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1.
Molecules ; 29(9)2024 May 05.
Artículo en Inglés | MEDLINE | ID: mdl-38731636

RESUMEN

Plant in vitro cultures can be an effective tool in obtaining desired specialized metabolites. The purpose of this study was to evaluate the effect of light-emitting diodes (LEDs) on phenolic compounds in Rhaponticum carthamoides shoots cultured in vitro. R. carthamoides is an endemic and medicinal plant at risk of extinction due to the massive harvesting of its roots and rhizomes from the natural environment. The shoots were cultured on an agar-solidified and liquid-agitated Murashige and Skoog's medium supplemented with 0.1 mg/L of indole-3-acetic acid (IAA) and 0.5 mg/L of 6-benzyladenine (BA). The effect of the medium and different treatments of LED lights (blue (BL), red (RL), white (WL), and a combination of red and blue (R:BL; 7:3)) on R. carthamoides shoot growth and its biosynthetic potential was observed. Medium type and the duration of LED light exposure did not affect the proliferation rate of shoots, but they altered the shoot morphology and specialized metabolite accumulation. The liquid medium and BL light were the most beneficial for the caffeoylquinic acid derivatives (CQAs) production, shoot growth, and biomass increment. The liquid medium and BL light enhanced the content of the sum of all identified CQAs (6 mg/g DW) about three-fold compared to WL light and control, fluorescent lamps. HPLC-UV analysis confirmed that chlorogenic acid (5-CQA) was the primary compound in shoot extracts regardless of the type of culture and the light conditions (1.19-3.25 mg/g DW), with the highest level under R:BL light. BL and RL lights were equally effective. The abundant component was also 3,5-di-O-caffeoylquinic acid, accompanied by 4,5-di-O-caffeoylquinic acid, a tentatively identified dicaffeoylquinic acid derivative, and a tricaffeoylquinic acid derivative 2, the contents of which depended on the LED light conditions.


Asunto(s)
Flavonoides , Luz , Brotes de la Planta , Ácido Quínico , Brotes de la Planta/crecimiento & desarrollo , Brotes de la Planta/metabolismo , Brotes de la Planta/química , Ácido Quínico/análogos & derivados , Ácido Quínico/metabolismo , Ácido Quínico/química , Flavonoides/metabolismo , Flavonoides/química , Ácidos Indolacéticos/metabolismo
2.
Int J Mol Sci ; 23(22)2022 Nov 10.
Artículo en Inglés | MEDLINE | ID: mdl-36430325

RESUMEN

Rhaponticum carthamoides (Willd.) Iljin is a rare, pharmacopoeial, and medicinal plant, endemic to Siberia and endangered due to the massive collection of raw material from the natural habitat. The aim of the current study was to estimate the effect of sucrose concentration (0-7%) on R. carthamoides transformed root growth and on caffeoylquinic acid derivative (CQA) and flavonoid production. Sucrose in higher concentrations may induce osmotic stress and thus may affect secondary metabolism in plants. It was revealed that sucrose concentration influenced R. carthamoides transformed root biomass and modified the phenolic compound metabolic pathway. However, the dynamics of both processes varied significantly. The optimal sucrose level was different for biomass accumulation and the biosynthesis of specialized metabolite. The highest dry weight of roots was achieved for 7% sucrose (31.17 g L-1 of dry weight), while 1% sucrose was found to be optimal for phenolic acid and flavonoid production. Considering the dry weight increase and metabolite accumulation, 3% sucrose was revealed to give optimal yields of CQAs (511.1 mg L-1) and flavonoids (38.9 mg L-1). Chlorogenic acid, 3,5-, 4,5-di-O-caffeoylquinic acids, 1,4,5-O-tricaffeoylquinic acid, and a tentatively-identified tricaffeoylquinic acid derivative 1 were found to be the most abundant specialized metabolites among the identified CQAs. Our findings indicate that R. carthamoides transformed roots may be an efficient source of CQA derivatives, with valuable health-promoting activities.


Asunto(s)
Leuzea , Biomasa , Sacarosa , Flavonoides , Peso Corporal
3.
Molecules ; 27(20)2022 Oct 20.
Artículo en Inglés | MEDLINE | ID: mdl-36296676

RESUMEN

Cotoneaster species have gained significant importance in traditional Asian medicine for their ability to prevent and treat hyperglycemia and diabetes. Therefore, in this study, some aspects of the beneficial health effects of hydromethanolic extracts of C. bullatus, C. zabelii, and C. integerrimus leaves and fruits were evaluated, including their influence on α-glucosidase, α-amylase, and nonenzymatic protein glycation. The activity was investigated in relation to the polyphenolic profile of the extracts determined by UV-spectrophotometric and HPLC-PDA-fingerprint methods. It was revealed that all leaf and fruit extracts are a promising source of biological components (caffeic acid pseudodepsides, proanthocyanidins, and flavonols), and the leaf extracts of C. bullatus and C. zabelii contain the highest levels of polyphenols (316.3 and 337.6 mg/g in total, respectively). The leaf extracts were also the most effective inhibitors of digestive enzymes and nonenzymatic protein glycation. IC50 values of 8.6, 41.8, and 32.6 µg/mL were obtained for the most active leaf extract of C. bullatus (MBL) in the α-glucosidase, α-amylase, and glycation inhibition tests, respectively. In the kinetic study, MBL was displayed as a mixed-type inhibitor of both enzymes. The correlations between the polyphenol profiles and activity parameters (|r| > 0.72, p < 0.05) indicate a significant contribution of proanthocyanidins to the tested activity. These results support the traditional use of Cotoneaster leaves and fruits in diabetes and suggest their hydrophilic extracts be promising in functional applications.


Asunto(s)
Diabetes Mellitus , Proantocianidinas , Rosaceae , alfa-Amilasas , alfa-Glucosidasas/metabolismo , Frutas/metabolismo , Polifenoles/farmacología , Antioxidantes/farmacología , Extractos Vegetales/farmacología , Rosaceae/metabolismo , Fenoles/farmacología , Hipoglucemiantes/farmacología , Flavonoles , Inhibidores de Glicósido Hidrolasas/farmacología
4.
Molecules ; 27(16)2022 Aug 12.
Artículo en Inglés | MEDLINE | ID: mdl-36014384

RESUMEN

Leaves of Olea europaea are a by-product of the olive oil industry and a dietary supplement with acknowledged antioxidant and anti-inflammatory activity but underestimated photoprotective potential. We investigated the protective effects of the LC-PDA-MS/MS standardized ethanol-water extract of olive leaves (OLE), containing 26.2% total phenols and 22.2% oleuropein, with underlying mechanisms against the UVA-induced oxidative damage in human dermal fibroblasts. Hs68 cells were pre-treated (24 h) with OLE (2.5-25 µg/mL) or the reference antioxidants, quercetin and ascorbic acid (25 µg/mL), followed by irradiation (8 J/cm2). OLE significantly reduced the UVA-induced DNA damage and reactive oxygen species (ROS) overproduction and increased the thioredoxin reductase (TrxR) expression and post-radiation viability of fibroblasts by inhibiting their apoptosis. Both intrinsic and extrinsic apoptotic signaling pathways appeared to be inhibited by OLE, but the activity of caspase 9 was the most reduced. We hypothesized that the TrxR up-regulation by OLE could have prevented the UVA-induced apoptosis of Hs68 cells. In addition, a significant decrease in UVA-induced secretion levels of tumor necrosis factor (TNF-α) and interleukin-2 (IL-2) was shown in human lymphocyte culture in response to OLE treatment. In summary, our results support the beneficial effect of OLE in an in vitro model and indicate its great potential for use in the cosmetic and pharmaceutical industry as a topical photoprotective, antioxidant, and anti-inflammatory agent.


Asunto(s)
Olea , Antioxidantes/farmacología , Fibroblastos , Humanos , Extractos Vegetales/farmacología , Hojas de la Planta , Espectrometría de Masas en Tándem
5.
Antioxidants (Basel) ; 9(10)2020 Oct 16.
Artículo en Inglés | MEDLINE | ID: mdl-33081180

RESUMEN

Traditional herbal medicines have become a subject of global importance with both medical and economic implications. The regular consumption of herbal drugs has led to serious concerns regarding their quality, effectiveness, and safety. Thus, relevant scientific evidence has become an important criterion for the acceptance of traditional health claims. The genus Cotoneaster Medikus provides numerous species traditionally used in Asian medicine for the treatment of haemorrhoids, diabetes, and cardiovascular diseases. This review summarises the achievements of modern research on the Cotoneaster taxa, including ethnobotany, phytochemistry, pharmacology, and toxicology. To date, more than 90 compounds have been isolated or analytically identified in Cotoneaster leaves, fruits, flowers or twigs. These phytochemicals are categorised into flavonoids, procyanidins, phenolic acids, cotonefurans, cyanogenic glycosides, triterpenes, sterols, fatty acids, volatile compounds, and carbohydrates, and many of them are responsible for Cotoneaster pharmacological properties including antioxidant, anti-inflammatory, antimicrobial, antiparasitic, hepatoprotective, anti-diabetic or anti-dyslipidaemic activity. In order to ensure the safety of pharmaceutical applications, the potential toxicity of Cotoneaster extracts has also been investigated. In conclusion, this systematic review provides an important reference base for further study into the various medical applications of both the dry extracts and pure isolates of Cotoneaster species.

6.
Antioxidants (Basel) ; 9(1)2020 Jan 12.
Artículo en Inglés | MEDLINE | ID: mdl-31940952

RESUMEN

Cotoneaster plants are sources of traditional medicines and dietary products, with health benefits resulting from their phenolic contents and antioxidant activity. In this work, active markers of the leaves of C. bullatus and C. zabelii were characterized and evaluated in an integrated phytochemical and biological activity study. Based on UHPLC-PDA-ESI-MS3 analysis, twelve analytes were preselected from the constituents of the hydromethanolic leaf extracts, and two of them-caffeoylmalic acid and quercetin 3--O-ß-d-(2″--O-ß-d-xylopyranosyl)galactopyranoside (QPH)-were isolated for full identification (NMR spectroscopy: 1H, 13C, COSY, HMBC, HMQC). All selected phenolics contributed to the antioxidant activity of the extracts, which was demonstrated in chemical in vitro tests (DPPH, FRAP, and TBARS) and in a biological model of human plasma exposed to oxidative/nitrative stress induced by peroxynitrite. This contribution was partly due to the synergy between individual polyphenols, evidenced by an isobolographic analysis of the interactions of (-)-epicatechin, chlorogenic acid, and QPH as representatives of three classes of Cotoneaster polyphenols. All twelve markers, including also neochlorogenic acid, cryptochlorogenic acid, procyanidin B2, procyanidin C1, rutin, hyperoside, isoquercitrin, and quercitrin, were thus applied as calibration standards, and a fast, accurate, reproducible, and fully validated RP-HPLC-PDA method for quality control and standardization of the target extracts was proposed.

7.
Nat Prod Res ; 33(10): 1535-1540, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-29322829

RESUMEN

Essential oils from flowers and leaves of Grindelia integrifolia DC. were investigated for the first time in terms of chemical composition and antimicrobial activity. The GC-FID/MS analysis allowed for the identification of 58 and 72 volatiles, comprising 92.4 and 90.1% of the oils, respectively. The major components of the flower oil were α-pinene (34.9%) and limonene (13.1%), while myrcene (16.9%), spathulenol (12.3%), ß-eudesmol (11.9%) and limonene (10.1%) dominated among the leaf volatiles. The antimicrobial activity, evaluated against 12 selected bacteria and fungus, was found moderate, with the strongest effect of both oils observed against C. albicans (MIC = MBC: 0.63 and 0.31 mg/mL for flower and leaf oil, respectively).


Asunto(s)
Antiinfecciosos/farmacología , Grindelia/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Monoterpenos Acíclicos , Alquenos/análisis , Antiinfecciosos/química , Bacterias/efectos de los fármacos , Monoterpenos Bicíclicos , Candida albicans/efectos de los fármacos , Evaluación Preclínica de Medicamentos/métodos , Flores/química , Hongos/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Monoterpenos/análisis , Hojas de la Planta/química , Aceites de Plantas/análisis , Aceites de Plantas/química , Aceites de Plantas/farmacología
8.
Oxid Med Cell Longev ; 2018: 3482521, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-30510617

RESUMEN

The work presents the results of an investigation into the molecular background of the activity of Cotoneaster fruits, providing a detailed description of their phytochemical composition and some of the mechanisms of their anti-inflammatory and antioxidant effects. GS-FID-MS and UHPLC-PDA-ESI-MS3 methods were applied to identify the potentially health-beneficial constituents of lipophilic and hydrophilic fractions, leading to the identification of fourteen unsaturated fatty acids (with dominant linoleic acid, 375.4-1690.2 mg/100 g dw), three phytosterols (with dominant ß-sitosterol, 132.2-463.3 mg/100 g), two triterpenoid acids (10.9-54.5 mg/100 g), and twenty-six polyphenols (26.0-43.5 mg GAE/g dw). The most promising polyphenolic fractions exhibited dose-dependent anti-inflammatory activity in in vitro tests of lipoxygenase (IC50 in the range of 7.7-24.9 µg/U) and hyaluronidase (IC50 in the range of 16.4-29.3 µg/U) inhibition. They were also demonstrated to be a source of effective antioxidants, both in in vitro chemical tests (DPPH, FRAP, and TBARS) and in a biological model, in which at in vivo-relevant levels (1-5 µg/mL) they normalized/enhanced the nonenzymatic antioxidant capacity of human plasma and efficiently protected protein and lipid components of plasma against peroxynitrite-induced oxidative/nitrative damage. Moreover, the investigated extracts did not exhibit cytotoxicity towards human PMBCs. Among the nine Cotoneaster species tested, C. hjelmqvistii, C. zabelii, C. splendens, and C. bullatus possess the highest bioactive potential and might be recommended as dietary and functional food products.


Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Frutas/química , Fitoquímicos/metabolismo , Extractos Vegetales/farmacología , Plasma/química , Rosaceae/química , Humanos , Técnicas In Vitro , Plasma/efectos de los fármacos
9.
Molecules ; 23(10)2018 Sep 26.
Artículo en Inglés | MEDLINE | ID: mdl-30261655

RESUMEN

The present study investigated the phenolic profile and biological activity of dry extracts from leaves of C. bullatus, C. zabelii and C. integerrimus-traditional medicinal and dietary plants-and evaluated their potential in adjunctive therapy of cardiovascular diseases. Complementary UHPLC-PDA-ESI-MS³, HPLC-PDA-fingerprint, Folin-Ciocalteu, and n-butanol/HCl assays of the extracts derived by fractionated extraction confirmed that they are rich in structurally diverse polyphenols (47 analytes, content up to 650.8 mg GAE/g dw) with proanthocyanidins (83.3⁻358.2 mg CYE/g) dominating in C. bullatus and C. zabelii, and flavonoids (53.4⁻147.8 mg/g) in C. integerrimus. In chemical in vitro tests of pro-inflammatory enzymes (lipoxygenase, hyaluronidase) inhibition and antioxidant activity (DPPH, FRAP), the extracts effects were dose-, phenolic- and extraction solvent-dependent. The most promising polyphenolic extracts were demonstrated to be effective antioxidants in a biological model of human blood plasma-at in vivo-relevant levels (1⁻5 µg/mL) they normalized/enhanced the non-enzymatic antioxidant capacity of plasma and effectively prevented peroxynitrite-induced oxidative/nitrative damage of plasma proteins and lipids. As demonstrated in cytotoxicity tests, the extracts were safe-they did not affect viability of human peripheral blood mononuclear cells. In conclusion, Cotoneaster leaves may be useful in development of natural-based products, supporting the treatment of oxidative stress/inflammation-related chronic diseases, including cardiovascular disorders.


Asunto(s)
Inhibidores Enzimáticos/farmacología , Inflamación/prevención & control , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/farmacología , Plasma/metabolismo , Polifenoles/farmacología , Rosaceae/química , Antioxidantes/farmacología , Humanos , Hialuronoglucosaminidasa/química , Técnicas In Vitro , Mediadores de Inflamación/metabolismo , Lipooxigenasas/química , Hojas de la Planta/química , Plasma/efectos de los fármacos , Sustancias Protectoras/farmacología
10.
Front Pharmacol ; 9: 401, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29740324

RESUMEN

Aim of the study: Taking into account that overactivated leukocytes are an important factor in the development of many chronic diseases, we investigated the activity of phytochemically characterized (HPLC-DAD-MSn) extracts from forsythia leaves and flowers on the pro- and anti-inflammatory functions of leukocytes (effects on IL-1ß, IL-8, TNF-α, and TGFß release) and their adherence to endothelial cells. Using bio-guided fractionation, we isolated the active compounds and determined their biological activity, and we included the positive control quercetin. Methods: The effect on IL-1ß, TNF-α, IL-8, and TGF-α production by leukocytes was measured by enzyme-linked immunosorbent assay (ELISA). The surface expression of adhesion molecules was analyzed with flow cytometry, and the neutrophil attachment to the endothelial cells was assessed fluorimetrically. The effects on p38MAPK, ERK1/2 and JNK phosphorylation were determined using western blots. Results: Leaf extracts had the effect of decreasing TNF-α production in neutrophils and monocyte/macrophage cells. The bio-guided fractionation led to the isolation of the following lignan aglycones: (+)-pinoresinol, (+)-epipinoresinol, (-)-matairesinol, (+)-phillygenin, and (-)-arctigenin. Only phillygenin was able to stimulate the anti-inflammatory function of macrophages by inducing TGF-ß release and IL-10 receptor surface expression. Arctigenin, phillygenin, and a metabolite produced by the gut microbiota, enterolactone, decreased TNF-α and IL-1ß production and neutrophil adhesion to endothelial cells, probably by attenuating the p38 and ERK kinase pathways. Conclusion:Forsythia x intermedia is a valuable source of active lignans, which may be potential candidates for treating inflammatory diseases that are associated with the excessive production of cytokines such as TNF-α and IL-1ß.

11.
Molecules ; 21(6)2016 May 26.
Artículo en Inglés | MEDLINE | ID: mdl-27240329

RESUMEN

The antioxidant efficiency of 70% aqueous methanolic extracts from the leaves of twelve selected Cotoneaster Medik. species was evaluated using four complementary in vitro tests based on SET- (single electron transfer) and HAT-type (hydrogen atom transfer) mechanisms (DPPH, FRAP, O2(•-) and H2O2 scavenging assays). The samples exhibited the dose-dependent responses in all assays with activity parameters of EC50 = 18.5-34.5 µg/mL for DPPH; 0.9-3.8 mmol Fe(2+)/g for FRAP; SC50 = 27.7-74.8 µg/mL for O2(•-); and SC50 = 29.0-91.3 µg/mL for H2O2. Significant linear correlations (|r| = 0.76-0.97, p < 0.01) between activity parameters and total contents of phenolics (5.2%-15.4% GAE) and proanthocyanidins (2.1%-15.0% CYE), with weak or no effects for chlorogenic acid isomers (0.69%-2.93%) and total flavonoids (0.28%-1.40%) suggested that among the listed polyphenols, proanthocyanidins are the most important determinants of the tested activity. UHPLC-PDA-ESI-QTOF-MS analyses led to detection of 34 polyphenols, of which 10 B-type procyanidins, 5 caffeoylquinic acids and 14 flavonoids were identified. After cluster analysis of the data matrix, the leaves of Cotoneaster zabelii, C. splendens, C. bullatus, C. divaricatus, C. hjelmqvistii and C. lucidus were selected as the most promising sources of natural antioxidants, exhibiting the highest phenolic levels and antioxidant capacities, and therefore the greatest potential for pharmaceutical applications.


Asunto(s)
Antioxidantes/química , Extractos Vegetales/química , Polifenoles/química , Rosaceae/química , Antioxidantes/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Depuradores de Radicales Libres/química , Peróxido de Hidrógeno/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Proantocianidinas/química , Proantocianidinas/aislamiento & purificación , Proantocianidinas/farmacología , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Ácido Quínico/aislamiento & purificación , Ácido Quínico/farmacología
12.
Nat Prod Commun ; 10(3): 483-6, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-25924534

RESUMEN

This study was designed to evaluate the flavonoid, saponin (TSC) and phenolic (TPC) contents and in vitro antioxidant activity of the crude (CME) and dry extracts and fractions of Medicago lupulina L. aerial parts. A validated RP-HPLC method led to quantitation of flavonols (kaempferol, quercetin and myricetin) and flavones (apigenin and luteolin) in the hydrolyzed extract. TSC and TPC were assayed spectrophotometrically at 560 and 760 nm, respectively. The antioxidant activity of the CME and the dry fractions were followed in vitro by DPPH free radical and ferric reducing antioxidant power (FRAP) methods. The flavonoid content of CME was 1.27 mg/g dw. The prevailing flavonoids were luteolin and myricetin, at concentrations of 0.37 and 0.36 mg/g dw, respectively. TSC and TPC were detected in CME at the level of 90.4 mg ESE/g dw, and 12.9 mg GAE/g dw, respectively. In the DPPH and FRAP tests, the CME exhibited antioxidant capacity with TEAA and FRAP values of 45.4 µmol Trolox®/g dw and 0.2 mmol Fe2+/g dw, respectively. The diethyl ether dry fraction was the most valuable one, showing the highest antioxidant activity (TEAA = 726.1 µmol Trolox®/g dw, FRAP = 2349.4 µmol Fe2+/g dw) that was in accordance with its high TPC (162.4 mg/g dw).


Asunto(s)
Flavonoides/química , Medicago/química , Fenoles/química , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Saponinas/química , Antioxidantes/química , Antioxidantes/farmacología
13.
Biomed Res Int ; 2015: 181098, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-25811023

RESUMEN

The aim of the study was to obtain transformed roots of Rhaponticum carthamoides and evaluate their phytochemical profile. Hairy roots were induced from leaf explants by the transformation of Agrobacterium rhizogenes strains A4 and ATCC 15834. The best response (43%) was achieved by infection with A4 strain. The effects of different liquid media (WPM, B5, SH) with full and half-strength concentrations of macro- and micronutrients on biomass accumulation of the best grown hairy root line (RC3) at two different lighting conditions (light or dark) were investigated. The highest biomass (93 g L(-1) of the fresh weight after 35 days) was obtained in WPM medium under periodic light. UPLC-PDA-ESI-MS(3) and HPLC-PDA analyses of 80% aqueous methanol extracts from the obtained hairy roots revealed the presence of eleven caffeoylquinic acids and their derivatives and five flavonoid glycosides. The production of caffeoylquinic acids and their derivatives was elevated in hairy roots grown in the light. Only light-grown hairy roots demonstrated the capability for the biosynthesis of such flavonoid glycosides as quercetagetin, quercetin, luteolin, and patuletin hexosides. Chlorogenic acid, 3,5-di-O-caffeoylquinic acid and a tentatively identified tricaffeoylquinic acid derivative were detected as the major compounds present in the transformed roots.


Asunto(s)
Biomasa , Ácidos Cafeicos/metabolismo , Leuzea/crecimiento & desarrollo , Raíces de Plantas/crecimiento & desarrollo , Técnicas de Cultivo de Tejidos/métodos , Agrobacterium , Cromatografía Líquida de Alta Presión , Medios de Cultivo , ADN de Plantas/aislamiento & purificación , Ecdisterona/metabolismo , Reacción en Cadena de la Polimerasa , Polifenoles/metabolismo , Espectrometría de Masa por Ionización de Electrospray
14.
Molecules ; 19(12): 20498-20520, 2014 Dec 08.
Artículo en Inglés | MEDLINE | ID: mdl-25493634

RESUMEN

Dry leaf extracts of eastern teaberry (Gaultheria procumbens L.) were evaluated as a source of bioactive phytocompounds through systematic activity testing and phytochemical profiling. The antioxidant efficiency was tested using five complementary in vitro models (DPPH; FRAP; linoleic acid (LA) peroxidation assay; O2•- and H2O2 scavenging tests) in parallel with standard antioxidants. The 75% methanol extract and its diethyl ether, ethyl acetate (EAF), n-butanol and water fractions exhibited the dose-dependent responses in all assays, with the highest capacities found for EAF (DPPH EC50 = 2.9 µg/mL; FRAP = 12.8 mmol Fe2+/g; IC50 for LA-peroxidation = 123.9 µg/mL; O2•- SC50 = 3.9 µg/mL; H2O2 SC50 = 7.2 µg/mL). The EAF had also the highest anti-inflammatory activity in the inhibition tests of lipoxygenase and hyaluronidase (60.14% and 21.83% effects, respectively, at the concentration of 100 µg/mL). Activity parameters of the extracts correlated strongly with the levels of total phenolics (72.4-270.7 mg GAE/g), procyanidins, and phenolic acids, whereas for flavonoids only moderate effects were observed. Comprehensive UHPLC-PDA-ESI-MS3 and HPLC-PDA studies led to the identification of 35 polyphenols with a procyanidin A-type trimer, quercetin 3-O-glucuronide, isomers of caffeoylquinic acids, and (‒)-epicatechin being the dominant components. Significant activity levels, high phenolic contents and high extraction yields (39.4%-42.5% DW for defatted and crude methanol extracts, respectively) indicate the value of eastern teaberry leaves as bioactive products.

15.
Nat Prod Commun ; 8(4): 505-8, 2013 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-23738465

RESUMEN

A study of the composition of essential oils from aerial and underground parts of Geum rivale L. and Geum urbanum L. growing in Poland led to the identification of 130 compounds. The main compound of the essential oil from underground parts of G. urbanum was eugenol (69.2%), whereas cis-myrtanal (53.3%) was the major constituent of the essential oil from roots of G. rivale. The essential oils from aerial parts of the plants contained large amounts of aliphatic compounds with (Z)-3-hexenol (38.4%) being the dominant constituent of the essential oil from aerial parts of G. urbanum and 1-octen-3-ol (33.9%) from G. rivale.


Asunto(s)
Geum/química , Aceites Volátiles/análisis , Polonia
16.
Nat Prod Commun ; 8(1): 99-102, 2013 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-23472468

RESUMEN

In order to facilitate the quality control of Trifolium repens flowers and leaves, a RP-HPLC method with UV detection was developed for the simultaneous quantitative determination of flavonols and isoflavones. The total flavonoid and phenolic (TPC) contents were determined spectrophotometrically in a visible part of the light spectrum at 425 and 760 nm, respectively. Additionally, evaluation of the antioxidant properties of the plant materials was performed using the DPPH in vitro test. The results showed that the flowers are the richest source of phenolics ranging from 28.7 to 38.8 mg GAE/g, and flavonoids, calculated for hyperoside, up to 20 mg HP/g, which hydrolyzed mainly to flavonols (the quercetin level greater than 6 mg/g). T. repens is poor in isoflavones; similar quantities ofca. 0.2 mg/g were detected in the flowers and leaves. The flower and leaf extracts showed antioxidant activity towards DPPH with EC50 values ranging from 72.3 to 179.3 microg/mL. Significant linear correlations were found between antioxidant potentials of the studied plant materials and total phenolic and flavonoid contents determined by HPLC and spectrophotometric methods (R2 in the range of 0.97 - 0.99).


Asunto(s)
Depuradores de Radicales Libres/análisis , Fenoles/análisis , Trifolium/química , Flores/química , Hojas de la Planta/química
17.
Nat Prod Res ; 26(21): 2050-4, 2012 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-22117193

RESUMEN

The flowers and leaves of Trifolium repens L. (Fabaceae) were subjected to phytochemical investigation in order to identify their major chemical constituents and to evaluate in vitro antioxidant activity of the isolated compounds against DPPH˙. A total of 12 flavonoids, pterocarpan and methyl caffeate were isolated, then characterised by UV, MS, NMR spectroscopy and identified as quercetin and kaempferol 3-O-(6″-α-rhamnopyranosyl-2″-ß-xylopyranosyl)-ß-galactopyranosides (1, 2), kaempferol 3-O-(2″,6″-α-dirhamnopyranosyl)-ß-galactopyranoside, mauritianin (3), quercetin and kaempferol 3-O-(2″-ß-xylopyranosyl)-ß-galactopyranosides (4, 5), kaempferol and quercetin 3-O-ß-(6″-O-acetyl)-galactopyranosides (6, 7), trifolin (8), hyperoside (9), myricetin 3-O-ß-galactopyranoside (10), quercetin (11), ononin (12), medicarpin 3-O-ß-glucopyranoside (13) and methyl caffeate (14). Mauritianin, ononin, pterocarpan and methyl caffeate have been reported in this plant for the first time. The compounds 4, 7, 9, 10, and 11 were tested for their antioxidant effect against DPPH˙. All studied compounds were found to have potent activity, but the most effective in the test were compounds 9, 10 and 11 (EC(50) values in the range 7.51-9.52 µM).


Asunto(s)
Antioxidantes/farmacología , Flores/química , Fenoles/análisis , Hojas de la Planta/química , Trifolium/química , Antioxidantes/química , Ácidos Cafeicos/química , Ácidos Cafeicos/aislamiento & purificación , Ácidos Cafeicos/farmacología , Galactósidos/química , Galactósidos/farmacología , Glucósidos/química , Glucósidos/farmacología , Isoflavonas/química , Isoflavonas/farmacología , Quempferoles/química , Quempferoles/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fenoles/química , Fenoles/farmacología , Extractos Vegetales/análisis , Extractos Vegetales/química , Plantas Medicinales/química , Pterocarpanos/química , Pterocarpanos/farmacología
18.
Molecules ; 15(12): 8769-83, 2010 Dec 02.
Artículo en Inglés | MEDLINE | ID: mdl-21127463

RESUMEN

In order to find new sources of natural antioxidants, the antioxidant potential of 70% methanolic extracts from the inflorescences and leaves of 16 species from the genus Sorbus s.s. was evaluated using two complementary in vitro test systems: the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging assay and the AAPH [2,2¢-azobis-(2-amidinopropane)dihydrochloride]-induced linoleic acid (LA) peroxidation test. The radical-scavenging capacities of the extracts towards the DPPH radical were in the range of 0.25-0.86 millimolar Trolox® equivalents/g dry weight. They were significantly correlated (r=-0.8089, p<0.001) with the results of the LA-peroxidation test, indicating the Sorbus extracts to be universal antioxidants. Significant linear correlations were also found between the different antioxidant potentials and total phenolic contents as estimated by the Folin-Ciocalteu method and further verified by serial determinations of proanthocyanidins, chlorogenic acid isomers and flavonoids (çrêin the range of 0.71-0.95, p<0.001). Cluster analysis of the data matrix identified the ten samples (inflorescences of S. aucuparia, S. pohuashanensis, S. decora, S. koehneana, S. commixta, S. gracilis, and S. sitchensis, and the leaves of S. wilfordii, S. pogonopetala, and S. gracilis) exhibiting the highest antioxidant activity and total phenolic levels and therefore the greatest potential as effective sources for natural health products.


Asunto(s)
Antioxidantes/química , Extractos Vegetales/química , Hojas de la Planta/química , Sorbus/química , Amidinas/química , Antioxidantes/análisis , Ácido Linoleico/química , Oxidación-Reducción , Extractos Vegetales/análisis , Especificidad de la Especie
19.
Acta Pol Pharm ; 64(3): 241-6, 2007.
Artículo en Inglés | MEDLINE | ID: mdl-17695147

RESUMEN

The qualitative and quantitative determinations of coumarins, phenolic acids and flavonoids in the leaves and underground parts of Scopolia caucasica using paper chromatography and HPLC methods were described. From the leaves of this plant, kaempferol 3-O-(2-glucosyl)-galactoside-7-O-glucoside, kaempferol 3-O-(2-glucosyl)-galactoside and quercetin 3-O-glucoside were isolated and identified by spectroscopic methods (UV, 1H- and 13C-NMR).


Asunto(s)
Cumarinas/aislamiento & purificación , Flavonoides/aislamiento & purificación , Fenoles/aislamiento & purificación , Extractos Vegetales/química , Scopolia/química , Cromatografía Líquida de Alta Presión , Cromatografía en Papel , Flavonoides/química , Fenoles/química , Hojas de la Planta/química , Raíces de Plantas/química , Polifenoles
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