anagalligenone-3-O-α-L-arabinopyranoside

• 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: anagalligenone-3-O-α-L-arabinopyranoside
• 英文别名: (3β)-23-hydroxy-16-oxo-13,28-epoxyoleanan-3-yl α-L-arabinopyranoside；lobelioidoside A；anagalligenone 3-O-a-l-arabinopyranoside；Anagalligenone-3-O-alpha-L-arabinopyranoside；(1S,4S,5R,8R,9R,10S,13R,14R,17S,18R)-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-2-one
• 化学式: C₃₅H₅₆O₈
• 分子量: 604.825
• InChiKey: RPCCLOCZZKOVRB-PZMHSVQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  43
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  anagalligenone-3-O-α-L-arabinopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 L-(+)-arabinose
  参考文献：
  名称：

  金钱草中的四个新的13,28-环氧油烷皂苷

  摘要：

  四个新的齐墩果烷皂苷，lobelioidosides A-d（1 - 4，RESP），全是具有16氧代和23-OH基团，以及带有13,28环氧桥作为共同的部分，已经被分离提取了全叶狼毒植物全草中75％的乙醇提取物。根据MS，1 H-和13 C-NMR，HMQC，HMBC和1 H，1 H-COSY数据分析阐明了它们的结构。

  DOI：

  10.1002/hlca.201300292

文献信息

• Cytotoxic triterpenoids from Lysimachia parvifolia
  作者：Zhengchun He、Fengjie Liang、Jing Lu、Yuanjiang Pan

  DOI：10.1016/j.ejmech.2013.06.043

  日期：2013.9

  Five new oleanane-type triterpenoids, including two aglycones, 13 beta-28-epoxy-3 beta,22 alpha,23-trihydroxyolean-16-one (1) and 13 beta-28-epoxy-22 alpha,23-dihydroxyolean-3,16-dione (2), and three glycosides, anagalligenone-3-O-alpha-L-arabinopyranoside (3), anagalligenone-3-O-[beta-D-glucopyranosyl(1 -> 4)-alpha-L-arabinopyranoside] (4) and anagalligenone-3-O-[beta-D-xylopyranosyl(1 -> 2)-beta-D-glucopyranosyl(1 -> 4)-alpha-L-arabinopyranoside] (5), were isolated from the aerial parts of Lysimachia parvifolia, together with three known oleanane-type triterpenoid glycosides (6-8). The structures of the new compounds were subsequently elucidated by spectroscopic analysis and their cytotoxicities evaluated against six human cancer cell lines. Compounds 5-8 exhibited significant cytotoxicities against all the cell lines tested, with IC50 values lower than 10 mu M. The possible mechanism of action of compound 6 was also studied. (C) 2013 Elsevier Masson SAS. All rights reserved.