Lupalbigenin; 5,7,4'-三羟基-6,3'-二异戊烯基异黄酮 | 76754-24-0

• 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 - 异黄酮类化合物
• 中文名称: Lupalbigenin; 5,7,4'-三羟基-6,3'-二异戊烯基异黄酮
• 中文别名: Lupalbigenin;5,7,4'-三羟基-6,3'-二异戊烯基异黄酮；5,7,4'-三羟基-6,3'-二异戊烯基异黄酮
• 英文名称: 5,7,4'-trihydroxy-6,3'-diprenylisoflavone
• 英文别名: 6,3'-di(dimethylallyl)genistein；lupalbigenin；5,7-dihydroxy-3-[4-hydroxy-3-(3-methyl-but-2-enyl)-phenyl]-6-(3-methyl-but-2-enyl)-chromen-4-one；5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6-(3-methylbut-2-enyl)chromen-4-one
• CAS: 76754-24-0
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: HTAZIHDXIUPDQP-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C(Solv: toluene (108-88-3); ethyl acetate (141-78-6))
• 沸点：
  623.6±55.0 °C(Predicted)
• 密度：
  1.246±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)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

lupabigenin 是一种具有抗转移和促凋亡作用的天然化合物。

反应信息

• 作为反应物：
  描述：

  Lupalbigenin; 5,7,4'-三羟基-6,3'-二异戊烯基异黄酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 2.0h， 以25 mg的产率得到ulexin B
  参考文献：
  名称：

  新异黄酮和异戊二烯化二氢黄酮醇来自鸡血藤

  摘要：

  Millettia pachycarpa Benth的摘要提取。得到 5,7,4'-trihydroxy-6,8-diprenylisoflavone (1a), 5,7,4'-trihydroxy-6,3'-diprenylisoflavone (2a), 5,7,3',4'-tetrahydroxy- 6,8-diprenylisoflavone (3a) and (2R, 3R)-5,4'-dihydroxy-8-prenyl-6″,6″-dimethylpyrano[2″,3″: 7,6]-dihydroflavonol (4a)结构是通过化学转化和光谱方法建立的。Pectolinarigenin 和 Salvigenin 是从 Buddleia macrostachya Benth 中分离出来的。

  DOI：

  10.1016/0031-9422(80)85140-5
• 作为产物：
  描述：

  3-甲基丁-2-烯基膦酰磷酸氢酯 、 染料木素 在 Aspergillus terreus aromatic prenyltransferase 作用下， 生成 Lupalbigenin; 5,7,4'-三羟基-6,3'-二异戊烯基异黄酮
  参考文献：
  名称：

  对芳香异戊二烯基转移酶的酶混杂的分子认识

  摘要：

  芳香异戊二烯基转移酶（aPTase）将异戊二烯供体中的异戊二烯基团转移到各种芳族受体上，其中一些对多种异戊二烯基供体和多种受体都具有极强的酶促混杂特性。在这项研究中，我们从土曲霉中发现了一种新的aPTase，AtaPT对各种芳香族受体和异戊二烯供体表现出前所未有的混杂性，并且还可以产生具有各种异戊二烯化模式的产品。系统的晶体学研究揭示了具有供体依赖性受体特异性的配体结合的各种离散构象以及在宽敞的疏水性底物结合口袋中的多个结合位点。在底物结合口袋处的活性位点的进一步结构引导的诱变负责改变对底物的特异性和混杂性以及产物烯丙基化的多样性。我们的研究揭示了AtaPT混杂的分子机制，并提出了一种有效的蛋白质工程策略，可在药物开发应用中产生新的异戊二烯衍生物。

  DOI：

  10.1038/nchembio.2263

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures
  作者：Hirobumi Yamamoto、Masayuki Senda、Kenichiro Inoue

  DOI：10.1016/s0031-9422(00)00198-9

  日期：2000.8

  Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K-m values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 mu M, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cyclodehydrogenation of -(3,3-dimethylallyl)phenols with trityl tetrafluoroborate
  作者：P Barua、NC Barua、Rp Sharma

  DOI：10.1016/s0040-4039(00)94205-9

  日期：1983.1
• Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases
  作者：Kang Zhou、Xia Yu、Xiulan Xie、Shu-Ming Li

  DOI：10.1021/acs.jnatprod.5b00422

  日期：2015.9.25

  Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).