Novel approach for purification of major betalains using flash chromatography and comparison of radical scavenging and antioxidant activities

Fernando, Ganwarige Sumali N.; Sergeeva, Natalia N.; Frutos, María José; Marshall, L.; Boesch, Christine

doi:10.1016/j.foodchem.2022.132632

Cited by 23 publications

(20 citation statements)

References 37 publications

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“…Our findings regarding BET were consistent with Esatbeyoglu et al [ 56 ] who demonstrated dose-dependent radial quenching properties of BET in a similar concentration range (1–10 μM). In contrast to BET, VUL and IND did not exhibit any evident antiradical activity in both DPPH and superoxide assays, highlighting the different potencies of betaxanthins and betacyanins, which was in line with our previous findings [ 29 ].…”

Section: Resultssupporting

confidence: 91%

“…The BET, VUL and IND pigments used were previously isolated from red and yellow beetroot ( Beta vulgaris L.) and yellow prickly pear ( Opuntia ficus-indica L.), respectively, using the flash column chromatography method as described in Fernando et al [ 29 ]. The purities of previously isolated BET, VUL and IND have reached 97%, 79% and 95%, respectively, as determined by high-performance liquid chromatography with mass spectrometry (LC-MS).…”

Section: Methodsmentioning

confidence: 99%

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Uptake and Immunomodulatory Properties of Betanin, Vulgaxanthin I and Indicaxanthin towards Caco-2 Intestinal Cells

et al. 2022

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The present study aimed to compare the absorption and transport patterns of three main betalains, betanin, vulgaxanthin I and indicaxanthin, into intestinal epithelial cells and to assess their distinct molecular effects on inflammatory and redox-related cell signalling in association with their radial scavenging potencies. All three betalains showed anti-inflammatory effects (5–80 μM), reflected by attenuated transcription of pro-inflammatory mediators such as cyclooxygenase-2 and inducible NO-synthase. Concomitant increases in antioxidant enzymes such as heme oxygenase-1 were only observed for betanin. Moreover, betanin uniquely demonstrated a potent dose-dependent radical scavenging activity in EPR and cell-based assays. Results also indicated overall low permeability for the three betalains with Papp of 4.2–8.9 × 10−7 cm s−1. Higher absorption intensities of vulgaxanthin and indicaxanthin may be attributed to smaller molecular sizes and greater lipophilicity. In conclusion, betanin, vulgaxanthin I and indicaxanthin have differentially contributed to lowering inflammatory markers and mitigating oxidative stress, implying the potential to ameliorate inflammatory intestinal disease. Compared with two betaxanthins, the greater efficacy of betanin in scavenging radical and promoting antioxidant response might, to some extent, compensate for its poorer absorption efficiency, as demonstrated by the Caco-2 cell model.

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Section: Resultssupporting

confidence: 91%

Section: Methodsmentioning

confidence: 99%

Uptake and Immunomodulatory Properties of Betanin, Vulgaxanthin I and Indicaxanthin towards Caco-2 Intestinal Cells

et al. 2022

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“…The fact that all experiments have been performed using compounds prepared, purified, and studied in the same way increase the confidence for comparing the results obtained. Our results on Pro-Bx (indicaxanthin) agree with reports showing that, despite being a well-known antioxidant and anti-inflammatory agent in vivo [ 73 , 74 , 75 ], Pro-Bx does not have an exceptional antioxidant capacity [ 55 , 72 ], and is lower than that of vulgaxanthin I (Gln-Bx) [ 72 ], which is abundant in Golden beetroots [ 76 ]. These results have been rationalized by considering that the presence of a positively charged iminium group in indicaxanthin decreases its antioxidant capacity [ 53 , 72 ], but this interpretation implies that other more negatively charged betaxanthins may have even better antioxidant properties and/or that the iminium portion of Pro-Bx is important for its biological properties.…”

Section: Discussionsupporting

confidence: 90%

“…Although amino acid betaxanthins have been found in vegetables and fungi [ 16 , 17 , 20 , 34 , 53 , 71 ] and the antioxidant capacity of some of them have been described previously [ 32 , 37 , 53 , 72 ], the complete study of betaxanthins derived from all proteinogenic amino acids, except selenocysteine, is reported for the first time. The fact that all experiments have been performed using compounds prepared, purified, and studied in the same way increase the confidence for comparing the results obtained.…”

Section: Discussionmentioning

confidence: 99%

Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins

et al. 2022

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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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“…Betanin (BET, CAS 7659‐95‐2), neobetanin (NEO, CAS 71199‐29‐6), vulgaxanthin I (VGX, CAS 904‐62‐1), and indicaxanthin (IDX, CAS 2181‐75‐1), were previously isolated from red beetroot and yellow prickly pear [ 21 ] with purities of 97%, 52%, 79%, and 95% respectively (as per HPLC). All compounds were dissolved in 30% v/v ethanol to prepare 10 mM stock solutions and stored at −20 °C for further experiments.…”

Section: Methodsmentioning

confidence: 99%

Differential Effects of Betacyanin and Betaxanthin Pigments on Oxidative Stress and Inflammatory Response in Murine Macrophages

Fernando

Sergeeva

Vagkidis

et al. 2023

Molecular Nutrition Food Res

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Scope: Betalain pigments are increasingly highlighted for their bioactive and anti‐inflammatory properties, although research is lacking to demonstrate contributions of individual betalains. The work herein aimed to compare effects of four main betalains on inflammatory and cell‐protective markers and to highlight potential structure‐related relationships of the two main subgroups: betacyanins vs betaxanthins. Methods and results: Murine RAW 264.7 macrophages were stimulated with bacterial lipopolysaccharide following incubation with betacyanins (betanin, neobetanin) and betaxanthins (indicaxanthin, vulgaxanthin I) in concentrations from 1 to 100 µM. All betalains suppressed expression of pro‐inflammatory markers IL‐6, IL‐1β, iNOS, and COX‐2 with tendency for stronger effects of betacyanins compared to betaxanthins. In contrast, HO‐1 and gGCS showed mixed and only moderate induction, while more emphasized effects were observed for betacyanins. While all betalains suppressed mRNA levels of NADPH oxidase 2 (NOX‐2), a superoxide generating enzyme, only betacyanins were able to counteract hydrogen peroxide induced reactive oxygen species (ROS) generation, in alignment with their radical scavenging potential. Furthermore, betaxanthins exerted pro‐oxidant properties, elevating ROS production beyond hydrogen peroxide stimulation. Conclusion: In summary, all betalains display anti‐inflammatory properties, although only betacyanins demonstrate radical scavenging capacities, indicating potential differing responses under oxidative stress conditions, which requires further research.

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Novel approach for purification of major betalains using flash chromatography and comparison of radical scavenging and antioxidant activities

Cited by 23 publications

References 37 publications

Uptake and Immunomodulatory Properties of Betanin, Vulgaxanthin I and Indicaxanthin towards Caco-2 Intestinal Cells

Uptake and Immunomodulatory Properties of Betanin, Vulgaxanthin I and Indicaxanthin towards Caco-2 Intestinal Cells

Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins

Differential Effects of Betacyanin and Betaxanthin Pigments on Oxidative Stress and Inflammatory Response in Murine Macrophages

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