2, 5-diketopiperazines in food and beverages: Taste and bioactivity
Abstract
2,5-Diketopiperazines (2,5-DKPs) have been found to occur in a wide range of food and beverages, and display an array of chemesthetic effects (bitter, astringent, metallic, and umami) that can contribute to the taste of a variety of foods. These smallest cyclic peptides also occur as natural products and have been found to display a variety of bioactivities from antibacterial, antifungal, to anthroprotective effects and have the potential to be used in the development of new functional foods. An overview of the synthesis of these small chiral molecules and their molecular properties is presented. The occurrence, taste, and bioactivity of all simple naturally occurring 2,5-DKPs to date have been reviewed and those found in food from yeasts, fungi, and bacteria that have been used in food preparation or contamination, as well as metabolites of sweeteners and antibiotics added to food are also reviewed.
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Cyclic dipeptides can be formed in foods by chemical reactions during thermal processing, or by yeast and LAB during fermentation.
“They can be formed in foods by chemical reactions during thermal processing, or by yeast and LAB during fermentation [175].”
From Lactic Acid Bacteria in Raw-Milk Cheeses: From Starter Cultures to Probiotic Functions (2022) · cites this paper as [175]
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Lactic Acid Bacteria in Raw-Milk Cheeses: From Starter Cultures to Probiotic Functions
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“They can be formed in foods by chemical reactions during thermal processing, or by yeast and LAB during fermentation [175].”
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- Authors
- Borthwick, A. D., & Da Costa, N. C.
- Corresponding author
- Borthwick, Alan D.
- ORCID
- Borthwick, Alan D.
- Venue
- Critical Reviews in Food Science and Nutrition
- Publisher
- Informa UK Limited
- Published
- 2015-01-28
- Volume
- 57
- Issue
- 4
- Pages
- 718-742
- ISSN
- 1040-8398 (ISSN-L)
- 1549-7852
- OpenAlex
- W2040998192
- Cited by
- 92
- References
- 159
- Citations by year
- 2026: 8 · 2025: 9 · 2024: 12 · 2023: 7 · 2022: 15 · 2021: 9 · 2020: 7 · 2019: 10 · 2018: 7 · 2017: 6 · 2016: 1 · 2013: 1
- FWCI
- 4.49
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Critical Reviews in Food Science and Nutrition (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Nursing › Nutrition and Dietetics › Biochemical Analysis and Sensing Techniques
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Polyamine Metabolism and Applications
- Keywords
- 2,5-diketopiperazines, cyclic peptides, food flavor, taste perception, biological activity, antibacterial activity, antifungal activity, functional foods, asymmetric synthesis, natural products, yeast, fungi, bacteria, antibiotic metabolites, food contamination
- MeSH terms
- Animals, Beverages, Biological Products, Fermentation, Food Analysis, Humans, Piperazines
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