rutin palmitate | 823789-36-2

• 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: rutin palmitate
• 英文别名: [(2S,3R,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] hexadecanoate
• CAS: 823789-36-2
• 化学式: C₄₃H₆₀O₁₇
• 分子量: 848.939
• InChiKey: IMTVOEVUZGLECQ-YKQFVSLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  272
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  棕榈酸 、 芦丁 在 silica gel 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 以33 %的产率得到rutin palmitate
  参考文献：
  名称：

  芦丁的化学和区域选择性酶促脂化，以及芦丁酯衍生物的理化和抗氧化特性

  摘要：

  酶是有机绿色化学中最强大的工具之一，酶反应具有区域选择性和对映选择性等众多优势，以及其环保和可持续的性质。更具体地，根据底物的性质和水含量，脂肪酶可以催化酯水解和形成。在此，重点是使用微生物来源的脂肪酶开发天然化合物的酶催化亲脂性，并研究最佳反应条件，最终旨在改善化合物的特性。类黄酮二糖芦丁（槲皮素-3- O-芸香苷）是构​​建酰化方案的模型化合物，允许建立有效的程序，同时提供使用状​​态-开发快速、清晰和稳健的方法的可能性。最先进的技术，用于分析和纯化合成的化合物。采用丙烯酸树脂固定化南极假丝酵母脂肪酶B，结合二氧化硅作为脱水剂，在55℃下最佳反应72小时，并进行产物纯化，转化率高达50%。对酯化化合物的理化和抗氧化性能进行了全面表征和评估。所产生的芦丁酯的亲脂性随着烷基链长度的增加而增加，但与母体化合物相比，抗氧化性能不受影响。建立了一种预备有用的酰化方案，可以全面研究酰化化合物的性质。

  DOI：

  10.1039/d3ra06333j

文献信息

• Quercetin based derivatives as sirtuin inhibitors
  作者：Vladimír Heger、Jonna Tyni、Attila Hunyadi、Lubica Horáková、Maija Lahtela-Kakkonen、Minna Rahnasto-Rilla

  DOI：10.1016/j.biopha.2019.01.035

  日期：2019.3

  Polyphenols synthesized by plants and fungi have various pharmacological effects. The ability of polyphenols to modulate sirtuins has gained considerable interest due to the role of sirtuins in aging, insulin sensitivity, lipid metabolism, inflammation, and cancer. In particular, sirtuin 6 (SIRT6) has gained importance in regulating a variety of cellular processes, including genomic stability and glucose metabolism. On the other hand, quercetin has been demonstrated to modulate sirtuins and to protect against several chronic diseases. In this study, two quercetin derivatives, diquercetin and 2-chloro-1,4-naphtoquinone-quercetin, were identified as promising SIRT6 inhibitors with IC50 values of 130 mu M and 55 mu M, respectively. 2-Chloro-1,4-naphtoquinone-quercetin also showed potent inhibition against SIRT2, with an IC50 value of 14 mu M. Diquercetin increased the Km value of NAD(+), whereas 2-chloro-1,4-naphthoquinone-quercetin increased the Km value of the acetylated substrate. Molecular docking studies suggest that diquercetin prefers the binding site of the nicotinamide (NAM) moiety, whereas 2-chloro-1,4-naphtoquinone-quercetin prefers to dock into the substrate binding site. Overall, the results of in vitro studies and molecular modeling indicate that diquercetin competes with nicotinamide adenine dinucleotide (NAD(+)), whereas 2-chloro-1,4-naphthoquinone-quercetin competes with the acetylated substrate in the catalytic site of SIRT6. Natural polyphenolic compounds targeting sirtuins show promise as a new approach in the search for novel and effective treatments for age-related diseases.
• Scalable Preparation of High Purity Rutin Fatty Acid Esters
  作者：Bena-Marie Lue、Zheng Guo、Marianne Glasius、Xuebing Xu

  DOI：10.1007/s11746-009-1471-7

  日期：2010.1

  AbstractInvestigations into expanded uses of modified flavonoids are often limited by the availability of these high purity compounds. As such, a simple, effective and relatively fast method for isolation of gram quantities of both long and medium chain fatty acid esters of rutin following scaled‐up biosynthesis reactions was established. Acylation reactions of rutin and palmitic or lauric acids were efficient in systems containing dried acetone and molecular sieves, yielding from 70–77% bioconversion after 96 h. Thereafter, high purity isolates (>97%) were easily obtained in significant quantities following a two‐step solvent purification procedure whereby excess fatty acid substrate was first removed in a heptane/water (4:1, v/v) system, followed by selective ester extraction using an ethyl acetate/water system (1:6, v/v) at elevated temperature.