Allicin and related compounds: Biosynthesis, synthesis and pharmacological activity

Ilić, Dušica P.; Nikolić, Vesna; Nikolić, Ljubiša; Stanković, Miomir; Stanojević, Ljiljana P.; Cakić, Milorad D.

doi:10.2298/fupct1101009i

Cited by 73 publications

(61 citation statements)

References 38 publications

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“…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).…”

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confidence: 99%

“…The primary sulfur-containing constituents in garlic are S-alk-(en)yl-L-cysteine sulfoxides, such as alliin [(ϩ)-(S)-allyl-L-cysteine-sulfoxide] and ␥-glutamyl cysteines (15,16). When a raw garlic bulb is crushed, alliin and alliinase, which are stored in sep-arate cellular compartments of the garlic clove, are mixed together.…”

mentioning

confidence: 99%

“…When a raw garlic bulb is crushed, alliin and alliinase, which are stored in sep-arate cellular compartments of the garlic clove, are mixed together. In the role of alliinase, alliin is further subjected to dehydration by pyridoxal phosphate and transformed to allyl sulfenic acid, pyruvic acid, and ammonia (16). Allyl sulfenic acid is unstable and very reactive at room temperature.…”

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confidence: 99%

“…With the elimination of water, two molecules of allyl sulfenic acid condense spontaneously to allicin (see Fig. S1A in the supplemental material), validated as an important substance for the medicinal properties of garlic (13,(15)(16)(17). However, allicin is an unstable compound which is rapidly decomposed into other stable sulfur-containing constituents.…”

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confidence: 99%

“…Specifically, ajoene [(E)-and (Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxides] is commonly found in oil-macerated/ether-extracted garlic oil, with E-ajoene usually present at levels twice as high as those of Z-ajoene, while steam-distilled garlic oil is mainly composed of lipid-soluble sulfur compounds, including diallyl sulfide, diallyl disulfide, and diallyl trisulfide, and of minor amounts of many other volatile compounds, such as allyl methyl disulfide and diallyl tetrasulfide (see Fig. S1B) (15,16,23).…”

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confidence: 99%

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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

Feng

Eucker

Holly

et al. 2014

Appl Environ Microbiol

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We present the results of a study using high-throughput whole-transcriptome sequencing (RNA-seq) and vibrational spectroscopy to characterize and fingerprint pathogenic-bacterium injury under conditions of unfavorable stress. Two garlic-derived organosulfur compounds were found to be highly effective antimicrobial compounds against Cronobacter sakazakii, a leading pathogen associated with invasive infection of infants and causing meningitis, necrotizing entercolitis, and bacteremia. RNA-seq shows changes in gene expression patterns and transcriptomic response, while confocal micro-Raman spectroscopy characterizes macromolecular changes in the bacterial cell resulting from this chemical stress. RNA-seq analyses showed that the bacterial response to ajoene differed from the response to diallyl sulfide. Specifically, ajoene caused downregulation of motility-related genes, while diallyl sulfide treatment caused an increased expression of cell wall synthesis genes. Confocal micro-Raman spectroscopy revealed that the two compounds appear to have the same phase I antimicrobial mechanism of binding to thiol-containing proteins/enzymes in bacterial cells generating a disulfide stretching band but different phase II antimicrobial mechanisms, showing alterations in the secondary structures of proteins in two different ways. Diallyl sulfide primarily altered the ␣-helix and ␤-sheet, as reflected in changes in amide I, while ajoene altered the structures containing phenylalanine and tyrosine. Bayesian probability analysis validated the ability of principal component analysis to differentiate treated and control C. sakazakii cells. Scanning electron microscopy confirmed cell injury, showing significant morphological variations in cells following treatments by these two compounds. Findings from this study aid in the development of effective intervention strategies to reduce the risk of C. sakazakii contamination in the food production environment and on food contact surfaces, reducing the risks to susceptible consumers. Cronobacter sakazakii is a motile, nonsporeforming Gram-negative facultative anaerobe (1). It was noted to be an opportunistic pathogen responsible for life-threatening forms of meningitis, sepsis, necrotizing colitis, bacteremia, and meningoencephalitis in preterm neonates and infants (2-6). The mortality rate for neonatal infections has been reported to be as high as 80% (7). C. sakazakii infections may also result in severe neurological sequelae such as hydrocephalus, quadriplegia, and retarded neural development in survivors (8). Epidemiological studies implicated powdered infant formula as a primary source of transmission (6); indeed, this bacterium was detected in 2.4% to 14.2% of powdered infant formula products (5). Antibiotic therapy with a combination of ampicillin and gentamicin is an efficient method to treat C. sakazakii infections (4). However, the emergence of strains resistant to antibiotics has led the design and use of novel antimicrobials. In recent years, plant-derivedbiologicallyactivecompo...

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