(+)-epitaxifolin | 153666-25-2

• 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: (+)-epitaxifolin
• 英文别名: dihydroquercetin；(2S,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• CAS: 153666-25-2
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: CXQWRCVTCMQVQX-GJZGRUSLSA-N

物化性质

• 沸点：
  687.6±55.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-epitaxifolin 在 三甲基铵三氧化硫共聚物 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Discovery of novel sulfonated small molecules that inhibit vascular tube formation

  摘要：

  Tumor-associated angiogenesis is a complex process that involves the interplay among several molecular players such as cell-surface heparan sulfate proteoglycans, vascular endothelial growth factors and their cognate receptors. PI-88, a highly sulfonated oligosaccharide, has been shown to have potent anti-angiogenic activity and is currently in clinical trials. However, one of the major drawbacks of large oligosaccharides such as PI-88 is that their synthesis often requires numerous complex synthetic steps. In this study, several novel polysulfonated small molecule carbohydrate mimetics, which can easily be synthesized in fewer steps, are identified as promising inhibitors of angiogenesis in an in vitro tube formation assay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.014
• 作为产物：
  描述：

  花旗松素 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (+)-epitaxifolin
  参考文献：
  名称：

  Oxidative Transformation of Leucocyanidin by Anthocyanidin Synthase from Vitis vinifera Leads Only to Quercetin

  摘要：

  Anthocyanidin synthase from Vitis vinifera (VvANS) catalyzes the in vitro transformation of the natural isomer of leucocyanidin, 2R,3S,4S-cis-leucocyanidin, into 2R,4S-flavan-3,3,4-triol ([M + H](+), m/z 323) and quercetin. The C-3-hydroxylation product 2R,4S-flavan-3,3,4-triol is first produced and its C-3,C-4-dehydration product is in tautomeric equilibrium with (+)-dihydroquercetin. The latter undergoes a second VvANS-catalyzed C-3-hydroxylation leading to a 4-keto-2R-flavan-3,3-gem-diol which upon dehydration gives quercetin. The unnatural isomer of leucocyanidin, 2R,3S,4R-trans-leucocyanidin, is similarly transformed into quercetin upon C-3,C-4-dehydration, but unlike 3,4-cis-leucocyanidin, it also undergoes some C2,C-3-dehydration followed by an acid-catalyzed hydroxyl group extrusion at C-4 to give traces of cyanidin. Overall, the C-3,C-4-trans isomer of leucocyanidin is transformed into 2R,4R-flavan-3,3,4-triol (M + 1, m/z 323), (+)-DHQ, (-)-epiDHQ, quercetin, and traces of cyanidin. Our data bring the first direct observation of 3,4-cis-leucocyanidin- and 3,4-trans-leucocyanidin-derived 3,3-gem-diols, supporting the idea that the generic function of ANS is to catalyze the C-3-hydroxylation of its substrates. No cyanidin is produced with the natural cis isomer of leucocyanidin, and only traces with the unnatural trans isomer, which suggests that anthocyanidin synthase requires other substrate(s) for the in vivo formation of anthocyanidins.

  DOI：

  10.1021/acs.jafc.8b06968

文献信息

• Pharmaceutical combination comprising metformin and dihydroquercetin and its use for the treatment of cancer
  申请人：RESEARCH INSTITUTE FOR NUTRITION AND AGING CO., LTD.

  公开号：US10292962B2

  公开（公告）日：2019-05-21

  Provided is a novel medicament capable of reducing the side effects of metformin or a pharmaceutically acceptable salt thereof and useful as an anti-malignant tumor agent, in which metformin or a pharmaceutically acceptable salt thereof and dihydroquercetin or a pharmaceutically acceptable salt thereof are combined.

  本发明提供了一种能够减轻二甲双胍或其药学上可接受的盐的副作用并可用作抗恶性肿瘤药物的新型药物，其中二甲双胍或其药学上可接受的盐与二氢槲皮素或其药学上可接受的盐结合使用。
• Nonaka, Gen-Ichiro; Goto, Yuko; Kinjo, Jun-Ei, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 3, p. 1105 - 1108
  作者：Nonaka, Gen-Ichiro、Goto, Yuko、Kinjo, Jun-Ei、Nohara, Toshihiro、Nishioka, Itsuo

  DOI：——

  日期：——
• PHARMACEUTICAL COMBINATION COMPRISING METFORMIN AND DIHYDROQUERCETIN AND ITS USE FOR THE TREATMENT OF CANCER
  申请人：Research Institute for Nutrition and Aging Co., Ltd.

  公开号：EP3003296B1

  公开（公告）日：2018-10-10
• US9808440B2
  申请人：——

  公开号：US9808440B2

  公开（公告）日：2017-11-07
• Discovery of novel sulfonated small molecules that inhibit vascular tube formation
  作者：Karthik Raman、Rajesh Karuturi、Vimal P. Swarup、Umesh R. Desai、Balagurunathan Kuberan

  DOI：10.1016/j.bmcl.2012.04.014

  日期：2012.7

  Tumor-associated angiogenesis is a complex process that involves the interplay among several molecular players such as cell-surface heparan sulfate proteoglycans, vascular endothelial growth factors and their cognate receptors. PI-88, a highly sulfonated oligosaccharide, has been shown to have potent anti-angiogenic activity and is currently in clinical trials. However, one of the major drawbacks of large oligosaccharides such as PI-88 is that their synthesis often requires numerous complex synthetic steps. In this study, several novel polysulfonated small molecule carbohydrate mimetics, which can easily be synthesized in fewer steps, are identified as promising inhibitors of angiogenesis in an in vitro tube formation assay. (C) 2012 Elsevier Ltd. All rights reserved.