Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

Lea S. Bonnington, Junichi Tanaka, Tatsuo Higa, Junji Kimura, Yuki Yoshimura, Yoichi Nakao, Wesley Y. Yoshida, Paul J. Scheuer

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Abstract

A new cyclic heptapeptide cupolamide A (1) was isolated from two samples of the sponge Theonella cupola collected in Indonesia and Okinawa. It contains two L-Val, one D-Leu, and one D-Ser, and three uncommon amino acid residues, D-homoarginine (Har), trans-4-hydroxy-L-proline (Hyp), and L-2,4-diaminobutanoic acid (Dba). The structure elucidation of 1 was performed by NMR spectroscopic techniques and the stereochemistry was determined by Marfey's method. Cupolamide A (1) was active against P388 murine leukemia cells with an IC50 = 7.5 μg/mL.

Original languageEnglish
Pages (from-to)7765-7767
Number of pages3
JournalJournal of Organic Chemistry
Volume62
Issue number22
DOIs
Publication statusPublished - 1997 Jan 1

ASJC Scopus subject areas

  • Organic Chemistry

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    Bonnington, L. S., Tanaka, J., Higa, T., Kimura, J., Yoshimura, Y., Nakao, Y., Yoshida, W. Y., & Scheuer, P. J. (1997). Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola. Journal of Organic Chemistry, 62(22), 7765-7767. https://doi.org/10.1021/jo9710285