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.

Augmentation of natural killer cell activity in vivo against tumour cells by some wild plants from Jordan

“…Thymoquinone is reported to have significant protection against hepatotoxicity ( Daba and Abdel Rahman, 1998). Also, A.s. was found to have several antimicrobial compounds such as thiosulphinates (Yoshida et al, 1999) as well as antitumour active principles such as diallyl sulphide, allicin and ajoene (Singh and Shukla, 1998;Dirsch et al, 1998). This antitumour activity may have been caused through stimulation of the immune system including NK cells.…”

Isolation and Identification of Causal Constituents of Green Discoloration in Garlic Puree

“…(2-propenyl E-1-propenethiosulfinate; 2P1PTS) and 2-propene-1-sulfinothioic acid S-(E,Z)-1-propenyl ester ((E,Z)-1-propenyl 2-propenethiosulfinate; 1P2PTS) by comparison of the obtained NMR and MS data with that previously reported (Lawson et al, 1991;Block et al, 1996;Calvey et al, 1997;Yoshida et al, 1999). Both compounds are known to be present in garlic homogenates (Lawson et al, 1991;Block et al, 1992).…”

Enhancement of Intestinal IgA Production by Ajoene in Mice

“…In addition to ajoene, OMGE primarily contained devinylajoene, vinyldithiin, and some thiosulfinates. [3][4][5] Our results suggest that, other than ajoene, no component of OMGE influenced the increase in intestinal IgA production, and that no additive or synergistic effects were apparent between ajoene and the other components of OMGE.…”

“…4,5) Ajoene was shown by Block et al 6) in 1984 to be an inhibitor of platelet aggregation, and its various biological activities have been well studied. Ajoene has exhibited antibiotic, 7) hepatoprotective, 8) anti-tumor, 9) and anti-diabetic effects.…”