1991 Fiscal Year Annual Research Report

生体機構制御物質の有機化学

Research Project

Project/Area Number	03303003
Research Institution	Hokkaido University
Principal Investigator	白濱晴久北海道大学, 理学部, 教授 (00000802)
Co-Investigator(Kenkyū-buntansha)	楠本正一大阪大学, 理学部, 教授 (30028253) 磯部稔名古屋大学, 農学部, 助教授 (00023466) 山村庄亮慶応大学, 理工学部, 教授 (40076708) 橘和夫東京大学, 理学部, 教授 (70142081) 平間正博東北大学, 反応化学研究所, 教授 (30165203)
Keywords	神経毒 / 神経毒の合成 / 神経突起伸展作用物質 / 細胞生長制御物質 / 発癌プロモ-タ- / 発癌性物質 / 摂食阻害物質 / 他感作用物質
Research Abstract	1.神経毒の構造決定、合成と伝達機構:興奮性グルタメ-ト受容体の構造、作用点、作用様式を探るためピロリジンー2.3ージカルボン酸の立体異性体4個を合成して作用を調べた。シガトキシンの絶対配置を5Rと推定した。蜂毒の原因物質と推定した2個を合成し活性を調べた。パリトキシンはカチオンチャンネル形成とNaポンプの阻害をすることがわかった。テトロドトキシン合成のための基礎研究を行った。神経突起伸展作用物質をヒオオギ,ヤエヤマシギ等から見出し構造を決定した。 2.細胞生長制御機構:ロ-レンシン,ダクチリンを光学活性体の形で全合成した。ゼストキノンの仮想的な生合成前駄体の不斉合成を行い絶対配置を決定した。ノピノンよりバ-ノレピンの全合成の重要中間体を合成した。罹病トマトの粗酵素液がαーリノレイン酸を酸化して抗植物病菌性を9S‐OOHとすることを見出した。バンコマイシンの活性部位に相当する化合物を合成し、これが強い活性を示すことを見出した。プテロキシドを単純化した化合物を合成し、これがDNAのG,A特定位置をアルキル化することを見出した。サルノコシカケ科のキノコから発癌プロモ-タ-作用のあるトリテルペン数個を単離し構造決定した。シソから抗菌作用をもつ新規物質3種を単離し構造決定した。 3.摂食阻害、他感作用等の機作:褐藻からチロシナ-ゼ阻害活性物質を単離し構造を決定した。ヌノサラシ科の魚が分泌する魚毒成分を18員環ポリアミンラクタムと推定した。リポ多糖に含まれる特異な8炭糖のリン酸エステルを合成した。クレロダンジテルペンの重要な合成中間体を合成した。10π電子系芳香属イリドイドを合成した。レスタの成長制御及び生長促進活性を示す物質をウラジロから単離し構造決定した。6種の海産動物からホヤ受精卵卵割阻害物質を単離し構造を決めた。マサキからアガロフラン誘導体3種を得構造を決めた。

Research Products

(32 results)

All Other

All Publications (32 results)

[Publications] K.Konno: "Synthesis and Neuroexcitatoty Activity of Some Acromelic Acid Analogs" Heterocycles. 33. 303-311 (1992)
[Publications] K.Hashimoto: "Synthesis of New Acromelic Acid Congeners:Novel Neuroexcitatory Amino Acids Acting on Glutamate Receptor" Tetrahedron Lett.32. 2625-2628 (1991)
[Publications] Lian‐xun GAO: "Highly Regioselective Ring Opening of 2,3‐Epoxy Alcohol Methanesulfonates" Chemistry Lett.1787-1790 (1991)
[Publications] Hisahiro Hagiwara: "Total Synthesis and Adsolute Stereostructure of (+)‐Dysideapalaunic Acid" J.Chem.Soc.,Perkin Trans.1. 1803-1807 (1991)
[Publications] M.Hirama: "Simple Strategy for the Synthesis of the Avermectin‐Melbemycin Family.Total Synthesis of Milbemycin α1." J.Am.Chem.Soc.113. 1830-1832 (1991)
[Publications] T.Suzuki: "Enantioselective Synthesis of AB Ring Fragment of Gambiertoxin 4B.Implication the for Absolute Configuration of Gambiertoxin 4B and Ciguatoxin." Tetrahedron Lett.32. 4505-4508 (1991)
[Publications] M.Hirama: "Synthesis and DNA Cleaving Abilities of Functional Neocarzinostatin Chromophore Analogues.Base Discrimination by a Simple Alcohol." J.Am.Chem.Soc.113. 9851-9853 (1991)
[Publications] M.O.Ishitsuka: "Isolation of a Monomeric Counterpart of the Marine Biscembranoids,a Biogenetic Diels‐Alber Precursor" Tetrahedron Lett.32. 2917-2918 (1991)
[Publications] K.Iguchi: "Stereostructures of Unique 13‐Membered Carbocyclic Cembranolides from the Soft Coral Lobophytum pauciflorum" Chem.Lett.319-322 (1991)
[Publications] 生井恒雄: "Cytotoxixity and Anti‐blast Activity of Hydroperoxide of Linolenic Acid Produced by in Vitro Enzyme Reaction Using Blast‐infected Rice Leaves" Ann.Phytopath.57. 339-344 (1991)
[Publications] Makoto Sasaki: "An Efficient and Stereocontrolled Synthesis of the Nephritogenoside Core Structure" Tetrahedron Letters. 32. 6873-6876 (1991)
[Publications] S.Kosemura: "The Structures of Citreohybridone A and B,Novel Sesterterperpenoid‐type Metabolites of a Hybrid Strain KO 0031 Derived from Penicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 3543-3546 (1991)
[Publications] K.Matsunaga: "Isolation and Structure of Citreoindole,a New Metabolite of Hybrid Strain KO 0052 Derived from Prnicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 6883-6884 (1991)
[Publications] A.Carl: "Reguration of Ca‐Activated K^+ Channels by Protein Kinase A and Phosphatase Inhibitors" Am.J.Physiol.261. C387-C392 (1991)
[Publications] A.Herunsalee: "Diastereoselective Heteroconjugate Addition of Acetylenec Derivative" Tetrahedron. 47. 3727-3736 (1991)
[Publications] T.Nishikawa: "Synthetic Studies on the Bicyclo[7.3.1]‐tridecendiyne System in an Antitumor Antibiotic,Dynemicia A" Synlett. 393-394 (1991)
[Publications] K.Fukase: "Application of 4‐Azidobenzyl Grorp to Protection of Hydroxyl Functions" Tetrahedron Lett.32. 3557-3558 (1991)
[Publications] C.T.Tokuyama: "Applanoxidic Acids A,B,C and D,Biologically Active Tetracyclic Triterpenes from Ganoderma applanatum" Phytochemistry. 30. 4105-4109 (1991)
[Publications] Yuting Ge: "An Efficient Synthesis of Cerbinal,a 10π Aromatic Iridoid" Chemistry Letters. 139-140 (1992)
[Publications] H.L.Siddiqui: "Biologically Active Novel Clerodane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Chem.Lett.701-704 (1991)
[Publications] K.Munesada: "Biologically Activa Labdane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Phytochemistry. 31. (1992)
[Publications] M.Ochi: "Litophynins I and J,Two New Biologically Active Ditepernoids from the Soft Coral Litophyton sp." Chem.Lett.155-158 (1992)
[Publications] Y.Fukuyama: "Prenylaed Xanthones from Garcinia subelliptica" Phytochem.30. 3433-3436 (1991)
[Publications] Y.Fukuyama: "Neurotrophic Sesquiterpene‐neolignans from Magnolia obovata:Structure and Neurotrophic Activity" Tetrahedron. 48. 377-392 (1992)
[Publications] H.Hashimoto: "Trends in Oraganic Chemistry Vo1.2" Research Trends, 32 (1991)
[Publications] 橋本貴美子: "キノコの化学・生化学" 学会出版センタ-, 17 (1992)
[Publications] 平間正博: "ネオカルジノスタチン様人工分子の設計と合成" 有機合成化学協会誌, 11 (1991)
[Publications] 橘和夫: "化学と生物" 学会出版センタ-, 3 (1991)
[Publications] Yoko Naya: "Marine Biotechnology Vo1.1" Plenum Publishing Corp., (1992)
[Publications] S.Yamamura: "Studies in Natural Products Chemistry" Elsevier Science Publishers, (1992)
[Publications] D.Uemura: "Marine Bioorganic Chemistry Vo1.4" Springer‐Verlag, 31 (1991)
[Publications] 磯部稔: "海洋資源と医薬品I 続一医薬品の開発" 廣川書店, 9 (1991)

1991 Fiscal Year Annual Research Report

生体機構制御物質の有機化学

Principal Investigator

白濱 晴久 北海道大学, 理学部, 教授 (00000802)

Research Products

[Publications] K.Konno: "Synthesis and Neuroexcitatoty Activity of Some Acromelic Acid Analogs" Heterocycles. 33. 303-311 (1992)

[Publications] K.Hashimoto: "Synthesis of New Acromelic Acid Congeners:Novel Neuroexcitatory Amino Acids Acting on Glutamate Receptor" Tetrahedron Lett.32. 2625-2628 (1991)

[Publications] Lian‐xun GAO: "Highly Regioselective Ring Opening of 2,3‐Epoxy Alcohol Methanesulfonates" Chemistry Lett.1787-1790 (1991)

[Publications] Hisahiro Hagiwara: "Total Synthesis and Adsolute Stereostructure of (+)‐Dysideapalaunic Acid" J.Chem.Soc.,Perkin Trans.1. 1803-1807 (1991)

[Publications] M.Hirama: "Simple Strategy for the Synthesis of the Avermectin‐Melbemycin Family.Total Synthesis of Milbemycin α1." J.Am.Chem.Soc.113. 1830-1832 (1991)

[Publications] T.Suzuki: "Enantioselective Synthesis of AB Ring Fragment of Gambiertoxin 4B.Implication the for Absolute Configuration of Gambiertoxin 4B and Ciguatoxin." Tetrahedron Lett.32. 4505-4508 (1991)

[Publications] M.Hirama: "Synthesis and DNA Cleaving Abilities of Functional Neocarzinostatin Chromophore Analogues.Base Discrimination by a Simple Alcohol." J.Am.Chem.Soc.113. 9851-9853 (1991)

[Publications] M.O.Ishitsuka: "Isolation of a Monomeric Counterpart of the Marine Biscembranoids,a Biogenetic Diels‐Alber Precursor" Tetrahedron Lett.32. 2917-2918 (1991)

[Publications] K.Iguchi: "Stereostructures of Unique 13‐Membered Carbocyclic Cembranolides from the Soft Coral Lobophytum pauciflorum" Chem.Lett.319-322 (1991)

[Publications] 生井 恒雄: "Cytotoxixity and Anti‐blast Activity of Hydroperoxide of Linolenic Acid Produced by in Vitro Enzyme Reaction Using Blast‐infected Rice Leaves" Ann.Phytopath.57. 339-344 (1991)

[Publications] Makoto Sasaki: "An Efficient and Stereocontrolled Synthesis of the Nephritogenoside Core Structure" Tetrahedron Letters. 32. 6873-6876 (1991)

[Publications] S.Kosemura: "The Structures of Citreohybridone A and B,Novel Sesterterperpenoid‐type Metabolites of a Hybrid Strain KO 0031 Derived from Penicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 3543-3546 (1991)

[Publications] K.Matsunaga: "Isolation and Structure of Citreoindole,a New Metabolite of Hybrid Strain KO 0052 Derived from Prnicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 6883-6884 (1991)

[Publications] A.Carl: "Reguration of Ca‐Activated K^+ Channels by Protein Kinase A and Phosphatase Inhibitors" Am.J.Physiol.261. C387-C392 (1991)

[Publications] A.Herunsalee: "Diastereoselective Heteroconjugate Addition of Acetylenec Derivative" Tetrahedron. 47. 3727-3736 (1991)

[Publications] T.Nishikawa: "Synthetic Studies on the Bicyclo[7.3.1]‐tridecendiyne System in an Antitumor Antibiotic,Dynemicia A" Synlett. 393-394 (1991)

[Publications] K.Fukase: "Application of 4‐Azidobenzyl Grorp to Protection of Hydroxyl Functions" Tetrahedron Lett.32. 3557-3558 (1991)

[Publications] C.T.Tokuyama: "Applanoxidic Acids A,B,C and D,Biologically Active Tetracyclic Triterpenes from Ganoderma applanatum" Phytochemistry. 30. 4105-4109 (1991)

[Publications] Yuting Ge: "An Efficient Synthesis of Cerbinal,a 10π Aromatic Iridoid" Chemistry Letters. 139-140 (1992)

[Publications] H.L.Siddiqui: "Biologically Active Novel Clerodane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Chem.Lett.701-704 (1991)

[Publications] K.Munesada: "Biologically Activa Labdane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Phytochemistry. 31. (1992)

[Publications] M.Ochi: "Litophynins I and J,Two New Biologically Active Ditepernoids from the Soft Coral Litophyton sp." Chem.Lett.155-158 (1992)

[Publications] Y.Fukuyama: "Prenylaed Xanthones from Garcinia subelliptica" Phytochem.30. 3433-3436 (1991)

[Publications] Y.Fukuyama: "Neurotrophic Sesquiterpene‐neolignans from Magnolia obovata:Structure and Neurotrophic Activity" Tetrahedron. 48. 377-392 (1992)

[Publications] H.Hashimoto: "Trends in Oraganic Chemistry Vo1.2" Research Trends, 32 (1991)

[Publications] 橋本 貴美子: "キノコの化学・生化学" 学会出版センタ-, 17 (1992)

[Publications] 平間 正博: "ネオカルジノスタチン様人工分子の設計と合成" 有機合成化学協会誌, 11 (1991)

[Publications] 橘 和夫: "化学と生物" 学会出版センタ-, 3 (1991)

[Publications] Yoko Naya: "Marine Biotechnology Vo1.1" Plenum Publishing Corp., (1992)

[Publications] S.Yamamura: "Studies in Natural Products Chemistry" Elsevier Science Publishers, (1992)

[Publications] D.Uemura: "Marine Bioorganic Chemistry Vo1.4" Springer‐Verlag, 31 (1991)

[Publications] 磯部 稔: "海洋資源と医薬品I 続一医薬品の開発" 廣川書店, 9 (1991)

白濱晴久北海道大学, 理学部, 教授 (00000802)

[Publications] 生井恒雄: "Cytotoxixity and Anti‐blast Activity of Hydroperoxide of Linolenic Acid Produced by in Vitro Enzyme Reaction Using Blast‐infected Rice Leaves" Ann.Phytopath.57. 339-344 (1991)

[Publications] 橋本貴美子: "キノコの化学・生化学" 学会出版センタ-, 17 (1992)

[Publications] 平間正博: "ネオカルジノスタチン様人工分子の設計と合成" 有機合成化学協会誌, 11 (1991)

[Publications] 橘和夫: "化学と生物" 学会出版センタ-, 3 (1991)

[Publications] 磯部稔: "海洋資源と医薬品I 続一医薬品の開発" 廣川書店, 9 (1991)