盾叶新苷 | 91653-50-8

• 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
• 中文名称: 盾叶新苷
• 中文别名: 盾叶薯蓣皂苷I
• 英文名称: zingiberensis saponin I
• 英文别名: Zingiberensis saponin I；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-[(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'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 91653-50-8
• 化学式: C₅₁H₈₂O₂₂
• 分子量: 1047.2
• InChiKey: XJOTXMLDNWCDRH-HAUZKCKMSA-N

物化性质

• 熔点：
  285-287 °C(Solv: methanol (67-56-1))
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  335
• 氢给体数：
  12
• 氢受体数：
  22

安全信息

• 储存条件：
  2-8℃

制备方法与用途

生物活性方面，zingiberen newsaponin是从盾叶薯（Dioscorea zingiberensis）中分离得到的。研究显示，zingiberen newsaponin能够诱导血小板聚集。

反应信息

• 作为反应物：
  描述：

  盾叶新苷 在 steroidal saponin-β-glucosidase from Aspergillus flavus 作用下， 以 aq. buffer 为溶剂， 生成 薯蓣皂素
  参考文献：
  名称：

  Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin

  摘要：

  A new steroidal saponin-beta-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal beta-D-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-beta-glucosidase was 50 degrees C and pH 5.0. The steroidal saponin-beta-glucosidase was stable at 30-60 degrees C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a beta-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-beta-glucosidase and steroidal saponin-alpha-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.09.013
• 作为产物：
  描述：

  在 β-D-glucosidase 、 水 、 溶剂黄146 作用下， 以 aq. acetate buffer 为溶剂， 反应 13.0h， 以2.5 mg的产率得到盾叶新苷
  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

• Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin
  作者：Hongzhi Huang、Min Zhao、Li Lu、Dawei Tan、Wenbin Zhou、Chengqi Xiong、Yang Zhao、Xinbo Song、Liyan Yu、Baiping Ma

  DOI：10.1016/j.molcatb.2013.09.013

  日期：2013.12

  A new steroidal saponin-beta-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal beta-D-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-beta-glucosidase was 50 degrees C and pH 5.0. The steroidal saponin-beta-glucosidase was stable at 30-60 degrees C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a beta-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-beta-glucosidase and steroidal saponin-alpha-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study. (C) 2013 Elsevier B.V. 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。