Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa

Junji Kimura, Yuuki Takada, Tomoko Inayoshi, Youichi Nakao, Gilles Goetz, Wesley Y. Yoshida, Paul J. Scheuer

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 μg/mL.

Original languageEnglish
Pages (from-to)1760-1767
Number of pages8
JournalJournal of Organic Chemistry
Volume67
Issue number6
DOIs
Publication statusPublished - 2002 Mar 22
Externally publishedYes

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Depsipeptides
Amino Acids
Hydroxy Acids
Stereochemistry
Stereoisomerism
Spectroscopic analysis
Cytotoxicity
Degradation
kulokekahilide-1
3-amino-2-methylhexanoic acid
4-phenylvaline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kimura, J., Takada, Y., Inayoshi, T., Nakao, Y., Goetz, G., Yoshida, W. Y., & Scheuer, P. J. (2002). Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa. Journal of Organic Chemistry, 67(6), 1760-1767. https://doi.org/10.1021/jo010176z

Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa. / Kimura, Junji; Takada, Yuuki; Inayoshi, Tomoko; Nakao, Youichi; Goetz, Gilles; Yoshida, Wesley Y.; Scheuer, Paul J.

In: Journal of Organic Chemistry, Vol. 67, No. 6, 22.03.2002, p. 1760-1767.

Research output: Contribution to journalArticle

Kimura, J, Takada, Y, Inayoshi, T, Nakao, Y, Goetz, G, Yoshida, WY & Scheuer, PJ 2002, 'Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa', Journal of Organic Chemistry, vol. 67, no. 6, pp. 1760-1767. https://doi.org/10.1021/jo010176z
Kimura, Junji ; Takada, Yuuki ; Inayoshi, Tomoko ; Nakao, Youichi ; Goetz, Gilles ; Yoshida, Wesley Y. ; Scheuer, Paul J. / Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 6. pp. 1760-1767.
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