Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Štefanová, Iveta; Zápal, Jakub; Moos, Martin; Kuzma, Marek; Kubec, Roman

doi:10.1021/acs.jafc.9b01384

Cited by 16 publications

(6 citation statements)

References 38 publications

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“…Moreover, it revealed more intense [M − H] − ions and lower noise giving rise to higher signal-to-noise ratios and better sensitivity. On the other hand, positive ion mode was more efficient for the analysis of amino acids and γ -glutamyl peptides [ 19 , 20 ]. A total of 103 chromatographic peaks were retrieved from the examined samples comprising diverse phytochemical classes, e.g., amino acids, peptides, phenolic acids, flavonoids, saponins, and fatty acids.…”

Section: Resultsmentioning

confidence: 99%

Insights into bioactive constituents of onion (Allium cepa L.) waste: a comparative metabolomics study enhanced by chemometric tools

Elattar,

Hammoda,

Ghareeb

et al. 2024

BMC Complement Med Ther

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Background Onion waste was reported to be a valuable source of bioactive constituents with potential health-promoting benefits. This sparked a surge of interest among scientists for its valorization. This study aims to investigate the chemical profiles of peel and root extracts of four onion cultivars (red, copper-yellow, golden yellow and white onions) and evaluate their erectogenic and anti-inflammatory potentials. Methods UPLC-QqQ-MS/MS analysis and chemometric tools were utilized to determine the chemical profiles of onion peel and root extracts. The erectogenic potential of the extracts was evaluated using the PDE-5 inhibitory assay, while their anti-inflammatory activity was determined by identifying their downregulating effect on the gene expression of IL-6, IL-1β, IFN-γ, and TNF-α in LPS-stimulated WBCs. Results A total of 103 metabolites of diverse chemical classes were identified, with the most abundant being flavonoids. The organ’s influence on the chemical profiles of the samples outweighed the influence of the cultivar, as evidenced by the close clustering of samples from the same organ compared to the distinct separation of root and peel samples from the same cultivar. Furthermore, the tested extracts demonstrated promising PDE-5 and anti-inflammatory potentials and effectively suppressed the upregulation of pro-inflammatory markers in LPS-stimulated WBCs. The anti-inflammatory activities exerted by peel samples surpassed those of root samples, highlighting the importance of selecting the appropriate organ to maximize activity. The main metabolites correlated with PDE-5 inhibition were cyanidin 3-O-(malonyl-acetyl)-glucoside and quercetin dimer hexoside, while those correlated with IL-1β inhibition were γ-glutamyl-methionine sulfoxide, γ-glutamyl glutamine, sativanone, and stearic acid. Taxifolin, 3’-hydroxymelanettin, and oleic acid were highly correlated with IL-6 downregulation, while quercetin 4’-O-glucoside, isorhamnetin 4’-O-glucoside, and p-coumaroyl glycolic acid showed the highest correlation to IFN-γ and TNF-α inhibition. Conclusion This study provides a fresh perspective on onion waste as a valuable source of bioactive constituents that could serve as the cornerstone for developing new, effective anti-PDE-5 and anti-inflammatory drug candidates.

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Section: Resultsmentioning

confidence: 99%

Insights into bioactive constituents of onion (Allium cepa L.) waste: a comparative metabolomics study enhanced by chemometric tools

Elattar,

Hammoda,

Ghareeb

et al. 2024

BMC Complement Med Ther

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“…Furthermore, compounds exhibiting MS values and MS/MS fragmentation patterns expected for the homologous counterparts of cepathiolane A, onionin A, and cepadithiolactone A were also detected in both extracts (Figure ) (see the Supporting Information). − …”

Section: Resultsmentioning

confidence: 99%

Organosulfur Compounds of Allium Subgenus Nectaroscordum Species

Štefanová

Bittnerová

Zápal

et al. 2023

J. Agric. Food Chem.

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Organosulfur compounds formed upon comminuting the bulbs of two Allium subgenus Nectaroscordum species (Allium siculum and Allium tripedale) were analyzed by HPLC-PDA-MS/MS. The major organosulfur components were isolated and structurally characterized (MS, NMR), including several previously unknown compounds. It was found that the organosulfur chemistry occurring when these plants are cut is very similar to that observed in onion (Allium cepa). In all cases, however, the organosulfur compounds found in Nectaroscordum species were higher homologues of those observed in onion, being formed by various combinations of C1 and C4 building blocks derived from methiin and homoisoalliin/butiin, respectively. Thiosulfinates, bis-sulfine, cepaenes, and several cepaene-like compounds were identified among the major organosulfur components present in the homogenized bulbs. Several groups of 3,4-diethylthiolane-based compounds, structurally homologous with onionin A, cepathiolane A, allithiolanes A–H, and cepadithiolactone A, found in onion, were also detected.

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“…Furthermore, the reversible reactions of thial and sulfuric acid producing conjugated tetrasulfide (Z‐4,5,9,10‐tetrathiatrideca‐1,7,12‐triene), thiophene (3,4‐dimethylthiophene), dithiin (2‐vinyl‐4H‐1,3‐dithiin), and ajoene. These compounds are important odor components in onion and garlic (Li, Dadmohammadi, et al., 2022; Stefanova et al., 2023; Zhang et al., 2019). Significantly, a sulfur donor is needed to generate these compounds due to the adjacent configuration of the sulfide atom.…”

Section: Formation Pathways Of the Common Vscs In Foodsmentioning

confidence: 99%

“…Thus, thiosulfinate can be rapidly hydrolyzed into thiosulfonic acid and alcohol. The thiosulfonic acid and thial formed are also reactive intermediate products and subsequently transform into other aroma components (Stefanova et al., 2023). Thiosulfinate reacts with hydrogen sulfide by nucleophilic addition due to the polarity of the sulfonyl group (Krstanoski et al., 2021).…”

Section: Reaction Rules Of the Reactive Intermediatesmentioning

confidence: 99%

Mechanisms underlying the formation of main volatile odor sulfur compounds in foods during thermal processing

Luo,

Tian,

et al. 2024

Comp Rev Food Sci Food Safe

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Volatile sulfur compounds (VSCs) significantly influence food flavor and garner considerable attention in flavor research due to their low sensory thresholds, diverse odor attributes, and high reactivity. Extensive research studies have explored VSC formation through thermal processes such as the Maillard reaction, thermal pyrolysis, oxidation, and enzymatic reactions. However, understanding of the specific reaction mechanisms and processes remains limited. This is due to the dispersed nature of existing studies, the undefined intermediates involved, and the complexity of the matrices and processing conditions. Given these limitations, the authors have shifted their focus from foods to sulfides. The structure, source, and chemical characteristics of common precursors (sulfur‐containing amino acids and derivatives, thiamine, thioglucoside, and lentinic acid) and their corresponding reactive intermediates (hydrogen sulfide, thiol, alkyl sulfide, alkyl sulfenic acid, and thial) are provided, and the degradation mechanisms, reaction rules, and matrix conditions are summarized based on their chemical characteristics. Additionally, the VSC formation processes in several typical foods during processing are elucidated, adhering to these identified rules. This article provides a comprehensive overview of VSCs, from precursors and intermediates to end products, and is crucial for understanding the mechanisms behind VSC formation and managing the flavor qualities of processed foods.

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Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Cited by 16 publications

References 38 publications

Insights into bioactive constituents of onion (Allium cepa L.) waste: a comparative metabolomics study enhanced by chemometric tools

Insights into bioactive constituents of onion (Allium cepa L.) waste: a comparative metabolomics study enhanced by chemometric tools

Organosulfur Compounds of Allium Subgenus Nectaroscordum Species

Mechanisms underlying the formation of main volatile odor sulfur compounds in foods during thermal processing

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