螺茄-5-烯 | 14197-65-0

• 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
• 中文名称: 螺茄-5-烯
• 英文名称: (22R,25R)-spirosol-5-en-3β-yl O-β-D-glucopyranoside
• 英文别名: solasodine-3-O-β-D-glucopyranoside；solasodine β-D-glucopyranoside；SG；(22R,25R)-spirosol-5-en-3β-yl β-D-glucopyranoside；(22R,25R)-3β-β-D-glucopyranosyloxy-spirosol-5-ene；γ-Solamargin；Solasodine 3-glucoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,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'-piperidine]-16-yl]oxyoxane-3,4,5-triol
• CAS: 14197-65-0
• 化学式: C₃₃H₅₃NO₇
• 分子量: 575.786
• InChiKey: XMLLJGHZPHTUKK-GAMIEDRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  121
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  澳洲茄边碱 在 盐酸 作用下， 生成 螺茄-5-烯
  参考文献：
  名称：

  Briggs et al., Journal of the Chemical Society, 1952, p. 3587,3589

  摘要：

  DOI：

文献信息

• Antifungal Activity and Fungal Metabolism of Steroidal Glycosides of Easter Lily (<i>Lilium longiflorum</i>Thunb.) by the Plant Pathogenic Fungus,<i>Botrytis cinerea</i>
  作者：John P. Munafo、Thomas J. Gianfagna

  DOI：10.1021/jf200093q

  日期：2011.6.8

  biotransformation of the steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (6)

  灰葡萄孢。神父 是一种植物致病真菌，是复活节百合（Lilium longiflorum Thunb。）开花枯萎的病原体。复活节百合是类固醇糖苷的丰富来源，这些化合物可能在复活节百合的植物与病原体相互作用中发挥作用。从L. longiflorum中分离出5种甾体糖苷，包括2种甾体糖碱生物碱和3种呋喃甾醇皂苷，并使用体外平板测定法评估了对灰葡萄孢的真菌生长抑制活性。所有化合物均显示出抑制真菌生长的活性。然而，甾体糖生物碱（22 R，25 R）-spirosol-5-en-3β-yl中末端葡萄糖C-6'''的自然乙酰化ø -α-升-rhamnopyranosyl-（1→2） - [6- ö乙酰基β- d -glucopyranosyl-（1→4）] - β- d吡喃葡萄糖苷（2），通过抑制率提高的抗真菌活性灰质芽孢杆菌对化合物代谢的影响Apoptosis。糖基生物碱的乙酰化可能是病原体对解毒机制
• Kuhn; Loew, Chemische Berichte, 1955, vol. 88, p. 289,293, 294
  作者：Kuhn、Loew

  DOI：——

  日期：——
• 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.
• Bite; Rettegi, Acta Chimica Academiae Scientiarum Hungaricae, 1967, vol. 52, p. 79
  作者：Bite、Rettegi

  DOI：——

  日期：——
• GUSEVA; PASESHNICHENKO, Biokhimiya, 1959, vol. 24, # 3, p. 563 - 565
  作者：GUSEVA、PASESHNICHENKO

  DOI：——

  日期：——