1996 年度実績報告書

超活性海洋天然物の精密構造解析

研究課題

研究課題/領域番号	07102002
研究機関	東北大学
研究代表者	安元健東北大学, 農学部, 教授 (20011885)
研究分担者	山下まり東北大学, 農学部, 教務職員 (50192430)
キーワード	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
研究概要	[構造解析]シガテラと呼ばれる魚類中毒の原因毒であるシガトキシン、シガトキシン4A、マイトトキシン、2枚貝の毒イェッソトキシン、ブレベトキシンB2の絶対構造を決定した。また、代表的な赤潮の毒プリムネシン-2の平面構造を決定し、環状構造部分については相対立体配置を明らかにした。さらに、計算化学により溶液中の立体構造を推定した。また、シガトキシン及びイェッソトキシンの新規誘導体を単離し、構造を決定した。 [作用解明]フグのテトロドトキシン(TTX)耐性機構を解明するために、ヒガンフグ筋肉のNaチャネルのcDNAの解析を行い、TTX耐性と考えられるcDNA (type2)を、魚類NaチャネルのcDNAコード領域全長としては初めてクローニングした。Type2-cDNAは全長6700bp、1880aaからなり、TTX感受性を左右する382番目のアミノ酸が感受性型の(F/Y)ではなく、Nをコードしていることを明らかになった。また、今後の作用解析に有用な放射性標識化合物として[^3H]11-ノル-TTX-6-オールを調製した。 [定量法]下痢性貝毒の簡便な検出・定量法として、オカダ酸類については酵素阻害定量法を、イェッソトキシン類については蛍光-高速液体クロマトグラフィー法を開発した。 [毒の起源解明]ニシン・イワシ類による高死亡率食中毒として知られていたクルペオトキシズムの原因毒が、パリトキシンまたはその同族体であることを明らかにした。毒の起源を底性渦鞭藻のOstreopsis siamensisと推定し、培養藻体からパリトキシン類縁体5成分を単離した。また、アドリア海産渦鞭毛藻Gonyaulax polyedraからホモイェッソトキシンを検出し、同海域の2枚貝毒化の原因と同定した。

研究成果

(24件)

すべてその他

すべて文献書誌 (24件)

[文献書誌] Emiko Ito,: "Morphological observations of diarrhea in mice caused by experimental ciguatoxicosis." Toxicon. 34. 111-122 (1996)
[文献書誌] Matomo Nishio: "Na^+ permeable channels induced by maltotoxin in guinea-pig single ventricular cells." Euro. J. Pharmacol.297. 293-298 (1996)
[文献書誌] 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)
[文献書誌] B. Q. Wu.: "11-Oxo-tetrodotoxin and a specifically labelled 3H-tetrodotoxin." Toxicon.34. 407-416 (1996)
[文献書誌] Kazuaki Akasaka: "Fluorimetric determination of diarrhetic shellfish toxins in scallops and mussels by high-performance liquid chromatography." J. Chromatog.729. 381-386 (1996)
[文献書誌] 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)
[文献書誌] Hiroshi Nagai: "Aplysiatoxin and debromoaplysiatoxin as the causative agent of a red alga Gracilaria coronopifolia poisoning in Hawaii." Toxicon. 34. 753-761 (1996)
[文献書誌] Makoto Sasaki: "The complete structure of maitotoxin, I ; Stereochemistry of the C1-C14 side chain." Angew. Chem. Int. Ed. Engl.35. 1672-1675 (1996)
[文献書誌] 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)
[文献書誌] Masayuki Satake: "Relative configuration of yessotoxin and isolation of two new analogs from toxic scallop." Tetrahedron Lett.37. 5955-5958 (1996)
[文献書誌] Keiichi Konoki: "Blockade of MTX-induced Ca2+ influx in rat glioma C6 cells by alkylamines." J. Natural Toxin. 5 (2). 209-217 (1996)
[文献書誌] Takeshi Yasumoto: "Chemical and etiological studies on tetrodotoxin and its analogs." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 81-90 (1996)
[文献書誌] Takeshi Yasumoto: "Chemistry, etiology and determination methods of ciguatera toxins." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 91-107 (1996)
[文献書誌] Emiko Ito, Misako: "Intestinal njuries caused by experimental palytoxicosis in mice." Toxicon. 34 (6). 643-652 (1996)
[文献書誌] Lionel Glendenning.: "Examination of the conformational properties of the prymnesin system : a computational chemistry approach." Bull. Chem. Soc. Jpn.69. 2253-2263 (1996)
[文献書誌] A. Tubara: "Suitability of the MTT-Based cytotoxicity assay to detect okadaic acid contamination of mussels." Toxicon.34. 965-974 (1996)
[文献書誌] 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)
[文献書誌] 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)
[文献書誌] 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)
[文献書誌] Gary S. Bignami: "Antibodies to maitotoxin elicited by immunization with toxin-fragment conjugates." Toxicon. 34. 1393-1397 (1996)
[文献書誌] Emiko Ito,: "Intestinal injuries casued by experimental palycoxicosis in mice." Toxicon,. 34. 643-652 (1996)
[文献書誌] Masayuki Satake,: "Chemical studies on the NSP toxins in the greenshell mussels from New Zealand." Harmful and Toxic Algal Blooms. 487-489 (1996)
[文献書誌] Tetsuya seki: "Gymnodimine, a novel toxic imine isolated from the foveaux strait oysters and Gymnodinium sp." Harmful and Toxic Algal Blooms.495-498 (1996)
[文献書誌] Yasumoto T: "Harmful and Tosic Algal Blooms" UNESCO, 586 (1996)

1996 年度 実績報告書

超活性海洋天然物の精密構造解析

研究代表者

安元 健 東北大学, 農学部, 教授 (20011885)

研究成果

[文献書誌] Emiko Ito,: "Morphological observations of diarrhea in mice caused by experimental ciguatoxicosis." Toxicon. 34. 111-122 (1996)

[文献書誌] Matomo Nishio: "Na^+ permeable channels induced by maltotoxin in guinea-pig single ventricular cells." Euro. J. Pharmacol.297. 293-298 (1996)

[文献書誌] 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)

[文献書誌] B. Q. Wu.: "11-Oxo-tetrodotoxin and a specifically labelled 3H-tetrodotoxin." Toxicon.34. 407-416 (1996)

[文献書誌] Kazuaki Akasaka: "Fluorimetric determination of diarrhetic shellfish toxins in scallops and mussels by high-performance liquid chromatography." J. Chromatog.729. 381-386 (1996)

[文献書誌] 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)

[文献書誌] Hiroshi Nagai: "Aplysiatoxin and debromoaplysiatoxin as the causative agent of a red alga Gracilaria coronopifolia poisoning in Hawaii." Toxicon. 34. 753-761 (1996)

[文献書誌] Makoto Sasaki: "The complete structure of maitotoxin, I ; Stereochemistry of the C1-C14 side chain." Angew. Chem. Int. Ed. Engl.35. 1672-1675 (1996)

[文献書誌] 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)

[文献書誌] Masayuki Satake: "Relative configuration of yessotoxin and isolation of two new analogs from toxic scallop." Tetrahedron Lett.37. 5955-5958 (1996)

[文献書誌] Keiichi Konoki: "Blockade of MTX-induced Ca2+ influx in rat glioma C6 cells by alkylamines." J. Natural Toxin. 5 (2). 209-217 (1996)

[文献書誌] Takeshi Yasumoto: "Chemical and etiological studies on tetrodotoxin and its analogs." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 81-90 (1996)

[文献書誌] Takeshi Yasumoto: "Chemistry, etiology and determination methods of ciguatera toxins." J. TOXICOL.-TOXIN REVIEWS. 15 (2). 91-107 (1996)

[文献書誌] Emiko Ito, Misako: "Intestinal njuries caused by experimental palytoxicosis in mice." Toxicon. 34 (6). 643-652 (1996)

[文献書誌] Lionel Glendenning.: "Examination of the conformational properties of the prymnesin system : a computational chemistry approach." Bull. Chem. Soc. Jpn.69. 2253-2263 (1996)

[文献書誌] A. Tubara: "Suitability of the MTT-Based cytotoxicity assay to detect okadaic acid contamination of mussels." Toxicon.34. 965-974 (1996)

[文献書誌] 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)

[文献書誌] 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)

[文献書誌] Gary S. Bignami: "Antibodies to maitotoxin elicited by immunization with toxin-fragment conjugates." Toxicon. 34. 1393-1397 (1996)

[文献書誌] Emiko Ito,: "Intestinal injuries casued by experimental palycoxicosis in mice." Toxicon,. 34. 643-652 (1996)

[文献書誌] Masayuki Satake,: "Chemical studies on the NSP toxins in the greenshell mussels from New Zealand." Harmful and Toxic Algal Blooms. 487-489 (1996)

[文献書誌] Tetsuya seki: "Gymnodimine, a novel toxic imine isolated from the foveaux strait oysters and Gymnodinium sp." Harmful and Toxic Algal Blooms.495-498 (1996)

[文献書誌] Yasumoto T: "Harmful and Tosic Algal Blooms" UNESCO, 586 (1996)

1996 年度実績報告書

安元健東北大学, 農学部, 教授 (20011885)