柴胡皂苷C | 20736-08-7

• 物质功能分类: 生物化工 - 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: 柴胡皂苷C
• 中文别名: 柴胡皂甙C；柴胡皂苷 C
• 英文名称: saikosaponin C
• 英文别名: SSc；beta-D-Glucopyranoside, (3beta,16beta)-13,28-epoxy-16-hydroxyolean-11-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->4)-O-[beta-D-glucopyranosyl-(1-->6)]-；(2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[[(1S,2S,4S,5R,8R,10S,13S,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 20736-08-7
• 化学式: C₄₈H₇₈O₁₇
• 分子量: 927.137
• InChiKey: VJEMOEYSQDKAQF-JDRYWMLESA-N

物化性质

• 熔点：
  310-314 °C(Solv: methanol (67-56-1))
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  65
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  17

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26
• WGK Germany：
  3

制备方法与用途

生物活性

Saikosaponin C 是柴胡中的活性成分，在阿尔滋海默症中主要靶作用于 amyloid beta 和 tau 蛋白。Saikosaponin C 抑制 Aβ1-40 和 Aβ1-42 的释放，抑制异常 tau 蛋白的磷酸化，但对 BACE1 的活性和表达无作用。

化学性质 

白色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于柴胡地上部分。

用途 

用于含量测定/鉴定/药理实验等。
药理药效:具有明显的催眠作用。

用途 

柴胡皂甙如柴胡皂苷C被用以帮助分析和解决中药材，如小柴胡汤的活性机理。

反应信息

• 作为反应物：
  描述：

  柴胡皂苷C 在 mouse intestinal flora 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以12 mg的产率得到saikogenin E
  参考文献：
  名称：

  New derivatives of saikosaponins.

  摘要：

  在对柴胡皂苷（柴胡的主要成分）的新陈代谢进行研究的过程中，在用酸和蜗牛酶进行培养后，分离出了五种新的化合物，它们分别来自柴胡皂苷a、c和d。在1 N硫酸-二氧六环溶液中，将柴胡皂苷a和c在60°C下培养，分离出了柴胡皂苷g和i，它们在C-9（11）、12处具有同环二烯部分，其结构被确定为3β，16β，23，28-四羟基齐墩果-9（11），12-二烯3-O-β-D-吡喃葡萄糖基（1→3）-β-D-吡喃岩藻糖苷和3β，16β，28-三羟基齐墩果-9（11），12-二烯3-O-β-D-吡喃葡萄糖基（1→6）-[α-L-吡喃鼠李糖基（1→4）] -β-D-吡喃葡萄糖苷。此外，在37°C下用蜗牛酶将柴胡皂苷b1、g和b2培养12小时后，形成了原柴胡皂�

  DOI：

  10.1248/cpb.33.3349

文献信息

• Determination of Saikosaponin Derivatives in <i>Radix </i><i>bupleuri</i> and in Pharmaceuticals of the Chinese Multiherb Remedy Xiaochaihu-tang Using Liquid Chromatographic Tandem Mass Spectrometry
  作者：Yuanwu Bao、Chuan Li、Hongwu Shen、Fajun Nan

  DOI：10.1021/ac0499423

  日期：2004.7.1

  Saikosaponins are bioactive oleanane saponins derived from the Chinese medicinal herb Radix bupleuri (“chaihu” in Chinese). An LC−MS/MS-based method has been developed for characterization and quantification of 15 saikosaponin derivatives (saikosaponin a, saikosaponin b1, saikosaponin g, saikogenin A, saikogenin H, saikosaponin c, saikosaponin h, saikosaponin i, prosaikogenin C2, prosaikogenin B2, saikogenin C, saikogenin B, saikosaponin d, saikosaponin b2, and saikogenin D) in one chromatographic run. Optimization of the ionization process was performed with electrospray and atmospheric pressure chemical ionization techniques in both positive and negative ion modes. Negative ion ESI was adopted for generation of the precursor deprotonated molecules to achieve the best ionization sensitivity for the analytes. In addition, the most abundant fragment ion was chosen for each analyte to give the best CID sensitivity. Because some of the saponin derivatives are isomeric, complete resolution for the whole analytes was achieved both chromatographically and mass spectroscopically. Furthermore, optimal internal standard was successfully discovered for determination of the analytes by making use of a combinatorial chemistry approach. Good linearity over the range ∼1.65 or 4.98 to 1200 ng/mL for the analytes was observed. The intraday accuracy and precision at nominal low, intermediate, and high concentration varied between 0.8 and 11.8% and between 80 and 116%, respectively, whereas those for interday assay were between 1.1 and 15.5% and between 86 and 119%, respectively. The lower limits of quantitation for the test compounds were ∼16.5 to 49.4 pg on-column. The new method offered higher sensitivity and greater specificity than previously reported LC methods. After the validation, the applicability of the method for determination of these chemicals present in a variety of crude chaihu roots and in different brands of the Chinese multiherb remedy Xiaochaihu-tang (or Shosaiko-to) extract granules has been demonstrated. The sensitivity and specificity of the technique will be the basis of a method for the accurate quantification of the saikosaponin derivatives in biomatrixes.

  柴胡皂苷是从中药材柴胡中提取的具有生物活性的齐墩果烷皂苷。开发了一种基于 LC−MS/MS 的方法，用于 15 种柴胡皂苷衍生物（柴胡皂苷 a、柴胡皂苷 b1、柴胡皂苷 g、柴胡皂苷元 A、柴胡皂苷元 H、柴胡皂苷 c、柴胡皂苷 h、柴胡皂苷 i、原柴胡皂苷元 C2、原柴胡皂苷元 B2）的表征和定量、柴胡皂苷元 C、柴胡皂苷元 B、柴胡皂苷元 d、柴胡皂苷元 b2 和柴胡皂苷元 D）在一次色谱运行中。使用电喷雾和大气压化学电离技术在正离子和负离子模式下对电离过程进行优化。采用负离子 ESI 生成前体去质子化分子，以实现分析物的最佳电离灵敏度。此外，为每种分析物选择最丰富的碎片离子，以提供最佳的 CID 灵敏度。由于一些皂苷衍生物是异构体，因此可以通过色谱和质谱实现整个分析物的完全分离。此外，通过利用组合化学方法成功地发现了用于测定分析物的最佳内标。分析物在 ~1.65 或 4.98 至 1200 ng/mL 范围内观察到良好的线性。标称低、中、高浓度的日内准确度和精密度分别在 0.8% 至 11.8% 和 80% 至 116% 之间变化，而日间测定的准确度和精密度分别在 1.1% 至 15.5% 和 86% 至 119% 之间。测试化合物的柱上定量下限为 ∼16.5 至 49.4 pg。与之前报道的 LC 方法相比，新方法具有更高的灵敏度和更高的特异性。经过验证，该方法适用于测定各种粗柴胡根和不同品牌的中草药小柴胡汤（或正斋子汤）提取颗粒中存在的这些化学物质。该技术的灵敏度和特异性将成为准确定量生物基质中柴胡皂苷衍生物的方法的基础。
• Triterpene compositions and methods for use thereof
  申请人：Research Development Foundation

  公开号：US20030039705A1

  公开（公告）日：2003-02-27

  The invention provides novel saponin mixtures and compounds which are isolated from the species Acacia victoriae and methods for their use. These compounds may contain a triterpene moiety, such as acacic or oleanolic acid, to which oligosaccharides and monoterpenoid moieties are attached. The mixtures and compounds have properties related to the regulation of apoptosis and cytotoxicity of cells and exhibit potent anti-tumor effects against a variety of tumor cells. The present application is a continuation-in-part of co-pending U.S. Patent Application Ser. No. 60/099,066, filed Sep. 3, 1998, and a continuation-in-part of U.S. patent application Ser. No. 60/085,997, filed May 19, 1998. The entire text of each of the above-referenced disclosures is specifically incorporated by reference herein without disclaimer.

  本发明提供了从维多利亚金合欢(Acacia victoriae)物种中分离出来的新型皂苷混合物和化合物，以及它们的使用方法。这些化合物可能包含三萜基团，如金合欢酸或齐墩果酸，附着有寡糖和单萜基团。这些混合物和化合物具有与细胞凋亡和细胞毒性调节相关的特性，并对多种肿瘤细胞表现出强效的抗肿瘤作用。本申请是待决美国专利申请号60/099,066的续篇，该专利申请于1998年9月3日提交，并且是待决美国专利申请号60/085,997的续篇，该专利申请于1998年5月19日提交。上述所有引用文件的全部内容都被明确地并入本文，不做免责声明。
• Seikosaponin derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0300474A2

  公开（公告）日：1989-01-25

  A phosphate ester of saikosaponin a, b₁, b₂, c, d or h or saikogenin A, C or D , or a pharmaceutically acceptable salt thereof, which exhibits potent antiinflammatory activity against adjuvant arthritis and then can be used safely as a drug for the treatment and prevention of rheumatism, and a process for preparing the same characterized by phosphorylating the saikosaponin or saikogenin.

  一种柴胡皂苷 Aref=https://www.molaid.com/MS_10177 target="_blank">皂苷 a、b₁、b₂、c、d 或 h 或柴胡皂苷 A、C 或 D 的磷酸酯或其药学上可接受的盐，该磷酸酯对辅助性关节炎具有强效抗炎活性，可安全地用作治疗和预防风湿病的药物，以及制备该磷酸酯的工艺，其特征在于将柴胡皂苷或柴胡皂苷磷酸化。
• EXTRACELLULAR MATRIX PRODUCTION PROMOTER
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0972508A1

  公开（公告）日：2000-01-19

  An agent which promotes the production of extracellular matrix; more particularly, acidic mucopolysaccharides such as hyaluronic acid and fibrous proteins such as collagen, and thus exhibits the effects of activating the extracellular matrix, normalizing skin tissue, and efficiently preventing skin aging by reinforcing the binding between the epidermis and the dermis. This agent contains as active ingredients the extracts of plants belonging to the genus Bupleurum such as B. falcatum Linne (Mishima Saiko), or saikosaponin and saikogenin contained in these extracts. Use of this agent as a skin preparation for external use, etc. makes it possible to promote the production of the above acidic mucosaccharides, fibrous proteins, etc. in fibroblasts, etc.

  一种促进细胞外基质生成的制剂，尤其是酸性粘多糖（如透明质酸）和纤维蛋白（如胶原蛋白），因此具有激活细胞外基质、使皮肤组织正常化以及通过加强表皮和真皮之间的结合有效防止皮肤老化的功效。本制剂的有效成分包括 Bupleurum（如 B. falcatum Linne（三岛茜草））属植物的提取物，或这些提取物中的 saikosaponin 和 saikogenin。将这种制剂用作外用皮肤制剂等，可促进成纤维细胞等产生上述酸性粘多糖、纤维蛋白等。
• Methods and compositions for treatment of COPD diseases
  申请人：Shanghai KE Pharmaceutical Co., LTD

  公开号：US10786521B2

  公开（公告）日：2020-09-29

  The present disclosure relates to treatment of a pulmonary disease. The methods and kits provided herein facilitate relieving the symptoms resulting from the pulmonary disease (e.g., asthma, chronic obstructive pulmonary disease (COPD), etc.).

  本公开涉及肺部疾病的治疗。本文提供的方法和试剂盒有助于缓解肺部疾病（如哮喘、慢性阻塞性肺病（COPD）等）引起的症状。