6-C-[(E)-2-phenylethenyl]naringenin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-C-[(E)-2-phenylethenyl]naringenin
• 英文别名: 6-C-(E-phenylethenyl)naringenin
• 化学式: C₂₃H₁₈O₅
• 分子量: 374.393
• InChiKey: WBONVHMXTSZBAF-OJWOGGGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯乙醛 、 (S)-柚皮素 在 盐酸 、 水 作用下， 以 二乙二醇 为溶剂， 反应 2.0h， 以12.2 mg的产率得到8-C-[(E)-2-phenylethenyl]naringenin
  参考文献：
  名称：

  A phenylacetaldehyde–flavonoid adduct, 8-C-(E-phenylethenyl)-norartocarpetin, exhibits intrinsic apoptosis and MAPK pathways-related anticancer potential on HepG2, SMMC-7721 and QGY-7703

  摘要：

  Norartocarpetin, quercetin and naringenin were found to effectively inhibit 2-amino-1-methyl-6-pheny limidazo[4,5-b] pyridine (PhIP) formation through trapping its phenylacetaldehyde and form their adducts in roast beef patties. Six adducts [8-C- or 6-C-(E-phenylethenyl) flavonoids] formed between phenylacetaldehyde and three flavonoids were detected in roast beef patties by UPLC-MS analyses and compared with their synthetic references. These flavonoid-phenylacetaldehyde adducts were synthesised and further subjected to cytotoxicity tests on three liver cancer cell lines HepG2, SMMC-7721 and QGY-7703. The adduct 8-C-(E-phenylethenyl) norartocarpetin (NARA1) was found to significantly induce cancer cell death with IC50 values about 7 mu M. After pre-treating with MAPK and caspase inhibitors, alteration of the cell morphology and cleaved-PARP were detected in liver cancer cell lines administered with NARA1. These data indicated that norartocarpetin could inhibit PhIP formation in roast beef patties and form norartocarpetin-phenylacetaldehyde adducts. The adduct NARA1 has anticancer potential via intrinsic caspase-dependent and cell context-dependent MAPKs pathways. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2015.11.104

文献信息

• A phenylacetaldehyde–flavonoid adduct, 8-C-(E-phenylethenyl)-norartocarpetin, exhibits intrinsic apoptosis and MAPK pathways-related anticancer potential on HepG2, SMMC-7721 and QGY-7703
  作者：Zong-Ping Zheng、Yan Yan、Ji Xia、Shuang Zhang、Mingfu Wang、Jie Chen、Yang Xu

  DOI：10.1016/j.foodchem.2015.11.104

  日期：2016.4

  Norartocarpetin, quercetin and naringenin were found to effectively inhibit 2-amino-1-methyl-6-pheny limidazo[4,5-b] pyridine (PhIP) formation through trapping its phenylacetaldehyde and form their adducts in roast beef patties. Six adducts [8-C- or 6-C-(E-phenylethenyl) flavonoids] formed between phenylacetaldehyde and three flavonoids were detected in roast beef patties by UPLC-MS analyses and compared with their synthetic references. These flavonoid-phenylacetaldehyde adducts were synthesised and further subjected to cytotoxicity tests on three liver cancer cell lines HepG2, SMMC-7721 and QGY-7703. The adduct 8-C-(E-phenylethenyl) norartocarpetin (NARA1) was found to significantly induce cancer cell death with IC50 values about 7 mu M. After pre-treating with MAPK and caspase inhibitors, alteration of the cell morphology and cleaved-PARP were detected in liver cancer cell lines administered with NARA1. These data indicated that norartocarpetin could inhibit PhIP formation in roast beef patties and form norartocarpetin-phenylacetaldehyde adducts. The adduct NARA1 has anticancer potential via intrinsic caspase-dependent and cell context-dependent MAPKs pathways. (C) 2015 Elsevier Ltd. All rights reserved.