The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: structural, mechanistic, and synthetic studies

Antibacterial Potential of Garlic-Derived Allicin and Its Cancellation by Sulfhydryl Compounds

“…As to garlic chemistry, Block et al presented in detail the fate of organosulfur compounds originating from alliin (S-allyl cysteine sulfoxide). 9) However, the chemical interactions operating between garlic-derived allicin and bacteria and between allicin and an animal or its cells have not been clarified as yet.…”

“…Allicin is known to degrade into several smaller molecules, which then combine to build up stable sulfide compounds with a concomitant release of oxygen. 9) Therefore, a similar mechanism by which leukocytes kill microbes in their phagosomes has been proposed for allicin. On the other hand, recent findings of our anticancer study 10) and of an antifungal study by Ogita et al 11) indicate that allicin or allicin-derived molecules modify the proteins necessary for cell division or detoxification.…”

Antimutagenic Effects of Ajoene, an Organosulfur Compound Derived from Garlic

“…Allicin, however, is rapidly converted to diallyl disulfide and other sulfur compounds because of its instability. Ajoene, [4][5][6] [(E,Z) -4,5,9-trithiadodeca-I ,6, II-triene-9-oxide], one of the derivatives of allicin, has been found as a major sulfur-containing compound in an oil-macerated garlic extract 7) (Fig. I) and was reported to inhibit platelet aggregation.…”

Investigating the Responses of Cronobacter sakazakii to Garlic-Drived Organosulfur Compounds: a Systematic Study of Pathogenic-Bacterium Injury by Use of High-Throughput Whole-Transcriptome Sequencing and Confocal Micro-Raman Spectroscopy

“…The filtrate was concentrated under a vacuum and purified by the use of a chromatography column to get allicin (compound 2) (1.2 g, 71% yield) as a light yellow liquid. 1 H nuclear magnetic resonance (NMR) (CDCl 3 ) levels of 6.30 to 5.04 (m, 6 H) and 3.94 to 3.65 (m, 4 H) were determined as follows; the NMR data are in accordance with previous publication (20): Allicin (compound 2) (1.0 g, 6.2 mmol) was dissolved in 40% aqueous acetone (10.0 ml), and the homogeneous solution was heated at 65°C for 4 h. The reaction mixture was diluted with 50% aqueous methanol (40.0 ml) and washed with hexane (5ϫ; 20.0 ml). The aqueous methanolic layer was then saturated with ammonium sulfate and extracted with methylene chloride (20.0ϫ; 2 ml).…”

“…Previous research demonstrated that garlic may be effective against cardiovascular disease because of its antithrombotic, hypolipidemic, hypocholesterolemic, antihypertensive, antidiabetic, and antihyperhomocysteinemia effects (14,15). Further, garlic possesses many other biological activities, including antimicrobial, antioxidant, anticancer, antimutagenic, antiasthmatic, and anti-inflammatory immune modulation activities and prebiotic activities (14)(15)(16)(17)(18)(19)(20)(21)(22). Evidence suggests that the biological and medical functions of garlic are mainly due to its high level of organosulfur compounds (15), while proteins derived from garlic do not have antimicrobial activity (23) and phenolic compounds make only a minor contribution (24).…”