Brevisulcatic acids, marine ladder-frame polyethers from the red tide dinoflagellate Karenia brevisulcata in New Zealand

Org Lett. 2014 Nov 21;16(22):5850-3. doi: 10.1021/ol502700h. Epub 2014 Oct 30.

Abstract

The isolation and structural determination of new marine ladder-frame polyethers, brevisulcatic acids-1 (1) and -4 (2) are reported. Brevisulcatic acids were isolated from the dinoflagellate Karenia brevisulcata, which was identified as the causative species of a major red tide event in New Zealand in 1998. The ether ring composition and a β-hydroxy, γ-methylene valeric acid side chain of 1 and 2 are common, but 2 has a γ-lactone as the 5-membered A-ring while 1 is the seco acid analogue. Compound 2 has structural and bioactivity similarities to brevetoxin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dinoflagellida / chemistry*
  • Ethers / chemistry
  • Harmful Algal Bloom
  • Marine Biology
  • Marine Toxins / chemistry*
  • Marine Toxins / isolation & purification*
  • Molecular Structure
  • New Zealand
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxocins / chemistry*
  • Oxocins / isolation & purification*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Ethers
  • Marine Toxins
  • Oxocins
  • brevisulcatic acid
  • Brevetoxin A