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

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

*この研究の対応する著者

研究成果: Article査読

53 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1760-1767
ページ数8
ジャーナルJournal of Organic Chemistry
67
6
DOI
出版ステータスPublished - 2002 3 22
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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