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Enhancement of the antioxidant and antimicrobial activities of porphyran through chemical modification with tyrosine derivatives

2021Journal article Open access
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dc.contributor.authorAdão, Pedro
dc.contributor.authorReboleira, João
dc.contributor.authorTeles, Marco
dc.contributor.authorSantos, Beatriz
dc.contributor.authorRibeiro, Nádia
dc.contributor.authorTeixeira, Carlos M.
dc.contributor.authorGuedes, Mafalda
dc.contributor.authorPessoa, João Costa
dc.contributor.authorBernardino, Susana M.
dc.date.accessioned2021-07-27T14:23:05Z
dc.date.available2021-07-27T14:23:05Z
dc.date.issued2021
dc.descriptionThe 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.
dc.description.abstractThe 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAdão, 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/molecules 26102916pt_PT
dc.identifier.doi10.3390/molecules 26102916pt_PT
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.8/5944
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationMARE - Marine and Environmental Sciences Centre
dc.relationMarine and Environmental Sciences Centre
dc.relationCentro de Química Estrutural
dc.relationNew 8-hydroxyquinoline metallodrugs: synthesis, speciation and uptake
dc.relationAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
dc.relationCenter of Physics and Engineering of Advanced Materials
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectModified porphyranpt_PT
dc.subjectAntioxidant activitypt_PT
dc.subjectAntimicrobial activitypt_PT
dc.titleEnhancement of the antioxidant and antimicrobial activities of porphyran through chemical modification with tyrosine derivativespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleMARE - Marine and Environmental Sciences Centre
oaire.awardTitleMarine and Environmental Sciences Centre
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleNew 8-hydroxyquinoline metallodrugs: synthesis, speciation and uptake
oaire.awardTitleAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
oaire.awardTitleCenter of Physics and Engineering of Advanced Materials
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FCTM%2F04540%2F2019/PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume26pt_PT
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person.familyNameAdão
person.familyNameMendes Reboleira
person.familyNameTeles
person.familyNameBernardino
person.givenNamePedro
person.givenNameJoão
person.givenNameMarco
person.givenNameSusana
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