Semisynthesis of Betaxanthins from Purified Betacyanin of Opuntia dillenii sp.: Color Stability and Antiradical Capacity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation of the Purified Extract from the Fruit of Opuntia Dilleni and Obtaining Betalamic Acid
2.2. Semisynthesis of ʟ−Amino Acid-Betaxanthins
2.3. Tentative Characterization of Betaxanthins by UV-Vis and HPLC-ESI-MS
2.4. Determination of the Antioxidant Capacity
2.5. Stability Evaluation of Semisynthetic ʟ−Amino Acid-Betaxanthins by Tristimulus Colorimetry
3. Materials and Methods
3.1. Reagents and Solvents
3.2. Plant Material
3.3. Preparation of Crude Extract (CE) and Purified Extract (PE1)
3.4. Separation of Polyphenols with Ambertite XAD-7 from PE1
3.5. Isolation of Betacyanins from PE2
3.6. Quantification of Betacyanins and Betaxanthins
3.7. Obtaining Betalamic Acid
3.8. Semisynthesis of ʟ−Amino Acid-Betaxanthins
3.9. Betaxanthins Purification
3.10. Analysis of Betaxanthins by UHPLC–ESI–MS
3.11. Determination of Antioxidant Capacity Equivalent to Trolox (TEAC)
3.12. Determination of Antioxidant Activity by 2,2-Diphenyl-1-Picrylhydrazyl (DPPH)
3.13. Colorimetric Measurements at Different pH
3.14. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Betaxanthin | λmax | Ratio Experimental/Theoretical | Yield (%) | % Area (HPLC) S,S/S,R |
---|---|---|---|---|
ʟ−ProBX | 484 | 0.275/0.361 | 76.2 | 66.4/33.6 |
ʟ−AlaBx | 475 | 0.149/0.198 | 75.3 | 47.8/45.2 |
ʟ−LeuBX | 475 | 0.267/0.379 | 70.1 | 72.7/27.3 |
ʟ−PheBX | 477 | 0.482/0.697 | 69.2 | 86.3/13.7 |
Betaxanthin | Molecular Formula | Rt (min) (S,S/S,R) | m/z [M + H]+ |
---|---|---|---|
ʟ−ProBX | C14H17N2O6 | 8.6/7.9 | 310.02547 |
ʟ−AlaBx | C12H15N2O6 | 5.4/5.1 | 284.16047 |
ʟ−LeuBX | C15H21N2O6 | 28.8/26.4 | 326.80460 |
ʟ−PheBX | C18H19N2O6 | 32.0/29.5 | 360.12592 |
Betaxanthin | TEAC (mmol Tx/mmol BX) | DPPH (% Inhibition) |
---|---|---|
ʟ−ProBX | 1.17 ± 0.07 a | 9.85 ± 1.48 a |
ʟ−AlaBx | 2.27 ± 0.04 b | 16.22 ± 1.49 b |
ʟ−LeuBX | 1.61 ± 0.03 c | 12.54 ± 1.36 c |
ʟ−PheBX | 1.27 ± 0.03 a | 11.32 ± 1.97 c |
Betalamic acid | 2.15 ± 0.62 b | 8.73 ± 1.39 a |
Betaxanthins | pH | Storage | Visual Color | L* | a* | b* | C*ab | hab | ∆L* | ∆C*ab | ∆hab | ∆E*ab |
---|---|---|---|---|---|---|---|---|---|---|---|---|
ʟ−Ala-Bx | 4 | BS | 93.8 ± 0.22 | −2.1 ± 0.03 | 37.2 ± 0.07 | 37.3 ± 0.10 | 93.2 ± 0.37 | 3.4 | 20.6 | 0.35 | 20.9 | |
AS | 97.2 ± 0.38 | −1.0 ± 0.01 | 16.7 ± 0.04 | 16.7 ± 0.05 | 93.5 ± 0.28 | |||||||
6 | BS | 92.9 ± 0.15 | −1.2 ± 0.03 | 50.9 ± 0.11 | 51.0 ± 0.13 | 91.4 ± 0.18 | 1.5 | 7.9 | 0.50 | 8.1 | ||
AS | 94.3 ± 0.09 | −1.4 ± 0.05 | 43.0 ± 0.08 | 43.1 ± 0.07 | 91.8 ± 0.13 | |||||||
ʟ−Leu-Bx | 4 | BS | 94.2 ± 0.13 | −1.5 ± 0.02 | 35.4 ± 0.07 | 35.5 ± 0.09 | 92.4 ± 0.19 | 2.9 | 25.5 | 5.6 | 25.7 | |
AS | 97.0 ± 0.11 | 0.55 ± 0.00 | 10.0 ± 0.04 | 10.0 ± 0.08 | 86.9 ± 0.16 | |||||||
6 | BS | 93.1 ± 0.08 | −0.7 ± 0.01 | 42.2 ± 0.11 | 42.2 ± 0.11 | 91.0 ± 0.13 | 2.0 | 15.3 | 1.1 | 15.4 | ||
AS | 95.1 ± 0.21 | −1.0 ± 0.01 | 26.9 ± 0.06 | 26.9 ± 0.04 | 92.1 ± 0.11 | |||||||
ʟ−Phe-Bx | 4 | BS | 97.3 ± 0.19 | −1.2 ± 0.02 | 16.3 ± 0.08 | 16.4 ± 0.05 | 94.4 ± 0.10 | 1.3 | 10.5 | 2.0 | 10.6 | |
AS | 98.6 ± 0.27 | −0.7 ± 0.00 | 5.9 ± 0.05 | 5.9 ± 0.04 | 96.3 ± 0.21 | |||||||
6 | BS | 92.3 ± 0.15 | −0.2 ± 0.00 | 43.5 ± 0.09 | 43.5 ± 0.09 | 90.3 ± 0.14 | 42.4 | 30.8 | 1.6 | 52.4 | ||
AS | 49.9 ± 0.08 | 0.29 ± 0.01 | 12.7 ± 0.10 | 12.7 ± 0.03 | 88.7 ± 0.21 | |||||||
ʟ−Pro-Bx | 4 | BS | 93.6 ± 0.09 | 3.3 ± 0.03 | 43.9 ± 0.15 | 44.1 ± 0.09 | 85.7 ± 0.21 | 2.6 | 18.8 | 0.72 | 18.9 | |
AS | 96.2 ± 0.20 | 1.6 ± 0.00 | 25.3 ± 0.07 | 25.3 ± 0.03 | 86.4 ± 0.09 | |||||||
6 | BS | 93.3 ± 0.16 | 3.7 ± 0.02 | 47.4 ± 0.08 | 47.5 ± 0.07 | 85.5 ± 0.07 | 0.27 | 0.44 | 0.46 | 0.64 | ||
AS | 93.6 ± 0.11 | 4.1 ± 0.04 | 47.8 ± 0.08 | 48.0 ± 0.08 | 85.1 ± 0.19 |
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Cruz, S.; Checa, N.; Tovar, H.; Cejudo-Bastante, M.J.; Heredia, F.J.; Hurtado, N. Semisynthesis of Betaxanthins from Purified Betacyanin of Opuntia dillenii sp.: Color Stability and Antiradical Capacity. Molecules 2024, 29, 2116. https://doi.org/10.3390/molecules29092116
Cruz S, Checa N, Tovar H, Cejudo-Bastante MJ, Heredia FJ, Hurtado N. Semisynthesis of Betaxanthins from Purified Betacyanin of Opuntia dillenii sp.: Color Stability and Antiradical Capacity. Molecules. 2024; 29(9):2116. https://doi.org/10.3390/molecules29092116
Chicago/Turabian StyleCruz, Silvia, Neyder Checa, Hugo Tovar, María Jesús Cejudo-Bastante, Francisco J. Heredia, and Nelson Hurtado. 2024. "Semisynthesis of Betaxanthins from Purified Betacyanin of Opuntia dillenii sp.: Color Stability and Antiradical Capacity" Molecules 29, no. 9: 2116. https://doi.org/10.3390/molecules29092116