Characterisation of multiple Caribbean ciguatoxins and congeners in individual specimens of horse-eye jack (Caranx latus) by high-performance liquid chromatography/mass spectrometry

Toxicon. 2002 Jul;40(7):929-39. doi: 10.1016/s0041-0101(02)00088-0.

Abstract

We studied the variation in toxin profiles of purified extracts of 10 individual specimens and two pools of ciguateric Caranx latus. High-performance liquid chromatography/mass spectrometry (HPLC/MS) identified in all individual samples at least seven Caribbean ciguatoxins (C-CTXs) comprising C-CTX-1 and its epimer C-CTX-2 ([M+H](+) m/z 1141.58), and five new C-CTX congeners with pseudo-molecular ions at m/z 1141.58, 1143.60, 1157.57, 1159.58, and 1127.57. In some samples, additional C-CTX isomers were detected with [M+H](+) ions at m/z 1141.58 (two), 1143.60 (one) and 1157.57 (two). The two low-toxic pools contained only four to six ciguatoxins. The comparison in relative proportions of four different mass classes ([M+H](+) at m/z 1141, 1143, 1157 and 1127) showed that the group at m/z 1157 increased (2-20%) with flesh toxicity. More than 80% of group m/z 1141 comprised C-CTX-1, C-CTX-2 and their isomer C-CTX-1a whose level in this group correlated with fish toxicity. Contrary to low-toxic fishes, high-risk specimens had C-CTX-1 levels <50% and were subjected to large losses of activity on purification indicating that unstable ciguatoxins were present. A possible conversion of C-CTX-1 into C-CTX-1a was identified when flesh was cooked, without changes in toxicity. In conclusion, HPLC/MS characterised 12 C-CTXs accumulated by C. latus at variable levels.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Atlantic Ocean
  • Biological Assay
  • Chromatography, High Pressure Liquid / methods*
  • Ciguatoxins / classification
  • Ciguatoxins / isolation & purification*
  • Ciguatoxins / toxicity
  • Fishes, Poisonous / metabolism*
  • Foodborne Diseases
  • Male
  • Mice
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / methods*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Ciguatoxins