柴胡皂苷A | 20736-09-8

• 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A
• 中文别名: 柴胡皂甙A；柴胡皂苷 A
• 英文名称: saikosaponin A
• 英文别名: SSa；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 20736-09-8
• 化学式: C₄₂H₆₈O₁₃
• 分子量: 780.994
• InChiKey: KYWSCMDFVARMPN-MSSMMRRTSA-N

物化性质

• 熔点：
  225～232℃ (dec.)
• 沸点：
  893.7±65.0 °C(Predicted)
• 密度：
  1.163～1.168 g/ml
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、超声处理）、吡啶（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  208
• 氢给体数：
  8
• 氢受体数：
  13

安全信息

• 海关编码：
  29389090
• 安全说明：
  S26
• WGK Germany：
  3

制备方法与用途

生物活性

Saikosaponin A 是从银柴胡中提取的主要活性成分，能够上调 LXRα 的表达，并展现出有效的抗炎活性。

化学性质

Saikosaponin A 为淡黄色结晶状物质，易溶于水和稀醇，难溶于苯、乙醚及氯仿。它来源于柴胡的地上部分。

用途

柴胡皂苷A具有镇静、抗病毒、免疫调节、保护肝脏和肾脏以及抗癌的作用。此外，它还用于含量测定、鉴定及药理实验等。其药理作用还包括抗惊厥、抗癫痫及抑制细胞粘附等多种功能。

反应信息

• 作为反应物：
  描述：

  柴胡皂苷A 在 Paenibacillus mucilaginosus KCTC 3870^T BglPm 作用下， 反应 8.0h， 生成 saikogenin F
  参考文献：
  名称：

  柴胡皂甙重组酶解法生产Prosaikogenin F、Prosaikogenin G、Saikogenin F和Saikogenin G及其抗癌作用

  摘要：

  柴胡皂甙、柴胡皂甙是负责其药理和生物活性的主要成分。然而，由于其在植物中的稀有性，作为糖苷水解的柴胡皂苷的原柴胡皂苷元和柴胡皂苷元的抗癌作用仍然未知。在这项研究中，我们应用了两种重组糖苷水解酶，它们表现出与柴胡皂苷的糖苷切割活性。BglPm 和 BglLk 这两种酶是从粘液类芽孢杆菌和朝鲜乳杆菌中克隆的，在 30-37 °C 和 pH 6.5-7.0 之间表现出良好的活性。柴胡皂甙 A 和 D 是从粗制的B. falcatum中纯化得到的L.提取物采用制备型高效液相色谱技术。通过具有高β-糖苷酶活性的酶转化，Saikosaponin A 和 D 通过 prosaikogenin F 转化为saikogenin F，并通过 prosaikogenin G 转化为saikogenin G。使用硅胶柱纯化两种saikogenin和两种prosaikogenin化合物，分别获得78.1、62.4、8

  DOI：

  10.3390/molecules27103255
• 作为产物：
  描述：

  2"-O-acetylsaikosaponin a 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以22 mg的产率得到柴胡皂苷A
  参考文献：
  名称：

  Chemical evaluation of Bupleurum species collected in Yunnan, China.

  摘要：

  皂苷是从 Bupleurum marginatum (Zhuye-Chaihu)、B. marginatum var. 的根中分离出来的。 stenophyllum (Zezhuye-Chaihu) 和 B. rockii (丽江-柴胡) 在中国云南采集并鉴定。为了评价这些植物作为药物的效果，还对植物中的药理活性皂苷、柴胡皂苷-a (1)和-d (3)进行了定量分析，并与镰刀花和中国柴胡进行比较。

  DOI：

  10.1248/cpb.34.1158

文献信息

• MRGX Receptor Antagonists
  申请人：Rheinische-Friedrich-Wilhelms-Universität Bonn

  公开号：US20210128561A1

  公开（公告）日：2021-05-06

  The invention relates to a method for preventing or treating a disease or disorder that is associated with the MrgX2 receptor. The invention also relates to MrgX2 antagonists and physiologically acceptable salts thereof. The invention also relates to pharmaceutical compositions and dosage forms comprising an MrgX2 antagonist.

  该发明涉及一种用于预防或治疗与MrgX2受体相关的疾病或紊乱的方法。该发明还涉及MrgX2拮抗剂及其生理上可接受的盐。该发明还涉及包含MrgX2拮抗剂的药物组合物和剂型。
• 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。
• [EN] THERAPEUTIC COMBINATION OF GALNAC-OLIGONUCLEOTIDE CONJUGATE AND SAPONIN, AND USES THEREOF<br/>[FR] COMBINAISON THÉRAPEUTIQUE DE CONJUGUÉ GALNAC-OLIGONUCLÉOTIDE ET DE SAPONINE, ET SES UTILISATIONS
  申请人：SAPREME TECH BV

  公开号：WO2021261998A1

  公开（公告）日：2021-12-30

  The invention relates to a pharmaceutical combination comprising: a conjugate of an effector molecule and a ligand for ASGPR, wherein the ligand for ASGPR comprises at least one GalNAc moiety; and a saponin of the monodesmosidic or bidesmosidic triterpene glycoside type. The invention also relates to a pharmaceutical composition comprising the conjugate and the saponin. In addition, the invention relates to a pharmaceutical combination or composition of the invention, for use as a medicament, or for use in the treatment or prophylaxis of a disease or health problem in which an expression product is involved of any one or more of genes: apoB, TTR, PCSK9, ALAS1, ATS, GO, CCS, X gene of HBV, S gene of HBV, AAT and LDH, and/or for use in the treatment or prophylaxis of a cancer, an infectious disease, a viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, AAT related liver disease, acute hepatic porphyria, TTR-mediated amyloidosis, hereditary TTR amyloidosis (hATTR), complement-mediated disease, hepatitis B infection, or an auto-immune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring an effector molecule of the invention from outside a cell to inside said cell, preferably into the cytosol of said cell. The invention also relates to an in vitro or ex vivo method for transferring the conjugate of the invention from outside a cell to inside said cell.

  本发明涉及一种制药组合物，包括：一种效应分子和ASGPR配体的结合物，其中，ASGPR配体包括至少一个GalNAc基团；以及一种单脱单糖或双脱单糖三萜糖苷类皂苷。本发明还涉及一种包括该结合物和该皂苷的制药组合物。此外，本发明还涉及该制药组合物或制药组合物的用途，用于作为药物，或用于治疗或预防涉及以下一个或多个基因的疾病或健康问题的表达产物：apoB，TTR，PCSK9，ALAS1，ATS，GO，CCS，HBV的X基因，HBV的S基因，AAT和LDH；或用于治疗或预防癌症、传染病、病毒感染、高胆固醇血症、原发性高草酸尿症、血友病A、血友病B、AAT相关肝病、急性肝性卟啉病、TTR介导的淀粉样变性、遗传性TTR淀粉样变性（hATTR）、补体介导的疾病、乙型肝炎感染或自身免疫性疾病。此外，本发明还涉及一种从细胞外向细胞内转移本发明的效应分子的体外或体内方法，优选地进入该细胞的细胞质。本发明还涉及一种从细胞外向细胞内转移本发明的结合物的体外或体内方法。
• New derivatives of saikosaponins.
  作者：KOJI SHIMIZU、SAKAE AMAGAYA、YUKIO OGIHARA

  DOI：10.1248/cpb.33.3349

  日期：——

  In the course of studies on the metabolism of saikosaponins, which are the main constituents of Bupleurum falcatum L., five new compounds derived from saikosaponins a, c and d were isolated after incubation with acid and snail enzyme. On incubation of saikosaponins a and c at 60°C in a 1 N sulfuric acid-dioxane solution, saikosaponins g and i possessing a homoannular diene moiety at C-9 (11), 12 were isolated, and their structures were elucidated as 3β, 16β, 23, 28-tetrahydroxyoleana-9 (11), 12-diene 3-O-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside and 3β, 16β, 28-trihydroxyoleana-9 (11), 12-diene 3-O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside, respectively. Furthermore, on incubation of saikosaponins b1, g and b2 with snail enzyme for 12h at 37°C, prosaikogenins A, H, and D were formed ; they were identified as the 3-β-D-fucopyranosides of saikogenins A, H and D.

  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�
• 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。