4'-羟基汉黄芩素 | 57096-02-3

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 4'-羟基汉黄芩素
• 英文名称: 5,7,4'-trihydroxy-8-methoxyflavone
• 英文别名: 5,7,4′-trihydroxy-8-methoxy flavone；5,7,4′-trihydroxyl-8-methoxyflavone；5,7,4’-trihydroxy-8-methoxyflavone；isooscutellarein 8-methyl ether；isoscutellarein 8-methyl ether；4'-Hydroxywogonin；5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
• CAS: 57096-02-3
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: OEZZJTAJYYSQKM-UHFFFAOYSA-N

物化性质

• 熔点：
  303-305 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  578.1±50.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,7,8-三羟基-2-(4-羟基苯基)苯并吡喃-4-酮 在 O-methyl transferase from cell-free extract of Citrus mitis 、 [methyl-¹⁴C]-S-adenosyl-L-methionine 、 2-巯基乙醇 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 4'-羟基汉黄芩素 、 5,7,8-trihydroxy-4'-methoxyflavone
  参考文献：
  名称：

  橙子无细胞提取物对黄酮类化合物的 O-甲基化

  摘要：

  摘要 柑桔（Citrus mitis）的无细胞提取物催化了许多类黄酮的几乎所有羟基的O-甲基化，表明柑橘组织中存在邻位、间位、对位和3-O-甲基转移酶。后者，迄今未报道的酶，催化高良姜素和槲皮素的 3-O-甲基醚的形成。许多化合物的逐步 O-甲基化，尤其是槲皮素和槲皮素，往往表明多酶复合物表面上存在协调的 O-甲基化序列。所使用的类黄酮底物的甲基受体能力与它们的羟基取代模式和它们的负电子密度分布有关。

  DOI：

  10.1016/0031-9422(80)85102-8

文献信息

• Chromones and chromone derivatives and uses thereof
  申请人：Yen Mao-Hsiung

  公开号：US20060142211A1

  公开（公告）日：2006-06-29

  The present invention relates to chromones, novel chromone derivatives, and pharmaceutical formulations containing the same and methods of use thereof. Uses of the present invention include, but are not limited to, use for the prevention and treatment of septic shock, organ injury and other disorders. The compounds described herein can be salt forms and also water-soluble compounds.

  本发明涉及香豆素，新型香豆素衍生物，以及含有它们的制药配方和使用方法。本发明的用途包括但不限于预防和治疗败血性休克、器官损伤和其他疾病。所述化合物可以是盐形式和水溶性化合物。
• Anti-influenza virus compound comprising biflavonoid-sialic acid glycoside
  申请人：Yamada Haruki

  公开号：US20070004649A1

  公开（公告）日：2007-01-04

  The compounds of the present invention comprise biflavonoid-sialic acid conjugates. Such biflavonoid-sialic acid conjugates show anti-influenza virus activities, not only in in vitro systems using cultured cells, but also in in vivo systems using mice. Thus, they are useful as preventive or therapeutic agents for influenza, and moreover, are useful in food and drink products for preventing or treating influenza.

  本发明的化合物包括双黄酮-唾液酸共轭物。这种双黄酮-唾液酸共轭物不仅在使用培养细胞的体外系统中，而且在使用小鼠的体内系统中表现出抗流感病毒活性。因此，它们可用作流感的预防或治疗剂，并且可用于食品和饮料产品中以预防或治疗流感。
• Amentoflavone as an antiviral agent
  申请人：Advanced Life Sciences Inc.

  公开号：EP1245230A2

  公开（公告）日：2002-10-02

  Substantially purified antiviral biflavanoids robustaflavone, hinokiflavone, amentoflavone, agathisflavone, volkensiflavone, morelloflavone, rhusflavanone, succedaneaflavanone, GB-1a and GB-2a are provided. Antiviral fiflavanoid derivatives and salt forms thereof, e.g. robustaflavone tetrasulfate potassium salt, and methods for preparing the same are also disclosed. Pharmaceutical compositions which include the antiviral biflavanoids, derivatives or salts thereof are also provided. Also disclosed is an improved method for obtaining substantially pure robustaflavone from plant material. The biflavanoid compounds, derivatives or salts thereof of the invention may be used in a method for treating and/or preventing viral infections caused by viral agents such as influenza, e.g. influenza A and B; hepatitis, e.g. hepatitis B; human immunodeficiency virus, e.g. HIV-1; Herpes viruses (HSV-1 and HSV-2); Varicella Zoster virus (VZV); and measles.

  本研究提供了实质上纯化的抗病毒双黄酮类化合物--强力黄酮、桧黄酮、芒果黄酮、芒果黄酮、伏肯黄酮、麦卢黄酮、胡黄酮、琥珀黄酮、GB-1a 和 GB-2a。此外，还公开了抗病毒的五黄烷衍生物及其盐形式，例如强力黄酮四硫酸钾盐，以及制备方法。还提供了包括抗病毒双黄烷、衍生物或其盐的药物组合物。此外，还公开了一种从植物材料中获得高纯度强力黄酮的改进方法。本发明的双黄烷化合物、衍生物或其盐类可用于治疗和/或预防由病毒病原体引起的病毒感染，如流感，如甲型和乙型流感；肝炎，如乙型肝炎；人类免疫缺陷病毒，如 HIV-1；疱疹病毒（HSV-1 和 HSV-2）；水痘带状疱疹病毒（VZV）；以及麻疹。
• ANTI-INFLUENZA VIRUS COMPOUND COMPRISING BIFLAVONOID-SIALIC ACID GLYCOSIDE
  申请人：THE KITASATO INSTITUTE

  公开号：EP1600454A1

  公开（公告）日：2005-11-30

  The compounds of the present invention comprise biflavonoid-sialic acid conjugates. Such biflavonoid-sialic acid conjugates show anti-influenza virus activities, not only in in vitro systems using cultured cells, but also in in vivo systems using mice. Thus, they are useful as preventive or therapeutic agents for influenza, and moreover, are useful in food and drink products for preventing or treating influenza.

  本发明的化合物包括双黄酮--银杏酸共轭物。 因此，它们可用作流感的预防或治疗剂，而且可用于预防或治疗流感的食品和饮料产品中。
• Biflavanoids and derivatives thereof as antiviral agents
  申请人：Advanced Life Sciences, Inc.

  公开号：US20020068757A1

  公开（公告）日：2002-06-06

  Substantially purified antiviral biflavanoids robustaflavone, hinokiflavone, amentoflavone, agathisflavone, volkensiflavone, morelloflavone, rhusflavanone, succedaneaflavanone, GB-1a, and GB-2a are provided. Antiviral biflavanoid derivatives and salt forms thereof, e.g., robustaflavone tetrasulfate potassium salt, and methods for preparing the same are also disclosed. Pharmaceutical compositions which include the antiviral biflavanoids, derivatives or salts thereof are also provided alone or in combination with at least one antiviral agent such as 3TC. Also disclosed is an improved method for obtaining substantially pure robustaflavone from plant material. The biflavanoid compounds, derivatives or salts thereof of the invention may be used in a method for treating and/or preventing viral infections caused by viral agents such as influenza, e.g., influenza A and B; hepatitis, e.g., hepatitis B; human immunodeficiency virus, e.g., HIV-1; Herpes viruses (HSV-1 and HSV-2); Varicella Zoster virus (VZV); and measles. For instance, semi-synthetic hexa-O-acetate and hexa-O-methyl ether derivatives of robustaflavone have been found to be effective in a method for treating or preventing hepatitis B viral infections. Compositions which include these robustaflavone derivatives along with methods for preparing and using the same are also provided. These compositions may be used alone or in combination with at least one antiviral agent such as 3TC.

  本研究提供了实质上纯化的抗病毒双黄酮类物质--强力黄酮、桧黄酮、芒果黄酮、茄黄酮、伏肯黄酮、更萝黄酮、胡黄酮、琥珀黄酮、GB-1a 和 GB-2a。此外，还公开了抗病毒双黄烷衍生物及其盐形式，例如强力黄酮四硫酸钾盐，以及制备方法。还提供了包括抗病毒双黄酮类化合物、衍生物或其盐类的药物组合物，这些药物组合物可单独使用，也可与至少一种抗病毒药物如 3TC 结合使用。此外，还公开了一种从植物材料中获得高纯度强力黄酮的改进方法。本发明的双黄烷化合物、衍生物或其盐类可用于治疗和/或预防由病毒病原体引起的病毒感染，如流感，如甲型和乙型流感；肝炎，如乙型肝炎；人类免疫缺陷病毒，如HIV-1；疱疹病毒（HSV-1和HSV-2）；水痘带状疱疹病毒（VZV）；以及麻疹。例如，在治疗或预防乙型肝炎病毒感染的方法中，发现了半合成的六-O-乙酸酯和六-O-甲醚衍生物强力黄酮。此外，还提供了包括这些强力黄酮衍生物的组合物以及制备和使用这些组合物的方法。这些组合物可单独使用，也可与至少一种抗病毒药物如 3TC 结合使用。