timosaponin BIII | 142759-74-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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: timosaponin BIII
• 英文别名: timosaponin B；anemarsaponin B；Timosaponin B III；(2R,3R,4S,5S,6R)-2-[(2S)-4-[(1R,2S,4S,8S,9S,12S,13S,16S,18R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 142759-74-8
• 化学式: C₄₅H₇₄O₁₈
• 分子量: 903.072
• InChiKey: ROHLIYKWVMBBFX-XNZAAYBPSA-N

物化性质

• 沸点：
  1023.7±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  63
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  287
• 氢给体数：
  11
• 氢受体数：
  18

安全信息

• 储存条件：
  2-8℃

制备方法与用途

生物活性方面，timosaponin B III 是一种主要的甾体皂苷，它主要从知母中分离得到。该化合物具有显著的抗炎、抗血小板聚集以及抗抑郁作用。

反应信息

• 作为反应物：
  描述：

  timosaponin BIII 在 sodium hydrogenphosphate dodecahydrate 、 β-glucosidase 、 sodium hydroxide 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 以29.4%的产率得到timosaponin B-III-a
  参考文献：
  名称：

  Anti-depressive activities and biotransformation of timosaponin B-III and its derivatives

  摘要：

  Timosaponin B-III (TB-III) is a steroidal saponin isolated from the rhizome of Anemarrhenae asphodeloides (Liliaceae). The biotransformation of TB-III by β-glucosidase was investigated. Three biotransformation products were isolated and their structures were identified as timosaponin B-III-a (M1), (20R,25S)-5β-spirostane-3β-ol-3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galacopyanoside (M2) and timosaponin AIII (M3). Then the four compounds were evaluated for their anti-depressive activity in mice by the open field test, tail suspension test and forced swimming test. As a result, TB-III, M1 and M3 exhibited modest anti-depressive activity. Structure-activity relationships were investigated and the preliminary conclusions are summarised as follows: the glycosyl at C-3 and C-26 can increase the activity, the double bond between C-20 and C-22 might be important for the anti-depressive activity, the R-configuration at C-22 and S-configuration at C-20 are necessary for its anti-depressive activity.

  DOI：

  10.1080/14786419.2014.910663

文献信息

• New Saponins from Timosaponin BIII by Acid Hydrolysis
  作者：Zhiyu Liu、Weixin Jiang、Bin Wu、Chenggang Huang

  DOI：10.14233/ajchem.2013.13428

  日期：——

  Timosaponin BIII (TBIII), a saponin isolated from the rhizome of Anemarrhena asphodeloides, exhibited potent antidepressive and anxiolytic activities in depressed mice. After administration of TBIII in rats, two main metabolites had been detected in the brain tissue, which had similar aglycone with TBIII and formed by elimination of two hexose moieties. In this study, we had hydrolyzed TBIII by some means and obtained 4 artificial steroidal saponins (three novel steroidal saponins: timosaponin BIII-a, timosaponin BIII-b, timosaponin BIII-c; and a known steroidal saponin: timosaponin BII-b) by the dilute-acid hydrolysis. Their structures were verified by means of mass spectrometry and nuclear magnetic resonance (NMR) spectral analyses.

  知母皂苷BIII（TBIII）是从知母根茎中分离得到的一种皂苷，在抑郁小鼠中表现出强效的抗抑郁和抗焦虑活性。在大鼠中给予TBIII后，在脑组织中检测到两种主要代谢物，它们与TBIII具有相似的苷元结构，并通过消除两个六碳糖部分形成。在本研究中，我们通过稀酸水解方法对TBIII进行了水解，并获得了4种人工合成甾体皂苷（三种新型甾体皂苷：知母皂苷BIII-a、知母皂苷BIII-b、知母皂苷BIII-c；以及一种已知的甾体皂苷：知母皂苷BII-b）。它们的结构通过质谱和核磁共振（NMR）光谱分析得到验证。
• The structural elucidation of two new artificial steroidal saponins
  作者：Bin Wu、Zhi Yu Liu、Ming Song Fan、Zhao Lin Sun、Wei Xin Jiang、Cheng Gang Huang

  DOI：10.1016/j.cclet.2011.12.001

  日期：2012.3

  Two novel steroidal saponins (timosaponin BIII-a, timosaponin BIII-b) together with a known steroidal saponin (timosaponin BII-b) were prepared by the dilute acid hydrolysis of timosaponin BIII. Their structures were elucidated by means of 1D, 2D NMR and TOF-MS spectral analysis.

  两种新的甾体皂苷（timosaponin BIII-a，timosaponin BIII-b）与一种已知的甾体皂苷（timosaponin BII-b）是通过将timosaponin BIII进行稀酸水解而制备的。通过1D，2D NMR和TOF-MS光谱分析阐明了它们的结构。
• New transformation pathway and cytotoxic derivatives from the acid hydrolysis of timosaponin B III
  作者：Yun-Fang Zhao、Yu-Wei Zhang、Yinru Wang、Susan L. Morris-Natschke、Wei Liu、Ting-Ting Shang、Hong Yin、Kuo-Hsiung Lee、Xue-Feng Huang

  DOI：10.1080/14786419.2018.1499640

  日期：2019.10.2

  with better biological activity, timosaponin B III was structurally modified via acid hydrolysis to yield one new (2, timopregnane A I) C21 steroidal glycoside and seven known compounds. Their structures were elucidated on the basis of NMR spectroscopy and mass spectrometry. All eight compounds were evaluated for cytotoxic activity against MCF7, SW480, HepG2, and SGC7901 cell lines in vitro. As a result

  Timosaponin B III是一种主要的生物活性甾体皂苷，从知母阿米巴碱Bge中分离出来。为了潜在地发现具有更好生物活性的衍生物，通过酸水解对托莫司汀B III进行了结构修饰，以产生一种新的（2，替莫泼亚奈AI）C 21甾体糖苷和7种已知化合物。在NMR光谱和质谱的基础上阐明了它们的结构。所有八个化合物为对MCF7，SW480，HepG2细胞，和SGC7901细胞系的细胞毒活性进行评价体外。结果，化合物6和7表现出显着的活性（IC 502.94–12.2μM）。研究了这些化合物的构效关系，并提供了初步结论。此外，首次发现了动素皂苷B III的酸水解中的新的转化途径。
• Anti-depressive activities and biotransformation of timosaponin B-III and its derivatives
  作者：WeiXin Jiang、Jing Guo、Rui Xue、KaiCheng Zhu、ZhiXiong Li、MingCang Chen、ChengGang Huang

  DOI：10.1080/14786419.2014.910663

  日期：2014.9.17

  Timosaponin B-III (TB-III) is a steroidal saponin isolated from the rhizome of Anemarrhenae asphodeloides (Liliaceae). The biotransformation of TB-III by β-glucosidase was investigated. Three biotransformation products were isolated and their structures were identified as timosaponin B-III-a (M1), (20R,25S)-5β-spirostane-3β-ol-3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galacopyanoside (M2) and timosaponin AIII (M3). Then the four compounds were evaluated for their anti-depressive activity in mice by the open field test, tail suspension test and forced swimming test. As a result, TB-III, M1 and M3 exhibited modest anti-depressive activity. Structure-activity relationships were investigated and the preliminary conclusions are summarised as follows: the glycosyl at C-3 and C-26 can increase the activity, the double bond between C-20 and C-22 might be important for the anti-depressive activity, the R-configuration at C-22 and S-configuration at C-20 are necessary for its anti-depressive activity.