Resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside | 328090-92-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: Resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside
• 英文别名: resveratrol (E)-dehydrodimer 11-O-beta-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[3-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 328090-92-2
• 化学式: C₃₄H₃₂O₁₁
• 分子量: 616.621
• InChiKey: ZJIBDVBTKQSZQZ-REZQOROLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside 在 acetate buffer 、 β-glucosidase 作用下， 反应 24.0h， 生成 trans-δ-viniferin
  参考文献：
  名称：

  Two New Stilbene Dimer Glucosides from Grape (Vitis vinifera) Cell Cultures

  摘要：

  Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-beta -D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11'-O-beta -D-glucopyranoside (2), were isolated together with the known resveratrol (E)-dehydrodimer (3) and pallidol (4) from Vitis vinifera cell cultures. The structures and stereochemistry of the new compounds were determined on the basis of spectroscopic data analysis. Compounds 1 and 2 are dimers that belong to a new type of oligostilbene formed from a resveratrol unit and a resveratrol glucoside unit. Compounds 1 and 3 exhibited nonspecific inhibitory activity against cyclooxygenase-l and -2, with IC50 values in the range of 5 muM, whereas compound 4 was approximately 10-fold less active.

  DOI：

  10.1021/np000426r
• 作为产物：
  描述：

  resveratrol 3-O-α-glucoside 在 laccase from Trametes versicolor 、 β-glucosidase from almonds 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 、 Resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside
  参考文献：
  名称：

  漆酶催化的Piceid，白藜芦醇葡糖苷的二聚及其进一步的酶促精制

  摘要：

  漆酶催化的吡喹啉，白藜芦醇植物抗毒素白藜芦醇的3-β- D-吡喃葡萄糖基衍生物-Piceid的氧化，可以分离相应的β-5（如反式-脱氢二聚体），避免色谱分离，收率高（45％）。然后将该化合物置于市售水解酶小文库的作用下。虽然来自木霉的木霉纤维素酶能够完全水解二糖基化的二聚体，得到相应的β-5像反式白藜芦醇的脱氢二聚体，杏仁中的β-葡萄糖苷酶可以以合理的产率分离出单糖基化的中间体。分离的二聚体产物的非对映异构体和对映异构体使用半制备手性色谱柱进行了分离。已经确定了这些新二聚体的基本抗氧化剂性能。

  DOI：

  10.1002/adsc.201500185

文献信息

• Laccase-Catalyzed Dimerization of Piceid, a Resveratrol Glucoside, and its Further Enzymatic Elaboration
  作者：Paolo Gavezzotti、Federica Bertacchi、Giovanni Fronza、Vladimír Křen、Daniela Monti、Sergio Riva

  DOI：10.1002/adsc.201500185

  日期：2015.5.26

  The laccase‐catalyzed oxidation of piceid, the 3‐β‐D‐glucopyranosyl derivative of the stilbenic phytoalexin resveratrol, allowed isolation of the corresponding β‐5 like trans‐dehydrodimer in good yield (45%) avoiding chromatography. This compound was then submitted to the action of a small library of commercially available hydrolases. While the cellulase from Trichoderma viride was able to fully hydrolyze

  漆酶催化的吡喹啉，白藜芦醇植物抗毒素白藜芦醇的3-β- D-吡喃葡萄糖基衍生物-Piceid的氧化，可以分离相应的β-5（如反式-脱氢二聚体），避免色谱分离，收率高（45％）。然后将该化合物置于市售水解酶小文库的作用下。虽然来自木霉的木霉纤维素酶能够完全水解二糖基化的二聚体，得到相应的β-5像反式白藜芦醇的脱氢二聚体，杏仁中的β-葡萄糖苷酶可以以合理的产率分离出单糖基化的中间体。分离的二聚体产物的非对映异构体和对映异构体使用半制备手性色谱柱进行了分离。已经确定了这些新二聚体的基本抗氧化剂性能。
• Two New Stilbene Dimer Glucosides from Grape (<i>Vitis </i><i>v</i><i>inifera</i>) Cell Cultures
  作者：Pierre Waffo-Teguo、Dongho Lee、Muriel Cuendet、Jean-Michel Mérillon、John M. Pezzuto、A. Douglas Kinghorn

  DOI：10.1021/np000426r

  日期：2001.1.1

  Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-beta -D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11'-O-beta -D-glucopyranoside (2), were isolated together with the known resveratrol (E)-dehydrodimer (3) and pallidol (4) from Vitis vinifera cell cultures. The structures and stereochemistry of the new compounds were determined on the basis of spectroscopic data analysis. Compounds 1 and 2 are dimers that belong to a new type of oligostilbene formed from a resveratrol unit and a resveratrol glucoside unit. Compounds 1 and 3 exhibited nonspecific inhibitory activity against cyclooxygenase-l and -2, with IC50 values in the range of 5 muM, whereas compound 4 was approximately 10-fold less active.