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

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


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.

MeSH terms

  • Antioxidants / pharmacology*
  • Brassica napus / chemistry*
  • Dietary Proteins / isolation & purification*
  • Food Handling
  • Phenols / pharmacology*
  • Plant Extracts / pharmacology*
  • Plant Proteins / isolation & purification*
  • Resins, Plant / chemistry*


  • Antioxidants
  • Dietary Proteins
  • Phenols
  • Plant Extracts
  • Plant Proteins
  • Resins, Plant