Molecules (Jun 2021)

Roseabol A, a New Peptaibol from the Fungus <i>Clonostachys rosea</i>

  • Chang-Kwon Kim,
  • Lauren R. H. Krumpe,
  • Emily Smith,
  • Curtis J. Henrich,
  • Isaac Brownell,
  • Karen L. Wendt,
  • Robert H. Cichewicz,
  • Barry R. O’Keefe,
  • Kirk R. Gustafson

DOI
https://doi.org/10.3390/molecules26123594
Journal volume & issue
Vol. 26, no. 12
p. 3594

Abstract

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A new 11 amino acid linear peptide named roseabol A (1) and the known compound 13-oxo-trans-9,10-epoxy-11(E)-octadecenoic acid (2) were isolated from the fungus Clonostachys rosea. Combined NMR and MS analysis revealed that roseabol A (1) contained amino acid residues characteristic of the peptaibol family of peptides such as isovaline, α-aminoisobutyric acid, hydroxyproline, leucinol, and an N-terminal isovaleric acid moiety. The amino acid sequence was established by a combination of NMR studies and tandem MS fragmentation analyses, and the absolute configurations of the constituent amino acids of 1 were determined by the advanced Marfey’s method. Compound 2 showed inhibitory activity against Merkel cell carcinoma, a rare and difficult-to-treat type of skin cancer, with an IC50 value of 16.5 μM.

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