methyl 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-indol-3-yl)acetate | 23099-32-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: methyl 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-indol-3-yl)acetate
• 英文别名: 1-β-D-glucopyranosyl-1H-indole-3-acetic acid methyl ester；3-methylcarboxymethyl-indole-1-N-β-D-glucopyranoside；N-β-D-glucopyranosyl-indole-3-methyl acetate；glucoindol B；methyl 2-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]acetate
• CAS: 23099-32-3
• 化学式: C₁₇H₂₁NO₇
• 分子量: 351.356
• InChiKey: UCJQLVSIHYDTNQ-USACIQFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-indol-3-yl)acetate 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [3'-Methoxycarbonylmethyl-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1H,1'H-[2,2']biindolyl-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

  2,2'-吲哚基吲哚啉向2,2'-双吲哚的光氧化：轻度形成的二色氨酸交联

  摘要：

  2,2'-吲哚基吲哚啉容易进行光氧化，形成对称的荧光2,2'-双吲哚。该反应在环境光下在空气中缓慢进行，但直接照射可促进反应。肽和N-糖基化的底物与这种轻度的光氧化相容。

  DOI：

  10.1016/0040-4039(96)01220-8
• 作为产物：
  描述：

  1-β-D-glucopyranosyl-1H-indole-3-acetic acid 、 三甲基硅烷化重氮甲烷 以73%的产率得到methyl 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-indol-3-yl)acetate
  参考文献：
  名称：

  水稻中吲哚-3-乙酸的代谢：N-β-d-吡喃葡萄糖基吲哚-3-乙酸及其结合物的鉴定和表征

  摘要：

  使用液相色谱-电喷雾电离-串联质谱 (LC-ESI-MS/MS) 在水稻 (Oryza sativa) 中寻找吲哚-3-乙酸 (IAA) 的结合物，以阐明 IAA 的未知代谢途径. 在大米提取物的碱性水解物中发现了 N-β-d-吡喃葡萄糖基吲哚-3-乙酸 (IAA-N-Glc)。对 3 周龄大米的定量分析表明，IAA-N-Glc 的总量与 IAA 的总量相等。基于 LC-ESI-MS/MS 的分析确定 IAA-N-Glc 的主要部分以与天冬氨酸和谷氨酸的结合形式存在。它们的水平与水稻营养生长过程中 IAA-N-Glc 的总量非常吻合。进一步的详细分析表明，两种结合物在根中高度积累。游离形式的 IAA-N-Glc 占种子总量的 60%，但在营养组织中未检测到。使用氘标记化合物的掺入研究表明 IAA-N-Glc 的氨基酸缀合物是由 IAA-氨基酸生物合成的。在拟南芥、莲藕和玉米的提取物中也发现了

  DOI：

  10.1016/j.phytochem.2007.05.040

文献信息

• Isolation, Structure Determination, and Sensory Activity of Mouth-Drying and Astringent Nitrogen-Containing Phytochemicals Isolated from Red Currants (<i>Ribes rubrum</i>)
  作者：Bernd Schwarz、Thomas Hofmann

  DOI：10.1021/jf0632076

  日期：2007.2.1

  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.
• 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