Antibacterial compounds from Rose Bengal-sensitized photooxidation of β-caryophyllene

The bactericidal activity of beta-caryophyllene photooxidized in acetonitrile was examined for 5 Gram-positive and 4 Gram-negative foodborne bacteria. The beta-caryophyllene (5 x 10(-3) M) was photooxidized in acetonitrile containing Rose Bengal (6.25 x 10(-4) M) for 24 h under fluorescent light. The antimicrobial activities of samples were determined by the agar-disc diffusion method. Active compounds from the photooxidized beta-caryophyllene were isolated by silica gel open-column chromatography in conjunction with recyclic high-performance liquid chromatography (HPLC), and were identified by infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance spectroscopy. The antimicrobial activity of the photooxidized beta-caryophyllene was strongly enhanced against Streptococcus aureus and Vibrio parahaemolyticus, relative to that of beta-caryophyllene, but was weakly enhanced against other tested bacteria. The photooxidized beta-caryophyllene contained 3 active compounds specific for these 2 bacteria, and the compounds were identified as 5-alpha-hydroxycaryophylla-4(12),8(13)-diene, 5-alpha-hydroxycaryophylla-3(4),8(13)-diene, and 5-beta-hydroxycaryophylla-3(4),8(13)-diene. The efficacies of these compounds were similar, but the efficacy of 5-beta-hydroxycaryophylla-3(4),8(13)-diene was slightly higher than that of the other 2 compounds. The results suggest that the antibacterial activities of beta-caryophyllene for S. aureus and V. parahaemolyticus could be enhanced by dye-sensitized photooxidation, and the photooxidized beta-caryophyllene and the isolated individual compounds could be useful antimicrobial agents to control the growth of S. aureus and V. parahaemolyticus in certain food systems.