Wewakazole B, a Cytotoxic Cyanobactin from the Cyanobacterium Moorea producens Collected in the Red Sea

J Nat Prod. 2016 Apr 22;79(4):1213-8. doi: 10.1021/acs.jnatprod.6b00051. Epub 2016 Mar 16.

Abstract

A mass spectrometry (MS)-guided isolation has led to the purification of a new cyanobactin, wewakazole B (1), along with the known compound curacin D from a Red Sea Moorea producens. The planar structure of 1 was elucidated using a combination of NMR and MS techniques. After ozonolysis and acid hydrolysis, the absolute configurations of the amino acid components of 1 were determined by chiral-phase LC-MS and HPLC analyses. Notably, compound 1 exhibited cytotoxic activity toward human MCF7 breast cancer cells (IC50 = 0.58 μM) and human H460 lung cancer cells (IC50 = 1.0 μM) and was also found to be inactive in a siderophore assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Indian Ocean
  • Lyngbya Toxins / chemistry
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / pharmacology*
  • Thiazoles / pharmacology

Substances

  • Antineoplastic Agents
  • Depsipeptides
  • Lyngbya Toxins
  • Peptides, Cyclic
  • Thiazoles
  • wewakazole
  • curacin D