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Chemoenzymatic synthesis of complex phenylpropanoid derivatives by the Botrytis cinerea secretome and evaluation of their wnt inhibition activity

Published inFrontiers in plant science, vol. 12, 805610
First online date2022-01-13
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.

Keywords
  • Chemoenzymatic synthesis
  • Biotransformation
  • Botrytis cinerea
  • Enzymatic secretome
  • Phenylpropanoids
  • High-resolution semi-preparative HPLC
  • Dry load introduction
  • Wnt inhibition
Citation (ISO format)
HUBER, Robin et al. Chemoenzymatic synthesis of complex phenylpropanoid derivatives by the Botrytis cinerea secretome and evaluation of their wnt inhibition activity. In: Frontiers in plant science, 2022, vol. 12, p. 805610. doi: 10.3389/fpls.2021.805610
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ISSN of the journal1664-462X
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Creation01/31/2022 2:46:00 PM
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