26-thiodiosgenin 3-O-β-D-glucopyranoside | 1573154-39-8

• 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-thiodiosgenin 3-O-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6S,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-thiane]-16-yl]oxyoxane-3,4,5-triol
• CAS: 1573154-39-8
• 化学式: C₃₃H₅₂O₇S
• 分子量: 592.838
• InChiKey: VRZSCSACDDIWHJ-ZOODYHDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 26-thiodiosgenin 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F

  摘要：

  Both the sugar moieties and aglycons of steroid saponins play important roles for their bioactivities. In order to test the biological contribution of the glycosyl residue and search new saponins with notable anticancer activity, mono- and di-saccharide pseudodiosgenyl saponins 22-28 together with two pseudodiosgenyl conjugates 29 and 30 were conveniently synthesized, all of which were based on the aglycon 7 bearing the thio-ring F. The cytotoxicity on human cancer cells (MCF-7, HepG-2, A549) for all of the synthesized compounds 7 and 22-30 was evaluated by MTT method. The thio-aglycon 7 when conjugated with sugars exhibited potent cytotoxicity, and the introduction of D-glucosamine into aglycon 7 led to the most potent compound 28. Furthermore, DAPI staining, AV/PI staining, AO-relocation, AO-uptake and LysoTracker Red-uptake assays demonstrated that the cell death caused by neosaponin 28 was at least partially through apoptosis involving lysosomal membrane permeabilization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.055

文献信息

• Solasodine-3- O -β- d -glucopyranoside kills Candida albicans by disrupting the intracellular vacuole
  作者：Wenqiang Chang、Ying Li、Ming Zhang、Sha Zheng、Yan Li、Hongxiang Lou

  DOI：10.1016/j.fct.2017.05.045

  日期：2017.8

  The increasing incidence of fungal infections and emergence of drug resistance underlie the constant search for new antifungal agents and exploration of their modes of action. The present study aimed to investigate the antifungal mechanisms of solasodine-3-O-beta-D-glucopyranoside (SG) isolated from the medicinal plant Solanum nigrum L. In vitro, SG displayed potent fungicidal activity against both azole-sensitive and azole-resistant Candida albicans strains in Spider medium with its MICs of 32 mu g/ml Analysis of structure and bioactivity revealed that both the glucosyl residue and NH group were required for SG activity. Quantum dot (QD) assays demonstrated that the glucosyl moiety was critical for SG uptake into Candida cells, as further confirmed by glucose rescue experiments. Measurement of the fluorescence intensity of 2',7'-dichlorofluorescin diacetate (DCFHDA) by flow cytometry indicated that SG even at 64 mu g/ml just caused a moderate increase of reactive oxygen species (ROS) generation by 58% in C. albicans cells. Observation of vacuole staining by confocal microscopy demonstrated that SG alkalized the intracellular vacuole of C. albicans and caused hyper-permeability of the vacuole membrane, resulting in cell death. These results support the potential application of SG in fighting fungal infections and reveal a novel fungicidal mechanism. (C) 2017 Published by Elsevier Ltd.