Sinapic Acid and Sinapate Esters in Brassica: Innate Accumulation, Biosynthesis, Accessibility via Chemical Synthesis or Recovery From Biomass, and Biological Activities

Nguyen, Vien; Stewart, Jon D.; Ioannou, Irina; Allais, Florent

doi:10.3389/fchem.2021.664602

Cited by 43 publications

(38 citation statements)

References 111 publications

(169 reference statements)

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“…'Rambo'), white mustard (Sinapis alba L.), and red cabbage (Brassica rapa L., var. capitata) are rich in two major groups of phenolic compounds: glycosylated flavonols and hydroxycinnamic acid derivatives (mainly represented by kaempferol and sinapic acid derivatives) [5,6]. These compounds have been associated with radical scavenging activities at the intracellular level, eliminating reactive oxygen species (ROS) and thus preventing deleterious effects associated with oxidative stress [7].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Evidence on Bioaccessibility of Flavonols and Cinnamoyl Derivatives of Cruciferous Sprouts

et al. 2021

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Cruciferous sprouts are rising in popularity as a hallmark of healthy diets, partially because of their phytochemical composition, characterized by the presence of flavonols and cinnamates. However, to shed light on their biological activity, the ability to assimilate (poly)phenols from sprouts (bioaccessible fraction) during gastrointestinal digestion needs to be studied. In this frame, the present work studies the effect of the physicochemical and enzymatic characteristics of gastrointestinal digestion on flavonols and cinnamoyl derivatives, by a simulated static in vitro model, on different cruciferous (red radish, red cabbage, broccoli, and white mustard) sprouts. The results indicate that, although the initial concentrations of phenolic acids in red radish (64.25 mg/g fresh weight (fw)) are lower than in the other sprouts studied, their bioaccessibility after digestion is higher (90.40 mg/g fw), followed by red cabbage (72.52 mg/g fw), white mustard (58.72 mg/g fw), and broccoli (35.59 mg/g fw). These results indicate that the bioaccessibility of (poly)phenols is not exclusively associated with the initial concentration in the raw material, but that the physico-chemical properties of the food matrix, the presence of other additional molecules, and the specific characteristics of digestion are relevant factors in their assimilation.

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Section: Introductionmentioning

confidence: 99%

In Vitro Evidence on Bioaccessibility of Flavonols and Cinnamoyl Derivatives of Cruciferous Sprouts

et al. 2021

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“…Sinapic acid may be found in free form or esterified like other HCAs. These esters can be sugar conjugates (glycosides) such as sinapoyl glucose (identified in this study), or conjugates of other compounds, such as sinapoyl malate (identified in this study) and sinapoyl choline or sinapine (a source of sinapic acid and choline in germinating mustard seed) [ 39 , 40 , 41 , 42 ]. Tinte et al [ 11 ] also identified sinapic acid, sinapoyl glucose and sinapoyl malate in Arabidopsis after treatment with LPS from B. cepacia Furthermore, the antibacterial activity of sinapic acid against both Gram-positive and Gram-negative bacteria have been reported in mustard seeds [ 43 , 44 ].…”

Section: Discussionmentioning

confidence: 99%

Untargeted Metabolomics Profiling of Arabidopsis WT, lbr-2-2 and bak1-4 Mutants Following Treatment with Two LPS Chemotypes

et al. 2022

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Plants perceive pathogenic threats from the environment that have evaded preformed barriers through pattern recognition receptors (PRRs) that recognise microbe-associated molecular patterns (MAMPs). The perception of and triggered defence to lipopolysaccharides (LPSs) as a MAMP is well-studied in mammals, but little is known in plants, including the PRR(s). Understanding LPS-induced secondary metabolites and perturbed metabolic pathways in Arabidopsis will be key to generating disease-resistant plants and improving global plant crop yield. Recently, Arabidopsis LPS-binding protein (LBP) and bactericidal/permeability-increasing protein (BPI)-related proteins (LBP/BPI related-1) and (LBP/BPI related-2) were shown to perceive LPS from Pseudomonas aeruginosa and trigger defence responses. In turn, brassinosteroid insensitive 1 (BRI1)-associated receptor kinase 1 (BAK1) is a well-established co-receptor for several defence-related PRRs in plants. Due to the lack of knowledge pertaining to LPS perception in plants and given the involvement of the afore-mentioned proteins in MAMPs recognition, in this study, Arabidopsis wild type (WT) and mutant (lbr2-2 and bak1-4) plants were pressure-infiltrated with LPSs purified from Pseudomonas syringae pv. tomato DC3000 (Pst) and Xanthomonas campestris pv. campestris 8004 (Xcc). Metabolites were extracted from the leaves at four time points over a 24 h period and analysed by UHPLC-MS, generating distinct metabolite profiles. Data analysed using unsupervised and supervised multivariate data analysis (MVDA) tools generated results that reflected time- and treatment-related variations after both LPS chemotypes treatments. Forty-five significant metabolites were putatively annotated and belong to the following groups: glucosinolates, hydroxycinnamic acid derivatives, flavonoids, lignans, lipids, oxylipins, arabidopsides and phytohormones, while metabolic pathway analysis (MetPA) showed enrichment of flavone and flavanol biosynthesis, phenylpropanoid biosynthesis, alpha-linolenic acid metabolism and glucosinolate biosynthesis. Distinct metabolite accumulations depended on the LPS chemotype and the genetic background of the lbr2-2 and bak1-4 mutants. This study highlights the role of LPSs in the reprogramming Arabidopsis metabolism into a defensive state, and the possible role of LBR and BAK1 proteins in LPSs perception and thus plant defence against pathogenic bacteria.

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“…The available experience demonstrated the capacity of this material to induce anti-cancer, anti-inflammatory, and/or modulatory effects on metabolic processes in different cell systems [ 5 , 10 , 11 , 12 ], focusing the attention on the organosulfur biocomponents to drive the fine-tuning of the processing methods [ 13 ]. The health-promoting activity is commonly ascribed, not only to a single compound, but also to a group of bioactive phytochemicals in the food matrix (e.g., kaempferol glycosides or hydroxycinnamic acid derivatives [ 14 , 15 ]) that may contribute to the capacity to scavenge reactive oxygen species (ROS) and, thus, reducing oxidative stress and mutagenic events [ 16 ]. Indeed, both types of compounds (organosulfur and phenolics) provide complementary bioactivities that boost the final health benefits of cruciferous foods [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

A New Food Ingredient Rich in Bioaccessible (Poly)Phenols (and Glucosinolates) Obtained from Stabilized Broccoli Stalks

Costa-Pérez

Moreno

Periago

et al. 2022

Foods

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Broccoli (Brassica oleracea var. italica) stalks account for up to 35% of the broccoli harvest remains with the concomitant generation of unused waste that needs recovery to contribute to the sustainability of the system. However, due to its phytochemical composition, rich in bioactive (poly)phenols and glucosinolates, as well as other nutrients, the development of valorization alternatives as a source of functional ingredients must be considered. In this situation, the present work aims to develop/obtain a new ingredient rich in bioactive compounds from broccoli, stabilizing them and reducing their degradation to further guarantee a high bioaccessibility, which has also been studied. The phytochemical profile of lyophilized and thermally treated (low-temperature and descending gradient temperature treatments), together with the digested materials (simulated static in vitro digestion) were analysed by HPLC-PDA-ESI-MSn and UHPLC-3Q-MS/MS. Broccoli stalks and co-products were featured by containing phenolic compounds (mainly hydroxycinnamic acid derivatives and glycosylated flavonols) and glucosinolates. The highest content of organosulfur compounds corresponding to the cores of the broccoli stalks treated by applying a drying descendant temperature gradient (aliphatic 18.05 g/kg dw and indolic 1.61 g/kg dw, on average, while the breakdown products were more abundant in the bark ongoing low temperature drying 11.29 g/kg dw, on average). On the other hand, for phenolics, feruloylquinic, and sinapoylquinic acid derivatives of complete broccoli stalk and bark, were more abundant when applying low-temperature drying (14.48 and 28.22 g/kg dw, on average, respectively), while higher concentrations were found in the core treated with decreasing temperature gradients (9.99 and 26.26 g/kg dw, on average, respectively). When analysing the bioaccessibility of these compounds, it was found that low-temperature stabilization of the core samples provided the material with the highest content of bioactives including antioxidant phenolics (13.6 and 33.9 g/kg dw of feruloylquinic and sinapoylquinic acids, on average, respectively) and sulforaphane (4.1 g/kg dw, on average). These processing options enabled us to obtain a new product or ingredient rich in bioactive and bioaccessible compounds based on broccoli stalks with the potential for antioxidant and anti-inflammatory capacities of interest.

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Sinapic Acid and Sinapate Esters in Brassica: Innate Accumulation, Biosynthesis, Accessibility via Chemical Synthesis or Recovery From Biomass, and Biological Activities

Cited by 43 publications

References 111 publications

In Vitro Evidence on Bioaccessibility of Flavonols and Cinnamoyl Derivatives of Cruciferous Sprouts

In Vitro Evidence on Bioaccessibility of Flavonols and Cinnamoyl Derivatives of Cruciferous Sprouts

Untargeted Metabolomics Profiling of Arabidopsis WT, lbr-2-2 and bak1-4 Mutants Following Treatment with Two LPS Chemotypes

A New Food Ingredient Rich in Bioaccessible (Poly)Phenols (and Glucosinolates) Obtained from Stabilized Broccoli Stalks

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