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The escalation of many coronavirus variants accompanied by the lack of an effective cure has motivated the hunt for effective antiviral medicines. In this regard, 18 Saudi Arabian medicinal plants were evaluated for SARS CoV-2 main protease (Mpro) inhibition activity. Among them, Terminalia brownii and Acacia asak alcoholic extracts exhibited significant Mpro inhibition, with inhibition rates of 95.3 % and 95.2 %, respectively, at a concentration of 100 µg/mL. Bioassay-guided phytochemical study for the most active n-butanol fraction of T. brownii led to identification of eleven compounds, including two phenolic acids (1, and 2), seven hydrolysable tannins (3–10), and one flavonoid (11) as well as four flavonoids from A. asak (12–15). The structures of the isolated compounds were established using various spectroscopic techniques and comparison with known compounds. To investigate the chemical interactions between the identified compounds and the target Mpro protein, molecular docking was performed using AutoDock 4.2. The findings identified compounds 4, 5, 10, and 14 as the most potential inhibitors of Mpro with binding energies of −9.3, −8.5, −8.1, and −7.8 kcal mol−1, respectively. In order to assess the stability of the protein–ligand complexes, molecular dynamics simulations were conducted for a duration of 100 ns, and various parameters such as RMSD, RMSF, Rg, and SASA were evaluated. All selected compounds 4, 5, 10, and 14 showed considerable Mpro inhibiting activity in vitro, with compound 4 being the most powerful with an IC50 value of 1.2 µg/mL. MM-GBSA free energy calculations also revealed compound 4 as the most powerful Mpro inhibitor. None of the compounds (4, 5, 10, and 14) display any significant cytotoxic activity against A549 and HUVEC cell lines.

Condensed tannins in plants are found free and attached to protein and fibre but it is not known whether these fractions influence rumen degradation and microbial colonisation. This study explored the rumen degradation of tropical tannin-rich plants and the relationship between the disappearance of free and bound condensed tannin fractions and microbial communities colonising plant particles using in situ and in vitro experiments. Leaves from Calliandra calothyrsus, Gliricidia sepium, and Leucaena leucocephala, pods from Acacia nilotica and the leaves of two agricultural by-products: Manihot esculenta and Musa spp. were incubated in situ in the rumen of three dairy cows to determine their degradability for up to 96 h. Tannin disappearance was determined at 24 h of incubation, and adherent microbial communities were examined at 3 and 12 h of incubation using a metataxonomic approach. An in vitro approach was also used to assess the effects of these plants on rumen fermentation parameters. All plants contained more than 100 g/kg of condensed tannins with a large proportion (32–61%) bound to proteins. Calliandra calothyrsus had the highest concentration of condensed tannins at 361 g/kg, whereas Acacia nilotica was particularly rich in hydrolysable tannins (350 g/kg). Free condensed tannins from all plants completely disappeared after 24-h incubation in the rumen. Disappearance of protein-bound condensed tannins was variable with values ranging from 93% for Gliricidia sepium to 21% for Acacia nilotica. In contrast, fibre-bound condensed tannin disappearance averaged ∼ 82% and did not vary between plants. Disappearance of bound fractions of condensed tannins was not associated with the degradability of plant fractions. The presence of tannins interfered with the microbial colonisation of plants. Each plant had distinct bacterial and archaeal communities after 3 and 12 h of incubation in the rumen and distinct protozoal communities at 3 h. Adherent communities in tannin-rich plants had a lower relative abundance of fibrolytic microbes, notably Fibrobacter spp. whereas, archaea diversity was reduced in high-tannin-containing Calliandra calothyrsus and Acacia nilotica at 12 h of incubation. Concurrently, in vitro methane production was lower for Calliandra calothyrsus, Acacia nilotica and Leucaena leucocephala although for the latter total volatile fatty acids production was not affected and was similar to control. Here, we show that the total amount of hydrolysable and condensed tannins contained in a plant govern the interaction with rumen microbes affecting degradability and fermentation. The effect of protein- and fibre-bound condensed tannins on degradability is less important.

ABSTRACT: The present study was conducted to evaluate the efficacy of the dietary inclusion of commercial hydrolysable tannins (HT) on the growth performance and haemato-immunological parameters of Pacific white shrimp (Litopenaeus vannamei). Four isonitrogenous and isolipidic practical diets were formulated to contain 0; 0,1; 0,2 and 0,3% of HT obtained from the sweet chestnut (Castanea sativa). The 0,3% HT was designed to be included in a diet with a low level of fish meal (FM) (7,5%), while others included 10% FM. A total of 240 post larvae shrimp with an average initial body weight of 4.24 ± 0,03 g were randomly stocked in four groups, with four replicates per treatment and 15 shrimp per aquaria tank. Results showed that there were no significant differences in terms of final biomass, final mean weight, survival, weight gain (WG), feed conversion ratio (FCR) and thermal growth coefficient (TGC). However, biologically, a better performance was observed when the diets had higher inclusion levels of HT. Shrimp fed diets with 0,2 and 0,3% HT had a significantly higher total haemocytes count, and those fed the diet with 0,2% HT also had a significantly higher lysozyme activity, compared to shrimp from the control group. These results indicated that 0,2 and 0,3% HT could remarkably improve the growth performance and the haemato-immunological parameters of Pacific white shrimp, and have potential functional properties when included in commercial diets for shrimp.

Little information is available on the effects of different sources of tannins on ruminant product quality. Nowadays several tannin-rich extracts, produced from different plants, are available and contain tannins belonging to different chemical groups, but most of these have not been used so far as feed supplements. The present study aimed at comparing the effects of feeding three tannin extracts (one containing condensed tannins and two containing hydrolysable tannins) to lambs on growth performances and meat oxidative stability. Comisana male lambs were divided into four groups (n=9 each) and were fed for 75 days: a concentrate-based diet (CON), or CON supplemented with 4% tannin extracts from either mimosa (MI; Acacia mearnsii, De Wild; condensed tannins), chestnut (CH; Castanea sativa, Mill; hydrolysable ellagitannins) or tara (TA; Cesalpinia spinosa, (Molina) Kuntze; hydrolysable gallotannins). Only CH reduced growth rate, final weight, carcass weight and feed intake (P0.05). The TA diet increased (P

1,2,3,4,6-Penta-O-Galloyl-β-d-Glucose (PGG) is a hydrolysable tannin that belongs to the group of gallotannins but also participates in the formation of ellagitannins. PGG is composed of five galloyl groups with a glucose at its core and has structural characteristics that confer a high biological power. In this paper, we describe the chemistry of PGG, which is analyzed from a critical point regarding the types of synthesis, new sources of production from plants and by-products, highlighting the PGG obtaining, and its main functional properties recently reported in scientific literature. PGG has attracted attention because of its therapeutic potential and has shown functional properties as antimicrobial, anti-inflammatory, anti-carcinogenic, antidiabetic and antioxidant. Bioconversion from tannic acid can be potentialized with the use of biotechnological techniques. PGG can be obtained from natural sources as by-products. Research should continue to obtain pure molecules, in adequate quantity and with great biological activity.

An activity-guided isolation process was performed to identify the antioxidant constituents of Eucalyptus leaves (Eucalyptus grandis × Eucalyptus urophylla GL9). The ethyl acetate extract showed the highest activity in scavenging DPPH radical among five different fractions extracted from 70% aqueous ethanol extract of Eucalyptus leaves. Nine known compounds possessing radical scavenging activity, which included gallic acid (1), quercetin-3-O-β-d-glucuronide (Q-3-G-A) (2), ethyl gallate (3), tellimagrandin II(4), chlorogenic acid (5), 3-O-galloyl-4,6-O-[(S)-hexahydroxydiphenoyl]-d-glucose (gemin D) (6), pedunculagin (7), tellimagrandin I (8), and 1,2,3,4,6-penta-O-galloyl-β-d-glucose (PGG) (9) were isolated and identified from the ethyl acetate extract. Our results indicated that ethyl acetate extract and hydrolysable tannins among nine compounds exhibited great antioxidant activity in both chemical-based (e.g. DPPH and ABTS assays) and cellular-based (i.e., Hep G2) antioxidant assays, and PGG showed the highest cellular antioxidant activity. This study suggested that ethyl acetate extract and the hydrolysable tannins in Eucalyptus leaves would be promising natural antioxidants in pharmaceutical, feed and food supplement industries.

Acetonic extracts of pecan kernels and nutshells were fractionated using Sephadex LH-20 and three fractions were obtained from each. Only fraction II of both extracts contained simple polyphenols: catechin, epicatechin and ellagic acid were identified in kernel fraction II, while only epicatechin and ellagic acid were found in shell fraction II. Total gallic and ellagic acids were quantified in acid-hydrolyzed extracts: kernels contained 1.8 and 3.6 mg g−1, respectively, while nutshells contained 2.3 and 0.8 mg g−1, respectively. Kernel fraction III, containing high molecular weight compounds, showed the highest antioxidant activity and better antiproliferative activity in a cancer than a non-cancer cell line. Crude extracts showed cytotoxic activity in cerebellar granule neurons (CGNs), but shell extract was more cytotoxic; in contrast only kernel extract protected CGNs from H2O2-induced cell death. Thus, high molecular weight compounds of pecan kernel show noticeable bioactive properties and should be further characterised and analyzed as a rich source of bioactive polyphenols.

Condensed tannins in plants are found free and attached to protein and fibre but it is not known whether these fractions influence rumen degradation and microbial colonisation. This study explored the rumen degradation of tropical tannin-rich plants and the relationship between the disappearance of free and bound condensed tannin fractions and microbial communities colonising plant particles using in situ and in vitro experiments. Leaves from Calliandra calothyrsus, Gliricidia sepium, and Leucaena leucocephala, pods from Acacia nilotica and the leaves of two agricultural by-products: Manihot esculenta and Musa spp. were incubated in situ in the rumen of three dairy cows to determine their degradability for up to 96 h. Tannin disappearance was determined at 24 h of incubation, and adherent microbial communities were examined at 3 and 12 h of incubation using a metataxonomic approach. An in vitro approach was also used to assess the effects of these plants on rumen fermentation parameters. All plants contained more than 100 g/kg of condensed tannins with a large proportion (32-61%) bound to proteins. Calliandra calothyrsus had the highest concentration of condensed tannins at 361 g/kg, whereas Acacia nilotica was particularly rich in hydrolysable tannins (350 g/kg). Free condensed tannins from all plants completely disappeared after 24-h incubation in the rumen. Disappearance of protein-bound condensed tannins was variable with values ranging from 93% for Gliricidia sepium to 21% for Acacia nilotica. In contrast, fibre-bound condensed tannin disappearance averaged ∼ 82% and did not vary between plants. Disappearance of bound fractions of condensed tannins was not associated with the degradability of plant fractions. The presence of tannins interfered with the microbial colonisation of plants. Each plant had distinct bacterial and archaeal communities after 3 and 12 h of incubation in the rumen and distinct protozoal communities at 3 h. Adherent communities in tannin-rich plants had a lower relative abundance of fibrolytic microbes, notably Fibrobacter spp. whereas, archaea diversity was reduced in high-tannin-containing Calliandra calothyrsus and Acacia nilotica at 12 h of incubation. Concurrently, in vitro methane production was lower for Calliandra calothyrsus, Acacia nilotica and Leucaena leucocephala although for the latter total volatile fatty acids production was not affected and was similar to control. Here, we show that the total amount of hydrolysable and condensed tannins contained in a plant govern the interaction with rumen microbes affecting degradability and fermentation. The effect of protein- and fibre-bound condensed tannins on degradability is less important., (Copyright © 2022 The Author(s). Published by Elsevier B.V. All rights reserved.)

Tannins belong to plant secondary metabolites exhibiting a wide range of biological activity. One of the important aspects of the realization of the biological effects of tannins is the interaction with lipids of cell membranes. In this work we studied the interaction of two hydrolysable tannins: 1,2,3,4,6-penta-O-galloyl-β-d-glucose (PGG) and 1,2-di-O-galloyl-4,6-valoneoyl-β-d-glucose (T1) which had the same number of both aromatic rings (5) and hydroxyl groups (15) but differing in flexibility due to the presence of valoneoyl group in the T1 molecule with DMPC (dimyristoylphosphatidylcholine) lipid nano-vesicles (liposomes). Tannins-liposomes interactions were investigated using fluorescence spectroscopy, differential scanning calorimetry, laser Doppler velocimetry, dynamic light scattering and Fourier Transform Infra-Red spectroscopy. It was shown that more flexible PGG molecules stronger decreased the microviscosity of the liposomal membranes and increased the values of negative zeta potential in comparison with the more rigid T1. Both compounds diminished the phase transition temperature of DMPC membranes, interacted with liposomes via PO groups of head of phospholipids and their hydrophobic regions. These tannins neutralized DPPH free radicals with the stoichiometry of the reaction equal 1:1. The effects of the studied compounds on liposomes were discussed in relation to tannin quantum chemical parameters calculated by molecular modeling., (Copyright © 2021 Elsevier B.V. All rights reserved.)

Seeds collected from trees, shrubs and lianas growing on Barro Colorado Island, Panama, were analyzed for their content of phenolic compounds, oxidative activities and protein precipitation capacities. Proanthocyanidins and hydrolysable tannins were detected in one-third of 189 studied species. The most oxidatively active group of species were the ones containing prodelphinidins and ellagitannins whereas the species that had the highest protein precipitation capacity in relation to their total phenolics were the ones containing punicalagin. In addition, the oxidative activity and relative protein precipitation capacity were exceptionally high in the proanthocyanidin-rich genus Psychotria. This study offers a comprehensive overview on the tannin composition and the alkaline oxidative activities and protein precipitation capacities of the seeds of tropical plants., (Copyright © 2021 The Author(s). Published by Elsevier Ltd.. All rights reserved.)

Tannins are compounds able to form complexes with proteins limiting their ruminal degradation and thus the synthesis of some odour-active compounds may be inhibited. Tannins are broadly divided in condensed tannins (CT) and hydrolysable tannins (HT). The study aimed to assess the influence of dietary inclusion of three commercial tannin extracts, namely mimosa (Acacia mearnsii; CT), chestnut (Castanea sativa; HT) or tara (Caesalpinia spinosa; HT) on volatile profile and flavour of meat and kidney fat from lambs. Comisana male lambs were divided into four groups (n = 9 each) and fed for 75 days with a concentrate-based diet (CON) or CON supplemented with 4% of one of the tannin extracts. Tannins reduced "pastoral" odour in perirenal fat of lambs the meat of which was characterized by a very low perception of this attribute. It may be assumed that p-cresol and 8-methylnonanoic acid mostly contributed to "pastoral" odour expression in the diet without condensed or hydrolysable tannins., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

In this study, we screened 287 plant tissue samples from 175 plant species for their phenolic profiles. The samples were oxidized enzymatically in planta or at high pH in vitro to determine how these two oxidative conditions would alter the initial polyphenol profiles of the plant. Compounds that contained a pyrogallol or dihydroxyphenethyl group were highly active at pH 10. Enzymatic oxidation favored compounds that contained a catechol group, whereas compounds containing a pyrogallol group or monohydroxysubstituted phenolic moieties at most were oxidized less frequently. This study gives a broad overview of the distribution and alkaline oxidative activities of water-soluble phenolic compounds in plants as well as the enzymatic oxidative activities of various plant tissues., (Copyright © 2020 The Authors. Published by Elsevier Ltd.. All rights reserved.)

In this study, we report a methodology based on reversed phase LC (RP-LC) and hydrophilic interaction chromatography (HILIC) separations coupled to ion mobility (IM) and high resolution mass spectrometry (HR-MS) for the detailed analysis of hydrolysable tannins. The application of this approach to the analysis of an industrial chestnut (Castanea sativa, wood chips) tannin extract is demonstrated. A total of 38 molecular species, including a large number or isomers, were identified in this sample based on HR-MS (E) and UV absorption spectral information as well as retention behaviour in both separation modes. In total, 128 and 90 isomeric species were resolved by RP- and HILIC-LC-IM-TOF-MS, respectively. The combination of low- and high collision energy mass spectral data with complementary chromatographic separations allowed tentative and putative identification of twenty molecular species, comprising 78 isomers, in chestnut for the first time. Ion mobility resolved six new dimeric and trimeric vescalagin conformers with unique arrival (drift) times, including new conformers of roburin A-D which were not separated using either RP-LC or HILIC. HILIC was found to be the preferred separation mode for the analysis of vescalagin derivatives, while RP-LC is preferred for the analysis of ellagitannins with a cyclic glucose core. For the complete separation of the galloyl glucose species, comprehensive HILIC × RP-LC separation would be required., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Haemonchus contortus constitutes a severe problem for ruminant's production, it is the most frequent nematode parasite both in template and tropical regions, induces economical losses, and shows increasing resistance to currently available anthelmintics. Tannins are secondary metabolites that naturally fulfill defense functions in plants, representing a non-conventional, natural alternative in the treatment of gastrointestinal parasites in sheep. The objective of this work was to explore the in vitro anthelmintic activity of hydrolysable tannins on adult stage of Haemonchus contortus. Adults nematodes were obtained directly from the abomasum of ovines, and a dose response curve was performed with tannins extract at 0, 2, 4, 8, 25 and 50 mg/mL, and a time response curve at 0.5, 1, 2 and 24 h at 37 °C. Hydrolysable tannins decreased motility and induced mortality of H. contortus. We observed cuticle disruption around the mouth and reproductive organs, as well as evisceration. After 24 h of exposition, 8 mg/mL induced 83% of mortality and with 25 mg/kg 100% of mortality was achieved. The LD 50 was 3.54 mg/mL, while LD 90 was 10 mg/mL. We propose hydrolysable tannins as an alternative to contribute in the nematode control in ruminants., (Copyright © 2018. Published by Elsevier B.V.)

Little information is available on the effects of different sources of tannins on ruminant product quality. Nowadays several tannin-rich extracts, produced from different plants, are available and contain tannins belonging to different chemical groups, but most of these have not been used so far as feed supplements. The present study aimed at comparing the effects of feeding three tannin extracts (one containing condensed tannins and two containing hydrolysable tannins) to lambs on growth performances and meat oxidative stability. Comisana male lambs were divided into four groups (n=9 each) and were fed for 75 days: a concentrate-based diet (CON), or CON supplemented with 4% tannin extracts from either mimosa ( MI; Acacia mearnsii, De Wild; condensed tannins), chestnut (CH; Castanea sativa, Mill; hydrolysable ellagitannins) or tara (TA; Cesalpinia spinosa, (Molina) Kuntze; hydrolysable gallotannins). Only CH reduced growth rate, final weight, carcass weight and feed intake (P0.05). The TA diet increased (P<0.001) the concentration of γ-tocopherol in muscle and tended to increase that of α-tocopherol (P=0.058). Oxidative stability of raw and cooked meat, or of meat homogenates incubated with pro-oxidants, was not affected by the extracts. These results, compared with those reported in the literature, highlight that some effects of tannins cannot be easily generalized, but may strictly depend on their specific characteristics and on conditions inherent to the basal diet and the metabolic status of the animals.

Terminalia chebula fruits are one of the richest sources of hydrolysable tannins and it is well known medicinal agent in traditional systems of medicine for treatment of various chronic ailments. In the present study, hydrolysable tannin rich fraction (HTF) was isolated from 80% hydroalcoholic extract of Terminalia chebula fruit pericarps and it was studied for acute and repeated dose oral toxicity in Wistar albino rats. HTF did not show any toxic symptoms or mortality at single dose administration of 5000 mg/kg/p.o followed by observation for 14 days. On repeated dose 28 days oral toxicity study, administration of HTF at 1000 mg/kg showed marked reduction in body weight, food intake and water intake when compared with vehicle control. It was also observed that HTF could increase serum urea, glucose and AST level significantly when compared with vehicle control indicating mild disturbances in liver and kidney functions. On histopathological screening, HTF treatment showed a mild granulomatous inflammation in the liver and all other organs remained normal. It was concluded that following 28 days repeated dose oral administration, HTF caused mild disturbances in liver and kidney function which was indicated by reduced body weight, food and water intake, serum parameters and histological observations., (Copyright © 2017 Elsevier Inc. All rights reserved.)

Many studies quantify total phenolics or total tannins, but understanding the ecological role of polyphenolic secondary metabolites requires at least an understanding of the diversity of phenolic groups present. We used UPLC-MS/MS to measure concentrations of different polyphenol groups - including the four most common tannin groups, the three most common flavonoid groups, and quinic acid derivatives - in foliage from 628 eucalypts from the genera Eucalyptus, Angophora and Corymbia. We also tested for phylogenetic signal in each of the phenolic groups. Many eucalypts contained high concentrations of polyphenols, particularly ellagitannins, which have been relatively poorly studied, but may possess strong oxidative activity. Because the biosynthetic pathways of many phenolic compounds share either precursors or enzymes, we found negative correlations between the concentrations of several of the constituents that we measured, including proanthocyanidins (PAs) and hydrolysable tannins (HTs), HTs and flavonol derivatives, and HTs and quinic acid derivatives. We observed moderate phylogenetic signal in all polyphenol constituents, apart from the concentration of the prodelphinidin subunit of PAs and the mean degree of polymerisation of PAs. These two traits, which have previously been shown to be important in determining plants' protein precipitation capacity, may have evolved under selection, perhaps in response to climate or herbivore pressure. Hence, the signature of evolutionary history appears to have been erased for these traits. This study is an important step in moving away from analysing "totals" to a better understanding of how phylogenetic effects influence phenolic composition, and how this in turn influences ecological processes., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Ellagitannins are a subclass of hydrolysable tannins that have been suggested to function as defensive compounds of plants against herbivores. However, it is known that the conditions in the digestive tracts of different herbivores are variable, so it seems reasonable to anticipate that the reactivities and modes of actions of these ingested defensive compounds would also be different. A previous study on a few ellagitannins has shown that these polyphenolic compounds are highly oxidizable at high pH and that their bioactivity can be attributed to certain structural features. Herein, the activities of 13 ellagitannins using the deoxyribose assay were measured. The results provided information about the anti-oxidant, pro-oxidant and metal chelating properties of ellagitannins. Surprisingly, many of the tested ellagitannins exhibited pro-oxidant activities even at neutral pH and only moderate to low radical scavenging activities, although the metal chelating capacities of all tested ellagitannins were relatively high., (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Two new hydrolysable tannins, chebumeinin A (1) and chebumeinin B (2), together with eight known related compounds (3-10), were isolated from the fruits of Terminalia chebula. The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active., (Copyright © 2014 Elsevier B.V. All rights reserved.)

Previous studies of purified phenolic compounds have revealed that some phenolics, especially ellagitannins, can autoxidise under alkaline conditions, which predominate in the midgut of lepidopteran larvae. To facilitate screening for the pro-oxidant activities of all types of phenolic compounds from crude plant extracts, we developed a method that combined our recent spectrophotometric bioactivity method with an additional chromatographic step via UPLC-DAD-MS. This method allowed us to estimate the total pro-oxidant capacities of crude extracts from 12 plant species and to identify the individual phenolic compounds that were responsible for the detected activities. It was found that the pro-oxidant capacities of the plant species (i.e., the concentrations of the easily-oxidised phenolics) varied from 0 to 57 mg/g dry wt, representing from 0% to 46% of the total phenolics from different species. UPLC-DAD-MS analysis revealed that most flavonol and flavone glycosides were only slightly affected by alkaline conditions, thus indicating their low pro-oxidant activity. Interestingly, myricetin-type compounds differed from the other flavonoids, as their concentrations decreased strongly due to alkaline incubation. The same effect was detected for hydrolysable tannins and prodelphinidins, suggesting that a pyrogallol sub-structure could be a key structural component that partially explains their easy oxidation at high pH. Other types of phenolic compounds, such as hydroxycinnamic acids, were relatively active, as well. These findings demonstrate that this method displays the potential to identify most of the active and inactive pro-oxidant phenolic compounds in various plant species., (Copyright © 2014 Elsevier Ltd. All rights reserved.)