Eudesmacarbonate, a Eudesmane-Type Sesquiterpene from a Marine Filamentous Cyanobacterial Mat (Oscillatoriales) in the Florida Keys

J Nat Prod. 2020 Jun 26;83(6):2030-2035. doi: 10.1021/acs.jnatprod.0c00203. Epub 2020 May 28.

Abstract

A new, cyclic carbonate eudesmane-type sesquiterpene, eudesmacarbonate (1), was isolated from marine filamentous cyanobacterial mats associated with apparent ingestion-related intoxications of captive bottlenose dolphins in the Florida Keys. Sequencing of 16S rDNA revealed that mats were composed of closely related Oscillatoriacean species including a previously undocumented species of Neolyngbya. The structure of 1 was elucidated by (+)-HRESIMS, 1D and 2D NMR, single-crystal X-ray diffraction, and vibrational circular dichroism data. Toxicity of 1 was assessed in the zebrafish embryo/larval model, and 1 was found to exhibit effects qualitatively similar to those observed for the known neurotoxin brevetoxin-2 and consistent with neurobehavioral impairment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Cyanobacteria / chemistry*
  • Embryo, Nonmammalian
  • Florida
  • Larva
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Neurotoxicity Syndromes / psychology*
  • Neurotoxins / toxicity*
  • Sesquiterpenes / pharmacology*
  • Sesquiterpenes, Eudesmane / toxicity*
  • X-Ray Diffraction
  • Zebrafish

Substances

  • Neurotoxins
  • Sesquiterpenes
  • Sesquiterpenes, Eudesmane
  • eudesmane