关键词: Botrytis cinerea Wnt inhibition biotransformation chemoenzymatic synthesis dry load introduction enzymatic secretome high-resolution semi-preparative HPLC phenylpropanoids Botrytis cinerea Wnt inhibition biotransformation chemoenzymatic synthesis dry load introduction enzymatic secretome high-resolution semi-preparative HPLC phenylpropanoids

来  源:   DOI:10.3389/fpls.2021.805610   PDF(Pubmed)

Abstract:
In this study, a series of complex phenylpropanoid derivatives were obtained by chemoenzymatic biotransformation of ferulic acid, caffeic acid, and a mixture of both acids using the enzymatic secretome of Botrytis cinerea. These substrates were incubated with fungal enzymes, and the reactions were monitored using state-of-the-art analytical methods. Under such conditions, a series of dimers, trimers, and tetramers were generated. The reactions were optimized and scaled up. The resulting mixtures were purified by high-resolution semi-preparative HPLC combined with dry load introduction. This approach generated a series of 23 phenylpropanoid derivatives, 11 of which are described here for the first time. These compounds are divided into 12 dimers, 9 trimers (including a completely new structural scaffold), and 2 tetramers. Elucidation of their structures was performed with classical spectroscopic methods such as NMR and HRESIMS analyses. The resulting compound series were analyzed for anti-Wnt activity in TNBC cells, with several derivatives demonstrating specific inhibition.
摘要:
在这项研究中,通过对阿魏酸的化学酶生物转化,获得了一系列复杂的苯丙素衍生物,咖啡酸,以及两种酸的混合物,使用灰葡萄孢菌的酶促分泌体。这些底物与真菌酶一起孵育,并使用最先进的分析方法监测反应。在这样的条件下,一系列二聚体,三聚体,并产生四聚体。对反应进行优化和放大。将所得混合物通过高分辨率半制备型HPLC与干负载引入结合纯化。这种方法产生了一系列23个苯丙烷类衍生物,其中11个是第一次描述。这些化合物分为12个二聚体,9个三聚体(包括一个全新的结构支架),和2个四聚体。用经典的光谱方法如NMR和HRESIMS分析进行其结构的阐明。分析所得化合物系列在TNBC细胞中的抗Wnt活性,几种衍生物表现出特异性抑制作用。
公众号