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gjtglATINGCIA'I ya Grail'9<PI~~ Proceedings of the Third nternationa Conference on Ciguatera Fish Poisoning n x a' 1 RRR e 0 Edited by T. R. Tosteson OcThomas R. Tosteson 1992. All rightsreserved. Production Credits Proofreading;Carmen Tosteson, Val Hensley Designand Layout: Alexis Tosteson Garcia, Angel An.ibal Escobar Cover Art: Bonnie Dennis Bower CoverDesign: Angel Anibal Fscobar ISBK 0-92 l 317-35-2 PolysciencePublications, inc. MorinHeights, Quebec, Canada Printed in Canada. Contents Preface Acknowledgements vu Chemistry of Fish artd Dirtoflagellate Toxins Structure Determination of Ciguatoxin of Moray Eels and Garrrbierdiscus toxicus. T. Yasumoto,M. Murata, Y. Ishibashi, M. Fukui and A.M. Legrand Extraction and Purification of Toxic Fractions From Barracuda 13 Sphyraerra barracuda! Implicated in Ciguatera Poisoning. Pedro M. Gamboa,Douglas L. Park, and Jean-MareFrerny Characterizationof Ciguatoxins from Different Fish Speciesand Wild Gambierdiscustoxicus. A-M. Legrand, M. Fukui, P. Cruchet, Y. Ishibashi and T. Yasumoto Brevetoxinsand RelatedPolymeric Ether Toxins: 33 Structuresand 8iosynthesis. Y. Shimizu, A, V. Krishna Prasad, H-N. Chou, G. Wresnsford, and M. Alarn Pharmacologyand Toxicology Effectsof Toxins on the Voltage-GatedVa Channel. 47 M. T, Tosteson PathomorphologicalStudies on ExperimentalMaitotoxicosis 55 and Ciguatoxicosisin Mice. K. Terao, E. Ito and T. Yasurnoto Mechanismsof Pharmacologicaland Toxicological Action 7I of Ciguatoxin and Maitotoxin. Y. Ohizumi Inhibition of SkeletalMuscle Responseto Acetylcholine 79 by Dinoflagellate and Ciguatoxic Fish Extracts. G. Escalona de Motta, J,A. Mercado, T.R. Tosteson and D.L. Ballantine CaribbeanCiguatera and Polyether DinoflagellateToxins: 89 Correlationof BarracudaCiguatoxins with StandardToxins. T.R. Tosteson,R.A. Edward and D.G. Baden ComputationalModeling of the PolyetherLadder 103 ToxinsBrevetoxin and Ciguatoxin. D. G. Baden, K. S. Rein, M. Kinoshita and R. F. Gawley Antibody Production and Developmentof a 115 Radioimmunoassayfor the PbTx-2-TypeBrevetoxins. M. A. Poli and J. F. Hewetson Ecology Excretionof Ciguatoxin from Moray Eels Muraenidae! 131 of the Central Pacific. R,J,Lewis, M. Sellin, R. Street,M.J. Holmes and N.C. Gillespie SeasonalAbundance and Toxicity of Gambierdiscustoxicus 145 Adachi et Fukuyo from 0'ahu, 1 lawai'i. E.J.McCaffrey, M.M,K. Shimizu, P.J.Scheuer and J,T. Miyahara SocietalImpact Public Health, Epiderniologicaland SocioeconomicPatterns 157 of Ciguaterain Tahiti. R. Bagnis,A. Spiegel,L Nguyen and R. Plichart Ciguatera:Clinical, Epiderniologicaland 169 Anthropo!ogica1 Aspects. P. Alvarez, C. Duval, T, Colon, G. Gonzalves, E. Martinez, J.Gomez, L. Cornpres,N. Pina and P.L.Castellanos How CiguateraAffects Canadians 181 E.C.D. Todd Reporton Ciguatera Fish Poisoning, Owia, November 23, 1985 197 K. Morris LegalAspects of CiguateraFish Poisoning in PuertoRico 201 J V. Biaggi Preface Ciguaterafish poisoningis a humanhealth problem that affectsall per- sonsliving in tropicalseas for whommarine fish representa significantsource of food.Ciguatera traditionally was limited to tropicalregions, however, modernimprovements in refrigeration and transport have augmented com- rnercialization of tropicalreef fishes and increased the frequency of thistype of fish poisoningin temperateportions of theearth Sincethe early reports of this poisoningin thetropical Pacific in the17th century, ciguatera has come to have an impact of global proportions, A broad and detailed treatment of the present status of researchon ciguaterafish poisoning is givenin thisvolume in 18papers presented at the Third InternationalConference on CiguateraFish Poisoningheld in I.a Parguera,Puerto Rico, April 30 throughMay 5, 1990.Laboratories, agencies and universitiesrepresented at this Conferencestretched from Australia,Ja- panand the islands of thesouth Pacific to Hawaii,the United States, Canada and throughthe islandsof the Caribbeanto Franceand the Mediterranean Sea.The Proceedings are divided into four sectionscovering; I! thechemis- try of fishand dinoflagellate toxins, ! thepharmacology and toxicology of ciguatoxicfish and dinoflagellatetoxins, including the actionof thesetoxins on membranechannels, their pathomorphologicaleffects on the organsand tissuesof the mouse,and a correlationof toxin potency with computer gener- atedconformational models of thesetoxins, ! ecologicaland fisheries aspects of ciguateraand the toxicdinoflagellate vectors of this poisoning,and ! the societalimpact of ciguaterain FrenchPolynesia, Canada, the DominicanRe- public, PuertoRico and St, Vincentsand Grenadines.These presentations addressglobal issuesdealing with epidemiology,public health,socioeco- nomicand legalaspects of ciguaterafish poisoning,a review of past and current trends, with a description of local and international programs pres- entlybeing implemented to dealwith ciguaterain theseareas. We hope that this volume will be of use to researchscientists working in this field as well as professionalsand studentsin fisheriesand public health interestedin the origin and impact of ciguatera fish poisoning. It would be difficult to name all of the personswho contributed to the successof the Third International Conferenceon CiguateraFish Poisoningancl theproduction of theseProceedings. Thanks are due to all of thecontributors to the Proceedingsfor their help in manuscript review,encouraging comments and patiencewith this process.Special gratitude goes to Mr. Alexis E. Tosteson,Administrative Director of the Conference,for his efforts and dili- gencein the preparationof theseProceedings La Parguera Puerto Rico T.R. Tosteson Acknowledgements Variousorganizattons contributed to the Third InternationalConference on CiguateraFish Poisoningand to the preparationof theseProceedings. We would like to acknowledgethe following: SPOnSOrS U.S. Army ResearchOffice U. S.Army ChemicalResearch, Development and EngineeringCenter SeaGrant College Program of the Universityof PuertoRico National SeaCrant CollegeProgram COntributorS Fundacion Educativa Ana G. Mt'.ndez CaribbeanFishery ManagementCouncil IntergovernmentalOceanographic Commission of Unesco FxperimentalProgram to StimulateCompetitive Research in PuertoRico Facultyof Arts k Sciences,Mayaguez Campus, University of PuertoRico Agricultural DevelopmentAdministration, Department of Agriculture, Commonwealth of Puerto Rico Centerfor the Enhancementof Teaching,University of PuertoRico BancoPopular de Puerto Rico Serviciosde Segurosde Salud de Puerto Rico Corporation for the TechnologicalDevelopment of Tropical Resources, Commonwealth of Puerto Rico Chiral Corporation Upjohn Pharmaceutical RegionalCo-ordinating Unit of theCaribbean Environment Program of the United Nations Environment Program,Kingston, jamaica This publicationis a result,in part, of funds sponsoredby the U, S, Army Research Otfice, Grant Num, DAAL03-89-G-011?and NOAA, National Sea Grant College ProgramOffice NSGCPO!,Department of Commerce,under Grant No. UPR-SG-04- F-158-44030 Project No. ti/C-74-10!. Opiruons,interpretations, conclusions, and recommendationsare those of the authors and are not necessarilyendorsed by sponsoringand contributing agenciesand organizations. Recommendationsare those of the authors and are not necessarily endorsedby sponsonng and contributing agenciesand organizations. Chemistry of Fish and Dinof lag ellate Toxins Structure Determination of Ciguatoxin of Moray Eels and Garrfbierdi sees toxicus T. Yasurnoto', M. Murata', Y, lshibashi', M. Fukui' and A.M. Legrand2 1Facultyof Agriculture,Tohoku University, 1-1 Tsutsumidori- Amarniyamachi,Aobaku, Sendai 981, Japan. InstitutTerritorial de RecherchesMc'dicales Louis Malarde, Papeete,Tahiti, French Polynesia ABSTRACT Ciguatoxinisolated from visceraof the morayeel Gyrnnofhorax javanicus and its congener tentativecodename CTX-4B! isolated from the causative dinoflagellate Gambierdiscustoxicus were subjectedto structure eluci- dation. The molecular formulae of CslIHssOt9and C6sHs40~swere determined for ciguatoxinand CTX-48respectively, by HR-FABMSand ~H NMR mea- surements.~H NMR signalsof protonsaround a nine-memberedring were broadenedor disappeareddue to a slowconformational change of the ring, but spectraquality was improved by measuringat low temperature.By exten- sive use of rH NMR 2D-correlation and NOE experimentscarried out on 0.35 rng of ciguatoxinand 0,74 mg of CTX-48,the two toxinswere toundto have brevetoxin-likepolyether structures comprised of thirteenrings /6/6/7/7/ 9/7/6/8/6/7/6-spiro-5!. CTX-4Bwas in a formless oxidized than ciguatoxin at two terminals of the molecule. Their relative stereochemistries,except for C2of ciguatoxin,were clarified by detailedanalyses of 'H NMR NOEexperi- ments.The primary alcoholat the terminal of the ciguatoxinmolecule suggestedits usefulnessfor preparinga flourescentderivative or a toxin- proteinconjugate to be used for immunization, INTRODUCTION Ciguatoxin CTX! is a termfirst proposedby Scheuerfor the principal toxin of the red snapperLutjanus bohar and then for the toxin in the liver of the moray eel Gymnofhorax =Lychodontis! javanicus'~. The purifled toxin was obtainedas fine crystals and suggestedby mass spectralmeasurements to have a molecular formula of either C53H~NOq4112.2! or Cs4H7s024 111.2!. The polyethernature of the molecule was indicated by 'H NMR measurements. However, the chemical structure of the toxin has remained undetermineddue to the extreme difhculty in obtainingthe toxin as well as the complexstructure of themolecule, The toxinwas presumed to be acquiredby
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