4'-Benzyloxy-5,6,7,8-tetramethoxy-flavon | 40110-96-1

• 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: 4'-Benzyloxy-5,6,7,8-tetramethoxy-flavon
• 英文别名: 5,6,7,8-Tetramethoxy-2-(4-phenylmethoxyphenyl)chromen-4-one
• CAS: 40110-96-1
• 化学式: C₂₆H₂₄O₇
• 分子量: 448.472
• InChiKey: QGTKJWKVIVBJLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4'-Benzyloxy-5,6,7,8-tetramethoxy-flavon 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 5.0h， 生成 桔皮素
  参考文献：
  名称：

  Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography.

  摘要：

  在对柑橘（芸香科）果皮氯仿提取物中的成分进行深入研究的基础上，从柑橘果皮中分离出 13 种黄酮类化合物，其中包括两种新的黄酮类化合物。通过光谱数据分析以及结构转换或全合成，确认了这些黄酮的结构。此外，还分离出了β-谷甾醇、柠檬甙、橙皮甙、阿魏酸和 5, 5'-oxydimethylene-bis(2-furaldehyde) 等黄酮以外的成分。通过气-液色谱法对所获得的多取代黄酮类化合物进行了检测，这些化合物可能为柑橘类化学分类学研究提供了一个很好的标记。

  DOI：

  10.1248/cpb.28.717
• 作为产物：
  描述：

  4-苯甲氧基苯(甲)酰氯 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 4'-Benzyloxy-5,6,7,8-tetramethoxy-flavon
  参考文献：
  名称：

  B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production

  摘要：

  Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-alpha-stimulated human lens epithelial cells, the 2'-hydroxylated analogue 5a exerted marked inhibitory effects (IC50: 0.4 mu M) on PMA-treated cells, which were 170-fold more potent than those on TNF-alpha-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.001

文献信息

• Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography.
  作者：MUNEKAZU IINUMA、SHIN MATSUURA、KAZUAKI KUROGOCHI、TSUGIO TANAKA

  DOI：10.1248/cpb.28.717

  日期：——

  Thirteen kinds of flavones, including two new flavones, were isolated from the fruit peel of Citrus reticulata BLANCO (Rutaceae) on the basis of thorough examination of the components in the chloroform extract of the peel. The structures of these flavones were confirmed by analysis of the spectral data and by structural conversion or total synthesis. β-Sitosterol, limonin, hesperidin, ferulic acid, and 5, 5'-oxydimethylene-bis(2-furaldehyde) were also isolated as components other than flavones. The multisubstituted flavones obtained were examined by gas-liquid chromatography, and may provide a good marker for chemotaxonomical studies of Citrus species.

  在对柑橘（芸香科）果皮氯仿提取物中的成分进行深入研究的基础上，从柑橘果皮中分离出 13 种黄酮类化合物，其中包括两种新的黄酮类化合物。通过光谱数据分析以及结构转换或全合成，确认了这些黄酮的结构。此外，还分离出了β-谷甾醇、柠檬甙、橙皮甙、阿魏酸和 5, 5'-oxydimethylene-bis(2-furaldehyde) 等黄酮以外的成分。通过气-液色谱法对所获得的多取代黄酮类化合物进行了检测，这些化合物可能为柑橘类化学分类学研究提供了一个很好的标记。
• Inhibitor of aldose reductase
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：US04532254A1

  公开（公告）日：1985-07-30

  An inhibitor of aldose reductase which contains, as the effective ingredient, a flavone derivative having the following formula: ##STR1## wherein R.sub.1 is hydrogen atom or hydroxyl group, R.sub.2 is hydroxyl group or methoxyl group or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. The inhibitor is useful for preventing, reducing or treating complications of diabetes.

  一种醛糖还原酶抑制剂，其有效成分为含有以下结构式的黄酮衍生物：##STR1## 其中R.sub.1为氢原子或羟基，R.sub.2为羟基或甲氧基，或其药学上可接受的盐，并含有药学上可接受的载体。该抑制剂可用于预防、减少或治疗糖尿病的并发症。
• Biotransformation of Polymethoxylated Flavonoids:  Access to Their 4‘-<i>O</i>-Demethylated Metabolites
  作者：Didier Buisson、Jérôme Quintin、Guy Lewin

  DOI：10.1021/np070084q

  日期：2007.6.1

  Regioselective O-demethylation of the flavones tangeretin (1) and 3-hydroxytangeretin (6) into their 4'-O-demethylated metabolites was performed by using an Aspergillus niger strain. This method serves as a straightforward alternative to multistep synthesis or semisynthesis. The microbial approach is complementary to the chemical procedure, which furnishes a 5-O-demethylated product. P450 inhibitors

  通过使用黑曲霉菌株将黄酮橘红素（1）和3-羟基橘皮素（6）区域选择性地O-去甲基化成它们的4'-O-去甲基化的代谢物。该方法可作为多步合成或半合成的直接替代方法。微生物方法是化学过程的补充，化学过程提供了5-O-去甲基化的产物。P450抑制剂阻止了橘皮苷的生物转化（1）。这些结果表明，P450氧化系统可能参与了这种O-去甲基化，并证明了聚甲氧基黄酮在微生物和哺乳动物代谢中的相似性。
• US4532254A
  申请人：——

  公开号：US4532254A

  公开（公告）日：1985-07-30
• B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production
  作者：Tetsuta Oshitari、Yuji Okuyama、Yoshiki Miyata、Hiroshi Kosano、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1016/j.bmc.2011.10.001

  日期：2011.12

  Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-alpha-stimulated human lens epithelial cells, the 2'-hydroxylated analogue 5a exerted marked inhibitory effects (IC50: 0.4 mu M) on PMA-treated cells, which were 170-fold more potent than those on TNF-alpha-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9. (C) 2011 Elsevier Ltd. All rights reserved.