Antimicrobial activity of the thiosulfinates isolated from oil-macerated garlic extract.
Three thiosulfinates were isolated from oil-macerated garlic extract, and their structures were identified as 2-propene-1-sulfinothioic acid S-(Z,E)-1-propenyl ester [AllS(O)SPn-(Z,E)], 2-propenesulfinothioic acid S-methyl ester [AllS(O)SMe], and methanesulfinothioic acid S-(Z,E)-1-propenyl ester [MeS(O)SPn-(Z,E)]. This is the first report of isolating these thiosulfinates from oil-macerated garlic extract. Antimicrobial activities of AllS(O)SPn-(Z,E) and AllS(O)SMe against Gram-positive and negative bacteria and yeasts were compared with 2-propene-1-sulfinothioic acid S-2-propenyl ester [AllS(O)SAll, allicin] which is well-known as the major thiosulfinate in garlic. Antimicrobial activity of AllS(O)SMe and AllS(O)SPn-(Z,E) were comparable and inferior to that of allicin, respectively. This result suggested that the antimicrobial activity of 2-propene sulfinothioic acid S-alk(en)yl esters were affected by alk(en)yl groups. The order for antimicrobial activity was: allyl > or = methyl > propenyl.
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; D000890:Anti-Infective Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D005737:Garlic / Q000737:chemistry*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal; D013441:Sulfinic Acids / Q000302:isolation & purification / Q000494:pharmacology*; D015003:Yeasts / Q000187:drug effects
C119267:2-propene-1-sulfinothioic acid S-1-propenyl ester; C119268:2-propenesulfinothioic acid S-methyl ester; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D010936:Plant Extracts; D013441:Sulfinic Acids; C119269:methanesulfinothioic acid S-1-propenyl ester