Sustainable Straightforward Synthesis and Evaluation of the Antioxidant and Antimicrobial Activity of Sinapine and Analogues
| Autor: | Matthieu M. Mention, Florent Allais, Fanny Brunissen, Louis M. M. Mouterde, Aurélien A. M. Peru |
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| Přispěvatelé: | Agro-Biotechnologies Industrielles (ABI), AgroParisTech |
| Rok vydání: | 2020 |
| Předmět: |
0106 biological sciences
Antioxidant Sinapine medicine.medical_treatment [CHIM.THER]Chemical Sciences/Medicinal Chemistry Meldrum's acid 01 natural sciences Syringaldehyde Antioxidants Choline chemistry.chemical_compound 4-Hydroxybenzaldehyde Escherichia coli medicine Organic chemistry Molecular Structure Vanillin 010401 analytical chemistry Choline phenolic esters General Chemistry Antimicrobial Anti-Bacterial Agents 0104 chemical sciences Choline chloride chemistry General Agricultural and Biological Sciences Knoevenagel-Doebner 010606 plant biology & botany |
| Zdroj: | Journal of Agricultural and Food Chemistry Journal of Agricultural and Food Chemistry, American Chemical Society, 2020, 68 (26), pp.6998-7004. ⟨10.1021/acs.jafc.0c02183⟩ |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.0c02183 |
| Popis: | International audience; Naturally occurring sinapine was successfully synthesized through a proline-mediated Knoevenagel–Doebner condensation in ethanol. This synthetic process involving biobased syringaldehyde, Meldrum’s acid, and choline chloride offers a sustainable alternative to the existing low-yield pathways. This two-step strategy gives access to sinapine in a 52% overall yield and has been implemented in the synthesis of sinapine analogues, using 4-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and vanillin as precursors, giving target molecules with 34–61% overall isolated yields. The purity of synthetic sinapine and its analogues (ca. 95%) was assessed by NMR and high-performance liquid chromatography—mass spectrometry analyses. Furthermore, the antioxidant and antimicrobial activities were assessed, and the potential of this series of molecules was confirmed. |
| Databáze: | OpenAIRE |
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