Changes in Browning Degree and Reducibility of Polyphenols during Autoxidation and Enzymatic Oxidation

In the present study, the browning degree and reducing power of browning products of catechin (CT), epicatechin (EC), caffeic acid (CA), and chlorogenic acid (CGA) in autoxidation and enzymatic oxidation were investigated. Influencing factors were considered, such as pH, substrate species and composition, and eugenol. Results show that polyphenols’ autoxidation was intensified in an alkaline environment, but the reducing power was not improved. Products of enzymatic oxidation at a neutral pH have higher reducing power than autoxidation. In enzymatic oxidation, the browning degree of mixed substrates was higher than that of a single polyphenol. The reducing power of flavonoid mixed solution (CT and EC) was higher than those of phenolic acids’ (CA and CGA) in autoxidation and enzymatic oxidation. Eugenol activity studies have shown that eugenol could increase autoxidation browning but inhibit enzymatic browning. Activity test and molecular docking results show that eugenol could inhibit tyrosinase.

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Concentrations of Phenolic Acids Are Differently Genetically Determined in Leaves, Flowers, and Grain of Common Buckwheat (Fagopyrum esculentum Moench)

Plants ◽

10.3390/plants10061142 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1142

Author(s):

Alena Vollmannová ◽

Janette Musilová ◽

Judita Lidiková ◽

Július Árvay ◽

Marek Šnirc ◽

...

Keyword(s):

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Sinapic Acid ◽

Fagopyrum Esculentum ◽

Blood Cholesterol ◽

Common Buckwheat ◽

High Concentration ◽

Phenolic Substances ◽

Fagopyrum Esculentum Moench

Common buckwheat (Fagopyrum esculentum Moench) is a valuable source of proteins, B vitamins, manganese, tryptophan, phytochemicals with an antioxidant effect, and the natural flavonoid rutin. Due to its composition, buckwheat supports the human immune system, regulates blood cholesterol, and is suitable for patients with diabetes or celiac disease. The study aimed to compare the allocation of selected phenolic acids (neochlorogenic acid, chlorogenic acid, trans-caffeic acid, trans-p-coumaric acid, trans-sinapic acid, trans-ferulic acid) and flavonoids (rutin, vitexin, quercetin, kaempferol) in the leaves, flowers, and grain of buckwheat cultivars of different origin. The content of individual phenolics was determined by the HPLC-DAD method. The results confirmed the determining role of cultivar on the relative content of chlorogenic acid, trans-caffeic acid, trans-sinapic acid, vitexin, and kaempferol in buckwheat plants. A significantly negative correlation among concentrations of phenolic acids in different common buckwheat plant parts shows that there are different mechanisms of genetic influences on the concentration of phenolic substances in common buckwheat flowers, leaves, and grain. These differences should be taken into account when breeding buckwheat for a high concentration of selected phenolic substances.

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Involvement of Phenolics, Flavonoids, and Phenolic Acids in High Yield Characteristics of Rice (Oryza Sativa L.)

International Letters of Natural Sciences ◽

10.18052/www.scipress.com/ilns.68.19 ◽

2018 ◽

Vol 68 ◽

pp. 19-26 ◽

Cited By ~ 3

Author(s):

Tran Dang Xuan ◽

Do Tuan Bach ◽

Tran Dang Dat

Keyword(s):

Ferulic Acid ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Sinapic Acid ◽

Development Stage ◽

Vegetative Stage ◽

High Yield ◽

Phenolic Contents ◽

The Difference

The present study examined the correlation between phenolic acids and flavonoids with high rice yield traits of rice. It was observed that the difference of phenolic contents among the tested rice lines occurred only in the vegetative stage. The concentrations of phenolic acids were higher in the rice high yield cultivars than low yield variety in the vegetative stage, but they either decreased dramatically or disappeared during the development stage. Caffeic acid was found only in high yield rice, whereas chlorogenic acid was detected only in low yield rice. Sinapic acid was the dominant phenolic acid in high yield cultivars at vegetative stage (3.7 mg/g), followed by ferulic acid (1.2 mg/g). These findings suggest that caffeic acid, ferulic acid, sinapic acid and chlorogenic acid may play a particular role in forming yield components in rice. The cultivar B3 contained high amount of sinapic acid may be used as a natural source for pharmaceutical use.

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Anti-malarial Activity Of Phenolic Acids Is Structurally Related

10.21203/rs.3.rs-21702/v1 ◽

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.

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Dietary chlorogenic acid supplementation affects gut morphology, antioxidant capacity and intestinal selected bacterial populations in weaned piglets

Food & Function ◽

10.1039/c8fo01126e ◽

2018 ◽

Vol 9 (9) ◽

pp. 4968-4978 ◽

Cited By ~ 12

Author(s):

Yong Zhang ◽

Yu Wang ◽

Daiwen Chen ◽

Bing Yu ◽

Ping Zheng ◽

...

Keyword(s):

Antioxidant Capacity ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Quinic Acid ◽

Weaned Piglets ◽

Gut Morphology ◽

Bacterial Populations ◽

Acid Supplementation

Chlorogenic acid (CGA), an ester formed between caffeic acid and quinic acid, is one of the most abundant phenolic acids in plants.

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PHYTOCHEMICAL INVESTIGATION AND EVALUATION OF IN VITRO ANTIOXIDANT ACTIVITY OF THE PLANT CYPERUS TEGETUM ROXB

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2019.v12i11.34325 ◽

2019 ◽

pp. 18-23

Author(s):

ATANU CHATTERJEE ◽

RITU KHANRA ◽

PRANABESH CHAKRABORTY ◽

HIMANGSHU SEKHAR MAJI

Keyword(s):

Antioxidant Activity ◽

Phenolic Compounds ◽

Ferulic Acid ◽

Chlorogenic Acid ◽

Gallic Acid ◽

Caffeic Acid ◽

Hplc Analysis ◽

Reducing Power ◽

Spectral Studies ◽

Isolated Compound

Objective: The objective of the present study is to isolate the lead molecules and the antioxidant activity is also evaluated. Method: Cyperus tegetum Roxb. (Cyperaceae) is found in the tribal area of West Midnapur district of West Bengal, India. It is commonly known as Madur Kathi. Different chromatographic techniques, namely, thin-layer chromatography, column chromatography, and high-performance liquid chromatography (HPLC) were used to isolate and identify the different secondary metabolites. Results: The different spectral studies (nuclear magnetic resonance [NMR], infrared [IR], and ultraviolet [UV]) confirmed the presence of stigmasterol as an isolated compound from the extract of C. tegetum (ECT). HPLC analysis revealed the presence of flavonoids, namely, rutin (retention time [Rt]: 3.00), myricetin (Rt: 3.9), and quercetin (Rt: 5.6) and phenolic acids, namely, gallic acid (Rt: 4.0), caffeic acid (Rt: 5.4), chlorogenic acid (Rt: 7.3), and ferulic acid (Rt: 8.8) in ECT. ECT showed strong reducing power, diphenyl-2-picrylhydrazyl hydrate radical, superoxide anion scavenging, and hydrogen peroxide scavenging activities when compared to standard compounds. Conclusion: From this study, several flavonoid and phenolic compounds were identified by RP-HPLC analysis. Flavonoids are rutin, quercetin, and myricetin and phenolic compounds are gallic acid, ferulic acid, chlorogenic acid, and caffeic acid, respectively. The different spectral studies (NMR, IR, and UV) confirmed the presence of stigmasterol as an isolated compound from ECT.

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Polyphenols, Flavonoids, and Antioxidant Activity Involved in Salt Tolerance in Wheat, Aegilops cylindrica and Their Amphidiploids

Frontiers in Plant Science ◽

10.3389/fpls.2021.646221 ◽

2021 ◽

Vol 12 ◽

Author(s):

Razieh Kiani ◽

Ahmad Arzani ◽

S. A. M. Mirmohammady Maibody

Keyword(s):

Salt Stress ◽

Salt Tolerance ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Reducing Power ◽

Total Phenolic ◽

Coumaric Acid ◽

Wheat Cultivars ◽

Aegilops Cylindrica ◽

Phenolic Components

Aegilops spp. is the closest genus to wheat (Triticum spp.), which makes Aegilops great candidates to exhibit precursors of wheat features. Aegilops cylindrica Host displays excellent salt tolerance. In the current study, biochemical and phytochemical compounds in the leaves of two wheat cultivars, one hyper-salt tolerant Ae. cylindrica genotype and their amphidiploids (derived from “Chinese Spring” × Ae. cilindrica and “Roshan” × Ae. cylindrica), grown under control and saline field conditions, were assessed. These compounds included total protein content, proline content, electrolyte leakage, total flavonoid content, total phenolic content, DPPH radical scavenging activity, and reducing power. In addition, phenolic components were also identified using HPLC analysis. Chlorogenic acid, ellagic acid, ferulic acid, syringic acid, vanillic acid, p-coumaric acid, caffeic acid, and gallic acid were the most abundant phenolic acids. Luteolin, apigenin, and rutin were the most abundant flavonoids in the leaves. Salt stress significantly increased all biochemical variables, with the exceptions of reducing power and p-coumaric acid. Interestingly, amphidiploid genotypes exhibited intermediate levels of most of the detected phenolic compounds between the two parental species. As demonstrated by bivariate correlations luteolin, chlorogenic acid, caffeic acid and apigenin could predict inhibition percentage by DPPH assay, suggesting a possible role in the cellular defense against oxidative stress in wheat. The amphidiploids and their wild parent performed significantly better than wheat cultivars on phenolic constituents, flavonoids, and maintaining redox homeostasis under salt stress conditions.

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Mammillaria Species—Polyphenols Studies and Anti-Cancer, Anti-Oxidant, and Anti-Bacterial Activities

Molecules ◽

10.3390/molecules25010131 ◽

2019 ◽

Vol 25 (1) ◽

pp. 131 ◽

Cited By ~ 10

Author(s):

Hosam O. Elansary ◽

Agnieszka Szopa ◽

Marta Klimek-Szczykutowicz ◽

Karolina Jafernik ◽

Halina Ekiert ◽

...

Keyword(s):

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Sinapic Acid ◽

Jurkat Cells ◽

Gentisic Acid ◽

Natural Product Research ◽

Anti Cancer ◽

Anti Oxidant ◽

Mcf 7

Discovering new natural resources of polyphenols is the aim of many recent studies in the field of natural product research. This study tentatively investigated the polyphenols profile of the stems of seven Mammillaria species (M. rhodantha, M. spinosissima, M. hahniana, M. crucigera, M. candida, M. albilanata, and M. muehlenpfordtii) using high performance liquid chromatography with DAD detector (HPLC-DAD) method. Furthermore, the anti-cancer, anti-oxidant, and anti-bacterial potentials of these extracts as well as major identified phenols were explored. The HPLC-DAD study confirmed the availability of six phenolic acids, including gentisic acid, chlorogenic acid, caffeic acid, protocatechuic acid, sinapic acid, and p-hydroxybenzoic acid. The dominant compounds were: gentisic acid in M. rhodantha and M. spinosissima; chlorogenic acid in M. muehlenpfordtii, M. crucigera, and M. rhodantha; and caffeic acid in M. rhodantha, M. crucigera, and M. spinosissima. Stems of Mammillaria sp. showed antiproliferative effects against HeLa, MCF-7, and Jurkat cells. In HeLa and MCF-7 cells, the best antiproliferative activities were found in the treatments with M. rhodantha, M. spinosissima, and M. muehlenpfordtii. The apoptotic assay of M. rhodantha, M. spinosissima, and M. muehlenpfordtii showed accumulation of necrotic cells in the early and late apoptotic phase. M. rhodantha, M. spinosissima, and M. muehlenpfordtii showed the highest anti-oxidant activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene bleaching, and ferric reducing anti-oxidant power (FRAP) assays. M. rhodantha was the best source of antioxidants. Mammillaria sp. showed moderate anti-bacterial effects against bacteria and the highest effects were found using the extracts of M. rhodantha, M. spinosissima, M. crucigera and M. muehlenpfordtii against most bacteria. The anti-bacterial activities were attributed to other phenolic compounds (e.g., chlorogenic acid) than gentisic acid, which was not active against most bacteria. Mammillaria sp. could be considered to be an important natural source of phenolic acids with anti-cancer, anti-bacterial, and anti-oxidant activities.

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Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): a comparative study

Journal of Basic and Clinical Physiology and Pharmacology ◽

10.1515/jbcpp-2013-0141 ◽

2015 ◽

Vol 26 (2) ◽

Cited By ~ 98

Author(s):

Ganiyu Oboh ◽

Odunayo M. Agunloye ◽

Stephen A. Adefegha ◽

Ayodele J. Akinyemi ◽

Adedayo O. Ademiluyi

Keyword(s):

Type 2 Diabetes ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Quinic Acid ◽

Inhibitory Effect ◽

Dependent Manner ◽

Key Enzymes

AbstractChlorogenic acid is a major phenolic compound that forms a substantial part of plant foods and is an ester of caffeic acid and quinic acid. However, the effect of the structures of both chlorogenic and caffeic acids on their antioxidant and antidiabetic potentials have not been fully understood. Thus, this study sought to investigate and compare the interaction of caffeic acid and chlorogenic acid with α-amylase and α-glucosidase (key enzymes linked to type 2 diabetes) activities in vitro.The inhibitory effect of the phenolic acids on α-amylase and α-glucosidase activities was evaluated. Thereafter, their antioxidant activities as typified by their 1,1-diphenyl-2 picrylhydrazyl radical scavenging ability and ferric reducing antioxidant properties were determined.The results revealed that both phenolic acids inhibited α-amylase and α-glucosidase activities in a dose-dependent manner (2–8 μg/mL). However, caffeic acid had a significantly (p<0.05) higher inhibitory effect on α-amylase [ICThe esterification of caffeic acid with quinic acid, producing chlorogenic acid, reduces their ability to inhibit α-amylase and α-glucosidase activities. Thus, the inhibition of α-amylase and α-glucosidase activities by the phenolic acids could be part of the possible mechanism by which the phenolic acids exert their antidiabetic effects.

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Artificial Neural Network Modeling To Predict And Optimize Phenolic Acids Production From Callus Culture of Lactuca Undulata

10.21203/rs.3.rs-750673/v1 ◽

2021 ◽

Author(s):

Rezvan Ramezannejad ◽

Morteza Mofid Bojnoordi ◽

Mohammad Armin ◽

Mahnaz Aghdasi

Keyword(s):

Neural Network ◽

Artificial Neural Network ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Callus Culture ◽

Phenolic Acids ◽

Activation Function ◽

Cichoric Acid ◽

Ann Model ◽

Feed Forward

Abstract The present study aims to model and optimize phenolic acids productions from Lactuca undulate root and leaf-derived callus using the feed-forward Artificial Neural Network (ANN) model. For this purpose, the effect of different concentrations (0, 0.1, 0.5, 1, and 2 mg/l) of Kin in combinations with or without 2,4-D and/or NAA was investigated on callus induction and phenolic acids production. A multi-layer perceptron ANN was applied to correlate the output parameters (cichoric acid, chlorogenic acid and caffeic acid contents) to input (Kin, 2,4-D and NAA) training parameters. A single hidden layer with 5, 10, 15, 20, 25, 30, 35 and 40 neurons was used to optimize ANN architecture. Sum squared error (SSE), Relative Error (RE) and correlation factor (R2) were applied to identify the performance of ANN models. According to the obtained data, the feed-forward neural network with tangent-sigmoid (3-30-1), tangent-tangent (3-15-1) and tangent-tangent (3-35-1) activation function was found as the best model to predict cichoric acid, chlorogenic acid and caffeic acid production from leaf-derived callus, respectively. Meanwhile, ANN with activation function of tangent-tangent (3-20-1), tangent-tangent (3-25-1) and sigmoid-sigmoid (3-20-1) were the most effective models to predict the amount of cichoric acid, chlorogenic acid and caffeic acid from root-derived callus, respectively. In the current study, there was a strong correlation between experimental and predicted data. These results demonstrated that the selected ANN model could predict the effects of plant growth regulators on phenolic acids production using callus culture method.

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Nutrient Solution Concentration Affects Growth, Mineral Composition, Phenolic Acids, and Flavonoids in Leaves of Artichoke and Cardoon

HortScience ◽

10.21273/hortsci.47.10.1424 ◽

2012 ◽

Vol 47 (10) ◽

pp. 1424-1429 ◽

Cited By ~ 30

Author(s):

Youssef Rouphael ◽

Mariateresa Cardarelli ◽

Luigi Lucini ◽

Elvira Rea ◽

Giuseppe Colla

Keyword(s):

Chlorogenic Acid ◽

Caffeic Acid ◽

Mineral Composition ◽

Biomass Production ◽

Phenolic Acids ◽

Nutrient Solution ◽

Solution Concentration ◽

Leaf Number ◽

Total Polyphenols ◽

Leaf Quality

A greenhouse experiment was conducted in Summer and Fall 2011 at the experimental farm of Tuscia University, central Italy, to study the effect of nutrient solution concentration (4, 20, 36, 52, or 68 mequiv·L−1) on biomass production, mineral composition, and concentrations of the major polyphenols in ‘Romolo’ artichoke and ‘Bianco Avorio’ cardoon grown in a floating system. Leaf dry biomass, leaf number, and macroelement concentrations (nitrogen, potassium, calcium, and magnesium) of artichoke and cardoon increased in response to an increase in the nutrient solution concentration, whereas an opposite trend was observed for the total polyphenols, phenolic acids (chlorogenic acid, cynarin, and caffeic acid), and the flavonoid luteolin. Artichoke and cardoon gave maximum biomass production and leaf number at 45 and 54 mequiv·L−1, respectively. Cardoon showed higher biomass and leaf number (average 1.13 kg·m−2 and 14.0 n./plant, respectively) than those observed in artichoke (average 1.07 kg·m−2 and 12.7 n./plant, respectively). The chlorogenic acid, cynarin, caffeic acid, and luteolin concentrations were higher by 204%, 462%, 580%, and 445% in cardoon leaf tissue than in that of artichoke. An improvement of leaf quality (total polyphenols, phenolic acids, and flavonoids) was obtained at the expense of leaf yield through the use of lower fertilizer concentrations in the nutrient solution.

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