Saikogenin A | 5092-09-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: Saikogenin A
• 英文别名: (3S,4R,4aR,6aR,6bS,8S,8aS,14aR,14bS)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicene-3,8-diol
• CAS: 5092-09-1
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: QGNVMEXLLPGQEV-HSFRRAFJSA-N

物化性质

• 熔点：
  287-293 °C
• 沸点：
  607.4±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

制备方法与用途

生物活性

Saikogenin A 可从中药柴胡中提取，是一种二肽基肽酶 IV (DPP-IV) 抑制剂。

靶点

DPP-IV

体外研究

Saikogenin A 对 DPP-IV 具有一定的抑制作用。在浓度为 20 μg/mL 的条件下，其对 DPP-IV 的抑制率为 47.6%。DPP-IV 是一种非经典丝氨酸氨基肽酶，它从多肽和蛋白质的氨基末端（N-末端）去除 Xaa-Pro 氨基二肽。

体内研究

Saikogenin A 是一种抗炎药物，存在于名为川芎的中药植物中提取物。与正常大鼠相比，在去肾上腺大鼠中 Saikogenin A 减轻卡拉胶诱导水肿的效果较差。其抗炎作用主要归因于皮质醇释放增多所致的促肾上腺皮质激素（ACTH）分泌增加以及直接对炎症过程的影响。

反应信息

• 作为反应物：
  描述：

  Saikogenin A 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 3β,16β,23,28-tetrahydroxyolean-13(18)-ene
  参考文献：
  名称：

  The Chemical Studies on Oriental Plant Drugs. XV. On the Constituents of Bupleurum Spp. (2). The Structure of Saikogenin A, a Sapogenin of Bupleurum falcatum L.

  摘要：

  一种被提议命名为赛可根素A的皂苷元，已从柴胡（Bupleurum falcatum L，业名：Mishimasaiko）的皂苷中获得。本研究为赛可根素A提供了结构式（I）。

  DOI：

  10.1248/cpb.14.1023
• 作为产物：
  描述：

  柴胡皂苷B1 生成 Saikogenin A
  参考文献：
  名称：

  Triterpenoid saponins from Bupleurum smithii var. parvifolium

  摘要：

  Four triterpenoidal saponins, prosaikogenin A and saikosaponins b(1), n and o, were isolated from the roots of the title plant for the first time. Saikosaponin O is a new compound, which was identified as 3 beta,16 beta,23,28-tetrahydroxyolean-11,13(18)-diene-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranoside.

  DOI：

  10.1016/0031-9422(96)00026-x

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。
• 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�
• Isolation of Saponins with the Inhibitory Effect on Nitric Oxide, Prostaglandin E2 and Tumor Necrosis Factor-.ALPHA. Production from Pleurospermum kamtschaticum
  作者：Hyun-Ju Jung、Sei-Gun Kim、Jung-Hwan Nam、Kwang-Kyun Park、Won-Yun Chung、Won-Bae Kim、Kyung-Tae Lee、Jong-Heon Won、Jong-Won Choi、Hee-Juhn Park

  DOI：10.1248/bpb.28.1668

  日期：——

  As an attempt to search for bioactive natural products exerting antiinflammatory activity, we have isolated two saponins were isolated from the aerial portion of Pleurospermum kamtschaticum (Umbelliferae) by nitrite assay activity-directed chromatographic fractionation. They were identified as saikogenin F 3-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranoside} (buddlejasaponin IV, 1) and 3β,16β,23,28-tetrahydroxy-11α-methoxyolean-12-ene 3-O-β-D-glucopyranosyl(1→2)-[β-D-glucopyranosyl(1→3)]-β-D-fucopyranoside} (buddlejasaponin IVa, 2). Compound 1 significantly inhibited nitric oxide (NO) production, and it also significantly decreased prostaglandin E2 (PGE2) and tumor necrosis factor-α (TNF-α) release in the lipopolysaccharide (LPS)-activated macrophage Raw 264.7 cells whereas compound 2 was much less active. Saikogenin A (3) and –H (4) were obtained by hydrolyzing 1 and 2. Although these sapogenin showed strong NO inhibition, these effects were caused by the cytotoxic effect on Raw 264.7 cells. These results supported the notion that buddlejasaponin IV is a major inhibitors of NO, PGE2 and TNF-α production in P. kamtschaticum.

  为了寻找具有抗炎活性的生物活性天然产物，我们通过亚硝酸盐测定活性色谱分离法从坎氏海葱（伞形科）的地上部分中分离出两种皂苷。它们被鉴定为西克皂苷F 3-O-β-D-吡喃葡萄糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→3)]-β-D-吡喃岩藻糖苷}（西克皂苷IV，1）和3β,16β,23,28-四羟基-11α-甲氧基齐墩果-12-烯 3-O-β-D-吡喃葡萄糖基(1→2)-[β-D-吡喃葡萄糖基(1→3)]-β-D-吡喃岩藻糖苷}（西克皂苷IVa，2）。化合物1可显著抑制一氧化氮（NO）的产生，还能显著降低脂多糖（LPS）激活的巨噬细胞Raw 264.7细胞中前列腺素E2（PGE2）
• 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 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。