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1.
J Anim Physiol Anim Nutr (Berl) ; 108(1): 111-125, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37602531

RESUMO

Hydrolysable tannins (HT) show potential as silage additive for autumn herbage silages, high in (rumen degradable) protein, as they may reduce proteolysis. Additionally, they have abilities to form pH-reversible tannin-protein complexes, non-degradable in the rumen but degradable in the abomasum and intestines of ruminants. Therefore they can improve milk N efficiency and shift N excretions from urine to faeces, possibly mitigating the environmental impact of ruminants. In this study, two small bunker silos were filled with autumn grass. One was treated with 20 g/kg DM HT extract (TAN) (TannoSan-L), the other with 8 mg/kg DM inoculant containing lactic acid bacteria (INO) (Bonsilage Fit G). Secondly, micro-silos (2.75 L) were filled with four treatments; (1) grass without additive (CON) (n = 5); (2) TAN (n = 5); (3) INO (n = 5); and (4) TAN + INO (n = 5). The bunker silos were used in a cross-over feeding experiment with periods of 4 weeks involving 22 lactating Holstein cows (average ± SD: 183 ± 36.3 days in milk, 665 ± 71.0 kg body weight, and 33.8 ± 3.91 kg/day milk yield). The HT dose was insufficient to reduce proteolysis or alter chemical composition and nutritional value in the micro- and bunker silages. Including grass silage added with TAN (3.2 g HT/kg DM) in the diet, did not affect feed intake nor fat and protein corrected milk yield in comparison to feeding the grass silage added with INO in a similar diet. The TAN-fed cows had an increased faecal N excretion and decreased apparent total-tract N and organic matter digestibility, but no improvement in the cows' N utilization could be confirmed in milk and blood urea levels. Overall, feeding an autumn grass silage treated with 20 g/kg chestnut HT extract did not affect the performance of dairy cows in comparison to feeding an autumn grass silage treated with a lactic acid bacteria inoculant.


Assuntos
Inoculantes Agrícolas , Lactobacillales , Feminino , Bovinos , Animais , Poaceae/metabolismo , Silagem/análise , Taninos/farmacologia , Lactação , Inoculantes Agrícolas/metabolismo , Fermentação , Ácido Láctico/metabolismo , Digestão , Leite/química , Dieta/veterinária , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/metabolismo , Taninos Hidrolisáveis/farmacologia , Rúmen/metabolismo , Extratos Vegetais/farmacologia , Ruminantes , Valor Nutritivo , Zea mays/metabolismo
2.
J Ethnopharmacol ; 314: 116508, 2023 Oct 05.
Artigo em Inglês | MEDLINE | ID: mdl-37264880

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Cotinus coggygria has a number of applications in traditional medicine most of which are connected with its anti-inflammatory and anti-oxidant properties. Since inflammation and oxidative stress are recognized as triggering factors for cancer, anti-cancer activity has also been documented and the possible mechanisms of this activity are under investigation. Important components of C. coggygria extracts are shown to be hydrolysable gallotannins of which pentagalloyl-O-glucose has been studied in details. This compound inhibits various enzymes including prolyl oligopeptidase which is involved in tumorigenesis and tumour growth. According to our pilot studies, oligo-O-galloylglucoses with more than five galloyl residues are also presented in the herb of Bulgarian origin, but their activities have not been examined. AIM OF THE STUDY: To establish an extraction method by which it is possible to concentrate high molecular hydrolysable gallotannins from dried leaves of Cotinus coggygria and to determine their inhibitory properties towards prolyl oligopeptidase and fibroblast activation protein α. MATERIALS AND METHODS: Dried leaves of C. coggygria were extracted using different solvents in single-phase or biphasic systems under various extraction conditions. Main compounds of the extracts were identified by using high performance liquid chromatography and liquid chromatography - high resolution mass spectrometry. The extracts' inhibitory properties towards prolyl oligopeptidase and fibroblast activation protein α were studied on recombinant human enzymes by enzyme kinetic analyses using a fluorogenic substrate. RESULTS: Ethyl acetate/water (pH 3.0) extraction of dried plant leaves proved to be the most efficient method for isolation of high molecular hydrolysable gallotannins which can be further concentrated by precipitation of dicyclohexylammonium salts in ethyl acetate. The main components of those extracts were oligo-O-galloyl glucoses with more than five gallic acid residues. They were shown to inhibit both enzymes studied but were about 30 times more effective inhibitors of prolyl oligopeptidase. CONCLUSIONS: C. coggygria from Bulgarian origin is shown to possess a substantial quantity of oligo-O-galloyl glucoses with more than five gallic acid residues which has not been described thus far in the same herb from other sources. An extraction method useable for concentrating those compounds is established. They are found to inhibit prolyl oligopeptidase with a very good selectivity to fibroblast activation protein α. The previously described antitumor activity of this plant may be at least in part due to the inhibition of the above enzymes which has been shown to participate in the genesis and development of various types of tumors.


Assuntos
Anacardiaceae , Taninos Hidrolisáveis , Humanos , Taninos Hidrolisáveis/farmacologia , Taninos Hidrolisáveis/análise , Prolina , Peptídeo Hidrolases , Prolil Oligopeptidases , Anacardiaceae/química , Ácido Gálico/análise , Extratos Vegetais/química , Folhas de Planta/química
3.
J Ethnopharmacol ; 309: 116377, 2023 Jun 12.
Artigo em Inglês | MEDLINE | ID: mdl-36907477

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Tea (Camellia sinensis) has been consumed for centuries as traditional medicine for various diseases, including diabetes. The mechanism of action of many traditional medicines, including tea, often requires elucidation. Purple tea is a natural mutant of Camellia sinensis, grown in China and Kenya, and is rich in anthocyanins and ellagitannins. AIM OF THE STUDY: Here we aimed to determine whether commercial green and purple teas are a source of ellagitannins and whether green and purple teas, purple tea ellagitannins and their metabolites urolithins have antidiabetic activity. MATERIALS AND METHODS: Targeted UPLC-MS/MS was employed to quantify the ellagitannins corilagin, strictinin and tellimagrandin I, in commercial teas. The inhibitory effect of commercial green and purple teas and purple tea ellagitannins was evaluated on α-glucosidase and α-amylase. The bioavailable urolithins were then investigated for additional antidiabetic effects, by evaluating their effect on cellular glucose uptake and lipid accumulation. RESULTS: Corilagin, strictinin and tellimagrandin I (ellagitannins) were identified as potent inhibitors of α-amylase and α-glucosidase, with Ki values significantly lower (p < 0.05) than acarbose. Commercial green-purple teas were identified as ellagitannin sources, with especially high concentrations of corilagin. These commercial purple teas, containing ellagitannins, were identified as potent α-glucosidase inhibitors with IC50 values significantly lower (p < 0.05) than green teas and acarbose. Urolithin A and urolithin B were as effective (p> 0.05) as metformin in increasing glucose uptake in adipocytes, muscle cells and hepatocytes. In addition, similar (p > 0.05) to metformin, both urolithin A and urolithin B reduced lipid accumulation in adipocytes and hepatocytes. CONCLUSIONS: This study identified green-purple teas as an affordable widely available natural source with antidiabetic properties. Furthermore, additional antidiabetic effects of purple tea ellagitannins (corilagin, strictinin and tellimagrandin I) and urolithins were identified.


Assuntos
Taninos Hidrolisáveis , Hipoglicemiantes , Chá , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/farmacologia , Hipoglicemiantes/farmacologia , Chá/química
4.
Molecules ; 28(4)2023 Feb 17.
Artigo em Inglês | MEDLINE | ID: mdl-36838920

RESUMO

In the present study, blackberry extract was prepared using a previously optimized solid-liquid extraction method in 70% aqueous acetone aimed at the recovery of its principal phenolics. Subsequently, 0.5 g of freeze-dried extract was subjected to flash chromatography fractionation, which was conducted on a C18 column using a binary solvent system of water and methanol at 10 mL/min. The total phenolic content (TPC), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and ferric reducing antioxidant power (FRAP) activities of the obtained 42 flash fractions were determined, and a strong positive correlation (r ≥ 0.986) was exhibited among them. Furthermore, the graph of the antioxidant indices of the flash fractions resembled the flash chromatogram, suggesting a good correlation among the compounds within the chromatographic peaks and the antioxidant indices. LC-MS/MS identified as many 28 phenolics, including cinnamtannin A2 reported for the first time in blackberries. This study further established the role of dominant anthocyanins (cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside), but uniquely those of ellagitannins and catechins on the antioxidant capacity of blackberries.


Assuntos
Catequina , Rubus , Antocianinas/química , Polifenóis/análise , Catequina/análise , Cromatografia Líquida , Antioxidantes/química , Taninos Hidrolisáveis/análise , Cromatografia Líquida de Alta Pressão , Frutas/química , Espectrometria de Massas em Tandem , Fenóis/química , Extratos Vegetais/química
5.
Adv Colloid Interface Sci ; 311: 102833, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36610103

RESUMO

Pomegranate fruit is getting more attention due to its positive health effects, and pomegranate peel (PP) is its main byproduct. PP has the potential to be converted from environmentally polluting waste to wealth due to its rich phenolic compounds such as ellagitannins, proanthocyanidins, and flavonoids with antioxidant, antimicrobial, and health effects. These phenolics are susceptible to environmental conditions such as heat, light, and pH as well as in vivo conditions of gastrointestinal secretions. Some phenolics of PP, e.g., ellagitannins could interfere with food ingredients and thus reduce their beneficial effects. Also, ellagitannins could form complexes with salivary glycoproteins, then a feeling of astringency taste. In this article, nano-delivery systems such as nanoparticles, nanoemulsions, and vesicular nanocarriers, designed and fabricated for PP bioactive compounds in recent years have been reviewed. Among them, lipid-based nano carriers i.e., solid lipid nanoparticles, nanostructured lipid carriers, and vesicular nanocarriers have low toxicity, large-scale production feasibility, easy synthesis, and high biocompatibility. So, it seems that the extraction and purification of bioactives from pomegranate wastes and nanoencapsulating them with cost effective and generally recognized as safe (GRAS) materials can be a bright prospect in enhancing the quality, safety, shelf life and health benefits of pomegranate products.


Assuntos
Frutas , Punica granatum , Frutas/química , Punica granatum/química , Taninos Hidrolisáveis/análise , Sistemas de Liberação de Fármacos por Nanopartículas , Extratos Vegetais/química , Fenóis , Antioxidantes/farmacologia , Antioxidantes/química , Lipídeos/análise
6.
J Agric Food Chem ; 70(51): 16273-16285, 2022 Dec 28.
Artigo em Inglês | MEDLINE | ID: mdl-36519204

RESUMO

Pomegranate (Punica granatum L.) is a well-known source of bioactive phenolic compounds such as ellagitannins, anthocyanins, and flavanols. Punicalagin, one of the main constituents of pomegranate, needs to be biodegraded by bacteria to yield metabolites of medicinal interest. In this work, we tested 30 lactic acid bacteria (LAB) and their capacity to transform punicalagin from a punicalagin-rich pomegranate extract into smaller bioactive molecules, namely, ellagic acid and urolithins. These were identified and quantified by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS2). Further, we evaluated the molecular mechanism governing this transformation through label-free comparative MS-based proteomics. All tested LAB strains were capable of transforming punicalagin into ellagic acid, while the biosynthesis of urolithins was not observed. Proteomic analysis revealed an increase of generic transglycosylases that might have a hydrolytic role in the target phenolic molecule, coupled with an increase in the quantity of ATP-binding cassette (ABC) transporters, which might play a relevant role in transporting the resulting byproducts in and out of the cell.


Assuntos
Ácido Elágico , Taninos Hidrolisáveis , Taninos Hidrolisáveis/análise , Ácido Elágico/metabolismo , Antocianinas/análise , Proteômica , Fenóis/análise , Extratos Vegetais/química , Bactérias/metabolismo
7.
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
8.
Food Chem ; 395: 133600, 2022 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-35793588

RESUMO

Pomegranate is a fruit-bearing tree. Pomegranate flowers, leaves, bark, fruit juice, peel and seeds were reported to have pharmacological effects. Recently, the researches about phytochemicals, metabolism and pharmacokinetics studies of different parts of pomegranate were carried out. There is a lack of summary on different parts of pomegranate. Furthermore, we were interested in potential correlations and differences on the phytochemicals, metabolism and pharmacokinetics studies between the different parts of pomegranate. This review is aimed to provide a comprehensive overview of reported researches on different parts of pomegranate about phytochemicals, metabolism and pharmacokinetics studies. Besides, we introduced analysis strategies for identifying phytochemicals in foods/plants and metabolites in biosamples using LC-HR MSn techniques. Furthermore, we firstly speculated structures and the maximum number of constitutional isomers of ellagitannins and gallotannins. This review is helpful for further application to discover more active compounds and their metabolites from pomegranate and other plants/foods.


Assuntos
Lythraceae , Punica granatum , Flores/química , Frutas/química , Taninos Hidrolisáveis/análise , Lythraceae/química , Metaboloma , Compostos Fitoquímicos/análise , Casca de Planta/química , Folhas de Planta/química , Sementes/química
9.
Molecules ; 27(8)2022 Apr 14.
Artigo em Inglês | MEDLINE | ID: mdl-35458728

RESUMO

It is well established that C-glucosidic ellagitannins contribute to wine quality, and new forms of ellagitannins have been found recently in cognac eaux-de-vie. The contribution of some ellagitannin-derived spirit compounds to eaux-de-vie taste has been demonstrated recently. However, there is a gap in our knowledge of the content, composition, and evolution of C-glucosidic ellagitannins in this matrix. Indeed, the quantification of these compounds and their evolutionary compounds have never before been researched in cognac eaux-de-vie. Thus, the aim of this study was not only to quantify these compounds, but also to study their kinetics and to observe how they are impacted by barrel toasting. For this purpose, barrels representing eight different toasting levels were used to age the same eau-de-vie during the first 18 months. Ellagitannin quantification was carried out by HPLC-Triple quadrupole. The results showed that the evolutionary trend of the eight ellagitannins is the same for all eight types of barrel toasting. The maximum concentrations of C-glucosidic ellagitannins were found after 3 months of aging (up to 23 mg/L) before decreasing to 18 months (9.7 mg/L), whereas ellagitannin-derived spirit compound concentrations increased throughout aging (up to 130.9 mg/L). In addition, barrel toasting had such an impact on ellagitannin content that barrels could be differentiated according to their levels. Eaux-de-vie in barrels with high toasting were lower in ellagitannins concentrations.


Assuntos
Quercus , Vinho , Glucosídeos , Taninos Hidrolisáveis/análise , Vinho/análise , Madeira/química
10.
Food Chem ; 384: 132307, 2022 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-35413769

RESUMO

Ellagitannins are the main extractible phenolic compounds in oak wood. They can be extracted by eaux-de-vie aging in barrels but rapidly undergo chemical transformations, such as hydrolysis, reduction, oxidation, or even substitution reactions. Given gaps in knowledge about their composition in spirits, the goal of this work was to explore ellagitannin behavior during Cognac eaux-de-vie aging and search for new C-glucosidic ellagitannin-derived compounds. A purification protocol was followed to isolate the new formed compounds. UPLC-UV-Q-ToF and NMR spectroscopy were used to characterize a new C-glucosidic ellagitannin, named brandy tannin B. Two new forms of whiskey tannins were also isolated. The new compound, Brandy tannin B along with ß-1-O-ethylvescalagin and ß-1-O-ethylvescalin, and whiskey tannins were identified and quantified for the first time in Cognac eaux-de-vie. In addition, the organoleptic impact of brandy tannin B was evaluated. This work brings new insights into ellagitannin composition and their contribution to spirit quality.


Assuntos
Quercus , Vinho , Glucosídeos/análise , Taninos Hidrolisáveis/análise , Quercus/química , Taninos/análise , Vinho/análise , Madeira/química
11.
J Agric Food Chem ; 70(41): 13049-13061, 2022 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-35438989

RESUMO

Recent studies highlight the influence that oak ellagitannins can have on wine astringency and color. Direct reactions between flavanols or anthocyanins with vescalagin have been reported to occur, but participation of these compounds in the formation of other types of derivatives has only been suggested but not demonstrated. This study aims at evaluating, in wine-like model systems, the possible different roles of the main oak ellagitannins, castalagin and vescalagin, alone or combined, in the synthesis of vitisin A and in the degradation of malvidin 3-O-glucoside. In the presence of pyruvic acid, the anthocyanin disappeared mainly as a result of the synthesis of vitisin A, whereas in its absence, degradation reactions prevailed. In general, ellagitannins increased the synthesis of vitisin A, decreased the total content of degradation products, and changed the degradation profile, with differences observed between castalagin and vescalagin. The results of the study revealed that the fate of malvidin 3-O-glucoside is conditioned by the presence of ellagitannins.


Assuntos
Quercus , Vinho , Antocianinas/análise , Vinho/análise , Taninos Hidrolisáveis/análise , Ácido Pirúvico , Glucosídeos
12.
Molecules ; 27(5)2022 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-35268692

RESUMO

Rambutan (Nephelium lappaceum L.) is a tropical fruit from Asia which has become the main target of many studies involving polyphenolic analysis. Mexico produces over 8 million tons per year of rambutan, generating a huge amount of agro-industrial waste since only the pulp is used and the peel, which comprises around 45% of the fruit's weight, is left behind. This waste can later be used in the recovery of polyphenolic fractions. In this work, emerging technologies such as microwave, ultrasound, and the hybridization of both were tested in the extraction of phenolic compounds from Mexican rambutan peel. The results show that the hybrid technology extraction yielded the highest polyphenolic content (176.38 mg GAE/g of dry rambutan peel). The HPLC/MS/ESI analysis revealed three majoritarian compounds: geraniin, corilagin, and ellagic acid. These compounds explain the excellent results for the biological assays, namely antioxidant activity evaluated by the DPPH, ABTS, and LOI (Lipid oxidation inhibition) assays that exhibited great antioxidant capacity with IC50 values of 0.098, 0.335, and 0.034 mg/mL respectively, as well as prebiotic activity demonstrated by a µMax (maximum growth) of 0.203 for Lactobacillus paracasei. Lastly, these compounds have shown no hemolytic activity, opening the door for the elaboration of different products in the food, cosmetic, and pharmaceutical industries.


Assuntos
Sapindaceae , Frutas/química , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/farmacologia , México , Micro-Ondas , Extratos Vegetais/química , Sapindaceae/química
13.
Nat Prod Res ; 36(14): 3717-3720, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33397138

RESUMO

Phenolic compounds have attracted a lot of attention due to their benefits to human health. Jabuticaba (Myrciaria sp.) fruit has been described as an excellent source of these compounds, while Jabuticaba leaf, considered as plant residue, has shown functional effects. The present study aimed to characterize the phenolic profile in two different leaves extracts (hydroalcoholic ethanol and butanol) of Myrciaria sp. by UPLC-ESI-QTOF-MSE. A total of 40 phenolic compounds were tentatively identified. Jabuticaba leaf extracts presented a rich and diversified composition of phenolic compounds, especially flavonoids, being ellagic acid, quercetin 3-O-glucoside, gallocatechin, and epigallocatechin the most abundant in butanol extracts. Very distinct phenolic profiles were obtained depending on the the solvent indicating that specific preparations can be obtained from the jabuticaba leaf depending on the desired application. This work emphasized the potential of this residue vegetable to be used as a functional ingredient.


Assuntos
Taninos Hidrolisáveis , Myrtaceae , Antioxidantes/química , Butanóis , Cromatografia Líquida de Alta Pressão , Frutas/química , Humanos , Taninos Hidrolisáveis/análise , Myrtaceae/química , Fenóis/análise , Extratos Vegetais/química
14.
Food Res Int ; 147: 110518, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34399496

RESUMO

Jaboticaba, a popular Brazilian berry, has been studied due to its relevant polyphenol composition, health benefits and potential use for the development of derived food products. Considering that around 200 articles have been published in recent years, this review aims to provide comprehensive and updated information, as well as a critical discussion on: (i) jaboticaba polyphenolic composition and extraction methods for their accurate determination; (ii) jaboticaba polyphenol's metabolism; (iii) biological effects of the fruit and the relationship with its polyphenols and their metabolites; (iv) challenges in the development of jaboticaba derived products. The determination of jaboticaba polyphenols should employ hydrolysis procedures during extraction, followed by liquid chromatographic analysis. Jaboticaba polyphenols, mainly anthocyanins and ellagitannins, are extensively metabolized, and their metabolites are probably the most important contributors to the relevant health effects associated with the fruit, such as antioxidant, anti-inflammatory, antidiabetic, hepatoprotective and hypolipidemic. Most of the technological processing of jaboticaba fruit and its residues is related to their application as a colorant, antioxidant, antimicrobial and source of polyphenols. The scientific literature still lacks studies on the metabolism and bioactivity of polyphenols from jaboticaba in humans, as well as the effect of technological processes on these issues.


Assuntos
Myrtaceae , Polifenóis , Antocianinas , Frutas/química , Humanos , Taninos Hidrolisáveis/análise , Polifenóis/análise
15.
PLoS One ; 16(8): e0255831, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34375350

RESUMO

Immature fruits from Punica granatum L. thinning are a neglected side product of pomegranate production with cumbersome disposal costs for farmers. To explore value potential of immature fruits from pomegranate 'Wonderful' cultivars, the compositional landscapes and antitumorigenic activities of pomegranate extracts from two different stages of maturation were assessed. Cancer cell proliferation and cytotoxicity was quantified in human lung H1299 and colon HCT116 adenocarcinomas by crystal violet staining, MTS assay and caspase-3 activity. High performance liquid chromatography-diode array detector (HPLC/DAD) and high performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC/ESI-MS) analyses indicate that immature fruits are rich sources of gallotannins and ellagitannins, with the highest amounts contained in immature fruit peels. Biological investigations reveal a robust anticancer activity by those immature P. granatum fruit extracts, which reflected induction of tumor cytotoxicity and cell death mechanisms. Together, present observations suggest P. granatum byproducts from the thinning process may provide unexplored values for virtuous circular economy.


Assuntos
Extratos Vegetais/química , Punica granatum/metabolismo , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Frutas/química , Frutas/metabolismo , Humanos , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/farmacologia , Extratos Vegetais/farmacologia , Punica granatum/química , Espectrometria de Massas por Ionização por Electrospray
16.
Molecules ; 26(13)2021 Jun 26.
Artigo em Inglês | MEDLINE | ID: mdl-34206838

RESUMO

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1-4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC50 values are all > 50 µM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC50 values of 426.02 ± 11.31 µM. Compounds 2-4 displayed moderate tyrosinase inhibitory activities with IC50 values in the range of 124.74 ± 3.12-241.41 ± 6.23 µM. The structure-activity relationships indicate that hydroxylation at C-3', C-4', and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale.


Assuntos
Anti-Inflamatórios/análise , Inibidores Enzimáticos/farmacologia , Taninos Hidrolisáveis/análise , Melastomataceae/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Extratos Vegetais/química , Polifenóis/farmacologia , Animais , Anti-Inflamatórios/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Concentração Inibidora 50 , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Extratos Vegetais/análise , Polifenóis/química , Células RAW 264.7
17.
Food Chem ; 362: 130159, 2021 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-34167065

RESUMO

The sequential fractionation by supercritical-CO2 (SC-CO2) was applied to obtain fractions enriched in bioactive compounds of pomegranate peel, and we investigated if pomegranate peel extract and fractions would be effective to inhibit lipid and protein oxidation, and discolouration of bluefish patties stored at 4 °C for 9 days, after UV-C irradiation. The non-fractionated SC-CO2 extract from pomegranate peel was rich in phenolic compounds, mainly ellagitannins, besides, it possessed lipophilic compounds such as tocopherols and ß-carotene. These compounds were successfully separated by the fractionation protocols, in a lipid fraction concentrated in lipophilic compounds, and one or two fractions enriched with phenolic compounds, especially ellagitannins. The lipid fraction and the high phenolics fraction from pomegranate peel were then as effective as the synthetic antioxidant BHT in avoiding bluefish patties oxidation during refrigerated storage. Our data indicates that pomegranate peel fractions could be used to replace a synthetic antioxidant in fish meat.


Assuntos
Antioxidantes/química , Fracionamento Químico/métodos , Produtos Pesqueiros , Perciformes , Punica granatum/química , Animais , Antioxidantes/análise , Dióxido de Carbono/química , Cor , Proteínas de Peixes da Dieta/química , Conservação de Alimentos/métodos , Frutas/química , Taninos Hidrolisáveis/análise , Lipídeos/química , Oxirredução , Fenóis/análise , Extratos Vegetais/química , Tocoferóis/análise , Raios Ultravioleta
18.
Food Chem ; 358: 129833, 2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-33933967

RESUMO

This study identified and quantified hydrolysable tannins (HTs) in Terminalia ferdinandiana Exell (Kakadu plum) fruit, freeze dried powder extracted with 80% aqueous acetone (AA) and 80% aqueous acidified ethanol (AAE), using UHPLC-Q/Orbitrap/MS/MS. The vitamin C and ellagic acid were quantified by UHPLC-PDA. A total of seven HTs were identified: corilagin, 3,4,6-tri-O-galloyl-ß-d-glucose, elaeocarpusin, chebulinic acid, chebulagic acid, helioscopin B, and punicalagin, with five classified as ellagitannins. The two extracts AA and AAE, comprised of gallic acid (2.5 and 2.2 mg/g DW), punicalagins α and ß (2.8 and 1.3 mg/g DW), respectively, and both contained ellagic acid (~4 g/100 g DW). These extracts showed high antioxidant properties and strong antimicrobial effects against methicillin-resistant Staphylococcus aureus clinical isolate, Staphylococcus aureus, and Shewanella putrefaciens. These results suggest that Kakadu plum fruit is a rich, edible source of ellagitannins, ellagic acid and vitamin C with potential applications in food, cosmetic and nutraceutical industries.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Taninos Hidrolisáveis/química , Taninos Hidrolisáveis/farmacologia , Terminalia/química , Antibacterianos/química , Antioxidantes/química , Etanol/química , Liofilização , Frutas/química , Glucosídeos/análise , Glucosídeos/química , Taninos Hidrolisáveis/análise , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Extratos Vegetais/química , Pós , Solventes , Espectrometria de Massas em Tandem
19.
Food Chem ; 358: 129803, 2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-33945932

RESUMO

Success of clarification treatment in pomegranate juice is related to prevention of after-bottling haze formation and high anthocyanin content after pasteurization and during storage. Therefore, this study was conducted to achieve these targets with hydrocolloid [albumin (A), casein (C), chitosan (CH) and xanthan gum (XG)] combinations. While C, "A + XG" and "A + C" resulted in the greatest clarity after pasteurization, "A + C" and "A + C + CH" were associated with the greatest clarity during storage. In comparison with "A + C + CH" (k = 0.053 week-1), "A + C" (k = 0.065 week-1) was associated with more rapid improvement in clarity (23%). Greater clarity of "A + C" was associated with reductions in contents of punicalagins (r = -0.963), gallic (r = -0.936), chlorogenic (r = -0.995) and ellagic (r = -0.989) acids. However, "A + C + CH" clarity was associated with fewer proteins. Since copigmentation occurred between anthocyanins and phenolics, "A + C" enhanced colour density stability better (1.1 times) than "A + C + CH." Therefore, "A + C" is recommended producing pomegranate juice with high clarity and colour density after pasteurization and during storage.


Assuntos
Coloides/química , Armazenamento de Alimentos , Sucos de Frutas e Vegetais , Punica granatum , Albuminas/química , Antocianinas/análise , Antocianinas/química , Caseínas/química , Quitosana/química , Cor , Qualidade dos Alimentos , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/química , Pasteurização/métodos , Fenóis/análise , Fenóis/química , Polissacarídeos Bacterianos/química
20.
Food Chem ; 355: 129605, 2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-33799238

RESUMO

The aim of this study was to investigate phenolic compounds in peel, pulp and seeds of five different jabuticabas - Plinia trunciflora, "cabinho", P. cauliflora, cultivars "paulista" and "canaã-açu", P. jaboticaba, "sabará" and P. phitrantha, "branca-vinho". In addition to the commonly reported cyanidin-3-glucoside and delphinidin3-glucoside, it was also found the unreported cyanidin-3-coumaroylglucoside in the peels. Flavonols derived from quercetin and myricetin were also detected in jaboticaba peels, along with a wide variety of derivatives of ellagic acid and methyl ellagic acid. The latter derivatives occurred in acylated forms, which were not usually found in jabuticabas. The pulps and seeds of jabuticabas contained large amounts of ellagitannins vescalagin and castalagin, as well as gallic and ellagic acids. The jabuticabas showed small amounts of catechin and gallocatechin. P. jaboticaba showed the highest levels of anthocyanins and flavonols derived from myricetin, and P. phitrantha presented the highest concentration of ellagitannins and flavan-3-ols.


Assuntos
Myrtaceae/química , Fenóis/análise , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Ácido Elágico/análise , Ácido Elágico/química , Flavonóis/análise , Frutas/química , Frutas/metabolismo , Taninos Hidrolisáveis/análise , Myrtaceae/metabolismo , Fenóis/química , Análise de Componente Principal , Espectrometria de Massas por Ionização por Electrospray
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