商陆皂苷甲 | 65497-07-6

• 物质功能分类: 生物化工 - 天然产物
• 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: 商陆皂苷甲
• 中文别名: 商陆皂苷A；商陆皂甙；商陆皂甙A；商陆皂甙 A
• 英文名称: esculentoside A
• 英文别名: phytolaccoside E；3-O-[β-D-glucopyranosyl-(1,4)-β-D-xylo-pyranosyl]phytolaccagenin；Olean-12-ene-28,29-dioic acid,3-[(4-O-b-D-glucopyranosyl-b-D-xylopyranosyl)oxy]-2,23-dihydroxy-,29-methyl ester, (2b,3b,4a,20b)-；(2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 65497-07-6
• 化学式: C₄₂H₆₆O₁₆
• 分子量: 826.976
• InChiKey: ZMXKPCHQLHYTHY-OWRBLJEPSA-N

物化性质

• 熔点：
  >192°C (dec.)
• 沸点：
  936.7±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  58
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  262
• 氢给体数：
  9
• 氢受体数：
  16

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29389090
• WGK Germany：
  3

制备方法与用途

作用

商陆皂苷活性成分具备多种药理作用，包括抗炎、免疫增强及抗肿瘤。其中，以商陆皂苷甲的含量最高。

应用

商陆皂苷甲在各种急性或慢性模型中展现出显著的抗炎和抗凋亡效果，并能够抑制肿瘤细胞增殖。该成分可通过抑制炎性因子产生来缓解LPS诱导的急性肺损伤，减少LPS引起的NO释放。此外，作为Nrf2激活剂，商陆皂苷甲还能抑制氧化应激，从而减轻过敏性气道炎症，使其成为潜在的抗氧化剂。

生物活性

Esculentoside A（EsA），是从商陆Phytolacca esculenta根部中分离出的一种三萜皂苷。EsA具有抗炎作用，并对环氧合酶-2 (COX-2) 选择性抑制。此外，它通过抑制NF-ΚB和丝裂原活化蛋白激酶 (MAPK) 信号通路来减少LPS诱导的急性肺损伤中的炎症反应。

体外研究

Escarutidoside A（EsA）在浓度为0-10 μM时能降低激活的巨噬细胞中TNF的释放量，持续时间为24小时。

体内研究

Escarutidoside A（EsA）通过腹腔注射给予小鼠（剂量分别为5、10和20 mg/kg；每日一次；连续7天），可显著减少小鼠血清中的TNF、IL-1和IL-6水平。具体实验结果如下：

• 动物模型：BXSB小鼠
• 剂量：20 mg/kg
• 给药方式：腹腔注射（20 mg/kg；每日一次；4周）
• 结果：缓解了LN引起的肾损伤。

化学性质

商陆皂苷甲为白色结晶粉末，易溶于水、热甲醇和乙醇及正丁醇，难溶于丙酮和乙醚等亲脂性溶剂。它来源于商陆Phytolacca acinosa Roxb。

用途

• 商陆皂苷甲具有抗炎、免疫增强以及抗肿瘤作用。
• 可用于含量测定/鉴定/药理实验等。

反应信息

• 作为反应物：
  描述：

  商陆皂苷甲 在 盐酸 、 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 methyl (2β,3β)-28-{[3-(benzylamino)propyl]amino}-2,3,23-trihydroxy-28-oxoolean-12-en-30-oate
  参考文献：
  名称：

  七叶树苷 A 及其苷元 Phytolaccagenin 新衍生物的合成及其溶血活性评价和脂多糖诱导的一氧化氮产生的抑制作用

  摘要：

  合成并表征了一系列 46 种源自七叶树苷 A 及其苷元的化合物。评估了这些化合物对脂多糖 (LPS) 诱导的 NO 产生、溶血活性和细胞活力的影响。通过比较七叶苷A的衍生物与其苷元衍生物，建立了结构活性关系。与七叶苷 A 及其衍生物相比，苷元及其衍生物对 LPS 诱导的 NO 产生具有更高的抑制作用，并且溶血活性更低。

  DOI：

  10.1002/cbdv.201000339

文献信息

• Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A
  作者：Fei Wu、Yanghua Yi、Peng Sun、Dazhi Zhang

  DOI：10.1016/j.bmcl.2007.10.006

  日期：2007.12

  Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound 23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA. (c) 2007 Elsevier Ltd. All rights reserved.
• New approaches to the structural modification of olean-type pentacylic triterpenes via microbial oxidation and glycosylation
  作者：Yu-Yao Zhu、Li-Wu Qian、Jian Zhang、Ji-Hua Liu、Bo-Yang Yu

  DOI：10.1016/j.tet.2011.04.055

  日期：2011.6

  Microbial transformation of 4 olean-type pentacyclic triterpenes (OPTs), 3-oxo oleanolic acid (1), 3-acetyl oleanolic acid (2), oleanolic acid (3), and esculentoside A (4) was studied. After the screening of 12 strains of microbes, preparative biotransformation by two strains of Streptomyces griseus ATCC 13273 and Aspergillus ochraceus CICC 40330 resulted in the isolation of 10 metabolites. The microbial catalyzed high efficient regio-selective methyl oxidation and glycosylation were discovered, which could be provided as an alternative method to expand the structural diversity of OPTs. All the structures of the metabolites were elucidated unambiguously by ESI-MS, H-1 NMR, C-13 NMR, and 2D-NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.
• Efficient enzymatic preparation of esculentoside B following condition optimization by response surface methodology
  作者：Pan Cui、Tong-Yi Dou、Yan-Ping Sun、Shi-Yang Li、Lei Feng、Li-Wei Zou、Ping Wang、Da-Cheng Hao、Guang-Bo Ge、Ling Yang

  DOI：10.1016/j.molcatb.2016.04.013

  日期：2016.8

  Esculentoside B (EsB, also named phytolaccagenin 3-O-beta-D-xylopyranoside), a pentacyclic triterpene isolated from herbal medicine Radix phytolaccae, has been found to possess multiple pharmacological activities. Nonetheless, the low content in nature and the difficulties in the total synthesis of EsB strongly limit its extensive investigations and further development as a drug candidate. This study aims to provide a practical method for highly efficient preparation of EsB using esculentoside A (EsA, phytolaccagenin 3-beta-D-glucopyranosyl (1 -> 4)-beta-D-xylopyranoside) as the starting material. beta-D-glucosidase from snailase was used to catalyze the formation of EsB, and the product was then purified and fully characterized by both HRMS and NMR. To prepare EsB in a more cost-effective way, response surface methodology (RSM) was used to explore the potential effects of the reaction conditions (such as reaction temperature, pH, enzyme load, and reaction time) on the conversion rates of EsA. The highest EsB yield of 0.66 mg/ml was obtained experimentally under optimized conditions as follows: temperature 48.28 degrees C, pH 6.4, enzyme load 4.43%, and reaction time 2.73 h. This result agreed well with the predicted yield of 0.68 mg/ml by RSM. The enzymatic kinetics of this biotransformation was characterized at the optimum pH and temperature. The S-50 value was evaluated as 167.4 mu M, while the Vmax value was 345.6 nmol/min/mg. In summary, this study provided a mild and practical method for the highly efficient preparation of EsB from EsA, which held great promise for large scale production of EsB. (C) 2016 Elsevier B.V. All rights reserved.
• Synthesis of Novel Derivatives of Esculentoside A and Its Aglycone Phytolaccagenin, and Evaluation of Their Haemolytic Activity and Inhibition of Lipopolysaccharide-Induced Nitric Oxide Production
  作者：Wei Gong、Zhihui Jiang、Peng Sun、Ling Li、Yongsheng Jin、Lucheng Shao、Wen Zhang、Baoshu Liu、Hongwei Zhang、Hua Tang、Yufeng Chen、Yanghua Yi、Dazhi Zhang

  DOI：10.1002/cbdv.201000339

  日期：2011.10

  compounds derived from esculentoside A and its aglycone were synthesized and characterized. The effect of these compounds on lipopolysaccharide (LPS)‐induced NO production, haemolytic activity, and cell viability was evaluated. Structureactivity relationship was established by comparing the derivatives of esculentoside A with its aglycone derivatives. Both the aglycone and its derivatives showed higher inhibitory

  合成并表征了一系列 46 种源自七叶树苷 A 及其苷元的化合物。评估了这些化合物对脂多糖 (LPS) 诱导的 NO 产生、溶血活性和细胞活力的影响。通过比较七叶苷A的衍生物与其苷元衍生物，建立了结构活性关系。与七叶苷 A 及其衍生物相比，苷元及其衍生物对 LPS 诱导的 NO 产生具有更高的抑制作用，并且溶血活性更低。