Skip to main content
Log in

Prepatellamide A, a new cyclic peptide from the ascidianLissoclinum patella

  • Published:
Science in China Series B: Chemistry Aims and scope Submit manuscript

Abstract

A new cyclic peptide, prepatellamide A (1), along with three known cyclic peptides (2)— (4), was isolated from the ascidianLissoclinum patella. The structure of prepatellamide A was determined from one- and two-dimensional1H and13C NMR spectra. The known cyclic peptides were identified as patellamides A (2), B (3) and C (4).

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Davidson, B. S., Ascidians producter of amino acid derived metabolites, Chem. Rev., 1993, 93: 1771.

    Article  CAS  Google Scholar 

  2. Fu, X., Do, T., Schmitz, F. J. et al., New cyclic peptides from the ascidianLissoclimim patella, J. Nat. Prod., 1998, 61: 1547.

    Article  CAS  Google Scholar 

  3. Wasylyk, J. M., Biskupiak, J. E., Costello, C. E. et al., Cyclic peptide structure from the tunicateLissoclinum patella by FAB mass spectrometry, J. Org. Chem., 1983, 48: 4445.

    Article  CAS  Google Scholar 

  4. Ireland, C., Scheuer, P. J., Ulcyclamide and ulthiacycliamide, two new small peptides from a marine tunicate, J. Am. Chem. Soc., 1980, 102: 5688.

    Article  CAS  Google Scholar 

  5. Williams, D. E., Moore, R. E., The structure of ulthiacycliamide B, antitumor evaluation of cyclic peptides and macrolides fromLissoclinum patella, J. Nat. Prod., 1989, 52: 732.

    Article  CAS  Google Scholar 

  6. Degnan, B. M., Hawkins, C. J., Lavin, M. F. et al., New cyclic peptides with cytotoxic activity from the ascidianLissoclinum patella, J. Med. Chem., 1989, 32: 1349.

    Article  CAS  Google Scholar 

  7. Hawkins, C. J., Lavin, M. F., Marshall, K. A. et al., Structure-activity relationship of the lissoclinamides cytotoxic cyclic peptides from the ascidianLissoclinum patella, J. Med. Chem., 1990, 33: 1634.

    Article  CAS  Google Scholar 

  8. McDonald, L. A., Foster, M. P., Phillips, D. R. et al., Tawicyclamides A and B, new cyclic peptides from the ascidianLissoclinum patella, studies on the solution and solid-state conformation, J. Org. Chem., 1992, 57: 4616.

    Article  CAS  Google Scholar 

  9. Zabriskie, T. M., Foster, M. P., Stout, T. J. et al., Studies on the solution and solid-state structure of patellin 2, J. Am. Chem. Soc., 1990, 112: 8080.

    Article  CAS  Google Scholar 

  10. In, Y., Doi, M., Inoue, M. et al., Molecular conformation of patellamide A, a cytotoxic cyclic peptide from the assidianLissoclinumpatellaby X-ray crystal analysis, Chem. Pharm. Bull., 1993, 41: 1686.

    CAS  Google Scholar 

  11. Ireland, C. M., Durso, A. R., Newman, R. A. et al., Antineoplastic cyclic peptides from the marine tunicateLissoclinum patella, J. Org. Chem., 1982, 47: 1807.

    Article  CAS  Google Scholar 

  12. Sesin, D. F., Gaskell, S. J., Ireland, CM., The chemistry ofLissoclinum patella, Bull. Soc. Chim. Belg., 1986, 95: 853.

    CAS  Google Scholar 

  13. McDonald, L. A., Ireland, C. M., Patellamide E, a new cyclic peptide from the ascidianLissoclimim patella, J. Nat. Prod., 1992, 55: 376.

    Article  CAS  Google Scholar 

  14. Rashid, M. A., Gustafson, K. R., John H. et al., Patellamide F, a new cytotoxic cyclic peptide from the clonial ascidianLissoclinum patella, J. Nat. Prod., 1995, 58: 594.

    Article  CAS  Google Scholar 

  15. Schmitz, F. J., Ksebati, M. B., Chang, J. S. et al., Cyclic peptides from the ascidianLissoclinum Patella: conformational analysis of the patellaide D by X-ray analysis and molecular modeling, J. Org. Chem., 1989, 54: 3463.

    Article  CAS  Google Scholar 

  16. Fu, X., Schmitz, F. J., Lee, R. H. et al., Inhibitors of protein tyrosine kinase pp60v-src sterol sulfates from the brittle starOphiarchina incrassata, J. Nat. Prod., 1994, 57: 1591.

    Article  CAS  Google Scholar 

  17. Hamada, Y., Shibata, M., Shioiri, T., New methods and reagents in organic synthesis 56, total synthesis of patellamides B and C, Tetrahedron Lett., 1985, 26: 5159.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zeng Longmei.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fu, X., Su, J. & Zeng, L. Prepatellamide A, a new cyclic peptide from the ascidianLissoclinum patella . Sc. China Ser. B-Chem. 43, 643–648 (2000). https://doi.org/10.1007/BF02969512

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02969512

Keywords

Navigation