α,β-dihydrorhaponticin | 266997-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α,β-dihydrorhaponticin
• 英文别名: α,α'-dihydro-3,3'-dihydroxy-5β-D-O-glucopyranosyloxy-4-methoxystilbene；3-HYDROXY-5-(2-(3-HYDROXY-4-METHOXYPHENYL)ETHYL)PHENYL beta-D-GLUCOPYRANOSIDE；(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 266997-59-5
• 化学式: C₂₁H₂₆O₉
• 分子量: 422.432
• InChiKey: GDZSRLULWTWRJK-YMQHIKHWSA-N

物化性质

• 沸点：
  696.7±55.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  α,β-dihydrorhaponticin 在 cellulase 作用下， 以 水 为溶剂， 反应 48.0h， 以0.6 mg的产率得到α,α'-dihydro-3,5,3'-trihydroxy-4-methoxystilbene
  参考文献：
  名称：

  Stilbenoids from Tragopogon orientalis

  摘要：

  A phytochemical investigation of Tragopogon orientalis L. (Asteraceae, Cichorieae) yielded the natural products 6 ''-O-(7,8-dihydro-caffeoyi)-alpha,beta-dihydrorhaponticin, 3 '-O-methyl-alpha,beta-dihydrorhaponticin, and (S)-3-(4-beta-glucopyranosyloxybenzyl)-7-hydroxy-5-methoxyphtalide as well as known compounds alpha,beta-dihydrorhaponticin, 3-(4-methoxybenzyl)-5,7-dimethoxyphthalide, p-dihydrocoumaric acid methyl ester, and 1-hydroxypinoresinol-1-O-beta-glucopyranoside. The structures were established by HR mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy. Moreover, the radical scavenging activities of the major compounds were measured using the 2,2-diphenyl-l-picrylhydrazyl (DPPH) assay. The chemosystematic impact of the occurrence of stilbene derivatives in T orientalis is discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.06.031
• 作为产物：
  描述：

  勒胖停 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 α,β-dihydrorhaponticin
  参考文献：
  名称：

  大黄中的抗氧化剂成分：斯蒂芬类化合物对两种新蒽醌葡萄糖苷的活性和结构的结构要求。

  摘要：

  发现从5种大黄中提取的甲醇对DPPH自由基和.O2-具有清除活性。从大黄（Rheum undulatum L.）的根茎中分离出两个新的蒽醌葡糖苷，以及两个蒽醌葡糖苷，萘葡糖苷和10个对苯二酚。在对大黄成分的自由基清除活性的筛选试验中，丁苯二酚和萘葡萄糖苷具有活性，而蒽醌和番石榴苷则没有活性。此外，大多数对苯二酚通过叔丁基氢过氧化物抑制红细胞膜的脂质过氧化。对各种相关化合物的清除作用的详细研究表明以下结构要求；1）酚羟基对显示活性至关重要；2）没食子酰基部分增强活性；3）葡糖苷部分降低活性；4）二氢二苯乙烯衍生物保持对DPPH自由基的清除活性，但它们对.O2-的活性较弱。另外，具有3-羟基和4'-甲氧基的几个对苯二酚抑制黄嘌呤氧化酶。

  DOI：

  10.1016/s0968-0896(00)00215-7

文献信息

• Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages
  作者：Hisashi Matsuda、Tadashi Kageura、Toshio Morikawa、Iwao Toguchida、Shoichi Harima、Masayuki Yoshikawa

  DOI：10.1016/s0960-894x(99)00702-7

  日期：2000.2

  Two new anthraquinone glucosides [chrysophanol 8-O-beta-D-(6'-galloyl)-glucopyranoside, aloe-emodin 1-O-beta-D-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-beta-D-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2 "-O-gallate, rhaponticin 6 "-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages. (IC50 = 11-69 mu M). The oxygen Functions (-OH,-OCH3) at the benzene ring were found to be essential to show the activity. Whereas, the glucoside moiety reduced the activity, while the alpha,beta-double bond did not affect the activity. Furthermore; the active stilbenes (rhapontigenin, piceatannol, resveratrol) inhibited iNOS induction. (C) 2000 Elsevier Science Ltd. All rights reserved.