Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates
The <span style="font-variant: small-caps;">Maillard</span> reaction is well known for producing antioxidant compounds alongside colored substances. Low-molecular-weight antioxidant intermediates such as maltol (MAL) or norfuraneol (NF) are well described, but it is still uncle...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-09-01
|
| Series: | Antioxidants |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3921/12/9/1788 |
| _version_ | 1797581522555895808 |
|---|---|
| author | Leon Valentin Bork Maximilian Baumann Tobias Stobernack Sascha Rohn Clemens Kanzler |
| author_facet | Leon Valentin Bork Maximilian Baumann Tobias Stobernack Sascha Rohn Clemens Kanzler |
| author_sort | Leon Valentin Bork |
| collection | DOAJ |
| description | The <span style="font-variant: small-caps;">Maillard</span> reaction is well known for producing antioxidant compounds alongside colored substances. Low-molecular-weight antioxidant intermediates such as maltol (MAL) or norfuraneol (NF) are well described, but it is still unclear which of these <span style="font-variant: small-caps;">Maillard</span> intermediates are the precursors of antioxidant and colored melanoidins—the so-called late stage <span style="font-variant: small-caps;">Maillard</span> reaction products. This study aimed to provide novel insights into the correlation between browning potential and antioxidant properties of reaction products formed during the heat treatment of prominent <span style="font-variant: small-caps;">Maillard</span> reaction intermediates. It was achieved by the incubation of binary reaction systems composed of methylglyoxal (MGO) or NF in combination with furfural (FF), MAL, and pyrrole-2-carbaldehyde (PA) at pH 5 and 130 °C for up to 120 min. Overall, it could be shown that the formation of colored products in the binary NF reaction systems was more efficient compared to those of MGO. This was reflected in an increased browning intensity of up to 400% and a lower conversion rate of NF compared to MGO. The colorants formed by NF and FF or PA (~0.34 kDa and 10–100 kDa) were also found to exhibit higher molecular weights compared to the analogue products formed in the MGO incubations (<0.34 kDa and 10–100 kDa). The incorporation of NF into these heterogenous products with FF and PA resulted in the preservation of the initial antioxidant properties of NF (<i>p</i> < 0.05), whereas no antioxidant products were formed after the incubation of MGO. |
| first_indexed | 2024-03-10T23:05:44Z |
| format | Article |
| id | doaj.art-b16cda7680b84bc89d6d06a8ed8b0024 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-10T23:05:44Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-b16cda7680b84bc89d6d06a8ed8b00242023-11-19T09:20:27ZengMDPI AGAntioxidants2076-39212023-09-01129178810.3390/antiox12091788Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction IntermediatesLeon Valentin Bork0Maximilian Baumann1Tobias Stobernack2Sascha Rohn3Clemens Kanzler4Department of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, GermanyDepartment of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, GermanyDepartment of Chemical and Product Safety, German Federal Institute for Risk Assessment, Max-Dohrn-Str. 8–10, 10589 Berlin, GermanyDepartment of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, GermanyDepartment of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, GermanyThe <span style="font-variant: small-caps;">Maillard</span> reaction is well known for producing antioxidant compounds alongside colored substances. Low-molecular-weight antioxidant intermediates such as maltol (MAL) or norfuraneol (NF) are well described, but it is still unclear which of these <span style="font-variant: small-caps;">Maillard</span> intermediates are the precursors of antioxidant and colored melanoidins—the so-called late stage <span style="font-variant: small-caps;">Maillard</span> reaction products. This study aimed to provide novel insights into the correlation between browning potential and antioxidant properties of reaction products formed during the heat treatment of prominent <span style="font-variant: small-caps;">Maillard</span> reaction intermediates. It was achieved by the incubation of binary reaction systems composed of methylglyoxal (MGO) or NF in combination with furfural (FF), MAL, and pyrrole-2-carbaldehyde (PA) at pH 5 and 130 °C for up to 120 min. Overall, it could be shown that the formation of colored products in the binary NF reaction systems was more efficient compared to those of MGO. This was reflected in an increased browning intensity of up to 400% and a lower conversion rate of NF compared to MGO. The colorants formed by NF and FF or PA (~0.34 kDa and 10–100 kDa) were also found to exhibit higher molecular weights compared to the analogue products formed in the MGO incubations (<0.34 kDa and 10–100 kDa). The incorporation of NF into these heterogenous products with FF and PA resulted in the preservation of the initial antioxidant properties of NF (<i>p</i> < 0.05), whereas no antioxidant products were formed after the incubation of MGO.https://www.mdpi.com/2076-3921/12/9/1788<span style="font-variant: small-caps">Maillard</span> reactionnon-enzymatic browningmethylglyoxalnorfuraneolfurfuralα-dicarbonyl compounds |
| spellingShingle | Leon Valentin Bork Maximilian Baumann Tobias Stobernack Sascha Rohn Clemens Kanzler Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates Antioxidants <span style="font-variant: small-caps">Maillard</span> reaction non-enzymatic browning methylglyoxal norfuraneol furfural α-dicarbonyl compounds |
| title | Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates |
| title_full | Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates |
| title_fullStr | Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates |
| title_full_unstemmed | Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates |
| title_short | Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic <span style="font-variant: small-caps">Maillard</span> Reaction Intermediates |
| title_sort | colorants and antioxidants deriving from methylglyoxal and heterocyclic span style font variant small caps maillard span reaction intermediates |
| topic | <span style="font-variant: small-caps">Maillard</span> reaction non-enzymatic browning methylglyoxal norfuraneol furfural α-dicarbonyl compounds |
| url | https://www.mdpi.com/2076-3921/12/9/1788 |
| work_keys_str_mv | AT leonvalentinbork colorantsandantioxidantsderivingfrommethylglyoxalandheterocyclicspanstylefontvariantsmallcapsmaillardspanreactionintermediates AT maximilianbaumann colorantsandantioxidantsderivingfrommethylglyoxalandheterocyclicspanstylefontvariantsmallcapsmaillardspanreactionintermediates AT tobiasstobernack colorantsandantioxidantsderivingfrommethylglyoxalandheterocyclicspanstylefontvariantsmallcapsmaillardspanreactionintermediates AT sascharohn colorantsandantioxidantsderivingfrommethylglyoxalandheterocyclicspanstylefontvariantsmallcapsmaillardspanreactionintermediates AT clemenskanzler colorantsandantioxidantsderivingfrommethylglyoxalandheterocyclicspanstylefontvariantsmallcapsmaillardspanreactionintermediates |