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:10.3390/molecules26123594

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

Affiliations

Chang-Kwon Kim: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA
Lauren R. H. Krumpe: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA
Emily Smith: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA
Curtis J. Henrich: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA
Isaac Brownell: Dermatology Branch, National Institute of Arthritis and Musculoskeletal and Skin Diseases, Bethesda, MD 20893, USA
Karen L. Wendt: Natural Products Discovery Group, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
Robert H. Cichewicz: Natural Products Discovery Group, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
Barry R. O’Keefe: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA
Kirk R. Gustafson: Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA

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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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