Tetrahydroxanthohumol | 96169-02-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Tetrahydroxanthohumol
• 英文别名: 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbutyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• CAS: 96169-02-7
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: RNYWSIACWNMMEO-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  570.0±29.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tetrahydroxanthohumol 生成 1-[2-hydroxy-3-isopentyl-6-methoxy-4-(4-nitro-benzoyloxy)-phenyl]-3-[4-(4-nitro-benzoyloxy)-phenyl]-propan-1-one
  参考文献：
  名称：

  Verzele et al., Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 452,467

  摘要：

  DOI：
• 作为产物：
  描述：

  黄腐酚 在 palladium on activated charcoal 氢气 作用下， 生成 Tetrahydroxanthohumol
  参考文献：
  名称：

  异戊烯化和非异戊烯二酰查耳酮和黄烷酮的体外抗氧化和抗氧化作用。

  摘要：

  对啤酒花和啤酒中发现的异戊烯基黄酮类化合物，即异戊二烯酮和异戊烯醇酮类，抑制其体外抑制人低密度脂蛋白（LDL）氧化的能力。LDL的氧化通过共轭二烯和硫代巴比妥酸反应性物质（TBARS）的形成以及色氨酸荧光的损失来评估。在5和25 microM的浓度下，所有测试的炔丙基苯甲醚均抑制了2 microM硫酸铜诱导的LDL（50 microg蛋白/ ml）的氧化。在5和25 microM时，炔戊烯酮的抗氧化活性均低于戊烯酮。在25 microM时，基于TBARS的形成，非炔丙基化的查尔酮，查尔萘丁酮（CN）和非炔丙基化的黄烷酮，柚皮素（NG）对LDL氧化产生了促氧化剂作用。黄腐酚（XN），啤酒花和啤酒中的主要异戊二烯查尔酮在抑制LDL氧化方面表现出高抗氧化活性，高于α-生育酚和异黄酮染料木黄酮，但低于黄酮醇槲皮素。结合使用时，XN和α-生育酚完全抑制铜介导的LDL氧化。这些发现表明，在啤酒花和啤酒

  DOI：

  10.1021/jf0002995

文献信息

• XANTHOHUMOL-BASED COMPOUNDS AND COMPOSITIONS THEREOF, AND METHODS OF MAKING AND USING THE SAME
  申请人：Oregon State University

  公开号：US20160008298A1

  公开（公告）日：2016-01-14

  Disclosed herein are compounds capable of ameliorating, treating, and preventing metabolic syndrome, or risk factors associated with metabolic syndrome, such as obesity, diabetes, and/or cardiovascular disease. In some embodiments, the compounds can function as mild mitochondrial uncouplers and thereby reduce markers of metabolic syndrome by improving insulin sensitivity and glucose metabolism. Methods of making the compounds also are disclosed herein, along with compositions and formulations suitable for administration to a subject. In some embodiments, the compounds (or compositions thereof) can be formulated and administered as dietary supplements.

  本文披露了一些能够改善、治疗和预防代谢综合征或与代谢综合征相关的危险因素，如肥胖、糖尿病和/或心血管疾病的化合物。在某些实施例中，这些化合物可以作为轻度线粒体解偶联剂发挥作用，从而通过改善胰岛素敏感性和葡萄糖代谢来减少代谢综合征的标志。本文还披露了制备这些化合物的方法，以及适合用于给予受试者的组合物和配方。在某些实施例中，这些化合物（或其组合物）可以制成膳食补充剂的形式进行配方和给予。
• Orth,W.A.; Riedl,W., Justus Liebigs Annalen der Chemie, 1963, vol. 663, p. 74 - 82
  作者：Orth,W.A.、Riedl,W.

  DOI：——

  日期：——
• Xanthohumol, a Polyphenol Chalcone Present in Hops, Activating Nrf2 Enzymes To Confer Protection against Oxidative Damage in PC12 Cells
  作者：Juan Yao、Baoxin Zhang、Chunpo Ge、Shoujiao Peng、Jianguo Fang

  DOI：10.1021/jf505075n

  日期：2015.2.11

  Xanthohumol (2',4',4-trihydroxy-6'-methoxy-3'-prenylchalcone, Xn), a polyphenol chalcone from hops (Humulus lupulus), has received increasing attention due to its multiple pharmacological activities. As an active component in beers, its presence has been suggested to be linked to the epidemiological observation of the beneficial effect of regular beer drinking. In this work, we synthesized Xn with a total yield of 5.0% in seven steps and studied its neuroprotective function against oxidative-stress-induced neuronal cell damage in the neuronlike rat pheochromocytoma cell line PC12. Xn displays moderate free-radical-scavenging capacity in vitro. More importantly, pretreatment of PC12 cells with Xn at submicromolar concentrations significantly upregulates a panel of phase II cytoprotective genes as well as the corresponding gene products, such as glutathione, heme oxygenase, NAD(P)H:quinone oxidoreductase, thioredoxin, and thioredoxin reductase. A mechanistic study indicates that the alpha,beta-unsaturated ketone structure in Xn and activation of the transcription factor Nrf2 are key determinants for the cytoprotection of Xn. Targeting the Nrf2 by Xn discloses a previously unrecognized mechanism underlying the biological action of Xn. Our results demonstrate that Xn is a novel small-molecule activator of Nrf2 in neuronal cells and suggest that Xn might be a potential candidate for the prevention of neurodegenerative disorders.