Structural and electronic properties of ajoene molecule

Erkoç, Şaki̇r; Sümer, Sibel; Erkoç, Fıgen

doi:10.1016/s0166-1280(03)00259-8

Cited by 6 publications

(5 citation statements)

References 24 publications

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“…This may be related to potential antioxidant activity. [34] The effectiveness of ajoene was 5-11 times lesser than that of more commonly used antioxidants α-tocopherol (1 mM) (Table 1). The ineffectiveness of the ajoene in the DPPH radical quenching assay was likely associated with the lack of reactivity of the sulfinyl functional unit with DPPH radical and/or the relative oxidation-reduction potentials for the alk(en)yl groups compared to respective α-tocopherol.…”

Section: Scavenging Of Dpph Radicalmentioning

confidence: 96%

“…Ajoene has cis-(Z-) and trans-(E-) isomers, both with varying degrees and specificities of bioactivity. [34] Comparing with two isomers Z-isomer is slightly more potent than E-isomer. [36] Perhaps, for these reasons Z-ajoene showed greater antioxidant activity than E-ajoene.…”

Section: Scavenging Of Hydroxyl Radical (Oh • )mentioning

confidence: 99%

“…Oxygen atom in ajoene may play in important role in the interaction of ajoene and its environment. [34] Hydrogen peroxide can be generated in biological and food systems. Being a nonradical oxygen-containing reactive agent, it can form hydroxyl radical, the most highly reactive oxygen radical known, in the presence of transition metal ions and participate in free-radical reaction.…”

Section: Very Less Omentioning

confidence: 99%

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Antioxidant Functions ofE- ANDZ-Ajoene Derived from Japanese Garlic

Naznin

Maeda

Morita

2010

International Journal of Food Properties

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Antioxidative activities of E-and Z-ajoene prepared from Japanese garlic were studied using various radical scavenging effects. Among the various antioxidative activities tested, ajoene was found to show the highest hydroxyl radicals scavenging activity (E-ajoene = 50% and Z-ajoene = 63%). These ajoene were 5.2-13 times less efficient at reducing DPPH radical and 1.1-1.4 times less efficient at hydroxyl radical as compared with authentic αtocopherol. Essentially E-and Z-ajoene were capable of scavenging superoxide anion (Eajoene = 0.11%, Z-ajoene = 3.74%), but 80 minutes later antioxidant activity could not be detected. The effectiveness of Z-ajoene is significantly higher than E-ajoene.

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Section: Scavenging Of Dpph Radicalmentioning

confidence: 96%

Section: Scavenging Of Hydroxyl Radical (Oh • )mentioning

confidence: 99%

Section: Very Less Omentioning

confidence: 99%

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Antioxidant Functions ofE- ANDZ-Ajoene Derived from Japanese Garlic

Naznin

Maeda

Morita

2010

International Journal of Food Properties

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“…It contains more than 100 biologically active secondary metabolites (13). Previous research demonstrated that garlic may be effective against cardiovascular disease because of its antithrombotic, hypolipidemic, hypocholesterolemic, antihypertensive, antidiabetic, and antihyperhomocysteinemia effects (14,15).…”

mentioning

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.…”

mentioning

confidence: 99%

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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