Identification of pectenotoxin-11 as 34S-hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand

Chem Res Toxicol. 2006 Feb;19(2):310-8. doi: 10.1021/tx050240y.

Abstract

A new pectenotoxin, which has been named pectenotoxin-11 (PTX11), was isolated from the dinoflagellate Dinophysis acuta collected from the west coast of New Zealand. The structure of PTX11 was determined as 34S-hydroxypectenotoxin-2 by tandem mass spectrometry and UV and NMR spectroscopy. PTX11 appears to be only the third pectenotoxin identified as a natural biosynthetic product from algae after pectenotoxin-2 and pectenotoxin-12. The LD50 of PTX11 determined by mouse intraperitoneal injection was 244 microg/kg. The LD(min) of PTX11 in these experiments was 250 microg/kg. No signs of toxicity were recorded in mice following an oral dose of PTX11 at 5000 microg/kg. No diarrhea was observed in any of the animals administered with the test substance by either route of administration. Unlike pectenotoxin-2 (PTX2), PTX11 was not readily hydrolyzed to its corresponding seco acid by enzymes from homogenized green-lipped mussel (Perna canaliculus) hepatopancreas.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dinoflagellida / chemistry*
  • Furans / chemistry*
  • Furans / isolation & purification*
  • Injections, Intraperitoneal
  • Lethal Dose 50
  • Macrolides
  • Magnetic Resonance Spectroscopy
  • Marine Toxins / administration & dosage
  • Marine Toxins / chemistry*
  • Marine Toxins / toxicity
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • New Zealand
  • Pyrans / chemistry*
  • Pyrans / isolation & purification*
  • Sensitivity and Specificity
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Time Factors

Substances

  • Furans
  • Macrolides
  • Marine Toxins
  • Pyrans
  • pectenotoxin 2