生体機構制御物質の有機化学

1992 Fiscal Year Annual Research Report

• Project/Area Number: 03303003
• Research Institution: HOKKAIDO UNIVERSITY,(FACULTY OF SCIENCE)
• 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, 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, 理学部, 教授 (30165203)
• Keywords: 神経毒 / 神経毒の単離 / 神経突起伸展作用物質 / 細胞生長制御物質 / 発癌プロモーター / 卵割阻害活性物質 / 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:オオワライタケの神経毒ジムノピリンのHMG酸部分の絶対配置をSと決定した(白濱)。協力海産毒シガノトキシンの絶対配置を決定するためのモデルを合成した(平間)。孤立性狩人蜂の蜂毒を分離し、強力な活性を示す画分よりプロリンを構成単位として含むペプチド数種を単離した(奥村)。オカダ酸の立体配置をDistance Geometry法で検討した(上村)。テトロドトキシン合成中間体を新方法で合成した(磯部)。脳神経でコリンアセチル転位酸素活性を上げる新物質イリシノンを単離した(児玉)。
2.細胞生長制御機構:海産含ハロゲン中員環エーテル、ローランとオブツセニンの合成研究を行った(村井)。リ病トマトのリポキシゲナーゼはα-リノレイン酸を選択的に酸化し、抗菌活性を示す9-OOHを与えた(加藤忠)。2種の菌株より作ったハイブリッド菌株より新シトレオハイブリドンを単離構造決定した(山村)。アメフラシより細胞毒アプリロニンAを単離し、新規24員環マクロリドと決定した(山田)。発癌プロモーター抑制活性のアプラノキジン酸E〜Hをサルノコシカケより得、構造を決定した(林)。サンゴより細胞毒性テルペンを単離し、構造を決定した(楠見)。抗腫瘍性のウドテアトリアール水和物対象体を合成した(磯江)。サルノコシカケ樹皮より細胞毒性のクマリン誘導体を得た(森)。
3.摂食阻害、他感作用、免疫増強:キハツソクの防御物質、18員環ポリアミンラクタムの構造中の末決定部分を確定した(橘)。グラム陽性菌表層成分で、免疫増強作用のあるリポタイコ酸の推定構造を合成した(楠本)。クレロダンジテルペン骨格の立体選択的合成法の確立(野老山)。ノピノを不斉源として。ジュハビオン、セコプソイドペテロシンAの合成を試みた(加藤紀)。強心活性体ハレナキノールの生合成前駆体を海綿より単離した(宇田)。ヘビノネコザの根から2種の他感作用物質を単離した(菅)。シソ葉からレンズアルドース還元酵素阻害活性を示すものを見出した(中山)。ホヤ受精卵に対し卵割阻害活性を示す5種のジテルペンを単離し、構造を決定した(越智)。

Research Products

• [Publications] M.Horikawa: "Efficient Syntheses of Acromelic Acids B and E Which are Potent Neuroexcitatory Amino Acids" Tetrahedron Lett. 34. 331-334 (1993)
• [Publications] M.Tanaka: "Chirality of the Acyl Group of Gymnopilin" Phytochemistry. 31. 4355-4356 (1992)
• [Publications] H.Hagiwara: "Total Synthesis and Absolute Stereostructure of(+)-Dysideapalaunic Acid" J.Chem.Soc,Perkin Trans,1. 1. 1803-1807 (1991)
• [Publications] M.Yamaguchi: "Direct Formation of Reactive Alkyltrichlorotins from 1-Alkynes,Sncl^4,and Bu^3N.A Mild Alkynylation Reagent of Aldehydes,Acetals,and Enones." Chem.Lett.2479-2482 (1992)
• [Publications] M.Yamaguchi: "Desilylation Reactions of Poly[(t-butyldimethylsilyloxy)phenylacetylene]s" Chem.Lett.2261-2262 (1992)
• [Publications] M.Kato: "Efficient Preparation of a Key Inteumediate Suitable for the Asymmetric Synthesis of(+)-Vernolepin and(-)-Vernomenin" J.Chem.Soc.Chem.Commun.697-698 (1992)
• [Publications] M.kato: "A Stereocontrollde Synthesis of(4aS,8aR)-(+)-7,7-Ethylenedioxy-4,4,8a-trimethyloctahydro-2(1H)-naphtalenone" Bull.Chen.Soc.Jpn.65. 2071-2075 (1992)
• [Publications] I.Ohtani: "An Insight into the Conformation of Ptilomycalin A.The NMR Properties of Trifluoroacetylated Spermidine Analogues" Tetrahedron Lett.33. 2525-2528 (1992)
• [Publications] I.Ohtani: "Structure and Chemical Properties of Ptilomycalin A" J.Am.Chem.Soc.114. 8472-8479 (1992)
• [Publications] T.Kato: "Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by Its In Vitro Enzyme Reaction." Biosci.Biotech.Biochem.56. 373-375 (1992)
• [Publications] T.Kato: "Selective Terminal Olefin Oxidation of n-3 Polyunsaturated Fatty Acids" Tetrahedron Lett.33. 1475-1478 (1992)
• [Publications] M.Kubota: "Structure of Citreohybridone A" Acta Cryst.C48. 552 (1992)
• [Publications] S.kosemura: "Citreobenzofurans A,B,and C,First Isolation of SESquiterpene-type Metaboletes of a Hybrid Strain KO0031Derived from Penicillium Citreo-viride B.IFO4692and6200" Bull.Chem.Soc.Jpn.65. 926 (1992)
• [Publications] M.Suganuma: "Biochemical Effects and Tumor Promotion of Kkadaic Acid in Glandular Stomach of SD Rats" Carcinogenesis. 13. 1841-1845 (1992)
• [Publications] S.Ikegami: "Effect of Okadaic Acid on Embryonic Development of the Starfish Asterina pectinifera" Biosci.Biotech.Biochem.56. 1007-1011 (1992)
• [Publications] H.Kigoshi: "Synthesis of Analogues of a Bracken Ultimate Carcinogen and Their DNA Cleaving Activities" Tetrahedron Lett.44. 6647-6650 (1992)
• [Publications] C.T.Barrow: "Struchure and activity Studies of Pardaxin and Analogues Using Model membranes of Phosphatidyl Choline" Biochem.Biophys.Acta. 112. 235-240 (1992)
• [Publications] A.Takai: "Inhibitory Effect of Okadaic Acid-Derivatives on Protein Phosphatases:A Study on Structure-Affinity Relationship" Biochem.J.284. 539-544 (1992)
• [Publications] T.Tsukiyama: "C-Glycosidation with Silylacetylenes to D-Glucals" Tetrahedron Lett.33. 7911-7914 (1992)
• [Publications] Y.Hayashi: "Nagilactones as an Anti-feedant of Podocarpus nagi for Herbivorous Mammals" Biosci.Biotech.Biochem.56. 1302-1303 (1992)
• [Publications] C.S.M.Chairul: "Applanoxidic Acids E,F,G and H,Biologically Active Lanostanoid Triterpenes from Ganoderma applanatum as an Inhibitor against Tumor Promoter" Phytochemistry. (1993)
• [Publications] S.Katsumura: "Phospholipase A^2 Inhibition by Manoalide:Development of Simple analogues and Necessary Functional for Inhibition" BioMed.Chem.Lett.2. 1263-1266 (1992)
• [Publications] S.Katsumura: "Toward Elucidation of the Inhibition of Phospholipase A^2 by Manoalide Analogues" BioMed.Chem.Lett.2. 1267-1268 (1993)
• [Publications] T.Fujita: "Perillpside A.a Monoterpene Glucoside from Perilla Frutescens" Phytochemistry. 31. 3265-3267 (1992)
• [Publications] H.L.Siddiqui: "Biologically Active Clerodane-type Diterpene Alcohol and Its Glycosides from the Root-stalks of Ferns" J.Chem.Soc.,Oerkin trans1. 781-785 (1992)
• [Publications] T.Endo: "Demonstration of Geranyl Diphoshate Synthase in Several Higher Plans" Phytochemistry. 31. 2273-2275 (1992)
• [Publications] M.Ochi: "Litophynins I and J.Two New Biologically Active Diterpenoids from the Soft Coral Litophyton sp." Chem.Lett.155-158 (1992)
• [Publications] M.Ochi: "Calicogorains A.B.and C.Three Bioactive Sphinganine Derivatives from the Gorgonian Cal icogorgia sp." Tetrahedron Lett.33. 7531-7534 (1993)
• [Publications] Y.Fukuyama: "Prenylated C6-C3 compounds from Illicium tashiroi" Phytochimistry. 31. 3975-3979 (1992)
• [Publications] Y.fukuyama: "Illicinolides A and B,Novel Sesquiterpenes form the Wood of Illicium tsahiroi" Tetrahedron. 48. 5847-5854 (1992)
• [Publications] K.Ueda: "Two Sesquiterpene Polyesters from the Ripe Fruits of Eunymus japonicus Thunb" Bull.Coll.Sci.,Univ.of Ryukyus. 54. 41-46 (1992)
• [Publications] K.Ueda: "A Sesquiterpene Oolyester from Euonymus tanakae" Phytochem.(1993)
• [Publications] F.Fukase: "Synthesis of New Serine-linked Oligosaccharides in Blood-Clotting Factor vll and ix and Protain Z" Bull.Chem.Soc,Jpn.65. 436-445 (1992)
• [Publications] F.Fukase: "Iodosobenzene-Triflic Anhydrides as an Efficient Promoter for Glysosidation Reaction Using Thisglycosides as Donons" Tetrahedron Lett.33. 7165-7168 (1992)
• [Publications] K.Tsushima: "Total Synthesis of(+)-laurencin" Tetrahedron Lett.33. 4345-4348 (1992)
• [Publications] L.Gao: "Total Synthesie of(-)-Dactylyne and(-)-Isodactylyne" Tetrahidron Lett.33. 4349-4352 (1992)
• [Publications] 白浜 晴久: "生物毒の世界" 大日本図書(株), 24 (1992)
• [Publications] H.Shirahama: "Organic Synthesis in Japan:Past,Present,and Future" Tokyo Kagaku Dozin, 12 (1992)
• [Publications] 白濱 晴久: "キノコの化学、生化学" 学会出版センター, 17 (1992)
• [Publications] 平間 正博: "有機合成の最先端-反応の設計と制御" 東京化学同人, 17 (1992)
• [Publications] M.Hirama: "Recent Progress in the Chemical Synthesis of Antibiotics,Vol.2" Springer-Verlag, (1993)
• [Publications] 磯部 稔: "海洋資源と医薬I、続一医薬品の開発" 広川書店, 9 (1991)
• [Publications] 平間 正博: "有機合成の最先端-反応の設計と制御" 東京化学同人, 5 (1992)
• [Publications] 橘 和夫: "化学で探る海洋生物の謎" 化学同人, 8 (1992)
• [Publications] K.Konoki: "Peptide Chemistry 1992" Protein Research FounDation, (1993)
• [Publications] Y.Naya: "Marin Biotechnology,Vol.1:Pharmaceutical and Bioactive Natural Products" Plenum, (1993)