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1.
Int J Mol Sci ; 24(17)2023 Aug 24.
Artigo em Inglês | MEDLINE | ID: mdl-37685975

RESUMO

Reactive α-dicarbonyls (α-DCs), such as methylglyoxal (MGO), glyoxal (GO), and 3-deoxyglucosone (3-DG), are potent precursors in the formation of advanced glycation end products (AGEs). In particular, MGO and MGO-derived AGEs are thought to be involved in the development of vascular complications in diabetes. Experimental studies showed that citrus and pomegranate polyphenols can scavenge α-DCs. Therefore, the aim of this study was to evaluate the effect of a citrus and pomegranate complex (CPC) on the α-DCs plasma levels in a double-blind, placebo-controlled cross-over trial, where thirty-six elderly subjects were enrolled. They received either 500 mg of Citrus sinensis peel extract and 200 mg of Punica granatum concentrate in CPC capsules or placebo capsules for 4 weeks, with a 4-week washout period in between. For the determination of α-DCs concentrations, liquid chromatography tandem mass spectrometry was used. Following four weeks of CPC supplementation, plasma levels of MGO decreased by 9.8% (-18.7 nmol/L; 95% CI: -36.7, -0.7 nmol/L; p = 0.042). Our findings suggest that CPC supplementation may represent a promising strategy for mitigating the conditions associated with MGO involvement. This study was registered on clinicaltrials.gov as NCT03781999.


Assuntos
Citrus , Punica granatum , Idoso , Humanos , Cápsulas , Produtos Finais de Glicação Avançada , Óxido de Magnésio , Aldeído Pirúvico
2.
Molecules ; 28(6)2023 Mar 22.
Artigo em Inglês | MEDLINE | ID: mdl-36985839

RESUMO

The most significant reactive α-dicarbonyl RCS involved in the pathomechanism of glycation and related diseases is methylglyoxal (MGO). Hyperglycemia promotes the generation of MGO and leads to the formation of advanced glycation end products (AGEs). Therefore, MGO trapping and glycation inhibition appear to be important therapeutic targets in prediabetes, diabetes, and in the early prevention of hyperglycemic complications. Peppermint leaf is commonly used as herbal tea, rich in polyphenols. Eriocitrin, its predominant component, in a double-blind, randomized controlled study reversed the prediabetic condition in patients. However, the antiglycation activity of this plant material and its polyphenols has not been characterized to date. Therefore, the aim of this study was to evaluate the ability of a peppermint leaf dry extract and its polyphenols to inhibit non-enzymatic protein glycation in a model with bovine serum albumin (BSA) and MGO as a glycation agent. Peppermint polyphenols were also evaluated for their potential to trap MGO in vitro, and the resulting adducts were analyzed by UHPLC-ESI-MS. To relate chemical composition to glycation inhibitory activity, the obtained peppermint extract was subjected to qualitative and quantitative analysis. The capability of peppermint leaf polyphenols to inhibit glycation (27.3-77.2%) and form adducts with MGO was confirmed. In the case of flavone aglycones, mono- and di-adducts with MGO were observed, while eriodictyol and eriocitrin effectively produced only mono-adducts. Rosmarinic acid and luteolin-7-O-glycosides did not reveal this action. IC50 of the peppermint leaf dry extract was calculated at 2 mg/mL, equivalent to a concentration of 1.8 µM/mL of polyphenols, including ~1.4 µM/mL of flavonoids and ~0.4 µM/mL of phenolic acids. The contribution of the four major components to the anti-AGE activity of the extract was estimated at 86%, including eriocitrin 35.4%, rosmarinic acid 25.6%, luteolin-7-O-rutinoside 16.9%, luteolin-7-O-ß-glucuronoside 8.1%, and others 14%. The effect of peppermint dry extract and polyphenols in inhibiting MGO-induced glycation in vitro was comparable to that of metformin used as a positive control.


Assuntos
Polifenóis , Aldeído Pirúvico , Humanos , Polifenóis/química , Aldeído Pirúvico/química , Mentha piperita/química , Luteolina/análise , Óxido de Magnésio , Extratos Vegetais/química , Folhas de Planta/química , Produtos Finais de Glicação Avançada/química , Ácido Rosmarínico
3.
Molecules ; 28(23)2023 Nov 24.
Artigo em Inglês | MEDLINE | ID: mdl-38067472

RESUMO

Methylglyoxal (MGO) is the major compound belonging to reactive carbonyl species (RCS) responsible for the generation of advanced glycation end products (AGEs). Its upregulation, followed by deleterious effects at the cellular and systemic levels, is associated with metabolic disturbances (hyperglycemia/hyperinsulinemia/insulin resistance/hyperlipidemia/inflammatory processes/carbonyl stress/oxidative stress/hypoxia). Therefore, it is implicated in a variety of disorders, including metabolic syndrome, diabetes mellitus, and cardiovascular diseases. In this review, an interplay between pathways leading to MGO generation and scavenging is addressed in regard to this system's impairment in pathology. The issues associated with mechanistic MGO involvement in pathological processes, as well as the discussion on its possible causative role in cardiometabolic diseases, are enclosed. Finally, the main strategies aimed at MGO and its AGEs downregulation with respect to cardiometabolic disorders treatment are addressed. Potential glycation inhibitors and MGO scavengers are discussed, as well as the mechanisms of their action.


Assuntos
Doenças Cardiovasculares , Diabetes Mellitus , Hiperglicemia , Humanos , Aldeído Pirúvico/farmacologia , Produtos Finais de Glicação Avançada/metabolismo , Óxido de Magnésio , Doenças Cardiovasculares/tratamento farmacológico , Doenças Cardiovasculares/metabolismo
4.
Int J Mol Sci ; 23(23)2022 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-36499065

RESUMO

The excessive dietary intake of simple sugars and abnormal metabolism in certain diseases contribute to the increased production of α-dicarbonyls (α-DCs), such as methylglyoxal (MGO) and glyoxal (GO), the main precursors of the formation of advanced glycation end products (AGEs). AGEs play a vital role, for example, in the development of cardiovascular diseases and diabetes. Aspalathus linearis (Burman f.) R. Dahlgren (known as rooibos tea) exhibits a wide range of activities beneficial for cardio-metabolic health. Thus, the present study aims to investigate unfermented and fermented rooibos extracts and their constituents for the ability to trap MGO and GO. The individual compounds identified in extracts were tested for the capability to inhibit AGEs (with MGO or GO as a glycation agent). Ultra-high-performance liquid chromatography coupled with an electrospray ionization mass spectrometer (UHPLC-ESI-MS) was used to investigate α-DCs' trapping capacities. To evaluate the antiglycation activity, fluorescence measurement was used. The extract from the unfermented rooibos showed a higher ability to capture MGO/GO and inhibit AGE formation than did the extract from fermented rooibos, and this effect was attributed to a higher content of dihydrochalcones. The compounds detected in the extracts, such as aspalathin, nothofagin, vitexin, isovitexin, and eriodictyol, as well as structurally related phloretin and phloroglucinol (formed by the biotransformation of certain flavonoids), trapped MGO, and some also trapped GO. AGE formation was inhibited the most by isovitexin. However, it was the high content of aspalathin and its higher efficiency than that of metformin that determined the antiglycation and trapping properties of green rooibos. Therefore, A. linearis, in addition to other health benefits, could potentially be used as an α-DC trapping agent and AGE inhibitor.


Assuntos
Aspalathus , Aspalathus/química , Flavonoides/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Produtos Finais de Glicação Avançada
5.
Molecules ; 27(16)2022 Aug 19.
Artigo em Inglês | MEDLINE | ID: mdl-36014531

RESUMO

Strawberry leaves are considered a valuable waste material; so far, mainly due to their antioxidant properties. Since the annual production of this crop is high, our study aimed to thoroughly examine the chemical composition and antidiabetes-related bioactivity of Fragaria × ananassa leaf of its popular and productive cultivar Senga Sengana. Leaves from three different seasons, collected after fruiting, were extensively analyzed (UHPLC-qTOF-MS/MS, HPLC-DAD). Some individual components were isolated and quantified, including specific flavonol diglycosides (e.g., 3-O-[ß-xylosyl(1‴→2″)]-ß-glucuronosides). The separated quercetin glycosides were tested in an antiglycation assay, and their methylglyoxal uptake capacity was measured. In addition, the biodegradable polyester precursor 2-pyrone-4,6-dicarboxylic acid (PDC) was confirmed at relatively high levels, providing further opportunity for strawberry leaf utilization. We want to bring to the attention of the food, pharmaceutical, and cosmetic industries the Senga Sengana strawberry leaf as a new botanical raw material. It is rich in PDC, ellagitannins, and flavonols-potent glycation inhibitors.


Assuntos
Fragaria , Flavonóis/análise , Fragaria/química , Frutas/química , Taninos Hidrolisáveis/análise , Folhas de Planta/química , Pironas , Espectrometria de Massas em Tandem
6.
Molecules ; 28(1)2022 Dec 25.
Artigo em Inglês | MEDLINE | ID: mdl-36615355

RESUMO

Cistus is a plant that has been used in natural medicine for hundreds of years; it works primarily as an antioxidant and cleansing agent. Cistus × incanus leaves or herb can be an attractive source of polyphenols and flavonoids. The official protocols of active compound analysis relies on the extraction of compounds of interest from plant matter, which makes their determination long and costly. An analysis of plant material in its native state can be performed using vibrational spectroscopy. This paper presents a comparison of Raman spectroscopy, attenuated total reflection in mid-infrared and diffuse reflectance technique in the near-infrared region for the simultaneous quantification of total polyphenols (TPC) and flavonoids (TF) content, as well as the determination of FRAP antioxidant activity of C. incanus material. Utilizing vibrational spectra and using partial least squares algorithm, TPC and TF were quantified with the RSEPVAL errors in the 2.7-5.4% range, while FRAP antioxidant activity for validation sets was determined with relative errors ranged from 5.2 to 9.3%. For the analyzed parameters, the lowest errors of predictions were computed for models constructed using Raman data. The developed models allow for fast and precise quantification of the studied active compounds in C. incanus material without any chemical sample treatment.


Assuntos
Cistus , Polifenóis , Polifenóis/química , Flavonoides/química , Cistus/química , Antioxidantes/química , Análise dos Mínimos Quadrados
7.
Molecules ; 27(8)2022 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-35458630

RESUMO

Reactive oxygen and carbonyl species promote oxidative and carbonyl stress, and the development of diabetes, metabolic syndrome, cardiovascular diseases, and others. The traditional herb Cistus × incanus is known for its antioxidant properties; therefore, the current study aimed to assess how the chemical composition of a C. incanus water infusion corresponds with its antioxidative and antiglycative effects in vitro. The composition of infusions prepared from commercial products was analyzed with UHPLC-ESI-qTOF-MS. Total phenolics, flavonoids, and non-flavonoid polyphenols were determined. Antioxidant activity of infusions and selected polyphenols was investigated using DPPH, ABTS, and FRAP. Fluorometric measurements and methylglyoxal capture were performed to investigate the antiglycation activity. PCA and PLS-DA models were applied to explore the correlation between chemical and antioxidant results. The principal flavonoids in C. incanus were flavonols. In vitro tests revealed that a stronger antioxidant effect was demonstrated by plant material from Turkey rich in flavonoids, followed by Albania and Greece. Flavonols and ellagic acid displayed stronger antiradical and reducing power than EA-derived urolithins. Hyperoside was the most potent inhibitor of glycation. The results indicate that flavonoids are primarily responsible for rock rose antioxidant and antiglycation properties. PLS-DA modeling can be used to identify the origin of plant material with sensitivity and specificity exceeding 86%.


Assuntos
Cistus , Antioxidantes/química , Antioxidantes/farmacologia , Cistus/química , Flavonoides/química , Flavonoides/farmacologia , Flavonóis , Fenóis/química , Fenóis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Polifenóis/química , Polifenóis/farmacologia , Água
8.
Molecules ; 27(19)2022 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-36235112

RESUMO

Various mint taxa are widely cultivated and are used not only for medicinal purposes but also in cosmetic and industrial applications. The development of new varieties or cultivars of mint generates difficulties in their correct identification and safe use. Volatile organic compounds (VOCs) from the leaves of seven different taxa of the genus Mentha obtained by hydrodistillation (HD) and headspace solid-phase microextraction (HS-SPME) were analyzed using gas chromatography-mass spectrometry (GC-MS). Principal component analysis (PCA) was also performed. Comparative GC-MS analysis of the obtained extracts showed similarity in the major compounds. PCA data allowed the separation of two groups of chemotypes among the analyzed mints, characterized by the abundance of piperitenone oxide and carvone. Two out of seven analyzed taxa were not previously examined for VOC profile, one was examined only for patent application purposes, and six out of seven were investigated for the first time using the HS-SPME technique. The presented analysis provides new data on the abundance and qualitative characterization of VOCs in the studied mint plants and on the safety of their use, related to the possibility of the presence of potentially toxic components. HS-SPME is a valuable method to extend the characterization of the VOC profile obtained by hydrodistillation.


Assuntos
Mentha , Compostos Orgânicos Voláteis , Cromatografia Gasosa-Espectrometria de Massas/métodos , Óxidos , Microextração em Fase Sólida/métodos , Compostos Orgânicos Voláteis/análise
9.
Int J Mol Sci ; 22(18)2021 Sep 16.
Artigo em Inglês | MEDLINE | ID: mdl-34576189

RESUMO

Reactive carbonyl species (RCS) such as methylglyoxal (MGO) or glyoxal (GO) are the main precursors of the formation of advanced glycation end products (AGEs). AGEs are a major factor in the development of vascular complications in diabetes. Vasoprotectives (VPs) exhibit a wide range of activities beneficial to cardiovascular health. The present study aimed to investigate selected VPs and their structural analogs for their ability to trap MGO/GO, inhibit AGE formation, and evaluate their antioxidant potential. Ultra-high-performance liquid chromatography coupled with an electrospray ionization mass spectrometer (UHPLC-ESI-MS) and diode-array detector (UHPLC-DAD) was used to investigate direct trapping capacity and kinetics of quenching MGO/GO, respectively. Fluorimetric and colorimetric measurements were used to evaluate antiglycation and antioxidant action. All tested substances showed antiglycative effects, but hesperetin was the most effective in RCS scavenging. We demonstrated that rutin, diosmetin, hesperidin, and hesperetin could trap both MGO and GO by forming adducts, whose structures we proposed. MGO-derived AGE formation was inhibited the most by hesperetin, and GO-derived AGEs by diosmetin. High reducing and antiradical activity was confirmed for quercetin, rutin, hesperetin, and calcium dobesilate. Therefore, in addition to other therapeutic applications, some VPs could be potential candidates as antiglycative agents to prevent AGE-related complications of diabetes.


Assuntos
Produtos Finais de Glicação Avançada/metabolismo , Animais , Antioxidantes/metabolismo , Cromatografia Líquida de Alta Pressão , Hesperidina/farmacologia , Humanos , Concentração de Íons de Hidrogênio , Aldeído Pirúvico/farmacologia , Espectrometria de Massas por Ionização por Electrospray
10.
Molecules ; 25(24)2020 Dec 09.
Artigo em Inglês | MEDLINE | ID: mdl-33317096

RESUMO

Galega officinalis L. has been known for centuries as an herbal medicine used to alleviate the symptoms of diabetes, but its comprehensive chemical composition and pharmacological activity are still insufficiently known. The current study involved the qualitative and quantitative phytochemical analysis and in vitro evaluation of the antioxidative and methylglyoxal (MGO) trapping properties of galega herb. Ultra high-performance liquid chromatography coupled with both the electrospray ionization mass spectrometer and diode-array detector (UHPLC-ESI-MS and UHPLC-DAD) were used to investigate the composition and evaluate the anti-MGO capability of extracts and their components. Hot water and aqueous methanol extracts, as well as individual compounds representing phytochemical groups, were also assessed for antioxidant activity using DPPH (2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl) and ABTS (2,2'-azino-bis(3-ethylbenz-thiazoline-6-sulfonic acid) assays. Quercetin and metformin were used as a positive control. We confirmed the presence of tricyclic quinazoline alkaloids, guanidines, flavonoids, and hydroxycinnamic acids (HCAs) in galega extracts. The polyphenolic fraction was dominated by mono-, di-, and triglycosylated flavonols, as well as monocaffeoylhexaric acids. The in vitro tests indicated which G. officinalis components exhibit beneficial antioxidative and MGO trapping effects. For galega extracts, flavonols, and HCAs, a potent antiradical activity was observed. The ability to trap MGO was noted for guanidines and flavonoids, whereas HCA esters and quinazoline alkaloids were ineffective. The formation of mono-MGO adducts of galegine, hydroxygalegine, and rutin in the examined water infusion was observed.


Assuntos
Antioxidantes/química , Galega/química , Compostos Fitoquímicos/química , Alcaloides/química , Antioxidantes/farmacologia , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Guanidinas/química , Hidroxibenzoatos/química , Técnicas In Vitro , Medicina Tradicional , Estrutura Molecular , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Preparações de Plantas/química , Preparações de Plantas/farmacologia , Plantas Medicinais/química , Polifenóis/química , Aldeído Pirúvico/análogos & derivados , Aldeído Pirúvico/química , Quinazolinas/química , Espectrometria de Massas por Ionização por Electrospray
11.
Molecules ; 25(18)2020 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-32917001

RESUMO

Thymol (2-isopropyl-5-methylphenol) belongs to the phenolic monoterpenes and mostly occurs in thyme species. It is one of the main compounds of thyme essential oil. Both thymol and thyme essential oil have long been used in traditional medicine as expectorant, anti-inflammatory, antiviral, antibacterial, and antiseptic agents, mainly in the treatment of the upper respiratory system. The current search for new directions of biological or therapeutic activities of natural plant substances with known structures includes thyme essential oil and thymol. Novel studies have demonstrated their antibiofilm, antifungal, antileishmanial, antiviral, and anticancer properties. Also, their new therapeutic formulations, such as nanocapsules containing these constituents, can be beneficial in medicinal practice and create opportunities for their extensive use. Extensive application of thymol and thyme essential oil in the healthcare sector is very promising but requires further research and analysis.


Assuntos
Óleos Voláteis/química , Timol/química , Thymus (Planta)/química , Animais , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antiparasitários/farmacologia , Antivirais/farmacologia , Apoptose , Biofilmes/efeitos dos fármacos , Proliferação de Células , Cryptococcus/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Monoterpenos/química , Fenóis/química , Extratos Vegetais/farmacologia , Óleos de Plantas/química , Polímeros/química
12.
Molecules ; 25(9)2020 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-32344904

RESUMO

The purpose of this study was to investigate the composition of leaf extracts from Aronia melanocarpa, Chaenomeles superba, and Cornus mas, and their antimicrobial activity against typical spoilage-causing and pathogenic bacteria found in meat and meat products. The highest total phenolic content (TPC) was detected in C. superba extract, followed by C. mas and A. melanocarpa extracts. The antioxidant capacity of the extracts was measured by DPPH and ABTS assays. The lowest IC50 values were found for C. superba extract, followed by C. mas and A. melanocarpa extracts. LC-MS and HPLC analysis revealed that A. melanocarpa and C. superba extracts contained hydroxycinnamic acid derivatives and flavonoids (mainly flavonols). Hydroxycinnamic acid derivatives were detected in the C. mas extract, as well as flavonols, ellagitannins, and iridoids. The antibacterial activity of the plant extracts was tested against Gram-negative bacteria (Moraxella osloensis, Pseudomonas fragi, Acinetobacter baumanii, Escherichia coli, Enterobacter aerogenes, Salmonella enterica) and Gram-positive bacteria (Enterococcus faecium, Staphylococcus aureus, Brochothrix thermosphacta, Lactobacillus sakei, Listeria monocytogenes) using the microculture method. The extracts acted as bacteriostatic agents, decreasing the growth rate (µmax) and extending the lag phase (tlag). C. mas showed most potent antibacterial activity, as confirmed by principal component analysis (PCA).


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Photinia/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Antibacterianos/química , Antioxidantes/química , Relação Dose-Resposta a Droga , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos/química , Extratos Vegetais/química , Polifenóis
13.
Molecules ; 25(20)2020 Oct 12.
Artigo em Inglês | MEDLINE | ID: mdl-33053845

RESUMO

The stone of Cornus mas L. remains the least known morphological part of this plant, whereas the fruit is appreciated for both consumption purposes and biological activity. The stone is considered to be a byproduct of fruit processing and very little is known about its phytochemical composition and biological properties. In this study, the complete qualitative determination of hydrolyzable tannins, their quantitative analysis, total polyphenolic content, and antioxidant properties of the stone of C. mas are presented for the first time. The 37 identified compounds included the following: various gallotannins (11), monomeric ellagitannins (7), dimeric ellagitannins (10), and trimeric ellagitannins (7). The presence of free gallic acid and ellagic acid was also reported. Our results demonstrate that C. mas stone is a source of various bioactive hydrolyzable tannins and shows high antioxidant activity which could allow potential utilization of this raw material for recovery of valuable pharmaceutical or nutraceutical substances. The principal novelty of our findings is that hydrolyzable tannins, unlike other polyphenols, have been earlier omitted in the evaluation of the biological activities of C. mas. Additionally, the potential recovery of these bioactive chemicals from the byproduct is in line with the ideas of green chemistry and sustainable production.


Assuntos
Antioxidantes/química , Taninos Hidrolisáveis/química , Espectrometria de Massas em Tandem
14.
Molecules ; 24(15)2019 Jul 24.
Artigo em Inglês | MEDLINE | ID: mdl-31344905

RESUMO

Hyperglycemia and oxidative stress may be observed in different diseases as important factors connected with their development. They often occur simultaneously and are considered together as one process: Glycoxidation. This can influence the function or structure of many macromolecules, for example albumin, by changing their physiological properties. This disturbs the homeostasis of the organism, so the search for natural compounds able to inhibit the glycoxidation process is a current and important issue. The aim of this study was the examination of the antiglycoxidative capacity of 16 selected phenolic compounds, belonging to three phenolic groups, as potential therapeutic agents. Their antiglycoxidative ability, in two concentrations (2 and 20 µM), were examined by in vitro study. The inhibition of the formation of both glycoxidative products (advanced glycation end products (AGEs) and advanced oxidation protein products (AOPPs)) were assayed. Stronger antiglycoxidative action toward the formation of both AOPPs and AGEs was observed for homoprotocatechuic and ferulic acids in lower concentrations, as well as catechin, quercetin, and 8-O-methylurolithin A in higher concentrations. Homoprotocatechuic acid demonstrated the highest antiglycoxidative capacity in both examined concentrations and amongst all of them. A strong, significant correlation between the percentage of AOPPs and AGEs inhibition by compounds from all phenolic groups, in both examined concentrations, was observed. The obtained results give an insight into the antiglycoxidative potential of phenolic compounds and indicate homoprotocatechuic acid to be the most promising antiglycoxidative agent, but further biological and pharmacological studies are needed.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Fenóis/química , Fenóis/farmacologia , Produtos da Oxidação Avançada de Proteínas/química , Produtos da Oxidação Avançada de Proteínas/farmacologia , Produtos Finais de Glicação Avançada/química , Produtos Finais de Glicação Avançada/farmacologia , Estrutura Molecular , Peso Molecular , Oxirredução , Relação Estrutura-Atividade
15.
Molecules ; 25(1)2019 Dec 24.
Artigo em Inglês | MEDLINE | ID: mdl-31878211

RESUMO

The pharmacological activity of peppermint leaf (Menthae piperitae folium) for medical use is mainly attributed to the presence of essential oil, which, according to the European Pharmacopoeia (Ph. Eur.), should constitute not less than 12 mL/kg of raw material. The content of polyphenols in peppermint-based preparations, except peppermint leaf dry extract, has not yet been considered as an essential parameter in the pharmacopeial assessment of peppermint quality. This study concerns the evaluation of the presence of representatives of polyphenolic compounds in 23 commercial peppermint tinctures (ethanolic extracts) purchased in pharmacies in Poland. The non-volatile polyphenolic fraction was investigated, and the presence of flavonoids and phenolic acids was quantified. High performance liquid chromatography coupled with a diode-array detector (HPLC-DAD) and an electrospray ionization mass spectrometer (U(H)PLC-ESI-MS) were used in the experiment. The study showed that eriocitrin, luteolin-7-O-rutinoside, and rosmarinic acid were the main polyphenolic components of the peppermint tinctures, as previously reported for peppermint leaf. Despite this, the research shows the extremely diverse content of the mentioned compounds in analyzed commercial medicinal products. In light of these results, it seems that the pharmacopeial assessment for the peppermint leaf (Ph. Eur.) and peppermint tincture (Polish Pharmacopoeia (FP)) requires correction and supplementation.


Assuntos
Mentha piperita/química , Plantas Medicinais/química , Polifenóis/análise , Cromatografia Líquida de Alta Pressão , Polifenóis/química , Padrões de Referência , Reprodutibilidade dos Testes
16.
Molecules ; 22(3)2017 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-28273885

RESUMO

Iridoid and polyphenol profiles of 30 different honeysuckle berry cultivars and genotypes were studied. Compounds were identified by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry (UPLC-ESI-qTOF-MS/MS) in positive and negative ion modes and quantified by HPLC-PDA. The 50 identified compounds included 15 iridoids, 6 anthocyanins, 9 flavonols, 2 flavanonols (dihydroflavonols), 5 flavones, 6 flavan-3-ols, and 7 phenolic acids. 8-epi-Loganic acid, pentosyl-loganic acid, taxifolin 7-O-dihexoside, and taxifolin 7-O-hexoside were identified in honeysuckle berries for the first time. Iridoids and anthocyanins were the major groups of bioactive compounds of honeysuckle constituents. The total content of quantified iridoids and anthocyanins was between 128.42 mg/100 g fresh weight (fw) ('Dlinnoplodnaya') and 372 mg/100 g fw ('Kuvshinovidnaya') and between 150.04 mg/100 g fw ('Karina') and 653.95 mg/100 g fw ('Amur'), respectively. Among iridoids, loganic acid was the dominant compound, and it represented between 22% and 73% of the total amount of quantified iridoids in honeysuckle berry. A very strong correlation was observed between the antioxidant potential and the quantity of anthocyanins. High content of iridoids in honeysuckle berries can complement antioxidant properties of phenolic compounds.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Frutas/química , Iridoides/química , Lonicera/química , Fenóis/química , Exsudatos de Plantas/química , Exsudatos de Plantas/farmacologia , Cromatografia Líquida de Alta Pressão , Radicais Livres/antagonistas & inibidores , Compostos Fitoquímicos/química , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
17.
Molecules ; 21(9)2016 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-27598106

RESUMO

Iridoid profiles of honeysuckle berry were studied. Compounds were identified by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry UPLC-ESI-qTOF-MS/MS in positive and negative ions mode. The MS fragmentation pathways of detected iridoid glycosides were also studied in both modes. In the negative ESI mass spectra, iridoids with a methyl ester or lactone structure have preferentially produced adduct [M + HCOOH - H](-) ions. However, protonated ions of molecular fragments, which were released by glycosidic bond cleavage and following fragmentation of aglycone rings, were more usable for iridoid structure analysis. In addition, the neutral losses of H2O, CO, CO2, CH3OH, acetylene, ethenone and cyclopropynone have provided data confirming the presence of functional substituents in the aglycone. Among the 13 iridoids, 11 were identified in honeysuckle berries for the first time: pentosides of loganic acid (two isomers), pentosides of loganin (three isomers), pentosyl sweroside, and additionally 7-epi-loganic acid, 7-epi-loganin, sweroside, secologanin, and secoxyloganin. The five pentoside derivatives of loganic acid and loganin have not been previously detected in the analyzed species. Honeysuckle berries are a source of iridoids with different structures, compounds that are rarely present in fruits.


Assuntos
Frutas/química , Iridoides/química , Lonicera/química
18.
Phytochem Anal ; 26(5): 353-66, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26047031

RESUMO

INTRODUCTION: Potentilla tormentilla has many biological and pharmacological properties and can be used as an ingredient of some herbal medicines or beverages. OBJECTIVE: The aim of this study was to evaluate the content of individual polyphenols, especially condensed and hydrolysable tannins in commercially available tormentil rhizomes and tinctures using chromatographic methods. METHODS: A quantitative analysis (HPLC-PDA) was preceded by qualitative studies (UPLC-qTOF-MS/MS) and the isolation (CC) of the major tannin compounds. RESULTS: The tested plant material is characterised by a high content of tannins and related polyphenols, i.e. in rhizomes even at the level above 20% and in tinctures above 2%. The main components of tormentil rhizomes are procyanidin B3 (mean ~ 3.6%), procyanidin C2 (mean ~ 2.8%), agrimoniin (mean ~ 2.5%), 3-O-galloylquinic acid (mean ~ 1.7%), catechin (mean ~ 1.6%), other flavan-3-ol oligomers (mean ~ 0.5-1.1) and laevigatins (mean ~ 0.2-0.6%). Free ellagic acid and glycosides of ellagic and methylellagic acids are secondary components. CONCLUSIONS: Underground parts of tormentil are a source of oligomeric proanthocyanidins and ellagitannins, but in smaller quantity of gallotannins. Monogalloylquinic acids are new identified compounds, which had not been described in Potentilla tormentilla before we started our research. In the analysed tormentil tinctures agrimoniin concentration is lower in relation to other tannins.


Assuntos
Preparações de Plantas/análise , Potentilla/química , Taninos/análise , Biflavonoides/análise , Biflavonoides/química , Catequina/análise , Catequina/química , Cromatografia Líquida de Alta Pressão , Ácido Elágico/análise , Ácido Elágico/química , Flavonoides/análise , Flavonoides/química , Glicosídeos/análise , Glicosídeos/química , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/química , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos , Estrutura Molecular , Preparações de Plantas/química , Plantas Medicinais/química , Polifenóis/química , Proantocianidinas/análise , Proantocianidinas/química , Rizoma/química , Taninos/química
19.
Plants (Basel) ; 13(3)2024 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-38337895

RESUMO

Thymol, a plant-derived monoterpene phenol known for its broad biological activity, has often been incorporated into chitosan-based biomaterials to enhance therapeutic efficacy. Using the Preferred Reporting Items for Systematic Reviews and Meta-Analysis (PRISMA) guidelines, we conducted a systematic literature review from 2018 to 2023, focusing on the biomedical implications of thymol-loaded chitosan systems. A review of databases, including PubMed, Scopus, and Web of Science was conducted using specific keywords and search criteria. Of the 90 articles, 12 were selected for the review. Thymol-loaded chitosan-based nanogels (TLCBS) showed improved antimicrobial properties, especially against multidrug-resistant bacterial antagonists. Innovations such as bipolymer nanocarriers and thymol impregnated with photosensitive chitosan micelles offer advanced bactericidal strategies and show potential for bone tissue regeneration and wound healing. The incorporation of thymol also improved drug delivery efficiency and biomechanical strength, especially when combined with poly(dimethylsiloxane) in chitosan-gelatin films. Thymol-chitosan combinations have also shown promising applications in oral delivery and periodontal treatment. This review highlights the synergy between thymol and chitosan in these products, which greatly enhances their therapeutic efficacy and highlights the novel use of essential oil components. It also highlights the novelty of the studies conducted, as well as their limitations and possible directions for the development of integrated substances of plant and animal origin in modern and advanced medical applications.

20.
Antioxidants (Basel) ; 12(3)2023 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-36978801

RESUMO

The European Food Safety Authority recommends C. incanus as a natural source of antioxidants. Its activity is essentially determined by polyphenols, although specific compounds are not finally indicated. The available plant material comes from different subspecies and locations, which can lead to differences in chemical composition and potency. For this reason, we conducted a detailed analysis of the polyphenol content and antioxidant activity of 52 different C. incanus teas from Turkey, Albania, Greece, and unspecified regions. We focused special attention on ellagitannins, which have not been properly determined so far. Besides oxidative stress, hyperglycemia is an essential component of cardiometabolic diseases. Therefore, in subsequent experiments, we evaluated the ability of C. incanus extracts and individual polyphenols to inhibit α-glucosidase. Using statistical methods, we analyzed how differences in chemical composition affect activity. The results showed that C. incanus is a rich source of ellagitannins (2.5-19%), which dominate among polyphenols (5.5-23%). Turkish-origin products had higher ellagitannin content and a greater antioxidant effect (FRAP, ABTS) than Albanian and Greek products. In contrast, the flavonoid and phenolic acid contents and DPPH values were at similar levels in all products. An in-depth analysis of their composition indicated that all groups of polyphenols are involved in the antioxidant effect, but a significant contribution can be attributed to ellagitannins and flavonoids. C. incanus extracts showed a high capacity to inhibit α-glucosidase activity (IC50 125-145 µg/mL). Ellagitannins were the most effective inhibitors (IC50 0.7-1.1 µM), with a potency exceeding acarbose (3.3 mM). In conclusion, C. incanus, due to the presence of ellagitannins and flavonoids, exhibits powerful antioxidant and α-glucosidase inhibitory effects.

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