All the isolated compounds were described for the first time from this species. Although inactive against 7 tested microorganisms (fungi, bacteria and yeast, human or plant pathogens), the raw extract was able to potentiate the effect of beta-lactam antibiotics on methicillin-resistant Staphylococcus aureus (MRSA), reducing the minimal inhibitory concentrations (MICs) by a factor of 2-32-fold. No synergy was found between the extract and streptomycin. From the five isolated compounds only jaseosidin 5 showed a moderate antimicrobial activity.
The title compound [systematic name: 3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylenedecahydroazuleno[4,5-b]furan-2(3H)-one], C15H22O5, is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the molecular structure, assigned by 1H NMR and MS spectroscopy, as well as the the 11β-hydroxymethyl, 3β-hydroxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O—H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the molecular skeleton.
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