Psychrophilins E-H and versicotide C, cyclic peptides from the marine-derived fungus Aspergillus versicolor ZLN-60

J Nat Prod. 2014 Oct 24;77(10):2218-23. doi: 10.1021/np500469b. Epub 2014 Sep 23.

Abstract

Four new cyclic peptides, psychrophilins E-H (1-4), possessing a rare amide linkage between the carboxylic acid in anthranilic acid (ATA) and the nitrogen from an indole moiety, along with a new ATA-containing hexapeptide, versicotide C (5), were obtained from the culture of the marine-derived fungus Aspergillus versicolor ZLN-60. The structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, TDDFT ECD calculations, and Marfey's method. Versicotide C (5) is the first natural cyclic hexapeptide containing two anthranilic acids. Compounds 1-5 were not cytotoxic, and compound 3 showed potent lipid-lowering effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus / chemistry*
  • Crystallography, X-Ray
  • Lipid Regulating Agents / metabolism
  • Marine Biology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology

Substances

  • Lipid Regulating Agents
  • Peptides, Cyclic
  • versicotide C