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, Youichi Nakao, Wesley Y. Yoshida, Paul J. Scheuer

Research output: Contribution to journalArticle

30 Citations (Scopus)

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 IC 50 = 7.5 μg/mL.

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

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Homoarginine
Stereochemistry
Hydroxyproline
Nuclear magnetic resonance
Amino Acids
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bonnington, L. S., Tanaka, J., Higa, T., Kimura, J., Yoshimura, Y., Nakao, 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.

Cupolamide A : A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola. / Bonnington, Lea S.; Tanaka, Junichi; Higa, Tatsuo; Kimura, Junji; Yoshimura, Yuki; Nakao, Youichi; Yoshida, Wesley Y.; Scheuer, Paul J.

In: Journal of Organic Chemistry, Vol. 62, No. 22, 1997, p. 7765-7767.

Research output: Contribution to journalArticle

Bonnington, LS, Tanaka, J, Higa, T, Kimura, J, Yoshimura, Y, Nakao, Y, Yoshida, WY & Scheuer, PJ 1997, 'Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola', Journal of Organic Chemistry, vol. 62, no. 22, pp. 7765-7767.
Bonnington LS, Tanaka J, Higa T, Kimura J, Yoshimura Y, Nakao Y et al. Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola. Journal of Organic Chemistry. 1997;62(22):7765-7767.
Bonnington, Lea S. ; Tanaka, Junichi ; Higa, Tatsuo ; Kimura, Junji ; Yoshimura, Yuki ; Nakao, Youichi ; Yoshida, Wesley Y. ; Scheuer, Paul J. / Cupolamide A : A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 22. pp. 7765-7767.
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