Inactivation of Jack Bean Urease by Allicin

Abstract

Allicin--diallyl thiosulfinate--is the main biologically active component of freshly crushed garlic. Allicin was synthesized as described elsewhere and was tested for its inhibitory ability against jack bean urease in 20 mM phosphate buffer, pH 7.0 at 22 degrees C. The results indicate that allicin is an enzymatic inactivator. The loss of urease activity was irreversible, time- and concentration dependent and the kinetics of the inactivation was biphasic; each phase, obeyed pseudo-first-order kinetics. The rate constants for inactivation were measured for the fast and slow phases and for several concentrations of allicin. Thiol reagents, and competitive inhibitor (boric acid) protected the enzyme from loss of enzymatic activity. The studies demonstrate that urease inactivation results from the reaction between allicin and the SH-group, situated in the urease active site (Cys592).

Selective Antibacterial Activity of Patchouli Alcohol Against Helicobacter pylori Based on Inhibition of Urease

“…Therefore, SH‐blocking reagent was employed to examine its effects on the inhibitory activity of PA against ureases. When DTT was added to the pre‐incubation medium, instead restoring the inhibition of urease activity by some reported compounds like allicin, quinine, and flavonoid (Juszkiewicz et al ., ; Kot, ; Tan et al ., ), the inhibitory activity of PA was strengthened by DTT. Chemical studies have shown that various sesquiterpenes react with thiols (Kupchan et al ., ; Kupchan et al ., ).…”

Jack bean urease inhibition by crude juices of Allium and Brassica plants. Determination of thiosulfinates

“…Studies of urease inhibition by garlic have been already published (Juszkiewicz et al, 2003(Juszkiewicz et al, , 2004Zaborska et al, 2009). Thiosulfinates of garlic extracts inactivate urease as a result of a modification of urease -SH groups.…”

“…The Brassica species contain only methiin, which is converted into methylmethanethiosulfinate and then to dimethylthiosulfonate, dimethylsulfide and polymethylsulfides (Kyung & Lee, 2001;Rose et al, 2005). The inhibition of jack bean urease by garlic extract has already been investigated by our staff (Juszkiewicz, Zaborska, Sepioł, Góra, & Zaborska, 2003;Juszkiewicz, Zaborska, Łaptaś, & Olech, 2004;Zaborska, Karcz, Kot, & Juszkiewicz, 2009). It has been found that allicin the most abundant TS present in fresh garlic extract is responsible for inhibition of the enzyme.…”

Synthesis of benzoyl hydrazones having 4-hydroxy-3,5-dimethoxy phenyl ring, their biological activities and moleculer modeling studies on enzyme inhibition activities

“…Additionally, this compound formed a very strong hydrogen bond interaction with the Cys592 in the mobile flap closing the active site of the urease enzyme [54] with bond distance 2.12 Å (Figure 7). In summary, based on this analysis, all synthesized compounds interacted with the catalytic functional sites of the target proteins.…”