Kamaladiol | 135545-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Kamaladiol
• 英文别名: 3β,22β-Dihydroxyolean-18-ene；(3S,4aR,6aS,6aR,6bR,8aR,9R,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,6a,7,8,9,10,13,14,14a-tetradecahydropicene-3,9-diol
• CAS: 135545-91-4
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: QLJVMDQFEPGVPZ-YBVHTWAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Kamaladiol 在 jones' reagent 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 (4aR,6aR,6bR,8aR,12bS,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,4a,5,6,6a,6b,7,8,8a,10,11,12b,13,14,14a,14b-hexadecahydro-2H,4H-picene-3,9-dione
  参考文献：
  名称：

  Kamaladiol-3-acetate from the stem bark of Mallotus philippinensis

  摘要：

  The first olean-18-ene triterpene oxidized at C-22 has been isolated from the stem bark of Mallotus philippinensis along with friedelin. Its structure was elucidated as 3beta-acetoxy-22beta-hydroxyolean-18-ene.

  DOI：

  10.1016/s0031-9422(00)95004-0
• 作为产物：
  描述：

  Kamaladiol-3-acetate 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 4.0h， 生成 Kamaladiol
  参考文献：
  名称：

  Kamaladiol-3-acetate from the stem bark of Mallotus philippinensis

  摘要：

  The first olean-18-ene triterpene oxidized at C-22 has been isolated from the stem bark of Mallotus philippinensis along with friedelin. Its structure was elucidated as 3beta-acetoxy-22beta-hydroxyolean-18-ene.

  DOI：

  10.1016/s0031-9422(00)95004-0

文献信息

• Periandradulcins A, B and C: Phosphodiesterase inhibitors from Periandra dulcis Mart.
  作者：Yoshitaka IKEDA、Masanori SUGIURA、Chikara FUKAYA、Kazumasa YOKOYAMA、Yohei HASHIMOTO、Kazuko KAWANISHI、Midori MORIYASU

  DOI：10.1248/cpb.39.566

  日期：——

  During the course of our screening of bioactive natural products, three new saponins named periandradulcins A (1), B (2) and C (3) were isolated as phosphodiesterase (PDE, EC 3.1.4.17) inhibitors from 80% MeOH extract of the roots of Periandra dulcis MART. (Leguminosae) by a combination of column chromatography and reversed- and normal-phase high-performance liquid chromatography (HPLC). On the basis of -1H, 13C- and two-dimensional nuclear magnetic resonance (NMR) spectral data and chemical evidence, their chemical structures were characterized as 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-hydroxyl-25-formylolean-18-ene-22β-O-syringate, 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-22β-hydroxyl-25-formylolean-12-ene and 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranosyl]-22β-hydroxyl-25-formylolean-18-ene, respectively.The concentrations of periandradulcins A, B and C required to give 50% inhibition (IC50 values) of PDE from bovine heart, were 0.033, 7.6 and 7.7 μM, respectively. Compound 1 was the most potent among the known PDE inhibitors; it inhibited PDE-I (IC50 : 0.0022 μM) twenty and forty times more effectively than PDE-II and -III, respectively.

  在筛选生物活性天然产物的过程中，我们通过柱层析、反相和正相高效液相色谱法（HPLC）相结合的方法，从豆科植物 Periandra dulcis MART. 的根部 80% MeOH 提取物中分离出了三种新的皂苷，分别命名为 Periandradulcins A (1)、B (2) 和 C (3)，作为磷酸二酯酶（PDE，EC 3.1.4.17）抑制剂。(通过柱色谱法和反相与正相高效液相色谱法（HPLC）相结合的方法，从 Periandra dulcis MART 的根部 80% MeOH 提取物中分离出磷酸二酯酶（PDE）抑制剂。根据-1H、13C 和二维核磁共振（NMR）光谱数据和化学证据，确定其化学结构为 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-羟基-25-formylolean-18-ene-22β-O-丁环酸酯、3-O-β-[α-L-吡喃鼠李糖基（1→2）-β-D-吡喃木糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基]-22β-羟基-25-formylolean-12-烯和 3-O-β-[α-L-吡喃鼠李糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基]-22β-羟基-25-formylolean-18-烯、分别为对牛心脏中的 PDE 产生 50% 抑制作用所需的 Periandradulcins A、B 和 C 浓度（IC50 值）分别为 0.033、7.6 和 7.7 μM。在已知的 PDE 抑制剂中，化合物 1 的效力最强；它对 PDE-I 的抑制作用（IC50：0.0022 μM）分别是 PDE-II 和 PDE-III 的 20 倍和 40 倍。