Phenolic Acid Amides Research Articles

Do Epichloë Endophytes and Their Grass Symbiosis Only Produce Toxic Alkaloids to Insects and Livestock?

Epichloë endophytes in forage grasses have attracted widespread attention and interest of chemistry researchers as a result of the various unique chemical structures and interesting biological activities of their secondary metabolites. This review describes the diversity of unique chemical structures of taxa from Epichloë endophytes and grass infected with Epichloë endophytes and demonstrates their reported biological activities. Until now, nearly 160 secondary metabolites (alkaloids, peptides, indole derivatives, pyrimidines, sesquiterpenoids, flavonoids, phenol and phenolic acid derivatives, aliphatic metabolites, sterols, amines and amides, and others) have been reported from Epichloë endophytes and grass infected with Epichloë endophytes. Among these, non-alkaloids account for half of the population of total metabolites, indicating that they also play an important role in Epichloë endophytes and grass infected with Epichloë endophytes. Also, a diverse array of secondary metabolites isolated from Epichloë endophytes and symbionts is a rich source for developing new pesticides and drugs. Bioassays disclose that, in addition to toxic alkaloids, the other metabolites isolated from Epichloë endophytes and symbionts have notable biological activities, such as antifungal, anti-insect, and phytotoxic activities. Accordingly, the biological functions of non-alkaloids should not be neglected in the future investigation of Epichloë endophytes and symbionts.

Insecticidal activity of phenolic acid amides against brown planthopper (BPH), Nilaparvata lugens (Stål) and their QSAR analysis

A series of 42 phenolic acid amides, synthesized using different phenolic acids (salicylic acid, 3-hydroxy cinnamic acid, p-coumaric acid, caffeic acid, ferulic acid, o-coumaric acid, cinnamic acid and amines (propyl amine, hexyl amine, heptyl amine, undecyl amine, hexadecyl amine, octadecyl amine) were screened for their insecticidal activities against Brown Planthopper (BPH), Nilaparvata lugens. These phenolic acid amides showed moderate to good insecticidal activity with the lowest LC50 value of 63.84 ppm from N-propyl-2-hydroxycinnamamide. 2D-Quantitative structural activity relationship (2D-QSAR) analysis of these phenolic acid amides was carried out by developing three different models namely multiple linear regression (MLR), principal component regression (PCR) and partial least squares (PLS). Statistical significance and predictive ability of these models were assessed by internal and external validation and verified by leave one-out cross-validation. PLS (model 3) was found best for QSAR study with correlation coefficient (r2) 0.8388, cross-validated correlation coefficient (q2) 0.7797 and r2 pred 0.7347. It was found that + vePotentialSurfaceArea, XAMostHydrophobic, SaasCE-index, T_O_O_3 and T_O_O_6 are the major descriptors which influence the insecticidal activities of these phenolic acid amides. The QSAR study could help in structural optimization of phenolic acid amides in developing potential compounds to get better bioefficacy against N. lugens.

Simultaneous quantification and identification of flavonoids, lignans, coumarin and amides in leaves of Zanthoxylum armatum using UPLC-DAD-ESI-QTOF–MS/MS

The current study presents isolation and characterization of twelve compounds including catechin (1), isovitexin (2), hesperidin (3), psoralin (4), eudesmin (5), kobusin (6), fargesin (7), sesamin (8), asarinin (9), planispine-A (10), α-sanshool (11) and vitexin (12), from the leaves of Zanthoxylum armatum. Further, two rapid and simple ultra performance liquid chromatography-diode array detection (UPLC-DAD) methods were developed for the simultaneous quantitative determination of isolated compounds from Z. armatum leaves. These analytical methods were validated for linearity, precision, accuracy, limit of detection (LOD) and limit of quantification (LOQ). The LOD and LOQ were in the range of 0.06–0.21μg/mL and 0.19–0.69μg/mL, respectively. The validated method was linear (R2≥0.9906), precise in terms of peak area (intra-day RSDs <3.8% and inter-day RSDs <2.7%), and accurate (109.6–92.5%). This is the first report on the isolation and quantification of 1, 2, 4 and 12 in Z. armatum and 3 in Zanthoxylum genus. The methods: were successfully applied to assess the quality of samples collected from different locations of Himachal Pradesh during summer and winter season. The results demonstrated that flavonoids and furofuran lignans were the major constituents in Z. armatum leaves. The developed methods: were further applied for tandem electrospray ionization-mass spectrometry (UPLC-DAD-ESI-MS/MS) and total eighteen compounds were identified including phenolic acid, flavonoids, furofuran lignans, coumarin and isobutyl amides.

Chemical constituents from Lindera nacusua (D. Don) Merr

This first phytochemical investigation on the roots of Lindera nacusua (D. Don) Merr led to the isolation of nine compounds, including demethylmacrosporine I (1), emodin-6-O-β-D-gluco- pyranoside (2), (−)-litsenolide D1 (3), (−)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methyilbu- tanolide (4), 1-O-3,4-dimethoxy-5-hydroxyphenyl-(6-O-3,5-dimethoxygalloyl)-β-d-glucopyranoside (5), 1-O-3,4-dimethoxy-5-hydroxyphenyl-(6-O-va-nilloyl)-β-d-glucopyranoside (6), (E)-feruloyltyra- mine (7), Z-N-feruloyltyramine (8), and 1-O-β-d-glucopyranosyl-(2S,3R,4E,8Z)-2-[2’(R)-hydroxyhex- adecanoyl-amino]-4,8-octadecadiene-1,3-diol (9). The types of the compounds involved anthraquinones (1, 2), γ-butanolides (3, 4), phenolic glycosides (5, 6), phenolic acid amides (7, 8) and cerebroside (9). Among them, Compounds 1–6 and 9 were firstly isolated from the genus Lindera as well as the Lauraceae family, and the anthraquinones and cerebrosides were first found in the Lauraceae family. The chemotaxonomic significance of these compounds was also summarized.

α-Glucosidase inhibitory activities of phenolic acid amides with l-amino acid moiety

Phenolic acid amides with a l-amino acid moiety showed excellent inhibitory activity on α-glucosidase.

A theoretical study of the antioxidant properties of phenolic acid amides investigated through the radical-scavenging and metal chelation mechanisms

Phenolic amides have been investigated extensively as efficient antioxidant compounds by means of experimental techniques. However, their mode of action has not been determined through the use of theoretical approaches. In this study, theoretical studies on the conformational and antioxidant properties of phenolic acid amides were performed to investigate factors that contribute to their conformational preferences and to elucidate their antioxidant properties and mechanisms. The antioxidant activity of selected phenolic acid amides has been considered through the ability of the compounds to scavenge free radical species and chelate metal ions. The antiradical mechanisms were investigated using the B3LYP/6-311+G(d,p) method, and the metal chelation mechanism was investigated using the B3LYP/6-311+G(3df,2p)//B3LYP/6-311+G(d,p) method. The results show that the preferred conformers for the neutral and anionic conformers are stabilised by the presence of intramolecular hydrogen bonds (IHBs). The neutral and cationic radical species are stabilised by both IHBs and the spin density delocalisation of the unpaired electron. The preferred Cu complex is one in which the Cu ion interacts simultaneously with the carbonyl group and the benzene ring of the aromatic amine moiety. An estimated metal ion affinity is influenced by the nature of the ligand and the media. In comparison with the isolated Cu(II) ion, the charge on the coordinated metal ion decreases from 2 to ~1 suggesting that the Cu ion is reduced on interaction with the ligand molecule undergoes oxidation.

The antioxidant properties of new dimer and two monomers of phenolic acid amides isolated from Limoniastrum guyonianum

Limoniastramide, a new dimer of phenolic acid amide, isolated from Limoniastrum guyonianum, along with two natural monomers N-E-caffeoyl tyramine (1) and N-E-feruloyl tyramine (2), using centrifugal partition chromatography (CPC). Their structures were determined on the basis of spectroscopic data analysis. We investigate the antioxidant activities of Limoniastrum amides using various in vitro assays. Results showed that N-E-feruloyl tyramine and N-E-caffeoyl tyramine exhibited the highest DPPH scavenging activity compared to the dimer (IC50=0.5, 0.6 and 6.5μg/ml, respectively). In addition, they have significant capacities to inhibit the bleaching of β-carotene. Limoniastramide presented the best activity with an IC50 value equal to 8μg/ml. Finally, the N-E-caffeoyl tyramine showed the highest reducing power (EC50=26μg/ml) compared to the other molecules. The present study found that L. guyonianum amides have effective in vitro antioxidant and radical scavenging activity which can be used in pharmacological and food industry due to their antioxidant properties.

Antioxidant activity and mechanism of action of some synthesised phenolic acid amides of aromatic amines

The antioxidative activities and mechanism of action were studied of eight synthesised cinnamoyl- and hydroxycinnamoyl amides of biogenic amines (caffeoyldopamine, cinnamoyldopamine, p-coumaroyldopamine, feruloyldopamine, sinapoyldopamine, caffeoylphenylethylamine, caffeoyltyramine, and caffeoyltryptamine) in a wide concentration range (2.5&amp;ndash;20 &amp;times; 10&lt;sup&gt;&amp;ndash;4&lt;/sup&gt;M) during autoxidation of triacylglycerols of sunflower oil. It was established that all amides exhibited excellent antioxidant activity, higher than or comparable with that of caffeic acid. The best activity was shown by caffeoyldopamine followed by cinnamoyldopamine and caffeoyltyramine. The analysis of the kinetic data obtained showed that the presence of hydroxyl groups in the amino part (derivatives of dopamine and tyramine) led to direct oxidation of the molecules during the process and stabilisation of the resulting radicals. In contrast, the amides without hydroxyl groups in the amino part participated in the side reaction with peroxides and the resulting radicals took part in one side reaction of the chain propagation as did caffeic acid. &amp;nbsp;

QTL Mapping of Tropical Maize Grain Components Associated with Maize Weevil Resistance

The maize weevil (MW), Sitophilus zeamais (Motsch.), is a globally distributed pest that causes severe losses in stored maize (Zea mays L.) worldwide. A previous study identified quantitative trait loci (QTL) contributing to reduced grain damage and losses by MW in the maize mapping population CML290 × Muneng‐8128C0HC1‐18‐2‐1‐1. This study was conducted to identify QTL associated with the identified biochemical bases of resistance in the maize grain. Eleven traits were analyzed on grain samples from F2 lines across two environments: p‐coumaric acid (p‐CA), cis‐ and trans‐ferulic acid (FA), four isomers of diferulic acids (DiFA), phenolic acid amides (p‐coumaroyl‐feruloyl putrescine [CFP] and diferuloyl putrescine [DFP]), total DiFA and total phenols acids (PhA). Significant variations were observed for most of the traits, while heritabilities ranged from 0.09 to 0.79. Ten QTL were identified for trans‐ and cis‐FA, 8,5′‐DiFA, 8‐O‐4′‐DiFA, 8,5′‐diferulic acid benzofuran form, DFP, and CFP while seven QTL were identified for p‐CA, 5,5′‐DiFA, FA, total DiFAs, and total PhA. These QTL were dispersed across the maize genome and explain between 25 and 47% of the phenotypic variance (σ2p) and 50 to 98% of the genotypic variance (σ2g). Nine regions were common between QTL associated with MW susceptibility and cell wall bound compounds, suggesting a strong genetic association with MW resistance in tropical maize.

Effects of phenolic acid esters and amides on stimulus-induced reactive oxygen species production in human neutrophils

Background Phenolic acids and their derivatives are widely distributed in plants. A series of phenolic acid esters and amides have been synthesized. Methods We determined the effects of phenolic acid derivatives on antiinflammatory activity against phorbol 12-myristate 13-acetate (PMA) and N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced production of superoxide anion, an inflammatory mediator produced by neutrophils. Results When the cells were preincubated with phenolic acids and their derivatives, the superoxide generation induced by fMLP (1.0 μmol/l) and PMA (0.16 μmol/l) was inhibited to various degrees with compounds 1, 2 and 4 significantly suppressing such generation in a concentration-dependent manner. Conclusion Phenolic acid derivatives may exert their antiinflammatory action through inhibiting superoxide generation.

Phenolic Acid Amides: A New Type of DNA Strand Scission Agent from Piper caninum.

Abstract In a survey of the active components of crude plant extracts for their ability to cleave DNA, a crude extract prepared from Piper caninum was found to induce the relaxation of supercoiled pBR322 plasmid DNA in the presence of Cu 2+ . Bioassay-guided fractionation was carried out on this extract, guided by an in vitro DNA strand scission assay. Three active principles were isolated and identified as N - cis -feruloyl tyramine ( 1 ), N - trans -feruloyl tyramine ( 2 ), and 1-cinnamoylpyrrolidine ( 3 ). Compounds 1 – 3 represent a structurally new type of DNA strand scission agent.

Phenolic acid amides: a new type of DNA strand scission agent from Piper caninum

In a survey of the active components of crude plant extracts for their ability to cleave DNA, a crude extract prepared from Piper caninum was found to induce the relaxation of supercoiled pBR322 plasmid DNA in the presence of Cu 2+. Bioassay-guided fractionation was carried out on this extract, guided by an in vitro DNA strand scission assay. Three active principles were isolated and identified as N- cis-feruloyl tyramine ( 1), N- trans-feruloyl tyramine ( 2), and 1-cinnamoylpyrrolidine ( 3). Compounds 1– 3 represent a structurally new type of DNA strand scission agent.

Phenolic acid amides of phenolic benzylamines against UVA‐induced oxidative stress in skin¶

UVA-radiation is suspected to be a main cause for extrinsic skin ageing in humans. Recent studies showed that topically administered molecular antioxidants are able to protect skin against UVA-generated oxidative stress. Therefore, new phenolic acid amides of phenolic benzylamines were synthesized as potential antioxidants by reaction of (if necessary protected) N-succinimidylesters of ferulic acid, sinapic acid, caffeic acid, 3-(4-hydroxy-3-methoxyphenyl)propanoic acid, 3-(3,4-dihydroxyphenyl)propanoic acid, 2-(4-hydroxy-3-methoxyphenyl)acetic acid and 2-(3,4-dihydroxyphenyl) acetic acid with different phenolic benzylamines in moderate to good yields. The radical scavenging activities of the compounds were determined by the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay and by a superoxide radical anion trapping assay. Antioxidant activities in bulk lipids were tested by accelerated peroxidation with or without test compounds performed in the Rancimat apparatus. Stripped soybean oil and the skin sebum component squalene were used as lipids. The synthesized compounds were found to be efficient radical scavengers and antioxidants, especially the hydroxyphenylacetic amides and the hydroxydihydrocinnamic acid amides of polyhydroxybenzylamines, which are superior to the standards alpha-tocopherol and l-ascorbic acid. A topically applied 0.1% 1,3-butyleneglycol solution of N-(3,4-dihydroxybenzyl)-2-(4-hydroxy-3-methoxyphenyl)acetic acid amide 19 inhibits the UVA-induced sebum peroxidation in human skin significantly, by 39%.

Distribution and Microchemical Detection of Phenolic Acids, Flavonoids, and Phenolic Acid Amides in Maize Kernels

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDistribution and Microchemical Detection of Phenolic Acids, Flavonoids, and Phenolic Acid Amides in Maize KernelsAlok Sen, David Bergvinson, S. Shea Miller, Jeffrey Atkinson, R. Gary Fulcher, and J. Thor ArnasonCite this: J. Agric. Food Chem. 1994, 42, 9, 1879–1883Publication Date (Print):September 1, 1994Publication History Published online1 May 2002Published inissue 1 September 1994https://doi.org/10.1021/jf00045a009RIGHTS & PERMISSIONSArticle Views589Altmetric-Citations53LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (3 MB) Get e-Alerts Get e-Alerts

Determination of Additives in Polyethylene for Food Packaging

Methods were developed for the systematic determination of five classes of additives. These classes are: phenolic antioxidants, acid amides, glycerin fatty acid esters, thiodipropionic acid esters and stearates.Polyethylene packages were Soxhlet-extracted with chloroform or chloroform-hydrochloric acid (only for stearates) for four hours. The extracts were concentrated and the phenolic antioxidants and acid amides were determined by high performance liquid chromatography (HPLC) and capillary (high-resolution) gas chromatography (HRGC), respectively. Thiodipropionic acid esters were determined by HRGC as higher alcohols obtained after saponification of extracts with potassium hydroxide-methanol. Glycerin fatty acid esters and stearates were determined by HRGC as their fatty acid methyl esters obtained after methylation of extracts. In these methods, additives were well separated by HPLC or HRGC, although the retention times of Antage W-300 and Antage W-400 were close. No additives could be detected in commercial polyethylene packages of milk.