3-O-acetyl resveratrol

• 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: 3-O-acetyl resveratrol
• 英文别名: [3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenyl] acetate；[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl] acetate
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: FATXNQWLANBPPI-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-acetyl resveratrol 在 苄基三乙基氯化铵 、 sodium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 50.0h， 生成 3-甲氧基-5-[2-(4-甲氧基苯基)乙烯基]苯酚
  参考文献：
  名称：

  白藜芦醇甲氧基衍生物的合成及生物学评价

  摘要：

  白藜芦醇是一种天然存在的二苯乙烯，具有许多有益的健康作用。各种研究证明了其多种生物学作用，包括抗氧化、抗炎和抗血小板特性，从而支持其心脏保护、神经保护和抗癌活性的潜力。然而，白藜芦醇的一个显着限制是其生物利用度较弱。为了克服这一挑战，多个研究小组研究了新型白藜芦醇衍生物的合成，以提高生物利用度和药理活性。然而，关于白藜芦醇衍生物对血小板功能影响的数据有限。因此，本研究的目的是合成白藜芦醇甲氧基衍生物并评价其抗血小板和抗增殖活性。利用从健康志愿者获得的富血小板血浆（PRP）来评估衍生物抑制血小板激活因子（PAF）、二磷酸腺苷（ADP）和凝血酶受体激活肽（TRAP）诱导的血小板聚集的能力。此外，还针对 PC-3 和 HCT116 细胞的增殖评估了衍生物的抗肿瘤活性。结果表明，与原始化合物相比，白藜芦醇的一些甲氧基衍生物表现出相当甚至更好的抗血小板活性。最有效的衍生物是 4'-甲氧基衍生物，它对

  DOI：

  10.3390/molecules28145547
• 作为产物：
  描述：

  白藜芦醇 在 吡啶 、 Candida antarctica lipase 作用下， 以 正丁醇 为溶剂， 反应 0.5h， 生成 3-O-acetyl resveratrol
  参考文献：
  名称：

  Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues

  摘要：

  The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4'-trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI(50) = 24.09 muM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI(50) = 2.92 muM) and 19 (GI(50) = 25.39 muM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.08.003

文献信息

• Nitric oxide donating derivatives for the treatment of cardiovascular disorders
  申请人：Tucker Joseph

  公开号：US20050080024A1

  公开（公告）日：2005-04-14

  Compounds comprising nitric oxide derivatives of stilbenes, polyphenols and flavonoids and methods of their use are provided for treating patients suffering from any of hypercholesterolemia, vascular oxidative stress and endothelial dysfunction.

  本发明提供了由stilbenes、多酚和类黄酮的亚硝酸盐衍生物组成的化合物，以及它们的使用方法，用于治疗患有高胆固醇血症、血管氧化应激和内皮功能障碍的患者。
• Novel Sirtuin Activating Compounds and Methods for Making the Same
  申请人：Andrus Merritt B.

  公开号：US20080255382A1

  公开（公告）日：2008-10-16

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及一种制备白藜芦醇、白藜芦醇酯和给定以下结构式的取代和未取代的stilbenes的方法；其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m独立地取值为0、1、2、3、4或5，每个A和每个B独立地从Pn、R或缺席中选择，每个V和每个W独立地从Pn、由（2）到（6）个碳原子的直链或支链烷基和由（3）到（8）个碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群体中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步过程制备的，其中包括在碱存在下与苄基卤和苯乙烯偶联合成N-杂环碳型配体偶联。这些化合物在食品、化妆品和制药行业中显示出增强的稳定性。
• Nitric oxide donating derivatives of stilbenes, polyphenols and flavonoids for the treatment of cardiovascular disorders
  申请人：Tucker Joseph

  公开号：US20050080021A1

  公开（公告）日：2005-04-14

  Compounds and methods are provided for treating patients suffering from any of hypercholesterolemia, vascular oxidative stress and endothelial dysfunction.

  提供了用于治疗患有高胆固醇血症、血管氧化应激和内皮功能障碍的患者的化合物和方法。
• Regioselective Lipase-Catalyzed Synthesis of 3-<i>O</i>-Acyl Derivatives of Resveratrol and Study of Their Antioxidant Properties
  作者：Pamela Torres、Ana Poveda、Jesús Jimenez-Barbero、Antonio Ballesteros、Francisco J. Plou

  DOI：10.1021/jf903210q

  日期：2010.1.27

  affording the diester 3,4′-di-O-acetylresveratrol and finally the peracetylated derivative. Long saturated and unsaturated fatty acid vinyl esters were also effective as acyl donors with similar regioselectivity. In contrast, lipase B from Candida antarctica catalyzes the acylation of the phenolic group 4′-OH with 80% yield and negligible formation of higher esters. The analysis of the antioxidant properties

  增加白藜芦醇生物利用度的方法之一是保护其3-OH酚基。在这项工作中，白藜芦醇在3-OH上的区域选择性酰化反应是通过固定化来自Alcaligenes sp。的脂肪酶催化的乙酸乙烯酯的酯交换反应实现的。（脂肪酶QLG）。3- O-乙酰基白藜芦醇的最大产率约为75％，因为脂肪酶还催化其进一步的乙酰化，从而提供二酯3,4'-二-O-乙酰基白藜芦醇，最后得到全乙酰化的衍生物。长的饱和和不饱和脂肪酸乙烯基酯也可以作为酰基给体，具有相似的区域选择性。相反，南极假丝酵母的脂肪酶B催化酚基4'-OH的酰化反应，产率为80％，高级酯的形成可忽略不计。抗氧化剂性能的分析表明，在3-OH处，乙酰基和硬脂酰基衍生物的Trolox等效抗氧化剂能力（TEAC）值分别为白藜芦醇的40％和25％。与在4'-OH位置相比，在3-OH位置添加酰基链导致更高的活性损失。
• Immobilized Lipase Based on Hollow Mesoporous Silicon Spheres for Efficient Enzymatic Synthesis of Resveratrol Ester Derivatives
  作者：Liu-Jia Xu、Tao Yang、Jing Wang、Feng-Hong Huang、Ming-Ming Zheng

  DOI：10.1021/acs.jafc.0c07501

  日期：2021.8.18

  Enzymatic esterification of resveratrol is crucial for its potential application in lipophilic foods and drugs. However, the poor activity of the free enzyme hinders the reaction. In this work, the highly efficient enzymatic synthesis of resveratrol ester derivatives was achieved by immobilized lipase on hydrophobic modified hollow mesoporous silicon spheres (HMSS-C8). We preliminarily explored the

  白藜芦醇的酶促酯化对其在亲脂性食品和药物中的潜在应用至关重要。然而，游离酶的低活性阻碍了反应。在这项工作中，通过将脂肪酶固定在疏水改性中空介孔硅球 (HMSS-C 8 )上，实现了白藜芦醇酯衍生物的高效酶促合成。我们初步探讨了念珠菌的使用。用于白藜芦醇酰化的 99-125 脂肪酶 (CSL)，对 3-OH- 超过 4'-OH-酰化具有区域选择性。HMSS-C 8为 CSL 提供了理想的适应能力，负载能力高达 652 mg/g。CSL@HMSS-C 8的催化效率比游离 CSL 高 15 倍，白藜芦醇的转化率仅在 2 小时内达到 98.7%，是目前文献中记录的最快值。10 个循环后，转化率保持高达 86.3%。受益于更好的脂溶性，含单酯衍生物的油的相对氧化稳定性指数值分别比精制油和含白藜芦醇的油高43.1%~68.8%和23.9%~33.2%。该研究为白藜芦醇酯衍生物的高效酶法合成提供了一条新