibata, K. (1994) Bioactive Polyacetylenes from the Marine Sponge Petrosia sp., Chem. Lett., 89–92.

  3. Cimino, G., De Giulio, A., De Rosa, S., and Di Mario, V. (1990) Minor Bio-Active Polyacetylenes from Petrosia ficiformis J. Nat. Prod. 53, 345–353.

    Article  CAS  Google Scholar 

  4. Guo, Y., Gavanin, M., Trivellone, E., and Cimino, G. (1994) Absolute Stereochemistry of Petroformynes, High Molecular Weight Polyacetylenes from the Marine Sponge Petrosia ficiformis, Tetrahedron 50, 13261–13268.

    Article  CAS  Google Scholar 

  5. Guo, Y., Gavanin, M., Trivellone, E., and Cimino, G. (1994) Further Structural Studies on the Petroformynes, J. Nat. Prod. 58, 712–722.

    Article  Google Scholar 

  6. Fusetani, N., Shiragaki, T., Matsunaga, S., and Hashimoto, K. (1987) Bioactive Marine Metabolites XX1. Petrosynol and Petrosynone, Antimicrobial C30 Polyacetylenes from the Marine Sponge Petrosia sp. Determination of the Absolute Configuration, Tetrahedron Lett. 28, 4313–4314.

    Article  CAS  Google Scholar 

  7. Li, H.Y., Matsunaga, S., and Fusetani, N. (1994) Corticatic Acids A-C, Antifungal Acetylenic Acids from the Marine Sponge, Petrosia corticata, J. Nat. Prod. 54, 1464–1467.

    Article  Google Scholar 

  8. Castiello, D., Cimmino, G., De Rosa, S., Stefano, S., and Sodano, G. (1980) High Molecular Weight Polyacetylenes from the Nudibrach Peltodoris atromaculata and the Sponge Petrosia ficiformis, Tetrahedron Lett. 21, 5047–5050.

    Article  CAS  Google Scholar 

  9. Aeillo, A., Fattorusso, E., Menna, M. (1992) Further Bioactive Acetylenic Compounds from the Caribbean Sponge Criblochalina vasculum, J. Nat. Prod. 9, 1275–1280.

    Article  Google Scholar 

  10. Wright, A.E., McConnell, O.J., Kohmoto, S., Lui, M.S., Thompson, W., and Snader, K.M. (1987) Duryne, A New Cytotoxic Agent from the Marine Sponge Cribrochalina dura, Tetrahedron Lett. 28, 1377–1380.

    Article  CAS  Google Scholar 

  11. Hallock, Y.F., Cardellina, II, J.H., Balaschak, M.S., Alexander, M.R., Prather, T.R., Shoemaker, R.H., and Boyd, M.R. (1995) Antitumour Activity and Stereochemistry of Acetylenic Alcohols from the Sponge Cribrochalina vasc dum, J. Nat. Prod. 58, 1801–1807.

    Article  PubMed  CAS  Google Scholar 

  12. Gunasekera, S.P., and Faircloth, G.T. (1990) New Acetylenic Alcohols from the Sponge Cribrochalina vasculum, J. Org. Chem. 55, 6223–6225.

    Article  CAS  Google Scholar 

  13. Kato, Y., Matsunaga, S., Hashimoto, K., and Fusetani, N. (1983) Bioactive Marine Metabolites III. A Novel Polyacetylene Alcohol, Inhibitor of Cell Division in Feritilized Sea Urchin Eggs, from the Marine Sponge Tetrosia sp., Tetrahedron Lett. 24, 2271–2274.

    Article  Google Scholar 

  14. Li, Y., Ishibashi, M., Sasaki, T., and Kobayashi, J. (1995) New Bromine-Containing Unsaturated Fatty Acid Derivatives from the Okinawan Marine Sponge Xestospongia sp., J. Chem. Res. 4, 901–923.

    Google Scholar 

  15. Brantley, S.E., Molinski, T.F., Preston, C.M., and DeLong, E.F. (1995) Brominated Acetylenic Fatty Acids from Xestospongia sp. A marine Sponge-Bacteria Association, Tetrahedron 51, 7667–7672.

    Article  CAS  Google Scholar 

  16. Haruhiko, T., and Fumio, Y. (1984) Siphonodiol. A New Polyacetylenic Metabolite from the Sponge Siphonochalina truncate, Chem. Lett. 779–780.

  17. Ortega, M.J., Zubia, E., Carballo, J.L., and Salva, J. (1986) Fulvinol, a Long-Chain Diacetylenic Metabolite from the Marine Sponge Reniera fulva, J. Nat. Prod. 59, 1069–1071.

    Article  Google Scholar 

  18. Williams, D.H., and Faulkner, D.J. (1996) Three New Acetylenes from the Palauan Sponge Haliconia sp., J. Nat. Prod. 59, 1099–1101.

    Article  CAS  Google Scholar 

  19. Miao, S., and Andersen, R.J. (1996) A New Diacetylenic Hydrocarbon from the Sponge Callyspongia flammea, Callyiyne, J. Nat. Prod. 54, 1433–1434.

    Article  Google Scholar 

  20. Urban, S., and Capon, R.J. (1997) A New Lipid from an Australian Marine Sponge, Callyspongia sp., Lipids 32, 675–677.

    PubMed  CAS  Google Scholar 

  21. Dale, J., and Mosher, S. (1973) Nuclear Magnetic Resonance Enantiomer Reagents, Configurational Correlations via Nuclear Magnetic Chemical Shifts of Diastereometric Mandelate, O-Methylmandelate, and α-Methoxy-α-trifluoromethylphenylacetate (MTPA) Esters, J. Am. Chem. Soc. 95, 512–516.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, The University of Melbourne, 3052, Parkville, Victoria, Australia

    Francis Rooney & Robert J. Capon

Authors
  1. Francis Rooney
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Robert J. Capon
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Robert J. Capon.

About this article

Cite this article

Rooney, F., Capon, R.J. Callyspongynes A and B: New polyacetylenic lipids from a southern australian marine sponge, Callyspongia sp. Lipids 33, 639–642 (1998). https://doi.org/10.1007/s11745-998-0251-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-998-0251-5

Keywords

Search

Navigation