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-ofthe- 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.
Huber R., Marcourt L., Koval A., Schnée S., Righi D., Michellod E., Katanaev V., Wolfender JL., Gindro K., Queiroz E.
Chemoenzymatic synthesis of complex phenylpropanoid derivatives by the Botrytis cinerea secretome and evaluation of their Wnt inhibition activity.
Frontiers in Plant Science, 12, 2022, 1-19.
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ISSN Online: 1664-462X
Digital Object Identifier (DOI): https://doi.org/10.3389/fpls.2021.805610
ID pubblicazione (Codice web): 48962 Inviare via e-mail
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