5-methoxy-6-O-β-D-glucopyranosyl-7-phenyl-3H-benzo[de]isochromen-1-one | 1159493-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxy-6-O-β-D-glucopyranosyl-7-phenyl-3H-benzo[de]isochromen-1-one
• 英文别名: 5-methoxy-7-phenyl-6-(3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)benzo[de]isochromen-1(3H)-one；haemodorose；7-methoxy-10-phenyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-2-one
• CAS: 1159493-99-8
• 化学式: C₂₅H₂₄O₉
• 分子量: 468.46
• InChiKey: PZTAHEJWBGPZLJ-FHBCLOHASA-N

物化性质

• 沸点：
  765.5±60.0 °C(predicted)
• 密度：
  1.479±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-methoxy-6-O-β-D-glucopyranosyl-7-phenyl-3H-benzo[de]isochromen-1-one 在 盐酸 、 水 作用下， 反应 6.0h， 生成 可得然胶
  参考文献：
  名称：

  Phenylphenalenones from the Australian Plant Haemodorum simplex

  摘要：

  Chemical investigation of the Australian plant Haemodortun simplex resulted in the isolation of three new phenylphenalenones, haemodorone (10), haemodorol (11), and haemodorose (12), together with the previously reported compounds 5, dilatrin (6), and xiphidone (8). The first complete 2D NMR characterization for all of the compounds isolated, including several chemical shift reassignments for dilatrin (6), is reported. In addition this is one of the few reports to discuss the isolation of new phenylphenalenones from an Australian medicinal plant. The crude extract of both the bulbaceous and aerial components of the plant exhibited varying degrees of antibacterial, antifungal, and antiviral activity, and only the bulbs displayed potent cytotoxic activity.

  DOI：

  10.1021/np900016h

文献信息

• Precursor-Directed Biosynthesis of Phenylbenzoisoquinolindione Alkaloids and the Discovery of a Phenylphenalenone-Based Plant Defense Mechanism
  作者：Yu Chen、Christian Paetz、Bernd Schneider

  DOI：10.1021/acs.jnatprod.7b00885

  日期：2018.4.27

  reactions under oxidative or inert conditions, respectively, to elucidate the entire pathway from phenylbenzoisochromenones to phenylbenzoisoquinolindiones. An intermediate in this pathway, a reactive hydroxylactone/aldehyde, readily binds not only to amines in vitro but may also bind to the N-terminus of biogenic peptides and proteins of herbivores and pathogens in vivo. The deactivation of biogenic amino

  在嗜血杆菌科的一些生产苯基苯丙烯酮的植物中出现的苯基苯并异色酮葡糖苷（氧杂-苯基苯丙烯酮葡糖苷）在铜绿假单胞菌的提取物中转化为苯基苯并异喹啉二酮（氮杂-苯基苯乙酮）。。前驱体指导的生物合成实验用于从天然苯基苯并异色酮糖苷和外部胺，氨基酸和肽生成一系列新的苯基苯并异喹啉二酮。分离转化的中间体，与无细胞提取物一起孵育，并分别在氧化或惰性条件下暴露于反应，以阐明从苯基苯并异色酮到苯基苯并异喹啉二酮的整个途径。该途径的中间体，反应性羟基内酯/醛，不仅在体外容易与胺结合，而且在体内还可以与生物基肽和草食动物和病原体的蛋白质的N末端结合。N使生物氨基化合物失活末端修饰被讨论为一种新型的基于苯酚烯酮的植物防御机制的关键反应。根据这些数据，已经证实了苯乙醛酮类化合物在嗜血科，嗜血亚科中的生态功能。
• Phenylphenalenones from the Australian Plant <i>Haemodorum simplex</i>
  作者：Daniel Anthony Dias、David James Goble、Claudio Andres Silva、Sylvia Urban

  DOI：10.1021/np900016h

  日期：2009.6.26

  Chemical investigation of the Australian plant Haemodortun simplex resulted in the isolation of three new phenylphenalenones, haemodorone (10), haemodorol (11), and haemodorose (12), together with the previously reported compounds 5, dilatrin (6), and xiphidone (8). The first complete 2D NMR characterization for all of the compounds isolated, including several chemical shift reassignments for dilatrin (6), is reported. In addition this is one of the few reports to discuss the isolation of new phenylphenalenones from an Australian medicinal plant. The crude extract of both the bulbaceous and aerial components of the plant exhibited varying degrees of antibacterial, antifungal, and antiviral activity, and only the bulbs displayed potent cytotoxic activity.