dioscin

• 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: dioscin
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-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'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₅H₇₂O₁₆
• 分子量: 869.057
• InChiKey: VNONINPVFQTJOC-JSOTTYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  61
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  236
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  dioscin 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 L-rhamnopyranose 、 D-古洛糖 、 diosgenin
  参考文献：
  名称：

  Steroidal saponins from Smilax excelsa rhizomes

  摘要：

  From the n-butanol soluble fraction of the methanol extract of the rhizomes of Smilax excelsa, three new furostanol saponins 3-O-[4-O-acetyl--L-rhamnopyranosyl-(1 2)-{-L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (1), 3-O-[2-O-acetyl--L-rhamnopyranosyl-(1 2)-{-L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (2), 3-O-[3-O-acetyl--L-rhamnopyranosyl-(1 2)-{-L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (3), and three known saponins: protodioscin (4), pseudoprotodioscin (5) and dioscin (6) were isolated.

  DOI：

  10.1080/14786410802624827

文献信息

• Steroids from herbs of <i>Reineckia carnea</i> and their anticomplement activities
  作者：Xu Xu、Bei Wu、Yanzhi Zhan、Wenping Huang、Shilin Yang、Quan Wen、Yulin Feng

  DOI：10.1080/14786419.2017.1423309

  日期：2019.6.3

  A new polyhydroxylated pregnane, named l beta,2 beta,3 beta,4 beta,5 beta,6 beta-hexolhydroxy-pregn-16-en-20-one (1), along with nine known (2-10) steroidal saponins were isolated from the whole plant of Reineckia carnea. Structure elucidations of all compounds were established by interpretation of their NMR spectral data, HR-ESI-MS and comparing with literatures. In addition, these compounds were evaluated with anticomplement activity. The result showed that compound 1 exhibited anticomplement effects with the CH50 values of 0.043 mg/mL, but saponins (2-10) showed no inhibition. Interestingly, hydrolysis of steroidal saponins (2-10) resulted in its aglycones (2a-10a) correspondingly which showed anticomplement activity with the CH50 values of 0.049-0.156 mg/mL.[GRAPHICS].
• Steroidal saponins from <i>Smilax excelsa</i> rhizomes
  作者：Antoaneta Ivanova、Bozhanka Mikhova、Iris Klaiber、Dragomir Dinchev、Ivanka Kostova

  DOI：10.1080/14786410802624827

  日期：2009.7.10

  From the n-butanol soluble fraction of the methanol extract of the rhizomes of Smilax excelsa, three new furostanol saponins 3-O-[4-O-acetyl--L-rhamnopyranosyl-(1 2)--L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (1), 3-O-[2-O-acetyl--L-rhamnopyranosyl-(1 2)--L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (2), 3-O-[3-O-acetyl--L-rhamnopyranosyl-(1 2)--L-rhamnopyranosyl-(1 4)}--D-glucopyranosyl]-26-O-[-D-glucopyranosyl]-22-hydroxy-(25R)-furost-5-ene-3,26-diol (3), and three known saponins: protodioscin (4), pseudoprotodioscin (5) and dioscin (6) were isolated.