Antibacterial Compounds from Rose Bengal-Sensitized Photooxidation of β-Caryophyllene

• Published in: Journal of food science Vol. 73; no. 7; pp. C540 - C545
• Main Authors: Kim, Y.S, Park, S.J, Lee, E.J, Cerbo, R.M, Lee, S.M, Ryu, C.H, Kim, G.S, Kim, J.O, Ha, Y.L
• Format: Journal Article
• Language: English
• Published: Malden, USA Blackwell Publishing Inc 01.09.2008; Wiley
• Subjects: Anti-Bacterial Agents - pharmacology; antibacterial properties; antimicrobial activity; antimicrobial agents; bacterial contamination; beta-caryophyllene; Biological and medical sciences; Chromatography, Gel; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; disease control; dyes; fluorescent lighting; food contamination; Food industries; Food microbiology; food pathogens; Fundamental and applied biological sciences. Psychology; high performance liquid chromatography; infrared spectroscopy; Light; mass spectrometry; Microbial Sensitivity Tests; nuclear magnetic resonance spectroscopy; Oxidation-Reduction; photooxidation; Rose Bengal - chemistry; Rose Bengal dye; S. aureus; Sesquiterpenes - pharmacology; Staphylococcus aureus; Staphylococcus aureus - drug effects; Streptococcus; V. parahaemolyticus; Vibrio parahaemolyticus; Vibrio parahaemolyticus - drug effects; β-caryophyllene; β-caryophyllene; S. aureus; V. parahaemolyticus; Rose; antimicrobial activity; Antibacterial agent; Photooxidation; Antimicrobial agent
• ISSN: 0022-1147; 1750-3841
• DOI: 10.1111/j.1750-3841.2008.00879.x

The bactericidal activity of β-caryophyllene photooxidized in acetonitrile was examined for 5 Gram-positive and 4 Gram-negative foodborne bacteria. The β-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 β-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 β-caryophyllene was strongly enhanced against Streptococcus aureus and Vibrio parahaemolyticus, relative to that of β-caryophyllene, but was weakly enhanced against other tested bacteria. The photooxidized β-caryophyllene contained 3 active compounds specific for these 2 bacteria, and the compounds were identified as 5-α-hydroxycaryophylla-4(12),8(13)-diene, 5-α-hydroxycaryophylla-3(4),8(13)-diene, and 5-β-hydroxycaryophylla-3(4),8(13)-diene. The efficacies of these compounds were similar, but the efficacy of 5-β-hydroxycaryophylla-3(4),8(13)-diene was slightly higher than that of the other 2 compounds. The results suggest that the antibacterial activities of β-caryophyllene for S. aureus and V. parahaemolyticus could be enhanced by dye-sensitized photooxidation, and the photooxidized β-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.