An organosulfur compound isolated from oil-macerated garlic extract, and its antimicrobial effect.
An organosulfur compound was isolated from oil-macerated garlic extract by silica gel column chromatography and preparative TLC. From the results of NMR, IR, and MS analyses, its structure was determined as E-4,5,9-trithiadeca-1,7-diene-9-oxide (iso-E-10-devinylajoene, iso-E-10-DA). This compound was different from E-4,5,9-trithiadeca-1,6-diene-9-oxide (E-10-devinylajoene, E-10-DA) only in the position of a double bond. Iso-E-10-DA had antimicrobial activity against Gram-positive bacteria, such as Bacillus cereus, B. subtilis, and Staphylococcus aureus, and yeasts at the concentration lower than 100 micrograms/ml, but Gram-negative bacteria were not inhibited at the same concentration. The antimicrobial activity of iso-E-10-DA was inferior to those of similar oil-macerated garlic extract compounds such as E-ajoene, Z-ajoene, and Z-10-DA. From these results, it was suggested that trans structure and/or the position of double bond of iso-E-10-DA reduce the antimicrobial activity.
Yoshida
H
H
Biodevelopment Division, Nagoya Seiraku Co., Ltd., Aichi, Japan.
Katsuzaki
H
H
Ohta
R
R
Ishikawa
K
K
Fukuda
H
H
Fujino
T
T
Suzuki
A
A
D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology*; D002855:Chromatography, Thin Layer; D004220:Disulfides / Q000302:isolation & purification / Q000494:pharmacology*; D005737:Garlic / Q000737:chemistry*; D006094:Gram-Positive Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D009821:Oils; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal; D013055:Spectrophotometry, Infrared; D013454:Sulfoxides / Q000302:isolation & purification / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D004220:Disulfides; D009821:Oils; D010936:Plant Extracts; D013454:Sulfoxides; C119266:iso-10-devinylajoene