26-O-β-D-glucopyranosyl-(25R)-furost-4-en-22α,26-diol-3,12-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 26-O-β-D-glucopyranosyl-(25R)-furost-4-en-22α,26-diol-3,12-dione
• 英文别名: terrestrinin D；(1R,2S,4S,6R,7S,8R,9S,12S,13R)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-ene-10,16-dione
• 化学式: C₃₃H₅₀O₁₀
• 分子量: 606.754
• InChiKey: GUGWHXWJEWIWJG-GMTLHWRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  26-O-β-D-glucopyranosyl-(25R)-furost-4-en-22α,26-diol-3,12-dione 在 水 、 三氟乙酸 作用下， 反应 4.0h， 生成 葡萄糖
  参考文献：
  名称：

  蒺藜甾体皂苷

  摘要：

  从蒺藜中分离出 16 种甾体皂苷，包括 7 种以前未报道的化合物。使用一维和二维核磁共振光谱、质谱和化学方法确定皂苷的结构。它们被鉴定为：26-O-β-d-吡喃葡萄糖基-(25R)-furost-4-en-2α,3β,22α,26-tetrol-12-one (terrestrinin C), 26-O-β-d -吡喃葡萄糖基-(25R)-furost-4-en-22α,26-diol-3,12-dione (terrestrinin D), 26-O-β-d-吡喃葡萄糖基-(25S)-furost-4-en-22α ,26-diol-3,6,12-trione (terrestrinin E), 26-O-β-d-glupyranosyl-(25R)-5α-furostan-3β,22α,26-triol-12-one (terrestrinin F) , 26-O-β-d-吡喃葡萄糖基

  DOI：

  10.1016/j.phytochem.2014.08.003

文献信息

• Selective glycosylation of steroidal saponins by Arthrobacter nitroguajacolicus
  作者：Jing-yuan Liu、Li Lu、Li-ping Kang、Yi-xun Liu、Yang Zhao、Cheng-qi Xiong、Yu-qin Zhang、Li-yan Yu、Bai-ping Ma

  DOI：10.1016/j.carres.2014.07.006

  日期：2015.1

  In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns. Sucrose was used as a non-activated sugar donor, and fifteen steroidal saponins were involved. Nine furostan saponins of the substrates were converted, and ten products were isolated and identified. Based on the HR-ESI-MS, 1D, and 2D NMR spectral data, one fructosyl was added to furostan saponins at C-6-OH of 26-O-beta-D-glucopyranosyl by A. nitroguajacolicus for all nine products. One product was distinguished by an additional fructosyl at the position of C-6-OH on the first added fructosyl. Spirostan saponins of the substrates could not be converted. Steroidal saponins embracing a fructosyl are quite rare according to other reports based on similar studies. This study successfully converted furostan saponins into new compounds. (C) 2014 Elsevier Ltd. All rights reserved.