scholarly journals Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions

2000 ◽  
Vol 346 (2) ◽  
pp. 265-273 ◽  
Author(s):  
Hideo IWAHASHI
Keyword(s):  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
High Performance ◽  
Octanoic Acid ◽  
Inhibitory Effects ◽  
Ferrous Ions ◽  
Acid Radical ◽  
Spin Resonance ◽  
Related Compounds

Effects of some polyphenols and their related compounds (chlorogenic acid, caffeic acid, quinic acid, ferulic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, 4-hydroxy-3-methoxybenzoic acid, salicylic acid, L-dopa, dopamine, L-adrenaline, L-noradrenaline, o-dihydroxybenzene, m-dihydroxybenzene, and p-dihydroxybenzene) on the formation of 13-hydroperoxide octadecadienoic (13-HPODE) acid-derived radicals (pentyl radical and octanoic acid radical) were examined. The ESR spin trapping showed that chlorogenic acid, caffeic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, L-dopa, dopamine, L-adrenaline, L-noradrenaline, and o-dihydroxybenzene inhibited the overall formation of 13-HPODE acid-derived radicals in the reaction mixture of 13-HPODE with ferrous ions. The ESR peak heights of α-(4-pyridyl-1-oxide)-N-tert-butylnitrone (4-POBN)/13-HPODE-derived radical adducts decreased to 46±4% (chlorogenic acid), 54±2% (caffeic acid), 49±2% (gallic acid), 55±1% [D-(+)-catechin], 60±3% [D-(-)-catechin], 42±1% (L-dopa), 30±2% (dopamine), 49±2% (L-adrenaline), 24±2% (L-noradrenaline), and 54±5% (o-dihydroxybenzene) of the control, respectively. The high performance liquid chromatography-electron spin resonance (HPLC-ESR) and high performance liquid chromatography-electron spin resonance-mass spectrometries (HPLC-ESR-MS) showed that caffeic acid inhibited the formation of octanoic acid radical and pentyl radical to 42±2% and 52±7% of the control, respectively. On the other hand, the polyphenols and their related compounds had few inhibitory effects on the radical formation in the presence of EDTA. Visible absorbance measurement revealed that all the polyphenols exhibiting the inhibitory effect chelate ferrous ions. Above results indicated that the chelation of ferrous ion is essential to the inhibitory effects of the polyphenols.

scholarly journals Changes of Polyphenol Compound Concentrations in Hybrids of Nante Type Carrots during Storage

2017 ◽  
Vol 71 (6) ◽  
pp. 492-495 ◽  
Author(s):  
Ingrīda Augšpole ◽  
Tatjana Kince ◽  
Ingmārs Cinkmanis
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
High Performance ◽  
Polyphenol Compounds ◽  
Polyphenol Compound

Abstract The main purpose of the study was to determine changes of polyphenol concentrations in hybrids of Nante type carrots during storage. Fresh Nante type ‘Forto’ variety carrots and carrot hybrids ‘Bolero’ F1, ‘Champion’ F1, and ‘Maestro’ F1 were cultivated in the Zemgale region of Latvia. Carrots were stored for six months in air (+3 ± 1 °C, RH = 89 ± 1%) and polyphenol compound concentrations were determined at two month intervals. High-performance liquid chromatography was used to determine concentrations of eight polyphenols in carrots: gallic acid, catechin, epicatechin, caffeic acid, chlorogenic acid, ferulic acid, vanillin, and rutin. Significant differences occurred in polyphenol concentrations of fresh Nante type variety ‘Forto’ carrots and several hybrids (‘Bolero’ F1, ‘Champion’ F1, and ‘Maestro’ F1) during storage. After six months of storage, the concentration of polyphenol compounds of Nante type carrots decreased — caffeic acid by 64.6%, chlorogenic acid — by 37.9% and vanillin — by 81.5%. However, during storage, concentration of some polyphenol compounds increased, as catechin by 30.5%, epicatechin by 85.2%, gallic acid by 48.5% and ferulic acid by 87.9%.

Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide

2001 ◽  
Vol 361 (1) ◽  
pp. 57-66 ◽  
Author(s):  
Hideo IWAHASHI ◽  
Koji NISHIZAKI ◽  
Ichiro TAKAGI
Keyword(s):  
Cytochrome C ◽  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Octanoic Acid ◽  
Linoleic Acid Hydroperoxide ◽  
Radical Intermediates ◽  
Acid Radical ◽  
Radical Adduct ◽  
Acid Hydroperoxide

A reaction of 13-hydroperoxide octadecadienoic acid (13-HPODE) with cytochrome c was analysed using ESR, HPLC–ESR and HPLC–ESR–MS by the combined use of the spin-trapping technique. The ESR, HPLC–ESR and HPLC–ESR–MS analyses showed that cytochrome c catalyses formation of pentyl and octanoic acid radicals from 13-HPODE. On the other hand, only the α-(4-pyridyl-1-oxide)-N-t-butylnitrone/octanoic acid radical adduct was detected in the elution profile of HPLC–ESR for a mixture of 13-HPODE with haematin, indicating that haematin catalyses the formation of octanoic acid radical. In addition, the reaction of 13-HPODE with cytochrome c was inhibited by chlorogenic acid, caffeic acid and ferulic acid via two possible mechanisms, i.e. reducing cytochrome c (chlorogenic acid and caffeic acid) and scavenging the radical intermediates (chlorogenic acid, caffeic acid and ferulic acid).

scholarly journals Relevance and Standardization of In Vitro Antioxidant Assays: ABTS, DPPH, and Folin–Ciocalteu

2018 ◽  
Vol 2018 ◽  
pp. 1-9 ◽  
Author(s):  
Helena Abramovič ◽  
Blaž Grobin ◽  
Nataša Poklar Ulrih ◽  
Blaž Cigić
Keyword(s):  
Ascorbic Acid ◽  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
Sulfonic Acid ◽  
Epigallocatechin Gallate ◽  
The Other ◽  
Oh Groups ◽  
Standard Compound

Trolox, gallic acid, chlorogenic acid, caffeic acid, catechin, epigallocatechin gallate, and ascorbic acid are antioxidants used as standards for reaction with chromogenic radicals, 2,2-diphenyl-1-picrylhydrazyl (DPPH⋅) and 2,2′-azino-bis-3-ethylbenzotiazolin-6-sulfonic acid (ABTS⋅+), and Folin–Ciocalteu (FC) reagent. The number of exchanged electrons has been analyzed as function of method and solvent. A majority of compounds exchange more electrons in FC assay than in ABTS and DPPH assays. In reaction with chromogenic radicals, the largest number of electrons was exchanged in buffer (pH 7.4) and the lowest reactivity was in methanol (DPPH) and water (ABTS). At physiological pH, the number of exchanged electrons of polyphenols exceeded the number of OH groups, pointing to the important contribution of partially oxidized antioxidants, formed in the course of reaction, to the antioxidant potential. For Trolox, small impact on the number of exchanged electrons was observed, confirming that it is more suitable as a standard compound than the other antioxidants.

scholarly journals Bioactive Plant Compounds in Coffee Charcoal (Coffeae carbo) Extract Inhibit Cytokine Release from Activated Human THP-1 Macrophages

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4263 ◽  
Author(s):  
Weber ◽  
Hammoud Mahdi ◽  
Jankuhn ◽  
Lipowicz ◽  
Vissiennon
Keyword(s):  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Inflammatory Diseases ◽  
Cytokine Signaling ◽  
Phytochemical Analysis ◽  
Inhibitory Effects ◽  
Plant Metabolites ◽  
Electron Microscopic ◽  
Secondary Plant Metabolites ◽  
Secondary Plant

The herbal preparation coffee charcoal is produced by over-roasting and milling green dried Coffea arabica L. seeds, and has a long-standing tradition in the treatment of inflammatory and gastrointestinal disorders. Its therapeutic properties are commonly attributed to adsorptive and astringent effects. This insufficiently explains its mode of action, especially when used in the treatment of inflammatory diseases in lower dosages. Our investigations aimed to identify bioactive secondary plant metabolites affecting cytokine-signaling. Thus, a phytochemical analysis of coffee charcoal extract was conducted using HPLC and LC/MS. Trigonelline, neochlorogenic acid, chlorogenic acid, caffeine, cryptochlorogenic acid, feruloylquinic acid isomers, and a caffeoylquinolacton were identified in the extract. Subsequently, the effects of coffee charcoal extract, chlorogenic acid isomers, their metabolite caffeic acid, caffeine, and trigonelline on cytokine (TNF, IL-6, MCP-1) release from LPS-challenged human THP-1 macrophages were examined to evaluate anti-inflammatory activity. Coffee charcoal showed concentration-dependent mild-to-medium inhibitory effects. The chlorogenic acid isomers and caffeic acid inhibited the TNF release, with cryptochlorogenic acid exerting the most distinct effects, as well as decreasing the release of IL-6 and MCP-1. In addition, scanning electron microscopic images provided an impression of the particle constitution, indicating a larger particle size and less structured surface of coffee charcoal in comparison to activated charcoal. In conclusion, our findings underline that beyond adsorptive effects, coffee charcoal exhibits pharmacological properties, which derive from a spectrum of secondary plant metabolites and support the therapeutic use in inflammatory diseases. Chlorogenic acids, particularly cryptochlorogenic acid, appear as pivotal bioactive compounds.

scholarly journals Anti-malarial Activity Of Phenolic Acids Is Structurally Related

2020 ◽  
Author(s):  
Prince A Fordjour ◽  
Jonathan P Adjimani ◽  
Bright Asare ◽  
Nancy O Duah-Quashie ◽  
Neils B Quashie
Keyword(s):  
Plasmodium Falciparum ◽  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Rosmarinic Acid ◽  
Protocatechuic Acid ◽  
Antimalarial Activity ◽  
Coumaric Acid

Abstract Background In the absence of an effective vaccine against malaria, chemotherapy remains a major option in the control of the disease. Then, the recent report of the emergence and spread of clones of Plasmodium falciparum resistant to available antimalarial drugs should be of concern as it poses a threat to disease control. Compounds whose pharmacological properties have been determined and touted for other disease can be investigated for antimalarial activity. Phenolic acids (polyphenols) have been reported to exhibit antioxidant, anticancer, anti-inflammatory, antiviral and antibiotic effects. However, information on their antimalarial activity is scanty. Phenolic acids are present in a variety of plant-based foods: mostly high in the skins and seeds of fruits as well as the leaves of vegetables. Systematic assessment of these compounds for antimalarial activity is therefore needed. Method Using the classical in vitro drug test, the antimalarial activities of five hydroxycinnamic acids, (caffeic acid, rosmarinic acid, chlorogenic acid, o-Coumaric acid and ferulic acid) and two hydroxybenzoic acids (gallic acid and protocatechuic acid) against 3D7 clones of Plasmodium falciparum was determined. Results Among the phenolic acids tested, caffeic acid and gallic acid were found to be the most effective, with mean IC 50 value of 17.73µg/ml and 26.59µg/ml respectively for three independent determinations. Protocatechuic acid had an IC 50 value of 30.08 µg/ml. Rosmarinic acid and chlorogenic acid, showed moderate antimalarial activities with IC 50 values of 103.59µg/ml and 105µg/ml respectively. The IC 50 values determined for ferulic acid and o-Coumaric acid were 93.36µg/ml and 82.23µg/ml respectively. Conclusion The outcome of this study suggest that natural occurring phenolic compounds have appreciable level of antimalarial activity which can be exploited for use through combination of actions/efforts including structural manipulation to attain an increase in their antimalarial effect. Eating of natural food products rich in these compounds could provide antimalarial prophylactic effect.

scholarly journals Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5802
Author(s):  
Yuji Iwaoka ◽  
Shoichi Suzuki ◽  
Nana Kato ◽  
Chisa Hayakawa ◽  
Satoko Kawabe ◽  
...  
Keyword(s):  
Gallic Acid ◽  
High Performance ◽  
Positive Control ◽  
Mass Spectrometry Analysis ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Spectrometry Analysis ◽  
Isolation And Characterization ◽  
Potential Food

In this study, we present the isolation and characterization of the structure of six gallotannins (1–6), three ellagitannins (7–9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unambiguously determined through nuclear magnetic resonance and circular dichroism analyses. The α-glucosidase activity and glycation inhibitory effects of the isolates were evaluated. Decarboxylated rugosin A (8) showed an α-glucosidase inhibitory activity, while hydrolyzable tannins revealed stronger antiglycation activity than that of the positive control. Furthermore, the identification and quantification of the TBE polyphenols were investigated by high-performance liquid chromatography coupled to ultraviolet detection and electrospray ionization mass spectrometry analysis, indicating the predominance of gallic acid, ellagic acid, and galloyl glucoses showing marked antiglycation properties. These findings suggest that there is a potential food industry application of polyphenols in TBE as a functional food with antidiabetic and antiglycation activities.

scholarly journals High-Performance Thin-Layer Chromatography Densitometric Method for the Simultaneous Determination of Three Phenolic Acids in Syzygium aromaticum (L.) Merr. & Perry

2008 ◽  
Vol 91 (5) ◽  
pp. 1169-1173 ◽  
Author(s):  
Subha Rastogi ◽  
Madan M Pandey ◽  
Ajay K S Rawat
Keyword(s):  
Thin Layer ◽  
Gallic Acid ◽  
Simultaneous Determination ◽  
Caffeic Acid ◽  
Correlation Coefficient ◽  
Phenolic Acids ◽  
High Performance ◽  
Syringic Acid ◽  
Syzygium Aromaticum

Abstract A simple, precise, and rapid high-performance thin-layer chromatographic (HPTLC) method has been developed for the simultaneous determination of 3 phenolic acids, i.e., gallic acid, caffeic acid, and syringic acid, in the dried buds of Syzygium aromaticum, commonly known as clove. HPTLC was performed on silica gel 60F254 plates with tolueneethyl acetateformic acid (8 2 1) mobile phase and densitometric scanning at 280 nm. The method was validated for selectivity, linearity, precision, and repeatability. Instrumental precision coefficient of variation (CV) was 0.88, 0.93, and 0.98% and repeatability of the method (CV) was 0.76, 0.64, and 0.69% for gallic acid, caffeic acid, and syringic acid, respectively. The linear concentration ranges were 4003200 ng/spot with a correlation coefficient of 0.993 for gallic acid, 4403520 ng/spot with a correlation coefficient of 0.994 for caffeic acid, and 4004000 ng/spot with a correlation coefficient of 0.993 for syringic acid. The average recoveries of gallic acid, caffeic acid, and syringic acid were 96.3, 95.7, and 92.4%, respectively. Gallic acid, caffeic acid, and syringic acid were present at levels of 1.58, 0.06, and 0.05% (w/w), respectively, in S. aromaticum. This method is simple, accurate, precise, and economical and can be used for routine quality control.

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