3-O-β-D-glucopyranosyl-28-O-(α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1-> 4)[β-D-apiofuranosyl-(1-> 3)]-α-L-rhamnopyranosyl-(1-> 2)-[4-O-(3,4,5-trimethoxy-(E)-cinnamoyl-β-D-fucopyranosyl)])medicagenic acid

• 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: 3-O-β-D-glucopyranosyl-28-O-(α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1-> 4)[β-D-apiofuranosyl-(1-> 3)]-α-L-rhamnopyranosyl-(1-> 2)-[4-O-(3,4,5-trimethoxy-(E)-cinnamoyl-β-D-fucopyranosyl)])medicagenic acid
• 英文别名: securidacaside B
• 化学式: C₇₅H₁₁₂O₃₅
• 分子量: 1573.69
• InChiKey: XPXHHDFAYALTOD-VYKJUGBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.09
• 重原子数：
  110.0
• 可旋转键数：
  21.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  522.57
• 氢给体数：
  16.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  3-O-β-D-glucopyranosyl-28-O-(α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1-> 4)[β-D-apiofuranosyl-(1-> 3)]-α-L-rhamnopyranosyl-(1-> 2)-[4-O-(3,4,5-trimethoxy-(E)-cinnamoyl-β-D-fucopyranosyl)])medicagenic acid 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 D-木糖 、 D-apiose 、 L-阿拉伯糖 、 D-岩藻糖 、 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Bisdesmosidic Saponins fromSecuridaca longepedunculataRoots: Evaluation of Deterrency and Toxicity to Coleopteran Storage Pests

  摘要：

  Powdered dry root bark of Securidaca longepedunculata was mixed with maize and cowpea and effectively reduced the numbers of Sitophilus zeamais and Callosobruchus maculatus emerging from these commodities, respectively, more than 9 months after treatment. This effect was reciprocated in grain treated with a methanol extract of the root bark, indicating that compounds were present that were oviposition deterrents or directly toxic to the adults or larvae. Two new bisdesmosidic saponins, 3-O-beta-D-glucopyranosyl-28-O(alpha-L-arabinopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-[4-O-(4-methoxycinnamoyl-beta-D-fucopyranosyl)])-medicagenic acid (securidacaside A) and 3-O-beta-D-glucopyranosyl-28-O(alpha-L-arabinopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-[4-O-(3,4,5-trimethoxy-(E)-cinnamoyl-beta-D-fucopyranosyl)])-medicagenic acid (securidacaside B), were isolated from the methanol extract of the roots of S. longepedunculata and characterized by spectroscopic methods. Securidacaside A, which occurred as (E)- and (Z)-regioisomers, showed deterrency and toxicity toward C. maculatus and S. zeamais and could contribute to the biological activity of the methanol extract. The potential to optimize the use of this plant for stored product protection using water extracts, which would be appropriate technology for target farmers, is discussed.

  DOI：

  10.1021/jf901599j

文献信息

• Bisdesmosidic Saponins from<i>Securidaca longepedunculata</i>Roots: Evaluation of Deterrency and Toxicity to Coleopteran Storage Pests
  作者：Philip C. Stevenson、Thamara K. Dayarathna、Steven R. Belmain、Nigel C. Veitch

  DOI：10.1021/jf901599j

  日期：2009.10.14

  Powdered dry root bark of Securidaca longepedunculata was mixed with maize and cowpea and effectively reduced the numbers of Sitophilus zeamais and Callosobruchus maculatus emerging from these commodities, respectively, more than 9 months after treatment. This effect was reciprocated in grain treated with a methanol extract of the root bark, indicating that compounds were present that were oviposition deterrents or directly toxic to the adults or larvae. Two new bisdesmosidic saponins, 3-O-beta-D-glucopyranosyl-28-O(alpha-L-arabinopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-[4-O-(4-methoxycinnamoyl-beta-D-fucopyranosyl)])-medicagenic acid (securidacaside A) and 3-O-beta-D-glucopyranosyl-28-O(alpha-L-arabinopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-[beta-D-apiofuranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-[4-O-(3,4,5-trimethoxy-(E)-cinnamoyl-beta-D-fucopyranosyl)])-medicagenic acid (securidacaside B), were isolated from the methanol extract of the roots of S. longepedunculata and characterized by spectroscopic methods. Securidacaside A, which occurred as (E)- and (Z)-regioisomers, showed deterrency and toxicity toward C. maculatus and S. zeamais and could contribute to the biological activity of the methanol extract. The potential to optimize the use of this plant for stored product protection using water extracts, which would be appropriate technology for target farmers, is discussed.