(6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (Z)-9-octadecenoate | 1237535-18-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (Z)-9-octadecenoate
• 英文别名: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-octadec-9-enoate
• CAS: 1237535-18-0
• 化学式: C₃₉H₅₂O₁₃
• 分子量: 728.834
• InChiKey: HAXSOHCDOYWAQM-QILKISJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  异槲皮苷 、 油酸乙酯 在 Novozym 435 作用下， 以 2-甲基-2-丁醇 为溶剂， 65.0 ℃ 、70.0 kPa 条件下， 反应 72.0h， 生成 (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (Z)-9-octadecenoate
  参考文献：
  名称：

  Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters

  摘要：

  The enzymatic acylation of isoquercitrin with fatty acid esters of various carbon chain lengths was carried out in 2-methyl-2-butanol using Novozym 435(R). The conversion yield and the initial rate decreased from 66% to 38% and from 17.7 to 10.1 mu mol/h respectively, as the carbon chain of the acyl donor increased from C4 to C18. Isoquercitrin acylated derivatives showed higher xanthine oxidase inhibition activities than isoquercitrin. This property increased with the lipophilicity of the derivative esters. The scavenging activity of isoquercitrin esters against ABTS and DPPH radicals decreased with the acyl chain length. Conversely. for esters from C6 to C18, a linear growing relationship can be established between the chain length and the superoxide radical scavenging activity. Furthermore, an improved antiproliferative effect on Caco2 cancer cells was induced by addition of isoquercitrin esters comparing with isoquercitrin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2009.10.012

文献信息

• Sonochemical enzyme-catalyzed regioselective acylation of flavonoid glycosides
  作者：Ziaullah、H.P. Vasantha Rupasinghe

  DOI：10.1016/j.bioorg.2016.01.005

  日期：2016.4

  This work compares a highly efficient and alternative method of sonication-assisted lipase catalyzed acylation of quercetin-3-O-glucoside and phloretin-2′-glucoside, using Candida antarctica lipase B (Novozyme 435®), with a range of fatty acids. In this study, sonication-assisted irradiation coupled with stirring has been found to be more efficient and economical than conventional reaction conditions

  这项工作比较槲皮素-3-超声辅助的脂肪酶催化酰化的高效和可替代方法ö糖苷和根皮素-2'-葡糖苷，使用南极假丝酵母脂肪酶B（的Novozyme 435 ®），具有一定范围的脂肪酸。在这项研究中，发现超声辅助辐射与搅拌相结合比常规反应条件更有效，更经济。超声辅助的酰化作用加快了反应速度，并使所需时间减少了4-5倍。
• Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin
  作者：Ziaullah、Khushwant S. Bhullar、Sumudu N. Warnakulasuriya、H.P. Vasantha Rupasinghe

  DOI：10.1016/j.bmc.2012.11.034

  日期：2013.2

  Our present investigation describes the regioselective enzymatic acylation of two series of acylated derivatives of phloridzin and isoquercitrin with six different long chain saturated, mono- and poly-unsaturated fatty acids. The biocatalytic synthesis was optimized to achieve 81–98% yields, using immobilized lipase B, from Candida antarctica (Novozym 435®), in acetone at 45 °C. The synthesized esters

  我们目前的研究描述了Phloridzin和异槲皮素的两个系列酰化衍生物与六个不同的长链饱和，单和多不饱和脂肪酸的区域选择性酶促酰化作用。使用固定化的南极假丝酵母脂肪酶B （Novozym435®）在45°C的丙酮中，对生物催化合成进行了优化，可达到81-98％的产率。合成的酯已通过1 H NMR，13 C NMR光谱进行了分析，并使用体外试验评估了其抗氧化能力和酪氨酸酶抑制作用。在所有的根皮苷和异槲皮苷衍生物，抑制酪氨酸酶的活性（最大电位p ⩽0.05）通过异槲皮苷的α亚麻酸酯显示。
• An efficient microwave-assisted enzyme-catalyzed regioselective synthesis of long chain acylated derivatives of flavonoid glycosides
  作者：Ziaullah、H.P. Vasantha Rupasinghe

  DOI：10.1016/j.tetlet.2013.01.103

  日期：2013.4

  This work describes a method of microwave-assisted regioselective enzymatic acylation, using Novozyme 435 (R), of quercetin-3-O-glucoside (isoquercitrin) and phloretin-2'-glucoside (phloridzin) with different long chain saturated, mono-, and poly-unsaturated fatty acids. The synthesized esters were analyzed by H-1 NMR, and C-13 NMR spectroscopy. In this investigation, microwave irradiation under solvent free condition has been found to be more efficient and economical than conventional conditions both, in terms of time and energy. (c) 2013 Elsevier Ltd. All rights reserved.