(-)-二氢槲皮素 | 111003-33-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: (-)-二氢槲皮素
• 英文名称: (-)-taxifolin
• 英文别名: (2S,3S)-taxifolin；(2S,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• CAS: 111003-33-9
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: CXQWRCVTCMQVQX-CABCVRRESA-N

物化性质

• 熔点：
  232-234 °C(Solv: ethanol (64-17-5))
• 沸点：
  687.6±55.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

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

制备方法与用途

生物活性 (-)-_taxifolin 是 taxifolin 的低活性异构体。Taxifolin 具有显著的抗酪氨酸酶活性，并能有效抑制胶原酶（IC50 为 193.3 μM）。作为一种重要的天然化合物，Taxifolin 不仅具有抗纤维化作用，还能作为自由基清除剂，展现出强大的抗氧化能力。

反应信息

• 作为反应物：
  描述：

  (-)-二氢槲皮素 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：

  间苯三酚 在 盐酸 、 三氟甲磺酸酐 、 双氧水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 (-)-二氢槲皮素
  参考文献：
  名称：

  天然产物乌莫苷 A 和 (2R,3R)-Taxifolin-6-C-β-d-吡喃葡萄糖苷的全合成

  摘要：

  高极性ulmoside A 和(2R,3R)-taxifolin-6-C-β-d-吡喃葡萄糖苷的有效首次全合成已被描述，可用于预防代谢紊乱。合成的关键要素包括 Sc(OTf)3 催化的紫杉叶素上的区域选择性和立体选择性 C-糖苷化，产率为 35%，使用 d-葡萄糖和手性半制备反相高效液相色谱 (HPLC) 分离两者紫杉叶素和紫杉叶素-6-C-β-d-吡喃葡萄糖苷的非对映异构体混合物。合成 ulmoside A 及其非对映异构体与天然 ulmoside A 样品的分析数据的相关性证实了天然产物的指定绝对立体化学。

  DOI：

  10.1055/s-0040-1707971

文献信息

• Chemical Studies on the Mistletoe. IV. The Structure of Isoglucodistylin, a New Flavonoid Glycoside Isolated from<i>Taxillus kaempferi</i>
  作者：Atsushi Sakurai、Kyoji Okada、Yasuaki Okumura

  DOI：10.1246/bcsj.55.3051

  日期：1982.9

  A new flavonoid glycoside, isoglucodistylin was isolated from Taxillus kaempferi, and (2R,3S)-taxifolin 3-β-D-glucopyranoside was assigned to this substance from studies on the hydrolysis products and on the isomerization products, and from analyses of the carbon-13 NMR spectra.

  从紫杉中分离出一种新的类黄酮糖苷异葡糖二萜苷，并根据对水解产物和异构化产物的研究以及碳分析，将 (2R,3S)-紫杉叶素 3-β-D-吡喃葡萄糖苷指定给该物质-13 NMR谱。
• Cis- and trans-dihydroquercetin glucosides from needles of Pinus sylvestris
  作者：Lennart N. Lundgren、Olof Theander

  DOI：10.1016/0031-9422(88)84101-3

  日期：1988.1

  -glucopyranosides of (+)- trans -2,3-dihydroquercetin, dihydromyricetin and eriodictyol; (+)-catechin and (+)-gallocatechin have been isolated from the needles of Pinus sylvestris . The dihydroquercetin aglycones interconvert in methanolic solution. Two chemotypes of Pinus sylvestris can be distinguished on the basis of their dihydroquercetin, dihydromyricetin and eriodictyol contents.

  摘要 (-)- 顺式 -2,3-二氢槲皮素（推测为 3'- O -β- d -吡喃葡萄糖苷）；(+)-反式-2,3-二氢槲皮素、二氢杨梅素和圣草酚的3'-O-d-吡喃葡萄糖苷；(+)-儿茶素和(+)-没食子儿茶素已从樟子松的针叶中分离出来。二氢槲皮素苷元在甲醇溶液中相互转化。根据其二氢槲皮素、二氢杨梅素和圣草酚的含量，可以区分樟子松的两种化学型。
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• 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。
• Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship
  作者：Wen-Jun Jiang、Kan’ichiro Ishiuchi、Megumi Furukawa、Tomoko Takamiya、Susumu Kitanaka、Hiroshi Iijima

  DOI：10.1016/j.bmc.2015.09.042

  日期：2015.11

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.