Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 14, Pages 5209-5212Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja500128u
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Funding
- Japan Society for the Promotion of Science
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Ministry of Health, Labour and Welfare of Japan
- Suntory Institute for Bioorganic Research
- Grants-in-Aid for Scientific Research [24102515, 24102517, 25702048] Funding Source: KAKEN
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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.
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