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

ABSTRACT: 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.

SUBMITTER: Adao P

PROVIDER: S-EPMC8156949 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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

Adão Pedro P Reboleira João J Teles Marco M Santos Beatriz B Ribeiro Nádia N Teixeira Carlos M CM Guedes Mafalda M Pessoa João Costa JC Bernardino Susana S

Molecules (Basel, Switzerland) 20210514 10

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 th ...[more]

PMID: 34068969

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Project description:Among the species belonging to the Aspergillus section Versicolores, Aspergillus creber has been poorly studied and still unexplored for its biological activities. The present study was undertaken to analyze A. creber extract and to evaluate its in vitro antimicrobial and anti-oxidant activities. UHPLC-MS/MS analysis of A. creber extract allowed the characterization of five known fungal metabolites including: asperlactone, emodin, sterigmatocystin, deoxybrevianamide E, and norsolorinic acid. The highest antimicrobial activity was displayed against Candida albicans, with a mean strongest inhibition zone of 20.6 ± 0.8 mm, followed by Gram-positive drug-resistant bacteria. The MIC values of A. creber extract varied from 0.325 mg/ml to 5 mg/ml. A. creber extract was shown a potent antioxidant activity and a high level of phenolic compounds by recording 89.28% scavenging effect for DPPH free radical, 92.93% in ABTS assay, and 85.76 mg gallic acid equivalents/g extract in Folin-Ciocalteu assay. To our knowledge, this is the first study concerning biological and chemical activities of A. creber species. Based on the obtained results, A. creber could be a promising source of natural antimicrobial and antioxidant compounds.Among the species belonging to the Aspergillus section Versicolores, Aspergillus creber has been poorly studied and still unexplored for its biological activities. The present study was undertaken to analyze A. creber extract and to evaluate its in vitro antimicrobial and anti-oxidant activities. UHPLC-MS/MS analysis of A. creber extract allowed the characterization of five known fungal metabolites including: asperlactone, emodin, sterigmatocystin, deoxybrevianamide E, and norsolorinic acid. The highest antimicrobial activity was displayed against Candida albicans, with a mean strongest inhibition zone of 20.6 ± 0.8 mm, followed by Gram-positive drug-resistant bacteria. The MIC values of A. creber extract varied from 0.325 mg/ml to 5 mg/ml. A. creber extract was shown a potent antioxidant activity and a high level of phenolic compounds by recording 89.28% scavenging effect for DPPH free radical, 92.93% in ABTS assay, and 85.76 mg gallic acid equivalents/g extract in Folin-Ciocalteu assay. To our knowledge, this is the first study concerning biological and chemical activities of A. creber species. Based on the obtained results, A. creber could be a promising source of natural antimicrobial and antioxidant compounds.

Dataset Information

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

Publications

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

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