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.
±)-Hypecurvone A (1) and B (2), two pairs of undescribed phenyl polyketides, along with seven known structurally related compounds were isolated from the whole plant of Hypericum curvisepalum. Chiral separation of 1 and 2 yielded two pairs of enantiomers 1a/1b and 2a/2b. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses and comparing the experimental and calculated ECD spectra. The cytotoxic effects of all the isolates on two human tumour cell lines (SMMC-7721 and MGC-803) were evaluated by CCK8 assay. All tested compounds exhibited moderate cytotoxicity against SMMC-7721 cells, and compound 3 also showed weak cytotoxicity toward MGC-803 cells. Because of their better activities, compounds 5-8 were selected to investigate the action mechanism of cytotoxicity on SMMC-7721 cells. Results suggested that the four compounds manifested cytotoxic activity by leading to mitochondria-mediated apoptosis and of inhibiting the G2/M phase to affected their normal growth.
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