(25R)-26-O-(β-D-glucopyranosyl)-furost-5-en-3β,22α,26-triol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside | 1240293-61-1

• 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: (25R)-26-O-(β-D-glucopyranosyl)-furost-5-en-3β,22α,26-triol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (25R)-furost-5-en-3β,22α,26-triol 26-O-β-D-glucopyranosyl-3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside；(25R)-26-O-(β-D-glucopyranosyl)-furost-5-en-3β,22R,26-triol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside；protogracillin；protodeltonin；deltoside；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,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-18-en-16-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1240293-61-1
• 化学式: C₅₁H₈₄O₂₃
• 分子量: 1065.21
• InChiKey: RPYHJEFMMXMMHG-AATSBFCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  74
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  366
• 氢给体数：
  14
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  (25R)-26-O-(β-D-glucopyranosyl)-furost-5-en-3β,22α,26-triol 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 在 β-D-glucosidase 、 水 、 溶剂黄146 作用下， 以 aq. acetate buffer 为溶剂， 反应 13.0h， 以2.2 mg的产率得到三角叶薯蓣皂苷
  参考文献：
  名称：

  燕麦地上部分的甾体糖苷及其细胞毒活性

  摘要：

  十二甾体糖苷（1 - 12）获自的地上部分分离燕麦L.（禾本科）。分离出的化合物中，有1种为首次从植物中直接分离得到，2～6种为新的甾体苷。的结构1 - 6被他们的光谱数据，化学转化，以及水解产物的色谱和光谱分析的分析来确定。化合物5和6是具有B环收缩骨架的新型甾体糖苷（B-nor steroid）。化合物1 , 9 ,图11和12对HL-60人早幼粒细胞白血病细胞、MIA PaCa-2人胰腺癌细胞和A549人肺腺癌细胞具有细胞毒性，IC 50值范围为0.79至13.5μM。用1处理的 HL-60 细胞表现出凋亡特征，即核染色质凝聚、亚 G1 细胞的积累和 caspase-3 的激活。此外，在1处理的 HL-60 细胞中，线粒体膜电位的丧失和细胞色素c释放到细胞质中表明1通过线粒体依赖性细胞凋亡途径诱导细胞凋亡。

  DOI：

  10.1021/acs.jafc.1c05782

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.
• Steroidal Glycosides from the Aerial Parts of <i>Avena sativa</i> L. and Their Cytotoxic Activity
  作者：Akihito Yokosuka、Keita Ishihara、Tsuyoshi Yamada、Tomoki Iguchi、Yoshihiro Mimaki

  DOI：10.1021/acs.jafc.1c05782

  日期：2021.12.8

  Twelve steroidal glycosides (1–12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2–6 were new steroidal glycosides. The structures of 1–6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products

  十二甾体糖苷（1 - 12）获自的地上部分分离燕麦L.（禾本科）。分离出的化合物中，有1种为首次从植物中直接分离得到，2～6种为新的甾体苷。的结构1 - 6被他们的光谱数据，化学转化，以及水解产物的色谱和光谱分析的分析来确定。化合物5和6是具有B环收缩骨架的新型甾体糖苷（B-nor steroid）。化合物1 , 9 ,图11和12对HL-60人早幼粒细胞白血病细胞、MIA PaCa-2人胰腺癌细胞和A549人肺腺癌细胞具有细胞毒性，IC 50值范围为0.79至13.5μM。用1处理的 HL-60 细胞表现出凋亡特征，即核染色质凝聚、亚 G1 细胞的积累和 caspase-3 的激活。此外，在1处理的 HL-60 细胞中，线粒体膜电位的丧失和细胞色素c释放到细胞质中表明1通过线粒体依赖性细胞凋亡途径诱导细胞凋亡。