Studies on the Chinese Crude Drug "Shoma."V. Structures of 24-O-Acetylhydroshengmanol Xyloside and 22-Hydroxycimigenol Xyloside
スポンサーリンク
概要
- 論文の詳細を見る
Two new xylosides were isolated from the underground part of Cimicifuga japonica-24-O-acetylhydroshengmanol xyloside (2), C_<37>H_<60>O_<11>, mp 235-237°, [α]^<22>_D+6.6°and 22-hydroxycimigenol xyloside (3), C_<35>H_<56>O_<10>・H_2O, mp 282-284°, [α]^<17>_D+17.7°. The xyloside (2) afforded, on acid hydrolysis in aq. methanol, cimigenol (4) and isodahurinol (5). Enzymatic hydrolysis of 2 afforded its genuine aglycone 24-O-acetylhydroshengmanol (8), C_<32>H_<52>O_7,mp 200-202°, [α]^<26>_D+9.0°. The xyloside (2) and its genin (8) showed a mutarotation. When treated at room temperature with sulfuric acid in aq. methanol, 2 changed firstly into 25-O-acetylcimigenol xyloside (6) and finally into cimigenol xyloside (7). On the basis of chemical and spectral data, the structure of 24-O-acetylhydroshengmanol xyloside (2) was proposed to be (23R, 24S)-3β, 15α , 16ξ, 25-tetrahydroxy-24-acetoxy-16,23-epoxy-9,19-cyclolanostane 3-O-β-D-xylopyranoside. Another glycoside (3) showed, in its ^<13>C-nuclear magnetic resonance (NMR) spectrum, a pattern of chemical shifts very similar to that of cimigenol xyloside (7), but a downfield shift of C-22 by 44.2 ppm was observed, suggesting oxygenation of C-22 in the glycoside (3). The xyloside (3) afforded, on both acidic and enzymatic hydrolyses, its aglycone (13), C_<30>H_<48>O_6,mp 274-276°, [α]^<19>_D+45.0°. Huang-Minlon reduction of a diketo derivative (15) of 13 provided a didesoxy compound (16), C_<30>H_<48>O_4,mp 202.5-203.5°, which was identical with the 3-desoxy derivative of cimigenol. The stereochemistry of the hydroxyl group at C-22 of 13 was assigned as R on the basis of its NMR spectrum. The structure of 22-hydroxycimigenol xyloside (3) was established as (22R)-22-hydroxycimigenol 3-O-β-D-xylopyranoside.
- 公益社団法人日本薬学会の論文
- 1981-04-25
著者
-
永井 正博
星薬科大学
-
井上 隆夫
星薬科大学
-
井上 隆夫
Hoshi College of Pharmacy
-
永井 正博
Hoshi College of Pharmacy
-
永井 正博
星薬大
-
木村 修
星薬科大学
-
桜井 信子
Hoshi College of Pharmacy
-
木村 修
Hoshi College of Pharmacy
関連論文
- N-カフェオイルアミノ酸類の血管平滑筋弛緩作用
- Studies on the Constituents of Aceraceae Plants. V. Two Diarylheptanoid Glycosides and an Arylbutanol Apiosylglucoside from Acer nikoense
- Studies on the Constituents of Aceraceae Plants. IV. Carbon-13 Nuclear Magnetic Resonance Spectra of Acerogenin A, Rhododendrol and Related Compounds, and Structure of Aceroside IV from Acer nikoense
- Studies on the Constituents of Aceraceae Plants. III. Strucure of Acerogenin B from Acer nikoense MAXIM.
- 38 メグスリノキより得られる2つの新しいヘテロサイド : diarylheptanolとarylbutanolのapiosylglucosides
- Studies on the Constituents of Aceraceae Plants. II. Structure of Aceroside I, a Glucoside of a Novel Cyclic Diarylheptanoid from Acer nikoense MAXIM.
- カエデ科植物の成分研究(第1報)メグスリノキの葉および樹皮の成分
- ヤチヤナギからの新規トリテルペノイドMyricalactone及び数種のトリテルペノイド
- THREE NOVEL CYCLOLANOSTANOL XYLOSIDES FROM CIMICIFUGA RHIZOME
- A New Lignan, (-)-Berchemol, from Berchemia racemosa
- キクニガナ及びスギナより得られたカフェー酸エステルの血管平滑筋弛緩作用
- 生薬升麻の基源であるサラシナショウマ属及び近縁植物の成分
- Diarylheptanoids from Myrica gale var. tomentosa and Revised Structure of Porson
- Studies on the Chinese Crude Drug "Shoma." X. Three New Trinor-9,19-cyclolanostanol Xylosides, Cimicifugosides H-3,H-4 and H-6,from Cimicifuga Rhizome and Transformation of Cimicifugoside H-1 into Cimicifugosides H-2,H-3 and H-4
- Studies on the Chinese Crude Drug "Shoma". IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1,H-2 and H-5,from Cimicifuga Rhizome
- 実験的肝障害に対するクマヤナギの防護効果
- Studies on the Chinese Crude Drug "Shoma." VIII. Two New Triterpenol Bisdesmosides, 3-Arabinosyl-24-O-acetylhydroshengmanol 15-Glucoside and 3-Xylosyl-24-O-acetylhydroshengmanol 15-Glucoside, from Cimicifuga dahurica
- Studies on the Constituents of Beesia calthaefolia and Souliea vaginata. IV. Beesioside I, a Cyclolanostanol Xyloside from the Rhizomes of Beesia calthaefolia
- 実験的肝障害に対する楊梅皮の防護効果(生薬学)
- Berchemolide, a Novel Dimeric Vanillic Acid Glucoside from Berchemia racemosa
- 放射線障害防護薬剤に関する研究(第30報)川〓中の放射線障害防護物質
- Constituents of Myrica rubra. III. : Structures of Two Glycosides of Myricanol
- 放射線障害防護薬剤に関する研究(第25報)生薬類の放射線障害防護効力
- Studies on the Constituents of Beesia calthaefolia and Souliea vaginata. II. : Beesioside II, a Cyclolanostanol Xyloside from Rhizomes of Beesia calthaefolia
- 放射線障害防護薬剤に関する研究(第24報)四物湯の放射線障害防護効力
- Studies on the Constituents of Aceraceae Plants. VII. : Diarylheptanoids from Acer griseum and Acer triflorum
- Studies on the Constituents of Aceraceae Plants. VI. : Revised Stereochemistry of (-)-Centrolobol, and New Glycosides from Acer nikoense
- ^C-核磁気共鳴スペクトルにおけるオルト置換フェノールのO-メチル化効果(第2報)
- Studies on the Constituents of Iris florentina L. II. C-Glucosides of Xanthones and Flavones from the Leaves
- Carbon-13 Nuclear Magnetic Resonance Spectral Study. Effect of O-Methylation of ortho-Substituted Phenols on the Aryl Carbon Shielding and Its Application to Interpretation of the Spectra of Some Flavonoids
- ニオイイリスの成分研究(第1報)地下部に含まれるC-Glucosylxanthoneの単離およびそれらの生合成
- Biosynthesis of Mangiferin in Anemarrhena asphodeloides BUNGE. II. C-Glucosylation of Mangiferin
- Biosynthesis of Mangiferin in Anemarrhena asphodeloides BUNGE. I. The Origin of the Xanthone Nucleus
- センブリに含まれるフラボン-C-配糖体の生合成
- Protosappanin A, a Novel Biphenyl Compound from Sappan Lignum
- 蘇木からBrazilinの生合成前駆体といわれるSappanchalconeの分離
- カシワバハグマの苦味成分 : Glucozaluzanin C
- Studies on the Constituents of Aceraceae Plants. XII. Two New Diarylheptanoid Glycosides from Acer triflorum
- 生薬「升麻」に関する研究(第7報)北升麻および同属近縁植物からの真正配糖体Acetyl Shengmanol Xyloside, 24-O-Acetylhydroshengmanol XylosideおよびShengmanol Xylosideの単離と定量
- 生薬「升麻」に関する研究(第6報)サラシナショウマ属トリテルペン配糖体の新しい真正配糖体Shengmanol Xyloside
- Studies on the Chinese Crude Drug "Shoma."V. Structures of 24-O-Acetylhydroshengmanol Xyloside and 22-Hydroxycimigenol Xyloside
- ナガバノコウヤボウキから得られるセスキテルペノイドと青葉アルコール配糖体及びコウヤボウキのセスキテルペン配糖体
- 連翹より得られたForsythiasideの血管平滑筋弛緩作用
- Studies on the Constituents of Aceraceae Plants. XI. Two Types of Cyclic Diarylheptanoid from Acer nikoense
- 知母のサポニン成分について
- Protosappanins E-1 and E-2,Stereoisomeric Dibenzoxocins Combined with Brazilin from Sappan Ligunm
- New Glucosides of a 4-Hydroxy-5-methylcoumarin and a Dihydro-α-pyrone from Gerbera jamesonii hybrida
- Cyanogenic Glycosides and 4-Hydroxycoumarin Glycosides from Gerbera jamesonii hybrida
- 天然由来のフェノールカルボン酸類の血管平滑筋弛緩作用について (第15回天然薬物の開発と応用シンポジウム講演要旨集) -- (一般講演)
- 楊梅皮のDiarylheptanoid
- 第22回天然有機化合物討論会
- ムラサキシキブおよびオオムラサキシキブ葉から4′, 5,6,7-Tetramethoxyflavoneの分離
- Studies on the Constituents of Saxifragaceous Plants. I. Two Triterpene Acids of Peltoboykinia tellimoides (MAXIM.) HARA
- Bitter Principles of Pertya glabrescens : Two Sesquiterpene Glucosides
- New Sesquiterpene Dilactone from Pertya glabrescens
- Two Glycosides of a Novel Dammarane Alcohol from Gynostemma pentaphyllum
- カシワバハグマの新四環性トリテルペンおよび近縁植物のトリテルペン成分
- Biosynthesis of Puerarin in Pueraria Root
- Biosynthesis of Isoflavone C-Glycoside in Pueraria Root
- Studies on the Constituents of Sambucus chinensis LINDL.
- Studies on Biogenesis of Tea Components. III. The Origin of the Methyl Groups in Caffeine.
- Studies on Biogenesis of Tea Components. II. Formation of Caffeine in Excised Tea Shoots.
- 過ヨード酸およびシクロヘキシルアミンによる配糖体の加水分解法およびその糖部-非糖部結合決定の可能性
- メグスリノキ及びヤマモモの成分.Diarylheptanoidを中心として
- Sambucus属植物の成分研究(第2報)エゾニワトコ葉の成分
- Studies on the Chinese Crude Drug "Shoma." IV. Structure of Acetyl Shengmanol Xyloside, a Probable Precursor of some Known Cimicifuga Glycosides
- Acetyl Shengmanol, a Possible Parental Triterpene Acetate of Cimigenol and Cimigol from Cimicifuga japonica
- 生薬「升麻」に関する研究(第3報)イヌショウマのトリテルペン配糖体および25-Anhydrocimigenol Arabinosideの構造
- イチジク葉の血圧下降成分
- 生薬「升麻」に関する研究(第1報) : 北升麻および和升麻(黒升麻)よりフェノールカルボン酸の分離
- センボンヤリの4-ヒドロキシクマリン配糖体
- メグスリノキ樹皮のラット四塩化炭素肝障害に対する防護効果
- カエデ科植物の成分研究(第7報) : メゲスリノキ心材のクマリノリゲナンについて