五味子丙素 | 61301-33-5

• 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 - 苯丙烷和聚酮 - 单宁
• 中文名称: 五味子丙素
• 中文别名: 五味子素c
• 英文名称: schisandrinC
• 英文别名: 3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.02,10.04,8.017,21]docosa-1(22),2,4(8),9,15,17(21)-hexaene
• CAS: 61301-33-5
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.4
• InChiKey: HTBWBWWADZJXID-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123℃
• 沸点：
  549.2±50.0 °C(Predicted)
• 密度：
  1.232
• 溶解度：
  DMSO：8.33 mg/mL（21.67 mM；需要超声波）H2O：< 0.1 mg/mL（不溶）
• LogP：
  5.623 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Schisandrin C（Schizandrin-C）是从五味子中分离得到的一种植物化学木脂素。它表现出多种生物活性，包括抗癌、抗炎和抗氧化作用，并可用于癌症、阿尔茨海默病及肝病的研究。Schisandrin C 诱导细胞凋亡。

体外研究

在 U937 细胞中，施用 Schisandrin C（25-100 μM；48 小时）下调 Bcl-2、Bcl-xL 的表达，并伴随着 poly(ADP-ribose) polymerase (PARP) 的降解。Schisandrin C 还激活了 U937 细胞中的 caspase-3 和 -9。施用 Schisandrin C（25-100 μM；48 小时）以剂量依赖性方式诱导细胞凋亡，且 U937 细胞中基因组 DNA 的片段化也增加。施用 Schisandrin C（25-100 μM；72 小时）诱导 G1 期停滞。

• Western Blot 分析

  细胞系	U937 细胞
  浓度	25 μM, 50 μM, 100 μM
  孵化时间	48 小时
  结果	减少了凋亡相关蛋白的表达

• 细胞凋亡分析

  细胞系	U937 细胞
  浓度	25 μM, 50 μM, 100 μM
  孵化时间	48 小时
  结果	引起细胞凋亡

• 细胞周期分析

  细胞系	U937 细胞
  浓度	25 μM, 50 μM, 100 μM
  孵化时间	48 小时
  结果	引起 U937 细胞生长抑制和 G1 停滞

体内研究

在 Aβ1-42 诱导的阿尔茨海默病小鼠中，施用 Schisandrin C（侧脑室注射；i.c.v.；剂量 15-150 μg/kg；连续 5 天）减少了 Aβ1-42 引起的记忆障碍。治疗组中的海马神经元恢复到正常水平，并且较高剂量的 SCH-C（150 μg/kg）表现出轻微的神经保护作用，Aβ1-42 引起的阿米诺小鼠大脑中 SOD 和 GSHPx 活性恢复，GSH 的比例增加，ChEtotal 的水平降低。

• 动物模型

  动物模型	Aβ1-42 诱导的阿尔茨海默病小鼠
  剂量	15-150 μg/kg
  给药方式	侧脑室注射（i.c.v.）；15-150 μg/kg；连续 5 天
  结果	展现出强大的神经保护作用，与抗 ChEtotal 活性及抗氧化机制有关

化学性质

无色晶体，可溶于甲醇、乙醇、DMSO 等有机溶剂，来源于五味子。

用途

五味子丙素具有拮抗、抗癌、抗溃疡和保肝的作用。

文献信息

• Extracts with liver-X-receptor modulators, compounds and their use in weight control and treatment of disorders of lipid metabolism
  申请人：InterMed Discovery GmbH

  公开号：EP2025335A1

  公开（公告）日：2009-02-18

  The invention relates to the use, or methods (especially with regard to animals, especially human, that are in need of such treatment) comprising the use, of an extract and/or one or more natural compounds from plants or parts of plants, respectively, from a genus selected from the group consisting of Schisandra, Illicium, Kadsura, Steganotaenia and Magnolia, alone or as supplement, as active ingredient in the regulation of body weight and/or fat loss and/or for the management of obesity, either in humans or in animals, to the use of said extract and/or natural compound(s) or mixtures in the manufacture of a pharmaceutical or nutraceutical formulation for the regulation of body weight and/or fat loss and/or for the management of obesity either in humans or in animals. The above extract and/or compound(s) can further be used to reduce one or more adverse metabolic parameters in a subject, such as the blood cholesterol level, especially the "bad" low density lipid (LDL) cholesterol. The invention relates also to said extract and/or compound(s) for use in the treatment or in the preparation of a medicament for the treatment of obesity and/or elevated blood cholesterol, as well as their preparation. It also relates to pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s) which are useful in the regulation of body weight and/or fat loss and/or for the management of obesity.

  本发明涉及使用来自植物属Schisandra、Illicium、Kadsura、Steganotaenia和Magnolia的提取物和/或一种或多种天然化合物的用途或方法（特别是针对需要此类治疗的动物，尤其是人类），作为单独的活性成分或补充剂，在调节体重和/或减脂和/或管理肥胖方面的应用，无论是在人类还是动物中，以及在制造用于调节体重和/或减脂和/或管理肥胖的药物或营养保健品制剂中使用所述提取物和/或天然化合物或混合物。上述提取物和/或化合物还可以用于减少受试者的一个或多个不良代谢参数，例如血胆固醇水平，特别是“坏”的低密度脂蛋白（LDL）胆固醇。本发明还涉及所述提取物和/或化合物的用于肥胖和/或高血胆固醇治疗或制备药物的用途，以及它们的制备。还涉及包括所述提取物和/或天然化合物的药物或营养保健品制剂，其在调节体重和/或减脂和/或管理肥胖方面有用。
• USE OF FRUCTUS SCHISANDRAE AND EXTRACTS THEREOF IN PREVENTING AND DECREASING TOXIC AND SIDE EFFECTS OF ANTINEOPLASTIC DRUGS
  申请人：Hu Xun

  公开号：US20090022831A1

  公开（公告）日：2009-01-22

  Use of Fructus schisandrae in preparation of medicaments for preventing and reducing toxicity and side effects of antineoplastic agents. The toxicity and side effects of antineoplastic agents are cardiovascular toxicity, hepatotoxicity, nephrotoxicity, suppression of bone marrow, immunosuppression, or alopecia etc induced by antineoplastic agents. Fructus schisandrae and extracts thereof, especially ethanol extracts, schisandrin B, are effective in reducing antineoplastic agent's toxicity and side effects.
• EXTRACTS WITH LIVER-X-RECEPTOR MODULATORS, COMPOUNDS AND THEIR USE ESPECIALLY IN WEIGHT CONTROL
  申请人：Grothe Torsten

  公开号：US20110213026A1

  公开（公告）日：2011-09-01

  The invention relates to the use, or methods (especially with regard to animals, especially human, that are in need of such treatment) comprising the use, of an extract and/or one or more natural compounds from plants or parts of plants, respectively, from a genus selected from the group consisting of Schisandra, Illicium, Kadsura, Steganotaenia and Magnolia, alone or as supplement, as active ingredient in the regulation of body weight and/or fat loss and/or for the management of obesity, either in humans or in animals, to the use of said extract and/or natural compound(s) or mixtures in the manufacture of a pharmaceutical or nutraceutical formulation for the regulation of body weight and/or fat loss and/or for the management of obesity either in humans or in animals. The above extract and/or compound(s) can further be used to reduce one or more adverse metabolic parameters in a subject. The invention relates also to said extract and/or compound(s) for use in the treatment or in the preparation of a medicament for the treatment of obesity, as well as their preparation. It also relates to pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s) which are useful in the regulation of body weight and/or fat loss and/or for the management of obesity.
• EXTRACTS WITH LIVER-X-RECEPTOR MODULATORS, COMPOUNDS AND THEIR USE ESPECIALLY IN WEIGHT CONTROL
  申请人：INTERMED DISCOVERY GMBH

  公开号：US20130143959A1

  公开（公告）日：2013-06-06

  The invention relates to an extract and/or one or more natural compounds from plants or parts of plants, respectively, from a genus selected from Schisandra, Illicium, Kadsura, Steganotaenia or Magnolia, for the regulation of body weight, fat loss, and/or management of obesity, in humans or in animals, methods and uses of the same and to the use of the same or mixtures in the manufacture of a pharmaceutical or nutraceutical formulation. The above can further be used to reduce one or more adverse metabolic parameters in a subject. The invention relates also to said extract and/or compound(s) in the treatment or in the preparation of a medicament for treatment of obesity, as well as their preparation. It also relates to pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s), which are useful in the regulation of body weight and/or fat loss and/or for the management of obesity.
• US8404287B2
  申请人：——

  公开号：US8404287B2

  公开（公告）日：2013-03-26