升麻素苷H-2 | 161097-77-4

• 物质功能分类: 生物化工 - 中草药成分
• 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: 升麻素苷H-2
• 英文名称: cimicifugoside H-2
• 英文别名: (1S,3R,6S,8R,12R,15R,16R,18S)-15-[(2R,5R)-5,6-dihydroxy-6-methyl-4-oxoheptan-2-yl]-18-hydroxy-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadec-10-en-14-one
• CAS: 161097-77-4
• 化学式: C₃₅H₅₄O₁₀
• 分子量: 634.808
• InChiKey: SUNYLGIAMKNXMN-GLWILYKISA-N

物化性质

• 沸点：
  801.0±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  升麻素苷H-2 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以7 mg的产率得到(3S,5R,9S,10R,11S,13R,14R,17R)-17-((1R,4R)-4,5-Dihydroxy-1,5-dimethyl-3-oxo-hexyl)-3,11-dihydroxy-4,4,13,14-tetramethyl-2,3,5,6,11,12,13,14,15,17-decahydro-1H,4H-cyclopropa[9,10]cyclopenta[a]phenanthren-16-one
  参考文献：
  名称：

  Studies on the Chinese Crude Drug "Shoma." IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1, H-2 and H-5, from Cimicifuga Rhizome.

  摘要：

  Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262°C, [α]D -43.5°, cimicifugoside H-2 (2), C35H54O10, mp 227-229°C, [α]D -38.8°, and cimicifugoside H-5 (3), C35H52O10, mp 262-264°C, [α]D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24, 25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.

  DOI：

  10.1248/cpb.43.771
• 作为产物：
  描述：

  升麻素苷H-1 在 对甲苯磺酸 作用下， 反应 120.0h， 以23 mg的产率得到升麻素苷H-2
  参考文献：
  名称：

  Studies on the Chinese Crude Drug "Shoma." IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1, H-2 and H-5, from Cimicifuga Rhizome.

  摘要：

  Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262°C, [α]D -43.5°, cimicifugoside H-2 (2), C35H54O10, mp 227-229°C, [α]D -38.8°, and cimicifugoside H-5 (3), C35H52O10, mp 262-264°C, [α]D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24, 25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.

  DOI：

  10.1248/cpb.43.771

文献信息

• Constituents of cimicifugae rhizoma II. Isolation and structures of new cycloartenol triterpenoids and related compounds from Cimicifuga foetida L
  作者：Shigetoshi Kadota、Jian Xin Li、Ken Tanaka、Tsuneo Namba

  DOI：10.1016/0040-4020(94)01015-r

  日期：1995.1

  Neutral constituents of Cimicifuga foetida L. were examined. Eight new triterpenoids and three new trinor-triterpenoids were isolated from the rhizoma of C. foetida L. (Ranunculaceae) along with six known compounds and their structures were determined by the use of 2D NMR techniques and chemical methods.

  检查了Cimicifuga foetida L.的中性成分。八个新三萜类化合物和三个新的三去甲-三萜类化合物是从的根茎中分离C.蚓L.（毛茛科）连同6个已知化合物，并且通过使用2D NMR技术和化学方法确定了它们的结构。
• 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.