洋槐黄素 | 490-31-3

• 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: 洋槐黄素
• 英文名称: robinetin
• 英文别名: 3,7,3',4',5'-pentahydroxyflavone；3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 490-31-3
• 化学式: C₁₅H₁₀O₇
• 分子量: 302.24
• InChiKey: SOEDEYVDCDYMMH-UHFFFAOYSA-N

物化性质

• 熔点：
  326-328°C
• 沸点：
  363.28°C (rough estimate)
• 密度：
  1.3616 (rough estimate)
• 溶解度：
  DMSO（微溶）、甲醇（微溶，加热）
• LogP：
  2.550 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 安全说明：
  S22,S45
• 危险类别码：
  R22
• 危险品运输编号：
  UN 2811
• 海关编码：
  2932999099
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

制备方法与用途

生物活性

罗比汀（3,3',4',5',7-五羟基黄酮）是一种天然黄酮，具有显著的“两种颜色”固有荧光特性，并展现出抗真菌、抗病毒、抗菌、抗突变和抗氧化活性。此外，它还能抑制脂质过氧化和蛋白质糖基化。

体外研究

罗比汀在不同浓度下表现出对HIV整合酶切割和集成的剂量依赖性抑制作用（0.1-10 μM；1小时）。它能够抑制普罗塔斯·凡瓦尔斯基（Proteus vulgaris）中的DNA合成以及金黄色葡萄球菌（S. aureus）中的RNA合成。在较高浓度（100-200 μM 或 25 μM；1小时或72小时），罗比汀高效地抑制了蛋黄卵磷脂膜（EYPC）的脂质过氧化和血红蛋白A（HbA）的糖基化。

此外，罗比汀在激发态表现出内分子质子转移现象，导致其具有“两种颜色”（蓝紫色和黄绿色区域）的荧光特征。这两种颜色的比例受到荧光物质局部环境的影响而显著变化。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3,7-二羟基-3',4',5'-三甲氧基黄酮	3',4',5'-O-trimethylrobinetin	132594-09-3	C18H16O7	344.321
  ——	3-hydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one	——	C19H18O7	358.348
  ——	3,7,3'-trimethoxy-4',5'-dihydroxyflavone	223902-81-6	C18H16O7	344.321
  ——	7-hydroxy-3-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one	20979-43-5	C19H18O7	358.348
  ——	7-benzyloxy-3-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one	354119-95-2	C25H22O7	434.445

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3,7,3',4',5'-pentamethoxyflavone	19056-76-9	C20H20O7	372.375

反应信息

• 作为反应物：
  描述：

  洋槐黄素 在 1,1-二苯-2-苦基肼 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Kinetic Study of Flavonoid Reactions with Stable Radicals

  摘要：

  The antiradical activities of some flavonols (kaempferol, quercetin, robinetin, quercetagetin, and myricetin), flavones (apigenin, baicalein, and luteolin), flavanones (naringenin and dihydroquercetin), and flavanols [(+)-catechin and (-)-epicatechin] were determined by measuring the reaction kinetics with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and alpha,gamma-bisdiphenylene-beta-phenylallyl (BDPA) radicals. The reactions, which follow the mixed second-order rate law, were investigated under pseudo-first-order conditions by use of a large excess of flavonoids, and their stoichiometry was determined by spectrophotometric titration. The results confirm stoichiometric factors of 1, 2, and 3 for flavonoids with one, two, and three hydroxyl groups in the B-ring, respectively, excluding kaempferol, which, despite a single OH group in the B-ring, has a factor of 2, which is explained by the 3-OH group supporting the reaction with free radicals. Structure- activity considerations indicate for the present series of flavonoids the importance of multiple OH substitutions and conjugation. The logarithms of reaction rate constants with the OH, DPPH, and BDPA radicals correlate well with the reduction potential of the flavonoids.

  DOI：

  10.1021/jf049880h
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-甲氧基-1-乙酮 在 氢碘酸 、 乙酸酐 、 sodium 3,4,5-trimethoxybenzoate 作用下， 生成 洋槐黄素
  参考文献：
  名称：

  73.花青素。第十三部分。刺槐（Robinia pseudacacia）色素的合成

  摘要：

  DOI：

  10.1039/jr9330000268

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• [EN] SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS<br/>[FR] ANALOGUES D'URÉE PONTÉS SUBSTITUÉS EN TANT QUE MODULATEURS DE SIRTUINE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2016079709A1

  公开（公告）日：2016-05-26

  The present invention relates to novel substituted bridged urea analog compounds of Formula (I) or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds, alone or in combination with other therapeutic agents, as Sirtuin Modulators useful for increasing lifespan of a cell, and for use in treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity.

  本发明涉及一种新型的取代桥式脲类似物化合物，其化学式为（I）或其药学上可接受的盐，相应的药物组合物，制备这种化合物的方法以及单独使用或与其他治疗剂联合使用的这些化合物作为Sirtuin调节剂，可用于增加细胞寿命，并用于治疗和/或预防各种疾病和紊乱，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块紊乱、炎症、癌症和/或潮红有关的疾病或紊乱，以及那些会受益于增加线粒体活性的疾病或紊乱。
• [EN] AMIDE DERIVATIVES AS SIRTUIN MODULATORS<br/>[FR] DÉRIVÉS D'AMIDE COMME MODULATEURS DE SIRTUINES
  申请人：SIRTRIS PHARMACEUTICALS INC

  公开号：WO2009058348A1

  公开（公告）日：2009-05-07

  Provided herein are novel sirtuin-modulating compounds represented by Structural Formula (I) and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin- modulating compound in combination with another therapeutic agent.

  提供的是由结构公式（I）表示的新的sirtuin调节化合物及其用途。sirtuin调节化合物可用于延长细胞寿命，以及治疗和/或预防多种疾病和紊乱，例如与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、凝血障碍、炎症、癌症和/或潮红相关的疾病或紊乱，以及将从增加线粒体活性中受益的疾病或紊乱。还提供了包含sirtuin调节化合物与另一种治疗剂的组合的药物组合物。
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• STABILIZATION OF HYDROXYLAMINE CONTAINING SOLUTIONS AND METHOD FOR THEIR PREPARATION
  申请人：Lee Wai Mun

  公开号：US20090112024A1

  公开（公告）日：2009-04-30

  The invention relates to the use of amidoximes for prevention of or stabilization of hydroxylamine compounds against undesired decomposition.

  本发明涉及将酰胺肟用于预防或稳定羟基胺化合物，防止其不受控分解。