Multifunctional compounds in the extract from mature seeds of Vicia faba var. minor: Phytochemical profiling, antioxidant activity and cellular safety in human selected blood cells in in vitro trials

Kowalczyk, Mariusz; Rolnik, Agata; Adach, Weronika; Kluska, Magdalena; Juszczak, M.; Grabarczyk, Łukasz; Woźniak, Katarzyna; Olas, Beata; Stochmal, Anna

doi:10.1016/j.biopha.2021.111718

Cited by 6 publications

(16 citation statements)

References 34 publications

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“…Valente et al reported five derivatives and an unidentified compound that is likely also a vicine derivative [ 30 ]. Compound 33, reported by Valente et al, m / z 387 and its [2M − H] − ion at m / z 775, is identified here as (iso)valeryl vicine (compound 24 , Table 1 ), also identified in [ 29 ]. Compound 59 in Valente et al, m / z 527, is identified here as vicine + C 12 H 16 O 4 (compound 77 , Table 1 ).…”

Section: Discussionmentioning

confidence: 85%

“…The exact m / z of 141.017 and 304.077 allows us to identify convicine, while the remainder of the highest fragment peaks (193.05, 175.04, 160.015, 134.036, and 132.02, Figure 2 ) agree with the MS/MS spectra of a ferulic acid standard and published data on ferulic acid conjugates [ 31 ]. Compound 38 is thus feruloyl convicine (calculated m / z 480.126; Figure 2 , upper spectrum), one of the convicine derivatives previously identified [ 29 ]. The vicine homologue (compound 39 ; m / z 479.140; calculated m / z 479.142) was subsequently identified at a retention time of 19.95 min ( Figure 2 , lower spectrum).…”

Section: Resultsmentioning

confidence: 97%

“…The first group of derivatives in Table 1 (compounds 1 to 25 ) are derivatives found on numerous other groups of biomolecules. They include malonic, (iso)valeric, and benzoic acid, which are relatively common on biomolecules, including on glycosylated flavonoids isolated from Fabaceae [ 33 ]; some of these (con)vicine derivatives were previously tentatively identified in faba bean seeds [ 29 , 30 ]. The identification of these compounds is supported by well-described observations such as the loss of CO 2 from malonyl derivatives in negative mode [ 34 ] or known masses for derivatives (among others, those described in maize [ 35 ]).…”

Section: Discussionmentioning

confidence: 99%

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Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (Vicia faba L.) Cultivars: Insights from LC-MS/MS Spectra

Sergeant,

Goertz,

Halime

et al. 2024

Molecules

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While numerous Fabaceae seeds are a good nutritional source of high-quality protein, the use of some species is hampered by toxic effects caused by exposure to metabolites that accumulate in the seeds. One such species is the faba or broad bean (Vicia faba L.), which accumulates vicine and convicine. These two glycoalkaloids cause favism, the breakdown of red blood cells in persons with a glucose-6-phosphate dehydrogenase deficiency. Because this is the most common enzyme deficiency worldwide, faba bean breeding efforts have focused on developing cultivars with low levels of these alkaloids. Consequently, quantification methods have been developed; however, they quantify vicine and convicine only and not the derivatives of these compounds that potentially generate the same bio-active molecules. Based on the recognition of previously unknown (con)vicine-containing compounds, we screened the fragmentation spectra of LC-MS/MS data from five faba bean cultivars using the characteristic fragments generated by (con)vicine. This resulted in the recognition of more than a hundred derivatives, of which 89 were tentatively identified. (Con)vicine was mainly derivatized through the addition of sugars, hydroxycinnamic acids, and dicarboxylic acids, with a group of compounds composed of two (con)vicine residues linked by dicarboxyl fatty acids. In general, the abundance profiles of the different derivatives in the five cultivars mimicked that of vicine and convicine, but some showed a derivative-specific profile. The description of the (con)vicine diversity will impact the interpretation of future studies on the biosynthesis of (con)vicine, and the content in potentially bio-active alkaloids in faba beans may be higher than that represented by the quantification of vicine and convicine alone.

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Section: Discussionmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

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Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (Vicia faba L.) Cultivars: Insights from LC-MS/MS Spectra

Sergeant,

Goertz,

Halime

et al. 2024

Molecules

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“…In addition, two dihydro ferulic acid derivatives of vicin were detected in Vicia faba var. minor beans by high‐resolution LC–MS/MS analysis (Kowalczyk et al ., 2021).…”

Section: Acylated Polyphenolics Tentatively Identified Via Lc/ms Meta...mentioning

confidence: 99%

Acylated polyphenolics of family Fabaceae: distribution, chemodiversity, and bioactivity, a comprehensive review

Khalil

Sabry

El‐Askary

et al. 2023

Int J of Food Sci Tech

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Polyphenolics are the most common class of plant-derived natural products. They play an important role in the protection of both plants and humans. Acylated polyphenolics, i.e., polyphenolics esterified with either phenolic or organic acids, are abundant in several plant families including Fabaceae. This review article is intended to shed light on the distribution, isolation, chemodiversity, and bioactivity of acylated polyphenolics obtained from selected fabaceous plants mentioned herein. Isolation of these metabolites was mostly performed via successive column chromatography, including preparative and semi-preparative HPLC. Structure elucidation was achieved through interpretation of spectral data. Meanwhile, detection was chiefly accomplished via diverse liquid chromatography/mass spectrometric analyses. Compared to usual polyphenolics, these unique acylated compounds were found of higher stability and bioactivity. The current survey targets to provide a comprehensive overview of the medicinal role of acylated polyphenolics that may encourage the incorporation of fabaceous plants in pharmaceuticals.

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“…In general, only the profile of non-volatile compounds has been studied in faba beans without making a link to their sensory perception. The main identified metabolites belonged to alkaloids, phenolic compounds, saponins, jasmonates, organic acids, and amino acids [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. It has been suggested that the presence of free phenolic compounds, vicine and convicine was linked to bitterness in faba bean ingredients (flour, protein concentrate, and isolate).…”

Section: Introductionmentioning

confidence: 99%

Faba Bean (Vicia faba L. minor) Bitterness: An Untargeted Metabolomic Approach to Highlight the Impact of the Non-Volatile Fraction

Karolkowski,

Meudec,

Bruguière

et al. 2023

Metabolites

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In the context of climate change, faba beans are an interesting alternative to animal proteins but are characterised by off-notes and bitterness that decrease consumer acceptability. However, research on pulse bitterness is often limited to soybeans and peas. This study aimed to highlight potential bitter non-volatile compounds in faba beans. First, the bitterness of flours and air-classified fractions (starch and protein) of three faba bean cultivars was evaluated by a trained panel. The fractions from the high-alkaloid cultivars and the protein fractions exhibited higher bitter intensity. Second, an untargeted metabolomic approach using ultra-high-performance liquid chromatography–diode array detector–tandem–high resolution mass spectrometry (UHPLC–DAD–HRMS) was correlated with the bitter perception of the fractions. Third, 42 tentatively identified non-volatile compounds were associated with faba bean bitterness by correlated sensory and metabolomic data. These compounds mainly belonged to different chemical classes such as alkaloids, amino acids, phenolic compounds, organic acids, and terpenoids. This research provided a better understanding of the molecules responsible for bitterness in faba beans and the impact of cultivar and air-classification on the bitter content. The bitter character of these highlighted compounds needs to be confirmed by sensory and/or cellular analyses to identify removal or masking strategies.

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Multifunctional compounds in the extract from mature seeds of Vicia faba var. minor: Phytochemical profiling, antioxidant activity and cellular safety in human selected blood cells in in vitro trials

Cited by 6 publications

References 34 publications

Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (Vicia faba L.) Cultivars: Insights from LC-MS/MS Spectra

Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (Vicia faba L.) Cultivars: Insights from LC-MS/MS Spectra

Acylated polyphenolics of family Fabaceae: distribution, chemodiversity, and bioactivity, a comprehensive review

Faba Bean (Vicia faba L. minor) Bitterness: An Untargeted Metabolomic Approach to Highlight the Impact of the Non-Volatile Fraction

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