α,β-dihydroxanthohumol | 102448-00-0

• 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: α,β-dihydroxanthohumol
• 英文别名: dihydroxanthohumol；3'-(3,3-dimethylallyl)-4,2',4'-trihydroxy-6'-methoxy-α,β-dihydrochalcone；1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propan-1-one；1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propan-1-on；alpha,beta-Dihydroxanthohumol；1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• CAS: 102448-00-0
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: SVTCZHIDEDUTBH-UHFFFAOYSA-N

物化性质

• 熔点：
  132 - 135oC
• 沸点：
  577.4±39.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 储存条件：
  -20°C，无氧环境，光敏

反应信息

• 作为产物：
  描述：

  黄腐酚 在 5%-palladium/activated carbon 、 氢气 作用下， 生成 α,β-dihydroxanthohumol
  参考文献：
  名称：

  The Effect of Xanthohumol Derivatives on Apoptosis Induction in Canine Lymphoma and Leukemia Cell Lines

  摘要：

  黄腐醇是一种癌症化学预防剂，可通过多种抑制机制干扰癌变的发生、促进和发展阶段。据报道，黄腐醇是一种对白血病/淋巴瘤细胞有效的药物。在本研究中，我们研究了黄腐醇及其天然和半合成衍生物对各种犬白血病/淋巴瘤细胞系的作用。黄腐醇、三种啤酒花次要前黄酮类化合物（黄腐醇 C、黄腐醇 D、α,β-二羟基黄腐醇）以及通过生物转化和化学修饰获得的四种衍生物（黄腐醇 4′-O-β-D-（4‴-O-甲基）-吡喃葡萄糖苷）（1″、2″-二羟基黄腐醇 K、2,3-脱氢异黄腐醇、(Z)-6,4′-二羟基-4-甲氧基-7-异戊烯基茅酮）对以下犬白血病/淋巴瘤细胞系进行了抗增殖和促凋亡活性测试：CLBL-1（B 细胞淋巴瘤）、CLB70（B 细胞白血病）和 GL-1（B 细胞白血病）。在 0.1-30 µM 的最终浓度范围内对化合物进行了 48 小时的测试。所测试的 8 种黄酮类化合物都对选定的犬淋巴瘤/白血病细胞系产生了浓度依赖性细胞毒性。三种化合物显著降低了所有细胞系的存活率，IC50 在 0.5 至 8 μM 之间。用 AnnexinV 和碘化丙啶对处理过的细胞进行双重染色显示，死亡细胞大多处于凋亡晚期。检测到了 ROS 的产生和线粒体电位的变化。Western 印迹分析显示 Bcl-2 的表达减少。犬淋巴瘤和白血病细胞系对黄腐醇衍生物敏感，这些化合物通过细胞凋亡机制发挥作用。这些化合物无论是单独使用还是与其他疗法结合使用，都可能有助于犬白血病/淋巴瘤的治疗。

  DOI：

  10.3390/ijms241411724

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• 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。
• Verzele et al., Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 452,467
  作者：Verzele et al.

  DOI：——

  日期：——
• Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro
  作者：Tomasz Tronina、Agnieszka Bartmańska、Beata Filip-Psurska、Joanna Wietrzyk、Jarosław Popłoński、Ewa Huszcza

  DOI：10.1016/j.bmc.2013.01.026

  日期：2013.4

  Xanthohumol (1) and xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution. Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures were established on the basis of their spectral data. One of them: 2 ''-(2'''-hydroxyisopropyl)-dihydrofurano-[4 '',5 '':3',4']-4',2-dihydroxy-6'-methoxy-alpha,beta-dihydrochalcone (6) has not been previously reported in the literature. The antioxidant properties of hops flavonoids and xanthohumol derivatives were investigated using the 2,2'-diplienyl-1-picrylhydrazyl (DPPH) radical scavenging method. The effects of these compounds on proliferation of MCF-7, PC-3 and HT-29 human cancer cell lines were determined by the SRB assay. With the exception of one metabolite, all tested compounds showed antiproliferative activity against the tested human cancer lines. alpha,beta-Dihydroxanthohumol (4), obtained through the biotransformation of xanthohumol, showed higher antiproliferative activity against MCF-7 human breast carcinoma cell line than cisplatin, a widely used anticancer therapeutic agent, and a comparably high activity against PC-3 human prostate cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.
• PRENYLATED CHALCONE FORMULATION FOR THE TREATMENT OF BEES
  申请人：BIOACTIVE-TECH SP. Z O.O.

  公开号：US20150283098A1

  公开（公告）日：2015-10-08

  The invention provides a formulation preventing the collapse of insects of Apidae family, especially bees and bumblebees, especially as a result of a syndrome specified as CCD (Colony Collapse Disorder) and the use thereof. Moreover, the formulation increases vigour in a bee colony. The invention belongs to the field of apiary and protection of environment from negative effects of using insecticides in agriculture and fruit culture.