Laucysteinamide A, a Hybrid PKS/NRPS Metabolite from a Saipan Cyanobacterium, cf. Caldora penicillata

Mar Drugs. 2017 Apr 14;15(4):121. doi: 10.3390/md15040121.

Abstract

A bioactivity guided study of a cf. Caldora penicillata species, collected during a 2013 expedition to the Pacific island of Saipan, Northern Mariana Islands (a commonwealth of the USA), led to the isolation of a new thiazoline-containing alkaloid, laucysteinamide A (1). Laucysteinamide A is a new monomeric analogue of the marine cyanobacterial metabolite, somocystinamide A (2), a disulfide-bonded dimeric compound that was isolated previously from a Fijian marine cyanobacterium. The structure and absolute configuration of laucysteinamide A (1) was determined by a detailed analysis of its NMR, MS, and CD spectra. In addition, the highly bioactive lipid, curacin D (3), was also found to be present in this cyanobacterial extract. The latter compound was responsible for the potent cytotoxicity of this extract to H-460 human non-small cell lung cancer cells in vitro.

Keywords: blue-green alga; cyanobacteria; cytotoxicity; laucysteinamide A; thiazoline alkaloid.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology*
  • Carcinoma, Non-Small-Cell Lung / drug therapy
  • Cell Line, Tumor
  • Cyanobacteria / chemistry*
  • Cyanobacteria / metabolism*
  • Humans
  • Lipids / chemistry
  • Lipids / pharmacology
  • Lung Neoplasms / diet therapy
  • Micronesia
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Alkaloids
  • Lipids
  • Thiazoles
  • curacin D