ArticleAntioxidants (Basel, Switzerland)2022
Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins.
Article in Antioxidants (Basel, Switzerland), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 17 citations in OpenAlex.
- Amino Acid Betaxanthins: Absorption, Fluorescence, And Stability.Journal of natural products · 2025Article
- Betalain Pigments: Isolation and Application as Reagents for Colorimetric Methods and Biosensors.Biosensors · 2025Review
- In Silico Mass Spectrometric Fragmentation and Liquid Chromatography with Tandem Mass Spectrometry (LC-MS/MS) Betalainic Fingerprinting: Identification of Betalains in Red Pitaya.Molecules (Basel, Switzerland) · 2024Article
- Semisynthesis of Betaxanthins from Purified Betacyanin ofMolecules (Basel, Switzerland) · 2024Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Betaxanthins are natural products with high antioxidant and anti-inflammatory properties. Here, we describe the semisynthesis of twenty-one betaxanthins derived from proteinogenic amino acids, including the elusive betaxanthin of l-cysteine and two betaxanthins derived from l-lysine, and rationalize their antioxidant properties in mechanistic terms. The antioxidant capacity and redox potential of these betaxanthins were compared to those of model betaxanthins derived from dopamine, l-DOPA (L-3,4-dihydroxyphenylalanine), and pyrrolidine and structure-property relationships were established by using matched molecular pair analysis and a model developed using a genetic algorithm. Either a phenol or indole moiety enhance the antioxidant capacity of betaxanthins, which is overall much higher than that of their amino acid precursors and standard antioxidants, except for the cysteine-betaxanthin. The one-electron oxidation of amino acid betaxanthins produces radicals stabilized in multiple centers, as demonstrated by quantum chemical calculations.
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Registered trials
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