15 ガガイモ科植物成分の研究 : sarcostin等の二・三の反応及び20位の配位
スポンサーリンク
概要
- 論文の詳細を見る
a) Partial acetylation of sarcostin (1) gave two diacetate; 3,12 diacetate (3) and 3,20 diacetate (4) with the ratio of 3:1, besides 3-mono acetate (2) and 3,12,20-triacetate (5). On the other hand, benzoylation of 2 with equimolar amount of BzCl gave 20-benzoate (6). b) Treatment of 1 with paraldehyde under acid catalyzed conditions afforded 14,17 and 12,20 bis-O-cyclic ethylidene derivative (14). c) The configuration of C-20 carbinol of 1 is S-configuration on the basis of X-ray analysis of 3-p-bromobenzoate (17). C-20-o-Nitrobenzoate (18) showed a negative Cotton effect contrary to the expection from Nagai's data but the 14,17-O-ethylidene derivative (19) showed a positive Cotton effect. d) It has been known that reduction of pregnan-20-one with metal hydride gives β-alcohol (R-configuration). It is deduced, however, that the stereochemistry of the C-20-carbinol from the orresponding ketone by NaBH_4 reduction dues to the configuration at C-17 position regardless of C/D ring juncture from the conformational analyses of pregnan-20-one derivatives by the ORD octant rule (Fig. A and B). The C-20-O-o-nitrobenzoate (25) from the reduction of lineolondiacetate (24) with NaBH_4 shows a positive Cotton effect while the o-nitrobenzoate (27) from isolineolondiacetate (26) shows a negative. These results agree with the deduction.
- 天然有機化合物討論会の論文
- 1974-10-01
著者
-
三橋 博
Research Institute For Biology & Chemistry Tsumura & Co.
-
林 紘司
Tsumura Central Research Laboratories Tsumura & Co.
-
三橋 博
北大・薬
-
林 紘司
北大・薬
関連論文
- Syntheis and Protective Effect of 1,3,5-Triazine Derivatives, Leukotriene C^4 Antagonist, on HCl・Ethanol-Induced Gastric Lesions in Rats
- 35 Emericella heterothallicaの産生する新規エピポリチオジオキソピペラジン誘導体およびその関連化合物(口頭発表の部)
- I-B-29 茵〓蒿の Aldose Reductase 阻害物質
- Further Investigation of Antitumor Condurangoglycosides with C-18 Oxygenated Aglycone
- 65 ガガイモ科植物成分の研究 : コンズランゴ皮中の抗腫瘍性配糖体の分離と構造
- Antitumor Active Glycosides from Condurango Cortex
- Studies on the Constituents of Asclepiadaceae Plants. XLIX. Confirmation of the Structures of Antitumor-active Glycosides in Condurango Cortex. Chemical Transformation of the Aglycone Moiety
- 48 コンズランゴ皮中の抗腫瘍性配糖体の研究 : アグリコン部の化学変換について
- 27 ガガイモ科植物の成分 : Glycocynanchogeninの構造 ^C Pulse Fourier Transform(PFT)NMRのC/D cis polyoxypregnaneの構造決定への応用
- II-B-7 半夏の迷走神経胃枝遠心性活動賦活作用について
- Studies on the Constituents of Asclepiadaceae Plants. XLV. On the Components of Metaplexis japonica MAKINO. VI. The Structures of 7-Oxygenated-Pregnane Derivatives
- Components of Metaplexis japonica MAKINO
- Studies on the Constituents of Asclepiadaceae Plants. XVIII. Components of Cynanchum paniculatum KITAGAWA
- Studies on the Constituents of Asclepiadaceae Plants. XX. Epimerization at C-17 and Optical Rotatory Dispersion Study of C/D cis Pregnan-20-one Derivatives. 2
- Studies on the Constituents of Asclepiadaceae Plants. XIX. Components of Metaplexis japonica MAKINO. IV.
- Studies on the Constituents of Asclepiadaceae Plants. XVI. On the Components of Metaplexis japonica MAKINO. III. The Structure of benzoylramanone.
- Studies on the Constituents of Asclepiadaceae Plants. XV. On the Components of Metaplexis japonica MAKINO. II
- Studies on the Constituents of Asclepiadaceae Plants. XIV. Structure of Tomentogenin
- On the Structure of Pergularin
- 15.C/D-cis-pregnane-20-one型化合物の側鎖の異性化及び旋光分散について
- On the Structure of Tomentogenin
- On the Structure of Metaplexigenin and Benzoylramanone
- Studies on the Constituents of Asclepiadaceae Plants. XI. Separation of New Aglycones from Cynanchum caudatum MAXIM.
- Studies on the Constituents of Asclepiadaceae Plants. IX. On the Components of Cynanchum caudatum MAX.
- Studies on the Constituents of Asclepiadaceae Plants. VIII. On the Components of Metaplexis japonica MAKINO. 1.
- Studies on the Constituents of Asclepiadaceae Plants. VII. Paper Chromatographic Separation of Steroidal Aglycones in Asclepiadaceae Plants.
- Studies on the Constituents of Asclepiadaceae Plants. VI. On the Components of Marsdenia tomentosa DECNE.
- 28.CynanchogeninおよびPenupogeninの構造
- ISOLATION OF NEW SAPONINS FROM THE ROOT OF BUPLEURUM FALCATUM L.
- Marine Sterols. XI. Polyhydroxysterols of the Soft Coral Sarcophyton glaucum : Isolation and Synthesis of 5α-Cholestane-1β, 3β, 5,6β-tetrol
- Studies on the Constituents of Umbelliferae Plants. VI. Studies on the Constituents of Angelica edulis MIYABE. (2).
- Studies on the Constituents of Umbelliferae Plants. V. Studies on the Constituents of Angelica edulis MIYABE. (1). Isolation of Edultin.
- 10-Hydroxypheophytins and a New Norlabdane Diterpene from the Leaves of Cupressus funebris ENDL.
- Studies on the Constituents of Umbelliferae Plants. XVIII. : Minor Constituents of Bupleuri Radix : Occurrence of Saikogenins, Polyhydroxysterols, a Trihydroxy C_ Fatty Acid, a Lignan and a New Chromone
- Marine Terpenes and Terpenoids. V. : Oxidation of Sarcophytol A, a Potent Anti-tumor-Promoter from the Soft Coral Sarcophyton glaucum
- Inhibitors of Adenosine 3', 5'-Cyclic Monophosphate Phosphodiesterase from Schisandra chinensis and the Structure Activity Relationship of Lignans
- Four New Phenolic Glycosides from Polygala tenuifolia
- Gomisin A(TJN-101)の体内動態に関する研究(第1報)ラットにおける吸収
- Benzoylgomisin Q and Benzoylgomisin P, Two New Lignans from Schisandra sphenanthera REHD. et WILS.
- Studies on the Metabolism of Gomisin A (TJN-101). II. : Structure Determination of Biliary and Urinary Metabolites in Rat
- Studies on the Constituents of Asclepiadaceae Plants. LXVI. The Structures of Three New Glycosides, Cynapanosides A, B, and C, from the Chinese Drug "Xu-Chang-Qing, " Cynanchum paniculatum KITAGAWA
- 28 ガガイモ科Cynanchum属のプレグナン配糖体について
- Studies on the Constituents of Asclepiadaceae Plants. LXV. : The Optical Resolution of D- and L-Cymaroses
- Studies on the Constituents of Asclepiadaceae Plant. LXIV. : The Structure Elucidation of Cynafogenin
- The Constituents of Schizandra chinensis BAILL. XV. : Isolation and Structure Determination of Two New Lignans : Gomisin S and Gomisin T
- Studies on the Metabolism of Gomisin A (TJN-101). I. : Oxidative Products of Gomisin A Formed by Rat Liver S9 Mix.
- Revised Structure of a Novel Disaccharide, Wilforibiose, Obtained from the Hydrolysate of Cynanchum wilfordi HEMSLEY Glycosides
- Studies on the Constituents of Asclepiadaceae Plants. LXII. The Structures of Two Glycosides, Cynafoside-A and -B, with a Novel Sugar Chain Containing a Pair of Optically Isomeric Sugars, D- and L-Cymaroses, from Cynanchum africanum R. BR.
- Studies on the Constituents of Asclepiadaceae Plants. LXI. The Structure of Cynatratoside-F from the Chinese Drug "Pai-Wei, " Dried Root of Cynanchum atratum BUNGE
- 70 ガガイモ科植物成分の研究 : 光学異性の一対の糖(D-cymarose及びL-cymarose)を構成糖とするCynanchum wilfordi並びにC. africanumの配糖体について
- Studies on the Constituents of Asclepiadaceae Plants. LX. Further Studies on Glycosides with a Novel Sugar Chain Containing a Pair of Optically Isomeric Sugars, D- and L-Cymarose, from Cynanchum wilfordi
- Studies on the Constituents of Asclepiadaceae Plants. LIX. The Structures of Five New Glycosides from Dregea volubilis (L.) BENTH.
- Studies on the Constituents of Asclepiadaceae Plants. LVIII. The Structures of Five Glycosides, Cynatratoside-A, -B, -C, -D, and -E, from the Chinese Drug "Pai-Wei, " Cynanchum atratum BUNGE
- ガガイモ科植物成分の研究--生理活性を有する配糖体の分離と構造
- Studies on the Constituents of Asclepiadaceae Plants. LVI. Isolation of New Antitumor-Active Glycosides from Dregea volubilis (L.) BENTH.
- 27 ガガイモ科植物成分の研究 : ガガイモ科配糖体の構成オリゴ糖並びに^CNMRについて
- Studies on the Constituents of Asclepiadaceae Plants. LV. The Structures of Three New Glycosides, Glaucoside-H, -I, and -J from the Chinese Drug "Pai-ch'ien, "Cynanchum glaucescens HAND-MAZZ
- Studies on the Constituents of Asclepiadaceae Plants. LIV. The Structures of Glaucoside-F and -G from the Chinese Drug "Pai-ch'ien, " Cynanchum glaucescens HAND-MAZZ
- Studies on the Constituents of Asclepiadaceae Plants. LIII. The Structures of Glaucogenin-A, -B, and -C Mono-D-thevetoside from the Chinese Drug "Pai-ch'ien, "Cynanchum glaucescens HAND-MAZZ
- Studies on the Constituents of Asclepiadaceae Plants. LI. Oxidation at the 18-Methyl Group of C/D-cis-Pregnane Type Steroids and ^C-Nuclear Magnetic Resonance Spectra of 18-Oxygenated Pregnanes and Related Compounds
- Studies on the Constituents of Asclepiadaceae Plants. L. Two New Oligoglycosides, Cynanchoside C_2 and Cynanchoside C_1,from Cynanchum caudatum MAX.
- 61 ガガイモ科植物成分の研究イケマのオリゴ配糖体について
- Syntheses of Steroids having a Bakkenolide-Type Spirolactone Ring. I. Synthesis of 4'-Methylenedihydrospiro-[5α-cholestane-3,3'(2'H)-furan]-2'-one
- 11 ガガイモ科植物成分の研究 : 漢薬芫花葉白前の配糖体について
- Marine Terpenes and Terpenoids. II. Structures of Three Cembrane-type Diterpenes, Sarcophytol-C, Sarcophytol-D, and Sarcophytol-E, from the Soft Coral, Sarcophyton glaucun Q. et. G
- Studies on the Constituents of Asclepiadaceae Plants. XLVIII. 5α, 6α-Epoxycaudatin, a New Polyoxypregnane Derivative from Cynanchum caudatum MAX.
- Studies on the Constituents of Asclepiadaceae Plants. XLVII. Acyl Migration of Polyoxypregnane Derivatives
- Studies on the Constituents of Asclepiadaceae Plants. XLVI. Aglycones form Stephanotis japonica MAKINO
- Cynanchoside C_2,a New Steroidal Oligoglycoside from Cynanchum caudatum MAX. : Applycation of ^C-NMR Spectroscopy to the Structural Elucidation of Plant Glycosides
- 81 シタキソウに含まれるC/D-cis polyoxypregnane esterの構造について : ガガイモ科植物成分の研究
- Studies on the Constituents of Asclepiadaceae Plants. XLIV. Components of Cynanchum caudatum MAX. Structure of 20-O-Cinnamoylsarcostin, 12-O-Cinnamoylikemagenol and 20-O-Cinnamoylikemagenol
- Structure of Stephanthraniline A
- Studies on the Constituents of Asclepiadaceae Plants. XLIII. Component of Marsdenia tomentosa DECNE. Structure of Tomentomin
- Studies on the Constituents of Asclepiadaceae Plants. XLII. Component of Marsdenia tomentosa DECNE. Structure of 12β-O-Acetyltomentogenin and Hypothetical Biogenetic Pathway of Polyoxypregnanes in M. tomentosa
- Studies on the Constituents of Asclepiadaceae Plants. XLI. Component of Cynanchum caudatum MAX. Structure of Glycopenupogenin
- Studies on the Constituents of Asclepiadaceae Plants. XXXIX. Component of Marsdenia tomentosa DECNE : Structure of Deacetyldehydrotomentodin, 20-O-Acetylpenupogenin, Deacetylkidjoladinin, and Kidjoladinin
- 40 ガガイモ科植物成分の研究 : キジョランの成分研究及びその生合成
- Studies on the Constituents of Asclepiadaceae Plants. XXXVIII. Component of Cynanchum caudatum MAX. Structure of Glycocaudatin
- Constituents of Asclepiadaceae Plants. XXXVII. Component of Marsdenia tomentosa DECNE : Structure of Deacetyltomentosin and Tomentidin
- The Synthesis of 3-Spirooxindole Derivatives. IX. The Reactions of 2-Hydroxytryptamine with Hemiacetals
- Studies on the Constituents of Asclepiadaceae Plants. XXXVI. Component of Marsdenia tomentosa DECNE : Structure of Tomentonin, Tomentodin, and Dehydrotomentosin and Difference in the Reactivity between Utendin and Tomentogenin Diesters on Mild Alkaline Hy
- Constituents of Asclepiadaceae Plants. XXXV. Component of Marsdenia tomentosa DECNE. Structure of Tomentin and Dehydrotomentin
- Studies on the Constituents of Asclepiadaceae Plants. XXXIV. Chemistry of Sarcostin
- Constituents of Asclepiadaceae Plants. XXXIII. Component of Marsdenia tomentosa DECNE. Structure of Tomentosin
- Studies on the Constituents of Asclepiadaceae Plants. XXXII. : Aglycones from Cynanchum wilfordi HEMSLEY
- 15 ガガイモ科植物成分の研究 : sarcostin等の二・三の反応及び20位の配位
- Constituents of Asclepiadaceae Plants. XXXI. Component of Stapelia grandiflora MASS
- Synthesis of Bakkenolide A
- The Structure and Internal Acyl Migration of Gagaminin
- On the Tentative Structure of Wilforine
- On the Structure of Kidjolanin and the Position of the Esterlinkage of Penupogenin
- Integerrimine from Cacalia hastata L. subsp. orientalis KITAMURA
- Synthesis of a Heterocyclic Ring Steroid Rearrangements of C-nor-steroid
- Studies on the Constituents of Asclepiadaceae Plants. XXIX. Mass Spectra of C/D cis Pregnane Derivatives
- Constituents of Rhodea japonica ROTH
- Components of Adonis Plants
- Studies on the Constituents of the Asclepiadaceae Plants. XXVIII. Components of Asclepias syriaca L.
- Studies on the Constituents of Asclepiadaceae Plants. XXVI. Isolation of a New Glycoside from Dreges volubilia (L.) BENTH.
- Studies on the Constituents of Asclepiadaceae Plants. XXIV. Structure of Stephanol
- Isolation and Structures of New Pregnane Derivatives from Adonis amurensis REGEL et RADD