24 ミカン科サンショウ属植物イワザンショウ,Xanthoxylum arnottianum,より得られる数種の新クマリンについて
スポンサーリンク
概要
- 論文の詳細を見る
Five new coumarins were isolated from Xanthoxylum arnottianum, Rutaceae, together with ten known ones. Rutaretin Methyl Ether (1): The absolute configuration of rutaretin methyl ether (1) was established as an S by conversion into the diol (16) which was also derived from S-marmesin (3) according to the pathway in Chart 1 and 2. This fact also unequivocally provided a certification for the proposed structure of rutaretin methyl ether (1), although the possibility of the presence of its methoxy group at C_5 position could not be excluded by the reported evidences. Arnottinin (18): The structure of arnottinin, mp 191-193°, involving a Z-configuration on the double bond, was established as the formula (18) by chemical transformation of umbelliferone into arnottinin. (Chart 3). Arnocoumarin (24) and Arnottiacoumarin (25): Arnocoumarin (coumarin I) (24), mp 180-183°, and arnottiacoumarin (coumarin II) (25), mp 140-145°, were derived from S-marmesin (3) and S-rutaretin methyl ether (1), respectively. (Chart 4). Formation of an exo-methylene derivative from a dimethylcarbinol group was performed by treatment with phenylisocyanate. The Biogenetical Situation of the Coumarins Isolated from X. arnottianum: All of the coumarins isolated from X. arnottianum could be arranged according to its oxidative step as shown in Chart 5. It should be noted here that 7-demethylsuberosin (30) would be subject to a si attack by oxygen atom followed by substitution with a phenol group at C_7 to give R-columbianetin (4), while osthenol (21) to a re attack to give S-marmesin (3), although both coumarins are cooccurred in the same plant.
- 天然有機化合物討論会の論文
- 1978-08-22
著者
関連論文
- Total Synthesis of Chelerythrine, a Benzo[c]phenanthridine Alkaloid
- Total Synthesis of Lemaireocereine
- Cesium Fluoride-Mediated Claisen Rearrangement of Aryl Propargyl Ether. Exclusive Formation of 2-Methylarylfuran and Its Availability as a Masked Salicylaldehyde
- 22 フッ化セシウム存在下でのアリールプロパルギルエーテルのクライゼン転位 : 2-メチルアリールフランの生成とそのイソキノリンアルカロイド合成への応用(ポスター発表の部)
- CESIUM FLUORIDE-MEDIATED CLAISEN REARRANGEMENT OF ARYL PROPARGYL ETHER AND ITS APPLICATION TO THE SYNTHESIS OF CHELERYTHRINE
- Fischer Indole閉環反応ならびに関連化合物の研究(第3報) : Acetaldehyde o-MethoxyphenylhydrazoneのC-AcylationならびにC-N^2 Acyl Migration
- 2,5-Dimethoxyphenylhydrazineのp-Phenylenediamine誘導体への転位反応 : Fischer-indole閉環反応における異常成績体
- Studies on the Chemical Constituents of Xanthoxylum nitidum (ROXB.)D. C. (Fagara nitida ROXB.). III. The Chemical Constituents of the Wood
- P-54 Arnottin IおよびArnottin II : 構造、合成、そのBenzo[c]phenanthridine Alkaloidとの生合成的関連性(ポスター発表の部)
- Synthesis of Toddacoumaquinone, a Coumarin-Naphthoquinone Dimer, and Its Antiviral Activities
- Concise Syntheses of the Oxo Derivatives of Benzo[c]phenanthridine Bases by N-Deformylated Cyclization Based on Vilsmeier-Haack Reaction
- 42 Macarpineの合成 : 異常Bischler-Napieralski反応によるAzoniaazulene骨格の形成(口頭発表の部)
- Studies on the Chemical Constituents of Xanthoxylum nitidum (ROXB). D. C. (Fagara nitida ROXB.). II. Examination of the Chemical Constituents by Membrane Filtration : Identification of Magnoflorine, a Water-Soluble Quaternacy Aporphine Alkaloid
- Toddalosin, a New Biscoumarin, from Toddalia asiatica (L.) LAM.(T. aculeate PERS.)
- Synthetic Studies on Naturally Occurring Coumarins. II. Synthesis of 6,7-Dimethoxy- and 7,8-Dimethoxy-5-[(E)-3-oxo-1-butenyl]coumarins
- 67 ToddacoumaloneならびにToddacoumaquinone : クマリンを基調とした新規混合二量化体(ポスター発表の部)
- Fischer Indolization and Its Related Compounds. XIX. Syntheses of Ethyl 4-Methoxy- and Ethyl 5-Methoxy-1-phenyl-3H-benz [e] indole-2-carboxylates
- Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
- 高次有機銅試薬を用いるgem-ジブロモシクロプロパン体のアルキル化反応について
- Fischer Indolization of Ethyl Pyruvate 2-[2-(Trifluoromethyl)phenyl]-phenylhydrazone and New Insight into the Mechanism of the Goldberg Reaction. (Fischer Indolization and Its Related Compounds. XXVI)
- Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II. : Synthesis of Bromo- and Methoxycarbonylcoumarins
- A Convenient Preparation of Salicylaldehydes from 2-Methylbenzofurans by Ozonolysis
- Synthetic Studies on Naturally Occurring Coumarins. I. A Convenient Synthesis of 5,8-Dimethoxy- and 7,8-Dimethoxycoumarins
- TODDACOUMAQUINONE, A UNIQUE COUMARIN-NAPHTHOQUINONE DIMER, FROM TODDALIA ASIATICA (L.) LAM. (T. ACULEATA PERS.)
- A CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN
- 37 Lysergic acid誘導体の微生物代謝と関連化学
- Re-examination of the Synthesis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinylphenyl)iso carbostyril
- ミカン科植物成分の研究(第66報)沖縄産サルカケミカン, Toddalia asiatica(L.)LAM.(T.aculeata PERS.), の成分 その1 根皮の成分
- Fischer Indolizationにおける異常反応とその新反応への展開
- Studies on the Chemical Constituents of Rutaceous Plants. L. Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (2). Preparation of 2-Aryl-1-tetralone Derivatives
- Chelirubine
- 40 Chelirubineの構造と合成
- ミカン科植物成分の研究(第21報)イワザンショウXanthoxylum arnottianum MAXIM.の成分その2幹の木質部の検索
- Studies on the Chemical Constituents of Rutaceous Plants. LX. Development of a Versatile Method for Syntheses of the Antitumor Benzo [c] phenanthridine Alkaloids. (9). Efficient Syntheses and Antitumor Activities of Nitidine and Related Nonphenolic Benzo
- O-Methyldeoxopunjabine, a Secobisbenzylisoquinoline Alkaloid Bearing an Aryl Methyl Group, and Three Other Secobisbenzylisoquinoline Alkaloids, O-Methylpunjabine, Secocepharanthine, and Dihydrosecocepharanthine, from Stephania Sasakii
- Studies on the Chemical Constituents of Rutaceous Plants. LI. Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (3). Detailed Examination of the Synthesis of 2-Aryl-1-formamido-1,2,3,4-tetrahydrona
- 14 セファランチンを中心としたビスベンジルイソキノリン型アルカロイドの化学における新展開
- Studies on the Alkaloids of Menispermaceous Plants. CCLXXV. Syntheses of [methylenedioxy-^C] Cepharanthine and a Related Compound
- Studies on the Chemical Constituents of Rutaceous Plants. LV. The Development of a Versatile Method for the Synthesis of Antitumor Active Benzo [c] phenanthridine Alkaloids. (5). A New Method for Quaternization of the Benzo [c] phenanthridine Nucleus
- Studies on the Chemical Constituents of Rutaceous Plants. LIV. The Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (4). Limitation of Bischler-napieralski Cyclization and Detailed Examination of
- Structural Establishment of Chelilutine Due to the Chemical Correlation with Nitidine and Isoarnottianamide
- Fischer Indolization and Its Related Compounds. XVIII. Formation of Four Unexpected Angular Benz [e] indoles on Fischer Indolization of Ethyl Phenylpyruvate 2-[(1,4-Dimethoxy-2-naphthyl) hydrazone]
- 日本学術振興会
- 新学術会議会員に聞く
- 世界の特許情勢の大動乱期
- Abnormal Fischer Indolization and Its Related Compounds. XII. Synthesis of 3,6'-Biindole
- Fischer Indolization and Its Related Compounds. VIII. Formation of 4-Aminoindole Derivatives on the Fischer Indolization of 2-Methoxyphenylhydrazone Derivatives
- 39 The advanced Fischer Indolization of 2-Methoxyphenylhydrazonesを用いた天然産6-置換インドール類の合成
- Fischer Indolization and Its Related Compounds. VI. Effect of Reagents and Substituent of the ortho-Substituted Phenylhydrazone on Abnormal Fischer Indolization
- Development of "Abnormal" Fischer Indolization to Syntheses of 3,6'-Biindole and Its Derivatives
- 2,3-Diphenyl-7-hydroxyindole ならびに N-Methyl 体のFremy's Saltによる酸化方向 : 複素環キノン類の研究(第1報)
- 医薬品の特許
- Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone
- Fischer Indolization and Its Related Compounds. XXIII. Fischer Indolization of Ethyl Pyruvate 2-(2,6-Dimethoxyphenyl)phenylhydrazone
- Sanguirubine and Sanguilutine
- ミカン科植物成分の研究(第59報)台湾産テリハザンショウ, Xanthoxylum nitidum(ROXB.)D.C.(Fagara nitida ROXB.), の成分 その1皮部のアルカロイド含有部の検索
- Fremy塩による酸化(第7報)数種の5-置換-1-ナフトール類の合成
- Structure of Serratanidine
- 有機天然化合物の化学は、今……
- ミカン科植物アルカロイド研究(第18報) : カラスザンショウXanthoxylum ailanthoides SIEB. et ZUCC.(Fagara ailanthoides(SIEB.et ZUCC.) ENGL.)のアルカロイド その2 根部のアルカロイド
- ミカン科植物成分の研究(第67報)台湾産サルカケミカン, Toddalia asiatica(L.)LAM.(T.aculeata PERS.), の成分 超臨界流体並びにソックスレー抽出法を用いた含有クマリンの検討.Toddalolactoneは真の天然産クマリンか?
- Studies on Lysergic Acid Diethylamide and Related Compounds. IX. Microbial Transformation of Amides Related to Lysergic Acid Diethylamide by Streptomyces roseochromogenes
- Studies on Lysergic Acid Diethylamide and Related Compounds. VII. Microbial Transformation of Lysergic Acid Diethylamide and Related Compounds
- Studies on the Chemical Constituents of Rutaceous Plants. XLVI. The Chemical Constituents of Xanthoxylum integrifoliolum (MERR.) MERR. (Fagara integrifoliola MERR.) II. Structural Establishment of Integriquinolone, a New Phenolic Quinolone
- PHOTOCHEMISTRY OF 2-(3,4,5-TRIMETHOXYPHENYL)-4-(3,4-METHYLENEDIOXYPHENYL)-4-OXO-2-BUTENONITRILE (β-CYANOCHALCONE) : ANOMALOUS DIMERIZATION THROUGH ISOMERIZATION IN THE SOLID STATE
- AILANTHOIDINE, A NOVEL BENZO[C]PHENANTHRIDINE ALKALOID WITH A CYANOPYRIDINE PENDANT, FROM A XANTHOXYLUM SPECIES
- New Indole Trimer
- 薬学の野球戦士達
- Fischer Indolization and Its Related Compounds. V. Indolization of Ethyl Pyruvate 2-Methoxyphenylhydrazone and Its N-Methyl Derivative with Protic Acids. Unpredictable Products and the Mechanism
- Abnormal Fischer Indolization and Its Related Compounds. XXII. : Fischer Indolization of Ethyl Pyruvate 2-(2-Chloro- and 2,6-Dichlorophynyl)methylhydrazones
- 日本薬学会奨励賞受賞 竹内義雄氏の業績
- 製薬企業発行の情報誌
- Studies on the Chemical Constituents of Rutaceous Plants. LXIV. Structural Establishment of Oxyterihanine, a Phenolic Benzo[c]phenanthridone Alkaloid. Syntheses of Phenolic Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Related Compou
- 59 Intramolecular Basic Acylationを用いたフェノール性抗腫瘍Benzo[c]phenanthridine Alkaloidの合成法の確立
- Studies on the Chemical Constituents of Rutaceous Plants. LVI. The Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (6). Limitation of the Dyke Synthetic Pathway for Benzo [c] phenanthridine Alkal
- The Plane Structure of Serratinine
- Serratinine ; A Novel Skeletal Lycopodium Alkaloid
- Fremy塩による酸化(第6報)数種の5-アルキル(ならびにフェニル)-1-ナフトール類の合成
- Oxidation of 6-Methyl-2-phenylbenzofuran with Chromic Acid under Various Conditions. An Abnormal Dimeric Oxidation Product of the Benzofuran Derivative. Studies on the Heterocyclic Quinones. V
- 数種の複素環キノン類ならびに関連化合物の核磁気共鳴スペクトル : 4-Hydroxy-2-phenylbenzoxazoleならびに1-Hydroxydibenzo-p-p-dioxinのFremy's Saltによる酸化方向 : 複素環キノン類の研究(第4報)
- 7-Hydroxy-2-および-3-phenylbenzo[b]thiophene類のFremy′s Saltによる酸化方向 : 3-Phenyl基の立体的影響 : 複素環キノン類の研究(第3報)
- 7-Hydroxy-2,3-diphenylbenzofuran ならびに-benzo[b]thiopheneのFremy's Saltによる酸化方向 : 複素環キノン類の研究(第2報)
- Studies on the Chemical Constituents of Rutaceous Plants. XXXVI. Synthesis of Ethyl Isodecarine
- 37 エナミド光閉環反応を用いた天然物の合成
- 分析室の中から
- Studies on Lysergic Acid Diethylamide and Related Compounds. V. Syntheses of Dihydrolysergic Acid Diethylamides and Related Compounds
- 薬学概論
- Lysergic Acid Diethylamideおよび関連化合物に関する研究(第4報)Norlysergic Acidの各種Amide誘導体ならびに関連化合物の合成
- 比旋光度やORDの濃度の表示
- The Structures of Two Lycopodium Alkaloids, Lycothunine and Lycophlegmarine, and the Configuration of the C_3-C_4 Bond of Fawcettimine and Fawcettidine
- 抗腫瘍性ベンゾ[c]フェナンスリジン・アルカロイドの化学
- 支部例会の講演要旨の取り扱いに対する一私案
- Lycopodium Alkaloid, Serratanineの構造について
- 新しき薬学への出発 : 旧制から新制へ
- UrgencyとNovelty
- (+)-Peucedanol Methyl Ether from Hippomarathrum cristatum, Umbelliferae
- フィッシャー・インドール閉環反応とその関連化合物の研究(第13報)シフト試薬を用いたインドール-2-カルボン酸エステル誘導体の核磁気共鳴スペクトルの測定とその応用
- Structural Establishment of Arnocoumarin and Arnottiacoumarin due to Chemical Modification of Marmesin and Rutaretin Methyl Ether
- 43 Benzo〔c〕phenanthridine型alkaloidの合成法の検討
- Studies on the Chemical Constituents of Rutaceous Plants. XXXV. Structural Establishment and Synthesis of Bocconoline. Photochemical Reaction of a Benzo [c] phenanthridinium Salt with Methanol