quercetin-3-O-hexanoate

• 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: quercetin-3-O-hexanoate
• 英文别名: [2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] hexanoate
• 化学式: C₂₁H₂₀O₈
• 分子量: 400.385
• InChiKey: QGHUYRZEOYKSOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5,7,3',4'-penta-O-hexanoyl-quercetin 在 lipase from Mucor miehei (Lipozyme(R) IM) 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 以90%的产率得到quercetin-3-O-hexanoate
  参考文献：
  名称：

  Antimicrobial and Anti-Lipase Activity of Quercetin and its C2-C16 3-O-Acyl-Esters

  摘要：

  Neither quercetin (Q). nor 3-Ow-acylquercetines, up to 100 mug/mL, had any significant activity on selected gram-positive strains (Staphylococcus aureus, Bacillus subtilis, Listeria ivanovi, Listeria monocytogenes, Listeria serligeri), gram-negative strains (Escherichia coli, Shigella flexneri, Shigella sonnei, Salmonella enteritidis, Salmonella tiphymurium) and yeasts (Candida albicans and Candida glabrata). In addition, we confirmed the known anti-HIV activity of Q (80% inhibition at 40 muM), which might depend on the free hydroxyl in the C-3 position, as suggested by the lack of activity of the 3-O-acylquercetines. Finally, we described an interesting inhibitory activity on Candida rugosa lipase by Q (IC16 = 10(-4) M) and its esters (3-O-acylquercetines) which, in vivo, could play an important role against lipase producing microorganisms. In particular, 3-O-acyl-quercetines, being more active (IC16 = 10(-4)-10(-6) M) and more lipophilic, could be more effective than Q when applied to the skin or mucosae, and deserve to be studied further. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00275-9

文献信息

• Preparation of Quercetin Esters and Their Antioxidant Activity
  作者：Won Young Oh、Priyatharini Ambigaipalan、Fereidoon Shahidi

  DOI：10.1021/acs.jafc.9b04154

  日期：2019.9.25

  Quercetin, a polyphenolic compound, is widely distributed in plants and has numerous health benefits. However, its hydrophilicity can compromise its use in lipophilic systems. For this reason, quercetin was esterified with 12 different fatty acids as their acyl chlorides with varying chain lengths and degrees of unsaturation. Two monoesters (Q-3′-O-monoester and Q-3-O-monoester) and four diesters (Q-7

  槲皮素是一种多酚化合物，广泛分布于植物中，具有许多健康益处。但是，其亲水性会损害其在亲脂性体系中的使用。因此，槲皮素被12种不同的脂肪酸酯化为酰氯，具有不同的链长和不饱和度。两个单酯（Q-3'- O-单酯和Q-3- O-单酯）和四个二酯（Q-7,3'- O-二酯，Q-3'，4'- O-二酯，Q-3 （3'- O-二酯和Q- 3,4' - O-二酯）是主要产物，HPLC-MS和11 H-NMR数据。计算槲皮素衍生物的亲脂性；发现这随着脂肪酸链长度的增加而增加。利用DPPH自由基和ABTS自由基清除阳离子的活性来评价槲皮素及其衍生物的抗氧化能力。槲皮素在所有测试样品中显示出最高的自由基清除活性。尽管这项研究中抗氧化剂的活性有所降低，但这些衍生物在亲脂性介质中可能表现出更好的抗氧化剂活性，并且一旦被食用，它们在体内的吸收和生物利用度就会提高。
• Quercetin Inhibited the Formation of Lipid Oxidation Products in Thermally Treated Soybean Oil by Trapping Intermediates
  作者：Xu Zhang、Ling Ni、Yamin Zhu、Ning Liu、Daming Fan、Mingfu Wang、Yueliang Zhao

  DOI：10.1021/acs.jafc.1c00046

  日期：2021.3.24

  antioxidant activity in soybean oil, which explained the decreased inhibitory activity of quercetin against aldehyde formation during heat treatment. More interesting, quercetin-3-O-hexanoate showed improved cellular antioxidant activity compared to the parent quercetin. Overall, quercetin inhibited the formation of lipid oxidation products in thermally treated soybean oil by reacting with early intermediates

  在这项研究中，我们研究了槲皮素（一种受欢迎的酚类化合物）对热处理大豆油中醛形成的抑制机理。发现槲皮素显着降低了不饱和醛的形成，其抑制作用随加热时间的延长而降低。同时，与未经处理的样品相比，槲皮素对脂肪酸谱的影响最小。在经过槲皮素热处理的大豆油中形成了一些新的酚类衍生物，并通过液相色谱-串联质谱进行了进一步分析，并与新合成的衍生物（通过质谱和核磁共振谱表征）进行了比较。根据其化学结构，我们提出槲皮素与13-氧-十八碳烯酸，10-氧-十六碳烯酸，分别由亚油酸，棕榈油酸和油酸的过氧化形成的10-氧-十八碳烯酸和10-氧-十八碳烯酸可抑制醛的形成。此外，新形成的槲皮素-3-O-己酸酯，槲皮素-3- O-庚酸酯和槲皮素-3- O-壬酸酯显示较弱的2,2-二苯基-1-吡啶并肼基和2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸）大豆油中的二铵盐基自由基阳离子清除活性和较弱的抗氧化活性，这解释了槲皮素对
• Flavonoid Compounds and Uses Thereof
  申请人：Jarrott Bevyn

  公开号：US20090130051A1

  公开（公告）日：2009-05-21

  Novel flavonoid compounds having anti-oxidant activity are described. The compounds and compositions have been shown to exhibit anti-oxidant properties and are particularly useful in the treatment of ischemia and reperfusion injuries. The invention also describes a method to chemically synthesize such flavonoid compounds and test their efficacy. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have uses in the areas of pharmaceuticals, nutraceutical, and veterinary applications.

  本发明描述了具有抗氧化活性的新型黄酮类化合物。这些化合物和组合物已被证明具有抗氧化性质，特别适用于缺血和再灌注损伤的治疗。本发明还描述了一种化学合成这种黄酮类化合物并测试其功效的方法。这些化合物及其对应的药学上可接受的衍生物和/或盐在制药、保健品和兽医应用领域中有用。
• Antimicrobial and Anti-Lipase Activity of Quercetin and its C2-C16 3-O-Acyl-Esters
  作者：Maria Teresa Gatto、Serena Falcocchio、Eleonora Grippa、Gabriela Mazzanti、Lucia Battinelli、Giovanni Nicolosi、Daniela Lambusta、Luciano Saso

  DOI：10.1016/s0968-0896(01)00275-9

  日期：2002.2

  Neither quercetin (Q). nor 3-Ow-acylquercetines, up to 100 mug/mL, had any significant activity on selected gram-positive strains (Staphylococcus aureus, Bacillus subtilis, Listeria ivanovi, Listeria monocytogenes, Listeria serligeri), gram-negative strains (Escherichia coli, Shigella flexneri, Shigella sonnei, Salmonella enteritidis, Salmonella tiphymurium) and yeasts (Candida albicans and Candida glabrata). In addition, we confirmed the known anti-HIV activity of Q (80% inhibition at 40 muM), which might depend on the free hydroxyl in the C-3 position, as suggested by the lack of activity of the 3-O-acylquercetines. Finally, we described an interesting inhibitory activity on Candida rugosa lipase by Q (IC16 = 10(-4) M) and its esters (3-O-acylquercetines) which, in vivo, could play an important role against lipase producing microorganisms. In particular, 3-O-acyl-quercetines, being more active (IC16 = 10(-4)-10(-6) M) and more lipophilic, could be more effective than Q when applied to the skin or mucosae, and deserve to be studied further. (C) 2001 Elsevier Science Ltd. All rights reserved.