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. 2021 Sep 27;26(19):5853.
doi: 10.3390/molecules26195853.

Identification and Capture of Phenolic Compounds from a Rapeseed Meal Protein Isolate Production Process By-Product by Macroporous Resin and Valorization Their Antioxidant Properties

Affiliations

Identification and Capture of Phenolic Compounds from a Rapeseed Meal Protein Isolate Production Process By-Product by Macroporous Resin and Valorization Their Antioxidant Properties

Tuong Thi Le et al. Molecules. .

Abstract

In this study, phenolic compounds from an aqueous protein by-product from rapeseed meal (RSM) were identified by HPLC-DAD and HPLC-ESI-MS, including sinapine, sinapic acid, sinapoyl glucose, and 1,2-di-sinapoyl gentibiose. The main phenolic compound in this by-product was sinapine. We also performed acid hydrolysis to convert sinapine, and sinapic acid derivatives present in the permeate, to sinapic acid. The adsorption of phenolic compounds was investigated using five macroporous resins, including XAD4, XAD7, XAD16, XAD1180, and HP20. Among them, XAD16 showed the highest total phenolic contents adsorption capacities. The adsorption behavior of phenolic compounds was described by pseudo-second-order and Langmuir models. Moreover, thermodynamics tests demonstrated that the adsorption process of phenolic compounds was exothermic and spontaneous. The highest desorption ratio was obtained with 30% (v/v) and 70% (v/v) ethanol for sinapine and sinapic acid, respectively, with a desorption ratio of 63.19 ± 0.03% and 94.68 ± 0.013%. DPPH and ABTS tests revealed that the antioxidant activity of the hydrolyzed fraction was higher than the non-hydrolyzed fraction and higher than the one of vitamin C. Antioxidant tests demonstrated that these phenolic compounds could be used as natural antioxidants, which can be applied in the food industry.

Keywords: adsorption; macroporous resin; phenolic compounds; rapeseed meal; sinapic acid; sinapine.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
SE-HPLC chromatogram and structures of phenolic compounds detected in the UF permeate obtained from rapeseed protein purification. Chromatograms were recorded at 325 nm. (A) Non-hydrolyzed phenolic compounds. (B) Kinetic curve of permeate hydrolysis reaction. (C) Hydrolyzed phenolic compounds.
Figure 2
Figure 2
Chemical structures of phenolic compounds (1) Sinapine, (2) sinapoyl glucose, (3) 1,2-disinapoyl gentiobiose, and (4) sinapic acid. Different numbers indicated the position of phenolic compounds presented in the HPLC chromatogram.
Figure 3
Figure 3
Adsorption capacity of phenolic compounds after adsorption of UF permeate without (A) or with acidic hydrolysis (B) using XAD4, XAD16, XAD7, XAD1180, and HP20 resins. Results are given in terms of total phenolic compounds (TPC) and the main phenolic compound of the starting product (sinapine and sinapic acid without and with hydrolysis, respectively).
Figure 4
Figure 4
Adsorption kinetics with XAD16. (A,B) Adsorption kinetic curve. (C,D) Pseudo-first-order model. (E,F) Pseudo-second-order model. (G,H) Intra-particle diffusion model (in linearized forms) of SP and SA in non-hydrolyzed and hydrolyzed permeates, respectively.
Figure 5
Figure 5
Adsorption isotherms of phenolic compounds on XAD16 with Langmuir and Freundlich linear models. (A,B) Langmuir and Freundlich models for sinapine. (C,D) Langmuir and Freundlich models for sinapic acid.
Figure 6
Figure 6
ln KL vs. 1/T plot of adsorption equilibrium constant KL using Langmuir isotherm of (A) Sinapine and (B) Sinapic acid.
Figure 7
Figure 7
Desorption ratio of sinapine (A) and sinapic acid (B) from the XAD16 resin at different ethanol concentrations.
Figure 8
Figure 8
HPLC chromatogram of phenolic compounds in (A) the non-hydrolyzed fraction after desorption with ethanol 30% (v/v) and (B) the hydrolyzed fraction after desorption with ethanol 70% (v/v).
Figure 9
Figure 9
Scavenging activity of the non-hydrolyzed (N fraction) and hydrolyzed (H fraction) fractions compared to pure sinapine, sinapic acid, and vitamin C determined using (A) DPPH assay and (B) ABTS assay. Bars labeled with the different lowercase letters and uppercase letters are significantly different (p < 0.05).

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