3'-(3''-methyl-3''-hydroxybutyl)-2',4,4'-trihydroxy-6'-methoxychalcone | 688359-98-0

• 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: 3'-(3''-methyl-3''-hydroxybutyl)-2',4,4'-trihydroxy-6'-methoxychalcone
• 英文别名: xanthohumol H；(2E)-1-[2,4-dihydroxy-3-(3-hydroxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)-2-propen-1-one；(E)-1-[2,4-dihydroxy-3-(3-hydroxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 688359-98-0
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: HGZMVLUPBGGJMI-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  黄腐酚 在 recombinant Nectria haematococca kievitone hydratase 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3'-(3''-methyl-3''-hydroxybutyl)-2',4,4'-trihydroxy-6'-methoxychalcone
  参考文献：
  名称：

  重组表达，纯化，并从kievitone水合酶的生物化学表征Nectria haematococca

  摘要：

  基辅酮水合酶催化水加到植物异黄酮基酮的异戊二烯基部分的双键上，从而形成叔醇羟基-酮基。在自然界中，这种转化与真菌病原体抵抗宿主植物在感染后产生的植物抗毒素有关的防御机制有关。迄今为止，仅在茄镰刀菌（Fusarium solani f。）中鉴定并表征了编码酮酮水合酶活性的基因序列。sp。菜豆。在这里，我们报告了在Nectria haematococca（Nh KHS）中假定的基维酮水合酶序列的鉴定，F的胚形状态。solani，基于计算机软件序列分析。在甲基营养酵母巴斯德毕赤酵母中异源表达该酶后，我们已经确认了其酮异水合活性，并评估了其生化特性和底物特异性。纯化的重组Nh KHS显然是同型二聚糖蛋白。由于其对容易得到的查耳酮衍生物黄腐酚（XN）具有良好的活性，因此该化合物被选作生化研究的模型底物。水合酶活性的最佳pH和温度分别为6.0和35°C，XN水合的表观V max和K m值为7.16μmolmin

  DOI：

  10.1371/journal.pone.0192653

文献信息

• Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from <i>Humulus lupulus</i>
  作者：Susanne Vogel、Jörg Heilmann

  DOI：10.1021/np800188b

  日期：2008.7.1

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.
• 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.