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1.
Pak J Pharm Sci ; 37(1(Special)): 205-213, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38747271

ABSTRACT

In this study, a sensitive high-performance liquid chromatography detector was established and validated for the simultaneous determination of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone in Liuwei Muxiang Capsules. The analysis was achieved on CHANIN 100-5-C18-H column (5Āµm, 250 mmƗ4.6 mm) with the temperature of 30oC. Gradient elution was applied using 0.1% phosphoric acid solution-methanol-acetonitrile (50:50) as mobile phase at the flow rate of 1.0 mL/min. The determination was performed at the wavelength of 225 nm (detecting geniposide), 254 nm (detecting ellagic acid), 343 nm (detecting piperine) and 225 nm (detecting costunolide and dehydrocostuslactone) along with the sample volume of 10ĀµL. The linear ranges of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone demonstrated good linear relationships within their respective determination ranges. The average recoveries were 100.04%, 99.86%, 99.79%, 100.17% and 100.41%, respectively. RSD% was 1.3%, 1.2%, 1.2%, 1.2%, 1.5%, respectively. The developed method was proved to be simple, accurate and sensitive, which can provide a quantitative analysis method for the content determination of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone in Liuwei Muxiang capsules.


Subject(s)
Alkaloids , Benzodioxoles , Capsules , Drugs, Chinese Herbal , Ellagic Acid , Iridoids , Lactones , Piperidines , Polyunsaturated Alkamides , Chromatography, High Pressure Liquid/methods , Benzodioxoles/analysis , Polyunsaturated Alkamides/analysis , Piperidines/analysis , Piperidines/chemistry , Alkaloids/analysis , Lactones/analysis , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/analysis , Iridoids/analysis , Ellagic Acid/analysis , Reproducibility of Results , Sesquiterpenes/analysis
2.
Biomed Chromatogr ; 37(9): e5662, 2023 Sep.
Article in English | MEDLINE | ID: mdl-37185963

ABSTRACT

Ellagic acid is one of the most representative natural antioxidants, and is rich in pomegranate peel. In this study, a consecutive countercurrent chromatographic (CCC) separation method was established to improve the preparative efficiency of ellagic acid from pomegranate peel. By optimizing the solvent system, sample size and flow rate, 280 mg of ellagic acid was obtained from 5Ā g of crude sample from pomegranate peel by CCC after six consecutive injections. Moreover, the values of EC50 for ellagic acid in scavenging ABTSĀ·+ and DPPHĀ· were 4.59 Ā± 0.07 and 10.54 Ā± 0.07 Āµg/ml, respectively, indicating a strong antioxidant activity. This study not only established a high-throughput method for the preparation of ellagic acid, but also provided a successful example for the development of and research on other natural antioxidants.


Subject(s)
Lythraceae , Pomegranate , Antioxidants/analysis , Ellagic Acid/analysis , Ellagic Acid/chemistry , Lythraceae/chemistry , Plant Extracts/chemistry
3.
Molecules ; 28(12)2023 Jun 20.
Article in English | MEDLINE | ID: mdl-37375425

ABSTRACT

Red raspberries, which contain a variety of nutrients and phytochemicals that are beneficial for human health, can be utilized as a raw material in the creation of several supplements. This research suggests micronized powder of raspberry pomace production. The molecular characteristics (FTIR), sugar, and biological potential (phenolic compounds and antioxidant activity) of micronized raspberry powders were investigated. FTIR spectroscopy results revealed spectral changes in the ranges with maxima at ~1720, 1635, and 1326, as well as intensity changes in practically the entire spectral range analyzed. The discrepancies clearly indicate that the micronization of the raspberry byproduct samples cleaved the intramolecular hydrogen bonds in the polysaccharides present in the samples, thus increasing the respective content of simple saccharides. In comparison to the control powders, more glucose and fructose were recovered from the micronized samples of the raspberry powders. The study's micronized powders were found to contain nine different types of phenolic compounds, including rutin, elagic acid derivatives, cyanidin-3-sophoroside, cyanidin-3-(2-glucosylrutinoside), cyanidin-3-rutinoside, pelargonidin-3-rutinoside, and elagic acid derivatives. Significantly higher concentrations of ellagic acid and ellagic acid derivatives and rutin were found in the micronized samples than in the control sample. The antioxidant potential assessed by ABTS and FRAP significantly increased following the micronization procedure.


Subject(s)
Rubus , Humans , Rubus/chemistry , Powders/analysis , Ellagic Acid/analysis , Fruit/chemistry , Antioxidants/pharmacology , Antioxidants/analysis , Phenols/analysis , Rutin/analysis
4.
Nutr Neurosci ; 25(10): 2149-2166, 2022 Oct.
Article in English | MEDLINE | ID: mdl-34369317

ABSTRACT

Objectives: We aimed to investigate the protective potential of Punica granatum L. fruit rind extract (PFE) containing punicalagin (10.3% W/W), ellagic acid (EA) (2.7%W/W) in vincristine (75 Āµg/kg i.p.)- induced neuropathic pain in Wistar rats.Methods: Docking simulation studies were done on the three-dimensional (3D) structure of the GABAA and PPAR ƎĀ³ receptor for the binding of EA as well as punicalagin docking studies on TNF-α, and IL-6. The Present Study conceptualized a test battery to evaluate the behavioral, biochemical and histological changes.Results: Vincristine -induced significant cold allodynia, mechanical hyperalgesia, and functional deficit on 12th and 21st days. It also increased in the levels of TNF-α (Tumor necrosis factor-α), IL-6 (Interleukin-6), and MPO (Myeloperoxidase). Administration of PFE (100 and 300 mg/kg, p.o.), EA (50 mg/kg), and gabapentin (100 mg/kg) attenuated Vincristine-induced behavioral and biochemical changes significantly (P < .05). PFE showed better antinociceptive activity to EA. The histopathological evaluation also revealed the protective effects of PFE. Pretreatment of bicuculline (selective antagonist of GABAA receptors) reversed antinociceptive action of PFE, but administration of ƎĀ³ aminobutyric acid potentiated the action of PFE. PPAR-ƎĀ³ antagonist BADGE did not modify the effect of PFE. Docking results revealed that EA properly positioned into GABA and PPARƎĀ³ binding site and acts as a partial agonist. Docking score of Punicalagin found to be - 9.02 kcal/mol and - 8.32 kcal/mol on IL-6 and TNFα respectively.Discussion: Conclusively, the attenuating effect of PFE may be attributed to the GABAergic system, cytokine inhibition, and anti-inflammatory activities.


Subject(s)
Lythraceae , Neuralgia , Pomegranate , Analgesics , Animals , Anti-Inflammatory Agents/pharmacology , Bicuculline/analysis , Bicuculline/therapeutic use , Cytokines , Ellagic Acid/analysis , Ellagic Acid/pharmacology , Ellagic Acid/therapeutic use , Fruit/chemistry , Gabapentin/analysis , Gabapentin/therapeutic use , Hydrolyzable Tannins , Interleukin-6/analysis , Lythraceae/chemistry , Neuralgia/chemically induced , Neuralgia/drug therapy , Neuralgia/prevention & control , PPAR gamma , Peroxidase/analysis , Peroxidase/therapeutic use , Plant Extracts , Rats , Rats, Wistar , Tumor Necrosis Factor-alpha/analysis , Vincristine/toxicity
5.
Molecules ; 27(7)2022 Mar 26.
Article in English | MEDLINE | ID: mdl-35408544

ABSTRACT

Industrial processing of raspberry juice and wine generates considerable byproducts of raspberry pomace. Ellagic acids/ellagitannins, being characterized by their antioxidant and antiproliferation properties, constitute the majority of polyphenolics in the pomace and are valuable for recovery. In the present study, we developed a novel procedure with sodium bicarbonate assisted extraction (SBAE) to recover ellagic acid from raspberry wine pomace. Key parameters in the procedure, i.e., sodium bicarbonate concentration, temperature, time and solid/liquid (S/L) ratio, were investigated by single factor analysis and optimized subsequently by Response Surface Methodology (RSM). Optimal parameters for the SBAE method here were found to be 1.2% (w/v) NaHCO3, 1:93 (w/v) S/L ratio, 22 min and 100 Ā°C. Under these conditions, the ellagic acid yield was 6.30 Ā± 0.92 mg/g pomace with an antioxidant activity of 79.0 Ā± 0.96 Āµmol Trolox eq/g pomace (DPPH assay), which are 2.37 and 1.32 times the values obtained by extraction with methanol-acetone-water solvent, respectively. The considerable improvement in ellagic acid extraction efficiency could be highly attributed to the reactions of lipid saponification and ellagitannin hydrolysis resulted from sodium bicarbonates. The present study has established an organic solvent-free method for the extraction of ellagic acid from raspberry wine pomace, which is feasible and practical in nutraceutical applications.


Subject(s)
Rubus , Wine , Antioxidants/analysis , Ellagic Acid/analysis , Rubus/chemistry , Sodium Bicarbonate , Solvents/analysis , Wine/analysis
6.
Molecules ; 27(20)2022 Oct 14.
Article in English | MEDLINE | ID: mdl-36296486

ABSTRACT

Alzheimer's disease is the most common neurodegenerative disease, characterized by memory loss and cognitive dysfunction. Raspberry fruits contain polyphenols which have antioxidant and anti-inflammatory properties. In this study, we used molecular imprinting technology to efficiently isolate phenolic components from the raspberry ethyl acetate extracts. Six phenolic components (ellagic acid, tiliroside, kaempferol-3-o-rutoside, gallic acid, ferulic acid and vanillic acid) were identified by UPLC-Q-TOF-MS analysis. Molecular docking was used to predict the anti-inflammatory effects and anti-Alzheimer's potential of these isolated compounds, which showed a good binding ability to diseases and related proteins. However, the binding energy and docking fraction of ellagic acid, tiliroside, and kaempferol-3-o-rutoside were better than those of gallic acid, ferulic acid and vanillic acid. Additionally, by studying the effects of these six phenolic components on the LPS-induced secretion of inflammatory mediators in murine microglial (BV2) cells, it was further demonstrated that they were all capable of inhibiting the secretion of NO, IL-6, TNF-α, and IL-1Ɵ to a certain extent. However, ellagic acid, tiliroside, and kaempferol-3-o-rutoside have better inhibitory effects compared to others. The results obtained suggest that the phenolic components extracted from ethyl acetate extracts of raspberry by molecularly imprinted polymers have the potential to inhibit the progression of Alzheimer's disease.


Subject(s)
Molecular Imprinting , Neurodegenerative Diseases , Rubus , Mice , Animals , Rubus/chemistry , Antioxidants/chemistry , Kaempferols/pharmacology , Ellagic Acid/pharmacology , Ellagic Acid/analysis , Molecular Docking Simulation , Tumor Necrosis Factor-alpha , Vanillic Acid/pharmacology , Molecularly Imprinted Polymers , Interleukin-6 , Lipopolysaccharides , Plant Extracts/chemistry , Anti-Inflammatory Agents/pharmacology , Gallic Acid/pharmacology , Rutin , Inflammation Mediators
7.
J Sci Food Agric ; 102(13): 5891-5902, 2022 Oct.
Article in English | MEDLINE | ID: mdl-35437748

ABSTRACT

BACKGROUND: The different parts of pomegranate fruit are considered a powerful mixture of bioactive compounds yet the peels and pulps of the fruits are usually discarded and considered as industrial waste. In this work, ultra-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-QqQ-MS) was utilized for metabolomics analysis of different parts (peel, pulp, seed and juice) of pomegranate fruit cultivars to verify possible variations among the fruits and their waste products as potential sources of functional constituents. RESULTS: Orthogonal projection to latent structure-discriminant analysis (OPLS-DA) coefficient-plot showed enrichment of phenolic compounds such as punicalagin and ellagic acid derivatives in pulp samples while seeds class was enriched in phlorizin, catechin and quercetin, juice class showed abundance of naringenin and pelargonidin-3-pentoside while peels were enriched in anthocyanins and flavonoids including cyanidin diglycoside, quercetin and luteolin glycosides. Although the juice samples of almost all tested cultivars showed remarkable cytotoxic activity, the pulp samples, particularly the Manfalouti cultivar, exhibited the most potent [half maximal inhibitory concentration (IC50 )Ā = 2.367 Ā± 0.14 Āµg/mL in MCF-7, IC50 Ā = 3.854 Ā± 0.23 Āµg/mL in Hep-G2 cell lines]. OPLS models were constructed for determination of cytotoxicity-associated metabolites among where the coefficients plots revealed tannins; granatin A, ellagic acid derivatives, punicalagin α and Ɵ, in addition to anthocyanins and phenolic compounds; cyanidin diglycoside, quercetin, phlorizin, 3-O-caffeoylquinic acid, naringenin and liquiritin were more pertinent with cytotoxicity of the different parts of pomegranate fruit. CONCLUSION: The results obtained allow for the full utilization of the resources of pomegranate fruit and its industrial waste as sources of bioactive compounds. Ā© 2022 Society of Chemical Industry.


Subject(s)
Lythraceae , Pomegranate , Anthocyanins/analysis , Ellagic Acid/analysis , Ellagic Acid/pharmacology , Fruit/chemistry , Industrial Waste/analysis , Lythraceae/chemistry , Metabolomics , Phenols/analysis , Phlorhizin/analysis , Quercetin/analysis , Waste Products/analysis
8.
Molecules ; 25(20)2020 Oct 09.
Article in English | MEDLINE | ID: mdl-33050295

ABSTRACT

Flavonols and ellagic acid glycosides are major phenolic compounds in strawberry fruit. They have antioxidant activity, show protective functions against abiotic and biotic stress, and provide health benefits. However, their spatial distribution in ripe fruit has not been understood. Therefore, matrix-assisted laser desorption/ionization (MALDI)-mass spectrometry imaging (MSI) was performed to investigate their distribution in fruit tissues. Using strawberry extract, five flavonols, namely, three kaempferols and two quercetins, and two ellagic acid glycosides, were tentatively identified by MALDI-tandem MS. To investigate the tentatively identified compounds, MALDI-MSI and tandem MS imaging (MS/MSI) analyses were performed. Kaempferol and quercetin glycosides showed similar distribution patterns. They were mainly found in the epidermis, while ellagic acid glycosides were mainly found in the achene and in the bottom area of the receptacle. These results suggested that the difference in distribution pattern between flavonols and ellagic acid glycosides depends on the difference between their aglycones. Seemingly, flavonols play a role in protective functions in the epidermis, while ellagic acid glycosides play a role in the achene and in the bottom side of the receptacle, respectively. These results demonstrated that MALDI-MSI is useful for distribution analysis of flavonols and ellagic acid glycosides in strawberry fruit.


Subject(s)
Ellagic Acid/analysis , Flavonols/analysis , Fragaria/chemistry , Fruit/chemistry , Glycosides/analysis , Mass Spectrometry/methods , Flavonoids/analysis , Kaempferols/analysis , Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
9.
Molecules ; 25(1)2019 Dec 20.
Article in English | MEDLINE | ID: mdl-31877675

ABSTRACT

The aim of the study was to evaluate the influence of variety and the date of harvest of hazelnut seeds on their antioxidant potential and the profile and content of polyphenols and tocopherols. The research material included the hazelnut seeds of six varieties, harvested from July to September at equal 30-day intervals. Hazelnuts were analyzed for total fat content and antioxidant properties, whereby UPLC-PDA-ESI-MS analysis was used to determine the profile and content of polyphenols, and the HPLC method to determine the content of tocopherols. It was found that the content of fat and tocopherols in nuts increased with the ripening of the nuts. The highest fat content was found in walnut seeds of the Katalonski variety (September) and tocopherols in walnut seeds of the Olbrzym z Halle variety (177.67 mg/kg d.m.). In turn, antioxidant properties and total polyphenols content decreased with the later harvest date. The strongest antioxidant potential was found in the case of Cosford nuts harvested in July (66.93 mmol TE/100 g d.m.). These nuts were also characterized by the highest total polyphenol content (1704.9 mg/100 g d.m.). UPLC-MS analysis allowed the identification of 15 polyphenolic compounds such as phenolic acids, catechins and ellagic acid hexoside in nut seeds.


Subject(s)
Antioxidants/analysis , Catechin/analysis , Corylus/chemistry , Polyphenols/analysis , Seeds/chemistry , Tocopherols/analysis , Corylus/growth & development , Ellagic Acid/analysis , Polyphenols/metabolism , Seeds/growth & development , Tocopherols/metabolism
10.
Electrophoresis ; 39(13): 1621-1627, 2018 07.
Article in English | MEDLINE | ID: mdl-29572874

ABSTRACT

Rising interest in ellagic acid (EA) present in functional foods is supported by its antimutagenic, anticarcinogenic, antiviral, antibacterial and antioxidative effects. The present approach presents for the first time the determination of ellagic acid and other phenolics in wines by miniaturized solid phase extraction prior to capillary zone electrophoresis (CZE) with UV. The extraction was performed using a home-made miniaturizedĀ pipette tip column. The procedure allowed a significant reduction in conditioning/sample/washing/elution volumes. The effects of important factors affecting the extraction efficiency as well as electrophoretic performance were investigated to acquire optimum conditions. The analytes were separated within 10 min with a BGE containing 30Ā mmol/LĀ sodium tetraborate 10% v/v MeOH pH 9.10. The optimized method was applied to the determination of ellagic acid in commercial and pilot-scale wines. Indeed, the content of EA was correlated with viticultural parameters such as grape varietal, production area, and aging conditions (oak wood guard and glass bottle ward). In order to validate the results, a comparison between the CZE and HPLC data was made.


Subject(s)
Electrophoresis, Capillary , Ellagic Acid/analysis , Wine/analysis , Chromatography, High Pressure Liquid , Electrophoresis, Capillary/methods , Food Analysis , Food Quality , Vitis/chemistry , Wood
11.
Arch Biochem Biophys ; 651: 43-51, 2018 08 01.
Article in English | MEDLINE | ID: mdl-29802820

ABSTRACT

Raspberries are a rich source of ellagitannins and anthocyanins. The aim of this work was to investigate whether raspberry consumption can improve vascular function and to understand which phenolic metabolites may be responsible for the effects. A 3 arm double-blind randomized controlled crossover human intervention trial was conducted in 10 healthy males. Flow-mediated dilation (FMD) was measured at baseline, 2Ć¢Ā€ĀÆh, and 24Ć¢Ā€ĀÆh post-consumption of 200Ć¢Ā€ĀÆg and 400Ć¢Ā€ĀÆg of red raspberries containing 201 or 403Ć¢Ā€ĀÆmg of total (poly)phenols, or a matched control drink. Raspberry (poly)phenol metabolites were analyzed in plasma and urine by UPLC-QTOF mass spectrometry using authentic standards. Significant improvements in FMD were observed at 2Ć¢Ā€ĀÆh (1.6% (95%CI 1.2, 1.9) and 1.2% (95% CI 0.8, 1.5)) and 24Ć¢Ā€ĀÆh (1.0% (95% CI 0.6, 1.2) and 0.7% (95%CI 0.2, 0.9)) post-consumption of the 200 and 400Ć¢Ā€ĀÆg raspberry drinks as compared to control, respectively. Plasma ellagic acid, urolithin A-3-glucuronide and urolithin A-sulfate correlated with the improvements in FMD at 2 and 24Ć¢Ā€ĀÆh post consumption, respectively. Consumption of dietary achievable amounts of red raspberries acutely improves endothelial function up to 24Ć¢Ā€ĀÆh and ellagitannins may be responsible for the observed effect.


Subject(s)
Arteries/physiology , Coumarins/blood , Endothelium, Vascular/physiology , Fruit and Vegetable Juices , Polyphenols/blood , Rubus/metabolism , Adult , Coumarins/analysis , Coumarins/metabolism , Double-Blind Method , Ellagic Acid/analysis , Ellagic Acid/blood , Ellagic Acid/metabolism , Fruit and Vegetable Juices/analysis , Humans , Male , Polyphenols/analysis , Polyphenols/metabolism , Pulse Wave Analysis , Young Adult
12.
J Sci Food Agric ; 98(9): 3324-3332, 2018 Jul.
Article in English | MEDLINE | ID: mdl-29240238

ABSTRACT

BACKGROUND: Since processing technology and storage may influence the sensory and nutritional value as well as the shelf life of pomegranate juice (PJ), mild technologies based on microfiltration may be a promising alternative to heat treatments for fruit juice preservation. In this study, physicochemical and microbiological properties of raw (RPJ), microfiltered (MPJ) and cloudy pasteurized (PPJ) PJ were compared over a period of 4 weeks. RESULTS: Data demonstrated that microfiltration was comparable to pasteurization in guaranteeing microbiological stability of the juice, avoiding spoilage of the final product. After treatment, PPJ showed the highest amounts of gallic acid (GA) and ellagic acid derivatives (EAs). During storage, the amount of ellagitannins, EAs and GA similarly decreased in all types of juice. Trends towards variations of monomeric anthocyanins in MPJ and variations of polymeric and copigmented anthocyanins in both MPJ and PPJ were found over storage. CONCLUSION: The optimization of pretreatments and filtration parameters can lead to the industrial scale-up of microfiltration technology for the development of high-quality non-heat-treated PJ. Ā© 2017 Society of Chemical Industry.


Subject(s)
Filtration/methods , Food Handling/methods , Fruit and Vegetable Juices/analysis , Lythraceae , Phenols/analysis , Volatile Organic Compounds/analysis , Anthocyanins/analysis , Chemical Phenomena , Ellagic Acid/analysis , Food Microbiology , Food Preservation , Fruit and Vegetable Juices/microbiology , Gallic Acid/analysis , Hot Temperature , Hydrolyzable Tannins/analysis , Nutritive Value , Pasteurization
13.
BMC Complement Altern Med ; 17(1): 47, 2017 Jan 14.
Article in English | MEDLINE | ID: mdl-28088220

ABSTRACT

BACKGROUND: Punica granatum (pomegranate), an edible fruit originating in the Middle East, has been used as a traditional medicine for treatment of pain and inflammatory conditions such as peptic ulcer. The numerous risks associated with nonsteroidal anti-inflammatory drugs (NSAIDs) for treatment of pain and inflammation give rise to using medicinal herbs as alternative therapies. This study aimed to evaluate the anti-inflammatory effect of isolated compounds from the ethyl acetate (EtOAc) fraction of P. granatum by determination of their inhibitory effects on lipopolysaccharide (LPS), stimulated nitric oxide (NO), prostaglandin E2 (PGE-2), interleukin-6 (IL-6) and cyclooxxgenase-2 (COX-2) release from RAW264.7 cells. METHODS: The compounds ellagic acid, gallic acid and punicalagin A&B were isolated from EtOAc by high performance liquid chromatography (HPLC) and further identified by mass spectrometry (MS). The inhibitory effect of ellagic acid, gallic acid and punicalagin A&B were evaluated on the production of LPS-induced NO by Griess reagent, PGE-2 and IL-6 by immunoassay kit and prostaglandin E2 competitive ELISA kit, and COX-2 by Western blotting. RESULTS: Ellagic acid, gallic acid and punicalagin A&B potentially inhibited LPS-induced NO, PGE-2 and IL-6 production. CONCLUSION: The results indicate that ellagic acid, gallic acid and punicalagin may be the compounds responsible for the anti-inflammatory potential of P. granatum.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Ellagic Acid/pharmacology , Gallic Acid/pharmacology , Hydrolyzable Tannins/pharmacology , Lythraceae/chemistry , Plant Extracts/pharmacology , Animals , Anti-Inflammatory Agents/analysis , Anti-Inflammatory Agents/isolation & purification , Dinoprostone/immunology , Ellagic Acid/analysis , Ellagic Acid/isolation & purification , Fruit/chemistry , Gallic Acid/analysis , Gallic Acid/isolation & purification , Hydrolyzable Tannins/analysis , Hydrolyzable Tannins/isolation & purification , Interleukin-6/genetics , Interleukin-6/immunology , Macrophages/drug effects , Macrophages/immunology , Mice , Plant Extracts/analysis , Plant Extracts/isolation & purification , RAW 264.7 Cells
14.
Int J Mol Sci ; 18(3)2017 Mar 14.
Article in English | MEDLINE | ID: mdl-28335440

ABSTRACT

Polyphenol compositions and concentrations in skins and seeds of five muscadine grapes (cv. "Noble", "Alachua", "Carlos", "Fry", and "Granny Val") cultivated in the United States (Tallahassee-Florida, TA-FL) and South China (Nanning-Guangxi, NN-GX and Pu'er-Yunnan, PE-YN) were investigated, using ultra performance liquid chromatography tandem triple quadrupole time-of-flight mass spectrometry (UPLC Triple TOF MS/MS). Fourteen ellagitannins were newly identified in these muscadine grapes. The grapes grown in NN-GX accumulated higher levels of ellagic acid, methyl brevifolin carboxylate, and ellagic acid glucoside in skins, and penta-O-galloyl-glucose in seeds. In PE-YN, more flavonols were detected in skins, and higher contents of flavan-3-ols, ellagic acid, and methyl gallate were identified in seeds. Abundant seed gallic acid and flavonols were found among the grapes grown in TA-FL. Based on principal component analysis (PCA) of 54 evaluation parameters, various cultivars grown in different locations could be grouped together and vice versa for the same cultivar cultivated in different regions. This is the result of the interaction between genotype and environmental conditions, which apparently influences the polyphenol synthesis and accumulation.


Subject(s)
Adaptation, Physiological , Polyphenols/metabolism , Vitis/chemistry , Ellagic Acid/analysis , Ellagic Acid/metabolism , Flavonols/analysis , Flavonols/metabolism , Gallic Acid/analysis , Gallic Acid/metabolism , Genetic Variation , Polyphenols/analysis , Vitis/genetics , Vitis/metabolism
15.
Molecules ; 22(10)2017 Sep 25.
Article in English | MEDLINE | ID: mdl-28946708

ABSTRACT

Having served as a symbolic fruit since ancient times, pomegranate (Punica granatum) has also gained considerable recognition as a functional food in the modern era. A large body of literature has linked pomegranate polyphenols, particularly anthocyanins (ATs) and hydrolyzable tannins (HTs), to the health-promoting activities of pomegranate juice and fruit extracts. However, it remains unclear as to how, and to what extent, the numerous phytochemicals in pomegranate may interact and exert cooperative activities in humans. In this review, we examine the structural and analytical information of the diverse phytochemicals that have been identified in different pomegranate tissues, to establish a knowledge base for characterization of metabolite profiles, discovery of novel phytochemicals, and investigation of phytochemical interactions in pomegranate. We also assess recent findings on the function and molecular mechanism of ATs as well as urolithins, the intestinal microbial derivatives of pomegranate HTs, on human nutrition and health. A better understanding of the structural diversity of pomegranate phytochemicals as well as their bioconversions and bioactivities in humans will facilitate the interrogation of their synergistic/antagonistic interactions and accelerate their applications in dietary-based cancer chemoprevention and treatment in the future.


Subject(s)
Fruit/chemistry , Lythraceae/chemistry , Ellagic Acid/analysis , Hydrolyzable Tannins/analysis , Phytochemicals/analysis , Polyphenols/analysis
16.
J Sci Food Agric ; 97(3): 802-810, 2017 Feb.
Article in English | MEDLINE | ID: mdl-27173758

ABSTRACT

BACKGROUND: Some studies have reported that different parts of the pomegranate fruit, especially the peel, may act as potential antimicrobial agents and thus might be proposed as a safe natural alternative to synthetic antimicrobial agents. The high tannin content, especially punicalagin, found in pomegranate extracts, has been reported as the main compound responsible for such antimicrobial activity. Because the pomegranate peel chemical composition may vary with the type of cultivar (sweet, sour-sweet and sour), pomegranates may also differ with respect to their antimicrobial capacity. RESULTS: The extract from PTO8 pomegranate cultivar peel had the highest antimicrobial activity, as well as the highest punicalagins (α and Ɵ) and ellagic acid concentrations. In the results obtained from both antibacterial and antifungal activity studies, the sour-sweet pomegranate cultivar PTO8 showed the best antimicrobial activity, and the highest ellagic acid concentrations. CONCLUSION: The results of the present study suggest that ellagic acid content has a significant influence on the antimicrobial activity of the pomegranate extracts investigated. The pomegranate peel of the PTO8 cultivar is a good source of antifungal and antibacterial compounds, and may represent an alternative to antimicrobial agents of synthetic origin. Ā© 2016 Society of Chemical Industry.


Subject(s)
Anti-Infective Agents/isolation & purification , Food Preservatives/isolation & purification , Fruit/chemistry , Industrial Waste/analysis , Lythraceae/chemistry , Plant Extracts/isolation & purification , 1-Butanol/chemistry , Anti-Infective Agents/analysis , Anti-Infective Agents/economics , Anti-Infective Agents/metabolism , Ascomycota/growth & development , Ascomycota/metabolism , Crops, Agricultural/chemistry , Crops, Agricultural/growth & development , Crops, Agricultural/metabolism , Ellagic Acid/analysis , Ellagic Acid/chemistry , Ellagic Acid/isolation & purification , Ellagic Acid/metabolism , Food Preservatives/analysis , Food Preservatives/economics , Food Preservatives/metabolism , Food-Processing Industry/economics , Fruit/growth & development , Fruit/metabolism , Gram-Negative Bacteria/growth & development , Gram-Negative Bacteria/metabolism , Gram-Positive Bacteria/growth & development , Gram-Positive Bacteria/metabolism , Hydrolyzable Tannins/analysis , Hydrolyzable Tannins/chemistry , Hydrolyzable Tannins/isolation & purification , Hydrolyzable Tannins/metabolism , Industrial Waste/economics , Lythraceae/growth & development , Lythraceae/metabolism , Methanol/chemistry , Microbial Viability , Mitosporic Fungi/growth & development , Mitosporic Fungi/metabolism , Molecular Structure , Plant Extracts/analysis , Plant Extracts/economics , Plant Extracts/metabolism , Solvents/chemistry , Spain , Species Specificity , Stereoisomerism
17.
Crit Rev Food Sci Nutr ; 56(10): 1753-75, 2016 Jul 26.
Article in English | MEDLINE | ID: mdl-25781639

ABSTRACT

Epidemiological reports as well as experimental studies have demonstrated the significant health benefits provided by regular berry consumption. Berries possess both prophylactic and therapeutic potential against several chronic illnesses, such as cardiovascular, neurodegenerative, and neoplastic diseases. Berries owe their health benefits to phytoconstituents, such as polyphenolic anthocyanins, ellagic acid, and a diverse array of phytochemicals bestowed with potent antioxidant and anti-inflammatory effects as well as the ability to engage a multitude of signaling pathways. This review highlights the principal chemical constituents present in berries and their primary molecular targets. The article presents and critically analyzes the chemopreventive and therapeutic potential of berry extracts, fractions, and bioactive components on various cancers of the gastrointestinal tract (GIT), including esophageal, stomach, intestinal, and colorectal cancers as well as cancers of the upper aerodigestive tract, such as oral cancer. The current status of clinical studies evaluating berry products in several aforementioned cancers is presented. Various emerging issues including dose-ranging and dosage forms, the role of synergy and the usage of combination therapy as well as other relevant areas essential for the development of berry phytoconstituents as mainstream chemopreventive and therapeutic agents against aerodigestive and GIT cancers are critically discussed.


Subject(s)
Anticarcinogenic Agents/analysis , Fruit/chemistry , Gastrointestinal Neoplasms/prevention & control , Plant Extracts/analysis , Animals , Anthocyanins/analysis , Anthocyanins/pharmacology , Anticarcinogenic Agents/pharmacology , Clinical Trials as Topic , Digestion/drug effects , Disease Models, Animal , Ellagic Acid/analysis , Ellagic Acid/pharmacology , Humans , Phytochemicals/analysis , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Polyphenols/analysis , Polyphenols/pharmacology
18.
Phytochem Anal ; 26(5): 353-66, 2015.
Article in English | MEDLINE | ID: mdl-26047031

ABSTRACT

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.


Subject(s)
Plant Preparations/analysis , Potentilla/chemistry , Tannins/analysis , Biflavonoids/analysis , Biflavonoids/chemistry , Catechin/analysis , Catechin/chemistry , Chromatography, High Pressure Liquid , Ellagic Acid/analysis , Ellagic Acid/chemistry , Flavonoids/analysis , Flavonoids/chemistry , Glycosides/analysis , Glycosides/chemistry , Hydrolyzable Tannins/analysis , Hydrolyzable Tannins/chemistry , Magnetic Resonance Spectroscopy/methods , Mass Spectrometry/methods , Molecular Structure , Plant Preparations/chemistry , Plants, Medicinal/chemistry , Polyphenols/chemistry , Proanthocyanidins/analysis , Proanthocyanidins/chemistry , Rhizome/chemistry , Tannins/chemistry
19.
Int J Mol Sci ; 16(7): 14540-53, 2015 Jun 26.
Article in English | MEDLINE | ID: mdl-26132562

ABSTRACT

Twenty three different wild blackberry fruit samples were assessed regarding their phenolic profiles and contents (by LC/MS quadrupole time-of-flight (QTOF) and antioxidant activity (ferric reducing ability of plasma (FRAP) and 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS)) by two different extraction methods. Thirty four phenolic compounds were detected (8 anthocyanins, 15 flavonols, 3 hydroxycinnamic acids, 6 ellagic acid derivatives and 2 flavones). In samples, where pressurized liquid extraction (PLE) was used for extraction, a greater increase in yields of phenolic compounds was observed, especially in ellagic acid derivatives (max. 59%), flavonols (max. 44%) and anthocyanins (max. 29%), than after extraction by the ultrasonic technique extraction (UAE) method. The content of phenolic compounds was significantly correlated with the antioxidant activity of the analyzed samples. Principal component analysis (PCA) revealed that the PLE method was more suitable for the quantitative extraction of flavonols, while the UAE method was for hydroxycinnamic acids.


Subject(s)
Antioxidants/chemistry , Flavonoids/chemistry , Fruit/chemistry , Plant Extracts/chemistry , Rubus/chemistry , Antioxidants/pharmacology , Coumaric Acids/analysis , Ellagic Acid/analysis , Flavonoids/pharmacology , Oxidation-Reduction , Plant Extracts/pharmacology
20.
Plant Foods Hum Nutr ; 70(2): 184-92, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25800644

ABSTRACT

The study investigated the changes in the metabolite, antioxidant and α-glucosidase inhibitory activities of Phyllanthus niruri after three drying treatments: air, freeze and oven dryings. Water extracts and extracts obtained using different solvent ratios of ethanol and methanol (50, 70, 80 and 100%) were compared. The relationships among the antioxidant, α-glucosidase inhibitory activity and metabolite levels of the extracts were evaluated using partial least-square analysis (PLS). The solvent selectivity was assessed based on the phytochemical constituents present in the extract and their concentrations quantitatively analyzed using high performance liquid chromatography. The freeze-dried P. niruri samples that were extracted with the mixture of ethanol or methanol with low ratio of water showed higher biological activity values compared with the other extracts. The PLS results for the ethanolic with different ratio and water extracts demonstrated that phenolic acids (chlorogenic acid and ellagic acid) and flavonoids were highly linked to strong α-glucosidase inhibitory and antioxidant activities.


Subject(s)
Antioxidants/pharmacology , Phyllanthus/chemistry , Plant Extracts/pharmacology , Antioxidants/analysis , Chlorogenic Acid/analysis , Chlorogenic Acid/pharmacology , Chromatography, High Pressure Liquid , Desiccation , Ellagic Acid/analysis , Ellagic Acid/pharmacology , Enzyme Inhibitors/pharmacology , Ethanol/chemistry , Flavonoids/analysis , Flavonoids/pharmacology , Freeze Drying , Hydroxybenzoates/analysis , Hydroxybenzoates/pharmacology , Plant Extracts/analysis , Solvents , Water/chemistry , alpha-Glucosidases/metabolism
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