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

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 antimicr...

Full description

Saved in:
Bibliographic Details
Published in:Journal of food science 2008-09, Vol.73 (7), p.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: Article
Language:English
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-1147
1750-3841
DOI:10.1111/j.1750-3841.2008.00879.x