title: Antimicrobial activity of the thiosulfinates isolated from oil-macerated garlic extract.
abstract: 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.
authors.affiliation: Biodevelopment Division, Nagoya Seiraku Co. Ltd., Aichi, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Yoshida
authors.forename: H
authors.initials: H
authors.lastname: Katsuzaki
authors.forename: R
authors.initials: R
authors.lastname: Ohta
authors.forename: K
authors.initials: K
authors.lastname: Ishikawa
authors.forename: H
authors.initials: H
authors.lastname: Fukuda
authors.forename: T
authors.initials: T
authors.lastname: Fujino
authors.forename: A
authors.initials: A
authors.lastname: Suzuki
mesh_terms: 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
chemical_list: 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