1996 Fiscal Year Annual Research Report

超活性海洋天然物の精密構造解析

Research Project

Project/Area Number	07102002
Research Institution	Tohoku University
Principal Investigator	安元健東北大学, 農学部, 教授 (20011885)
Co-Investigator(Kenkyū-buntansha)	山下まり東北大学, 農学部, 教務職員 (50192430)
Keywords	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
Research Abstract	[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。

Research Products

(24 results)

All Other

All Publications (24 results)

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

1996 Fiscal Year Annual Research Report

超活性海洋天然物の精密構造解析

Principal Investigator

安元 健 東北大学, 農学部, 教授 (20011885)

Research Products

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

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

[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)

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

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

[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)

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

[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)

[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)

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

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

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

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

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

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

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

[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)

[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)

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

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

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

[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)

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

安元健東北大学, 農学部, 教授 (20011885)