Three New Xanthones from Hypericum scabrum and Their Quorum Sensing Inhibitory Activities against Chromobacterium violaceum

Abstract

Quorum sensing (QS) plays an important role in the production of virulence factors and pathogenicity in pathogenic bacteria and is, therefore, a hopeful target to fight against bacterial infections. During our search for natural QS inhibitors, two new xanthonolignoids (1 and 2), each existing as a racemic mixture, one new simple oxygenated xanthone (7), and eight known analogs (3–6, 8–11) were isolated from Hypericum scabrum Linn. Chiral separation of 1 yielded a pair of enantiomers 1a and 1b. The structures of these compounds were elucidated by spectroscopic analysis and ECD (electrostatic circular dichroism) calculations. All isolates were evaluated for their QS inhibitory activity against Chromobacterium violaceum. Both 9 and 10 exhibited the most potent QS inhibitory effects with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 31.25 and 62.5 μM, respectively. Crystal violet staining was used to further evaluate the biofilm inhibition potential of compounds 7, 9 and 10, and the formation of biofilms increased with decreasing drug concentration in a classic dose-dependent manner. The results of a cytotoxicity assay revealed that compounds 7, 9 and 10 exhibited no cytotoxic activity on PC-12 cells at the tested concentration.

In vitro antimicrobial and antibiofilm screening of eighteen Iranian medicinal plants

“…Also, our present observations are in agreement with another previous study by Keser et al, [ 29 ] who reported the potent antimicrobial activity of H. scabrum against E. coli, Proteus vulgaris, P. aeruginosa, Listeria monocytogenes, Klebsielle pneumonia and Bacillus subtilis . It was reported that H. scabrum contains a variety of secondary metabolites such as flavonoids [ 30 ], xanthones [ 31 ], and especially phloroglucinols [ 32 , 33 ]. It was found that lipophilic fractions of Hypericum species contain phloroglucinol derivatives, which have been demonstrated to have antifungal and antibacterial properties against pathogens like S. aureus, B. cereus, B. subtilis, and Nocardia gardenen [ 34 ] .…”