cimicifugoside H-4 | 161097-79-6

• 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: cimicifugoside H-4
• 英文别名: (1S,2S,4R,5R,6R,9R,10R,12R,16R,18S,21R)-2,9,10-trihydroxy-4,6,12,17,17-pentamethyl-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyhexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-en-8-one
• CAS: 161097-79-6
• 化学式: C₃₂H₄₈O₉
• 分子量: 576.728
• InChiKey: XAOFACFLIBLCBM-UKBVKWQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  41
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cimicifugoside H-4 在 Cellulast 作用下， 以 甲醇 、 水 为溶剂， 反应 168000.0h， 以30 mg的产率得到foetidinol
  参考文献：
  名称：

  来自 Cimicifuga foetida 的一种不寻常的环阿烷烃三萜

  摘要：

  从 Cimicifuge foetida L 的根茎中分离出一种新的环卡坦三萜苷。新化合物的光谱特征与之前描述的环卡坦三萜不同，因为它失去了 24-异丙基以及存在 11β- OH 组。根据光谱证据，包括一系列 2D-NMR 分析，新三萜的结构被指定为 24-des-isopropyl-7-ene-23-one-9,19；16,24-dicycloart-3 beta,11 beta,16 alpha,24 alpha-tetraol 3-O-beta-D-xylopryanoside，这里命名为新西米苷。通过 X 射线分析证实了新西米苷的苷元结构。

  DOI：

  10.1016/0031-9422(95)00895-0
• 作为产物：
  描述：

  升麻素苷H-2 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 cimicifugoside H-3 、 cimicifugoside H-4
  参考文献：
  名称：

  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.

  摘要：

  Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome : cimicifugoside H-3 (1), C32H48O9, mp 249-251 °C, [α]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265-267 °C, [α]D -75.0°, and cimicifugoside H-6 (3), C32H<48>O10, mp 275-276 °C, [α]D -64.3°, On the basis of chemical and spectral data, the structure of 1 was proposed to be 11β, 24-dihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-4 (2), 11β, 16α, 24α-trihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19 : 16, 24-dicyclolanost-7-en-23-one, seems to be generated from intramolecular aldol condensation between C-16 and C-24 of 1. Cimicifugoside H-6 (3) is the 15α-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-1 (4) under an acidic condition, was found to give 1, 2 and an α-hydroxy enone (2a) under an alkaline condition.

  DOI：

  10.1248/cpb.43.1475

文献信息

• 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.
  作者：Nobuko SAKURAI、Mamoru KOEDA、Yoshinobu AOKI、Masahiro NAGAI

  DOI：10.1248/cpb.43.1475

  日期：——

  Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome : cimicifugoside H-3 (1), C32H48O9, mp 249-251 °C, [α]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265-267 °C, [α]D -75.0°, and cimicifugoside H-6 (3), C32H<48>O10, mp 275-276 °C, [α]D -64.3°, On the basis of chemical and spectral data, the structure of 1 was proposed to be 11β, 24-dihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-4 (2), 11β, 16α, 24α-trihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19 : 16, 24-dicyclolanost-7-en-23-one, seems to be generated from intramolecular aldol condensation between C-16 and C-24 of 1. Cimicifugoside H-6 (3) is the 15α-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-1 (4) under an acidic condition, was found to give 1, 2 and an α-hydroxy enone (2a) under an alkaline condition.
• An unusual cycloartane triterpenoid from Cimicifuga foetida
  作者：Cong-Jun Li、Ying-He Li、Pei-Gen Xiao、Tom J. Mabry、William H. Watson、Mariusz Krawiec

  DOI：10.1016/0031-9422(95)00895-0

  日期：1996.5

  A new cycloartane triterpenoid glycoside has been isolated from the rhizomes of Cimicifuge foetida L. The spectroscopic characteristics of the new compound are different from previously described cycloartane triterpenoids because of the loss of the 24-isopropyl group as well as the presence of a 11 beta-OH group. Based on spectroscopic evidence, including a series of 2D-NMR analyses, the structure

  从 Cimicifuge foetida L 的根茎中分离出一种新的环卡坦三萜苷。新化合物的光谱特征与之前描述的环卡坦三萜不同，因为它失去了 24-异丙基以及存在 11β- OH 组。根据光谱证据，包括一系列 2D-NMR 分析，新三萜的结构被指定为 24-des-isopropyl-7-ene-23-one-9,19；16,24-dicycloart-3 beta,11 beta,16 alpha,24 alpha-tetraol 3-O-beta-D-xylopryanoside，这里命名为新西米苷。通过 X 射线分析证实了新西米苷的苷元结构。