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- W3105087002 endingPage "3453" @default.
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- W3105087002 abstract "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 μM. 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 μM, respectively. In contrast, the monoprenylated 5-deoxy-3'-prenylbiochanin A (7) is inactive against this MRSA strain." @default.
- W3105087002 created "2020-11-23" @default.
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- W3105087002 creator A5068217881 @default.
- W3105087002 date "2020-11-10" @default.
- W3105087002 modified "2023-10-06" @default.
- W3105087002 title "Total Syntheses of Prenylated Isoflavones from <i>Erythrina sacleuxii</i> and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F" @default.
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- W3105087002 doi "https://doi.org/10.1021/acs.jnatprod.0c00932" @default.
- W3105087002 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33170684" @default.
- W3105087002 hasPublicationYear "2020" @default.
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