The chloroform extract
of Origanum majorana exhibited high
antibacterial and antifungal activities against 12
bacterial and 4 fungal strains; therefore, it was subjected to bioassay-guided
isolation to afford six compounds (1–6). The structures were determined via one- and two-dimensional nuclear
magnetic spectroscopy and high-resolution electrospray ionization
mass spectrometry experiments. The compounds were identified as furanonaphthoquinones
[majoranaquinone (1), 2,3-dimethylnaphtho[2,3-b]furan-4,9-dione (2)], diterpenes [19-hydroxyabieta-8,11,13-trien-7-one
(3), 13,14-seco-13-oxo-19-hydroxyabieta-8-en-14-al (4)], and flavonoids [sterubin (5) and majoranin
(6)]. Compounds 1 and 2 were
first obtained from a natural source and compounds 3 and 4 were previously undescribed. Majoranaquinone (1) exhibited a high antibacterial effect against 4 Staphylococcus, 1 Moraxella, and 1 Enterococcus strains (MIC
values between 7.8 μM and 1 mM). In the efflux pump inhibition
assay, majoranaquinone (1) showed substantial activity
in Escherichia coli ATCC 25922 strain.
Furthermore, 1 was found to be an effective biofilm formation
inhibitor on E. coli ATCC 25922 and E. coli K-12 AG100 bacteria. Our findings proved
that bioactivities of majoranaquinone (1) significantly
exceed those of the essential oil constituents; therefore, it should
also be considered when assessing the antimicrobial effects of O. majorana.