[(1R,6S,7S,8R,9R)-4-(3,4-二羟基苯基)-9-(羟基甲基)-7-[(2S,3R,4R,5S,6S)-3,4,5-三羟基-6-甲基-四氢吡喃-2-基]氧基-2,5,10-三氧杂双环[4.4.0]癸-8-基] (E)-3-(3,4-二羟基苯基)丙-2-烯酸酯 | 61276-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: [(1R,6S,7S,8R,9R)-4-(3,4-二羟基苯基)-9-(羟基甲基)-7-[(2S,3R,4R,5S,6S)-3,4,5-三羟基-6-甲基-四氢吡喃-2-基]氧基-2,5,10-三氧杂双环[4.4.0]癸-8-基] (E)-3-(3,4-二羟基苯基)丙-2-烯酸酯
• 中文别名: [(1R,6S,7S,8R,9R)-4-(3,4-二羟基苯基)-9-(羟基甲基)-7-[(2S,3R,4R,5S,6S)-3,4,5-三羟基-6-甲基-四氢吡喃-2-基]氧基-2,5,10-三氧杂双环[4.4.0]癸-8-基](E)-3-(3,4-二羟基苯基)丙-2-烯酸酯
• 英文名称: orobanchoside
• 英文别名: creanatoside；crenatoside；oraposide；[(2S,4aR,6R,7R,8S,8aR)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-7-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 61276-16-2
• 化学式: C₂₉H₃₄O₁₅
• 分子量: 622.58
• InChiKey: FPOYEEKZOOLVJA-WLLRULDYSA-N

物化性质

• 沸点：
  890.4±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(1R,6S,7S,8R,9R)-4-(3,4-二羟基苯基)-9-(羟基甲基)-7-[(2S,3R,4R,5S,6S)-3,4,5-三羟基-6-甲基-四氢吡喃-2-基]氧基-2,5,10-三氧杂双环[4.4.0]癸-8-基] (E)-3-(3,4-二羟基苯基)丙-2-烯酸酯 在 盐酸 作用下， 以 水 为溶剂， 生成 L-rhamnopyranose
  参考文献：
  名称：

  Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2019.112189