8-C-[(E)-2-phenylethenyl]quercetin

• 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: 8-C-[(E)-2-phenylethenyl]quercetin
• 英文别名: 8-C-(E-phenylethenyl)qucercetin；8-C-(E-phenylethenyl)quercetin；2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(E)-2-phenylethenyl]chromen-4-one
• 化学式: C₂₃H₁₆O₇
• 分子量: 404.376
• InChiKey: ZKAQIOGLBIZIAM-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  槲皮素 、 苯乙醛 在 盐酸 作用下， 以 水 、 二乙二醇 为溶剂， 反应 2.0h， 生成 8-C-[(E)-2-phenylethenyl]quercetin 、 8-C-(E-phenylethenyl)norartocarpetin
  参考文献：
  名称：

  具有肝癌细胞抑制活性的黄酮类衍生物及其合 成与应用

  摘要：

  本发明公开了具有肝癌细胞抑制活性的黄酮类衍生物及其合成与应用，属于生物医药技术领域。本发明以苯乙醛和黄酮类物质经过加合反应，得到了四种具有肝癌细胞抑制活性的黄酮类衍生物8-C-(E-phenylethenyl)qucercetin、6-C-(E-phenylethenyl)qucercetin、8-C-(E-phenylethenyl)norartocarpetin、和8-C-(E-phenylethenyl)norartocarpetin，是将苯乙醛与黄酮类母体溶解在二乙二醇溶液中，在盐酸催化下于130℃加热反应2小时，然后通过萃取、凝胶柱层析所得，并进行结构鉴定。本发明提供的四种黄酮类衍生物具有较强的肝癌细胞抑制活性，能够制备有效用于肝癌的各种制剂。

  公开号：

  CN104370869B

文献信息

• Compositions and methods for lightening skin and reducing hyperpigmentation
  申请人：Versitech Limited

  公开号：US10973748B2

  公开（公告）日：2021-04-13

  The composition includes a cyclic, unsaturated compound, preferably a polyphenol derivative. It reduces the synthesis of melanin by inhibiting the activity and expression levels of tyrosinase and related proteins, thereby preventing and limiting the content and distribution of melanin in mammalian skin. It also induces autophagy of melanosome, thereby restricting the synthesis, storage and transfer of melanin from melanocyte to keratinocyte. The dual modes of action allow for the efficacy of the composition at low dosage without causing toxicity to lighten skin and treat disorders associated with hyperpigmentation.

  该组合物包括一种环状不饱和化合物，最好是一种多酚衍生物。它通过抑制酪氨酸酶和相关蛋白的活性和表达水平来减少黑色素的合成，从而防止和限制哺乳动物皮肤中黑色素的含量和分布。它还能诱导黑色素体的自噬，从而限制黑色素的合成、储存以及从黑色素细胞向角质细胞的转移。双重作用模式使该成分在低剂量下就能发挥功效，且不会产生毒性，从而达到美白皮肤和治疗色素沉着相关疾病的目的。
• 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.
• COMPOSITIONS AND METHODS FOR LIGHTENING SKIN AND REDUCING HYPERPIGMENTATION
  申请人：Versitech Limited

  公开号：US20190133907A1

  公开（公告）日：2019-05-09

  The composition includes a cyclic, unsaturated compound, preferably a polyphenol derivative. It reduces the synthesis of melanin by inhibiting the activity and expression levels of tyrosinase and related proteins, thereby preventing and limiting the content and distribution of melanin in mammalian skin. It also induces autophagy of melanosome, thereby restricting the synthesis, storage and transfer of melanin from melanocyte to keratinocyte. The dual modes of action allow for the efficacy of the composition at low dosage without causing toxicity to lighten skin and treat disorders associated with hyperpigmentation.