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. 2021 May 17;10(5):1109.
doi: 10.3390/foods10051109.

Highland Barley and Its By-Products Enriched with Phenolic Compounds for Inhibition of Pyrraline Formation by Scavenging α-Dicarbonyl Compounds

Dianwei Zhang  1 , Pei Zhu  1 , Luxuan Han  1 , Xiaomo Chen  1 , Huilin Liu  1 , Baoguo Sun  1
Affiliations

Highland Barley and Its By-Products Enriched with Phenolic Compounds for Inhibition of Pyrraline Formation by Scavenging α-Dicarbonyl Compounds

Dianwei Zhang et al. Foods. .

Abstract

Pyrraline, a typical kind of advanced glycation end product, has been found to contribute to the development of pathologies associated with ageing and diabetes mellitus. In the study, phenolic compounds extracted from highland barley whole grain (HBWG) and vinasse (HBVN) were used to inhibit pyrraline formation in a simulated food. The optimal extraction condition for HBWG and HBVN was using 8 mL of 50% acetone solution at 50 °C for 60 min. The extraction and identification of phenolic compounds from HBWG and HBVN were performed by UPLC-PAD-MS/MS. The inhibitory effects of pyrraline in the simulated food were 52.03% and 49.22% by HBVN and HBWG, respectively. The diphenyl picrylhydrazyl radical- and ferric-reducing ability of plasma assays was used to evaluate the antioxidant activity of the extracts. The main inhibition pathways and molecular mechanism of phenolic compounds on pyrraline regulation were explored by scavenging α-dicarbonyl compounds. The study demonstrated that highland barley and its by-products can potentially be used as a functional food to regulate pyrraline formation during food processing.

Keywords: 3-deoxyglucosone; advanced glycation end products; glyoxal; methylglyoxal.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Extraction conditions of HBWG using the total phenolic compounds as the evaluation criterion. (A) Solvent, (B) Times, (C) Temperature, (D) Volume, and (E) Time. Error bars are standard deviations (n = 3). Different letters above the columns represent significant difference at p < 0.05.
Figure 2
Figure 2
Evaluation of the antioxidant activity of HBWG and fresh and dry HBVN using the FRAP and DPPH methods. Error bars are standard deviations (n = 3). Different letters above the columns represent significant difference at p < 0.05.
Figure 3
Figure 3
Inhibitory effect of HBWG and fresh and dry HBVN on pyrraline formation. Marker. Error bars are standard deviations (n = 3). Different letters above the columns represent significant difference at p < 0.05.
Figure 4
Figure 4
UPLC chromatographic separation of phenolic compounds from HBWG.
Figure 5
Figure 5
Identification of 14 kinds of compounds from HBWG by UHPLC–PAD–MS/MS. (a) UPLC chromatogram of galactonic acid, (a-1) MS for galactonic acid, (b) UPLC chromatogram of malic acid, (b-1) MS for malic acid, (c) UPLC chromatogram of citric acid, (c-1) MS for citric acid, (d) UPLC chromatogram of tiliroside, (d-1) MS for tiliroside.
Figure 6
Figure 6
UPLC chromatographic separation of phenolic compounds from HBVN.
Figure 7
Figure 7
Identification of 21 kinds of compounds from HBVN by UHPLC–PAD–MS/MS. (a) UPLC chromatogram of DL-4-hydroxyphenyllactic acid, (a-1) MS for DL-4-hydroxyphenyllactic acid, (b) UPLC chromatogram of 2-isopropylmalic acid, (b-1) MS for 2-isopropylmalic acid, (c) UPLC chromatogram of catechin, (c-1) MS for catechin, (d) UPLC chromatogram of neochlorogenic acid, (d-1) MS for neochlorogenic acid.
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