Antioxidant and antimicrobial activity of linseed lignans and phenolic acids

Kyselka, Jan; Rabiej, Dobrochna; Dragoun, Miroslav; Kreps, František; Burčová, Zuzana; Němečková, Irena; Smolová, Jana; Bjelková, Marie; Szydłowska‐Czerniak, Aleksandra; Schmidt, Štefan; Šarman, Luděk; Filip, V.

doi:10.1007/s00217-017-2871-9

Cited by 36 publications

(29 citation statements)

References 28 publications

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“…The activity of lactone 13 , obtained in small quantity, was not determined. Since the antimicrobial activity of ayanin, 2,6‐dimethoxybenzoic acid, methyl 3,4‐dihydroxycinnamate, 3,5‐dicaffeoylquinic acid, and chlorogenic acid has been extensively studied, they were not tested.…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition and Antimicrobial Activity of Ageratina deltoidea

Arciniegas

Pérez-Castorena

Meléndez-Aguirre

et al. 2018

Chemistry & Biodiversity

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The chemical study of Ageratina deltoidea afforded grandiflorenic acid (1), ent-kaurenoic acid (2), and eight benzylbenzoates (3 - 10), two of them, 3,5-dimethoxybenzyl 2,3,6-trimethoxybenzoate (5) and 4-(β-d-glucopyranosyloxy)-3-hydroxybenzyl 2,6-dimethoxybenzoate (9), described for the first time. In addition, the new sesquiterpene lactone deltoidin C (13), together with the known 11 and 12, the phenolic compounds: ayanin, 2,6-dimethoxybenzoic acid, methyl 3,4-dihydroxycinnamate, chlorogenic acid, and 3,5-dicaffeoylquinic acid were also isolated. The structures of these compounds were determined by spectroscopic methods and chemical reactions. The antibacterial and antifungal activities of compounds 1 - 12 were evaluated on Staphylococcus aureus, Escherichia coli, and Candida albicans. Deltoidin A (11) was the most active antibacterial agent (MIC 16.0 μg ml ) against E. coli, and the ent-kaurenoid derivatives (1 - 2) showed activity (MIC 31.0 μg ml ) against S. aureus.

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Section: Resultsmentioning

confidence: 99%

Chemical Composition and Antimicrobial Activity of Ageratina deltoidea

Arciniegas

Pérez-Castorena

Meléndez-Aguirre

et al. 2018

Chemistry & Biodiversity

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“…The results obtained by Takahashi and Miyazawa [ 82 ] showed that the DPPH radical scavenging activity order was: CFA > p -CA = CinA. Also data presented by other authors revealed that CFA was stronger antioxidant than p -CA [ 62 , 75 , 77 , 83 , 84 ]. While Szwajger et al [ 70 ] found that the DPPH free radical removal capability of the three investigated carboxylic acids was in the order: CinA > p -CA > BA with inhibition efficiency values of 35%, 27%, and 0%, respectively.…”

Section: Antioxidant Activity Of Nca Determined By Various Chemicamentioning

confidence: 98%

“…The radical scavenging activities were considerably higher when a catechol group was present in the chemical structure of compound (CFA, RA, ChA). CFA exhibited from 28.5% to 93.6% free radical removal capability [ 76 ], the minimal IC 50 value was 0.17 µmol/L [ 77 ]. RA is a naturally occurring caffeic acid ester with health promoting effects [ 78 ].…”

Section: Antioxidant Activity Of Nca Determined By Various Chemicamentioning

confidence: 99%

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

et al. 2020

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Natural carboxylic acids are plant-derived compounds that are known to possess biological activity. The aim of this review was to compare the effect of structural differences of the selected carboxylic acids (benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic acid (CFA), rosmarinic acid (RA), and chicoric acid (ChA)) on the antioxidant, antimicrobial, and cytotoxic activity. The studied compounds were arranged in a logic sequence of increasing number of hydroxyl groups and conjugated bonds in order to investigate the correlations between the structure and bioactivity. A review of the literature revealed that RA exhibited the highest antioxidant activity and this property decreased in the following order: RA > CFA ~ ChA > p-CA > CinA > BA. In the case of antimicrobial properties, structure-activity relationships were not easy to observe as they depended on the microbial strain and the experimental conditions. The highest antimicrobial activity was found for CFA and CinA, while the lowest for RA. Taking into account anti-cancer properties of studied NCA, it seems that the presence of hydroxyl groups had an influence on intermolecular interactions and the cytotoxic potential of the molecules, whereas the carboxyl group participated in the chelation of endogenous transition metal ions.

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“…23 In addition to their potential as substrates for bioconversion processes, aromatic LDMs are also valued as flavors, fragrances and antioxidants. 21,40 As these compounds are found in heterogeneous mixtures in treated lignin fractions, a system targeting these highly similar molecules specifically and directly from hydrolysates could prove useful for the recovery of particular LDMs. Such recovery might be useful also in cases, where the heterogeneous LDMs are converted into specified aromatics through microbial processes.…”

Section: Resultsmentioning

confidence: 99%

Molecular tools for selective recovery and detection of lignin-derived molecules

et al. 2018

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The pulp and paper industry together with lignocellulosic biofuel production provides plentiful streams of lignin and lignin-derived molecules (LDMs) that currently remain underutilized. The heterogeneity and complexity of lignin along with the lack of convenient tools significantly hamper its utilization. Selective separation of these LDMs from streams using specific tools would allow the recovery of aromatic compounds, as well as facilitate biological processes aiming at lignin valorization. To this end, here we report the isolation and characterization of single-chain variable fragment (scFv) antibodies against ferulate, coumarate, and caffeate, which are the molecular representatives of LDMs. Binders for the target LDMs were enriched by interrogating a synthetic scFv library with the phage display technique. As a result, scFv binders specific against each of the target molecules were obtained with affinities in the micromolar range. The selectivity of scFvs towards specific LDMs was proved by recovering caffeate from simulated LDM solution, Kraft lignin, and rice straw hydrolysate samples. Further proof of concept studies with model compounds demonstrated the applicability of antibody-based binders as a detection tool for monitoring microbial LDM conversion. Overall, this study demonstrates the potential of scFv binders as a specific toolset for lignin compound recovery and analysis.

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Antioxidant and antimicrobial activity of linseed lignans and phenolic acids

Cited by 36 publications

References 28 publications

Chemical Composition and Antimicrobial Activity of Ageratina deltoidea

Chemical Composition and Antimicrobial Activity of Ageratina deltoidea

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

Molecular tools for selective recovery and detection of lignin-derived molecules

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