决明叶苷 | 22149-35-5

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 决明叶苷
• 中文别名: 山柰酚-3-O-龙胆二糖苷；山奈酚-3-0-龙胆二糖苷；山柰酚3-龙胆双糖苷；山奈酚3-龙胆二糖苷；山奈素3-龙胆二糖苷；山奈酚-3-O-龙胆二糖苷
• 英文名称: kaempferol 3-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: 3-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl-kaempferol；kaempferol 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside；kaempferol-3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside；3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosylkaempferol；kaempferol-3-O-β-glucopyranosyl-(1→6)-β-glucopyranoside；kaempferol 3-O-(6-O-β-D-glucopyranosyl)-β-D-glucopyranoside；Kaempferol 3-gentiobioside；5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 22149-35-5
• 化学式: C₂₇H₃₀O₁₆
• 分子量: 610.526
• InChiKey: BITPRCODIALMOV-DEFKTLOSSA-N

物化性质

• 熔点：
  210-211℃
• 沸点：
  991.0±65.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，Kaempferol 3-O-gentiobioside 是一种从龙脷叶中分离得到的黄酮类化合物，具有抗糖尿病活性。它能够抑制 α-glucosidase，并对碳水化合物酶有抑制作用，其 IC50 值为 50.0 µM。

在化学性质方面，Kaempferol 3-O-gentiobioside 是一种白色结晶粉末，可溶于甲醇、乙醇和 DMSO 等有机溶剂，来源于龙脷叶。

用途上，该化合物可用于含量测定、鉴定及药理实验等。

反应信息

• 作为反应物：
  描述：

  决明叶苷 在 盐酸 作用下， 反应 1.0h， 生成 葡萄糖 、 山奈酚
  参考文献：
  名称：

  Flavonol Glycosides from Convolvulus supinus and Their Antioxidant Activity

  摘要：

  DOI：

  10.1007/s10600-013-0785-8
• 作为产物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-7-yl]oxyoxane-2-carboxylic acid 生成 决明叶苷
  参考文献：
  名称：

  BUDZIANOWSKI, JAROMIR, PHYTOCHEMISTRY, 30,(1991) N, C. 1679-1682

  摘要：

  DOI：

文献信息

• Evolvosides C–E, flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity
  作者：Prasoon Gupta、Upasana Sharma、Praveen Gupta、Kiran Babu Siripurapu、Rakesh Maurya

  DOI：10.1016/j.bmc.2012.12.040

  日期：2013.3

  Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1-3) along with six known compounds (4-9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4'-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside, whereas evolvosides D and E (2-3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1-3) represent rare triglycoside derivatives of flavonol at C-4'. The isolated compounds (1-6) were screened for acute stress-induced biochemical changes in male Sprague-Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects. (C) 2013 Elsevier Ltd. All rights reserved.