Expeditious and sustainable two-step synthesis of sinapoyl-<scp>l</scp>-malate and analogues: towards non-endocrine disruptive bio-based and water-soluble bioactive compounds

Peyrot, Cédric; Mention, Matthieu M.; Fournier, R.; Brunissen, Fanny; Couvreur, Julien; Balaguer, Patrick; Allais, Florent

doi:10.1039/d0gc02763d

Cited by 22 publications

(27 citation statements)

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“…Several works have shown that SADs can be used as antioxidant molecules for different applications [ 3 , 35 , 36 ]. Figure 4 shows the antioxidant activity of the various extracts, measured by the DPPH radical scavenging method, expressed in mg of Trolox equivalent per 100 g DM .…”

Section: Resultsmentioning

confidence: 99%

Selective Extraction of Sinapic Acid Derivatives from Mustard Seed Meal by Acting on pH: Toward a High Antioxidant Activity Rich Extract

et al. 2021

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The aim of this paper is to study the effect of the pH on the extraction of sinapic acid and its derivatives from mustard seed meal. Solutions of acidic pH (pH 2), basic pH (pH 12) and distilled water (uncontrolled pH ~ 4.5) were tested at different percentages of ethanol. The maximum extraction yield for sinapic acid (13.22 µmol/g of dry matter (DM)) was obtained with a buffered aqueous solution at pH 12. For ethyl sinapate, the maximum extraction yield reached 9.81 µmol/g DM with 70% ethanol/buffered aqueous solution at pH 12. The maximum extraction yield of sinapine (15.73 µmol/g DM) was achieved with 70% ethanol/buffered aqueous solution at pH 2. The antioxidant activity of each extract was assessed by DPPH assay; the results indicated that the extracts obtained at pH 12 and at low ethanol percentages (<50%) exhibit a higher antioxidant activity than extracts obtained at acidic conditions. Maximum antioxidant activity was reached at pH 12 with buffer solution (11.37 mg of Trolox Equivalent/g DM), which confirms that sinapic acid-rich fractions exhibit a higher antioxidant activity. Thus, to obtain rich antioxidant extracts, it is suggested to promote the presence of sinapic acid in the extracts.

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Section: Resultsmentioning

confidence: 99%

Selective Extraction of Sinapic Acid Derivatives from Mustard Seed Meal by Acting on pH: Toward a High Antioxidant Activity Rich Extract

et al. 2021

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“…Inhibition of a broad range of Gram-negative and Gram-positive bacteria have also been demonstrated using a SinA fraction isolated from the ethanolic extract of rapeseed (Nowak et al, 1992). The antimicrobial activities of sinapine (Mouterde et al, 2020) and other SinEs (Peyrot et al, 2020b) against Escherichia coli have also been recently highlighted. These literature reports strongly suggest that SinA and its derivatives are potential biobased antimicrobial reagents.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…Although pure final product was obtained with a decent yield, the extensive use of toxic solvents along with multiple protection/deprotection steps throughout the pathway will likely hinder of the application of this approach at multigramscales. With this in mind, Peyrot et al have devised a more sustainable and straightforward, protecting group-free procedure based on the Knoevenagel-Doebner condensation of syringaldehyde (12) and malic monomalonate ester (Figure 15) (Peyrot et al, 2020b). Sinapoyl malate and analogues were thereby obtained in higher yields.…”

Section: Sinapoyl Glucosementioning

confidence: 99%

“…Sinapine, on the other hand, exhibits even higher antioxidant activity than SinA (Thiyam et al, 2006). The antioxidant activities of sinapoyl malate and sinapoyl glucose were reported to be comparable to conventional antioxidants such as butylated hydroxyanisol (BHA), butylated hydroxytoluene (BHT), or trolox (Thiyam et al, 2006;Peyrot et al, 2020b). In addition, antioxidant activity of Canola meal extract was also studied by Hussain et al (Hussain et al, 2020).…”

Section: Antioxidant Activitymentioning

confidence: 99%

“…As prominent p-hydroxycinnamic acid, SinA and its derivatives also exhibit high photo-stability and UV-absorption (Dean et al, 2014;Horbury et al, 2019;Peyrot et al, 2020a). The photophysical properties of numerous synthetic SinEs were recently studied by Peyrot et al (Peyrot et al, 2020a;Peyrot et al, 2020b) who have reported comparable, or even better, photo-activities of these synthetic p-hydroxycinnamic acids than octinoxate (a conventional fossil-based UV-filter reagent) in term of UV absorption and photostability.…”

Section: Uv-filter Activitiesmentioning

confidence: 99%

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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

et al. 2021

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Sinapic acid (SinA) and corresponding esters are secondary metabolites abundantly found in plants of Brassica family. Belonging to the family of p-hydroxycinnamic acids, SinA and its esters analogues are present in different plant parts and involved in multiple biological processes in planta. Moreover, these metabolites are also found in relatively large quantities in agro-industrial wastes. Nowadays, these metabolites are increasingly drawing attention due to their bioactivities which include antioxidant, anti-microbial, anti-cancer and UV filtering activities. As a result, these metabolites find applications in pharmaceutical, cosmetic and food industries. In this context, this article reviews innate occurrence, biosynthesis, accessibility via chemical synthesis or direct extraction from agro-industrial wastes. Biological activities of SinA and its main corresponding esters will also be discussed.

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Is a Catalyst Always Needed? The Case of the Knoevenagel Reaction with Malononitrile

2022

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Dedicated to Professor Renato Noto on the occasion of his 76 th birthdayThe aim of this Perspective is to start a discussion about the real usefulness of more or less sophisticated catalytic systems for the Knoevenagel reaction with malononitrile, a reaction that can take place under mild conditions without the need of a catalyst. From a sustainable viewpoint the questions are: Is it useful to increase the rate of a reaction that already occurs under mild conditions? Is it useful to spend resources and time in designing, characterizing and realizing complex catalytic systems for such reaction? Does it make sense to carry out the reaction under conditions such as to have a slower reaction rate and therefore to find a catalyst that is able to increase it?

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Expeditious and sustainable two-step synthesis of sinapoyl-l-malate and analogues: towards non-endocrine disruptive bio-based and water-soluble bioactive compounds

Abstract: Straightforward and sustainable two-step route to bioactive sinapoyl-l-malate and analogues using Meldrum's acid opening and Knoevenagel-Doebner condensation.

Cited by 22 publications

References 50 publications

Selective Extraction of Sinapic Acid Derivatives from Mustard Seed Meal by Acting on pH: Toward a High Antioxidant Activity Rich Extract

Selective Extraction of Sinapic Acid Derivatives from Mustard Seed Meal by Acting on pH: Toward a High Antioxidant Activity Rich Extract

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

Is a Catalyst Always Needed? The Case of the Knoevenagel Reaction with Malononitrile

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