34 てんにんぎく成分Pulchellidine類の絶対構造

スポンサーリンク

概要

• 論文の詳細を見る

• A novel sesquiterpene alkaloid, Pulchellidine (Ia), C_<20>H_<33>O_4N, mp185-186°, was isolated from Gaillardia pulchella Foug. collected near St. Augustin, Florida, along with a minor epimer, Neopulchellidine (Ib), mp131-134°. Pulchellidine (Ia) was converted to a new pseudo-guaianolide, Epipulchellin (IIa), C_<15>H_<22>O_4, mp162-164° by Hofmann degradation of its methiodide. The structures of Ia and IIa were well established on the basis of chemical transformations and several spectral data for the derivatives of III through X. On the other hand, the cultivated species of the same plant (Tenningiku) yielded, on extensive chromatographic separations, Epipulchellin (IIa) mentioned above and an another new epimer, Neopulchellin (IIb), mp166.5-167.5°, along with certain other constituents. The partial syntheses of Ia and Ib were achieved from IIa and IIb, respectively, by addition of piperidin. The stereochemistry of IIa and IIb have been defined as the followings. 1) cis: C_2-α OH/C_4-α OH by sulfites formation and application of Hydson-Klyne rule for dihydro derivatives, VIIa and VIIb. 2) trans: C_1-α H/C_5-β CH_3 from ORD Cotton Effects with Octant rule for dehydro-dihydro derivatives (IIIa, VIIIa and VIIIb), even cis-relationship observed for an equillibrate of VIIIa (VIIIa') and desoxy derivative of VIII (Xa). 3) trans: C_7-α H/C_8-β H for VIIa and cis: C_7-β H/C_8-β H for VIIb on the basis of lactone sector rule with rotations data and reaction rates. 4) C_<10>-α CH_3 and C_<11>-α CH_3 for VIIIa, VIIIb and VIIa, VIIb from certain NMR analyses. 5) C_<11>-α CH_2NC_5H_<10> for Ia and Ib by thermodynamically controlled additions. Finally, the stereostructure of 11, 13-dibromoepipulchellin (X1) evidenced by a complete three-dimensional X-ray analysis confirmed the absolute configuration and sterochemistry described before for Epipulchellin (IIa) as well as Pulchellidine (Ia).

• 天然有機化合物討論会の論文
• 1969-09-01

著者

• 飯高 洋一

  東大薬

• 飯高 洋一

  西東京科学大学理工学部

• 川又 健

  Pharmaceutical Institute, School of Medicine, Keio University

• 稲山 誠一

  慶大医

• 川又 健

  慶大医

• 柳田 昌一

  慶大医

• 稲山 誠一

  Institute Of Oriental Medical Sciences

• 稲山 誠一

  慶應義塾大学医学部薬化学研究所

• 関田 恒二郎

  慶大医

• 川又 健

  Pharmaceutical Institute School Of Medicine Keio University

• 柳田 昌一

  Pharmaceutical Laboratory School Of Medicine Keio University

関連論文

• 23 ^C-^Cおよび^C-^2H couplingを利用した生合成研究
• 47 地衣のトリテルペンの研究 : LobariaおよびPeltigera属について
• 9.Penicillium duclauxi Delacroixの代謝産物について
• 32 ヌクレオシド抗生物質オキザノシンの構造と全合成
• 2 アミノ酸熱分解物中に含まれる変異原物質 : 分離・構造・合成および生物活性
• Chemistry of Tremorogenic Metabolites. II. Structure Determination of Fumitremorgin B, a Tremorogenic Metabolite from Aspergillus fumigatus
• The Structure of Paeoniflorigenone, A New Monoterpene isolated from Paeoniae Radix
• 8 Carbazomycin類抗生物質の単離,構造および生合成
• 5.Ophiobolinの構造
• Synthesis of 1,2,3-Triazine N-Oxides
• THE STRUCTURE OF 1,2,3-TRIAZINE
• ADDITION REACTION OF 1,2,3-TRIAZINE 2-IMINES WITH DIMETHYL ACETYLENEDICARBOXYLATE
• 振動を利用したユーイング装置によるヤング率の測定
• 3p-ZC-14 振動を利用したユーイング装置によるヤング率の測定
• 結晶解析を中心としたSORの利用について
• Chetracin A and Chaetocins B and C, Three New Epipolythiodioxo-piperazines from Chaetomium spp.
• FISSOLDHIMINE, A NOVEL SKELETON ALKALOID FROM FISSISTIGMA OLDHAMII
• Biologically Active Constituents of Magnolia salicifolia : Inhibitors of Induced Histamine Release from Rat Mast Cells
• 94(PB3-5) ビス(ナフト-γ-ピロン)系マイコトキシンの研究(ポスター発表の部)
• 71 多重標識化合物の生合成研究への応用
• 29 抗生物貭Althiomycinの構造決定
• 次亜リン酸カリウムの結晶構造解析 : 粒子線・X線
• Synthetic Studies on Marasmane and iso-Marasmane Derivatives
• The Absolute Configuration of Curcumalactone(Pharmacognosy,Chemical)
• Antitumor Activity of Shikonin, Alkannin and Their Derivatives. II. X-Ray Analysis of Cyclo-alkannin Leucoacetate, Tautomerism of Alkannin and Cyclo-alkannin and Antitumor Activity of Alkannin Derivatives
• 2p-NR-9 32素子MCDDSの性能
• 2p-NR-8 32素子MCSSDの開発
• Studies on Metal Complexes of Isocytosine Derivatives : The Crystal Structures of Mercury(II) and Nickel(II) Complexes of 2-Hydrazino-4-hydroxy-6-methylpyrimidine
• Studies on Metal Complexes of Isocytosine Derivatives : The Molecular Structures of Platinum(II)and Platinum(IV)Complexes of 2-Hydrazino-4-hydroxy-6-methylpyrimidine
• Absolute Configurations of Chaetochromin A and Related Bis(naphtho-γ-pyrone) Mold Metabolites(Organic,Chemical)
• 37 シンジュの苦味成分
• 2p-N-8 多素子SSDシステムとその特性
• 1p-U-2 一次元SSD(PSSD)の開発(III)
• C-Glycosyl Nucleosides. VI. Synthesis and Crystal Structure of Dithiane Glycoside Analog
• シンクロトロン放射-2-構造解析
• シンクロトロン放射X線 (〔応用物理〕創刊50周年記念特集号) -- (放射線検出器への要求と期待)
• Inhibition of Prostaglandin Biosynthesis by 4-O-Methylcryptochlorophaeic Acid ; : Synthesis of Monomeric Arylcarboxylic Acids for Inhibitory Activity Testing and X-Ray Analysis of 4-O-Methylcryptochlorophaeic Acid
• 2 菌類代謝産物の化学 : Rugulosin,Luteoskyrin,Rubroskyrinおよび関連化合物の研究
• タンパク質と核酸の基本構造パラメーターを求める簡単な X 線回折実習
• Ca2+依存性の制御タンパク質トロポニンCとカルモデュリンの立体構造 (1985年の化学-9-)
• THE ABSOLUTE CONFIGURATION AND CONFORMATION OF NEOCURDIONE
• 19 モンタニン型アルカロイド、(±)-モンタニン、(±)-コクシニンの全合成(口頭発表の部)
• Studies on Tetrahydroisoquinolines. XXX. A Synthesis of Mixed Tetrahydroisoquinoline Dimers via p-Quinol Acetates
• Studies on Tetrahydroisoquinolines. XXIII. Reactions of (±)-7-Acetoxy-7-methoxy-1-(3,4-dimethoxy-or 3,4-methylenedioxybenzyl)-2-methyl-6-oxo-Δ^-hexahydroisoquinoline (o-Quinol Acetate)
• Studies on Tetrahydroisoquinolines. XXI. A Synthesis of (±)-1-Hydroxy-2-methoxyhomoproaporphine and Stereochemistry of 4-Oxygenated 1,2,3,4-Tetrahydroisoquinolines
• 77 リコリン関連化合物の合成研究
• 9 Pulchellonの絶対構造と合成
• Constituents of Torilis scabra D.C. II
• 4 Vitamin Dの光増感酸化反応による6,19-epidioxyvitamin D類の合成と反応および生理活性
• Hongconin, a New Naphthalene Derivative from Hong-Cong, the Rhizome of Eleutherine ameicana MERR. et HEYNE(Iridaceae)
• RENEWED STUDIES ON THE STRUCTURE OF DIDYMIC ACID
• Peptides in Higher Plants. II. The Crystal Structure of Tri-N-methylfrangulanine Methiodide
• Structures of Torilolide and Oxytorilolide; Two Novel Germacranolides from Torilis japonica (HOUTT.) DC.
• A Novel Sesquiterpene Peroxide from Alpinia japonica (THUNB.) MIQ.
• Agarofuran-, Eudesmane-and Eremophilane-Type Sesquiterpenoids from Alpinia japonica (THUNB.) MIQ.
• 56 ハナミョウガの成分研究 : 一新セスキテルペンパーオキサイドhanalpinolの構造
• Isolation of Agarofuran-type Sesquiterpenes from Alpinia japonica (THUNB.) MIQ.
• 7 てんにんぎく成分の生合成的関連性
• 4 地衣Usnea bayleyi黄色色素 : Eumitrinの構造について
• Microbiologically Modified Chiral Synthon. III. 4,9-Dimethyl-3,5-dioxo-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids
• A Series of Sesquiterpenes with a 7α-Isopropyl Side Chain and Related Compounds Isolated from Curcuma wenyujin
• MICROBIOLOGICAL ASYMMETRIC INDUCTION OF 4,9-DIMETHYL-3,5-DIOXO-Δ^-OCTALIN
• Microbiologically Modified Chiral Synthon. II. : 4,9-Dimethyl-3,7-dioxo-Δ^-octalin for Formal Total Syntheses of Certain C(8) Oxygenated Sesquiterpenoids
• Microbiologically Modified Chiral Synthon. I. 3,8-Dioxo-4-methoxycarbonyl-9-methyl-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids and Diterpenoids
• MICROBIOLOGICALLY MODIFIED 4,9-DIMETHYL-Δ^-OCTAL-3,7-DIONES AS THE CHIRAL SYNTHON FOR FORMAL TOTAL SYNTHESES OF C(8) OXYGENATED SESQUITERPENOIDS(Communications to the Editor)
• MICROBIOLOGICAL ASYMMETRIC REDUCTION OF 4-CARBOMETHOXY-3,8-DIOXO-9-METHYL-Δ^-OCTALIN
• 60 中国産Curcuma wenyujin(温郁金)の根茎の精油から単離された数種のセスキテルペン成分の絶対構造とその生合成的関連性
• The Complete Structure of Spathulin, a Crystallographic Study of Diacetylspathulin
• 29p-P-13 一次元SSDの開発 (II), データ集録系
• Chemical Studies on the Oriental Plant Drugs. XXXVI. Structure of Licoricone, a New Isoflavone from Licorice Root
• Biologically Active Constituents of Arnebia euchroma : Structures of New Monoterpenylbenzoquinones : Arnebinone and Arnebifuranone
• Biologically Active Constituents of Arnebia euchroma : Structure of Arnebinol, an Ansa-Type Monoterpenylbenzenoid with Inhibitory Activity on Prostaglandin Biosynthesis
• The Absolute Structure and Synthesis of Wenjine Isolated from Curcuma wenyujin
• 5. 分子の形を決める : X 線回折法を中心にして(分析技術 : こんな方法もある)
• The Diels-Alder Reaction of 3-Acetoxy-1-vinylcyclohexene with Methyl Vinyl Ketone
• THE STEREOSTRUCTURE OF WENJINE AND RELATED (1S__-, 10S__-), (4S__-, 5S__-)-GERMACRONE-1(10), 4-DIEPOXIDE ISOLATED FROM CURCUMA WENYUJIN
• THE ABSOLUTE CONFIGURATION OF REGELIDINE, A NOVEL 6-NICOTINOYL DIHYDROAGAROFURAN SESQUITERPENE ALKALOID FROM TRIPTERYGIUM REGELII(Communications to the Editor)
• ISOLATION AND STRUCTURE OF REGELIN AND REGELINOL, NEW ANTITUMOR URSENE-TYPE TRITERPENOIDS FROM TRIPTERYGIUM REGELII(Communication to the Editor)
• G. M. Sheldrick, C. Kruger and R. Goddard 編: Crystallographic Computing 3; Data Collection, Structure Determination, Proteins, and Databases; Papers presented at the International Summer School, Mulheim an der Ruhr, 1984, Oxford University Press, Oxford a
• A NOTE ON THE A-RING CONFORMATION IN 2-CHLORO-1,2-DIHYDROSANTONINS
• EQUILIBRATION OF 2-CHLORO-1,2-DIHYDROSANTONIN CONFORMERS : A THEORETICAL APPROACH USING X-RAY DIFFRACTION AND MO CALCULATIONS
• Thiabenzene誘導体のX線結晶構造
• Studies on Metal Complexes of Isocytosine Derivatives : The Crystal Structure of Copper (II) Complex of 2-Hydrazino-4-hydroxy-6-methylpyrimidine
• Studies on the Chlorinated α-Santonins. II. The Crystal and Molecular Structure of 14-Chlorosantonin
• Crystal Structure of facial-[Bis-(adeninato) (diethylenetriamine)-copper (II)] Monohydrate
• 14 EBELIN LACTONE形成サポニンの真正サポゲニンについて
• 34 てんにんぎく成分Pulchellidine類の絶対構造
• 31p-BF-9 二次元位置検出器を使用したX線結晶構造解析装置
• 5p-L-11 X線回折用二次元検出器
• 結晶構造から見た酵素の反応機構 (セリンプロテアーゼ系を題材として)
• 4. アサガオ未熟種子に含まれるジベレリン複合体pharbitic acidの化学構造と生理活性について
• 半経験的ポテンシャル・エネルギー計算によるホストーゲスト包接化合物中のゲスト位置の決定
• 岡田正和, 分子性結晶 ; 直鎖状分子の結晶多形, 幸書房, 東京, 1975, 236ページ, 21.5×15.5cm, 2,800円
• 10p-Z-11 構造解析
• 桜井敏雄: X線結晶解析, 裳華房, 物理科学選書2, 1967, 400頁, A5判, 1,700円.
• タイトル無し
• タイトル無し
• タイトル無し
• タイトル無し
• タイトル無し

もっと見る 閉じる

スポンサーリンク