Uttronin B | 116481-33-5

• 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: Uttronin B
• 英文别名: diosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-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-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 116481-33-5
• 化学式: C₃₉H₆₂O₁₂
• 分子量: 722.914
• InChiKey: ZAAOTIMLOADUSG-CMZWBXEQSA-N

物化性质

• 沸点：
  838.8±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  51
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Uttronin B 生成 薯蓣皂素
  参考文献：
  名称：

  Anti-allergic substances from the rhizomes of Dioscorea membranacea

  摘要：

  Extracts of five species of Thai medicinal plants, locally known as Hua-Khao-Yen, were screened for anti-allergic activities using RBL-2H3 cells. Of the five species studied, the ethanolic extract of Dioscorea membranacea exhibited potent inhibitory activity against beta-hexosaminidase release as a marker of degranulation in RBL-2H3 cells, with an IC50 value of 37.5 mu g/mL. Eight compounds were isolated from this crude ethanolic extract, [two naphthofuranoxepins (1, 2), one phenanthraquinone (3), three steroids (4-6), and two steroidal saponins (7,8)], and tested for their anti-allergic activities. The results showed that dioscorealide B (2) possessed the highest activity with an IC50 value of 5.7 mu M, followed by dioscoreanone (3, IC50 = 7.7 mu M), dioscorealide A (1, IC50 = 27.9 mu M), and. diosgenin (9, IC50 = 29.9 mu M). Structure-activity relationship studies of naphthofuranoxepins on anti-allergic activity revealed that the hydroxylation at position 8 conferred higher activity than methoxylation. For diosgenin derivatives, the aglycone was found to possess higher activity than the diglucosylated molecule; whereas substitution with rhamnoglucosides apparently results in loss of activity. Furthermore, effects of dioscorealide A, dioscorealide B, and dioscoreanone on antigen-induced release of TNF-alpha and IL-4 in the late phase reaction were also examined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.012

文献信息

• Sharma; Chand; Sati, Pharmazie, 1982, vol. 37, # 12, p. 870 - 870
  作者：Sharma、Chand、Sati

  DOI：——

  日期：——
• Anti-allergic substances from the rhizomes of Dioscorea membranacea
  作者：Supinya Tewtrakul、Arunporn Itharat

  DOI：10.1016/j.bmc.2006.08.012

  日期：2006.12

  Extracts of five species of Thai medicinal plants, locally known as Hua-Khao-Yen, were screened for anti-allergic activities using RBL-2H3 cells. Of the five species studied, the ethanolic extract of Dioscorea membranacea exhibited potent inhibitory activity against beta-hexosaminidase release as a marker of degranulation in RBL-2H3 cells, with an IC50 value of 37.5 mu g/mL. Eight compounds were isolated from this crude ethanolic extract, [two naphthofuranoxepins (1, 2), one phenanthraquinone (3), three steroids (4-6), and two steroidal saponins (7,8)], and tested for their anti-allergic activities. The results showed that dioscorealide B (2) possessed the highest activity with an IC50 value of 5.7 mu M, followed by dioscoreanone (3, IC50 = 7.7 mu M), dioscorealide A (1, IC50 = 27.9 mu M), and. diosgenin (9, IC50 = 29.9 mu M). Structure-activity relationship studies of naphthofuranoxepins on anti-allergic activity revealed that the hydroxylation at position 8 conferred higher activity than methoxylation. For diosgenin derivatives, the aglycone was found to possess higher activity than the diglucosylated molecule; whereas substitution with rhamnoglucosides apparently results in loss of activity. Furthermore, effects of dioscorealide A, dioscorealide B, and dioscoreanone on antigen-induced release of TNF-alpha and IL-4 in the late phase reaction were also examined. (c) 2006 Elsevier Ltd. All rights reserved.