2,5-diketopiperazines in food and beverages: Taste and bioactivity

Borthwick, Alan D.; Costa, Neil C. Da

doi:10.1080/10408398.2014.911142

Cited by 68 publications

(68 citation statements)

References 137 publications

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“…The second‐ranked metabolite was identified as proline betaine ( m / z 144.1018), a biomarker of citrus intake that was found associated with increased odds of CD (OR = 1.56). Three other food‐derived metabolites of the signature were inversely associated with CD: i) a metabolite tentatively identified as CMPFP ( m / z 251.1278, fourth‐ranked: OR = 0.74), a structural derivative of a reported fish biomarker, 3‐carboxy‐4‐methyl‐5‐propyl‐2‐furanopropionic acid (CMPF), ii) an unknown metabolite ( m / z 271.2056, seventh‐ranked; OR = 0.69) possibly linked to red wine intake (see below correlations with dietary intake), and iii) cyclo(prolyl‐valyl) ( m / z 197.1284; eight‐ranked; OR = 0.90), a diketopiperazine reported in chocolate, and other fermented and heated foods …”

Section: Resultsmentioning

confidence: 99%

Diet‐Related Metabolites Associated with Cognitive Decline Revealed by Untargeted Metabolomics in a Prospective Cohort

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Lefèvre‐Arbogast

González‐Domínguez

et al. 2019

Molecular Nutrition Food Res

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Scope Untargeted metabolomics may reveal preventive targets in cognitive aging, including within the food metabolome. Methods and results A case‐control study nested in the prospective Three‐City study includes participants aged ≥65 years and initially free of dementia. A total of 209 cases of cognitive decline and 209 controls (matched for age, gender, education) with slower cognitive decline over up to 12 years are contrasted. Using untargeted metabolomics and bootstrap‐enhanced penalized regression, a baseline serum signature of 22 metabolites associated with subsequent cognitive decline is identified. The signature includes three coffee metabolites, a biomarker of citrus intake, a cocoa metabolite, two metabolites putatively derived from fish and wine, three medium‐chain acylcarnitines, glycodeoxycholic acid, lysoPC(18:3), trimethyllysine, glucose, cortisol, creatinine, and arginine. Adding the 22 metabolites to a reference predictive model for cognitive decline (conditioned on age, gender, education and including ApoE‐ε4, diabetes, BMI, and number of medications) substantially increases the predictive performance: cross‐validated Area Under the Receiver Operating Curve = 75% [95% CI 70–80%] compared to 62% [95% CI 56–67%]. Conclusions The untargeted metabolomics study supports a protective role of specific foods (e.g., coffee, cocoa, fish) and various alterations in the endogenous metabolism responsive to diet in cognitive aging.

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Section: Resultsmentioning

confidence: 99%

Diet‐Related Metabolites Associated with Cognitive Decline Revealed by Untargeted Metabolomics in a Prospective Cohort

Low

Lefèvre‐Arbogast

González‐Domínguez

et al. 2019

Molecular Nutrition Food Res

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“…cGP is an endogenous neuropeptide, identified for the first time in the brain tissue of adult rats. cGP has been also isolated from various sources such as plasma, breast milk, blackcurrant, food and beverages, native collagen as well as marine sponges.…”

Section: Igf‐1‐derived Cgp and Its Generationmentioning

confidence: 99%

Proline‐containing peptides—New insight and implications: A Review

Misiura

Miltyk

2019

BioFactors

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The family of regulatory proline‐containing peptides (PCPs), also known as glyprolines, exhibit significant biological activity. The group of glyprolines includes Gly‐Pro (GP), Pro‐Gly‐Pro (PGP), cyclic Gly‐Pro (cGP), as well as PGP derivatives, for example, N‐acetylated PGP (N‐a‐PGP) and N‐methylated PGP (N‐m‐PGP). PCPs are engaged in various biological processes including the proinflammatory neutrophil chemoattraction in lung diseases, inflammatory bowel diseases or ischemic stroke. Glyprolines have been also postulated to play an important role as atheroprotective and anticoagulant agents, exhibit neuroprotective effects in Parkinson's disease, as well as regulate insulin‐like growth factor (IGF) homeostasis. It was also noticed that PCPs inhibit proliferation and migration of keratinocytes in wound healing, protection of the gastric mucosa and stimulation of its regeneration. The regulatory glyprolines are derived from endogenous and exogenous sources. Most PCPs are derived from collagen or diet protein degradation. Recently, great interest is concentrated on short proline‐rich oligopeptides derived from IGF‐1 degradation. The mechanism of PCPs biological activity is not fully explained. It involves receptor‐mediated mechanisms, for example, N‐a‐PGP acts as CXCR1/2 receptor ligand, whereas cGP regulates IGF‐1 bioavailability by modifying the IGF‐1 binding to the IGF‐1 binding protein‐3. PGP has been observed to interact with collagen‐specific receptors. The data suggest a promising role of PGP as a target of various diseases therapy. This review is focused on the effect of PCPs on metabolic processes in different tissues and the molecular mechanism of their action as an approach to pharmacotherapy of PCPs‐dependent diseases.

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“…Cyclization of amino dipeptide esters can also be carried out under thermal conditions, normally by refluxing them in high boiling solvents such as toluene or xylene for 24 h (Borthwick, 2012). In addition, CDPs are often products of unwanted side reactions or degradation products of oligo-and polypeptides in processed food and beverages (Borthwick and Da Costa, 2017;Prasad, 1995). They are frequently formed during the chemical degradation of products in roasted coffee, stewed beef, and beer (Chen et al, 2009;Gautschi et al, 1997;Ginz and Engelhardt, 2000).…”

Section: Cyclic Dipeptidesmentioning

confidence: 99%