升麻环氧醇苷 | 27994-11-2

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 升麻环氧醇苷
• 中文别名: 升麻醇-3-O-Β-D-吡喃木糖甙；升麻醇-3-O-β-D-吡喃木糖苷；升麻醇-3-O-Beta-D-吡喃木糖苷
• 英文名称: cimigenol-3-O-β-D-xylopyranoside
• 英文别名: cimigenol-3-O-β-D-xyloside；cimigenoside；Cimigenol xyloside；(2S,3R,4S,5R)-2-[[(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-2-hydroxy-22-(2-hydroxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
• CAS: 27994-11-2
• 化学式: C₃₅H₅₆O₉
• 分子量: 620.824
• InChiKey: BTPYUWOBZFGKAI-XYGBCAHESA-N

物化性质

• 熔点：
  269-271 °C
• 沸点：
  740.3±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8°C

制备方法与用途

生物活性

Cimigenoside 是升麻属中的一种有效成分。

化学性质

Cimigenoside 为类白色结晶体，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于铁破锣的根茎。

用途

• 升麻醇-3-O-β-D-吡喃木糖苷具有清热解毒的作用。
• Cimigenoside 可用于含量测定、鉴定及药理实验等。

药理药效

Cimigenoside 具有清热解毒的功效。

反应信息

• 作为反应物：
  描述：

  升麻环氧醇苷 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 D-吡喃木糖
  参考文献：
  名称：

  来自 Cimicifuga foetida Linnaeus 地上部分的环烷烃三萜类化合物

  摘要：

  Cycloartane 三萜、2',24-O-diacetylisodahurinol-3-O-α-L-arabinopyranoside、24-O-acetylisodahurinol-3-O-α-L-arabinopyranoside、12β-hydroxy-25-anhydrocimigenol、cimigenol-12-一、12β-羟基-15-脱氧香茅醇、2'-O-乙酰基-24-epi-cimigenol-3-O-α-L-阿拉伯吡喃糖苷、2'-O-乙酰基香茅醇-3-O-β-D-吡喃木糖苷， 25-anhydrocimigenol-3-O-α-L-arabinopyranoside, 2',23-O-diacetylshengmanol-3-O-α-L-arabinopyranoside, 和 2',24-O-diacetyl-25-anhydroshengmanol-3-O -α-

  DOI：

  10.1016/j.phytochem.2011.03.022
• 作为产物：
  描述：

  2'-O-acetylcimigenol-3-O-β-D-xylopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 升麻环氧醇苷
  参考文献：
  名称：

  来自 Cimicifuga foetida Linnaeus 地上部分的环烷烃三萜类化合物

  摘要：

  Cycloartane 三萜、2',24-O-diacetylisodahurinol-3-O-α-L-arabinopyranoside、24-O-acetylisodahurinol-3-O-α-L-arabinopyranoside、12β-hydroxy-25-anhydrocimigenol、cimigenol-12-一、12β-羟基-15-脱氧香茅醇、2'-O-乙酰基-24-epi-cimigenol-3-O-α-L-阿拉伯吡喃糖苷、2'-O-乙酰基香茅醇-3-O-β-D-吡喃木糖苷， 25-anhydrocimigenol-3-O-α-L-arabinopyranoside, 2',23-O-diacetylshengmanol-3-O-α-L-arabinopyranoside, 和 2',24-O-diacetyl-25-anhydroshengmanol-3-O -α-

  DOI：

  10.1016/j.phytochem.2011.03.022

文献信息

• Chlorination Diversifies <i>Cimicifuga racemosa</i> Triterpene Glycosides
  作者：Shao-Nong Chen、David C. Lankin、Dejan Nikolic、Daniel S. Fabricant、Zhi-Zhen Lu、Benjamin Ramirez、Richard B. van Breemen、Harry H. S. Fong、Norman R. Farnsworth、Guido F. Pauli

  DOI：10.1021/np0700319

  日期：2007.6.1

  (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art quality control measures involve phytochemical fingerprinting of the triterpene glycosides for species identification and chemical standardization by HPLC. In the course of developing materials and methods for standardization procedures, the major C. racemosa triterpene glycoside (1) was isolated

  黑升麻（Cimicifuga racemosa）的根和根茎提取物被广泛用作膳食补充剂，以缓解更年期症状。最先进的质量控制措施包括三萜糖苷的植物化学指纹图谱，以通过HPLC进行物种鉴定和化学标准化。在开发用于标准化程序的材料和方法的过程中，主要的消旋C. racemosa三萜糖苷（1）被分离出来，最初被认为是西咪呋藤苷（2）。对1和2的详细HR-LC-MS以及1D和2D NMR分析明确表明，1是2的含氯衍生物，即25-氯脱氧嘧啶醇-3-O-β-d-木糖苷。因此，黑色升麻制剂的HPLC谱图需要修改氯化（1）和非氯化（2）对的分配。除了解释极性的显着变化（DeltatR [RP-18]大约20分钟）外，25-脱氧氯化还为三萜糖苷化学打开了结构多样化的新途径。由于可以证明从2到1的化学转化，脱氧氯化可以解释为伪影形成。然而，同时，它是相对极性的三萜糖苷在胃中体内转化（“自然的前药”）成药理学性质改
• Bioactivity-Guided Isolation of GABA_A Receptor Modulating Constituents from the Rhizomes of <i>Actaea racemosa</i>
  作者：Serhat S. Cicek、Sophia Khom、Barbara Taferner、Steffen Hering、Hermann Stuppner

  DOI：10.1021/np100479w

  日期：2010.12.27

  Black cohosh (Actaea racemosa) is a frequently used herbal remedy for the treatment of mild climacteric symptoms. In the present study, the modulation of gamma-aminobutryic acid (GABA)-induced chloride currents (I-GABA) through GABA type A (GABA(A)) receptors by black cohosh extracts and isolated compounds was investigated. GABA(A) receptors, consisting of alpha(1), beta(2), and gamma(2S) subunits, were expressed in Xenopus laevis oocytes, and potentiation of I-GABA was measured using the two-microelectrode voltage clamp technique. In a bioactivity-guided isolation procedure the positive modulation of I-GABA could be restricted to the plant terpenoid fractions, resulting in the isolation of 11 cycloartane glycosides, of which four significantly (p < 0.05) enhanced I-GABA. The most efficient effect was observed for 23-O-acetylshengmanol 3-O-beta-D-xylopyranoside (4, 100 mu M), enhancing I-GABA by 1692 +/- 201%, while actein (1), cimigenol 3-O-beta-D-xylopyranoside (6), and 25-O-acetylcimigenol 3-O-alpha-L-arabinopyranoside (8) were significantly less active. In the absence of GABA, only 4 induced small (not exceeding 1% of IGABA-max) chloride inward currents through GABA(A) receptors. It is hypothesized that the established positive allosteric modulation of GABA(A) receptors may contribute to beneficial effects of black cohosh extracts in the treatment of climacteric symptoms.
• Cycloartane triterpenoids from the aerial parts of Cimicifuga foetida Linnaeus
  作者：Yin Nian、Xian-Min Zhang、Yan Li、Yuan-Yuan Wang、Jian-Chao Chen、Lu Lu、Lin Zhou、Ming-Hua Qiu

  DOI：10.1016/j.phytochem.2011.03.022

  日期：2011.8

  were isolated from aerial parts of Cimicifuga foetida. Their structures were determined by application of spectroscopic analyses and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, SK-BR-3, and PANC-1 cell lines indicated that three of these compounds exhibited broad-spectrum and moderate cytotoxic activities, with IC₅₀ values ranging from 6.20 to 22.74

  Cycloartane 三萜、2',24-O-diacetylisodahurinol-3-O-α-L-arabinopyranoside、24-O-acetylisodahurinol-3-O-α-L-arabinopyranoside、12β-hydroxy-25-anhydrocimigenol、cimigenol-12-一、12β-羟基-15-脱氧香茅醇、2'-O-乙酰基-24-epi-cimigenol-3-O-α-L-阿拉伯吡喃糖苷、2'-O-乙酰基香茅醇-3-O-β-D-吡喃木糖苷， 25-anhydrocimigenol-3-O-α-L-arabinopyranoside, 2',23-O-diacetylshengmanol-3-O-α-L-arabinopyranoside, 和 2',24-O-diacetyl-25-anhydroshengmanol-3-O -α-