Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii

Shimpei Sumimoto, Arihiro Iwasaki, Osamu Ohno, Kosuke Sueyoshi, Toshiaki Teruya, Kiyotake Suenaga

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15 Citations (Scopus)

Abstract

Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.

Original languageEnglish
Pages (from-to)4884-4887
Number of pages4
JournalOrganic Letters
Volume18
Issue number19
DOIs
Publication statusPublished - 2016 Oct 7

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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