Structure and biological activity of 8-deoxyheronamide C from a marine-derived streptomyces sp. Heronamides target saturated hydrocarbon chains in lipid membranes

Ryosuke Sugiyama, Shinichi Nishimura, Nobuaki Matsumori, Yuta Tsunematsu, Akira Hattori, Hideaki Kakeya

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Polyene macrolactams are a class of microbial metabolites, many of which show potent biological activities with unidentified modes of action. Here we report that 8-deoxyheronamide C, a new 20-membered polyene macrolactam from a marine-derived actinomycete Streptomyces sp., is a unique membrane binder. 8-Deoxyheronamide C showed a characteristic sensitivity profile against fission yeast sterol mutant cells, indicating that the metabolite targets cell membranes. We detected tight physical interaction between heronamides including 8-deoxyheronamide C and heronamide C and saturated hydrocarbon chains in lipid membranes using surface plasmon resonance experiments. We further show that heronamides induced abnormal cell wall morphology in fission yeast probably by perturbing the structure of membrane microdomains. This work will accelerate the biological and medical investigation of polyene macrolactams.

Original languageEnglish
Pages (from-to)5209-5212
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number14
DOIs
Publication statusPublished - Apr 9 2014
Externally publishedYes

Fingerprint

Streptomyces
Membrane Lipids
Hydrocarbons
Bioactivity
Polyenes
Metabolites
Yeast
Schizosaccharomyces
Membranes
Surface plasmon resonance
Cell membranes
Membrane Microdomains
Binders
Surface Plasmon Resonance
Actinobacteria
Sterols
Cells
Cell Wall
Cell Membrane
heronamide C

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Structure and biological activity of 8-deoxyheronamide C from a marine-derived streptomyces sp. Heronamides target saturated hydrocarbon chains in lipid membranes. / Sugiyama, Ryosuke; Nishimura, Shinichi; Matsumori, Nobuaki; Tsunematsu, Yuta; Hattori, Akira; Kakeya, Hideaki.

In: Journal of the American Chemical Society, Vol. 136, No. 14, 09.04.2014, p. 5209-5212.

Research output: Contribution to journalArticle

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