Nocardiamides A and B, two cyclohexapeptides from the marine-derived actinomycete Nocardiopsis sp. CNX037

J Nat Prod. 2013 Apr 26;76(4):694-701. doi: 10.1021/np400009a. Epub 2013 Apr 15.

Abstract

Two new cyclic hexapeptides, nocardiamides A (1) and B (2), were isolated from the culture broth of marine-derived actinomycete CNX037 strain that was identified as a Nocardiopsis species. The planar structures of nocardiamides A (1) and B (2) were assigned on the basis of 1D and 2D NMR and HRESIMS spectroscopic analyses. Their absolute configurations were deduced by the advanced Marfey's method and chiral-phase HPLC analysis. The challenge of locating two d- and one l-valine residue in 1 and 2 was accomplished by total synthesis using solid-phase peptide synthetic methods. Both 1 and 2 showed negligible antimicrobial activities against seven indicator strains and exhibited no cytotoxicity against HCT-116.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Humans
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nocardia / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Valine / chemistry

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Peptides, Cyclic
  • nocardiamide A
  • nocardiamide B
  • Valine