Sinapic Acid

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Pierre Villeneuve - One of the best experts on this subject based on the ideXlab platform.

  • effect of Sinapic Acid ester derivatives on the oxidative stability of omega 3 fatty Acids rich oil in water emulsions
    Food Chemistry, 2020
    Co-Authors: Tayse Ferreira Ferreira Da Silveira, Pierre Villeneuve, Leticia Maeda Cajaiba, Leonardo Valentin, Bruno Barea, Inar Alves De Castro
    Abstract:

    Oil-in-water (O/W) emulsions are important delivery systems of omega-3 fatty Acids (n-3 FA). We investigated the effect of Sinapic Acid esters concentration and chain length, the electrical charge of the emulsifier and emulsion pH on the oxidative stability of n-3 FA rich O/W emulsions. Echium oil was applied as n-3 FA source. A 24 factorial design was used to simultaneously evaluate these factors. Peroxide value, malondialdehyde, 2,4-heptadienal and 2,4-decadienal were measured in the emulsions. pH and the electrical charge of the emulsifier modulated the antioxidant effectiveness of Sinapic Acid esters, while concentration was not relevant. The combination of positively charged emulsifier with neutral pH provided the best oxidative stability for echium oil emulsions. Our results also suggested that the increase of length chain of Sinapic Acid, from C4 to C12, reduced the secondary products of oxidation, when echium oil emulsions were prepared using negatively charged emulsifier under Acidic conditions.

  • Influence of rapeseed meal treatments on its total phenolic content and composition in sinapine, Sinapic Acid and canolol
    Industrial Crops and Products, 2017
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105 degrees-160 degrees C) or microwave roasting (160 degrees-180 degrees C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.

  • influence of rapeseed meal treatments on its total phenolic content and composition in sinapine Sinapic Acid and canolol
    Industrial Crops and Products, 2015
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Abstract Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105°–160 °C) or microwave roasting (160°–180 °C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.

Brian E Ellis - One of the best experts on this subject based on the ideXlab platform.

  • enzymology of udp glucose Sinapic Acid glucosyltransferase from brassica napus
    Phytochemistry, 1998
    Co-Authors: Shawn X Wang, Brian E Ellis
    Abstract:

    UDP-glucose:Sinapic Acid glucosyltransferase (SGT; EC 2.4.1.120) was purified from 60-h-old seedlings of Brassica napus. The purified SGT appears to be a cytosolic monomeric polypeptide with a Mr of 42 kDa and a pI of 5. Kinetic analysis suggested that the catalytic mechanism used by SGT best fits a ‘‘random bi–bi’’ model, with a Km (UDP-glucose) of 2.4 mM and Km (Sinapic Acid) of 0.16 mM. SGT also catalyzes the reverse reaction in vitro, using UDP and sinapoylglucose to form UDP-glucose. No cofactors are required for enzyme activity, but reducing agents and glycerol are required to stabilize the activity. The enzyme is strongly inhibited by p-OH-mercuribenzoic Acid, UDP, TDP, Zn++, Cu++ and Hg++.

Erika Zago - One of the best experts on this subject based on the ideXlab platform.

  • Influence of rapeseed meal treatments on its total phenolic content and composition in sinapine, Sinapic Acid and canolol
    Industrial Crops and Products, 2017
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105 degrees-160 degrees C) or microwave roasting (160 degrees-180 degrees C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.

  • influence of rapeseed meal treatments on its total phenolic content and composition in sinapine Sinapic Acid and canolol
    Industrial Crops and Products, 2015
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Abstract Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105°–160 °C) or microwave roasting (160°–180 °C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.

James L Charlton - One of the best experts on this subject based on the ideXlab platform.

  • structural changes of Sinapic Acid during alkali induced air oxidation and the development of colored substances
    Journal of the American Oil Chemists' Society, 1999
    Co-Authors: S D Arntfield, James L Charlton
    Abstract:

    Structural changes of Sinapic Acid were induced by air oxidation in aqueous solutions at pH 7–10 and followed by spectral and high-performance liquid chromatographic (HPLC) analysis. Color properties of the Sinapic Acid solutions were determined by taking the transmittance spectra, calculating the Commission Internationale de l’Eclairage (CIE) 1931 tristimulus values, and converting to Hunter L a b values. Reaction rate constants for Sinapic Acid were determined by a kinetic study based on the quantitative results from HPLC analysis. These reactions were first order with respect to Sinapic Acid and fit the appropriate equation with a coefficient of R 2 >0.97. Sinapic Acid was converted to thomasidioic Acid with reaction rate constants (k) of 8.54×10−6, 2.51×10−5, and 4.87×10−5 s−1 in phosphate-boric Acid buffers of pH 7, 8.5, and 10, respectively. Similar reactions in ammonium bicarbonate buffers were more than 10 times faster. With time, thomasidioic Acid further converted to 2,6-dimethoxy-p-benzoquinone and 6-hydroxy-5,7-dimethoxy-2-naphthoic Acid. Air oxidation of Sinapic Acid aqueous solutions caused darkening of the color for the system, with the 2,6-dimethoxy-p-benzoquinone as a major color contributor.

  • structural changes of Sinapic Acid and sinapine bisulfate during autoclaving with respect to the development of colored substances
    Journal of the American Oil Chemists' Society, 1999
    Co-Authors: S D Arntfield, James L Charlton
    Abstract:

    Structural changes in Sinapic Acid during autoclaving were studied using spectral analysis, thin-layer chromatography, high-performance liquid chromatography, nuclear magnetic resonance (NMR), and mass spectroscopy. Color properties of Sinapic Acid and its derivatives were studied by determining the transmittance spectrum, calculating the Commission Internationale de l’Eclairage 1931 tristimulus values and converting to Hunter L a b values. It was found that the colorless Sinapic Acid aqueous solution (100 µg/mL) turned yellow after 15 min in an autoclave at 121°C and 0.1 MPa. Filtering the yellow aqueous solution through a 0.45-µm filter removed a brown solid consisting of at least three undetermined colored substances and left a yellow liquid. A newly developed yellow substance, syringaldehyde, was identified in the liquid phase by comparing the NMR and mass spectra of the unknown with those of authentic syringaldehyde. Thomasidioic Acid was also found in the liquid phase. Under the same autoclaving conditions, sinapine bisulfate showed no evidence of any structural or color changes.

  • evaluation of alkaline conversion of Sinapic Acid to thomasidioic Acid
    Journal of Agricultural and Food Chemistry, 1996
    Co-Authors: Maria Rubino, S D Arntfield, James L Charlton
    Abstract:

    Conditions which promote the alkaline conversion of Sinapic Acid (SA), the main phenolic Acid in canola, to the lignan thomasidioic Acid (TA) were investigated as the presence of TA could affect nutritional and functional properties of canola products. Reaction rates were studied using ultraviolet spectroscopy under oxygen, nitrogen, and air and in the presence of antioxidants. High-pressure liquid chromatography was used to quantify the conversion of SA to TA. This reaction appears to involve an oxidative coupling of SA molecules which can be controlled by purging with nitrogen. By including ascorbic Acid, the reaction was slowed but not completely controlled, and the presence of sodium bisulfite accelerated the reaction.In the presence of air, there was complete conversion of SA to TA at pH 8.5 and 30% conversion at pH 7. Keywords: Phenolic Acids; Sinapic Acid; thomasidioic Acid; reaction rate; alkali

  • conversion of phenolics to lignans Sinapic Acid to thomasidioic Acid
    Journal of the American Oil Chemists' Society, 1995
    Co-Authors: Maria Rubino, S D Arntfield, James L Charlton
    Abstract:

    Changes in Sinapic Acid when exposed to aqueous alkaline conditions were elucidated. Sinapic Acid was exposed to a volatile buffer (pH 8.5) for 24 h, lyophilized, Acidified, extracted, and characterized using nuclear magnetic resonance and mass spectroscopy. The product obtained was identified as the lignan thomasidioic Acid. This identification was confirmed by comparison with a synthesized authentic sample of thomasidioic Acid. Conversion of Sinapic Acid to thomasidioic Acid under alkaline conditions previously has not been reported. Thomasidioic Acid was present after exposure of Sinapic Acid to pH 8.5 for as few as 6 h. Thomasidioic Acid also was formed at pH 7.

Frédéric Fine - One of the best experts on this subject based on the ideXlab platform.

  • Influence of rapeseed meal treatments on its total phenolic content and composition in sinapine, Sinapic Acid and canolol
    Industrial Crops and Products, 2017
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105 degrees-160 degrees C) or microwave roasting (160 degrees-180 degrees C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.

  • influence of rapeseed meal treatments on its total phenolic content and composition in sinapine Sinapic Acid and canolol
    Industrial Crops and Products, 2015
    Co-Authors: Erika Zago, CHAHINAZ AOUF, Jérôme Lecomte, Nathalie Barouh, Frédéric Fine, Patrick Carré, Pierre Villeneuve
    Abstract:

    Abstract Rapeseed meal is the co-product of the pressing and de-oiling process of rapeseed seeds and is used as animal feed. Most of phenolic compounds remain in the meal after processing the seeds. While sinapine (sinapoyl choline), sinapoyl glucose and Sinapic Acid are naturally present in the seed, canolol (4-vinylsyringol) is formed during processes of pressing, oil extraction and roasting treatments via decarboxylation of Sinapic Acid. Canolol was recently described as a free-radical scavenger with various biological activities. One of the objectives of this work was the valorization of rapeseed meal as a source of canolol, this latter being produced through the transformation of sinapine and Sinapic Acid under hydration and roasting processes applicable at industrial scale. The parameters studied for the rapeseed meal processing were: (i) time of incubation after hydration: 0, 2 and 18 h and, (ii) thermal treatment: high-temperature steam (105°–160 °C) or microwave roasting (160°–180 °C). It was concluded that temperature, and exposure time in case of microwaves, were the most important factors in increasing concentrations of canolol in rapeseed meal. Incubation time after hydration did not influence the total phenolic compounds content suggesting the absence of endogenous enzymatic hydrolysis. However, it showed a particular contribution in sinapine, Sinapic Acid and canolol transformation during the microwave treatment. Finally, whatever the treatment, only a part of the Sinapic Acid initially present or generated during the processes, was converted into canolol.