Kulolide: A cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa

Michael T. Reese, Nanda K. Gulavita, Youichi Nakao, Mark T. Hamann, Wesley Y. Yoshida, Stephen J. Coval, Paul J. Scheuer

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Kulolide, a cyclic depsipeptide, was isolated from a cephalaspidean mollusk, Philinopsis speciosa Pease, 1860. Kulolide is made up of five amino acid residues, one each of L-Ala, L-Pro, and N-Me-D-Val and two of L-Val, and two carboxylic acids, L-3-phenyllactic acid and the unprecedented (R)-3-hydroxy-2,2-dimethyl-7-octynoic acid. The kulolide structure was elucidated by spectral techniques and hydrolytic reactions. Kulolide is active against L-1210 leukemia cells and P388 murine leukemia cells at IC50 values of 0.7 and 2.l μg/mL, respectively. Kulolide caused morphological change against rat 3Y1 fibroblast cells at the concentration of 50 μM.

Original languageEnglish
Pages (from-to)11081-11084
Number of pages4
JournalJournal of the American Chemical Society
Volume118
Issue number45
DOIs
Publication statusPublished - 1996 Nov 13
Externally publishedYes

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Depsipeptides
Mollusca
Fibroblasts
Carboxylic Acids
Rats
Cells
Amino Acids
Acids
Carboxylic acids
Leukemia P388
Amino acids
Inhibitory Concentration 50
Leukemia
3-phenyllactic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Reese, M. T., Gulavita, N. K., Nakao, Y., Hamann, M. T., Yoshida, W. Y., Coval, S. J., & Scheuer, P. J. (1996). Kulolide: A cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa. Journal of the American Chemical Society, 118(45), 11081-11084. https://doi.org/10.1021/ja9620301

Kulolide : A cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa. / Reese, Michael T.; Gulavita, Nanda K.; Nakao, Youichi; Hamann, Mark T.; Yoshida, Wesley Y.; Coval, Stephen J.; Scheuer, Paul J.

In: Journal of the American Chemical Society, Vol. 118, No. 45, 13.11.1996, p. 11081-11084.

Research output: Contribution to journalArticle

Reese, MT, Gulavita, NK, Nakao, Y, Hamann, MT, Yoshida, WY, Coval, SJ & Scheuer, PJ 1996, 'Kulolide: A cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa', Journal of the American Chemical Society, vol. 118, no. 45, pp. 11081-11084. https://doi.org/10.1021/ja9620301
Reese, Michael T. ; Gulavita, Nanda K. ; Nakao, Youichi ; Hamann, Mark T. ; Yoshida, Wesley Y. ; Coval, Stephen J. ; Scheuer, Paul J. / Kulolide : A cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa. In: Journal of the American Chemical Society. 1996 ; Vol. 118, No. 45. pp. 11081-11084.
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