Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural
The Maillard reaction (MR) can affect the color, flavor, organoleptic properties, and nutritional value of food. Sometimes, MR is undesirable due to lowering the nutrient utilization, producing harmful neo-formed compounds, etc. In this case, it is necessary to control MR. Some chemical substances,...
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| Format: | Article |
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MDPI AG
2021-06-01
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| Series: | Foods |
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| Online Access: | https://www.mdpi.com/2304-8158/10/6/1391 |
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| author | Shiqiang Yang Zhongfei Zhang Jiaoyong Li Yuge Niu Liangli Lucy Yu |
| author_facet | Shiqiang Yang Zhongfei Zhang Jiaoyong Li Yuge Niu Liangli Lucy Yu |
| author_sort | Shiqiang Yang |
| collection | DOAJ |
| description | The Maillard reaction (MR) can affect the color, flavor, organoleptic properties, and nutritional value of food. Sometimes, MR is undesirable due to lowering the nutrient utilization, producing harmful neo-formed compounds, etc. In this case, it is necessary to control MR. Some chemical substances, such as phenolic acid, vitamins, aminoguanidine, and thiols extracted from garlic or onion, can effectively prevent MR. In this study, L-cysteine (<span style="font-variant: small-caps;">L</span>-cys) was found to inhibit MR after screening 10 sulfhydryl compounds by comparing their ability to mitigate browning. The inhibition mechanism was speculated to be related to the removal of 5-hydroxymethylfurfural (HMF), a key mid-product of MR. The reaction product of HMF and <span style="font-variant: small-caps;">L</span>-cys was identified and named as 1-dicysteinethioacetal–5-hydroxymethylfurfural (DCH) according to the mass spectrum and nuclear magnetic resonance spectrum of the main product. Furthermore, DCH was detected in the glutamic–fructose mixture after <span style="font-variant: small-caps;">L</span>-cys was added. In addition, the production of DCH also increased with the addition of <span style="font-variant: small-caps;">L</span>-cys. It also was worth noting that DCH showed no cell toxicity to RAW 264.7 cells. Moreover, the in vitro assays indicated that DCH had anti-inflammatory and antioxidant activities. In conclusion, <span style="font-variant: small-caps;">L</span>-cys inhibits MR by converting HMF into another adduct DCH with higher safety and health benefits. <span style="font-variant: small-caps;">L</span>-cys has the potential to be applied as an inhibitor to prevent MR during food processing and storage. |
| first_indexed | 2024-03-10T10:22:57Z |
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| issn | 2304-8158 |
| language | English |
| last_indexed | 2024-03-10T10:22:57Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Foods |
| spelling | doaj.art-f349328b8d2644aaad627df9f82a9aa22023-11-22T00:19:29ZengMDPI AGFoods2304-81582021-06-01106139110.3390/foods10061391Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-HydroxymethylfurfuralShiqiang Yang0Zhongfei Zhang1Jiaoyong Li2Yuge Niu3Liangli Lucy Yu4Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai 200240, ChinaShenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, ChinaInstitute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai 200240, ChinaInstitute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai 200240, ChinaDepartment of Nutrition and Food Science, University of Maryland, College Park, MD 20742, USAThe Maillard reaction (MR) can affect the color, flavor, organoleptic properties, and nutritional value of food. Sometimes, MR is undesirable due to lowering the nutrient utilization, producing harmful neo-formed compounds, etc. In this case, it is necessary to control MR. Some chemical substances, such as phenolic acid, vitamins, aminoguanidine, and thiols extracted from garlic or onion, can effectively prevent MR. In this study, L-cysteine (<span style="font-variant: small-caps;">L</span>-cys) was found to inhibit MR after screening 10 sulfhydryl compounds by comparing their ability to mitigate browning. The inhibition mechanism was speculated to be related to the removal of 5-hydroxymethylfurfural (HMF), a key mid-product of MR. The reaction product of HMF and <span style="font-variant: small-caps;">L</span>-cys was identified and named as 1-dicysteinethioacetal–5-hydroxymethylfurfural (DCH) according to the mass spectrum and nuclear magnetic resonance spectrum of the main product. Furthermore, DCH was detected in the glutamic–fructose mixture after <span style="font-variant: small-caps;">L</span>-cys was added. In addition, the production of DCH also increased with the addition of <span style="font-variant: small-caps;">L</span>-cys. It also was worth noting that DCH showed no cell toxicity to RAW 264.7 cells. Moreover, the in vitro assays indicated that DCH had anti-inflammatory and antioxidant activities. In conclusion, <span style="font-variant: small-caps;">L</span>-cys inhibits MR by converting HMF into another adduct DCH with higher safety and health benefits. <span style="font-variant: small-caps;">L</span>-cys has the potential to be applied as an inhibitor to prevent MR during food processing and storage.https://www.mdpi.com/2304-8158/10/6/1391<span style="font-variant: small-caps">L</span>-cysteineMaillard reactioninhibitionHMFsulfhydryl compound |
| spellingShingle | Shiqiang Yang Zhongfei Zhang Jiaoyong Li Yuge Niu Liangli Lucy Yu Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural Foods <span style="font-variant: small-caps">L</span>-cysteine Maillard reaction inhibition HMF sulfhydryl compound |
| title | Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural |
| title_full | Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural |
| title_fullStr | Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural |
| title_full_unstemmed | Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural |
| title_short | Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural |
| title_sort | inhibition mechanism of l cysteine on maillard reaction by trapping 5 hydroxymethylfurfural |
| topic | <span style="font-variant: small-caps">L</span>-cysteine Maillard reaction inhibition HMF sulfhydryl compound |
| url | https://www.mdpi.com/2304-8158/10/6/1391 |
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