Caffeoylquinic acids: chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity

The Plant Journal, Год журнала: 2021, Номер 107(5), С. 1299 - 1319

Опубликована: Июнь 25, 2021

Caffeoylquinic acids (CQAs) are specialized plant metabolites we encounter in our daily life. Humans consume CQAs mg-to-gram quantities through dietary consumption of products. considered beneficial for human health, mainly due to their anti-inflammatory and antioxidant properties. Recently, new biosynthetic pathways via a peroxidase-type p-coumaric acid 3-hydroxylase enzyme were discovered. More recently, GDSL lipase-like able transform monoCQAs into diCQA was identified Ipomoea batatas. recently linked memory improvement; they seem be strong indirect antioxidants Nrf2 activation. However, there is prevalent confusion the designation nomenclature different CQA isomers. Such inconsistencies critical complicate bioactivity assessment since isomers differ potency. A detailed explanation regarding origin such provided, recommendation unify suggested. Furthermore, studies on bioactivity, plant-based laboratory animal diets contain CQAs, which makes it difficult include proper control groups comparison. Therefore, synthetic diet free advised avoid interferences some may produce even at nanomolar levels. Biotransformation by gut microbiota, discovery enzymatic metabolic pathways, assessment, biological properties with potential drug development areas active, ongoing research. This review focused chemistry, biosynthesis, occurrence, analytical challenges, reported mono-, di-, tri-, tetraCQAs.

Язык: Английский

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A Concise Profile of Gallic Acid—From Its Natural Sources through Biological Properties and Chemical Methods of Determination

Molecules, Год журнала: 2023, Номер 28(3), С. 1186 - 1186

Опубликована: Янв. 25, 2023

Nature is a valuable source of anti-oxidants that have health-promoting effect by inhibiting various undesirable changes leading to cell degradation and, consequently, potential disease ailments. One them gallic acid which has been used as healing agent since ancient times. Currently, due beneficial properties, this compound considered be one the main phenolic acids great importance in numerous industries. It commonly substance protecting against harmful effects UV radiation, an astringent cosmetic preparations, and preservative food products. Therefore, now deemed essential for both human health industry. Increasingly better methods its isolation analysis are being developed, new solutions sought increase production. This review, presenting concise characterization acid, updates knowledge about biological activities determination, including chromatographic non-chromatographic methods.

Язык: Английский

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Research progress on the prevention and treatment of hyperuricemia by medicinal and edible plants and its bioactive components

Frontiers in Nutrition, Год журнала: 2023, Номер 10

Опубликована: Июнь 12, 2023

Hyperuricemia is another common metabolic disease, which considered to be closely related the development of many chronic diseases, in addition "three highs." Currently, although drugs show positive therapeutic effects, they have been shown produce side effects that can damage body. There growing evidence medicinal and edible plants their bioactive components a significant effect on hyperuricemia. In this paper, we review with uric acid-lowering summarize mechanisms different components. Specifically, are divided into five categories: flavonoids, phenolic acids, alkaloids, polysaccharides, saponins. These active substances exhibit by inhibiting acid production, promoting excretion, improving inflammation. Overall, examines potential role as means combating hyperuricemia, hope providing some reference value for treatment

Язык: Английский

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Polyphenols in edible plant leaves: an overview of their occurrence and health properties

Food & Function, Год журнала: 2024, Номер 15(13), С. 6847 - 6882

Опубликована: Янв. 1, 2024

Edible plant leaves (EPLs) constitute a major renewable functional biomass available all year round, providing an essential source of polyphenols in the global diet.

Язык: Английский

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Profiling of Chlorogenic Acids from Bidens pilosa and Differentiation of Closely Related Positional Isomers with the Aid of UHPLC-QTOF-MS/MS-Based In-Source Collision-Induced Dissociation

Metabolites, Год журнала: 2020, Номер 10(5), С. 178 - 178

Опубликована: Апрель 29, 2020

Bidens pilosa is an edible herb from the Asteraceae family which traditionally consumed as a leafy vegetable. B. has many bioactivities owing to its diverse phytochemicals, include aliphatics, terpenoids, tannins, alkaloids, hydroxycinnamic acid (HCA) derivatives and other phenylpropanoids. The later compounds such chlorogenic acids (CGAs), are produced either regio- or geometrical isomers. To profile CGA composition of pilosa, methanol extracts tissues, callus cell suspensions were utilized for liquid chromatography coupled mass spectrometric detection (UHPLC-QTOF-MS/MS). An optimized in-source collision-induced dissociation (ISCID) method capable discriminating between closely related HCA quinic acids, based on MS-based fragmentation patterns, was applied. Careful control collision energies resulted in fragment patterns similar MS2 MS3 fragmentation, obtainable by typical ion trap MSn approach. For first time, ISCID approach shown efficiently discriminate positional isomers containing two different cinnamoyl moieties, mixed di-ester feruloyl-caffeoylquinic (m/z 529) coumaroyl-caffeoylquinic 499). results indicate that tissues cultures contained combined total 30 mono-, di-, tri-substituted with dominating thereof. In addition, tartaric esters, caftaric- chicoric also identified. Profiling revealed these differentially distributed across types culture lines derived leaf stem explants.

Язык: Английский

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Phenolic Acids and Flavonoids in Acetonic Extract from Quince (Cydonia oblonga Mill.): Nutraceuticals with Antioxidant and Anti-Inflammatory Potential

Molecules, Год журнала: 2022, Номер 27(8), С. 2462 - 2462

Опубликована: Апрель 11, 2022

Quince (Cydonia oblonga Mill.) is a potential source of polyphenolic compounds related with beneficial biological processes. In this study polyphenols from quince fruit were extracted aqueous acetone at different ratios. A polyphenol profile was identified and quantified by LC-ESI-QqQ. The antioxidant capacity (ORAC DPPH) anti-inflammatory effect (inhibition COX-2 cyclooxygenase) evaluated in vitro. results indicated an the ratio on extraction compounds. higher yields attained 60–75% acetone. However, extracts obtained 85% promoted effects. Optimal scaling analysis that hydroxycinnamic acids (quinic chlorogenic), hydroxybenzoic (vanillic syringic), flavonoids (quercetin kaempferol), dihydrochalcones (neohesperidin) flavones (acacetin) are to activity quince. While phenolic acids, flavonols (kaempferol-3-O-glucoside rutin) flavanols (epicatechin) generated inhibiting 52.3% enzyme. Therefore, selective mix can reduce oxidative stress or inflammatory This suggests use as natural significant nutraceutical potential.

Язык: Английский

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The Research Progress of Extraction, Purification and Analysis Methods of Phenolic Compounds from Blueberry: A Comprehensive Review

Molecules, Год журнала: 2023, Номер 28(8), С. 3610 - 3610

Опубликована: Апрель 21, 2023

Blueberry is the source of a variety bioactive substances, including phenolic compounds, such as anthocyanins, pterostilbene, acids, etc. Several studies have revealed that polyphenols in blueberry important bioactivities maintaining health, antioxidant and anti-tumor activities, immune regulation, prevention chronic diseases, Therefore, these compounds blueberries been widely used field healthcare, extraction, isolation, purification are prerequisites for their utilization. It imperative to systematically review research progress prospects present blueberries. Herein, latest purification, analysis from reviewed, which can turn provide foundation further usage

Язык: Английский

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Protein–Chlorogenic Acid Interactions: Mechanisms, Characteristics, and Potential Food Applications

Antioxidants, Год журнала: 2024, Номер 13(7), С. 777 - 777

Опубликована: Июнь 27, 2024

The interactions between proteins and chlorogenic acid (CGA) have gained significant attention in recent years, not only as a promising approach to modify the structural techno-functional properties of but also enhance their bioactive potential food systems. These can be divided into covalent (chemical or irreversible) non-covalent (physical reversible) linkages. Mechanistically, CGA forms bonds with nucleophilic amino residues by alkaline, free radical, enzymatic approaches, leading changes protein structure functionality, such solubility, emulsification properties, antioxidant activity. In addition, protein–CGA complexes obtained hydrogen bonds, hydrophobic electrostatic interactions, van der Waals forces, each offering unique advantages outcomes. This review highlights mechanism these importance modifying structural, functional, nutritional, physiological attributes animal- plant-based proteins. Moreover, applications conjugates/complexes are explored various systems, beverages, films coatings, emulsion-based delivery so on. Overall, this literature provides an in-depth overview valuable insights for future research develop novel protein-based non-food products improved nutritional functional characteristics.

Язык: Английский

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Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

Materials, Год журнала: 2020, Номер 13(17), С. 3745 - 3745

Опубликована: Авг. 24, 2020

The structure of the Zn(II) complex 5-caffeoylquinic acid (chlorogenic acid, 5-CQA) and type interaction between cation ligand were studied by means various experimental theoretical methods, i.e., electronic absorption spectroscopy UV/Vis, infrared FT-IR, elemental, thermogravimetric density functional theory (DFT) calculations at B3LYP/6-31G(d) level. DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric reducing antioxidant power), CUPRAC (cupric power) trolox oxidation assays applied in study anti-/pro-oxidant properties 5-CQA 5-CQA. antimicrobial activity these compounds against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Salmonella enteritidis Candida albicans was tested. An effect chelation chlorogenic on activities discussed. Moreover, mechanism basis energy descriptors thermochemical parameters. chlorogenate showed better than commonly natural (L-ascorbic acid) synthetic antioxidants (butylated hydroxyanisol (BHA) butylated hydroxytoluene (BHT)). pro-oxidant higher increased with rise compound concentration coordination strongly affected complex.

Язык: Английский

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Caffeoylquinic Acids, Cytotoxic, Antioxidant, Acetylcholinesterase and Tyrosinase Enzyme Inhibitory Activities of Six Inula Species from Bulgaria

Chemistry & Biodiversity, Год журнала: 2020, Номер 17(4)

Опубликована: Март 18, 2020

Abstract Chlorogenic (5‐CQA), 1,5‐, 3,5‐, 4,5‐ and 3,4‐dicaffeoylquinic (DCQA) acids were identified quantified in the methanol extracts of Inula oculus‐christi L., I. bifrons aschersoniana Janka var. , ensifolia conyza ( Griess .) DC. germanica L. by HPLC analysis. The amount 5‐CQA varied from 5.48 to 28.44 mg/g DE highest content was detected . 1,5‐DCQA (4.05–55.25 DE) most abundant dicaffeoyl ester quinic acid followed 3,5‐DCQA, 4,5‐DCQA 3,4‐DCQA. extract showed total phenolic (119.92±0.95 mg GAE/g exhibited strongest DPPH radical scavenging activity (69.41±0.55 %). found be active sample against ABTS .+ (TEAC 0.257±0.012 mg/mL) best tyrosinase inhibitor. studied demonstrated a low inhibitory effect towards acetylcholinesterase possessed cytotoxicity concentration range 10 300 μg/mL toward non‐cancer (MDCK II) cancer (A 549) cells.

Язык: Английский

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