Aplyronines D-H from the sea hare Aplysia kurodai: Isolation, structures, and cytotoxicity

Makoto Ojika, Hideo Kigoshi, Kiyotake Suenaga, Yoshifumi Imamura, Kohji Yoshikawa, Takeshi Ishigaki, Akira Sakakura, Tsuyoshi Mutou, Kiyoyuki Yamada

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Abstract

Five cytotoxic macrolides, aplyronines D-H (4-8), were isolated from the Japanese sea hare Aplysia kurodai. They are new congeners of the antitumor compound aplyronine A (1), which was previously isolated from the same organism. Their structures were determined by spectroscopic analysis (NMR and MS). The cytotoxicity of these new compounds was evaluated in comparison with that of aplyronines A-C (1-3), suggesting the importance of the 7-O-seryl ester group for mediating the potent cytotoxicity of aplyronines.

Original languageEnglish
Pages (from-to)982-987
Number of pages6
JournalTetrahedron
Volume68
Issue number4
DOIs
Publication statusPublished - 2012 Jan 28

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Keywords

  • Aplyronine
  • Cytotoxicity
  • Isolation
  • Marine natural product
  • Sea hare
  • Structure

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Ojika, M., Kigoshi, H., Suenaga, K., Imamura, Y., Yoshikawa, K., Ishigaki, T., Sakakura, A., Mutou, T., & Yamada, K. (2012). Aplyronines D-H from the sea hare Aplysia kurodai: Isolation, structures, and cytotoxicity. Tetrahedron, 68(4), 982-987. https://doi.org/10.1016/j.tet.2011.11.095