泽泻醇A | 19885-10-0

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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
• 中文名称: 泽泻醇A
• 中文别名: 泽泻萜醇A；泽泻醇 A
• 英文名称: alisol A
• 英文别名: (5R,8S,9S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-17-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 19885-10-0
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: HNOSJVWYGXOFRP-UNPOXIGHSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  629.3±55.0 °C(Predicted)
• 密度：
  1.14
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

制备方法与用途

生物活性

泽泻醇A（Alisol A）是一种天然产物。

化学性质

泽泻醇A为白色针状结晶，可溶于甲醇、乙醇及DMSO等有机溶剂。它来源于泽泻根茎。

用途

泽泻醇A具有降血脂和胆固醇以及抗过敏的作用，并可用于含量测定、鉴定和药理实验等。

药理药效

研究表明，当本品与含有1%胆固醇、2%胆酸钠及0.2%氯化胆碱的食物同时喂养雄性大鼠时，在十天后测量治疗组和对照组血液中胆固醇含量，发现本品能明显降低血液中的胆固醇水平。

反应信息

• 作为反应物：
  描述：

  泽泻醇A 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以41.0 mg的产率得到13β,17β-epoxyalisol A
  参考文献：
  名称：

  Crude Drugs from Aquatic Plants. I. On the Constituents of Alismatis Rhizoma. (1). Absolute Stereostructures of Alisols E 23-Acetate, F, and G, Three New Protostane-Type Triterpenes from Chinese Alismatis Rhizoma.

  摘要：

  从中国泽泻根茎（中国四川省采集的水生植物东方泽泻的干燥根茎（日文为 Sentaku））的极性较低的部分中，分离出了三种新的原烷型三萜类化合物，分别命名为泽泻醇 E 23-乙酸酯、F 和 G，以及四种愈创木型倍半萜类化合物和几种已知的三萜类化合物，包括 13，17-表紫苏醇 A。根据化学和物理化学证据，包括 E 23-乙酸烯醇、F 和 G 与已知三萜类烯醇 A 和 A 24-乙酸酯的化学相关性，以及应用改进的莫舍尔法，确定了 E 23-乙酸烯醇、F 和 G 的绝对立体结构。

  DOI：

  10.1248/cpb.41.1948
• 作为产物：
  描述：

  alisol F 在 lithium 、 乙二胺 作用下， 反应 1.5h， 以0.7 mg的产率得到dihydroalisol A
  参考文献：
  名称：

  Crude Drugs from Aquatic Plants. I. On the Constituents of Alismatis Rhizoma. (1). Absolute Stereostructures of Alisols E 23-Acetate, F, and G, Three New Protostane-Type Triterpenes from Chinese Alismatis Rhizoma.

  摘要：

  从中国泽泻根茎（中国四川省采集的水生植物东方泽泻的干燥根茎（日文为 Sentaku））的极性较低的部分中，分离出了三种新的原烷型三萜类化合物，分别命名为泽泻醇 E 23-乙酸酯、F 和 G，以及四种愈创木型倍半萜类化合物和几种已知的三萜类化合物，包括 13，17-表紫苏醇 A。根据化学和物理化学证据，包括 E 23-乙酸烯醇、F 和 G 与已知三萜类烯醇 A 和 A 24-乙酸酯的化学相关性，以及应用改进的莫舍尔法，确定了 E 23-乙酸烯醇、F 和 G 的绝对立体结构。

  DOI：

  10.1248/cpb.41.1948

文献信息

• Anti-HBV agents. Part 1: Synthesis of alisol A derivatives: A new class of hepatitis B virus inhibitors
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Pi Cheng、Yun-Bao Ma、Xue-Mei Zhang、Feng-Xue Zhang、Jun Zhou、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2008.07.012

  日期：2008.8

  A series of alisol A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. The preliminary investigation demonstrates that simple modifications of the parent structure of alisol A can produce a number of potentially important derivatives against HBV. The most active anti-HBV compound 6a showed high activities against the secretion

  合成了一系列alisol A衍生物，并对其抗乙型肝炎病毒（HBV）活性和体外细胞毒性进行了评估。初步研究表明，简单修饰alisol A的母体结构可以产生许多潜在的抗HBV重要衍生物。最具活性的抗HBV化合物6a对HBV表面抗原（IC（50）= 0.024 mM），HBV e抗原（IC（50）= 0.028 mM）的分泌具有很高的活性，并且具有显着的选择性指数（SI（HBsAg）> 108，SI（HBeAg）> 93），被选作新型HBV抑制剂作进一步评估。
• Anti-HBV agents. Part 2: Synthesis and in vitro anti-hepatitis B virus activities of alisol A derivatives
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Ji-Feng Liu、Yun-Bao Ma、Rui-Hua Guo、Xue-Mei Zhang、Jun Zhou、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2009.02.122

  日期：2009.4

  Chemical modi. cations were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure-activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg > 90, SIHBeAg > 93). (C) 2009 Elsevier Ltd. All rights reserved.
• Anti-HBV agents. Part 3: Preliminary structure–activity relationships of tetra-acylalisol A derivatives as potent hepatitis B virus inhibitors
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Yun-Bao Ma、Ji-Feng Liu、Rui-Hua Guo、Xue-Mei Zhang、Jun Zhou、Wei Niu、Fei-Fei Du、Li Li、Chuan Li、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2009.10.006

  日期：2009.12

  Thirty-two tetra-acylated derivatives of alisol A were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. Among the series of alisol A derivatives examined, five analogues were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells. These results also provide interesting structure-activity relationships of tetra-acylalisol A derivatives. Compounds tetra-acetyl alisol A (A1), tetra-methoxyacetyl alisol A (A23), and tetra-ethoxyacetyl alisol A (A24) exhibited high activities against secretion of HBsAg with IC50 values of 0.0048, 0.0044, and 0.014 mM, respectively, HBeAg with IC50 values of 0.011, 0.012, and 0.018 mM, respectively, and remarkable selective index values SIHBsAg > 333, SIHBeAg > 145; SIHBsAg = 209, SIHBeAg = 77; and SIHBsAg > 200, SIHBeAg > 156, respectively. Additional studies in rats showed that compound A1 has favorable pharmacokinetic prosperities for further development purpose, with elimination half-time (t(1/2)) of 1.63 h and oral bioavailability (F) of 40.9%. (C) 2009 Elsevier Ltd. All rights reserved.
• Murata,T.; Miyamoto,M., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 1354 - 1361
  作者：Murata,T.、Miyamoto,M.

  DOI：——

  日期：——
• Crude Drugs from Aquatic Plants. I. On the Constituents of Alismatis Rhizoma. (1). Absolute Stereostructures of Alisols E 23-Acetate, F, and G, Three New Protostane-Type Triterpenes from Chinese Alismatis Rhizoma.
  作者：Masayuki YOSHIKAWA、Shoko HATAKEYAMA、Nobumitsu TANAKA、Youichi FUKUDA、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.41.1948

  日期：——

  From the less polar fraction of Chinese Alismatis Rhizoma [the dried rhizome of the aquatic plant Alisma orientale JUZEP. collected in Szechwan Province, China (Sentaku in Japanese)], three new protostane-type triterpenes named alisols E 23-acetate, F, and G were isolated together with four guaiane-type sesquiterpenes and several known triterpenes including 13, 17-epoxyalisol A. The absolute stereostructures of alisols E 23-acetate, F, and G have been determined on the basis of chemical and physicochemical evidence, which included the chemical correlations of alisols E 23-acetate, F, and G with the known triterpenes alisols A and A 24-acetate, and the application of the modified Mosher's method.

  从中国泽泻根茎（中国四川省采集的水生植物东方泽泻的干燥根茎（日文为 Sentaku））的极性较低的部分中，分离出了三种新的原烷型三萜类化合物，分别命名为泽泻醇 E 23-乙酸酯、F 和 G，以及四种愈创木型倍半萜类化合物和几种已知的三萜类化合物，包括 13，17-表紫苏醇 A。根据化学和物理化学证据，包括 E 23-乙酸烯醇、F 和 G 与已知三萜类烯醇 A 和 A 24-乙酸酯的化学相关性，以及应用改进的莫舍尔法，确定了 E 23-乙酸烯醇、F 和 G 的绝对立体结构。