5-O-beta-D-吡喃葡萄糖苷芹菜甙元 | 28757-27-9

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 5-O-beta-D-吡喃葡萄糖苷芹菜甙元
• 英文名称: apigenin 5-O-β-D-glucopyranoside
• 英文别名: apigenin 5-O-glucoside；apigenin 5-O-β-glucopyranoside；Apigenin 5-O-beta-D-glucopyranoside；7-hydroxy-2-(4-hydroxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 28757-27-9
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: ZFPMFULXUJZHFG-QNDFHXLGSA-N

物化性质

• 熔点：
  226-227 °C
• 沸点：
  814.2±65.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 储存条件：
  存放温度应控制在2-8℃之间，需保持干燥并密封保存。

制备方法与用途

salipurpin（5-葡萄糖基芹菜素）是从三尖杉的枝叶中提取出的一种黄酮类化合物，具有一定的抗炎活性。

反应信息

• 作为反应物：
  描述：

  5-O-beta-D-吡喃葡萄糖苷芹菜甙元 在 苹果酸 作用下， 生成 德国春黄菊油
  参考文献：
  名称：

  Flavonoid 5-glucosides from Prunus cerasus bark and their characteristic weak glycosidic bonding

  摘要：

  Pinostrobin 5-glucoside, a novel flavanone glycoside, was isolated from the bark of Prunus cerasus. As it was not found in P. avium, the substance is useful to distinguish these two species. Apigenin 5-glucoside genkwanin 5-glucoside and neosakuranin were also isolated from the bark of P. cerasus. They occur in both species as minor components. These 5-glucosides together with genistein 5-glucoside, prunetin 5-glucoside, sakuranin, tectochrysin 5-glucoside and luteolin 5-glucoside were hydrolysed in malic acid. The isoflavone and flavone 5-glucosides were shown to be hydrolysed more rapidly than the flavanone 5-glucosides, whereas no hydrolysis was observed with the corresponding 7-glucosides under the same conditions. The chalcone 2'-glucoside neosakuranin was transformed at first to the corresponding flavanone 5-glucoside, which was hydrolysed thereafter.

  DOI：

  10.1016/0031-9422(91)84200-c
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 5-O-beta-D-吡喃葡萄糖苷芹菜甙元
  参考文献：
  名称：

  Zemplen; Mester, Chemische Berichte, 1943, vol. 76, p. 776

  摘要：

  DOI：

文献信息

• Differentially evolved glucosyltransferases determine natural variation of rice flavone accumulation and UV-tolerance
  作者：Meng Peng、Raheel Shahzad、Ambreen Gul、Hizar Subthain、Shuangqian Shen、Long Lei、Zhigang Zheng、Junjie Zhou、Dandan Lu、Shouchuang Wang、Elsayed Nishawy、Xianqing Liu、Takayuki Tohge、Alisdair R. Fernie、Jie Luo

  DOI：10.1038/s41467-017-02168-x

  日期：——

  Decoration of phytochemicals contributes to the majority of metabolic diversity in nature, whereas how this process alters the biological functions of their precursor molecules remains to be investigated. Flavones, an important yet overlooked subclass of flavonoids, are most commonly conjugated with sugar moieties by UDP-dependent glycosyltransferases (UGTs). Here, we report that the natural variation of rice flavones is mainly determined by OsUGT706D1 (flavone 7-O-glucosyltransferase) and OsUGT707A2 (flavone 5-O-glucosyltransferase). UV-B exposure and transgenic evaluation demonstrate that their allelic variation contributes to UV-B tolerance in nature. Biochemical characterization of over 40 flavonoid UGTs reveals their differential evolution in angiosperms. These combined data provide biochemical insight and genetic regulation into flavone biosynthesis and additionally suggest that adoption of the positive alleles of these genes into breeding programs will likely represent a potential strategy aimed at producing stress-tolerant plants.

  植物化学物质的修饰对自然界的代谢多样性起着重要作用，然而这一过程如何改变它们前体分子的生物功能尚待研究。黄酮类化合物是一类重要但常被忽视的类黄酮类化合物，它们通常通过UDP依赖型糖苷转移酶（UGTs）与糖基结合。在这里，我们报告了水稻黄酮类化合物的自然变异主要由OsUGT706D1（黄酮7-O-葡萄糖基转移酶）和OsUGT707A2（黄酮5-O-葡萄糖基转移酶）确定。紫外线B暴露和转基因评估表明它们的等位变异在自然界中有助于UV-B耐受性。对超过40种黄酮类化合物UGTs的生化特性表征揭示了它们在被子植物中的差异进化。这些综合数据提供了关于黄酮合成的生化见解和遗传调控，并额外建议将这些基因的正等位基因引入育种计划，可能代表一种旨在生产耐逆植物的潜在策略。