quercetin complex with β-cyclodextrin | 502590-80-9

• 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 complex with β-cyclodextrin
• 英文别名: quercetin complex with β-CD
• CAS: 502590-80-9
• 化学式: C₁₅H₁₀O₇*C₄₂H₇₀O₃₅
• 分子量: 1437.24
• InChiKey: KVLGPRHFVIUKHY-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.24
• 重原子数：
  99.0
• 可旋转键数：
  8.0
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  685.41
• 氢给体数：
  26.0
• 氢受体数：
  42.0

反应信息

• 作为产物：
  描述：

  槲皮素 、 β-环糊精 在 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 生成 quercetin complex with β-cyclodextrin
  参考文献：
  名称：

  包合物对亚硝酸与类黄酮反应的影响。

  摘要：

  使用分光光度法研究了水溶液中槲皮素和儿茶素亚硝酸反应的动力学。结果表明，这些抗氧化剂参与了与亚硝酸的氧化反应，亚硝酸在温和的酸性条件下源自亚硝酸根离子的质子化。分光光度法检测到了相对稳定的邻醌。已经检查了反应的pH依赖性，并且通过动力学曲线的非线性拟合获得了反应的速率常数。β-环糊精对氧化途径的影响是该研究的另一个目的。结果表明，β-环糊精对氧化反应具有抑制作用。

  DOI：

  10.1016/j.saa.2011.06.070

文献信息

• Synthesis, characterization, molecular modeling, binding energies of β-cyclodextrin-inclusion complexes of quercetin: Modification of photo physical behavior upon β-CD complexation
  作者：Karuppiah Nagaraj、Chelladurai Karuppiah、Mohammad Ahmad Wadaan、Prasenjit Maity、Raja Kaliyaperumal、Ellappan Vaishnavi、D. Rajaraman、S.M. Abhijith、Sayee Kannan Ramaraj、Isai Mathivanan

  DOI：10.1016/j.saa.2024.124091

  日期：2024.5

  studies also supported the formation of 1:1 drug-CD soluble complexes. All these spectral results provide insight into the binding behavior of substrate into CD cavity in the order per-6-ABCD > Mono-6-ABCD > γ-CD > β-CD > α-CD. The proposed model also finds strong support from the fact with excess CD this exciton coupling disappears indicates the formation of only 1:1 complex.

  我们从茶叶中制备了一种天然存在的黄酮类化合物，即槲皮素，并通过吸收、发射、FT-IR、H、C nmr 光谱和 ESI-MS 分析进行分析。槲皮素在环糊精（如 α-、β-、γ-、per-6-ABCD 和 mono-6-ABCD 空腔）中的包合行为得到了紫外可见、发射、FT-IR 和 ICD 光谱以及能量最小化研究的支持。根据吸收和发射结果，发现形成的复合物的类型取决于主体：客体的化学计量。槲皮素 CD 复合物的 FT-IR 数据支持底物与 α-、β- 和 γ-CD 形成包合物。槲皮素与 α-、β-、γ-CD、per-6-ABCD 和 mono-6-ABCD 的主客体络合提供了有关 CD 的非常有价值的信息：槲皮素复合物，该研究还表明 β-CD络合提高了槲皮素的水溶性、化学稳定性和生物利用度。此外，相溶解度研究也支持1:1药物-CD可溶性复合物的形成。所有这些光谱结果提供了对底物与 CD 腔的结合行为的深入了解，顺序为
• Nguyen, Hoa-Du; Pham, Duc-Truc; Lincoln, Stephen F., Asian Journal of Chemistry, 2011, vol. 23, # 1, p. 116 - 118
  作者：Nguyen, Hoa-Du、Pham, Duc-Truc、Lincoln, Stephen F.

  DOI：——

  日期：——
• One-pot β-cyclodextrin-assisted extraction of active ingredients from Xue–Zhi–Ning basing its encapsulated ability
  作者：Hui-Jie Zhang、Ya-Nan Liu、Meng Wang、Yue-Fei Wang、Yan-Ru Deng、Ming-Lei Cui、Xiao-Liang Ren、Ai-Di Qi

  DOI：10.1016/j.carbpol.2015.06.072

  日期：2015.11

  Xue-Zhi-Ning (XZN) is a traditional Chinese medicine formula, containing active ingredients with poor solubility in water, which has been demonstrated to be helpful for patients with hyperlipidemia. One-pot beta-cyclodextrin ( beta-CD)-assisted extraction of active ingredients from XZN has been carried out to develop an efficient and eco-friendly extraction process. Five active compounds rubrofusarin gentiobioside, 2,3,5,4'-tetrahydroxy-stilbene-2-O-beta-D-glucoside, emodin, nuciferine and quercetin were identified by UPLC/DAD/MS and used as indexes to evaluate the process optimized by an orthogonal test. The results showed that addition of beta-CD significantly enhanced the extraction ratios of all five components. The enhancement of extraction ratios was positively correlated with the apparent formation constants between beta-CD and the compounds. The study also showed that the stabilities and dissolution rates of the active ingredients were improved in the presence of beta-CD. This one-pot beta-cyclodextrin-assisted extraction has the potential to be applied in pharmaceutical preparations directly. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, characterization, antioxidant activity of Quercetin, Rutin and Quercetin-Rutin incorporated β-cyclodextrin inclusion complexes and determination of their activity in NIH-3T3, MDA-MB-231 and A549 cell lines
  作者：A. Alper Öztürk、Ebru Başaran、Behiye Şenel、Müzeyyen Demirel、Şenay Sarıca

  DOI：10.1016/j.molstruc.2023.135169

  日期：2023.6