methyl β-D-cymaropyranoside | 67968-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-cymaropyranoside
• 英文别名: methyl-β-D-cymaropyranoside；methyl β-D-cymaropyranose；methyl β-cymaropyranoside；β-D-cymaropyranose；methyl cymaroside；Methyl-β-dl-cymarosid；(2R,3R,4S,6R)-4,6-dimethoxy-2-methyloxan-3-ol
• CAS: 67968-33-6
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: WHDBCFVBMDLPAF-ULAWRXDQSA-N

物化性质

• 沸点：
  256.5±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 caudatin 、 methyl β-D-cymaropyranoside
  参考文献：
  名称：

  Cytotoxicity of pregnane glycosides of Cynanchum otophyllum

  摘要：

  Fourteen new pregnane glycosides, including nine caudatin glycosides (1-9), three qinyangshengenin glycosides (10-12), one kidjoranin glycosides (13) and one gagaminin glycosides (14), along with twelve known analogs (15-26) were isolated from roots of Cynanchum otophyllum Schneid. Their structures were deduced by detailed analysis of 1D and 2D NMR spectra, as well as HRESIMS. In this study, all pregnane glycosides obtained (1-26) were evaluated for their cytotoxic activities using three cancer cell lines (HepG2, Hela, U251). As results, except 6 and 10, other twenty-four pregnane glycosides showed cytotoxicities at different degrees against three cell lines. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.08.010

文献信息

• Studies on the constituents of Asclepiadaceae plants. L. Two new oligoglycosides, cynanchoside C2 and cynanchoside C1, from Cynanchum caudatum Max..
  作者：KEIJI WADA、KOJI HAYASHI、HIROSHI MITSUHASHI、HIDEO BANDO

  DOI：10.1248/cpb.30.3500

  日期：——

  Two new steroidal oligoglycosides, named cynanchoside C2 (1a) and cyanchoside C1 (2a), were isolated from the rhizome of Cynanchum caudatum MAX. The structures of 1a and 2a were elucidated by the application of 13C-nuclear magnetic resonance spectroscopy and chemical reactions.

  从牛皮消根中分离得到两种新的甾体低聚糖苷，分别命名为牛皮消苷C2（1a）和牛皮消苷C1（2a）。通过应用13C核磁共振波谱和化学反应阐明了1a和2a的结构。
• Indonesian Medicinal Plants. I. Chemical Structures of Calotroposides A and B, Two New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae).
  作者：Isao KITAGAWA、Ru-song ZHANG、Jong Dae PARK、Nam In BAEK、Yasuyuki TAKEDA、Masayuki YOSHIKAWA、Hirotaka SHIBUYA

  DOI：10.1248/cpb.40.2007

  日期：——

  Two new oxypregnane-oligoglycosides named calotroposides A (1) and B (2) have been isolated from the root of Calotropis gigantea (Asclepiadaceae), an Indonesian medicinal plant, and their chemical structures have been elucidated by chemical and spectroscopic methods as 12-O-benzoyllineolon 3-O-β-D-cymaropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside and 12-O-benzoylde-acetylmetaplexigenin 3-O-β-D-cymaropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside, respectively.

  从印度尼西亚药用植物Calotropis gigantea（夷果科）的根中分离出两种新型氧孕烷寡糖苷，分别命名为calotroposides A (1) 和B (2)。通过化学和光谱方法阐明了它们的化学结构，分别为12-O-苯甲酰林诺酮 3-O-β-D-醋酸甲酰基(1→4)-β-D-油菜糖基(1→4)-β-D-油菜糖基(1→4)-β-D-醋酸甲酰基(1→4)-β-D-醋酸甲酰基苷和12-O-苯甲酰-去乙酰基甲基生物雌激素 3-O-β-D-醋酸甲酰基(1→4)-β-D-油菜糖基(1→4)-β-D-油菜糖基(1→4)-β-D-醋酸甲酰基(1→4)-β-D-醋酸甲酰基苷。
• Studies on the constituents of Asclepiadaceae plants. LXV The optical resolution of D- and L-cymaroses.
  作者：SACHIKO TSUKAMOTO、KOJI HAYASHI、KOH KANEKO、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.34.3130

  日期：——

  The carbamoyl derivatives of enantiomeric mixtures of methyl α- and β-cymaropyranosides were resolved by high-performance liquid chromatography (HPLC).

  通过高效液相色谱法（HPLC）分离了甲基 α- 和 β-吡喃香豆素对映体混合物的氨基甲酰基衍生物。
• 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.
  作者：SACHIKO TSUKAMOTO、KOJI HAYASHI、HIROSHI MITSUHASHI、FRIEDRICH OTTO SNYCKERS、THEUNIS GERHARDUS FOURIE

  DOI：10.1248/cpb.33.4807

  日期：——

  Two glycosides named cynafoside-A (1) and -B (2) were isolated from Cynanchum africanum R. BR. (Asclepiadaceae) which is toxic to stock in South Africa. Their structures were determined on the basis of spectral and chemical evidence, and are unusual in that they include both D-and L-cymaroses in the sugar chain.

  从对南非的牲畜有毒的 Cynanchum africanum R. BR.（Asclepiadaceae）中分离出两种苷，分别命名为 cynafoside-A（1）和-B（2）。它们的结构是根据光谱和化学证据确定的，其不寻常之处在于糖链中同时包含 D 和 L-香豆素。
• Brimacombe, John S.; Al-Hasan, Ziyad; Mengech, Annalee S., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1800 - 1803
  作者：Brimacombe, John S.、Al-Hasan, Ziyad、Mengech, Annalee S.

  DOI：——

  日期：——