| 78275-45-3

• 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
• CAS: 78275-45-3
• 化学式: C₃₀H₄₄O₆
• 分子量: 500.676
• InChiKey: LOMNWMLBYJCDQL-JZUVZRBTSA-N

反应信息

• 作为反应物：
  描述：

  在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 以1.5 mg的产率得到3-desoxycimigenol
  参考文献：
  名称：

  Studies on the Chinese crude drug "Shoma." V. Structures of 24-O-acetylhydroshengmanol xyloside and 22-hydroxycimigenol xyloside.

  摘要：

  Two new xylosides were isolated from the underground part of Cimicifuga japonica-24-O-acetylhydroshengmanol xyloside (2), C37H60O11, mp 235-237°, [α]22D+6.6°and 22-hydroxycimigenol xyloside (3), C35H56O10·H2O, mp 282-284°, [α]17D+17.7°. The xyloside (2) afforded, on acid hydrolysis in aq. methanol, cimigenol (4) and isodahurinol (5). Enzymatic hydrolysis of 2 afforded its genuine aglycone 24-O-acetylhydroshengmanol (8), C32H52O7, mp 200-202°, [α]26D+9.0°. The xyloside (2) and its genin (8) showed a mutarotation. When treated at room temperature with sulfuric acid in aq. methanol, 2 changed firstly into 25-O-acetylcimigenol xyloside (6) and finally into cimigenol xyloside (7). On the basis of chemical and spectral data, the structure of 24-O-acetylhydroshengmanol xyloside (2) was proposed to be (23R, 24S)-3β, 15α, 16ξ, 25-tetrahydroxy-24-acetoxy-16, 23-epoxy-9, 19-cyclolanostane 3-O-β-D-xylopyranoside. Another glycoside (3) showed, in its 13C-nuclear magnetic resonance (NMR) spectrum, a pattern of chemical shifts very similar to that of cimigenol xyloside (7), but a downfield shift of C-22 by 44.2 ppm was observed, suggesting oxygenation of C-22 in the glycoside (3). The xyloside (3) afforded, on both acidic and enzymatic hydrolyses, its aglycone (13), C30H48O6, mp 274-276°, [α]19D+45.0°. Huang-Minlon reduction of a diketo derivative (15) of 13 provided a didesoxy compound (16), C30H48O4, mp 202.5-203.5°, which was identical with the 3-desoxy derivative of cimigenol. The stereochemistry of the hydroxyl group at C-22 of 13 was assigned as R on the basis of its NMR spectrum. The structure of 22-hydroxycimigenol xyloside (3) was established as (22R)-22-hydroxycimigenol 3-O-β-D-xylopyranoside.

  DOI：

  10.1248/cpb.29.955
• 作为产物：
  描述：

  22-hydroxycimigenol 在 chromium(VI) oxide 作用下， 以 吡啶 为溶剂， 以4.8 mg的产率得到
  参考文献：
  名称：

  Studies on the Chinese crude drug "Shoma." V. Structures of 24-O-acetylhydroshengmanol xyloside and 22-hydroxycimigenol xyloside.

  摘要：

  Two new xylosides were isolated from the underground part of Cimicifuga japonica-24-O-acetylhydroshengmanol xyloside (2), C37H60O11, mp 235-237°, [α]22D+6.6°and 22-hydroxycimigenol xyloside (3), C35H56O10·H2O, mp 282-284°, [α]17D+17.7°. The xyloside (2) afforded, on acid hydrolysis in aq. methanol, cimigenol (4) and isodahurinol (5). Enzymatic hydrolysis of 2 afforded its genuine aglycone 24-O-acetylhydroshengmanol (8), C32H52O7, mp 200-202°, [α]26D+9.0°. The xyloside (2) and its genin (8) showed a mutarotation. When treated at room temperature with sulfuric acid in aq. methanol, 2 changed firstly into 25-O-acetylcimigenol xyloside (6) and finally into cimigenol xyloside (7). On the basis of chemical and spectral data, the structure of 24-O-acetylhydroshengmanol xyloside (2) was proposed to be (23R, 24S)-3β, 15α, 16ξ, 25-tetrahydroxy-24-acetoxy-16, 23-epoxy-9, 19-cyclolanostane 3-O-β-D-xylopyranoside. Another glycoside (3) showed, in its 13C-nuclear magnetic resonance (NMR) spectrum, a pattern of chemical shifts very similar to that of cimigenol xyloside (7), but a downfield shift of C-22 by 44.2 ppm was observed, suggesting oxygenation of C-22 in the glycoside (3). The xyloside (3) afforded, on both acidic and enzymatic hydrolyses, its aglycone (13), C30H48O6, mp 274-276°, [α]19D+45.0°. Huang-Minlon reduction of a diketo derivative (15) of 13 provided a didesoxy compound (16), C30H48O4, mp 202.5-203.5°, which was identical with the 3-desoxy derivative of cimigenol. The stereochemistry of the hydroxyl group at C-22 of 13 was assigned as R on the basis of its NMR spectrum. The structure of 22-hydroxycimigenol xyloside (3) was established as (22R)-22-hydroxycimigenol 3-O-β-D-xylopyranoside.

  DOI：

  10.1248/cpb.29.955