2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-O-β-D-glucopyranosyloxy-2(E)-butenenitrile | 930275-36-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-O-β-D-glucopyranosyloxy-2(E)-butenenitrile
• 英文别名: (E)-2-cyano-4-(β-D-glucopyranosyloxy)but-2-en-1-yl 4-hydroxy-3-methoxybenzoate；nigrumin-4-hydroxy-3-methoxybenzoate；ribetril D；[(E)-2-cyano-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] 4-hydroxy-3-methoxybenzoate
• CAS: 930275-36-8
• 化学式: C₁₉H₂₃NO₁₀
• 分子量: 425.392
• InChiKey: UWNLOPFIHDWHDR-UDEHJMMBSA-N

物化性质

• 沸点：
  751.9±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  179
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-O-β-D-glucopyranosyloxy-2(E)-butenenitrile 在 盐酸 、 水 作用下， 反应 2.0h， 生成 葡萄糖
  参考文献：
  名称：

  Isolation, Structure Determination, and Sensory Activity of Mouth-Drying and Astringent Nitrogen-Containing Phytochemicals Isolated from Red Currants (Ribes rubrum)

  摘要：

  Application of chromatographic separation and taste dilution analyses recently revealed, besides a series of flavon-3-ol glycosides and (E)/(Z)-aconitic acid, four nitrogen-containing phytochemicals as the key astringent and mouth-drying compounds in red currants (Ribes rubrum). The isolation and structure determination of the astringent indoles 3-carboxymethyl-indole-1-N-beta-D-glucopyranoside (1) and 3-methylcarboxymethyl-indole-1-N-beta-D-glucopyranoside (2), as well as the astringent, noncyanogenic nitriles 2-(4-hydroxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (3) and 2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (4) by means of 1D/2D NMR, LC-MS/MS, and UV-vis spectroscopy are reported. The structures of compounds 1 and 2 were confirmed by synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying nitrogen compounds were determined to be between 0.0003 and 5.9 mu mol/L (water). In particular, the extraordinarily low threshold of 0.0003 mu mol/L evaluated for the indole 1 represents the lowest recognition threshold of any astringent phytochemical reported to date.

  DOI：

  10.1021/jf0632076

文献信息

• ALKALOID COMPOSITIONS FROM RIBES SPECIES TO TREAT CONDITIONS ASSOSIATED WITH MITOCHONDRIAL FUNCTION OR INHIBITION OF PDE4, PDE5 AND IKK-BETA
  申请人：Asiros A/S

  公开号：EP2859007A1

  公开（公告）日：2015-04-15
• ALKALOID COMPOSITIONS FROM RIBES SPECIES TO TREAT CONDITIONS ASSOCIATED WITH MITOCHONDRIAL FUNCTION OR INHIBITION OF PDE4, PDE5 AND IKK-BETA
  申请人：Olle Svenssons Partiaffär AB

  公开号：EP2859007B1

  公开（公告）日：2019-04-17
• Bioactive Alkaloid Compositions and Their Medical Uses
  申请人：Asiros A/S

  公开号：US20160184338A1

  公开（公告）日：2016-06-30

  The present invention relates to a novel alkaloid and novel bioactive alkaloid fractions derivable from Ribes preferably selected among Ribes Rubrum and Ribes nigrum ; methods of manufacturing such bioactive Ribes alkaloid fractions and their use for the inhibition of IKK-β, PDE4 and/or PDE5 and in addition their promoting effect on mitochondrial biogenesis and function; their therapeutic or non-therapeutic applications as nutritive or medicinal products in the management of conditions associated with impaired mitochondrial function or IKK-β, PDE4 and/or PDE5 activity, such as inflammation, neurodegeneration, dyslipidemia, type 2 diabetes mellitus, impaired wound healing, sarcopenia and other conditions associated with muscle dysfunction or tiredness and fatigue, or where optimization of muscular or cognitive function is desired; extracts, juices or concentrates of Ribes comprising such alkaloids; compositions comprising such alkaloids, including pharmaceutical compositions, nutritive product such as functional foods and nutraceutical compositions, and cosmetic compositions and medical devices.
• US9023816B2
  申请人：——

  公开号：US9023816B2

  公开（公告）日：2015-05-05
• [EN] ALKALOID COMPOSITIONS FROM RIBES SPECIES TO TREAT CONDITIONS ASSOSIATED WITH MITOCHONDRIAL FUNCTION OR INHIBITION OF PDE4, PDE5 AND IKK-BETA<br/>[FR] COMPOSITIONS ALCALOÏDES PROVENANT D'ESPÈCES DU GENRE RIBES DESTINÉES À TRAITER DES ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE FONCTION MITOCHONDRIALE OU À L'INHIBITION DE PDE4, DE PDE5 ET D'IKK-BETA
  申请人：ASIROS AS

  公开号：WO2015007291A1

  公开（公告）日：2015-01-22

  The present invention relates to a novel alkaloid and novel bioactive alkaloid fractions derivable from Ribes preferably selected among Ribes Rubrum and Ribes nigrum; methods of manufacturing such bioactive Ribes alkaloid fractions and their use for the inhibition of IKK-β, PDE4 and/or PDE5 and in addition their promoting effect on mitochondrial biogenesis and function; their therapeutic or non- therapeutic applications as nutritive or medicinal products in the management of conditions associated with impaired mitochondrial function or IKK-β, PDE4 and/or PDE5 activity, such as inflammation, neurodegeneration, dyslipidemia, type 2 diabetes mellitus, impaired wound healing, sarcopenia and other conditions associated with muscle dysfunction or tiredness and fatigue, or where optimization of muscular or cognitive function is desired; extracts, juices or concentrates of Ribes comprising such alkaloids; compositions comprising such alkaloids, including pharmaceutical compositions, nutritive product such as functional foods and nutraceutical compositions, and cosmetic compositions and medical devices.