Structure–activity relationship of antioxidant dipeptides: Dominant role of Tyr, Trp, Cys and Met residues

Zheng, Lin; Zhao, Yue; Dong, Hongzhu; Su, Guowan; Zhao, Ming

doi:10.1016/j.jff.2015.12.003

Cited by 165 publications

(128 citation statements)

References 46 publications

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“…For in vitro chemical assays, it is worth of mentioning that in ABTS and ORAC assays, peptides with Tyr, Trp, Ala, Asp, and Cys in N‐terminal side or C‐terminal side show high radical scavenging ability (Zheng, Zhao, Dong, et al, ). YGD exhibited relative high abilities both in ABTS and ORAC assays mainly in virtue of the existence of Tyr in N‐terminal and Asp in C‐terminal.…”

Section: Resultsmentioning

confidence: 99%

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Analysis of antioxidant effect of two tripeptides isolated from fermented grains (Jiupei) and the antioxidative interaction with 4‐methylguaiacol, 4‐ethylguaiacol, and vanillin

Jiang

Zhao

Luo

et al. 2019

Food Science & Nutrition

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Jiupei (fermented grains) is the raw material for Baijiu distillation. The antioxidant activities of peptides Val‐Asn‐Pro (VNP) and Tyr‐Gly‐Asp (YGD) identified from Jiupei were evaluated according to in vitro chemical assays (e.g., 2,2′‐azino‐bis (3‐ethylbenzothiazoline‐6‐sulfonic acid) diammonium salt, 1,1‐diphenyl‐2‐picrylhydrazyl, and oxygen radical absorbance capacity) and 2,2′‐azobis (2‐methylpropionamide)‐dihydrochloride‐activated HepG2 cell model. The interaction on antioxidant activities between peptides (VNP and YGD) and three functional phenols (4‐methylguaiacol, 4‐ethylguaiacol, and vanillin) which were found in Baijiu was also measured. On the basis of the results, two peptides exhibited strong antioxidant ability in oxygen radical absorbance capacity (ORAC) assay. Furthermore, they suppressed the generation of reactive oxygen species. The intracellular antioxidant enzymatic system and nonenzymatic system were also regulated by VNP and YGD. In addition, it was confirmed that partial auxo‐action between peptides and phenols appeared mostly in chemical assays. The findings above might indicate that VNP and YGD are potent natural antioxidants in Jiupei even in Baijiu through distillation process and lay the foundation for illustrating the interactions among different functional substances in Baijiu.

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Section: Resultsmentioning

confidence: 99%

“…Reducing power assay was based on a previous Zheng's method (Zheng, Zhao, Dong, et al, 2016) with appropriate modifications.…”

Section: Rp Assaymentioning

confidence: 99%

Analysis of antioxidant effect of two tripeptides isolated from fermented grains (Jiupei) and the antioxidative interaction with 4‐methylguaiacol, 4‐ethylguaiacol, and vanillin

Jiang

Zhao

Luo

et al. 2019

Food Science & Nutrition

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“…While many QSAR studies have yielded models with statistically signicant correlations, other studies have not achieved this result, possibly due to the relatively low number of peptides in the training set, structural diversity and/or structural relevance of the peptides therein. 31,51,66 This again highlights the importance of the quality/heterogeneity of the data which may be included in the QSAR model. 18 In addition, when the mechanism of action is not fully understood, e.g., mode of enzyme inhibition, it can be challenging to select meaningful peptide descriptors to build QSAR models.…”

Section: Limitations Of Qsar For the Study Of Bapsmentioning

confidence: 98%

“…QSAR study of the radical scavenging (2,2 0 -azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) and 2,2 0 -azobis(2-aminopropane)dihydrochloride (AAPH)) ability of dipeptides containing Trp and Tyr at the N-terminus was carried out. 66 Differences in the preferred C-terminal amino acid residue of dipeptides with ABTS scavenging properties were seen when a Tyr or Trp was found at the N-terminus of the dipeptide (Table 3). For larger peptides (tri-and tetrapeptides), it was shown that the N-terminal (high hydrophobicity and low electronic properties) and next to the C-terminal (hydrophilic) amino acids were the most important in the antioxidant (ferric thiocyanate method, autoxidation system of linoleic acid) activity.…”

Section: Antioxidant Peptidesmentioning

confidence: 99%

“…These assays are targeted at quite different oxidative species, therefore, leading to different outcomes in terms of the peptides' potential ability to reduce oxidation. 66 These differences highlight the challenges in attempting to nd a consensus in the structural properties for antioxidant peptides. As highlighted in the recent review of Li and Yu, 22 no clear consensus between peptide structure and antioxidant peptides has been established using QSAR studies, possibly due to the lack of knowledge of the mechanism of action of such peptides.…”

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confidence: 99%

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Learnings from quantitative structure–activity relationship (QSAR) studies with respect to food protein-derived bioactive peptides: a review

Nongonierma

Fitzgerald

2016

RSC Adv.

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Stability and antioxidant activities of corn protein hydrolysates under simulated gastrointestinal digestion

et al. 2018

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Background and objectives: Bioactive peptides are expected to be ingested orally; it is important to study the effect of simulated gastrointestinal (GI) digestion on the stability and antioxidant activity of these peptides. Findings: After simulated GI digestion, degree of hydrolysis of corn protein hydrolysates (CPH) significantly increased from 22.7% to 39.4% while 77.5% peptides were still retained. Compared to the undigested CPH, the final CPH digests exhibited excellent antioxidant activity, including 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl radical scavenging activity (12.9% increase), hydroxyl radical scavenging activity (4.1% increase), and reducing power (50.9% increase), but lower inhibition rate of linoleic acid peroxidation (41.5% decrease). The free amino acids including Pro, Asp, and Glu maintained at a low proportion during the entire course of digestion. Two GIresistant antioxidant peptides (Tyr-Pro-Gln, 406.45 Da; Ala-Tyr-Leu, 365.43 Da) were purified with multistep chromatography and identified by UPLC-ESI-MS. Conclusions: The CPH digests exhibited excellent antioxidant activity after simulated GI digestion. The results suggested that CPH obtained by alcalase digestion are potential functional foods or nutraceuticals due to their content of bioactive peptides. Significance and novelty: Some peptides containing Pro, Asp, and Glu had a strong ability to resist digestion. Two novel antioxidant peptides have been purified and identified from the CPH digests.

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Structure–activity relationship of antioxidant dipeptides: Dominant role of Tyr, Trp, Cys and Met residues

Cited by 165 publications

References 46 publications

Analysis of antioxidant effect of two tripeptides isolated from fermented grains (Jiupei) and the antioxidative interaction with 4‐methylguaiacol, 4‐ethylguaiacol, and vanillin

Analysis of antioxidant effect of two tripeptides isolated from fermented grains (Jiupei) and the antioxidative interaction with 4‐methylguaiacol, 4‐ethylguaiacol, and vanillin

Learnings from quantitative structure–activity relationship (QSAR) studies with respect to food protein-derived bioactive peptides: a review

Stability and antioxidant activities of corn protein hydrolysates under simulated gastrointestinal digestion

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