Structure Elucidation and in Vitro Toxicity of New Azaspiracids Isolated from the Marine Dinoflagellate Azadinium poporum

Mar Drugs. 2015 Oct 30;13(11):6687-702. doi: 10.3390/md13116687.

Abstract

Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids. Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively. The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by ¹H- and (13)C-NMR. Using the Jurkat T lymphocyte cell toxicity assay, (1) and (2) were found to be 6- and 3-fold less toxic than AZA-1, respectively.

Keywords: NMR; lipophilic marine biotoxins; shellfish poisoning.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dinoflagellida / metabolism*
  • Humans
  • Jurkat Cells
  • Leukemia, T-Cell / metabolism
  • Magnetic Resonance Spectroscopy
  • Marine Toxins / chemistry
  • Marine Toxins / isolation & purification*
  • Marine Toxins / toxicity
  • Republic of Korea
  • Species Specificity
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / toxicity
  • Toxicity Tests

Substances

  • Marine Toxins
  • Spiro Compounds
  • azaspiracid