Variability in S-Alk(en)yl-l-Cysteine Sulfoxides in Garlic within a Seven-Month Period Determined by a Liquid Chromatography – Tandem Mass Spectrometry Method

Rektorisova, Michaela; Hrbek, Vojtěch; Jírů, Monika; Ovesná, Jaroslava; Hajšlová, Jana

doi:10.1007/s11130-020-00817-z

Cited by 8 publications

(8 citation statements)

References 28 publications

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“…Within‐type significant differences were also observed, with special respect to the relative content of minor sulphoxides MET and i ALL. Quantitative and qualitative results are in accordance with data determined on garlic samples collected all over the world 8,14,15 …”

Section: Resultssupporting

confidence: 87%

“…Quantitative and qualitative results are in accordance with data determined on garlic samples collected all over the world. 8,14,15 Volatile organosulphur compounds (OSCs) Twenty-seven volatile compounds, amounting on average to more than 95% of the volatile fraction, were identified and quantified by means of GC-MS: one alcohol, four monosulphides, 12 disulphides, seven trisulphides, one tetrasulphide, and two cyclic vinyldithiins. Compound names, working tags, retention indices, absolute amount ranges of individual compounds and different chemical classes are reported in Table 3 whereas Table 4 shows the total and relative volatile content.…”

Section: Alk(en)yl Cysteine Sulphoxides (Acsos)mentioning

confidence: 99%

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Non‐volatile cysteine sulphoxides and volatile organosulphur compounds in cloves of garlic (Allium sativum L.) and elephant garlic (Allium ampeloprasum L.) local accessions from northern and central Italy

2022

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BACKGROUND Garlic (Allium sativum L.) and other species of genus Allium are popular vegetables and food seasonings, owing to their spicy flavour and richness in health‐promoting compounds. Several local garlic types are still grown on a small scale in different Italian regions, not being however yet properly characterized for their chemical composition. RESULTS In the present investigation ten garlic and four elephant garlic (Allium ampeloprasum L.) populations cultivated in northern and central Italy were evaluated for their alk(en)yl cysteine sulphoxide (ACSO) and volatile compound profiles. Three non‐volatile ACSOs (methiin, alliin, and isoalliin) and 27 volatile compounds were identified and quantified. A high and significant within‐type variability was detected, with total ACSOs in the range 2759–5756, 4533–15 520, and 6565–10 643 mg kg−1 of fresh weight (f.w.). in elephant, white and red garlic, respectively. Elephant garlic showed a total sulphoxide content and a relative alliin amount significantly lower than white and red garlic. Remarkable within‐type differences were also assessed for volatile compound content, ranging 260–599, 333–981, and 618–845 mg kg−1 f.w. in elephant, white, and red garlic, respectively. Diallyl trisulphide was the major individual compound, accounting for more than 0.30 mg mg−1 of volatiles in all the analysed samples. The three garlic types were clearly separated by discriminant analysis of analytical traits. CONCLUSION This study investigated for the first time different Italian garlic and elephant garlic populations with respect to non‐volatile and volatile organosulphur compound content, allowing the possibility of selecting garlic accessions according to the bioactive content. © 2022 Society of Chemical Industry.

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Section: Resultssupporting

confidence: 87%

Section: Alk(en)yl Cysteine Sulphoxides (Acsos)mentioning

confidence: 99%

Non‐volatile cysteine sulphoxides and volatile organosulphur compounds in cloves of garlic (Allium sativum L.) and elephant garlic (Allium ampeloprasum L.) local accessions from northern and central Italy

2022

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“…In Allium , over half of the total sulfur content within the mature garlic bulb is found in the form of S -alk(en)yl cysteine sulfoxides (ASCOs) ( 69 ), non-protein sulfur amino acids which are converted to their respective thiosulfinates or propanethial- S -oxide upon tissue damage ( 70 ).…”

Section: Dietary Sources and Chemical Nature Of Oscsmentioning

confidence: 99%

“…When the bulbs are cut, crushed, chopped or chewed, the enzyme alliinase (a vacuolar lyase) is released from vacuoles and catalyzes the formation of sulfenic acids from l-cysteine sulfoxides: S -allyl-l-cysteine sulfoxide (alliin); S -methyl-l-cysteine sulfoxide (methiin); S -propyl-l-cysteine sulfoxide (propiin); S - trans -1-propenyl-l-cysteine sulfoxide (isoallin) ( 71 , 72 ). Sulfenic acids spontaneously react with each other to form unstable compounds called thiosulfinates ( 69 ): eg. alliin is converted into allicin (alkenyl alkene thiosulfinate - diallyl thiosulfinate).…”

Section: Dietary Sources and Chemical Nature Of Oscsmentioning

confidence: 99%

Dietary organosulfur compounds: Emerging players in the regulation of bone homeostasis by plant-derived molecules

2022

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The progressive decline of bone mass and the deterioration of bone microarchitecture are hallmarks of the bone aging. The resulting increase in bone fragility is the leading cause of bone fractures, a major cause of disability. As the frontline pharmacological treatments for osteoporosis suffer from low patients' adherence and occasional side effects, the importance of diet regimens for the prevention of excessive bone fragility has been increasingly recognized. Indeed, certain diet components have been already associated to a reduced fracture risk. Organosulfur compounds are a broad class of molecules containing sulfur. Among them, several molecules of potential therapeutic interest are found in edible plants belonging to the Allium and Brassica botanical genera. Polysulfides derived from Alliaceae and isothiocyanates derived from Brassicaceae hold remarkable nutraceutical potential as antiinflammatory, antioxidants, vasorelaxant and hypolipemic. Some of these effects are linked to the ability to release the gasotrasmitter hydrogen sulfide (H 2 S). Recent preclinical studies have investigated the effect of organosulfur compounds in bone wasting and metabolic bone diseases, revealing a strong potential to preserve skeletal health by exerting cytoprotection and stimulating the bone forming activity by osteoblasts and attenuating bone resorption by osteoclasts. This review is intended for revising evidence from preclinical and epidemiological studies on the skeletal effects of organosulfur molecules of dietary origin, with emphasis on the direct regulation of bone cells by plantderived polysulfides, glucosinolates and isothiocyanates. Moreover, we highlight the potential molecular mechanisms underlying the biological role of these compounds and revise the importance of the so-called 'H 2 S-system' on the regulation of bone homeostasis.

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“…Both are soluble in polar solvents (log P of −1.93 and 0.03, respectively) being commonly extracted with water, ethanol, and methanol. 10,18,19 Different extraction techniques have been applied to extract organosulphur compounds from garlic (bulb, clove, and leaf), from traditional ones like maceration and reflux extraction (using water, ethanol, and acidic methanol-water mixture) to advanced technologies such as pressurised liquid extraction (ethanol), supercritical fluid extraction (CO 2 ), microwave-assisted extraction (water), and ultrasoundassisted extraction (water and ethanol). 15 Conventional techniques are in general terms laborious and time-consuming, requiring large solvent volumes (sometimes toxic ones), and the yield levels are mostly lower than the ones obtained with advanced technologies, which have drastically reduced the extraction time and the amount of solvent required.…”

Section: Introductionmentioning

confidence: 99%

Chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic (Allium ampeloprasum L.) by liquid chromatography tandem mass spectrometry

Peterssen-Fonseca

Henriquez‐Aedo

Carrasco-Sandoval

et al. 2021

Phytochemical Analysis

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Introduction: Giant garlic is a functional food that contains different kinds of bioactive molecules with beneficial effects on chronic noncommunicable diseases like diabetes and cardiovascular conditions. Considering biosynthesis pathways, abundance, and biological activity, alliin and S-allyl-cysteine were used as chemical markers of organosulphur compounds present in giant garlic.Objective: To establish a chemometric optimisation of pressurised liquid extraction for the determination of alliin and S-allyl-cysteine in giant garlic by liquid chromatography tandem mass spectrometry (LC-MS/MS).Methodology: Samples were blanched (ca. 90 C for 10 min) to inactivate alliinase and γ-glutamyl transpeptidase enzymes and then freeze-dried. Chemometric optimisation was performed via response surface methodology based on central composite design (CCD). Organosulphur compound yields were determined applying a validated LC-MS/MS method in multiple reaction monitoring (MRM) mode using the following transitions: for alliin m/z 178 ! 74 and for S-allyl-cysteine m/z 162 ! 41.Results: According to CCD results, under constant conditions of pressure (1500 psi) and time (20 min), the optimal conditions for pressurised liquid extraction of alliin and S-allyl-cysteine were 70.75 and 68.97% v/v of ethanol in extraction solvent and 76.45 and 98.88 C as extraction temperature, respectively. Multiple response optimisation for the simultaneous extraction of both organosulphur compounds was established via desirability function. Under these conditions, 2.70 ± 0.27 mg g −1 dry weight (DW) of alliin and 2.79 ± 0.22 mg g −1 DW of S-allyl-cysteine were extracted.Conclusions: These results clearly demonstrated that pressurised liquid extraction is an efficient green technique to extract bioactive organosulphur compounds from giant garlic. Extraction yields were significantly (p < 0.05) higher than those obtained with conventional ultra-turrax extraction.

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Variability in S-Alk(en)yl-l-Cysteine Sulfoxides in Garlic within a Seven-Month Period Determined by a Liquid Chromatography – Tandem Mass Spectrometry Method

Cited by 8 publications

References 28 publications

Non‐volatile cysteine sulphoxides and volatile organosulphur compounds in cloves of garlic (Allium sativum L.) and elephant garlic (Allium ampeloprasum L.) local accessions from northern and central Italy

Non‐volatile cysteine sulphoxides and volatile organosulphur compounds in cloves of garlic (Allium sativum L.) and elephant garlic (Allium ampeloprasum L.) local accessions from northern and central Italy

Dietary organosulfur compounds: Emerging players in the regulation of bone homeostasis by plant-derived molecules

Chemometric optimisation of pressurised liquid extraction for the determination of alliin and S‐allyl‐cysteine in giant garlic (Allium ampeloprasum L.) by liquid chromatography tandem mass spectrometry

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