E-4-O-β-D-glucopyranosyl-p-coumaric acid | 117405-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: E-4-O-β-D-glucopyranosyl-p-coumaric acid
• 英文别名: 4-O-β-D-glucopyranosyl-trans-p-coumaric acid；p-coumaric acid 4-O-glucoside；trans-p-coumaric acid β-glucopyranoside；4-O-β-D-glucosyl-4-coumaric acid；p-coumaric acid 4-O-β-D-glucopyranoside；4-O-β-D glucopyranosyl trans-phenylacrylic acid；trans-p-coumaric acid 4-O-β-D-glucopyranoside；trans-p-coumaric acid 4-O-β-D-glucoside；4-O-β-D-glucosyl-p-coumaric acid；p-coumaric acid glucoside；4-O-beta-D-glucosyl-4-coumaric acid；(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• CAS: 117405-49-9
• 化学式: C₁₅H₁₈O₈
• 分子量: 326.303
• InChiKey: LJFYQZQUAULRDF-FDGSXQGBSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  631.4±55.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  E-4-O-β-D-glucopyranosyl-p-coumaric acid 在 盐酸 作用下， 生成 D-葡萄糖 、 4-香豆酸
  参考文献：
  名称：

  The phenols and prodelphinidins of white clover flowers

  摘要：

  White clover flowers (Trifolium repens L.) contain an abundance of phenolics, namely cis- and trans-p-coumaric acid 4-O-beta-D-glucopyranoside, the 3-O-beta-D-galactopyranosides of myricetin, quercetin and kaempferol together with two new derivatives namely myricetin 3-O-(6 "-acetyl)-beta-D-galactopyranoside and kaempferol 3-O-(6 "-acetyl)-beta-D-galactopyranoside. Gallocatechin, epigallocatechin, gallocatechin-(4 alpha-8)-epigallocatechin and their corresponding prodelphinidin polymers were also present. The C-13-NMR spectra showed that the polymers consisted of only gallocatechin and epigallocatechin monomeric units with the latter being about twice as abundant in the extenders but only slightly more than that in the terminating units. The average degree of polymerization was estimated by C-13-NMR and ES-MS, which gave a remarkably consistent result of about 5.8 flavanol units. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00124-2
• 作为产物：
  描述：

  thesinine-4'-O-β-D-glucoside 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以6 mg的产率得到E-4-O-β-D-glucopyranosyl-p-coumaric acid
  参考文献：
  名称：

  Thesinine-4'-O-β-d-glucoside 来自 Borago officinalis 的第一种糖基化植物吡咯里西啶生物碱

  摘要：

  糖基化的吡咯里西啶生物碱，thesinine-4'-O-beta-D-glucoside，已从 Borago officinalis (Boraginaceae) 干燥脱脂种子的甲醇水溶液提取物中分离出来。该结构是通过光谱和化学分析确定的。

  DOI：

  10.1016/s0031-9422(02)00069-9

文献信息

• Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
  作者：Mingtao Zhao、Xulin Hong、Abdullah、Ruilian Yao、Yi Xiao

  DOI：10.1039/d0gc03595e

  日期：——

  this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) from p-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved

  生物质衍生的羟基肉桂酸酯（主要包括对香豆酸和阿魏酸）是芳香族化合物的天然来源，是高度未得到充分利用的资源。需要对其进行升级以使其在经济上可行。增值的酚类糖苷及其衍生物，均属于植物芳香族天然产物的一类，被广泛用于营养保健，制药和化妆品行业。然而，它们复杂的芳香结构使其有效的生物合成成为一个具有挑战性的过程。为了克服这个问题，我们创建了三个新颖的合成级联，用于从p合成酚糖苷（天麻素，熊果苷和红景天苷）及其衍生物（对苯二酚，酪醇，羟基酪醇和高香草醛醇）-香豆酸和阿魏酸。此外，由于生物质衍生的羟基肉桂酸酯直接提供了芳族单元，因此级联反应可实现高效的生物合成。相对于基于葡萄糖的生物合成，我们获得了相当高的生产率（高达或超过100倍的提高）。考虑到天然产物中芳族结构的普遍存在，使用生物质衍生的芳族化合物应有助于许多芳族天然产物的快速生物合成。
• New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa.
  作者：Yutaka SASHIDA、Kazunori OGAWA、Makoto KITADA、Hiroyuki KARIKOME、Yoshihiro MIMAKI、Hiroko SHIMOMURA

  DOI：10.1248/cpb.39.709

  日期：——

  Three new glucosides of (Z)-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-7-O-β-D-glucopyranosyl-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-6-O-(6-O-p-coumaroyl-β-D-glucopyranosyl)-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-6-O-(6-O-acetyl-β-D-glucopyranosyl)-6, 7, 3', 4'-tetrahydroxyaurone, together with (Z)-6-O-β-D-glucopyranosyl-6, 7, 3', 4'-tetrahydroxyaurone, and two new phenylpropanoid glucosides, 4-O-(6-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid and 4-O-(2-O-acetyl-6-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid, have been isolated from the fresh leaves of Bidens pilosa. These structures have been elucidated on the basis of spectral data and chemical correlation.

  (Z)-6，7，3'，4'-四羟基贝母酮、(Z)-7-O-β-D-吡喃葡萄糖基-6，7，3'，4'-四羟基贝母酮的三种新苷、(Z)-6-O-(6-O-对香豆酰-β-D-吡喃葡萄糖基)-6，7，3'，4'-四羟基乌酮，(Z)-6-O-(6-O-乙酰基-β-D-吡喃葡萄糖基)-6，7，3'，4'-四羟基乌酮、(Z)-6-O-β-D-glucopyranosyl-6, 7, 3', 4'-tetrahydroxyaurone，以及两种新的苯丙苷类，即 4-O-(6-O-对香豆酰-β-D-吡喃葡萄糖基)-对香豆酸和 4-O-(2-O-乙酰基-6-O-对香豆酰-β-D-吡喃葡萄糖基)-对香豆酸，是从 Bidens pilosa 的鲜叶中分离出来的。根据光谱数据和化学相关性阐明了这些结构。
• Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids
  作者：Ivan Bassanini、Jana Kapešová、Lucie Petrásková、Helena Pelantová、Kristína Markošová、Martin Rebroš、Kateřina Valentová、Michael Kotik、Kristýna Káňová、Pavla Bojarová、Josef Cvačka、Lucie Turková、Erica E. Ferrandi、Ikram Bayout、Sergio Riva、Vladimír Křen

  DOI：10.1002/adsc.201900259

  日期：——

  hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested

  酚类糖苷天然存在于许多植物中，因此通常存在于人类饮食中。由于它们存在于复杂的基质中，因此将它们与天然来源隔离通常很费力。已经发现它们的化学和酶促合成复杂，费时且昂贵，仅产生少量的糖基化产物。在寻求一种结构复杂的酚糖苷的便捷生物催化途径时，我们发现黑曲霉的芸香糖苷酶不仅有效地转化了羟基化的芳族酸（例如。香豆酸和阿魏酸）成相应的酚类芦丁糖苷，但是令人惊讶地还催化了相应糖基酯的形成。我们在这里报告系统研究的结果，该研究提出了通过糖苷酶催化完成的天然存在的糖基酯和酚类糖苷的独特合成。测试了一组芳香酸作为糖基受体，并鉴定了形成糖基酯所需的关键结构特征。根据目前的结构-活性关系研究，提出了合理的反应机理。所有产物均通过NMR和MS完全结构表征。
• Protoplumericin, an iridoid bis-glucoside in Allamanda neriifolia.
  作者：TATSUO YAMAUCHI、FUMIKO ABE、MASAKATSU TAKI

  DOI：10.1248/cpb.29.3051

  日期：——

  Protoplumericin, 13-O-(β-D-glucopyranosyl-p-coumaroyl)-plumieride (IV), was isolated from the polar fraction of the MeOH percolate of Allamanda neriifolia HOOK by means of several column chromatographies and droplet counter current chromatography. Enzymatic and alkaline transformations of IV into plumericin (I) and plumieride (III), respectively, were carried out.

  通过多次柱色谱和液滴逆流色谱，从钩藤（Allamanda neriifolia HOOK）甲醇渗滤液的极性部分中分离出原普鲁梅利辛（Protoplumericin，13-O-(β-D-吡喃葡萄糖基-对香豆酰)-普鲁梅利德（IV））。分别将IV酶促转化成普鲁梅利辛（I）和普鲁梅利德（III），并进行了碱性转化。
• UDPG: p-Coumarate glucosyltransferase activity in enzyme extracts from higher plants
  作者：L. Nagels、M. Molderez、F. Parmentier

  DOI：10.1016/0031-9422(81)83008-7

  日期：1981.1

  leaves amounted to 70μg/g fresh plant material. Enzyme extracts from Cestrum leaves were able to convert trans - p -coumaric acid-[3- 14 C] to 1- O - p -coumaroyl-β- d - glucose, using UDPG as a source of glucose. This enzyme activity could be measured only by trapping techniques, due to the presence of considerable hydrolase activity in crude enzyme extracts.

  摘要 Coleus、Pilea、Cistus和Cestrum以及成熟番茄的叶子都能将反式肉桂酸-[3- 14 C]转化为肉桂酸的葡萄糖酯。通过放射性同位素稀释法测量这些酯的池大小，发现它们的数量级为几微克/克新鲜植物材料。Cestrum 叶子中的 1-O-Caffeoyl-β-d-葡萄糖达到 70μg/g 新鲜植物材料。来自 Cestrum 叶子的酶提取物能够将反式 - p -香豆酸-[3- 14 C] 转化为 1- O - p - 香豆酰-β- d - 葡萄糖，使用 UDPG 作为葡萄糖来源。由于粗酶提取物中存在相当大的水解酶活性，因此这种酶活性只能通过捕获技术来测量。