漆黄素 ( 紫铆素) | 492-14-8

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 漆黄素 ( 紫铆素)
• 中文别名: 漆黄素(紫铆素)；(S)-7,3',4'-三羟基黄酮
• 英文名称: butin
• 英文别名: 3',4',7-trihydroxyflavanone；(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrochromen-4-one
• CAS: 492-14-8
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: MJBPUQUGJNAPAZ-AWEZNQCLSA-N

物化性质

• 熔点：
  224-226℃
• 沸点：
  582.4±50.0 °C(Predicted)
• 密度：
  1.485
• 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)：
  1.8
• 重原子数：
  20
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

(-)-Butin 是Butin 的S对映体。这种化合物主要从黄檀心材中提取，是一种具有强抗氧化、抗血小板聚集以及抗炎活性的生物活性黄酮类化合物。

反应信息

• 作为反应物：
  描述：

  漆黄素 ( 紫铆素) 在 NADPH disodium salt 、 口服葡萄糖 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 3',4',7-三羟基异黄酮
  参考文献：
  名称：

  A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity

  摘要：

  Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ER alpha and ER beta) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.

  DOI：

  10.1016/j.chembiol.2010.03.010
• 作为产物：
  描述：

  rhusopolyphenol F 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到漆黄素 ( 紫铆素)
  参考文献：
  名称：

  Polyphenols from the bark of Rhus verniciflua and their biological evaluation on antitumor and anti-inflammatory activities

  摘要：

  Bioassay-guided fractionation and chemical investigation of the extract of Rhus verniciflua bark resulted in the identification of six polyphenols, rhusopolyphenols A-F (1-6), together with four known compounds including (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano[3,4-c]-2-benzopyran-1-one (7), peapolyphenol C (8), cilicione-b (9) and (alpha R)-alpha,3,4,2',4'-pentahydroxydihydrochalcone (10). The structures of these polyphenols were elucidated by spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, and their absolute configurations were further confirmed by a combination of chemical methods and CD data analysis. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15), and compounds 4-6, 9 and 10 showed antiproliferative activity against the tested cells, with IC50 values of 3.31-18.51 mu M. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, the anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium of murine microglia BV-2 cells. Compounds 5 and 10 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells with IC50 values of 28.90 and 12.70 mu M, respectively. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.05.005

文献信息

• Diarylalkanes as potent inhibitors of binuclear enzymes
  申请人：Jia Qi

  公开号：US20050267047A1

  公开（公告）日：2005-12-01

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重复过程相结合，以识别活性植物提取物和特定化合物——二芳基烷烃和/或二芳基醇，这些化合物特异性地抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，并防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，以及一种预防和治疗与双核酶功能相关的疾病和病况的方法。本发明还包括一种预防和治疗黑色素过度产生以及与之相关的皮肤疾病和病况的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病况的方法包括向需要的宿主施用由一种或多种植物合成和/或分离的一种或多种二芳基烷烃和/或二芳基醇组成的组合物的有效量，以及药用载体。
• [DE] STERISCH ANSPRUCHSVOLLE CHELATPHOSPHINITPHOSPHITLIGANDEN, KATALYSATOR, UMFASSEND WENIGSTENS EINEN NICKEL (0) KOMPLEX STABILISIERT DURCH DIESEN LIGANDEN SOWIE EIN VERFAHREN ZUR HERSTELLUNG VON NITRILEN<br/>[EN] STERICALLY HINDERED CHELATE PHOSPHINITE-PHOSPHITE LIGAND, CATALYST, COMPRISING AT LEAST ONE NICKEL(0) COMPLEX STABILIZED BY SAID LIGAND AND METHOD FOR PRODUCTION OF NITRILES<br/>[FR] LIGAND PHOSPHITE-PHOSPHINITE CHELATE A ENCOMBREMENT STERIQUE, CATALYSEUR COMPRENANT AU MOINS UN COMPLEXE DE NICKEL (0) STABILISE PAR CE LIGAND ET PROCEDE DE PRODUCTION DE NITRILES
  申请人：BASF AG

  公开号：WO2005042547A1

  公开（公告）日：2005-05-12

  Beschrieben werden Phosphinitphosphite I der Formel 1 oder 2 oder 3 oder 4 oder 5 oder 6 mit R1, R2, R4 sind unabhängig voneinander eine Alkyl- oder Alkylengruppe mit 1 bis 8 Kohlenstoffatomen, mit der Maßgabe, dass mindestens eine der Gruppen R1, R2, R4 ungleich H ist, R5 bis R22 sind unabhängig voneinander H, eine Alkyl- oder Alkylengruppe mit 1 bis 8 Kohlenstoffatomen, R3 ist H, Methyl oder Ethyl, X ist F, Cl oder CF3, wenn n gleich 1 oder 2 ist, X ist H, wenn n gleich 0 ist. und deren Gemische.

  描述的是具有1、2、3、4、5或6式的磷氧化物磷酸脂I，其中R1、R2、R4分别独立地是含有1至8个碳原子的烷基或烷基烯基，但至少其中一个R1、R2、R4不等于H；R5至R22分别独立地是H、含有1至8个碳原子的烷基或烷基烯基；R3是H、甲基或乙基；X是F、Cl或CF3，当n等于1或2时，X是H，当n等于0时，以及它们的混合物。
• Photochemical deoxygenation of an α-ketol: the dihydroflavonol–flavanone conversion
  作者：Jan H. van der Westhuizen、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19800001003

  日期：——

  to free phenolic flavanone analogues with complete retention of configuration at C(2). Similarly their methyl ethers give the corresponding flavanones and flavones. The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.

  在无水乙酸乙酯中辐照光学纯的2,3-反-3-羟基黄酮类化合物直接导致游离酚类黄烷酮类似物的完全保留在C（2）的配置。类似地，它们的甲基醚得到相应的黄烷酮和黄酮。该反应代表在Clemmensen条件下还原的光化学当量。
• [DE] NEUE PYRIMIDIN-4,6-DICARBONSÄUREDIAMIDE ZUR SELEKTIVEN INHIBIERUNG VON KOLLAGENASEN<br/>[EN] NOVEL PYRIMIDINE-4,6-DICARBOXAMIDES FOR THE SELECTIVE INHIBITION OF COLLAGENASES<br/>[FR] NOUVEAUX DIAMIDES D'ACIDE PYRIMIDINE-4,6-DICARBOXYLIQUE POUR L'INHIBITION SELECTIVE DE COLLAGENASES
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2004041788A1

  公开（公告）日：2004-05-21

  Pyrimidin-4.6-dicarbonsäurediamide der Formel (I), eignen sich zur selektiven Inhibition der Kollagenase (MMP 13). Die Pyrimidin-4,6-dicarbonsäurediamide können daher zur Behandlung degenerativer Gelenkerkrankungen eingesetzt werden.

  式(I)的嘧啶-4,6-二羧酰二胺适用于选择性抑制胶原酶(MMP 13)。因此，嘧啶-4,6-二羧酰二胺可用于治疗退行性关节疾病。
• [EN] COMPOUNDS AND METHODS FOR TREATING CANCER<br/>[FR] COMPOSÉS ET PROCÉDÉS DE TRAITEMENT DU CANCER
  申请人：SHARE GAL RES AND DEVELOPMENT LTD

  公开号：WO2019111265A1

  公开（公告）日：2019-06-13

  The present invention relates to novel compounds, compositions and methods of preparation thereof, as well as uses thereof for treating cancer of various types, including: pancreatic, liver, breast, colon, brain and lung cancer.

  本发明涉及新颖化合物、组合物及其制备方法，以及用于治疗各种类型癌症的用途，包括：胰腺癌、肝癌、乳腺癌、结肠癌、脑癌和肺癌。