artemisinic acid 3-β-O-β-D-glucopyranoside | 1392216-23-7

• 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: artemisinic acid 3-β-O-β-D-glucopyranoside
• CAS: 1392216-23-7
• 化学式: C₂₁H₃₂O₈
• 分子量: 412.48
• InChiKey: HKTLDAQDVYRZLC-QMHNJGMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  136.68
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  artemisinic acid 3-β-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 2.0h， 生成 可得然胶 、 3-β-hydroxyartemisinic acid
  参考文献：
  名称：

  Three sesquiterpene compounds biosynthesised from artemisinic acid using suspension-cultured cells of Averrhoa carambola (Oxalidaceae)

  摘要：

  A new sesquiterpene glycoside, artemisinic acid 3-beta-O-beta-D-glucopyranoside (3, 31.24%) and other two biotransformation products, 3-beta-hydroxyartemisinic acid (2, 36.69%) and 3-beta-hydroxyartemisinic acid beta-D-glucopyranosyl ester (4, 7.03%), were biosynthesised after artemisinic acid (1) was administered to the cultured cells of Averrhoa carambola. The three biotransformation products were obtained for the first time by using the suspension-cultured cells of A. carambola as a new biocatalyst system, and their structures were identified on the basis of the physico-chemical properties, NMR and mass spectral analyses. The results indicate that the cultured cells of A. carambola have the abilities to hydroxylate and glycosylate sesquiterpene compounds in a regio- and stereoselective manner. Furthermore, the anti-tumour activity of compounds 3 and 4 was evaluated against K562 and HeLa cell lines. Compound 4 showed strong activity against HeLa cell line, with the IC50 value of 0.56 mu molmL(-1).

  DOI：

  10.1080/14786419.2011.589055