(S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone

• 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: (S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone
• 英文别名: 6-isoprenyl eriodictyol；6-prenyleriodictyol；6-C-prenyleriodictyol；(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: KBEFFXBSHFUQLT-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 以1.5 mg的产率得到(S)-2-(3,4-Dihydroxy-phenyl)-5-hydroxy-8,8-dimethyl-2,3,7,8-tetrahydro-6H-pyrano[3,2-g]chromen-4-one
  参考文献：
  名称：

  来自 Wyethia helenioides 的二萜、倍半萜醌和黄烷酮

  摘要：

  摘要 Wyethia helenioides 的地上部分提供了一种新的香叶橙花醇衍生物（一种 16-羟基-18-油酸）、两种异构的异戊二烯化紫檀酮和一种源自红没药烯的醌。通过光谱方法和一些化学转化阐明了结构。简要讨论了化学分类情况。

  DOI：

  10.1016/0031-9422(81)80122-7
• 作为产物：
  描述：

  圣草酚 、 DMAPP 在 indole prenyltransferase 7-DMATS 、 calcium chloride 作用下， 以 二甲基亚砜 、 甘油 为溶剂， 反应 16.0h， 以22.8%的产率得到(S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone
  参考文献：
  名称：

  Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

  摘要：

  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.

  DOI：

  10.1021/acs.jnatprod.5b00422

文献信息

• 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.
• A diterpene, a sesquiterpene quinone and flavanones from Wyethia helenioides
  作者：Ferdinand Bohlmann、Christa Zdero、Harold Robinson、Robert M. King

  DOI：10.1016/0031-9422(81)80122-7

  日期：1981.1

  Abstract The aerial parts of Wyethia helenioides afforded a new geranyl nerol derivative (a 16-hydroxy-18-oic acid), two isomeric prenylated lavanones and a quinone derived from bisabolene. The structures were elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic situation is discussed briefly.

  摘要 Wyethia helenioides 的地上部分提供了一种新的香叶橙花醇衍生物（一种 16-羟基-18-油酸）、两种异构的异戊二烯化紫檀酮和一种源自红没药烯的醌。通过光谱方法和一些化学转化阐明了结构。简要讨论了化学分类情况。