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Structural elucidation of super-active marine natural products

Research Project

Project/Area Number 07102002
Research Category

Grant-in-Aid for Specially Promoted Research

Allocation TypeSingle-year Grants
Review Section Chemistry
Research InstitutionTohoku University

Principal Investigator

YASUMOTO Takeshi  Tohoku University, Professor, 農学部, 教授 (20011885)

Co-Investigator(Kenkyū-buntansha) YAMASHITA Mari  Tohoku University, Technical Officer, 農学部, 教務職員 (50192430)
Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥161,000,000 (Direct Cost: ¥161,000,000)
Fiscal Year 1997: ¥26,000,000 (Direct Cost: ¥26,000,000)
Fiscal Year 1996: ¥30,000,000 (Direct Cost: ¥30,000,000)
Fiscal Year 1995: ¥105,000,000 (Direct Cost: ¥105,000,000)
Keywordsabsolute configurations / DSP toxins / spiramino acid / prymnesins / gymnodimin / lyngbyatoxin / TTX resistance / clupeotoxism / シガトキシン / マイトトキシン / イエッソトキシン / プリムネシン / パリトキシン / ヒガンフグ筋肉Naチャネル / フグのフグ毒耐性機構 / クルペオトキシズム / 有毒渦鞭毛藻 / 超活性海洋天然物 / ブレベトキシン新奇同族体 / ギムノジミン / ポリカバノシド / テトロドトキシン同族体 / パリトキシン同族体
Research Abstract

The results achieved in the present study are summarized as follows : Clupeotoxixm is caused by palytoxins produced by Ostreopsis siamensis 2) Marine turtle poisoning is caused by a cyanophyte toxin, lyngbyatoxin a 3) New toxins, carchatoxins, were isolated as the cause of shark poisoning 4) New toxins, spiramino acids, were isolated from Irish mussels 5) New brevetoxin analogs were isolated as the cause of neurotoxic shellfish poisoning 6) New polycavernoside analogs were isolated as the cause of Gracilaria poisoning in Guam 7) Novel imine-toxins, gymnodimines, produced by Gymnodinium sp. are accumulated in oysters 8) Dinophysis acuta produces seco acids of pectenotoxin-2 9) Protoceratium reticulatum and Linglodinium polyedrum were the sources of yessotoxin and its analog 10) New ciguatoxin analogs were determined 11) Structures of prymnesin-1 and -2, potent hemolysin-ichthyotoxins, were determined. 12)New tetrodotoxin analogs were determined 14) Absolute configurations were determined on ciguatoxin, maitotoxin, ganbierol, pectenotoxin, and dinophysistoxin 15) Absolute configurations of partial structures of prymnesin and gambieric acid were determined 16) The structure of polonicum toxin was confirmed by synthesis 17) Fluorometric-HPLC methods were developed for pectenotoxin-2, yessotoxins, and ciguatoxin-4A 17) Chemi-luminescence determination methods were developed for ciguatoxins and brevetoxins 19) Tritiation of okadaic acid and tetrodotoxin was achieved 20) Affinity of 13 tetrodotoxin analogs to rat brain synaptic membranes was determined 21) The primary structure of a voltage-dependent Na channel from pufferfish muscle was deduced by cloning and sequencing cDNA 22) A saxitoxin binding protein was isolated from pufferfish serum.

Report

(4 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (155 results)

All Other

All Publications (155 results)

  • [Publications] Patrizia Ciminiello: "Yessotoxin in mussels of the northem Adriatic Sea" Toxicon. 35(2). 177-183 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Isolation and structure of ciguatoxin-4A, a new cituatoxin precursor, from cultures of dinoflagellate Gambierdiscus toxicus and parrotfigh Scarus gibbus." Biosci. Biotech. Biochem.60(12). 2103-2105 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Emiko Ito: "Effects of repeated injection of palytoxin of lymphoid tissues in mice." Toxicon. 35(5). 679-680 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroko Ogura: "Synthetic of Ciguatoxin. Absolute Configuration of the C2 Hydroxy Group." Tetrahedron. 53(9). 3057-3072 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Two New Analogs of Yessotoxin, Homoyessotoxin and 45-Hydroxyhomoyessotoxin, Isolated from Mussels of the Adriatic Sea." Natural Toxins. 5(3). 107-110 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Fluorometric Measurement of Yessotoxins in Shellfish by High-pressure Liquid Chromatography" Biosci. Biotech. Biochem. 61(10). 1775-1777 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sasaki: "Identification of the Absolute Configuration of Pectenotoxin-6, a Polyrther Macrolide Compound, by NMR Spectroscopic Method Using a Chiral Anisotropic Reagent, Phenylglycine Methyl Ester." Biosci, Biotech, Biochem.61(10). 1783-1785 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideyuki Onodera: "New Saxitoxin Analogues From the Freshwater Filametous Cyanobacterium Lyngbya wollei." Natural Toxins. 5(4). 146-151 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Identification of Protoceratium reticulatum as the Biogenetic Origin of Yessotoxin." Natural Toxins. 5(4). 164-167 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "The Absolute Configuration of Ciguatoxin." J.Am.Chem.Soc.119(46). 11325-11326 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroshi Nagai: "Manauealides, Some of the Causative Agents of a Red Alga Gracilaria coronopifolia Poisoning in Hawaii." journal of NATURAL PRODUCTS. 60(9). 925-928 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Isolaton and Structures of New Ciguatoxin Analogs, 2,3-Dihydroxy CTX3C and 51-Hydroxy CTX3C, Accoumulated in Tropical Reef Fish." Tetrahedron Letters. 39. 1197-1198 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuya Murata: "Isolaton and Suructures of New Ciguatoxin Analogs, Brevetoxin B2, from Greenshell Mussels from New Zealand." Tetrahedron. 54. 735-742 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mari Yotsu Yamashita: "Synthesis and Confirmation of the Structures of Polonicumtoxins A,B,and C." Heterocylces.48. 79-93 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoji Igarashi: "Biological activities of prymnesin-2 isolated from a red tide alga Prymnesium parvum." Natural Toxins. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sasaki: "The Identification and Characterization of Pectenotoxin (PTX) 4 and PTX7 as Spiroketal Stereoisomers of Two Previously Reported Pectenotoxins" J.Organic Chemistry. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Bioactive Compounds from Marine Microalgae" Chimia. 52(印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sasaki: "Application of the Phenylglycine Methyl Ester to the Establishment of the Absolute Configuration of Dinophysistoxin-1, a Polyether Toxin Responsible for Diarrhetic Shellfish Poisoning" Enantiomer. 1(印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroyuki Ogino: "Toxicologic Evaluation of Yessotoxin" Natural Toxins. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Emiko Ito: "Effects of Repeated Injections of Palytoxin on Lymphold Tissues in Mice" Toxicon.35. 679-688 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroko Tohda.: "Unstable Expression of the Multi-Drug-Resistant Phennotype in chinese Hamster Ovary Cells Resistant to Okadaic Acid" Biochemical and Biophysical Research Communications. 232. 398-402 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Takai: "Inhibition of specific binding of okadaic" Biochem.J.306. 657-665 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Dietrich Mebs: "Further report on the occurrence of tetrodotoxin in Atelopus species (Family : Bufonidae)" Toxicon. 33(2). 246-249 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoji Igarashi: "Chemical studies on prymnesins isolated from Prymnesium parvum." In "Harmful Marine Algal Blooms" (P.Lassus, G.Arzul, E.Erard, P.Gentien and C.Marcaillou, eds.). Technique & Documentation-Lavoisier, Paris.303-308 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto, Masayuki Satake, Kiminori Sugiyama, Shu Ishida, Michio Murata, and Hideo Naoki: "Maitotoxin and other ciguatera toxins : from structures to determination." In "Harmful Marine Algal Blooms" (P.Lassus, G.Arzul, E.Erard, P.Gentien, C.Marcaillou, eds.). Technique & Documentation-Lavoisier, Paris.377-381 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hitoshi Ishida: "Brevetoxin B1, A new polyether marine toxin from the New Zealand shellfish, Austrovenus stutchburyi" Tetrahedron Lett.36(5). 725-728 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Determinations of marine toxins in foods" A.O.A.C.Intern.78(2). 574-582 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masaya Usami: "Palytoxin analogs from the dinoflagellate Ostreopsis siamensis." J.Am.Chem.Soc.117. 5389-5390 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Structural confirmation of maitotoxin based on complete ^<13>C NMR assignments and the three-dimensional PFG NOESY-HMQC spectrum" J.Am.Chem.Soc.117. 7019-7020 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ron L.Manger: "Detection of sodium channel toxins ; directed cytotoxicity assays of purified ciguatoxins, brevetoxins, saxitoxins, and seafood extracts" J.A.O.A.C.Intern.78(2). 521-527 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mari Yotsu-Yamashita: "Four new analogs of polycavernoside A." Tetrahedron Lett.36(31). 5563-5566 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tetsuya Seki: "Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate Gymnodinium sp." Tetrahedron Lett.36(39). 7093-7096 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akio Morohashi, Masayuki Satake, Kazuya Murata, Hideo Naoki, Heinrich F.Kaspar and Takeshi Yasumoto: "Brevetoxin B3, a new brevetoxin analog isolated from the greenshell mussel Perna canaliculus involved in neurotoxic shellfish poisoning in New Zealand" Tetrahedron Lett.36(49). 8995-8998 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Patrizia Ciminiello: "Determination of PSP toxins in mussels from the Adriatic Sea." Marine Pollution Bulletin. 30(11). 733-735 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mari Yotsu-Yamashita: "5,6,11-Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus." Tetrahedron Lett.36(51). 9329-9332 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Stereochemical assignment of the C35-C39 acyclic linkage in maitotoxin ; completion of stereochemical determination of C15-C134." Tetrahedron Lett.36(49). 9011-9014 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Fascal Boisier: "Fatal mass poisoning in Madagascar following ingestion of a shark (Carcharhinus leucas) : clinical and epidemiological aspects and isolation of toxins." Toxicon. 33(10). 1359-1364 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoji Igarashi: "Prymnesin-2 : A potent ichthyotoxic and hemolytic glycoside isolated from the red tide alga Prymnesium parvum." J.Am.Chem.Soc.118. 479-480 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Emiko Ito: "Morphological observations of diarrhea in mice caused by experimental ciguatoxicosis" toxicon. 34(1). 111-122 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Matomo Nishio: "Na^+ permeable channels induced by maitotoxin in guinea-pig single ventricular cells." Euro.J.Pharmacol.297. 293-298 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Nobuaki Matsumori: "Long-range carbon-proton coupling constants for stereochemical assignment of acyclic structures in natural products : configuration of the C5-C9 portion of maitotoxin" Tetrahedron Lett.37(8). 1269-1272 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] B.Q.Wu: "11-Oxo-tetrodotoxin and a specifically labelled ^3H-tetrodotoxin." Toxicon. 34(4). 407-416 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Aurella Tubaro: "A protain phosphatase 2A inhibition assay for a fast and sensitive assessment of pkadaic acid contamination in mussels." Toxicon. 34(7). 743-752 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroshi Nagai: "Aplysiatoxin and debromoaplysiatoxin as the causative agent of a red alga Gracilariacoronopifolia poisoning in Hawaii." Toxicon.34(7). 753-761 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Makoto Sasaki: "The complete structure of maitotoxin, I ; Stereochemistry of the C1-C14 side chain, Angew." Chem.Int.Ed.Engl.35. 1672-1675 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Makoto Sasaki: "The complete structure of maitotoxin, II ; Stereochemistry of the C135-C142 side chain and absolute configuration of the entire molecule. Angew." Chem.Int.Ed.Engl.35. 1675-1678 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Relative configuration of yessotoxin and isolation of two new analogs from toxic scallop" Tetrahedron Lett.37(33). 5955-5958 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Keiichi Konoki: "Blockade of MTX-induced Ca2+ influx in rat glioma C6 cells by alkylamines." J.Natural Toxin. 5(2). 209-217 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Chemical and etiological studies on tetrodotoxin and its analogs" J.TOXICOL.-TOXIN REVIEWS.15(2). 81-90 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Chemistry, etiology and determination methods of ciguatera toxins" J.OXICOL.-TOXIN REVIEWS. 15(2). 91-107 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Emiko Ito: "Intestinal injuries caused by experimental palytoxicosis in mice" Toxicon. 34(6). 643-652 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Lionel Glendenning: "Examination of the conformational properties of the prymnesin system : a computational chemistry approach" Bull.Chem.Soc.Jpn.69. 2253-2263 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Tubara: "Suitability of the MTT-Based cytotoxicity assay to detect okadaic acid contamination of mussel" toxicon. 34. 965-974 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Akasaka: "Fluorimetric determination of diarrhetic shellfish toxins in scallops and mussels by high-performance liquid chromatography" Journal of Chromatography A.729. 381-386 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Haruko Takahashi: "Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, Methoxy-(2-naphthyl) acetic acid" Tetrahedron Lett.37. 7087-7090 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Gary S.Bignami: "Antibodies to maitotoxin elicited by immunization with toxin-fragment conjugates" toxicon. 34. 1393-1397 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Chemical studies on the NSP toxins in the greenshell mussels from New Zealand" Harmful and Toxic Algal Blooms. Yasumoto T., Oshima, Y and Fukuyo, Y.(eds). 487-489 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tetsuya Seki: "Gymnodimine, a novel toxic imine isolated from the Foveaux strait oysters and Gymnodinium sp." Harmful and Toxic Algal Blooms. Yasumoto, T., Oshima, Y and Fukuyo, Y.(Eds). 495-498 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Lincoln Mackenzie: "Gymnodimine contamination of shellfish in New Zealand." Harmful and Toxic Algal Blooms. Yasumoto, T., Oshima, Y and Fukuyo, Y.(Eds). 97-100 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Niclas Johansson: "Toxin Production By Dinophysis Acuminata And D.Acuta Cells Grown Under Nutrient Sufficient And Deficient Condition" Harmful and Toxic Algal Blooms.Yasumoto, T., Oshima, Y and Fukuyo, Y.(Eds). 277-280 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kiyoshi Terao: "Effects of Prymnesin Maitotoxin And Gymnodimine on the Structure of Gills of small Fish Akahire" Tanichthys Albonubes LIN.Harmful and Toxic Algal Blooms. Yasumoto, T., Oshima, Y.and Fukuyo, Y.(Eds). 479-481 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Onodera: "Screening of Paralytic Shellfish Toxins in Freshwater Cyanobacteria and Chemical Confirmation of the Toxins in Cultured ANABAENA CIRCINALIS from Australia" Harmful and Toxic Algal Blooms. Yasumoto, T., Oshima Y.and Fukuyo, Y.(Eds). 563-566 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroko Tohda: "Unstable Expression of the Multi-Drug-Resistant Phennotype in chinese Hamster Ovary Cells Resistant to Okadaic Acid" Biochemical and Biophysical Research Communications. 232. 398-402 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Patrizia Ciminiello: "Yessotoxin in mussels of the northern Adriatic Sea" Toxicon. 35(2). 177-183 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Isolation and structure of ciguatoxin-4A,a new cituatoxin precursor, from cultures of inoflagellate Gambierdiscus toxicus and parrotfigh Scarus gibbus." Biosci.Biotech.Biochem.60. 2103-2105 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Two New Analogs of Yessotoxin, Homoyessotoxin and 45-Hydroxyhomoyessotoxin, Isolated from Mussels of the Adriatic Sea" Natural Toxins. 5(3). 107-110 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroko Ogura: "Synthetic Study of Ciguatoxin. Absolute Configuration of the C2 Hydroxy Group" Tetrahedron. 53(9). 3057-3072 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Emiko Ito: "Effects of repeated injection of palytoxin of lymphoid tissues in mice" oxicon. 35(5). 679-688 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Fluorometric Measurement of Yessotoxins in Shellfish by High-pressure Liquid Chromatograohy" Biosci.Biotech.Biochem.61(10). 1775-1777 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sakaki: "Identification of the Absolute Configuration of Pectenotoxin-6, a Polyrther Macrolide Compound, by NMR Spectroscopic Method Using a Chiral Anisotropic Reagent, Phenylglycine Methyl Ester" Biosci.Biotech.Biochem.61(10). 1783-4785 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "The Absolute Configuration of Ciguatoxin" J.Am.Chem.Soc.119(46). 11325-11326 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Identification of Protoceratiumreticulatum as the Biogenetic Origin of Yessotoxin" Natural Toxins. 5(4). 164-167 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideyuki Onodera: "New Saxitoxin Analogues From the Freshwater Filametous Cyanobacterium Lyngbya Wollei." Natural Toxins. 5(4). 146-151 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "The Absolute Configuration of Ciguatoxin" J.Am.Chem.Soc.119(46). 11325-11326 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroshi Nagai: "Manauealides, Some of the Causative Agents of a Red Alga Gracilaria Coronopifolia Poisonig in Hawaii." ournal of NATURAL PRODUCTS.60(9). 925-928 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hideyuki Onodera: "Confirmation of Anagoxin-A(S), in the CyanoBacterium Anabaena emmermannii, as the Cause of Bird Kills in Danish Lakes" Toxicon. 35(11). 1645-1648 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "Isolation and Structures of New Ciguatoxin Analogs, 2,3-Dihydroxy CTX3C and 51-Hydroxy CTX3C,Accoumulated in Tropical Reef Fish., Philippe Cruchet and Takeshi Yasumoto" Tetrahedrom Lett.39. 1197-1198 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuya Murata: "Isolation and Structures of New Brevetoxin Analog, Brevetoxin B2, from Greenshell Mussels from New Zealand." Tetrahedron. 54. 735-842 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mari Yotsu-Yamashita: "Synthesis and Confirmation of the Structures of Polonicumtoxins A,B,nd C" Heterocylces. 48. 79-93 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "Bioactive Compounds from Marine Microalgae" Chimia. 52. 63-68 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sasaki: "Identification and Characterization of Pectenotoxin (PTX) 4 and PTX7 as Spiroketal Stereoisomers of Two Previously Reported Pectenotoxins" J.Organic Chemistry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hiroyuki Ogino: "Toxicologic Evaluation of Yessotoxin. Masanori Kumagai, and Takeshi Yasumoto" Natural Toxins. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Katsunori Sasaki: "Application of the Phenylglycine Methyl Ester to the Establishment of the Absolute, Configuration of Dinophysistoxin-1, a Polyether Toxin Responsible for Diarrhetic Shellfish Poisoning" Enantiomer. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoji Igarashi: "Biological activities of prymnesin-2 isolated from a red tide alga Prymnesium Parvum" Natural Toxins. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takeshi Yasumoto: "New Toxins and their Toxicological Evaluations" Proceeding of VIII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Lincoln MacKenzie: "Dinoflagellate Blooms and Associated DSP-toxicity in Shellfish in New Zealand" Proceeding of VIII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Satake: "New Toxic Event Caused by Irish Mussels" Proceeding of VIII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hirofumi Goto: "A Japanese Project for Production and Distribution of Shellfish Toxins as Calibrants for HPLC Analysis" Proceeding of VIII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Anne-Marie Legrand: "Two Structural Types of Ciguatoxins Involved in Ciguatewra Fish Poisoning of French Polynesia" Proceeding of VIII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Aurelia Tubaro: "Occurrence of Yessotoxin-Like Toxins in Phytoplankton and Mussels from Northern Adriatic Sea" Proceeding of VII International Conference on Harmful Algae, 25-29 June, 1997, Vigo-Spein. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Patrizia Ciminiello: "Yessotoxin in mussels of the northern Adriatic Sea" Toxicon. 35(2). 177-183 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Satake: "Isolation and structure of ciguatoxin-4A,a new cituatoxin precursor,from cultures of dinoflagellate Gambierdiscus toxicus and parrotfigh Scarus gibbus." Biosci. Biotech. Biochem.60(12). 2103-2105 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Emiko Ito: "Effects of repeated injection of palytoxin of lymphoid tissues in mice." Toxicon. 35(5). 679-688 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroko Ogura: "Synthetic Study of Ciguatoxin. Absolute Configuration of the C2 Hydroxy Group." Tetrahedron. 53(9). 3057-3072 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Satake: "Two New Analogs of Yessotoxin,Homoyessotoxin and 45-Hydroxyhomoyessotoxin,Isolated from Mussels of the Adriatic Sea." Natural Toxins. 5(3). 107-110 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Fluorometric Measurement of Yessotoxins in Shellfish by High-pressure Liquid Chromatography" Biosci.Biotech.Biochem.61(10). 1775-1777 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kazuya Murata: "Isolaton and Structures of New Ciguatoxin Analogs,Brevetoxin B2,from Greenshell Mussels from New Zealand." Tetrahedron. 54. 735-742 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Mari Yotsu Yamashita: "Synthesis and Confirmation of the Structures of PolonicumtoxinsA,B,and C" Heterocylces.48. 79-93 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tomoji Igarashi: "Biological activities of prymnesin-2 isolated from a red tide alga Prymnesium parvum." Natural Toxins. (印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Katsunori Sasaki: "The Identification and Characterization of Pectenotoxin (PTX) 4 and PTX7 as Spiroketal Stereoisomers of Two Previously Reported Pectenotoxins" J.Organic Chemistry. (印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Bioactive Compounds from Marine Microalgae" Chimia. 52(印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Katsunori Sasaki: "Application of the Phenylglycine Methyl Ester to the Establishment of the Absolute Configuration of Dinophysistoxin-1,a Polyether Toxin Responsible for Diarrhetic Shellfish Poisoning" Enantiomer. 1(印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Katsunori Sasaki: "Identification of the Absolute Configuration of Pectenotoxin-6,a Polyrther Macrolide Compound,by NMR Spectroscopic Method Using a Chiral Anisotropic Reagent,Phenylglycine Methyl Ester." Biosci,Biotech,Biochem.61(10). 1783-1785 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hideyuki Onodera: "New Saxitoxin Analogues From the Freshwater Filametous Cyanobacterium Lyngbya wollei." Natural Toxins. 5(4). 146-151 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Satake: "Identification of Protoceratium reticulatum as the Biogenetic Origin of Yessotoxin." Natural Toxins. 5(4). 164-167 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Satake: "The Absolute Configuration of Ciguatoxin." J.Am.Chem.Soc. 119(46). 11325-11326 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroshi Nagai: "Manauealides,Some of the Causative Agents of a Red Alga Gracilaria coronopifolia Poisoning in Hawaii." jornal of NATURAL PRODUCTS. 60(9). 925-928 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Satake: "Isolaton and Structures of New Ciguatoxin Analogs,2,3-DihydroxyCTX3C and 51-Hydroxy CTX3C,Accoumulated in Tropical Reef Fish." Tetrahedron Letters. 39. 1197-1198 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroyuki Ogino: "Toxicologic Evaluation of Yessotoxin" Natural Toxins. (印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Emiko Ito: "Effects of Repeated Injections of Palytoxin on Lymphold Tissues in Mice" Toxicon. 35. 679-688 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroko Tohda.: "Unstable Expression of the Multi-Drug-Resistant Phennotype in chinese Hamster Ovary Cells Resistant to Okadaic Acid" Biochemical and Biophysical Research Communications. 232. 398-402 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Emiko Ito,: "Morphological observations of diarrhea in mice caused by experimental ciguatoxicosis." Toxicon. 34. 111-122 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Matomo Nishio: "Na^+ permeable channels induced by maltotoxin in guinea-pig single ventricular cells." Euro. J. Pharmacol.297. 293-298 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Nobuaki Matsumori: "Long-range carbon-proton coupling constants for stereochemical assignment of acyclic structures in natural products : configuration of the C5-C9 portion of maitotoxin." Tetrahedron Lett.37. 1269-1272 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] B. Q. Wu.: "11-Oxo-tetrodotoxin and a specifically labelled 3H-tetrodotoxin." Toxicon.34. 407-416 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuaki Akasaka: "Fluorimetric determination of diarrhetic shellfish toxins in scallops and mussels by high-performance liquid chromatography." J. Chromatog.729. 381-386 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Aurella Tubaro: "A protain phosphatase 2A inhibition assay for a fast and sensitive assessment of okadaic acid contamination in mussels." Toxicon.34. 743-752 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hiroshi Nagai: "Aplysiatoxin and debromoaplysiatoxin as the causative agent of a red alga Gracilaria coronopifolia poisoning in Hawaii." Toxicon. 34. 753-761 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Makoto Sasaki: "The complete structure of maitotoxin, I ; Stereochemistry of the C1-C14 side chain." Angew. Chem. Int. Ed. Engl.35. 1672-1675 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Makoto Sasaki: "The complete structure of maitotoxin, II ; Stereochemistry of the C135-C142 side chain and absolute configuration of the entire molecule." Angew. Chem. Int. Ed. Engl.35. 1675-1678 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki Satake: "Relative configuration of yessotoxin and isolation of two new analogs from toxic scallop." Tetrahedron Lett.37. 5955-5958 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Keiichi Konoki: "Blockade of MTX-induced Ca2+ influx in rat glioma C6 cells by alkylamines." J. Natural Toxin. 5 (2). 209-217 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Chemical and etiological studies on tetrodotoxin and its analogs." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 81-90 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Chemistry, etiology and determination methods of ciguatera toxins." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 91-107 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Emiko Ito, Misako: "Intestinal njuries caused by experimental palytoxicosis in mice." Toxicon. 34 (6). 643-652 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Lionel Glendenning.: "Examination of the conformational properties of the prymnesin system : a computational chemistry approach." Bull. Chem. Soc. Jpn.69. 2253-2263 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Tubara: "Suitability of the MTT-Based cytotoxicity assay to detect okadaic acid contamination of mussels." Toxicon.34. 965-974 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuaki Akasaka: "Fluorimetric determination of diarrhetic shellfish toxins in scallops and mussels by high-performance liquid chromatography." Journal of Chromatography A.729. 381-386 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Haruko Takahashi: "Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, Methoxy-(2-naphthyl) acetic acid." Tetrahedron Letters,. 37. 7087-7090 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki Satake: "Isolation and structure of ciguatoin-4A, a new cituatoxin precursor, from cultures of dinoflagellate Gambierdiscus toxicus and parrotfigh Scarus gibbus." Biosci. Biotech. Biochem.60. 2103-2105 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Gary S. Bignami: "Antibodies to maitotoxin elicited by immunization with toxin-fragment conjugates." Toxicon. 34. 1393-1397 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Emiko Ito,: "Intestinal injuries casued by experimental palycoxicosis in mice." Toxicon,. 34. 643-652 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki Satake,: "Chemical studies on the NSP toxins in the greenshell mussels from New Zealand." Harmful and Toxic Algal Blooms. 487-489 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tetsuya seki: "Gymnodimine, a novel toxic imine isolated from the foveaux strait oysters and Gymnodinium sp." Harmful and Toxic Algal Blooms.495-498 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yasumoto T: "Harmful and Tosic Algal Blooms" UNESCO, 586 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Akira Takai: "Inhibition of specific binding of okadaic acid to protein phosphatase 2A by microcystin LRcalyculin-A and tautomycin:method of analysis of interaction of tight-binding ligands with target protein." Biochem.J.306. 657-665 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Dietrich Mebs: "Further report on the occurrence of tetrodotoxin in Atelopus species (Family:Bufonidae)." Toxicon. 33. 246-249 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Tomoji Igarashi: "Chemical studies on prymnesins isolated from Prymnesium parvum" Harmful Marine Algal Blooms. 303-308 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Maitotoxin and other ciguatera toxins:from structures to determination" Harmful Marine Algal Blooms. 377-381 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Ron L.Manger: "Detection of sodium channel toxins:directed cytotoxicity assays of purified ciguatoxins,brevetoxins,saxitoxins,and seafood extracts." J.A.O.A.C.Intern.78. 521-527 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Takeshi Yasumoto: "Determination of marine toxins in foods" J.A.O.A.C.Intern.78. 574-582 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masaya Usami: "Palytoxin analogs from the dinoflagellate Ostreopsis siamensis" J.Am.Chem.Soc.117. 5389-5390 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masayuki Satake: "Structural confrimation of maitotoxin based on complete 13C NMR assignments and the three-dimensional PFG NOESY-HMQC spectrum" J.Am.Chem.Soc.117. 7019-7020 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Hitoshi Ishida: "Brevetoxin BI,A new polyether marine toxin from the New Zealand Shellfish,Austrovenus stutchburyi." Tetrahedron Lett.36. 725-728 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mari Yotsu-Yamashita: "Four new analogs of polycavernoside A." Tetrahedron Lett.36. 5563-5566 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Tetsuya Seki: "Gymnodimine a new marine toxin of unprecedented structure isolated from New Zeland Oysters and the Dinoflagellate,Gymnodinium sp." Tetrahedron Lett.36. 7093-7096 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akio Morohashi: "Brevetoxin B3,a new brevetoxin analog isolated from the greenshell mussel Perna canaliculus involved in neurotoxic shellfish poisoning in New Zealand." Tetrahedron Lett.36. 8995-8998 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mari Yotsu-Yamasita: "5,6,11-Trideoxytetrodotoxin from the puffer fish,fugu poecilonotus" Tetrahedron Lett.36. 9329-9332 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Sasaki: "Stereochemical assignment of the C35-C39 acyclie linkage in maitotoxin:completion of stereochemical determination of C15-C134" Tetrahedron Lett.36. 9011-9014 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Patrizia Ciminiello: "Determination of PSP toxins in mussels from the Adriatic sea" Marine Pollution Bulletin. 30. 733-735 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Tomoji Igarashi: "Prymnesin-2:A potent ichthyotoxic snd hemolytic glycoside isolated from the red tide alga Prymnesium parvum." J.Am.Chem.Soc. 118. 476-480 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] 村田道雄: "分子量3422の海洋猛毒・マイトトキシンの構造" 有機合成化学協会誌. 53. 207-217 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 佐々木誠: "マイトトキシン完全構造決定への合成科学的アプローチ" 第37回天然有機化合物討論会講演要旨集. 121-126 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 佐竹真幸: "ニュージランド産二枚貝中の新規神経性貝毒と新規有毒成分Gymnodimineの構造研究" 第37回天然有機化合物討論会講演要旨集. 684-689 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 直木秀夫: "タンデムマススペクトルのよる構造解析-海洋ポリエーテル化合物への応用" 第37回天然有機化合物討論会講演要旨集. 212-217 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2018-03-28  

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