β-D-glucopyranosyl <β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-23-al-28-oate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: β-D-glucopyranosyl <β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-23-al-28-oate
• 英文别名: 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranoside；gypsogenin 3-O-β-D-glucuronopyranosyl-28-O-β-D-glucopyranoside；β-D-glucopyranosyl [β-D-glucuronopyranosyl-(1-> 3)]-3β-hydroxyolean-12-en-23-al-28-oate；(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4-formyl-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₄₂H₆₄O₁₅
• 分子量: 808.961
• InChiKey: KFNNEUAROQLUQS-ZJDNFKTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  250
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranosyl <β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-23-al-28-oate 在 盐酸 、 水 、 ammonium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 山梨醇
  参考文献：
  名称：

  Evaluation of novel antioxidant triterpenoid saponins from the halophyte Salicornia herbacea

  摘要：

  As a part of an ongoing search for novel antioxidants from the salt marsh plants, bioactivity-isolation and structure determination of constituents from Salicornia herbacea were performed. One new triterpenoid saponin (4), along with three known saponins (1-3), has been isolated from n-BuOH fraction of S. herbacea. On the basis of the spectroscopic methods, the structure of the new saponin 4 was elucidated as 3 beta-hydroxy-23-oxo-30-noroleana-12, 20(29)-diene-28-oic acid 3-O-beta-D-glucuronopyranosyl-28-O-beta-D-glucopyranoside. Scavenging effects of saponins 1-4 were examined on 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical and peroxynitrite. Particularly, saponin 3 exerted significant antioxidant activity on both authentic peroxynitrite and peroxynitrite generated from morpholinosydnonimine (SIN-1). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.017

文献信息

• Molluscicidal saponins from Swartzia simplex
  作者：Christian Borel、Mahabir P. Gupta、Kurt Hostettmann

  DOI：10.1016/s0031-9422(00)83572-4

  日期：1987.1

  Abstract One monodesmosidic saponin and six bidesmosidic saponins have been isolated from the methanolic extract of the leaves of Swartzia simplex . They were shown to be glucuronides of oleanolic acid, gypsogenin and gypsogenic acid by chemical and spectral means. The monodesmosidic saponins exhibit various molluscicidal activities against the schistosomiasis-transmitting snail Biomphalaria glabrata

  摘要 从紫藤叶甲醇提取物中分离得到1 种单节皂苷和6 种双节皂苷。通过化学和光谱手段，它们被证明是齐墩果酸、石膏原素和石膏酸的葡糖醛酸苷。Monodesmosidic 皂苷对传播血吸虫病的蜗牛 Biophalaria glabrata 表现出多种杀软体动物的活性。