商陆皂甙乙;商陆皂苷乙;美商陆皂苷B | 60820-94-2

• 物质功能分类: 天然产物 - 萜类
• 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: 商陆皂甙乙;商陆皂苷乙;美商陆皂苷B
• 中文别名: 美商陆皂苷B；商陆皂甙B；商陆皂苷B；美商陆皂苷 B
• 英文名称: (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2 methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 英文别名: phytolaccagenin-3-O-β-D-xylopyranoside；3-O-β-D-xylopyranosyl-phytolaccagenin；3-O-β-D-xylopyranosylphytolaccagenin；phytolaccoside B；esculentoside B；3-O-β-D-xylopyranosyphytolaccagenin；(2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 60820-94-2
• 化学式: C₃₆H₅₆O₁₁
• 分子量: 664.834
• InChiKey: SFZVDNKTWPZIJG-ACNZYQHGSA-N

物化性质

• 沸点：
  779.3±60.0 °C(Predicted)
• 密度：
  1.33
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  商陆皂苷甲 在 β-d-glucosidase from snailase 、 calcium chloride 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 商陆皂甙乙;商陆皂苷乙;美商陆皂苷B
  参考文献：
  名称：

  Efficient enzymatic preparation of esculentoside B following condition optimization by response surface methodology

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2016.04.013

文献信息

• 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.