(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-(2-hydroxypropan-2-yl)-4-methoxy-7,8-dihydrofuro[2,3-g][1]benzofuran-3-one | 1427030-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-(2-hydroxypropan-2-yl)-4-methoxy-7,8-dihydrofuro[2,3-g][1]benzofuran-3-one
• CAS: 1427030-83-8
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: QYYRHQJYLLUVLG-APSNUPSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  黄腐酚 在 Aspergillus ochraceus AM₄₆₅ 作用下， 以 甲醇 为溶剂， 生成 (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-(2-hydroxypropan-2-yl)-4-methoxy-7,8-dihydrofuro[2,3-g][1]benzofuran-3-one 、 (2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone 、 (E)-2"-(2'''-hydroxy-2'''-propyl)-dihydrofurano[2",3":4',3']-2',4-dihydroxy-6'-methoxychalcone
  参考文献：
  名称：

  Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.01.026

文献信息

• 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.