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The Quercus genus (oaks) comprises valuable plant resources that are used in many fields, including cosmetics, foods, and pharmaceuticals. Nonetheless, overall chemical profiling and anti-glycation component identification have not been thoroughly performed. In the present study, 70 % ethanolic and water extracts from three oak species (Quercus dentata, Q. serrata, and Q. aliena) showed antioxidant and anti-glycation potential. Thus, the components of the three oak species were profiled using ultra-performance liquid chromatography coupled with electrospray ionization and quadrupole time-of-flight mass spectrometry. The analysis showed that phenolic acids, ellagitannins, ellagic acid, procyanidin, and flavonoid (quercetin, myricetin, kaempferol, isorhamnetin, and taxifolin) glycosides are the main phenolic compounds. Based on the fluorescence assay, they act as strong inhibitors of non-enzymatic advanced glycation end-products (AGEs) formation in the bovine serum albumin (BSA) and skin proteins (collagen and elastin). Furthermore, mass fragmentation analysis demonstrated that ellagitannin, procyanidin B1 and flavonoid glycosides effectively trapped methylglyoxal (MGO), a reactive carbonyl intermediate and an important precursor of AGEs, to generate mono-, di-, or tri-MGO. Collectively, ellagic acid, ellagitannins, procyanidin B1, and flavonoid glycosides, the main active ingredients of three oak species (Q. dentata, Q. serrata, and Q. aliena), may be employed as lead structures in the development of functional foods or drugs to prevent diseases caused by aging and excessive sugar consumption.

This study compared the efficacy of aqueous extracts of commercially available pomegranate peel products and a juice powder in inhibiting the growth of two enterohemorrhagic Escherichia coli strains. Cell suspension of each E. coli strain (5 Log CFU/ml) was added into tryptic soy broth amended with 9 or 23% of each extract prepared with two different methods. After treatment for 5, 10, and 24 h at 25 °C, surviving E. coli cells were enumerated on tryptic soy agar to determine cell population reduction compared to the controls. The concentrations of six different ellagitannins and titratable activity in each treatment system were determined and correlated to E. coli cell population reduction. The extracts from three powdered pomegranate peels caused a significantly greater (p ≤ 0.05) reduction in E. coli population than the extract from the whole peel and juice powder. The higher dose of extracts resulted in a greater cell population reduction than the lower dose. The level of E. coli population reduction correlated positively with the total ellagitannins content (R2 0.67–0.98) and the titratable acidity (R2 0.69–0.98) in the treatment systems. The study suggests that pomegranate peels are promising natural additives or preservatives to control pathogens like EHEC.

Ellagitannin-rich food has been implicated to ameliorate cardiovascular risk, particularly blood pressure (BP). This systematic review and meta-analysis investigated the effect of ellagitannin-rich fruit consumption on BP. Five databases were screened and RCTs reporting the effect of ellagitannin-rich fruit consumption on BP and polyphenol content were included. Nineteen studies with 1,249 participants, showed a non-significant systolic blood pressure (SBP) and significant diastolic blood pressure (DBP) reduction, with ET-rich fruit consumption. Subgroup analysis revealed significant SBP reduction among hypertensives receiving 500–1000 mg polyphenol (-4.95 mmHg, 95 % CI: [-7.24, −2.66]) and among metabolic syndrome (MS) patients (-3.44 mmHg; 95 % CI: [-5.25, −1.63]). meta-regression revealed a positive association between polyphenol dosage and SBP changes. In conclusion, the consumption of ellagitannin-rich fruits may be considered an anti-hypertensive functional food/drink and recommended for patients who are at high risk for hypertension. Further well-designed trials are required to resolve the significant heterogeneities identified in the current literature.

Terminalia chebula, (Family: Combretaceae) is a medicinally active plant possess a wide spectrum of biological activities and contain numerous bioactive phytoconstituents like phenolic compounds, hydrolysable tannins, and flavonoids, therefore it may be considers as a good therapeutic alternative. Chebulinic acid, an ellagitannin was isolated from the fruits of Terminalia chebula and was known to possess numerous biological activities including anti-tumor activity, anti-atherogenic, anti-fibrotic, anti-inflammatory, antiulcer, antioxidant, hepatoprotective, antidiabetic, and antiviral etc. The present chapter describes the various analytical methods, structure elucidation, biological activities, pharmacokinetic, patents and various marketed formulations. Thus, chebulinic acid and related derivatives of Terminalia chebula and other plant species possess numerous pharmacological which paves way for further studies.

Background: Punicalagin (PG), a component of Punica granatum L., present a significant nutraceutical value in view of its numerous health-promoting properties and abundance. Interest in PG is driven by its complex structure, as the largest molecular weight ellagitannin. Promising results from the consumption of pomegranate juice in clinical trials against several ailments i.e., cardiovascular diseases, diabetes, and prostate cancer have been mostly attributed to its PG content. In recent years, PG has been demonstrated to exhibit excellent pharmacological bioactivities and has been proposed as a safe candidate for chemoprevention. Purpose: To assess the underlying PG's action mechanisms towards chronic diseases with high mortality and morbidity. Methods: Electronic databases including PubMed, ScienceDirect and Scopus were used to compile the literature. Papers describing the biological effects of punicalagin in vitro conditions, experimental animal models, and humans were selected and discussed. In addition, the extraction and isolation procedure with the highest punicalagin yield was included. Results: Among the 1757 primarily selected papers, only a final number of 119 studies were included. The mechanisms of actions ranged from selective induction of apoptosis of cancer cells, autophagy of cancer cells, decrease in oxidative stress, reduction of inflammation via down-regulation of pro-inflammatory factors and up-regulation of anti-inflammatory mediators to maintaining neuronal integrity. This review presents the latest research progress made towards PG role in the prevention and treatment of various chronic diseases and its protective health effects highlighting the need for future research in nutraceuticals. Despite the promising effects of punicalagin, there seems to be a need for human trials to confirm the effects at physiological levels as there can be substantial human inter-individual variability in response to punicalagin metabolism. Further, comparison of the different extraction and isolation methods are presented to highlight the most optimum for PG recovery. Conclusion: This review aims at improving the value-added applications of this unique dietary bioactive phenolic at a commercial scale in view of its role in health and disease management.

Ellagitannins (ETs) are hydrolysable tannins composed of a polyol core, primarily glucose, which is esterified with hexahydroxydiphenic acid (HHDP), and in some cases, gallic acid. ETs are the major phenolic compounds found in strawberries and may contribute to the health-related properties of strawberries, because of their strong antioxidative activity. However, their distribution in the strawberry fruit remains unclear. In this study, matrix-assisted laser desorption/ionization-mass spectrometry imaging (MALDI–MSI) was used to visualize ETs in ripe strawberry fruits. Five peaks, corresponding to the m/z values of ET [M−H]− ions detected in the MALDI–MS spectrum of strawberry extracts, were identified as strictinin, pedunculagin, casuarictin, davuriicin M1, and an unknown ET using MALDI–tandem MS (MS/MS). In addition, liquid chromatography–electrospray ionization–MS/MS of the extracts revealed the presence of pedunculagin isomers and the unknown ET. Ion images of these five ETs were reconstructed using MALDI–MSI. Strictinin was widely distributed in and around the achene seed coats, while the other ETs were dispersed in and around the seed coats, and at the bottom of the receptacle; pedunculagin was distributed in the epidermis and pith, whereas casuarictin, the unknown ET, and davuriicin M1 were distributed in the pith. Moreover, MALDI–MSI of a casuarictin standard indicated that in-source fragmentation weakly affected the ion images. The results suggest that the distribution of ETs depends on the presence or absence of their constituents, namely galloyl units, HHDP, and bis-HHDP. To the best of my knowledge, this is the first report on the visualization of ETs in plant tissues using MSI, MALDI–MSI may be a useful tool for analyzing the distribution of ETs in the strawberry fruit.

Despite the lack of its toxicity evaluation, traditional herbal products are being widely used for various health indications. Geraniin, an ellagitannin, is a bioactive compound found in many traditional herbal medicines. In spite its numerous health benefits ranging from anti-inflammatory, anti-hyperglycaemic, hepatoprotective, anti-cancer and anti-microbial, no toxicity data on geraniin is available. The objective of this study is to evaluate the acute oral toxicity of geraniin and an enriched geraniin-extract of Nephelium lappaceum L rind. This study followed the guidelines of the OECD 423 acute oral toxicity test. Subsequent to a single oral administration of the test compounds, the rats were observed for 14 days for signs of toxicity and mortality. Following euthanasia, full blood count, biochemistry of blood and histopathology assessment of organs were carried out. All parameters analysed indicated insignificant difference compared to control. The LD50 cut-off values for both geraniin and geraniin-enriched extract was established to be 2000 mg/kg b. w., following a single oral dose. It was however observed that the hepatocytes of three geraniin-administered rats exhibited a ‘foamy appearance’. As such, the no-observed-adverse-effect level of geraniin is below 2000 mg/kg, while that of geraniin-enriched extract is up to 2000 mg/kg. Further detailed toxicity studies are required to establish geraniin or its enriched extract from Nephelium lappaceum L rind safe for human consumption.

The contribution of Gordonibacter to the different abilities, both qualitative and quantitative, of individuals to transform dietary ellagic acid into anti-inflammatory urolithins was investigated. A specific and suitable q-PCR system was developed for the detection and quantification of Gordonibacter. Ellagic acid metabolism in the gut and faecal microbiota of healthy individuals, who consumed walnuts (n = 20) or a pomegranate extract (n = 49), were studied. Urolithin-A was positively correlated to Gordonibacter in faeces, whereas excretion of isourolithin-A and/or urolithin-B was inversely correlated to both. The relationship between Gordonibacter and urolithin-A found in vivo was also confirmed in vitro. This suggests that the beneficial effects attributed to the consumption of foods containing ellagic acid could be mediated by the individuals' Gordonibacter levels. The development of prebiotics, probiotics or synbiotic aimed at increasing Gordonibacter and related species could improve the individual's ability to produce the anti-inflammatory, cardioprotective and anticancer metabolite urolithin-A.

Pomegranate flowers is an ancient medicine that has commonly been used to treat various diseases such as diabetes. However, no reports are available on the metabolic profile of pomegranate flowers in vivo. In the present study, with the aid of HPLC-Q-TOF-MS 2 , 67 compounds were identified in pomegranate flowers extract, including 18 ellagitannins, 14 gallic acid and galloyl derivatives, five anthocyanins and 18 flavonoids. Seven compounds were firstly identified. In vivo, 22 absorbed compounds and 35 metabolites were identified in rat biosamples (urine, feces, plasma and tissues) after orally administered with pomegranate flowers extract. This result showed that not all compounds abundant in pomegranate flowers extract could be absorbed well in plasma and tissues. This finding also suggested a potential correlation between study on metabolic profile of these compounds in vivo and study on strategy of screening bioactivity of the isolates with in vitro cell systems evaluation. Notably, mono-glucuronide conjugated metabolite of ellagitannin compound (corilagin) was firstly identified. In addition, this is first report to identify phase II conjugate metabolites of ellagitannins in vivo after oral administration of ellagitannins-rich extracts (or foods). Thus, characterizing its multiple constitution, absorption and metabolic fate of these compounds in vivo is helpful to better analyze the active components in pomegranate flowers., (Copyright © 2019. Published by Elsevier B.V.)

Two new ellagitannins, lutescins A and B (1-2), along with eight known compounds (3-10), were isolated from the twigs of Trigonostemon lutescens. Their structures were elucidated by extensive spectroscopic analyses as well as by comparison with literature data. Compounds 1 and 2 are the first examples of ellagitannins reported in Trigonostemon Genus, and their structures featured a hexahydroxydiphenoyl (HHDP) moiety less often as R configurations in natural products. In addition, all isolated compounds were tested for their inhibitory effects against HeLa, HCT116 and HepG2 cancer cell lines. Compounds 1, 2, 5 showed potent antiproliferative activity, compared with the positive control Cisplatin., (Copyright © 2018 Elsevier B.V. All rights reserved.)

The results of a screening study, in which a total of 82 Finnish plant species were studied for their ellagitannin composition and content, are presented. The total ellagitannin content was determined by HPLC-DAD, the detected ellagitannins were further characterized by HPLC-ESI-QTOF-MS and divided into four structurally different sub-groups. Thirty plant species were found to contain ellagitannins and the ellagitannin content in the crude extracts varied from few mgg(-1) to over a hundred mgg(-1). Plant families that were rich in ellagitannins (>90mgg(-1) of the crude extract) were Onagraceae, Lyhtraceae, Geraniaceae, Elaeagnaceae, Fagaceae and some species from Rosaceae. Plant species that contained moderate amounts of ellagitannins (31-89mgg(-1) of the crude extract) were representatives of the family Rosaceae. Plant species that contained low amounts of ellagitannins (1-30mgg(-1) of the crude extract) were representatives of the families Betulaceae and Myricaceae. The specific ellagitannin composition of the species allowed their chemotaxonomic classification and the comparison between the older Cronquist's classification and the nowadays preferred Angiosperm Phylogeny Group classification., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

FR429, an ellagitannin (a type of polyphenol), is isolated and purified from Polygonum capitatum Buch.-Ham.ex D. Don which is the original herbal medicine of the "Re-Lin-Qing" formula used clinically to treat urinary tract infection in China. FR429 has been investigated for its antitumor potential in tumor-bearing nude mice in vivo, but its in vitro anti-tumor effect in hepatoma cell lines was low. Thus, it was of our interest to investigate its metabolism pathways for supporting its in vivo antitumor potential. The metabolic profiles of FR429 were studied in vitro by liquid chromatography coupled to ion trap time-of-flight mass spectrometry. Total eight metabolites were identified in rat and human liver microsomes, cytosol, and rat primary hepatocytes in vitro. Ellagic acid, a reported anti-angiogenic agent, was one of the main metabolites in these biological matrices. Methylated metabolites catalyzed by catechol-O-methyl transferase (COMT) were observed mainly in the in vitro incubation with rat liver cytosol, which was verified by using a COMT specific inhibitor entacapone and supported by molecular docking analysis. Methylated and sulfated metabolites were also found in rat primary hepatocytes in a time-dependent manner. In conclusion, the in vitro metabolism pathways of FR429 were hydrolysis, methylation and sulfation. The anti-tumor effects of its major metabolites should be further studied., (Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.)

The natural product oenothein B (OeB), a dimeric macrocyclic ellagitannin, has a wide range of biological activities, such as antioxidant, anti-inflammatory, anti-viral, antifungal, and antitumor. However, investigations concerning its genotoxicity have not been carried out. This study assessed the cytotoxicity, genotoxicity, and protective effects of oenothein B using in vitro SOS-Inductest and in vivo mouse bone marrow micronucleus (MN) assay through oral and intraperitonial routes. In both assays oenothein B did not produce genotoxic effects in any of doses tested; in contrast, cytotoxic effect in cells was detected only in mice groups treated by both routes and exposed for 24 and 48h. Antigenotoxic and anticytotoxic activities of oenothein B were evaluated using both assays in combination with mitomycin C (MMC), a bioreductive alkylating agent. In the MN assay, a significant reduction was observed in MN frequency in all groups co-treated with MMC and OeB compared to those which received only MMC. Anticytotoxicity was observed in mice groups exposed to OeB and MMC for 24 and 48h. In the SOS-Inductest, oenothein B failed to show antigenotoxic and anticytotoxic effects; thus, it undoubtedly showed an in vivo protective activity against primary DNA damage induced by mitomycin C., (Copyright © 2014 Elsevier B.V. All rights reserved.)