brandioside | 133393-81-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: brandioside
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 133393-81-4
• 化学式: C₃₇H₄₈O₂₀
• 分子量: 812.776
• InChiKey: RIHCCESRYIALPG-LQTIFAKJSA-N

物化性质

• 沸点：
  1008.3±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  310
• 氢给体数：
  10
• 氢受体数：
  20

安全信息

• 储存条件：
  -20°C，干燥密封

制备方法与用途

金石蚕苷和2-乙酰基金石蚕苷是沙苁蓉的主要化学成分，均为苯丙素类结构，具有抗氧化和神经保护活性，表现出良好的药物活性。通常，金石蚕苷从马鞭草科紫珠属植物广东紫珠或裸花紫珠中提取分离获得。然而，在这两种植物中的含量较低，且化学成分复杂，制备步骤繁琐，收率一般低于0.1%。

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 brandioside 在 吡啶 作用下， 以78 mg的产率得到
  参考文献：
  名称：

  Brandioside, a phenylpropanoid glycoside from Brandisia hancei

  摘要：

  A new phenylpropanoid glycoside, brandioside, was isolated from Brandisia hancei. Its structure, [beta-(3',4'-dihydroxylphenyl)-ethyl]-(2-O-acetyl)-(3,6-O-di-alpha -L-rhamnopyranosyl)-(4-O-caffeoyl)-beta-D-glucopyranoside, was established by chemical and spectroscopic methods.

  DOI：

  10.1016/0031-9422(91)83759-e

文献信息

• Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
  作者：Dariusz Jedrejek、Sylwia Pawelec、Renata Piwowarczyk、Łukasz Pecio、Anna Stochmal

  DOI：10.1016/j.phytochem.2019.112189

  日期：2020.2

  There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. linen, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2'-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties - phenolic acid and phenylethanoid unit.