The DOI matches its Crossref record; 19 of the 19 references it cites were found in a registry or an index.
The influence of acylation, metal binding and natural antioxidants on the thermal stability of red cabbage anthocyanins in neutral solution
Abstract
The main red cabbage anthocyanins (pigments) are cyanidin glycosides bearing one or two acyl groups derived from hydroxycinnamic acids (HCAs). Through π-stacking interactions with the cyanidin chromophore, the HCA residues have a deep influence on the color expressed and its stability. In this work, a series of non-, mono- and diacylated anthocyanins were investigated in neutral solution (pH 7 and 8), where the pigments exhibit purple to blue colors. Under such conditions, the gradual color loss observed is a combination of two distinct processes involving the cyanidin nucleus: reversible water addition and irreversible autoxidation. By acidification to pH < 2, the colorless forms stemming from water addition (hemiketal and chalcones) are converted to the red flavylium ion, thereby permitting the selective monitoring of the irreversible contribution. The kinetics of color loss and of true pigment degradation could thus be recorded for each pigment. The influence of iron - cyanidin binding and of antioxidants (caffeic acid, N-acetylcysteine) was also investigated. A complete kinetic analysis combining the anthocyanin colored and colorless forms and the degradation products is provided. Overall, it appears that acylation is critical to color stability. For instance, the nonacylated pigment is rapidly bleached as a result of fast water addition and its iron complex is too unstable to provide protection. By contrast, the diacylated pigments are efficiently protected against hydra…
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“The concept of natural yellow colorants has emerged as a powerful alternative to synthetic options, offering vibrant colors [30, 31].”
From EXPLOITING ECO-FRIENDLY NATURAL DYES FROM PLANT SOURCES: EXTRACTION AND DIVERSE APPLICATIONS (2024) · cites this paper as [31]
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Stabilizing and Modulating Color by Copigmentation: Insights from Theory and Experiment
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Self-citationBlue flower color development by anthocyanins: from chemical structure to cell physiology
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Color and Antioxidant Properties of Cyanidin-Based Anthocyanin Pigments
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Chemistry and applications of flavylium compounds: a handful of colours
Piña, F., Melo, M. J., Laia, C. A. T., Parola, A. J., & Lima, J. C. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15126f · Cited by 435
Thermal degradation of anthocyanins and its impact on color and in vitro antioxidant capacity
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Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color
Cruz, L., Basílio, N., Mateus, N. F. D. C. B., de Freitas, V. A. P., & Piña, F. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00399 · Cited by 267
Xue, H., Zhao, J., Wang, Y., Shi, Z., Xie, K., Liao, X., & Tan, J. (2024) · Food Chemistry X · doi:10.1016/j.fochx.2024.101883 · Cited by 239
Sources and relative stabilities of acylated and nonacylated anthocyanins in beverage systems
Gamage, G. C. V., Lim, Y. Y., & Choo, W. S. (2021) · Journal of Food Science and Technology · doi:10.1007/s13197-021-05054-z · Cited by 140
Chen, Y., Belwal, T., Xu, Y., Ma, Q., Li, D., Li, L., Xiao, H., & Luo, Z. (2022) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2022.2063250 · Cited by 134
Metadata
- Authors
- Fenger, J.-A., Moloney, M., Robbins, R. J., Collins, T. M., & Dangles, O.
- Affiliations
- Université d'Avignon et des Pays de Vaucluse (FR)
- Avignon University
- Mars Wrigley Confectionery (US)
- Corresponding author
- Dangles, Olivier
- Venue
- Food & Function
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2019
- Volume
- 10
- Issue
- 10
- Pages
- 6740-6751
- ISSN
- 2042-6496 (ISSN-L)
- 2042-650X
- OpenAlex
- W2976055990
- Cited by
- 82
- References
- 19
- Citations by year
- 2026: 6 · 2025: 12 · 2024: 19 · 2023: 13 · 2022: 16 · 2021: 10 · 2020: 6
- FWCI
- 4.80
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Food & Function (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry (medical) › Phytochemicals and Antioxidant Activities
- Life Sciences › Agricultural and Biological Sciences › Food Science › Botanical Research and Applications
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant Gene Expression Analysis
- Keywords
- cyanidin glycosides, acylation, hydroxycinnamic acids, thermal stability, color stability, autoxidation, water addition, iron binding, antioxidants, N-acetylcysteine, caffeic acid, degradation kinetics, hydrogen peroxide, bisulfite, food colorants
- MeSH terms
- Acylation, Anthocyanins, Antioxidants, Brassica, Chelating Agents, Color, Coumaric Acids, Hydrogen-Ion Concentration, Iron, Kinetics, Metals, Pigments, Biological
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- Fenger, J.-A., Moloney, M., Robbins, R. J., Collins, T. M., & Dangles, O. (2019). The influence of acylation, metal binding and natural antioxidants on the thermal stability of red cabbage anthocyanins in neutral solution. Food & Function. https://doi.org/10.1039/c9fo01884k
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
