Cyclohexadepsipeptides of the isaridin class from the marine-derived fungus Beauveria felina EN-135

J Nat Prod. 2014 May 23;77(5):1164-9. doi: 10.1021/np4011037. Epub 2014 Apr 17.

Abstract

Three new cyclohexadepsipeptides of the isaridin class including isaridin G (1), desmethylisaridin G (2), and desmethylisaridin C1 (3), along with three related known metabolites (4-6), were isolated and identified from the marine bryozoan-derived fungus Beauveria felina EN-135. The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis, and the structures and absolute configurations of compounds 1-3 were confirmed by single-crystal X-ray diffraction analysis. The crystal structures showed the presence of β-turns for the Tyr(3)/N-Me-Val(4) and Phe(3)/N-Me-Val(4) amide bonds in compounds 2 and 3, respectively, in the cis conformations, which were opposite other reported isaridins. The conformations of the HMPA(1)-Pro(2) amide bond in compound 2 are different in the solution and in the crystal structures, which showed trans and cis geometries, respectively, while compounds 1 and 3 do not exhibit this phenomenon. Each of the isolated compounds was evaluated for antimicrobial activity and brine shrimp lethality. Compound 3 exhibited antibacterial activity against E. coli with an MIC value of 8 μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Artemia / drug effects
  • Beauveria / chemistry*
  • Crystallography, X-Ray
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology*
  • Edwardsiella tarda / drug effects
  • Escherichia coli / drug effects
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects
  • Stereoisomerism
  • Vibrio / drug effects

Substances

  • Anti-Bacterial Agents
  • Depsipeptides
  • isaridin F