Antibacterial compounds from Rose Bengal-sensitized photooxidation of beta-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.
Kim
Y S
YS
Division of Applied Life Sciences, BK21 Program, Graduate School, Inst of Agriculture & Life Science, Jinju, Republic of Korea.
Park
S J
SJ
Lee
E J
EJ
Cerbo
R M
RM
Lee
S M
SM
Ryu
C H
CH
Kim
G S
GS
Kim
J O
JO
Ha
Y L
YL
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D008027:Light; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D000081223:Polycyclic Sesquiterpenes; D012395:Rose Bengal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D014736:Vibrio parahaemolyticus / Q000187:drug effects
C534724:5-hydroxycaryophylla-3(4),8(13)-diene; C534723:5-hydroxycaryophylla-4(12),8(13)-diene; D000900:Anti-Bacterial Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D012395:Rose Bengal; C024714:caryophyllene