دورية أكاديمية
أعرض في EDS

Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins.

التفاصيل البيبلوغرافية
العنوان: Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins.
المؤلفون: Esteves LC; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Machado CO; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Gonçalves LCP; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Cavalcante VF; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Obeid G; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Correra TC; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil., Bastos EL; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, SP, Brazil.
المصدر: Antioxidants (Basel, Switzerland) [Antioxidants (Basel)] 2022 Nov 16; Vol. 11 (11). Date of Electronic Publication: 2022 Nov 16.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI AG Country of Publication: Switzerland NLM ID: 101668981 Publication Model: Electronic Cited Medium: Print ISSN: 2076-3921 (Print) Linking ISSN: 20763921 NLM ISO Abbreviation: Antioxidants (Basel) Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI AG, [2012]-
مستخلص: 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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معلومات مُعتمدة: 2019/15412-9 (E.L.B.), 2021/06726-0 (T.C.C.), 2019/25634-9 (T.C.C.), 2020/08894-4 (G.O.), and 547 2015/24760-0 (C.O.M.) São Paulo Research Foundation; E.L.B, 301623/2019-8 National Council for Scientific and Technological Development; PIPAE 21.1.10424.1.9 Universidade de São Paulo; Finance code 001 Coordenação de Aperfeicoamento de Pessoal de Nível Superior
فهرسة مساهمة: Keywords: amino acids; betalains; betaxanthins; plant pigments; semisynthesis
تواريخ الأحداث: Date Created: 20221124 Latest Revision: 20221126
رمز التحديث: 20221213
مُعرف محوري في PubMed: PMC9686915
DOI: 10.3390/antiox11112259
PMID: 36421444
قاعدة البيانات: MEDLINE
الوصف
تدمد:2076-3921
DOI:10.3390/antiox11112259