23-O-acetylshengmanol | 62498-92-4

• 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
• 英文名称: 23-O-acetylshengmanol
• 英文别名: 23-O-Acetylshengmanol；[(1R,3R)-3-[(1S,3R,6S,8R,11R,12S,13R,15R,16R)-6,13-dihydroxy-7,7,12,16-tetramethyl-14-oxo-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-1-[(2S)-3,3-dimethyloxiran-2-yl]butyl] acetate
• CAS: 62498-92-4
• 化学式: C₃₂H₅₀O₆
• 分子量: 530.745
• InChiKey: XEVRMEYBJMMBCW-ISHIJLPDSA-N

物化性质

• 沸点：
  623.0±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  23-O-乙酰基-升麻新醇木糖苷 在 alpha-L-rhamnosidase 作用下， 反应 72.0h， 以14 mg的产率得到23-O-acetylshengmanol
  参考文献：
  名称：

  Bioactivity-Guided Isolation of GABA_A Receptor Modulating Constituents from the Rhizomes of Actaea racemosa

  摘要：

  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.

  DOI：

  10.1021/np100479w

文献信息

• 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.