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Two new epimeric bibenzylated monoterpenes machaerifurogerol ( 1a ) and 5- epi -machaerifurogerol ( 1b ), and four known isoflavonoids (+)-vestitol ( 2 ), 7- O -methylvestitol ( 3 ), (+)-medicarpin ( 4 ), and 3,8-dihydroxy-9-methoxypterocarpan ( 5 ) were isolated from Machaerium Pers. This plant was previously assigned as Machaerium multiflorum Spruce, from which machaeriols A-D ( 6 - 9 ) and machaeridiols A-C ( 10 - 12 ) were reported, and all were then re-isolated, except the minor compound 9 , for a comprehensive antimicrobial activity evaluation. Structures of the isolated compounds were determined by full NMR and mass spectroscopic data. Among the isolated compounds, the mixture 10 + 11 was the most active with an MIC value of 1.25 μg/mL against methicillin-resistant Staphylococcus aureus (MRSA) strains BAA 1696, -1708, -1717, -33591, and vancomycin-resistant Enterococcus faecium (VRE 700221) and E . faecalis (VRE 51299) and vancomycin-sensitive E. faecalis (VSE 29212). Compounds 6 - 8 and 10 - 12 were found to be more potent against MRSA 1708, and 6 , 11 , and 12 against VRE 700221, than the drug control ciprofloxacin and vancomycin. A combination study using an in vitro Checkerboard method was carried out for machaeriols ( 7 or 8 ) and machaeridiols ( 11 or 12 ), which exhibited a strong synergistic activity of 12 + 8 (MIC 0.156 and 0.625 µg/mL), with &gt;32- and &gt;8-fold reduction of MIC's, compared to 12 , against MRSA 1708 and -1717, respectively. In the presence of sub-inhibitory concentrations on polymyxin B nonapeptide (PMBN), compounds 10 + 11 , 11 , 12 , and 8 showed activity in the range of 0.5-8 µg/mL for two strains of Acinetobacter baumannii , 2-16 µg/mL against Pseudomonas aeruginosa PAO1, and 2 µg/mL against Escherichia coli NCTC 12923, but were inactive (MIC &gt; 64 µg/mL) against the two isolates of Klebsiella pneumoniae .

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Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens