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Article

Enhancement of the Antioxidant and Antimicrobial Activities of Porphyran through Chemical Modification with Tyrosine Derivatives

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MARE, Politécnico de Leiria, Edifício CETEMARES, Av. Porto de Pesca, 2520-630 Peniche, Portugal
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Centro Química Estrutural and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
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CDP2T and Department of Mechanical Engineering, Escola Superior de Tecnologia de Setúbal, Instituto Politécnico de Setúbal, 2910-761 Setúbal, Portugal
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CeFEMA, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
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MARE, Escola Superior de Turismo e Tecnologia do Mar, Politécnico de Leiria, Av. Porto de Pesca, 2520-630 Peniche, Portugal
*
Author to whom correspondence should be addressed.
Academic Editors: Michael Kontominas and Anastasia Badeka
Molecules 2021, 26(10), 2916; https://doi.org/10.3390/molecules26102916
Received: 16 April 2021 / Revised: 30 April 2021 / Accepted: 6 May 2021 / Published: 14 May 2021
(This article belongs to the Special Issue Antioxidant/Antimicrobial Packaging Films)
The chemical modification of porphyran hydrocolloid is attempted, with the objective of enhancing its antioxidant and antimicrobial activities. Sulfated galactan porphyran is obtained from commercial samples of the red algae Porphyra dioica using Soxhlet extraction with water at 100 °C and precipitation with isopropyl alcohol. The extracted porphyran is then treated with modified L-tyrosines in aqueous medium in the presence of NaOH, at ca. 70 °C. The modified tyrosines L1 and L2 are prepared through a Mannich reaction with either thymol or 2,4-di-tert-butylphenol, respectively. While the reaction with 2,4-di-tert-butylphenol yields the expected tyrosine derivative, a mixture of products is obtained with thymol. The resulting polysaccharides are structurally characterized and the respective antioxidant and antimicrobial activities are determined. Porphyran treated with the N-(2-hydroxy-3,5-di-tert-butyl-benzyl)-L-tyrosine derivative, POR-L2, presents a noticeable superior radical scavenging and antioxidant activity compared to native porphyran, POR. Furthermore, it exhibited some antimicrobial activity against S. aureus. The surface morphology of films prepared by casting with native and modified porphyrans is studied by SEM/EDS. Both POR and POR-L2 present potential applicability in the production of films and washable coatings for food packaging with improved protecting characteristics. View Full-Text
Keywords: modified porphyran; antioxidant activity; antimicrobial activity modified porphyran; antioxidant activity; antimicrobial activity
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MDPI and ACS Style

Adão, P.; Reboleira, J.; Teles, M.; Santos, B.; Ribeiro, N.; Teixeira, C.M.; Guedes, M.; Pessoa, J.C.; Bernardino, S. Enhancement of the Antioxidant and Antimicrobial Activities of Porphyran through Chemical Modification with Tyrosine Derivatives. Molecules 2021, 26, 2916. https://doi.org/10.3390/molecules26102916

AMA Style

Adão P, Reboleira J, Teles M, Santos B, Ribeiro N, Teixeira CM, Guedes M, Pessoa JC, Bernardino S. Enhancement of the Antioxidant and Antimicrobial Activities of Porphyran through Chemical Modification with Tyrosine Derivatives. Molecules. 2021; 26(10):2916. https://doi.org/10.3390/molecules26102916

Chicago/Turabian Style

Adão, Pedro, João Reboleira, Marco Teles, Beatriz Santos, Nádia Ribeiro, Carlos M. Teixeira, Mafalda Guedes, João C. Pessoa, and Susana Bernardino. 2021. "Enhancement of the Antioxidant and Antimicrobial Activities of Porphyran through Chemical Modification with Tyrosine Derivatives" Molecules 26, no. 10: 2916. https://doi.org/10.3390/molecules26102916

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