Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F
| العنوان: | Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F |
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| المؤلفون: | Sebastian Kersting, Eric Sperlich, Bernd Schmidt, Markus von Nickisch-Rosenegk, George Kwesiga, Alexandra Kelling |
| المساهمون: | Publica |
| المصدر: | Journal of Natural Products. 83:3445-3453 |
| بيانات النشر: | American Chemical Society (ACS), 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | Pharmacology, 2019-20 coronavirus outbreak, biology, Coronavirus disease 2019 (COVID-19), 010405 organic chemistry, Chemistry, Stereochemistry, Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), Organic Chemistry, Pharmaceutical Science, Isoflavones, biology.organism_classification, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, Complementary and alternative medicine, Prenylation, Drug Discovery, Molecular Medicine, Erythrina sacleuxii, Antibacterial activity |
| الوصف: | The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4'-methoxy-3'-prenylisoflavone) and erysubin F (7,4'-dihydroxy-8,3'-diprenylisoflavone) were synthesized for the first time, starting from mono- or di-O-allylated chalcones, and the structure of 5-deoxy-3'-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4'-dihydroxy-8,3'-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4'-dihydroxy-8,3'-diprenylflavone (27), and 5-deoxy-3'-prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 mM. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4'-dihydroxy-8,3'-diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 mM, respectively. In contrast, the monoprenylated 5-deoxy-3'-prenylbiochanin A (7) is inactive against this MRSA strain. |
| تدمد: | 1520-6025 0163-3864 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f08d0dd7db85faa45eb6b0fa60a29effTest https://doi.org/10.1021/acs.jnatprod.0c00932Test |
| حقوق: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....f08d0dd7db85faa45eb6b0fa60a29eff |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206025 01633864 |
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