- 8-Dimethylallylnaringenin 2′-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells
-
8-Dimethylallylnaringenin (8-DMAN) 2′-hydroxylase, which is indispensable for the formation of a lavandulylated flavanone, sophoraflavanone G, was detected in cell suspension cultures of Sophora flavescens. The enzyme catalyzes the 2′-hydroxylation of 8-D
- Yamamoto, Hirobumi,Yatou, Atsushi,Inoue, Kenichiro
-
-
Read Online
- Regio- and stereospecific prenylation of flavonoids by Sophora flavescens prenyltransferase
-
Prenylflavonoids are valuable natural products that are widely distributed in plants. They often possess divergent biological properties, including phytoestrogenic, anti-bacterial, anti-tumor, and anti-diabetic activities. The reaction catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylflavonoids and often contributes to the structural diversity and biological activity of these compounds. However, only a few plant flavonoid prenyltransferases have been identified thus far, and these prenyltransferases exhibit strict substrate specificity and low catalytic efficiency. In this article, a flavonoid prenyltransferase from Sophora flavescens, SfFPT, has been identified that displays high catalytic efficiency with high regiospecificity acting on C-8 of structurally different types of flavonoid (i.e., flavanone, flavone, flavanonol, and dihydrochalcone, etc.). Furthermore, SfPFT exhibits strict stereospecificity for levorotatory flavanones to produce (2S)-prenylflavanones. This study is the first to demonstrate the substrate promiscuity and stereospecificity of a plant flavonoid prenyltransferase in vitro. Given its substrate promiscuity and high catalytic efficiency, SfFPT can be used as an environmentally friendly and efficient biological catalyst for the regio- and stereospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications. Copyright
- Chen, Ridao,Liu, Xiao,Zou, Jianhua,Yin, Yunze,Ou, Bin,Li, Jianhua,Wang, Ruishan,Xie, Dan,Zhang, Peicheng,Dai, Jungui
-
p. 1817 - 1828
(2013/07/19)
-
- Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents
-
A series of prenylflavonoids with multiple hydroxyl groups were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pre-contracted by phenylephrine (PE), as well as their neuroprotective effects against OGD induced PC12 cel
- Dong, Xiaowu,Qi, Lingling,Jiang, Chaoyi,Chen, Jing,Wei, Erqing,Hu, Yongzhou
-
scheme or table
p. 3196 - 3198
(2010/03/03)
-
- Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures
-
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 μM, 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.
- Yamamoto, Hirobumi,Senda, Masayuki,Inoue, Kenichiro
-
p. 649 - 655
(2007/10/03)
-