Enzymatic transformation of tyrosol by Trametes trogii laccases: Identification of the product and study of its biological activities

Chakroun, Hanen; Bouaziz, Mohamed; Yangui, Thabèt; Blibech, Imen; Dhouib, Abdelhafidh; Sayadi, Sami

doi:10.1016/j.molcatb.2012.10.006

Cited by 12 publications

(3 citation statements)

References 46 publications

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“…TEMPO-based LMSs were shown to be the best catalytic systems in the oxidation of different recalcitrant compounds . LMSs oxidize polyphenols by radical cross-coupling reactions, oxidative ring-opening reactions, and aromatic ring hydroxylations. , The oxidation of catechins to theaflavins by laccases is recognized as a model for the chemical transformation of green tea into black tea . Moreover, laccases and vanillin (i.e., a natural redox mediator) act as sensoring systems to analyze poplar hydrolysates .…”

Section: Introductionmentioning

confidence: 99%

Laccase-Mediated Enhancement of the Antioxidant Activity of Propolis and Poplar Bud Exudates

et al. 2017

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The treatment of propolis and poplar bud exudates with laccase from Trametes versicolor and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical increased the antioxidant activity, as evaluated by the 2,2′-diphenyl picrylhydrazyl (DPPH)- and t-butyl-OOH-induced DNA breakage comet assay analyses. The effect was highest for shorter reaction times. Propolis showed the highest antioxidant activity in the DPPH test, whereas poplar bud exudates were more active in reducing the t-butyl-OOH-induced lesions in the Chinese hamster ovary cell line. Even if the concentration of polyphenols decreased during the oxidation, the formation of low-molecular-weight phenols phloroglucinol 4 (1,3,5-trihydroxy benzene), hydroquinone 5 (1,4-dihydroxy benzene), and catechol 6 (1,2-dihydroxy benzene), characterized by the radical-scavenging activity, can account for the observed increase in the antioxidant activity.

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Section: Introductionmentioning

confidence: 99%

Laccase-Mediated Enhancement of the Antioxidant Activity of Propolis and Poplar Bud Exudates

et al. 2017

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“…One of these oligomers was described as a dimer with a structure arising from an ortho-ortho oxidative phenolic coupling. Chakroun and collaborators have also described the formation of Tyr dimers after enzymatic oxidation using laccase at pH 5 [41] with a structure different from those presented in [40]. The product ions of T 5 at m/z 255 and at m/z 243, which correspond to a loss of water and H 2 C = O unit, did not lead to select the structure of T 5 among the two already proposed structures.…”

Section: Characterization Of Products By Lc-ms 2 After Electrochemical Oxidation Of Tyrmentioning

confidence: 94%

UV-Vis Spectroelectrochemistry of Oleuropein, Tyrosol, and p-Coumaric Acid Individually and in an Equimolar Combination. Differences in LC-ESI-MS2 Profiles of Oxidation Products and Their Neuroprotective Properties

et al. 2019

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Major phenolic compounds from olive oil (ArOH-EVOO), oleuropein (Ole), tyrosol (Tyr), and p-coumaric acid (p-Cou), are known for their antioxidant and neuroprotective properties. We previously demonstrated that their combination could potentiate their antioxidant activity in vitro and in cellulo. To further our knowledge of their electron-transfer properties, Ole, Tyr, and p-Cou underwent a spectroelectrochemical study, performed either individually or in equimolar mixtures. Two mixtures (Mix and Mix-seq) were prepared in order to determine whether distinct molecules could arise from their simultaneous or sequential oxidation. The comparison of Liquid Chromatography–Electrospray Ionization–Tandem Mass Spectrometry (LC-ESI-MS2) profiles highlighted the presence of specific oxidized products found in the mixes. We hypothesized that they derived from the dimerization between Tyr and Ole or p-Cou, which have reacted either in their native or oxidized forms. Moreover, Ole regenerates when the Mix undergoes oxidation. Our study also showed significant neuroprotection by oxidized Ole and oxidized Mix against H2O2 toxicity on SK-N-SH cells, after 24 h of treatment with very low concentrations (1 and 5 nM). This suggests the putative relevant role of oxidized Ole products to protect or delay neuronal death.

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“…The enhanced antimicrobial activity could be attributed to oxidative products formed due to the enzymatic treatment. It has been proposed that due to the laccase-catalyzed oxidation of phenolic compounds, oligomeric phenolic compounds are formed that present higher antimicrobial activity than the precursor compounds [77,78]. Even though the exact mechanism of action of the oligomers against the bacteria has not been elucidated; it is attributed to factors such as the higher electron delocalization and the branched nature of the produced oligomers [78].…”

Section: Antimicrobial Activity Of Starting and Enzyme-treated Extractsmentioning

confidence: 99%

Fungal Laccase-Mediated Enhancement of the Bioactivity of Green Algae Extracts

Spyrou¹,

Chatzikonstantinou²,

Giannakopoulou³

et al. 2023

Catal Res

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Biomass derived from green marine macroalgae Ulva sp. is considered a rich source of bioactive compounds. In the present study, we demonstrate the increased bioactivity of a phenolic-rich extract derived from green marine macroalgae Ulva intestinalis after its treatment with fungal laccases from Trametes versicolor and Agaricus bisporus. The phenolic composition of the extract, before and after its enzymatic treatment, was determined through several analytical methods. Furthermore, the antioxidant, enzyme-inhibitory, antimicrobial and cytotoxic activity of enzymatically modified and non-modified extracts was comparatively investigated. Depending on the laccase used, the enzyme-modified extracts exhibited different phenolic content and enhanced bioactivities compared to the non-treated ones. The enzymatically modified extracts presented enhanced antimicrobial, anti-lipoxygenase and anti-collagenase activities, and mild cytotoxicity. These results indicate that the proposed biocatalytic process could be applied to produce green macroalgal natural extracts with enhanced bioactivities paving the way for their implementation in the food, pharmaceutical, and cosmeceutical industries.

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Enzymatic transformation of tyrosol by Trametes trogii laccases: Identification of the product and study of its biological activities

Cited by 12 publications

References 46 publications

Laccase-Mediated Enhancement of the Antioxidant Activity of Propolis and Poplar Bud Exudates

Laccase-Mediated Enhancement of the Antioxidant Activity of Propolis and Poplar Bud Exudates

UV-Vis Spectroelectrochemistry of Oleuropein, Tyrosol, and p-Coumaric Acid Individually and in an Equimolar Combination. Differences in LC-ESI-MS2 Profiles of Oxidation Products and Their Neuroprotective Properties

Fungal Laccase-Mediated Enhancement of the Bioactivity of Green Algae Extracts

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