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Purification and characterization of ciguatoxins from moray eel (Lycodontis javanicus, Muraenidae).
Toxicon. 1991; 29(9):1115-27.T

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 micrograms) was comparable by both 1H nuclear magnetic resonance (1H NMR) and mass spectroscopy (MH+ m/z = 1111) to ciguatoxin isolated previously from moray eels. CTX-2 (280 micrograms) and CTX-3 (100 micrograms) 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. 1H 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 1H 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 micrograms/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 [3H]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.

Authors+Show Affiliations

Southern Fisheries Research Centre, QDPI, Deception Bay, Qld, Australia.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

1665604

Citation

Lewis, R J., et al. "Purification and Characterization of Ciguatoxins From Moray Eel (Lycodontis Javanicus, Muraenidae)." Toxicon : Official Journal of the International Society On Toxinology, vol. 29, no. 9, 1991, pp. 1115-27.
Lewis RJ, Sellin M, Poli MA, et al. Purification and characterization of ciguatoxins from moray eel (Lycodontis javanicus, Muraenidae). Toxicon. 1991;29(9):1115-27.
Lewis, R. J., Sellin, M., Poli, M. A., Norton, R. S., MacLeod, J. K., & Sheil, M. M. (1991). Purification and characterization of ciguatoxins from moray eel (Lycodontis javanicus, Muraenidae). Toxicon : Official Journal of the International Society On Toxinology, 29(9), 1115-27.
Lewis RJ, et al. Purification and Characterization of Ciguatoxins From Moray Eel (Lycodontis Javanicus, Muraenidae). Toxicon. 1991;29(9):1115-27. PubMed PMID: 1665604.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Purification and characterization of ciguatoxins from moray eel (Lycodontis javanicus, Muraenidae). AU - Lewis,R J, AU - Sellin,M, AU - Poli,M A, AU - Norton,R S, AU - MacLeod,J K, AU - Sheil,M M, PY - 1991/1/1/pubmed PY - 1991/1/1/medline PY - 1991/1/1/entrez SP - 1115 EP - 27 JF - Toxicon : official journal of the International Society on Toxinology JO - Toxicon VL - 29 IS - 9 N2 - 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 micrograms) was comparable by both 1H nuclear magnetic resonance (1H NMR) and mass spectroscopy (MH+ m/z = 1111) to ciguatoxin isolated previously from moray eels. CTX-2 (280 micrograms) and CTX-3 (100 micrograms) 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. 1H 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 1H 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 micrograms/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 [3H]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. SN - 0041-0101 UR - https://www.unboundmedicine.com/medline/citation/1665604/Purification_and_characterization_of_ciguatoxins_from_moray_eel__Lycodontis_javanicus_Muraenidae__ L2 - https://linkinghub.elsevier.com/retrieve/pii/0041-0101(91)90209-A DB - PRIME DP - Unbound Medicine ER -