polydatin-6''-O-yl palmitate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: polydatin-6''-O-yl palmitate
• 英文别名: trans-resveratrol-3-O-(6’-O-hexadecanoyl)-β-D-glucopyranoside；(E)-1-(3-(6'-O-hexadecanoyl)-β-D-glucopyranosyloxy-5-hydroxyphenyl)-2-(4-hydroxyphenyl)ethene；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-2-yl]methyl hexadecanoate
• 化学式: C₃₆H₅₂O₉
• 分子量: 628.803
• InChiKey: YZIULMCHXOHEID-GLYBYPTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  十六酸乙烯酯 、 虎杖甙 在 Thermomyces lanuginosus lipase 作用下， 以 2-甲基四氢呋喃 为溶剂， 生成 polydatin-6''-O-yl palmitate
  参考文献：
  名称：

  Highly efficient enzymatic synthesis of novel polydatin prodrugs with potential anticancer activity

  摘要：

  Efficient lipase-mediated research work was successfully exploited for synthesizing, potential 6 ''-O-acylpolydatin prodrugs in biomass-derived 2-methyltetrahydrofuran (2-MeTHF). The results of the enzyme recognitions of nine acyl donors evidently demonstrated that the position and number of the C-C double bond in acyl chains profoundly influenced the behavior of the enzyme, which could be attributable to the resonance effect between the double bond and carbonyl group. Further investigations showed that introducing various acyl groups into the polydatin apparently enhanced its pH stability and 1-octanol-water partition coefficient (log P). With regard to the human cervical cancer siHa cell apoptosis by a flow cytometry assay, the lipophilic 6 ''-O-sorboyl-polydatin exhibited improved apoptosis-inducing capability than the parent drug. The presence of the more lipophilic sorboyl chain in the acylated derivative could account for this. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2016.09.028

文献信息

• Polydatin-fatty acid conjugates are effective antioxidants for stabilizing omega 3-containing bulk fish oil and fish oil emulsions
  作者：Taiwo O. Akanbi、Susan N. Marshall、Colin J. Barrow

  DOI：10.1016/j.foodchem.2019.125297

  日期：2019.12

  α-tocopherol. Results of thiobarbituric acid tests showed that in bulk fish oil, all esters were more effective than α-tocopherol at 2 mmol/kg concentration but were not as effective as BHT. In fish oil-emulsions, all esters were more effective than both BHT and α-tocopherol at 2 mmol/kg concentration. The synthesized polydatin esters are promising antioxidants for oil/fat-based foods.

  南极假丝酵母研究了脂肪酶B催化的多肽的亲脂性酯的合成及其抗氧化活性。研究并优化了溶剂，底物摩尔比，酶浓度，分子筛的添加，反应温度和时间等合成参数对酯生产的影响。用丙酮作为反应溶剂可获得最高的酯产量。将酯的抗氧化活性与市售的丁基化羟基甲苯（BHT）和α-生育酚进行了比较。与BHT和α-生育酚相比，所有的聚丁二烯酸酯都更有效地抑制β-胡萝卜素的氧化破坏。硫代巴比妥酸测试结果表明，在散装鱼油中，所有酯类在2 mmol / kg浓度下均比α-生育酚更有效，但不如BHT有效。在鱼油乳液中，所有酯在2 mmol / kg浓度下均比BHT和α-生育酚更有效。合成的聚丁二烯酸酯是用于油脂类食品的有前途的抗氧化剂。
• Preventive Oral Treatment with Resveratrol Pro-prodrugs Drastically Reduce Colon Inflammation in Rodents
  作者：Mar Larrosa、Joao Tomé-Carneiro、María J. Yáñez-Gascón、David Alcántara、María V. Selma、David Beltrán、María T. García-Conesa、Cristina Urbán、Ricardo Lucas、Francisco Tomás-Barberán、Juan C. Morales、Juan Carlos Espín

  DOI：10.1021/jm1007006

  日期：2010.10.28

  There is no pharmaceutical or definitive surgical cure for inflammatory bowel diseases (IBDs). The naturally occurring polyphenol resveratrol exerts anti-inflammatory properties. However, its rapid metabolism diminishes its effectiveness in the colon. The design of prodrugs to targeting active molecules to the colon provides an opportunity for therapy of IBDs. Herein we explore the efficacy of different resveratrol prodrugs and pro-prodrugs to ameliorate colon inflammation in the murine dextran sulfate sodium (DSS) model. Mice fed with a very low dose (equivalent to 10 mg for a 70 kg-person) of either resveratrol-3-O-(6'-O-butanoyl)-beta-D-glucopyranoside (6) or resveratrol-3-O-(6'-O-octanoyl)-beta-D-glucopyranoside (7) did not develop colitis symptoms and improved 6-fold the disease activity index (DAI) compared to resveratrol. Our results indicate that these pro-prodrugs exerted a dual effect: (1) they prevented the rapid metabolism of resveratrol and delivered higher quantities of resveratrol to the colon and (2) they reduced mucosal barrier imbalance and prevented diarrhea, which consequently facilitated the action of the delivered resveratrol in the colon mucosa.