| Full text | |
| Author(s): |
Esteves, Larissa Cerrato
;
Machado, Caroline Oliveira
;
Pires Goncalves, Leticia Christina
;
Cavalcante, Victor Fernandes
;
Obeid, Guilherme
;
Correra, Thiago Carita
;
Bastos, Erick Leite
Total Authors: 7
|
| Document type: | Journal article |
| Source: | ANTIOXIDANTS; v. 11, n. 11, p. 19-pg., 2022-11-01. |
| 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. (AU) | |
| FAPESP's process: | 21/06726-0 - Investigation of reactive intermediates in complex chemical and biochemical processes |
| Grantee: | Thiago Carita Correra |
| Support Opportunities: | Research Grants - Young Investigators Grants - Phase 2 |
| FAPESP's process: | 20/08894-4 - Mechanistic characterization of organometallic reactions by nonconventional sampling techniques in mass spectrometry |
| Grantee: | Guilherme Obeid |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |
| FAPESP's process: | 19/25634-9 - Real-time reaction analysis in complex matrices by advanced mass spectrometry techniques |
| Grantee: | Thiago Carita Correra |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 15/24760-0 - Effect of antioxidant plant pigments on the viability of cells subjected to oxidative photoinduced stress |
| Grantee: | Caroline de Oliveira Machado |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |
| FAPESP's process: | 19/15412-9 - Conjugates of flower pigments and silica: smart and biocompatible hybrid materials |
| Grantee: | Erick Leite Bastos |
| Support Opportunities: | Regular Research Grants |