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Various flavonoid derivatives including methoxylated flavones display remarkable biological activities. Chrysoeriol is a methoxylated flavone of great scientific interest because of its promising anti-microbial activities against various Gram-negative and Gram-positive bacteria. Sustainable production of such compounds is therefore of pronounced interest to biotechnologists in the pharmaceutical and nutraceutical industries. Here, we used a sugar O-methyltransferase enzyme from a spinosyn biosynthesis gene cluster of Saccharopolyspora spinosa to regioselectively produce chrysoeriol (15% conversion of luteolin; 30 µM) in a microbial host. The biosynthesized chrysoeriol was structurally characterized using high-resolution mass spectrometry and various nuclear magnetic resonance analyses. Moreover, the molecule was investigated against 17 superbugs, including thirteen Gram-positive and four Gram-negative pathogens, for anti-microbial effects. Chrysoeriol exhibited antimicrobial activity against nine pathogens in a disc diffusion assay at the concentration of 40 µg per disc. It has minimum inhibitory concentration (MIC) values of 1.25 µg/mL against a methicillin-resistant Staphylococcus aureus 3640 (MRSA) for which the parent luteolin has an MIC value of sixteen-fold higher concentration (i.e., 20 µg/mL). Similarly, chrysoeriol showed better anti-microbial activity (~1.7-fold lower MIC value) than luteolin against Proteus hauseri, a Gram-negative pathogen. In contrast, a luteolin 4′-O-methylated derivative, diosmetin, did not exhibit any anti-microbial activities against any tested pathogen.

Microbial Biosynthesis of Antibacterial Chrysoeriol in Recombinant Escherichia coli and Bioactivity Assessment