1990 Fiscal Year Annual Research Report

植物と植物病原菌に係わる物質の化学的研究

Research Project

Project/Area Number	63303013
Research Institution	Nagasaki University
Principal Investigator	入江寛長崎大学, 薬学部, 教授 (00025686)
Co-Investigator(Kenkyū-buntansha)	藤多哲朗京都大学, 薬学部, 教授 (40027024) 真山滋志神戸大学, 農学部, 助教授 (00112251) 上野民夫京都大学, 農学部, 助教授 (20026579) 津田喜典金沢大学, 薬学部, 教授 (40077508)
Keywords	植物病原菌 / 宿主特異的毒素 / 自己発芽抑制因子 / キノコ類 / プロリン特異的酵素 / 植物の就眠運動 / エンバク冠さび病 / 立体選択的合成反応
Research Abstract	昭和63年度、平成元年度、及び平成2年度の研究成果を以下の項目に分類して述べる。 1:植物病原菌の生産する毒素の化学的研究(入江、上野、野原、藤多)植物病原菌により生産る宿種特異的毒素の単離、構造決定、その全合成、並びにその類縁体を合成し構造と毒性の関係を明らかにした。2:脂質に関連する抗菌薬の開発研究(津田)新しい抗菌剤の開発を志向して、脂質の構造と活性の関係を解明するための合成研究を行なった。3:ファイトアレキシン等の単離、構造、及びその植物生体系における役割の考察(真山)植物病原菌胞子と宿種との間のやり取りを解明するため、焦点をエリシタ-に置き研究を行なった。4:海洋微小藻類に対する生理活性物質の化学的研究(上村)海洋天然物化学の専門を生かし、強力な毒素の単離と構造決定を行なった。5:キノコの生産するプロテア-ゼの研究(芳本)キノコ由来のプロテア-ゼにつき、遺伝子工学を利用してその酵素の量産に関する研究を行なった。6:ペプチド性抗生物質の合成研究(大船)生体内の情報交換に係わるペプチド性化合物の構造から、新たな分子を設計しそれらの合成を行なった。7:植物の生産する超甘味物質の化学的研究(西沢)植物由来の甘味物質の研究を行なった。その間に得た一つの反応は天然物化学に大いに寄与するものである。8:植物の運動を司どる化学物質の単離、構造決定、と合成(志津里)地球の緑化を目指して、葉の開閉運動から進展して気孔の開閉運動にもメスを入れた。9:その他の研究、主として生理活性物質の全合成を志向した合成化学に関する基礎的研究(柴崎、平間、冨岡、塩入、藤井、細見)昆虫が媒体となる植物病は多い。これに関連して昆虫の摂食阻害物質の合成、不斉合性反応の基礎研究、有機金属を用いた新反応の開発研究、ペプチド合成のための新しい保護基の開発研究等を行なった。

Research Products

(35 results)

All Other

All Publications (35 results)

[Publications] Hiroshi Irie: "Synthesis of Methoxyonychine and Use of ^1Hーand ^<13>CーNuclear Magnetic Resonance Spectra for Structure Determination of Geometrical Isomers of Indanー1ーone Oxime Derivatives" Chem.Pharm.Bull.36. 3134-3137 (1988)
[Publications] Jun'ichi Katakawa: "Synthesis of Amaryllidaceae Alkaloids,(±)ーCherylline and (±)ーLatifine" Chem.Pharm.Bull.36. 3928-3931 (1988)
[Publications] Hiroshi Irie: "Synthesis of an Alkaloid,(±)ー3ーDemethoxyerythratidinone" Heterocyles. 29. 1033-1035 (1989)
[Publications] Hiroshi Irie: "Lewis Acid Catalysed Preparation of some Carbamates and Sulphonylureas.Application to the Determination of Enantiomeric Purity of Chiral Alcohols" J.Chem.Soc.,Perkin Trans.I. 1989. 1209-1210 (1989)
[Publications] Junko Koyama: "Synthesis of Alkaloids,Cleistopholine,Oxylopine,(Isoursuline),and Ursuline" Heterocycles. 29. 1649-1654 (1989)
[Publications] Hiroshi Irie: "Synthesis of the Methyl Esters of AKーToxin II,a HostーSpecific Toxin to Japanese White Pear,and Its Congeners;StructureーToxicity Relatioship of the Toxin" Chem.Pharm.Bull.38. 1451-1461 (1990)
[Publications] Hiroshi Irie: "Use of Potassium Peroxodisulfate for Benzylic Oxidation and Oxidative Coupling of Benzoylacetates" SYNLETT. 1990. 421-424 (1990)
[Publications] Hiroshi Irie: "Synthesis of (±)ーHeritol,a Sesquiperpene Lactone belonging to the Aromatic Cadinane Group" Chem.Pharm.Bull.38. 1852-1856 (1990)
[Publications] Hiroaki Sasai: "Zr(OーtーBu)_4,an Efficient and Convenient Basic Reagent in Organic Synthesis.Utilization in Cross and Intramolecular Aldol Reactions" 55. 5306-5308 (1990)
[Publications] Hideo Nakamura: "Alkylated Levoglucosan in Organic Synthesis.A Formal Total Synthesis of Elaiophylin" Chem.Pharm.Bull.,. 38. 2435-2441 (1990)
[Publications] Masahiro Hirama: "New Entry to SynーβーHydroxyーαーAmino Acid" Tetrahedron Letters. 29. 3125-3128 (1988)
[Publications] Kiyoshi Tomioka: "Design,Synthesis,and Antitumor Activity of Steganacin AzaーAnalogues" Tetrahedron Letters. 30. 2949-2952 (1989)
[Publications] Kiyoshi Tomioka: "Conjugate Addition Reaction of Organolithium to Naphthalenecarboxylate" Tetrahedron Letters. 31. 1739-1740 (1990)
[Publications] Akira Hosomi: "Synthesis and Consecutive Double Alkylation Reaction of (2ーSiloxyallyl)silane as the Synthetic Equibalent of Acetone α,α'ーDianion" J.Org.Chem.54. 3254-3256 (1989)
[Publications] Akira Hosomi: "2ーTrimethylsilylethylー1,3ーButadiene as a Synthetic Equivalent of Parent CrossーConjugated Hexatriene,3ーMethyleneー1,4ーPentadiene" Tetrahedron Letters. 31. 6201-6204 (1990)
[Publications] Yasumasa Hamada: "Stereoselective Total Synthesis of AIー77ーB,a Gastroprotective Substance from Bucillus pumilus AIー77" J.Am.Chem.Soc.111. 1524-1525 (1989)
[Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Olefins" Chem.Pharm.Bull.,. 37. 253-256 (1989)
[Publications] Naomi Sakai: "Stereoselective Synthesis of the Revised Structure of Galatanic Acid" Tetrahedron Letters. 31. 4151-4153 (1990)
[Publications] G.Spears: "Palladium Catalized S_<cN'> Reactions.Stereoselective Formation of Cyclic Carbamate from tertーButyldimethylsilyl Carbamate" Tetrahedron Letters. 31. 1060-1061 (1990)
[Publications] Nobitaka Fujii: "Silver Trifluoromethanesulphonate as an SーDeprotecting Reagent for the Synthesis of Cystine Peptide" J.Chem.Soc.,Chem.Commun.,. 1989. 283-284 (1989)
[Publications] Toshiro Ibuka: "Determination of Absolute Configuration of the Alkyl Group at the αーAlkylー(E)ーβ,γーEnoates by Circulae Dichroism" Tetrahedron,Asymmetry. 1. 389-394 (1990)
[Publications] Akira Iida: "Fungal Metabolites IV.Synthesis of an Antibiotic Peptide,Trichosporin BーV,from Trichoderma polysporin" Chem.Pharm.Bull.,. 38. 2997-3003 (1990)
[Publications] Mugio Nishizawa: "αーSelective Thermal Glycosidation of Rhamnosyl and Mannosyl Chlorides" Tetrahedron Letters. 31. 2431-2434 (1990)
[Publications] Hideyuki Takenaka: "Chiral Induction in a Biomimetic Olefin Cyclization" Tetrahedron Letters. 30. 2267-2268 (1989)
[Publications] Yoshikazu Shizuri: "Synthesis of (±)ーSilphinene using Electrochemical Method as a Key Step" Tetrahedron Letters. 30. 3797-3798 (1989)
[Publications] Shosuke Yamamura: "Diterpenes from Euphorbia Helioscopia" Phytochemistry. 28. 3421-3436 (1989)
[Publications] Fumiyuki Kikuchi: "Screening of Crude Drugs Used in Turkey for Nematocidal Activity on the Larva of Toxocara canis" ShoyakugakuZasshi. 43. 353-359 (1989)
[Publications] Hideo Koshida: "Mineralocorticoid and Renal Receptor Binding Acivity of 21ーDeoxyaldosterone" Endocrinology. 126. 1410-1415 (1990)
[Publications] Shoji Yahara: "Structures of AntiーAce and ーRenin Peptides from LYCII Radicis Cortex" Tetrahedron Letters. 30. 6041-6042 (1989)
[Publications] Kazushi Shingu: "Two New Ergostane Derivatives from Tubocapsicum anomalum (Solanaceae)" Chem.Pharm.Bull.,. 38. 1107-1109 (1990)
[Publications] Tadashi Yoshimoto: "An Aminopeptidase N from Escherichia coli HB101:Purification and Demonstration that the Enzyme possesses Arylamidase and Peptidase Activities" Agric.Biol Chem.,. 52. 217-225 (1988)
[Publications] Tadashi Yoshimoto: "Purification and Enzymic Properties of an EndoーaーNーacetyl Galactosaminidase from Bacillus Laterosrus SSー16" J.Ferm.Biotech.,. 70. 348-350 (1990)
[Publications] Tamio Ueno(as a contributor) AttaーurーRahman/Editor: "Stdies in Natural Products Chemistry (Contributor)" Elsevier,
[Publications] Daisuke Uemura AttaーurーRahman/Editor: "Studies in Natural Products Chemistry Vol.5" Elsevier, 24 (1989)
[Publications] Yoshisuke Tsuda (as a contributor): "Studies in Natural Products Chemistry Vol.3" Elsevier, 49 (1989)

1990 Fiscal Year Annual Research Report

植物と植物病原菌に係わる物質の化学的研究

Principal Investigator

入江 寛 長崎大学, 薬学部, 教授 (00025686)

Research Products

[Publications] Hiroshi Irie: "Synthesis of Methoxyonychine and Use of ^1Hーand ^<13>CーNuclear Magnetic Resonance Spectra for Structure Determination of Geometrical Isomers of Indanー1ーone Oxime Derivatives" Chem.Pharm.Bull.36. 3134-3137 (1988)

[Publications] Jun'ichi Katakawa: "Synthesis of Amaryllidaceae Alkaloids,(±)ーCherylline and (±)ーLatifine" Chem.Pharm.Bull.36. 3928-3931 (1988)

[Publications] Hiroshi Irie: "Synthesis of an Alkaloid,(±)ー3ーDemethoxyerythratidinone" Heterocyles. 29. 1033-1035 (1989)

[Publications] Hiroshi Irie: "Lewis Acid Catalysed Preparation of some Carbamates and Sulphonylureas.Application to the Determination of Enantiomeric Purity of Chiral Alcohols" J.Chem.Soc.,Perkin Trans.I. 1989. 1209-1210 (1989)

[Publications] Junko Koyama: "Synthesis of Alkaloids,Cleistopholine,Oxylopine,(Isoursuline),and Ursuline" Heterocycles. 29. 1649-1654 (1989)

[Publications] Hiroshi Irie: "Synthesis of the Methyl Esters of AKーToxin II,a HostーSpecific Toxin to Japanese White Pear,and Its Congeners;StructureーToxicity Relatioship of the Toxin" Chem.Pharm.Bull.38. 1451-1461 (1990)

[Publications] Hiroshi Irie: "Use of Potassium Peroxodisulfate for Benzylic Oxidation and Oxidative Coupling of Benzoylacetates" SYNLETT. 1990. 421-424 (1990)

[Publications] Hiroshi Irie: "Synthesis of (±)ーHeritol,a Sesquiperpene Lactone belonging to the Aromatic Cadinane Group" Chem.Pharm.Bull.38. 1852-1856 (1990)

[Publications] Hiroaki Sasai: "Zr(OーtーBu)_4,an Efficient and Convenient Basic Reagent in Organic Synthesis.Utilization in Cross and Intramolecular Aldol Reactions" 55. 5306-5308 (1990)

[Publications] Hideo Nakamura: "Alkylated Levoglucosan in Organic Synthesis.A Formal Total Synthesis of Elaiophylin" Chem.Pharm.Bull.,. 38. 2435-2441 (1990)

[Publications] Masahiro Hirama: "New Entry to SynーβーHydroxyーαーAmino Acid" Tetrahedron Letters. 29. 3125-3128 (1988)

[Publications] Kiyoshi Tomioka: "Design,Synthesis,and Antitumor Activity of Steganacin AzaーAnalogues" Tetrahedron Letters. 30. 2949-2952 (1989)

[Publications] Kiyoshi Tomioka: "Conjugate Addition Reaction of Organolithium to Naphthalenecarboxylate" Tetrahedron Letters. 31. 1739-1740 (1990)

[Publications] Akira Hosomi: "Synthesis and Consecutive Double Alkylation Reaction of (2ーSiloxyallyl)silane as the Synthetic Equibalent of Acetone α,α'ーDianion" J.Org.Chem.54. 3254-3256 (1989)

[Publications] Akira Hosomi: "2ーTrimethylsilylethylー1,3ーButadiene as a Synthetic Equivalent of Parent CrossーConjugated Hexatriene,3ーMethyleneー1,4ーPentadiene" Tetrahedron Letters. 31. 6201-6204 (1990)

[Publications] Yasumasa Hamada: "Stereoselective Total Synthesis of AIー77ーB,a Gastroprotective Substance from Bucillus pumilus AIー77" J.Am.Chem.Soc.111. 1524-1525 (1989)

[Publications] Toyohiko Aoyama: "Reaction of Trimethylsilyldiazomethane with Olefins" Chem.Pharm.Bull.,. 37. 253-256 (1989)

[Publications] Naomi Sakai: "Stereoselective Synthesis of the Revised Structure of Galatanic Acid" Tetrahedron Letters. 31. 4151-4153 (1990)

[Publications] G.Spears: "Palladium Catalized S_<cN'> Reactions.Stereoselective Formation of Cyclic Carbamate from tertーButyldimethylsilyl Carbamate" Tetrahedron Letters. 31. 1060-1061 (1990)

[Publications] Nobitaka Fujii: "Silver Trifluoromethanesulphonate as an SーDeprotecting Reagent for the Synthesis of Cystine Peptide" J.Chem.Soc.,Chem.Commun.,. 1989. 283-284 (1989)

[Publications] Toshiro Ibuka: "Determination of Absolute Configuration of the Alkyl Group at the αーAlkylー(E)ーβ,γーEnoates by Circulae Dichroism" Tetrahedron,Asymmetry. 1. 389-394 (1990)

[Publications] Akira Iida: "Fungal Metabolites IV.Synthesis of an Antibiotic Peptide,Trichosporin BーV,from Trichoderma polysporin" Chem.Pharm.Bull.,. 38. 2997-3003 (1990)

[Publications] Mugio Nishizawa: "αーSelective Thermal Glycosidation of Rhamnosyl and Mannosyl Chlorides" Tetrahedron Letters. 31. 2431-2434 (1990)

[Publications] Hideyuki Takenaka: "Chiral Induction in a Biomimetic Olefin Cyclization" Tetrahedron Letters. 30. 2267-2268 (1989)

[Publications] Yoshikazu Shizuri: "Synthesis of (±)ーSilphinene using Electrochemical Method as a Key Step" Tetrahedron Letters. 30. 3797-3798 (1989)

[Publications] Shosuke Yamamura: "Diterpenes from Euphorbia Helioscopia" Phytochemistry. 28. 3421-3436 (1989)

[Publications] Fumiyuki Kikuchi: "Screening of Crude Drugs Used in Turkey for Nematocidal Activity on the Larva of Toxocara canis" ShoyakugakuZasshi. 43. 353-359 (1989)

[Publications] Hideo Koshida: "Mineralocorticoid and Renal Receptor Binding Acivity of 21ーDeoxyaldosterone" Endocrinology. 126. 1410-1415 (1990)

[Publications] Shoji Yahara: "Structures of AntiーAce and ーRenin Peptides from LYCII Radicis Cortex" Tetrahedron Letters. 30. 6041-6042 (1989)

[Publications] Kazushi Shingu: "Two New Ergostane Derivatives from Tubocapsicum anomalum (Solanaceae)" Chem.Pharm.Bull.,. 38. 1107-1109 (1990)

[Publications] Tadashi Yoshimoto: "An Aminopeptidase N from Escherichia coli HB101:Purification and Demonstration that the Enzyme possesses Arylamidase and Peptidase Activities" Agric.Biol Chem.,. 52. 217-225 (1988)

[Publications] Tadashi Yoshimoto: "Purification and Enzymic Properties of an EndoーaーNーacetyl Galactosaminidase from Bacillus Laterosrus SSー16" J.Ferm.Biotech.,. 70. 348-350 (1990)

[Publications] Tamio Ueno(as a contributor) AttaーurーRahman/Editor: "Stdies in Natural Products Chemistry (Contributor)" Elsevier,

[Publications] Daisuke Uemura AttaーurーRahman/Editor: "Studies in Natural Products Chemistry Vol.5" Elsevier, 24 (1989)

[Publications] Yoshisuke Tsuda (as a contributor): "Studies in Natural Products Chemistry Vol.3" Elsevier, 49 (1989)

入江寛長崎大学, 薬学部, 教授 (00025686)