(2S,3R,4S,5S,6R)-2-[3-羟基-5-[(E)-2-(4-羟基-3-甲氧基苯基)乙烯基]苯氧基]-6-(羟基甲基)四氢吡喃-3,4,5-三醇 | 32727-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (2S,3R,4S,5S,6R)-2-[3-羟基-5-[(E)-2-(4-羟基-3-甲氧基苯基)乙烯基]苯氧基]-6-(羟基甲基)四氢吡喃-3,4,5-三醇
• 英文名称: isorhapontin
• 英文别名: trans-isorhapontin；trans-3,5,4’-trihydroxystilbene-3’-methoxy-3-O-β-D-glucopyranoside；(E)-isorhapontin；(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 32727-29-0
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: KLPUXMNQDCUPNO-DXKBKAGUSA-N

物化性质

• 熔点：
  193-194 °C(Solv: methanol (67-56-1); chloroform (67-66-3))
• 沸点：
  721.1±60.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-2-[3-羟基-5-[(E)-2-(4-羟基-3-甲氧基苯基)乙烯基]苯氧基]-6-(羟基甲基)四氢吡喃-3,4,5-三醇 在 草酸 作用下， 生成 异丹叶大黄素
  参考文献：
  名称：

  Isolation, structure, and synthesis of a stilbene glucoside from the bark of: Picea glauca (moench) voss.

  摘要：

  用柱层析法从白云杉树皮中分离出phlobaphenes，得到了非结晶的stilbene葡萄糖苷trans 3,4′5-三羟基-3′-甲氧基stilbene-3-O-β-D-葡萄糖苷（1）。通过去乙酰化其六乙酸酯（2）实现了纯化。化合物1经乳酶或稀酸裂解为去糖基体4和D-葡萄糖。制备了化合物1的乙酸酯、苯甲酸酯和二氢衍生物，以及化合物4的乙酸酯、苯甲酸酯、甲醚和二氢衍生物。用高锰酸盐氧化化合物1的苯甲酸酯衍生物得到了二苯甲酰-α-邻苯二酚酸。对2进行类似氧化得到了乙酰香草酸和一个未表征的酸，后者水解为D-葡萄糖和β-邻苯二酚酸。因此，化合物1的结构如上所示，并合成了其衍生物2。香草醛与3,5-二羟基苯乙酸缩合，产物经脱羧和去乙酰化。将该化合物与四-O-乙酰-α-D-葡萄糖吡喃糖溴化物缩合，得到一系列产物混合物，经乙酰化后，使用制备性薄层色谱分离，得到所需的2。

  DOI：

  10.1139/v68-414

文献信息

• Isolation, structure, and synthesis of a stilbene glucoside from the bark of: <i>Picea</i> <i>glauca</i> (moench) voss.
  作者：D. H. Andrews、J. C. Hoffman、C. B. Purves、H. H. Quon、E. P. Swan

  DOI：10.1139/v68-414

  日期：1968.8.1

  The fractionation of phlobaphenes from white spruce bark by column chromatography gave the non-crystalline stilbene glucoside trans 3,4′5-trihydroxy-3′-methoxystilbene-3-O-β-D-glucopyranoside (1). Purification was achieved through deacetylation of its hexaacetate (2). Compound 1 was cleaved with emulsin or dilute acid to the aglycone 4, and D-glucose. The acetate, benzoate, and dihydro-derivatives of 1, and the acetate, benzoate, methyl ether, and dihydro-derivatives of 4 were prepared. Oxidation of the benzoate derivative of 1 with chromic acid gave dibenzoyl-α-resorcylic acid. Similar oxidation of 2 gave acetylvanillic acid together with an uncharacterized acid which was hydrolyzed to D-glucose and β-resorcylic acid. The structure of 1 was therefore as shown, and its derivative 2 was synthesized. Vanillin was condensed with 3,5-dihydroxyphenylacetic acid and the product was decarboxylated and deacetylated. This compound was condensed with tetra-O-acetyl-α-D-glucopyranosyl bromide to yield a mixture of products which, after acetylation, were separated, using preparative thin-layer chromatography, to give the desired 2.

  用柱层析法从白云杉树皮中分离出phlobaphenes，得到了非结晶的stilbene葡萄糖苷trans 3,4′5-三羟基-3′-甲氧基stilbene-3-O-β-D-葡萄糖苷（1）。通过去乙酰化其六乙酸酯（2）实现了纯化。化合物1经乳酶或稀酸裂解为去糖基体4和D-葡萄糖。制备了化合物1的乙酸酯、苯甲酸酯和二氢衍生物，以及化合物4的乙酸酯、苯甲酸酯、甲醚和二氢衍生物。用高锰酸盐氧化化合物1的苯甲酸酯衍生物得到了二苯甲酰-α-邻苯二酚酸。对2进行类似氧化得到了乙酰香草酸和一个未表征的酸，后者水解为D-葡萄糖和β-邻苯二酚酸。因此，化合物1的结构如上所示，并合成了其衍生物2。香草醛与3,5-二羟基苯乙酸缩合，产物经脱羧和去乙酰化。将该化合物与四-O-乙酰-α-D-葡萄糖吡喃糖溴化物缩合，得到一系列产物混合物，经乙酰化后，使用制备性薄层色谱分离，得到所需的2。
• Inhibitors from Rhubarb on Lipopolysaccharide-Induced Nitric Oxide Production in Macrophages: Structural Requirements of Stilbenes for the Activity
  作者：Tadashi Kageura、Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Shoichi Harima、Mamiko Oda、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(01)00093-1

  日期：2001.7

  By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2''-O-gallate and rhaponticin 6"-O-gallate), and a naphthalene glucoside (torachrysone 8-O-beta -D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50 = 11-69 muM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the alpha,beta -double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-kappaB activation following expression of inducible NO synthase. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Talvitie, Antti; Mannila, Erkki; Kolehmainen, Erkki, Liebigs Annalen der Chemie, 1992, # 4, p. 399 - 402
  作者：Talvitie, Antti、Mannila, Erkki、Kolehmainen, Erkki

  DOI：——

  日期：——
• Antioxidant constituents from rhubarb: structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides
  作者：Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Ji-Young Park、Shoichi Harima、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(00)00215-7

  日期：2001.1

  extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and .O2-. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity

  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。