(E)-4-(3,5-dihydroxystyryl)phenyl butyrate | 1217011-16-9

• 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: (E)-4-(3,5-dihydroxystyryl)phenyl butyrate
• 英文别名: 4'-butyrate trans-resveratrol；4'-butyrate resveratrol；4'-O-butanoylresveratrol；(E)-4-(3,5-dihydroxystyryl)phenol butyrate；[4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenyl] butanoate
• CAS: 1217011-16-9
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: LOMLSBQUIMOHOR-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-4-(3,5-bis(methoxymethoxy)styryl)phenol butyrate 在 盐酸 作用下， 以 乙醚 为溶剂， 以73%的产率得到(E)-4-(3,5-dihydroxystyryl)phenyl butyrate
  参考文献：
  名称：

  白藜芦醇4'-酯类似物的合成及其在恶性黑色素瘤和胰腺细胞株中的评价

  摘要：

  合成了疾病预防剂白藜芦醇的4'-酯类似物，并评估了其作为抗黑素瘤和胰腺癌药物的潜力。使用脱羰Heck偶联剂组装受保护的二苯乙烯核结构。与正常的NHDF细胞相比，DM443和DM738细胞具有4'-乙酸和棕榈酸酯类似物的选择性活性。

  DOI：

  10.1016/j.bmcl.2009.12.006

文献信息

• Separation and Identification of Resveratrol Butyrate Ester Complexes and Their Bioactivity in HepG2 Cell Models
  作者：Ming-Kuei Shih、You-Lin Tain、Chiu-Min Cheng、Chien-Ning Hsu、Yu-Wei Chen、Hung-Tse Huang、Chi-I Chang、Chih-Yao Hou

  DOI：10.3390/ijms222413539

  日期：——

  capacity and anti-fat accumulation activity in previous studies. In this study, silica gel, high-performance liquid chromatography, and 1H nuclear magnetic resonance were used for separation and identification of RBE complex components. With the exception of resveratrol, five different structures of ester derivatives were separated from silica gel: 3,4′-di-O-butanoylresveratrol (ED2, 18.8%), 3-O-butanoylresveratrol

  在先前的研究中，白藜芦醇丁酸酯 (RBE) 复合物已表现出更高的抗氧化能力和抗脂肪积累活性。本研究采用硅胶、高效液相色谱、1H核磁共振等方法对RBE复合物组分进行分离鉴定。除白藜芦醇外，从硅胶中分离出五种不同结构的酯衍生物：3,4'-二-O-丁酰白藜芦醇（ED2, 18.8%）、3-O-丁酰白藜芦醇（ED4, 35.7%）、4'- O-丁酰白藜芦醇 (ED5, 4.4%)、3,5,4'-三-O-丁酰白藜芦醇 (ED6, 1.5%) 和 3,5-二-O-丁酰白藜芦醇 (ED7, 0.7%)。在获得的酯衍生物中，ED2 和 ED4 是 RBE 复合物中的主要酯衍生物。因此，评估了 RBE 混合物、ED2 和 ED4 的细胞抗氧化活性。结果表明，ED2和ED4的抗氧化能力高于RBE混合物，表明丁酸酯化位点的数量和位置与细胞存活率和抗氧化能力有关。本研究首次报道了 RBE 复合物衍生物的成功分离、结构鉴定和细胞生物抗氧化活性，这是
• Lipophilization of Resveratrol and Effects on Antioxidant Activities
  作者：Won Young Oh、Fereidoon Shahidi

  DOI：10.1021/acs.jafc.7b03129

  日期：2017.10.4

  lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging

  白藜芦醇（R）是一种多酚，通过与选定脂肪酸的酯化反应进行结构改性，以扩大其在亲脂性食品，药物和化妆品中的潜在应用。酯化反应使用12种不同的脂肪酸，具有不同的链长和不饱和度（C3：0–C22：6）。通过高效液相色谱-质谱法鉴定了两个单酯，两个二酯和一个三酯，以及单酯（R-3- O-单二十二碳六烯酸酯和R-4'- O-单十二碳六烯酸酯）在结构上通过核磁共振证实。白藜芦醇及其烷基酯的亲脂性是使用ALOGPS 2.1计算的。白藜芦醇在2,2-二苯基-1-吡啶并肼基（DPPH）和2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）自由基阳离子清除试验中均显示出更高的抗氧化活性。在DPPH自由基清除试验中，具有长链脂肪酸（C18：0和C18：1）的白藜芦醇酯显示出更高的抗氧化活性，而短链脂肪酸（C3：0，C4：0和C6：0）显示出更高的抗氧化活性。 ABTS自由基阳离子清除测定中的抗氧化剂活
• Resveratrol Butyrate Esters Inhibit BPA-Induced Liver Damage in Male Offspring Rats by Modulating Antioxidant Capacity and Gut Microbiota
  作者：Jin-Xian Liao、Yu-Wei Chen、Ming-Kuei Shih、You-Lin Tain、Yao-Tsung Yeh、Min-Hsi Chiu、Sam K. C. Chang、Chih-Yao Hou

  DOI：10.3390/ijms22105273

  日期：——

  Resveratrol can affect the physiology or biochemistry of offspring in the maternal–fetal animal model. However, it exhibits low bioavailability in humans and animals. Fifteen-week SD pregnant female rats were orally administered bisphenol A (BPA) and/or resveratrol butyrate ester (RBE), and the male offspring rats (n = 4–8 per group) were evaluated. The results show that RBE treatment (BPA + R30) compared with the BPA group can reduce the damage caused by BPA (p < 0.05). RBE enhanced the expression of selected genes and induced extramedullary hematopoiesis and mononuclear cell infiltration. RBE increased the abundance of S24-7 and Adlercreutzia in the intestines of the male offspring rats, as well as the concentrations of short-chain fatty acids (SCFAs) in the feces. RBE also increased the antioxidant capacity of the liver by inducing Nrf2, promoting the expression of HO-1, SOD, and CAT. It also increased the concentration of intestinal SCFAs, enhancing the barrier formed by intestinal cells, thereby preventing BPA-induced metabolic disruption in the male offspring rats, and reduced liver inflammation. This study identified a potential mechanism underlying the protective effects of RBE against the liver damage caused by BPA exposure during the peri-pregnancy period, and the influence of the gut microbiota on the gut–liver axis in the offspring.

  白藜芦醇可以影响母胎动物模型中后代的生理或生物化学。然而，在人类和动物中，其生物利用度较低。本研究口服双酚A（BPA）和/或白藜芦醇丁酸酯（RBE）给15周SD孕妇大鼠，评估其雄性后代大鼠（每组n = 4-8）。结果表明，与BPA组相比，RBE治疗（BPA + R30）可以减轻BPA引起的损伤（p <0.05）。 RBE增强了选择基因的表达，并诱导了骨髓外造血和单核细胞浸润。 RBE增加了雄性后代大鼠肠道中S24-7和Adlercreutzia的丰度，以及粪便中短链脂肪酸（SCFAs）的浓度。 RBE还通过诱导Nrf2，促进HO-1，SOD和CAT的表达，增加了肝脏的抗氧化能力。它还增加了肠道SCFAs的浓度，增强了肠细胞形成的屏障，从而预防了BPA引起的代谢紊乱，并减少了雄性后代大鼠的肝脏炎症。本研究确定了RBE对孕期暴露于BPA引起的肝脏损伤的保护作用的潜在机制，以及肠道菌群对后代肠道-肝脏轴的影响。
• Synthesis and Characterization of Novel Resveratrol Butyrate Esters That Have the Ability to Prevent Fat Accumulation in a Liver Cell Culture Model
  作者：You-Lin Tain、Li-Cheng Jheng、Sam K. C. Chang、Yu-Wei Chen、Li-Tung Huang、Jin-Xian Liao、Chih-Yao Hou

  DOI：10.3390/molecules25184199

  日期：——

  absorption (1751 cm−1) in the ester region. 13C-NMR spectrum of RBE showed a peak at 171 ppm corresponding to the ester group and peaks between 1700 and 1600 cm−1 in the FTIR spectra. RBE treatment (25 or 50 μM) decreased oleic acid-induced lipid accumulation in HepG2 cells. This effect was stronger than that of resveratrol and mediated through the downregulation of p-ACC and SREBP-2 expression. This is

  为了促进广泛的应用和增强生物活性，白藜芦醇被酯化为白藜芦醇丁酸酯 (RBE)。与丁酸的酯化反应在室温下通过 Steglich 酯化方法与 N-乙基-N'-(3-二甲基氨基丙基)碳二亚胺 (EDC) 和 4-二甲基氨基吡啶 (DMAP) 进行。我们的实验表明，通过 EDC 和 DMAP 促进的酯化反应合成 RBE 是成功的，并且 RBE 的 FTIR 光谱显示酯区有吸收 (1751 cm-1)。RBE 的 13C-NMR 谱在 171 ppm 处显示了对应于酯基的峰，在 FTIR 谱中出现了 1700 至 1600 cm-1 之间的峰。RBE 处理（25 或 50 μM）降低了油酸诱导的 HepG2 细胞中的脂质积累。这种作用比白藜芦醇更强，并且是通过下调 p-ACC 和 SREBP-2 表达介导的。这是第一项证明 RBE 可以通过 Steglich 方法合成的研究，并且由此产生的 RBE 可以抑制
• Selective esterification of the polyphenol resveratrol at the 4′-position
  作者：Mark J. Acerson、Merritt B. Andrus

  DOI：10.1016/j.tetlet.2013.12.019

  日期：2014.1

  Selective esterification of the polyphenol resveratrol was performed under thermodynamic conditions using NaH and acid anhydrides to directly access 4 '-esters. Standard conditions with acetyl chloride and pyridine showed poor selectivity, favoring esterification at the 3-position. The extended 4 '-phenolate anion is generated in preference to the 3-phenolate under the new anhydride-sodium hydride-DMSO conditions. Acylation occurs to access the 4 '-ester products with modest selectivity and yield with minimal formation of the 3-monoester, 3,5-diester, and triester products. (C) 2013 Elsevier Ltd. All rights reserved.