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1.
Anal Methods ; 16(16): 2513-2521, 2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38587209

RESUMO

Sweet tea is a functional herbal tea with anti-inflammatory, anti-diabetic, and other effects, in which phloridzin and trilobatin are two functional compounds. However, the current methods for their quantification are time-consuming, costly, and environmentally unfriendly. In this paper, we propose a rapid method that integrates online pressurized liquid extraction and high-performance liquid chromatography featuring a superficially porous column for fast separation. Moreover, we employ an equal absorption wavelength method to eliminate using multiple standard solutions and relative calibration factors. Our verification process corroborated the technique's selectivity, accuracy, precision, linearity, and detection limitations. Separately, our methodology demonstrated excellent analytical efficiency, cost-effectiveness, and environmental friendliness. Practical application using six distinct batches of sweet tea samples yielded results in congruence with the external standard method. The analytical rate of this technique is up to over 18 times faster than traditional methods, and organic solvent consumption has been reduced to less than 1.5 mL. Therefore, this method provides a valuable way to achieve quality control and green analysis of sweet tea and other herbal teas.


Assuntos
Florizina , Cromatografia Líquida de Alta Pressão/métodos , Florizina/análise , Florizina/química , Chás de Ervas/análise , Taninos Hidrolisáveis/análise , Extração Líquido-Líquido/métodos , Reprodutibilidade dos Testes
2.
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
3.
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
4.
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
5.
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
6.
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
7.
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
8.
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
9.
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
10.
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
11.
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
12.
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
13.
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
14.
J Ethnopharmacol ; 275: 114135, 2021 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-33892063

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Terminalia chebula (TC), a well-known Indian Ayurvedic medicine introduced into China in the Sui and Tang Dynasties, has been recorded and used medicinally as Fructus Chebulae, together with its variety tomentella (TCT) in the Chinese Pharmacopoeia. They have been also used commonly for the treatment of diabetes mellitus by Tibetan medicine. AIM OF THE STUDY: To investigate the main bioactive and therapeutic principles in the fruits of TCT, based on the extensive evaluation of their anti-inflammatory and hypoglycemic activities. MATERIALS AND METHODS: The TCT fresh fruits were analyzed by HPLC and separated further by column chromatography and preparative HPLC. The isolated compounds were identified by extensive spectroscopic analyses, including 1D/2D NMR, MS, UV, IR and ECD. Anti-inflammatory activity was evaluated by inhibition of NO production in RAW264.7 cells. The specific iNOS (PDB ID: 3E7G) structure was prepared by Discovery Studio 4.0, and the molecular docking simulation was performed on GOLD (version 5.2.2). Hypoglycemic activity was measured using the substrate solution of 4-nitrophenyl-α-d-glucopyranoside enzyme and buffer solution. RESULTS: The HPLC analysis method of polyphenols in the fruits of TCT was established, and 13 main chromatographic peaks were identified, including six hydrolyzable tannins (2, 4-7, 10-11), three simple phenols (12-14), and one oleanane pentacyclic triterpene, arjungenin. Extensive chromatographic separation of TCT fresh fruits yielded 14 compounds, including one new natural hydrolyzable tannin, 2,3-(S)-HHDP-6-O-galloyl-d-glucose (1). The known compounds were identified as 10 hydrolyzable tannins (2-11) and three simple phenols (12-14). Compounds 10 (IC50 = 36.43 ± 0.21 µM), 11 (IC50 = 42.28 ± 0.09 µM) displayed stronger NO inhibitory activity than the positive control L-NMMA (IC50 = 42.34 ± 0.66 µM), while 2, 4, and 9 showed moderate inhibitory activity against NO production. Further molecular docking simulation of specific iNOS on 10 and 11, as well as five previously isolated lignans 15-19 showed that there were no obvious rules between docking results and the in vitro NO inhibitory activity for hydrolyzable tannins (10 and 11), while the mechanism of anti-inflammatory activity for lignans was related to the substitution of conjugated aldehyde groups. Moreover, most of the hydrolyzable tannins (1-2, 4-5, 9-11) and simple phenol (12) displayed stronger inhibitory effects on α-glucosidase than the positive control, quercetin (IC50 = 6.118 ± 0.071 µM), with IC50 values ranging from 0.079 to 16.494 µM. Among these bioactive isolates, the hydrolyzable tannins 2, 4-5, and 9-11, and simple phenol 12 are major chemical components in TCT fruit. CONCLUSIONS: The results showed that lignans and hydrolyzed tannins are the main active ingredients of TCT fruits, responsible for the traditional treatment of sore throat and cough. Moreover, hydrolyzed tannins and simple phenolic compounds with potential hypoglycemic activity are closely related to the ethno-pharmacological uses of TCT fruits on diabetes in Tibetan medicine.


Assuntos
Anti-Inflamatórios/farmacologia , Hipoglicemiantes/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Terminalia/química , Animais , Anti-Inflamatórios/análise , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Frutas/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/química , Taninos Hidrolisáveis/farmacologia , Hipoglicemiantes/análise , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Técnicas In Vitro , Lignanas/análise , Lignanas/química , Lignanas/farmacologia , Camundongos , Simulação de Acoplamento Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/química , Fenóis/análise , Fenóis/química , Fenóis/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/química , Células RAW 264.7 , Triterpenos/análise , Triterpenos/química , Triterpenos/farmacologia , alfa-Glucosidases/metabolismo
15.
Food Chem ; 334: 127565, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-32717686

RESUMO

The chemical composition, antioxidant activity (AA), cytotoxic activity, antihemolytic effects, and enzyme inhibition (EI) of lyophilized jabuticaba (Myrciaria jaboticaba) seed extract (LJE) was studied. The main compounds found were castalagin, vescalagin, procyanidin A2, and ellagic acid. LJE was more toxic to cancer cells than to normal cells, meaning relative toxicological safety. This cytotoxic effect can be attributed to the pro-oxidant effect observed in the reactive oxygen species (ROS) generation assay. LJE inhibited α-amylase, α-glucosidase, and ACE-I activities and protected human erythrocytes from hemolysis. LJE was incorporated into yogurts at different concentrations and the total phenolic content, AA, and EI increased in a dose-dependent manner. LJE-containing yogurt presented 86% sensory acceptance. The yogurt was administered to Wistar rats bearing cancer and it modulated the gut bacterial microbiota, having a prebiotic effect. LJE is a potential functional ingredient for food companies looking for TPC, AA, and prebiotic effect in vivo.


Assuntos
Neoplasias do Colo/tratamento farmacológico , Microbioma Gastrointestinal/efeitos dos fármacos , Myrtaceae/química , Polifenóis/farmacologia , Iogurte , 1,2-Dimetilidrazina/toxicidade , Inibidores da Enzima Conversora de Angiotensina/química , Inibidores da Enzima Conversora de Angiotensina/farmacologia , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Catequina/análise , Catequina/farmacologia , Neoplasias do Colo/induzido quimicamente , Neoplasias do Colo/microbiologia , Humanos , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/farmacologia , Masculino , Fenóis/análise , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Polifenóis/análise , Proantocianidinas/análise , Proantocianidinas/farmacologia , Ratos Wistar , Sementes/química , alfa-Amilases/antagonistas & inibidores
16.
Phytomedicine ; 77: 153278, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32781393

RESUMO

BACKGROUND: Terminalia bellirica (Gaertn.) Roxb. is one of the oldest medicinal herbs of India, Pakistan, Nepal, Bangladesh and Sri Lanka as well as South-East Asia. Its medicinal utility has been described in the different traditional medicinal systems, such as Ayurveda, Unani, Siddha, and traditional Chinese medicine. PURPOSE: The present study is aimed at providing a comprehensive overview on the traditional medicinal use, major phytoconstituents, biological and pharmacological activities and related mechanisms of actions and clinical studies of T. bellirica. Another objective is to describe current limitations and future direction of T. bellirica-related research. METHODS: PubMed, ScienceDirect, Scopus, Cochrane Library, and EBOSCO host databases were selected to explore literature published between 1980 and 2020 (till March). Keywords used in various combinations comprised of Terminalia bellirica, phytoconstituents, health effects, pharmacological activities, molecular targets, in vitro, in vivo, clinical studies, and disease prevention. RESULTS: A broad spectrum in vitro and in vivo studies suggested various biological and pharmacological effects, including antioxidant, anti-inflammatory, immunomodulatory, antimicrobial, hepatoprotective, renoprotective, antidiabetic, anti-hyperlipidemic, and anticancer activities. Diverse bioactivities of T. bellirica have been ascribed to the presence of many bioactive phytochemicals, such as glucoside, tannins, gallic acid, corilagin, ellagic acid, ethyl gallate, galloyl glucose, chebulagic acid, and arjunolic acid. CONCLUSION: Preclinical and clinical studies have suggested that T. bellirica plant and its phytoconstituents have immense potential for prevention and treatment of various diseases. Additional in vivo studies and clinical trials are warranted to realize the complete medicinal attributes of this plant.


Assuntos
Compostos Fitoquímicos/análise , Extratos Vegetais/farmacologia , Terminalia/química , Animais , Antioxidantes/farmacologia , Ácido Gálico/análogos & derivados , Ácido Gálico/análise , Glucosídeos/análise , Humanos , Taninos Hidrolisáveis/análise , Ayurveda , Extratos Vegetais/química , Plantas Medicinais/química , Taninos/análise , Triterpenos/análise
17.
Food Chem ; 328: 126833, 2020 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-32480265

RESUMO

Raspberries are rich in polyphenols but the impact of organic versus conventional agricultural practices on their phytochemical composition is not well known. This study aimed to analyse and compare the polyphenol accumulation in raspberries grown under both agricultural practices in the same edaphoclimatic conditions. Two raspberry cultivars 'Kweli' and 'Tulameen' were used. Under organic agricultural practices, the polyphenols levels increased for the 'Kweli' cultivar but decreased for the 'Tulameen' cultivar. 'Tulameen' cultivar grown under conventional agricultural practices contained higher anthocyanins levels than grown under organic agricultural practices while for the 'Kweli' cultivar no significant differences were observed between the two agricultural practices. 'Kweli' cultivar presented a significantly higher amount of ellagitannins and ellagic acid derivatives when compared to the 'Tulameen' cultivar under both agricultural practices. The effect of the agricultural practices on the raspberries' chemical profile was dependent on the cultivar and cannot be generalised.


Assuntos
Agricultura , Compostos Fitoquímicos/análise , Rubus/química , Antocianinas/análise , Cromatografia Líquida de Alta Pressão , Ácido Elágico/análise , Frutas/química , Frutas/metabolismo , Taninos Hidrolisáveis/análise , Extratos Vegetais/química , Polifenóis/análise , Polifenóis/química , Rubus/metabolismo
18.
Molecules ; 25(12)2020 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-32575814

RESUMO

In the last few years, the consumer's concern with the relationship between health and diet has led to the search of foods with functional properties beyond the nutritional. In this framework, the consumption of pomegranate has increased due to their sensorial attributes and remarkable amounts of bioactive compounds, which generate, at the same time, huge amounts of by-products. A search in the Scopus database for the last 10 years has revealed the rising interest in pomegranate peel (PP), the main residue from this fruit. The meat industry is a food sector that has had to search for new alternatives to substitute the use of synthetic preservatives by new natural additives, to extend the self-life and keep the quality attributes of their processed products. This review sets out the main bioactivities of PP extracts, and their incorporation in meat products is elaborated. PP is a good source of bioactive compounds, including phenolic acids, flavonoids and hydrolyzable tannins, which have beneficial health effects. It can be concluded that the reformulation of meat products with PP extracts is a suitable strategy for enhancing their technological characteristics, in addition to conferring functional properties that make them healthier and potentially more acceptable for the consumer.


Assuntos
Anti-Infecciosos/análise , Antioxidantes/análise , Conservantes de Alimentos/química , Frutas/química , Produtos da Carne/análise , Extratos Vegetais/química , Punica granatum/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Flavonoides/análise , Conservantes de Alimentos/análise , Taninos Hidrolisáveis/análise , Hidroxibenzoatos/análise , Produtos da Carne/normas , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Polissacarídeos/metabolismo , Punica granatum/metabolismo , Metabolismo Secundário
19.
Food Res Int ; 131: 109026, 2020 05.
Artigo em Inglês | MEDLINE | ID: mdl-32247467

RESUMO

This work aimed to contribute to the nutritional and functional characterization of roasted baru nuts, a seed widely consumed and produced in Brazil. Baru nut was characterized in terms of its nutritional value and volatile composition (SPME-GC-MS analysis). The ultrasound assisted extraction was used to extract free and bound phenolic compounds that were identified by LC-DAD-ESI-MS/MS method. Bioactivity assays were carried out to evaluate the antioxidant activity (ORAC and HOSC assay) and anticancer effect (inhibition of HT29 cell growth and targeting of cancer stemness) of baru nut extracts and phenolic compounds. Results showed that baru is a good source of protein and monounsaturated fatty acids, specifically oleic acid (47.20 g/100 g). The predominant volatile compounds are hexanal (71.18%) and 2,5-dimethyl-pyrazine (9.43%). The main phenolic compounds identified were gallic acid and its derivatives, such as gallic acid esters and gallotannins. Among all, gallic acid and methyl gallate seemed to be the main compounds responsible for the high antioxidant activity. The antiproliferative effect evaluated of baru extracts in HT29 cell line showed ability to impair cell growth in both monolayer and spheroid cultures and to reduce ALDH+ population. These results supply new information about the functional compounds presents in baru nut, which are important sources of natural antioxidants and antiproliferative compounds.


Assuntos
Antioxidantes/análise , Dipteryx/química , Valor Nutritivo , Nozes/química , Fenóis/análise , Brasil , Proliferação de Células/efeitos dos fármacos , Cromatografia Líquida , Ácidos Graxos/análise , Ácido Gálico/análogos & derivados , Ácido Gálico/análise , Cromatografia Gasosa-Espectrometria de Massas , Células HT29 , Humanos , Taninos Hidrolisáveis/análise , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Sementes/química , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem , Compostos Orgânicos Voláteis/análise
20.
Molecules ; 25(5)2020 Feb 26.
Artigo em Inglês | MEDLINE | ID: mdl-32110993

RESUMO

Amariin is an ellagitannin with two dehydrohexahydroxydiphenoyl (DHHDP) moieties connecting glucose 2,4- and 3,6-hydroxy groups. This tannin is predominant in the young leaves of Triadica sebifera and Carpinus japonica. However, as the leaves grow, the 3,6-DHHDP is converted to its reduced form, the hexahydroxydiphenoyl (HHDP) group, to generate geraniin, a predominant ellagitannin of the matured leaves. The purified amariin is unstable in aqueous solution, and the 3,6-(R)-DHHDP is spontaneously degraded to give HHDP, whereas 2,4-(R)-DHHDP is stable. The driving force of the selective reduction of the 3,6-DHHDP of amariin is shown to be the conformational change of glucose from O,3B to 1C4. Heating geraniin with pyridine affords 2,4-(R)-DHHDP reduction products. Furthermore, the acid hydrolysis of geraniin yields two equivalents of ellagic acid. Although the reaction mechanism is still ambiguous, these results propose an alternative biosynthetic route of the ellagitannin HHDP groups.


Assuntos
Ésteres/síntese química , Taninos Hidrolisáveis/síntese química , Betulaceae/química , Cromatografia Líquida de Alta Pressão , Ésteres/química , Euphorbiaceae/química , Glucosídeos/análise , Glucosídeos/química , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/química , Espectroscopia de Ressonância Magnética , Oxirredução , Extratos Vegetais/química , Folhas de Planta/química
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