Biosynthesis and metabolic actions of simple phenolic acids in plants

Marchiosi, Rogério; Santos, Wanderley Dantas dos; Constantin, Rodrigo Polimeni; Lima, Rogério Barbosa de; Soares, Anderson Ricardo; Finger-Teixeira, Aline; Mota, Thatiane Rodrigues; Oliveira, Dyoni Matias de; Foletto-Felipe, Marcela de Paiva; Abrahão, Josielle; Ferrarese-Filho, Osvaldo

doi:10.1007/s11101-020-09689-2

Cited by 246 publications

(160 citation statements)

References 219 publications

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“…The methylation of caffeoyl-CoA (activated form of caffeic acid) to feruloyl-CoA (activated form of ferulic acid) is catalyzed by caffeoyl-CoA O -methyltransferase. Then, feruloyl-CoA, is reduced by cinnamoyl-CoA reductase to form the coniferaldehyde and further by cinnamyl alcohol dehydrogenase to yield coniferyl alcohol [ 36 ].…”

Section: Resultsmentioning

confidence: 99%

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax

et al. 2021

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Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress response mechanisms has been, however, proposed. In this study, a non-targeted metabolomic analysis of the roots, stems, and leaves of wild-type and PLR1-RNAi transgenic flax, devoid of (+) secoisolariciresinol diglucoside ((+) SDG)—the main flaxseed lignan, was performed using 1H-NMR and LC-MS, in order to obtain further insight into the involvement of lignan in the response of plant to osmotic stress. Results showed that wild-type and lignan-deficient flax plants have different metabolic responses after being exposed to osmotic stress conditions, but they both showed the capacity to induce an adaptive response to osmotic stress. These findings suggest the indirect involvement of lignans in osmotic stress response.

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Section: Resultsmentioning

confidence: 99%

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax

et al. 2021

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“…Such a result may be related to the fact that phenylalanine and tyrosine are the precursors of the diverse family of phenylpropanoids [ 31 , 32 ]. Phenylalanine and tyrosine are precursors for the diverse group of phenylpropanoids, which include flavonoids, lignins, phenolic acids, stilbenes, and coumarins [ 33 ]. The connection between these two amino acids and the synthesis of phenolic compounds was also observed by Manela et al [ 34 ], while increasing the internal concentration of phenylalanine and tyrosine caused a significant increase in phenolic compounds in Vitis vinifera cell suspensions.…”

Section: Discussionmentioning

confidence: 99%

“…The connection between these two amino acids and the synthesis of phenolic compounds was also observed by Manela et al [ 34 ], while increasing the internal concentration of phenylalanine and tyrosine caused a significant increase in phenolic compounds in Vitis vinifera cell suspensions. Tryptophan is a precursor for alkaloids, glucosinolates, phytoalexins as well as auxins, while tyrosine for hydroxycinnamic acids, tocopherols, suberin and cyanogenic glycosides and phenylalanine is required for the biosynthesis of simple phenols [ 33 ].…”

Section: Discussionmentioning

confidence: 99%

Impact of Foliar Application of Amino Acids on Total Phenols, Phenolic Acids Content of Different Mints Varieties under the Field Condition

Tarasevičienė

Velička

Paulauskienė

2021

Plants

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Phenolic compounds have a number of benefits to human health and can be used as preventive compounds for the development of some chronic diseases. Mentha plants are not only a good source of essential oils, but also contain significant levels of wide range of phenolic compounds. The aim of this research was to investigate the possibility to increase phenols content in Mentha plants under the foliar application with L-phenylalanine, L-tryptophan, L-tyrosine at two concentrations (100 mg L−1 and 200 mg L−1) and to create preconditions for using this plant for even more diverse purposes. Quantitative and qualitative analyses of phenols in mints were performed by HPLC method. Foliar application of amino acids increased the total phenol content from 1.22 to 3.51 times depending on the treatment and mint variety. The most pronounced foliar application to total phenols content was tryptophane especially in Mentha piperita “Swiss”. Mentha piperita “Swiss” was affected most by foliar application and the amount of total phenolic acids depending on the treatment ranged from 159.25 to 664.03 mg 100 g−1 (DW), respectively, non-sprayed and sprayed with tryptophane 100 mg L−1. Our results suggest that the biophenol content varies according to such factors as foliar application and variety, and every single mint variety has individual response to different applications of amino acids.

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“…They also find wide-ranging application in medicine and agriculture in virtue of their antimicrobial, anti-inflammatory, and antitumoral activities [ 1 , 2 ]. Among the phenolic compounds, cinnamic acids are a group of aromatic carboxylic acids formed through the biochemical route of shikimate pathway, leading to the synthesis of lignin, the polymeric material that provides mechanical support to the plant cell wall [ 3 , 4 ]. p -Coumaric acid 1 , caffeic acid 2 , and ferulic acid 3 are the most common cinnamic acids, consisting of a trans -α, β-unsaturated carboxylic chain bonded to a phenol, catechol, and guaiacyl unit, respectively.…”

Section: Introductionmentioning

confidence: 99%

Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery

et al. 2021

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Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 µM and 7.8–125 µM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.

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Biosynthesis and metabolic actions of simple phenolic acids in plants

Cited by 246 publications

References 219 publications

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax

Impact of Foliar Application of Amino Acids on Total Phenols, Phenolic Acids Content of Different Mints Varieties under the Field Condition

Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery

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