Purification and Characterization of Ciguatoxins From Moray Eel (Lycodontis-Javanicus, Muraenidae)

Lewis, RJ, Sellin, M, Poli, MA, Norton, RS, Macleod, JK and Sheil, MM (1991) Purification and Characterization of Ciguatoxins From Moray Eel (Lycodontis-Javanicus, Muraenidae). Toxicon, 29 9: 1115-1127. doi:10.1016/0041-0101(91)90209-A

Author Lewis, RJ
Sellin, M
Poli, MA
Norton, RS
Macleod, JK
Sheil, MM
Title Purification and Characterization of Ciguatoxins From Moray Eel (Lycodontis-Javanicus, Muraenidae)
Journal name Toxicon   Check publisher's open access policy
ISSN 0041-0101
Publication date 1991-01-01
Year available 1991
Sub-type Article (original research)
DOI 10.1016/0041-0101(91)90209-A
Open Access Status DOI
Volume 29
Issue 9
Start page 1115
End page 1127
Total pages 13
Place of publication OXFORD
Language eng
Abstract Viscera (48.3 kg) from moray eels (Lycodontis javanicus) collected in a ciguatera endemic area were extracted and the ciguatoxins characterized. Three major ciguatoxins, CTX-1, CTX-2 and CTX-3, were isolated and purified to homogeneity on reverse phase high performance liquid chromatography. Several minor toxins were also detected. CTX-1 (490-mu-g) was comparable by both H-1 nuclear magnetic resonance (H-1 NMR) and mass spectroscopy (MH+ m/z = 1111) to ciguatoxin isolated previously from moray eels. CTX-2 (280-mu-g) and CTX-3 (100-mu-g) were less polar ciguatoxins not previously characterized. CTX-2 and CTX-3 differed from CTX-1 by 16 mass units, suggesting that they were less oxygenated analogues. H-1 NMR revealed that the hydroxyl at C54 in CTX-1 was absent in CTX-2 and CTX-3. An additional change in the chemistry of CTX-2 compared to CTX-1 and CTX-3 was also suggested on the basis of H-1 NMR, indicating that CTX-2 may arise from a different precursor to CTX-1. CTX-3 is likely to be an intermediate in the oxidation of a gambiertoxin (sodium channel toxins from Gambierdiscus toxicus) to CTX-1. The i.p. LD50 values for CTX-1, CTX-2 and CTX-3 were 0.25, 2.3 and 0.9-mu-g/kg, respectively. The signs induced in mice by the ciguatoxins were similar, except that CTX-2 and CTX-3 induced hind-limb paralysis that was absent with CTX-1. Each ciguatoxin was potent orally. CTX-1, CTX-2 and CTX-3 competitively inhibited the binding of [H-3] brevetoxin-3 to voltage-dependent sodium channels with relative potencies qualitatively (but not quantitatively) comparable to mouse lethality. This study reveals that the relatively small chemical differences between CTX-1, CTX-2 and CTX-3 give rise to significant structure-activity and pharmacokinetic differences.
Keyword Gambierdiscus-Toxicus
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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