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

Autor: Susana M. Bernardino, João Costa Pessoa, Mafalda Guedes, Beatriz Santos, João Reboleira, Pedro Adão, Carlos M. Teixeira, Marco Teles, Nádia Ribeiro
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Staphylococcus aureus
Antioxidant
medicine.medical_treatment
Proton Magnetic Resonance Spectroscopy
Pharmaceutical Science
Organic chemistry
antioxidant activity
Microbial Sensitivity Tests
Antimicrobial activity
Polysaccharide
Antioxidants
Article
Analytical Chemistry
chemistry.chemical_compound
QD241-441
Antioxidant activity
Anti-Infective Agents
Picrates
Drug Discovery
Spectroscopy
Fourier Transform Infrared
medicine
Escherichia coli
Benzothiazoles
modified porphyran
Physical and Theoretical Chemistry
Thymol
chemistry.chemical_classification
Porphyra
antimicrobial activity
Porphyran
Sepharose
Biphenyl Compounds
Chemical modification
Isopropyl alcohol
Galactan
Antimicrobial
Aerobiosis
chemistry
Chemistry (miscellaneous)
Molecular Medicine
Tyrosine
Spectrophotometry
Ultraviolet
Sulfonic Acids
Oxidation-Reduction
Modified porphyran
Nuclear chemistry
Zdroj: Molecules
Volume 26
Issue 10
Molecules, Vol 26, Iss 2916, p 2916 (2021)
Repositório Científico de Acesso Aberto de Portugal
Repositório Científico de Acesso Aberto de Portugal (RCAAP)
instacron:RCAAP
ISSN: 1420-3049
DOI: 10.3390/molecules26102916
Popis: The authors of MARE-Politécnico de Leiria acknowledge the MARE-Marine and Environmental Sciences Centre, Instituto Politécnico de Leiria, which is financed by national funds from FCT/MCTES (UID/MAR/04292/2019, UIDB/04292/2020) and the project “SmartBioR-Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER). The authors of Centro de Química Estrutural acknowledge the financial support of Fundação para a Ciência e a Tecnologia (UIDB/0100/2020), the IST-UL Centers of the Portuguese NMR and Mass Spectrometry Networks (REM2013, RNNMR), RECI/QEQ-QIN/0189/2012, RECI/QEQ-MED/0330/2012, grants SFRH/BD/135797/2018 and PD/BD/106078/2015. FCT is also acknowledged through CeFEMA, under the strategic project UID/CTM/04540/2019. 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 100ºC 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. 70ºC. 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. info:eu-repo/semantics/publishedVersion
Databáze: OpenAIRE
Externí odkaz: