Galloylglucoses Research Articles

Determination of phenolics and proteins causing sediment formation in pomegranate juice using “Tannase+Lactonase” and “Protease”

In this study, pomegranate juice (PJ) was treated with “tannase+lactonase [human-derived (H-PON-1) or rabbit-derived (R-PON-1)]” or “protease [aspartic protease (AP) or cysteine protease (CP)].” After treatment, effects of tannins, proteins and amino acids on sediment formation were determined during storage at 20℃. Among proteins, prolamin showed the highest effect in PJ treated with “tannase+H-PON-1/R-PON-1” and CP. While amino acids did not affect sediment formation in “tannase+H-PON-1/R-PON-1” or AP treatments, only glycine increased sediment content in CP treatment. Removal of galloyl and/or HHDP groups from HHDP-galloyl-glucose-isomer, pedunculagin-2 and punigluconin by “tannase+H-PON-1/R-PON-1” was very effective in preventing sediment formation. Prolamin:galloyl glucose isomer ratio and HHDP-galloyl-hexoside-2 and HHDP-galloyl-glucuronide contents should be 23.244±1.162 and, 1.254±0.063 and 0.679±0.034 mg/L to prevent sediment, respectively. Since common parameters preventing sediment formation in both methods that target removal of tannins and/or proteins were punigluconin content and prolamin:punicalagin-2 ratio, these two parameters must also be considered in sediment-free PJ production.

Molecular Dynamics Simulation Studies of Beta-Glucogallin and Dihydro Dehydro Coniferyl Alcohol from Syzygium cumini for its Antimicrobial Activity on Staphylococcus aureus.

With the escalating threat of antimicrobial resistance (AMR), discovering novel therapeutic agents against resistant pathogens like Staphylococcus aureus is crucial. This study explores phytochemicals from Syzygium cumini for their potential efficacy against AMR S. aureus infections, elucidating their mechanisms through in silico methods. We investigated 83 compounds from S. cumini, sourced from PubMed, using rigorous docking analysis against the ATP binding domain AgrC of S. aureus with AMdock with Autodock Vina v1.5.2. Drug-likeness predictions were assessed using SwissADME v2023 and Pass online v2.0. Molecular dynamics (MD) simulations identified promising compounds, focusing on stability and interaction dynamics. Beta-Glucogallin (BEG) and Dihydro Dehydro Coniferyl alcohol (DIH) emerged as significant hits. MD simulations with GROMACS v2020.6 revealed stable BEG and DIH complexes with AgrC, forming six hydrogen bonds with six key amino acids (Arg-303, Asp-338, Glu-342, Glu-384, Lys-389, Gly-396), indicating strong and stable bonding. The binding affinities for DIH and BEG are -73.474 ± 11.104 kJ/mol and -6.319 ± 18.823 kJ/mol with 4BXI, respectively. Our findings highlight BEG and DIH as promising candidates against AMR S. aureus infections, showing favourable binding affinities and stable interactions with AgrC. This study underscores the importance of natural products in combating AMR and demonstrates the utility of computational methodologies in drug discovery. Further experimental validation is warranted to fully exploit these phytochemicals' therapeutic potential.

Characterization of physicochemical properties, flavor volatiles and phenolic compounds of feijoa fruit varieties

Thirteen varieties of feijoa (Feijoa sellowiana) fruit were collected and the physical and chemical properties of feijoa peel, flesh, seed, and leaf were analyzed. Large diversities in the physicochemical characteristics and phenolic and volatile composition among various parts and between different varieties of feijoa were observed. Degrees Brix of whole fruits ranged from 10.1 (Anatoki) to 18.0 (No. 2) °Brix. Procyanidin B-type tetramer, procyanidin B-type dimer, and procyanidin C-type trimer had the highest concentrations in all parts and varieties of feijoa. Caffeoyl glucose, dihydroferulic acid 4-O-glucuronide, galloyl glucose, and lariciresinol-sesquilignan were detected in feijoa fruits and leaves. A total of 105 esters, 68 terpenes, 20 alcohols, 31 hydrocarbons, 12 aldehydes, and 11 ketones were related to aromatic attributes of fruits and leaves. Early season and mid-season varieties had larger variations in the chemical properties than late-season varieties. Anatoki, Kakariki, and No.1, have the potential to be developed for attractive flavor and functional properties.

Metabolic profiling, antioxidant, and enzyme inhibition potential of Iris pseudacorus L. from Egypt and Japan: A comparative study

Genus Iris comprises numerous and diverse phytoconstituents displaying marked biological activities. The rhizomes, and aerial parts of Iris pseudacorus L. cultivars from Egypt and Japan were subjected to comparative metabolic profiling using UPLC-ESI-MS/MS. The antioxidant capacity was determined using DPPH assay. In vitro enzyme inhibition potential against α-glucosidase, tyrosinase and lipase was evaluated. In silico molecular docking was conducted on the active sites of human α-glucosidase and human pancreatic lipase. Forty-three compounds were tentatively identified including flavonoids, isoflavonoids, phenolics and xanthones. I. pseudacorus rhizomes extracts (IPR-J and IPR-E) exhibited the highest radical scavenging activity with IC50 values of 40.89 µg/mL and 97.97 µg/mL, respectively (Trolox IC50 value was 14.59 µg/mL). Moreover, IPR-J and IPR-E exhibited promising α-glucosidase inhibitory activity displaying IC50 values of 18.52 µg/mL, 57.89 µg/mL, respectively being more potent as compared to acarbose with IC50 value of 362.088 µg/mL. All extracts exerted significant lipase inhibitory activity exhibiting IC50 values of 2.35, 4.81, 2.22 and 0.42 µg/mL, respectively compared to cetilistat with IC50 value of 7.47 µg/mL. However, no tyrosinase inhibitory activity was observed for all I. pseudacorus extracts up to 500 µg/mL. In silico molecular modelling revealed that quercetin, galloyl glucose, and irilin D exhibited the highest fitting scores within the active sites of human α-glucosidase and pancreatic lipase. ADMET prediction (absorption, distribution, metabolism, excretion, and toxicity) showed that most of the phytoconstituents exhibited promising pharmacokinetic, pharmacodynamics and tolerable toxicity properties. According to our findings, I. pseudacorus might be considered as a valuable source for designing novel phytopharmaceuticals.

New insights into the function of plant tannase with promiscuous acyltransferase activity.

Plant tannases (TAs) or tannin acyl hydrolases, a class of recently reported carboxylesterases in tannin-rich plants, are involved in the degalloylation of two important groups of secondary metabolites: flavan-3-ol gallates and hydrolyzable tannins. In this paper, we have made new progress in studying the function of tea (Camellia sinensis) (Cs) TA-it is a hydrolase with promiscuous acyltransferase activity invitro and invivo and promotes the synthesis of simple galloyl glucoses and flavan-3-ol gallates in plants. We studied the functions of CsTA through enzyme analysis, protein mass spectrometry, and metabolic analysis of genetically modified plants. Firstly, CsTA was found to be not only a hydrolase but also an acyltransferase. In the two-step catalytic reaction where CsTA hydrolyzes the galloylated compounds epigallocatechin-3-gallate or 1,2,3,4,6-penta-O-galloyl-β-d-glucose into their degalloylated forms, a long-lived covalently bound Ser159-linked galloyl-enzyme intermediate is also formed. Under nucleophilic attack, the galloyl group on the intermediate is transferred to the nucleophilic acyl acceptor (such as water, methanol, flavan-3-ols, and simple galloyl glucoses). Then, metabolic analysis suggested that transient overexpression of TAs in young strawberry (Fragaria × ananassa) fruits, young leaves of tea plants, and young leaves of Chinese bayberry (Myrica rubra) actually increased the total contents of simple galloyl glucoses and flavan-3-ol gallates. Overall, these findings provide new insights into the promiscuous acyltransferase activity of plant TA.

A multifunctional key to open a new window on the path to natural resources-lessons from a study on chemical composition and biological capability of Paeonia mascula L. from Turkey

The genus Paeonia has gained great interest from the scientific community for exploration as a source of bioactive compounds. The current work focused on the chemical characterisation and biological properties of Paeonia mascula L. from Turkey. The chemical characterisation of the extracts was analysed by LC-DAD-ESI and LC-APCI-MS. The antioxidant, enzyme inhibitory and anticancer properties were evaluated in vitro. The methanol extract was the most effective as antioxidant, metal chelator and was the most effective inhibitor of acetylcholinesterase (AChE) and tyrosinase. The chloroform extract showed highest inhibition of butrylcholinesterase (BChE) and amylase. Ethyl acetate extract displayed glucosidase inhibition. The most abundant compounds were hexagalloyl glucose, penta galloyl glucose, gallic acid, tetragalloyl glucose, paeoniflorin and the most abundant flavonoid was quercetin-3-O-glucoside. β-sitosterol was the most abundant phytosterol. The anticancer effect of P. mascula was evaluated by using HELA cells evaluating different pathways. The possible inhibition effect of P. mascula on the reactive oxygen species (ROS) pathway was controlled by performing the advanced glycation end product (AGE). To determine the effect of P. mascula on active molecular pathways in the HELA cancer cell line, the levels of Phospho-NF-Kβ p65, AGE receptor RAGE protein, antiapoptotic BCL-2, proapoptotic BAX and P-53 proteins were checked, respectively. Phospho-NF-Kβ p65, RAGE and BCL-2, which are both ROS inducers and play an active role in cancer prognosis, were found to have decreased levels after the application of P. mascula. Our findings provide a scientific basis for Paeonia mascula, which may serve as a source of naturally occurring bioactive compounds for healthpromoting applications.

Glucogallin Attenuates the LPS-Induced Signaling in Macrophages and Protects Mice against Sepsis.

The anti-oxidant and anti-inflammatory effect of beta-glucogallin (BGG), a plant-derived natural product, was evaluated in both in vitro and in vivo studies. For the in vitro study, the ability of BGG pre-treatment to quench LPS-induced effects compared to LPS alone in macrophages was investigated. It was found that BGG pre-treatment showed a significant decrease in ROS, NO, superoxide, and pro-inflammatory cytokines (TNF-alpha, IL-4, IL-17, IL-1β, and IL-6) and increased reduced glutathione coupled with the restoration of mitochondrial membrane potential. Gene profiling and further validation by qPCR showed that BGG pre-treatment downregulated the LPS-induced expression of c-Fos, Fas, MMP-9, iNOS, COX-2, MyD88, TRIF, TRAF6, TRAM, c-JUN, and NF-κB. We observed that BGG pre-treatment reduced nuclear translocation of LPS-activated NF-κB and thus reduced the subsequent expressions of NLRP3 and IL-1β, indicating the ability of BGG to inhibit inflammasome formation. Molecular docking studies showed that BGG could bind at the active site of TLR4. Finally, in the LPS-driven sepsis mouse model, we showed that pre-treatment with BGG sustained toxic shock, as evident from their 100% survival. Our study clearly showed the therapeutic potential of BGG in toxic shock syndrome.

LC-MS based metabolomics and sensory evaluation reveal the critical compounds of different grades of Huangshan Maofeng green tea

Six grades of Huangshan Maofeng (HSMF) green tea were studied by LC-MS based metabolomics combined with sensory evaluation on bitterness, astringency and sweet aftertaste. Although there was no significant correlation (p > 0.05) between tea grades and the contents of total polyphenols and flavonoids, non-targeted metabolomics revealed that all grades of tea could be classified into two groups, group 1 (T1, T2) and group 2 (T3, 1, 2, 3). The main marker compounds responsible for distinguishing the two groups were procyanidins, flavonoid glycosides, and four hydrolysable tannins, including monogalloyl glucose, digalloyl glucose, trigalloyl glucose and galloyl-hexahydroxydiphenoyl-glucose. The Pearson correlation coefficients of these hydrolysable tannins with HSMF green tea grades were between 0.82 and 0.95. Furthermore, their Pearson correlation coefficients regarding sweet aftertaste were in the range of 0.73–0.83. This study suggested combination of metabolomics and sensory evaluation could provide an insight in searching for more potential taste-active components.

Pharmacological effects of Huangqin Decoction prepared from roots of multi-originated peony on ulcerative colitis in mice:a comparative study

Huangqin Decoction(HQD) is a classic prescription for treating dysentery in the Treatise on Cold Damage and now is mainly used for the treatment of ulcerative colitis(UC). Since there are no requirements on specific Paeonia species, both Paeoniae Radix Alba(white peony root, WPR) and Paeoniae Radix Rubra(red peony root, RPR) are clinically used in HQD now. Although the two types of peony roots are close in origin and similar in primary components, the medicinal properties and efficacies are different. Furthermore, the systematic comparative analysis on the efficacy differences in treating UC of HQD with the roots of multi-originated peony has been seldom reported. This study compared and evaluated the pharmacological effects of HQD prepared from the roots of multi-originated peony, including WPR, RPR-l(derived from P. lactiflora), and RPR-v(derived from P. veitchii) based on the mouse model of UC induced by dextran sodium sulfate(DSS) by animal behaviors, pathological section(colon), and cytokine expression(IL-1β and IL-6), aiming to provide evidence for the identification of the original resource of peony root in HQD. The results indicated that all HQD samples prepared from WPR, RPR-l, and RPR-v could improve the symptoms of UC. Compared with the HQD-WPR, HQD-RPR-l and HQD-RPR-v were significantly different in weight loss, colon length, and disease activity index(DAI) score, but there was no significant difference between HQD-RPR-l and HQD-RPR-v. Moreover, HQD-RPR-v exhibited the most significant improvement in the pathological morphology of colonic tissue and mucosal defects. According to the previous comparative analysis of chemical profiling and content distribution of HQD prepared from the roots of multi-originated peony, RPR-v in HQD was potent in protecting against UC, which was presumedly attributed to a large number of monoterpene glycosides and galloyl glucoses. This study provided a scientific basis for the determination of peony root in HQD and its clinical medication.

Molecular docking analysis of penta galloyl glucose with the bcl-2 family of anti-apoptotic targets.

Apoptosis requires cellular proteins from the B-cell lymphoma 2 (BCL-2) family linked to breast cancer. Therefore, it is of interest to document the Molecular docking analysis data of penta galloyl glucose with the bcl-2 family of anti-apoptotic targets (Bcl-2, BCL-XL, Caspase 3, and Caspase 9). Data shows that Pentagalloyl glucose have optimal binding features with Bcl-2, BCL-XL, Caspase 3, and Caspase 9 proteins with binding energy of -8.6,-7,-7.5 and 4.4 kcal/mol respectively for further consideration in this context.

Polyphenolic profile and ethno pharmacological activities of Callistemonsubulatus (Cheel) Craven leaves cultivated in Egypt

Ethnopharmacological relevanceThe genus Callistemon (syn. Melaleuca) of the myrtle family (Myrtaceae) has been documented as an integral part in the ethnobotanical system of the indigenous people of Australian mainland and many of its islands. Several Callistemons including the species subulatus were used by aboriginal Australians for making rafts, roofs for shelters, bandages, and food recipes, in addition to the management of wounds, infections, pain, cough, bronchitis, and gastrointestinal tract (GIT) disorders. Aim of the studyThe current study is designed to document the therapeutic effect of the aqueous methanolic extract (AME) of C. sabulatus Chell (syn. M. sabulata) leaves in the management of diarrhea and pain. Also, its influence on additional pharmacological modalities that are related to oxidative stress just as skin aging. Ultimately, the polyphenolic profile of the extract is disclosed and correlated to the aforementioned bioactivities. Materials and methodsThe extract was fractionated using various chromatography techniques and the structures of the isolated compounds were determined based on their chemical and spectral data. The antioxidant activity was assessed using multiple models, including 2,2-diphenyl-picrylhydrazyl (DPPH), oxygen radical absorbance capacity (ORAC) and β-carotene bleaching assays. The anti-skin aging effect was evaluated using different relevant enzymatic assays. The antinociceptive activity was investigated using acetic acid-induced writhing, hot plate test, and formalin-induced paw licking in mice models. The antidiarrheal activity was gauge using the castor oil induced diarrhea, enter pooling and gastrointestinal motility in vivo models. ResultsDiverse polyphenols, including quercetin-3-O-β-D-glucuronopyranoside (1), kaempferol-3-O-β-D-glucuronopyranoside (2), strictinin (3), quercetin-3-O-(2``-O-galloyl)-β-D-glucuronopyranoside (4), afzelin (5), di-galloyl glucose (6), mono-galloyl glucose (7), acacetin (8), apigenin-6,7-dimethyl ether (9), kaempferol trimethyl ether (10), dimethoxy chrysin (11), quercetin (12), kaempferol (13), methyl gallate (14), and gallic acid (15) were identified. The extract exhibited as significant antioxidant activity even better than that of Trolox or BHT. Moreover, it exerts elastase, tyrosinase, and collagenase inhibition activities, in addition to the significant peripheral and central analgesic activity in a dose-dependent manner (P < 0.0001). In castor oil induced diarrhea model, AME significantly prolonged the diarrhea onset, decreased the frequency of defecation, and weight of feces. Likewise, it exhibited a significant reduction in the gastrointestinal motility in charcoal meal model (P < 0.0001) and a considerable inhibitory effect on gastrointestinal transit and peristaltic index with all investigated doses (P < 0.0001). ConclusionEthnobotanicals are versatile resources for the management of various ailments by indigenous people and the experimental research is utmost to validate and uncover their pharmacological relevance. C. sabulatus leaves have strong antioxidant, analgesic, anti-skin aging, and antidiarrheal activities which are validated for the first time by various in vitro and in vivo models. The metabolic profile of the unprecedented AME of C. sabulatus leaves compromises a wide array of bioactive polyphenolic metabolites including, flavonoids, tannins, and phenolic acids that are correlated to the observed bioactivities. Altogether, ethnobotanicals with high and diverse contents of polyphenols are potential candidates for the management of various human aliments including neuropathies, GIT disorders, and skin aging conditions.

Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract.

In this study, we present the isolation and characterization of the structure of six gallotannins (1–6), three ellagitannins (7–9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unambiguously determined through nuclear magnetic resonance and circular dichroism analyses. The α-glucosidase activity and glycation inhibitory effects of the isolates were evaluated. Decarboxylated rugosin A (8) showed an α-glucosidase inhibitory activity, while hydrolyzable tannins revealed stronger antiglycation activity than that of the positive control. Furthermore, the identification and quantification of the TBE polyphenols were investigated by high-performance liquid chromatography coupled to ultraviolet detection and electrospray ionization mass spectrometry analysis, indicating the predominance of gallic acid, ellagic acid, and galloyl glucoses showing marked antiglycation properties. These findings suggest that there is a potential food industry application of polyphenols in TBE as a functional food with antidiabetic and antiglycation activities.

Chemical profiling and antidiabetic potency of Paeonia delavayi: Comparison between different parts and constituents

Paeonia delavayi (Paeoniaceae), an endemic plant mainly distributed in southwest China, is always used as the substitute of P. suffruticosa due to their morphological and pharmacological similarity. In the previous study, P. suffruticosa was revealed with antidiabetic potency, whereas the chemical difference and antidiabetic property between different parts of P. delavayi has not yet been studied. This paper was designed to clarify the chemical constituents and antidiabetic potency of P. delavayi by LCMS analysis and enzyme inhibition on α-glucosidase, PTP1B, TCPTP, and DPP4. By interpretation of their UV absorptions and MS fragmentations, and/or comparison with reference samples, 57 constituents comprising 15 flavonoids, 10 monoterpene glycosides, eight triterpenoids, seven galloyl glucoses, six N-containing compounds, five gallic acids, two acetophenones, and four other types of compounds were identified from the different parts of P. delavayi. Moreover, two new monoterpene aglycones (42 and 47) and one new noroleanane triterpenoid (51) were speculated by their MS/MS fragmentation rules. Principal component analysis (PCA) suggested the chemical resemblance between root core and root bark which could be well differentiated with the leaves and stems by their characteristic constituents (monoterpene glycosides, flavonoids, and acetophenones). All the four parts (200 μg/mL) showed obvious inhibition on α-glucosidase and PTP1B (81.2%–98.5%), but moderate to weak inhibition on TCPTP and DPP4 (19.5%–34.9%). Nine compounds representing five main types of constituents in Paeonia plants were assayed for their antidiabetic effects, indicating flavonoids and triterpenoids were the main active substances regarding to the four enzymes. Luteolin displayed obvious activity on α-glucosidase, PTP1B, and TCPTP with IC50 values of 94.6, 136.3, and 157.3 μM, and akebonic acid could inhibit α-glucosidase and PTP1B with IC50 values of 73.5 and 57.8 μM. Luteolin and akebonic acid were recognized as competitive inhibitors of α-glucosidase, but anticompetitive and mix-type inhibitors of PTP1B, respectively. Docking study demonstrated akebonic acid as PTP1B (over TCPTP) selective inhibitor by bonding to the catalytic sites (B/C) of PTP1B. This LCMS combined with enzymatic comparison opens new sights for recognizing the chemical profiles and antidiabetic potency of P. delavayi.

Profiling phenolic compounds in underutilized mango peel by-products from cultivars grown in Spanish subtropical climate over maturation course

Nutraceutical market has undergone an exponential growth worldwide due to its health link-up. With the purpose of evaluating nutraceutical value, the phenolic composition of underutilized mango peel by-products of three cultivars (‘Keitt’, ‘Kent’ and ‘Osteen’) grown in Spanish subtropical climate was monitored at three maturation stages (green, ripe and overripe). Tracking the total phenol content, mango peels were figured out to have until twenty-seven fold higher than edible fraction. Mango peels comprised a wide range of phenolic compounds such as mono- and di-galloyl compounds, gallotannins, phenolic acids, benzophenones and flavonoids. The influence of both factors, cultivar and maturation degree, on the phenolic composition was the main outcome of the research. ‘Keitt’ mango peel was revealed as the cultivar with the highest phenolic content mainly due to the great quantities of galloyl glucose, 5-galloylquinic acid, digalloylquinic acid, hexagalloyl glucose and macluring galloyl glucoside detected. Regarding to the effect of maturation degree, green mango peels showed the highest amounts of polyphenols, although this behaviour could be dependent on the mango cultivar. Therefore, mango peels resulted to be a promising and low-cost resource of phenolic compounds to be exploited in food industry, but to enhance the nutraceutical value, factors such as cultivar and maturation degree should be taken into account.

Partition Coefficients (logP) of Hydrolysable Tannins.

The partition coefficients (logP) between n-octanol and water of 47 purified and characterized hydrolysable tannins were measured with the shake flask method utilizing UPLC and HPLC with UV detection. Results show that galloyl glucoses and gallotannins are clearly more hydrophobic than ellagitannins but the differences in hydrophobicity within ellagitannins are more varied than within galloyl glucoses or gallotannins. Most notable structural features that were found to influence the hydrophobicity of ellagitannins were the number of free galloyl groups, acyclic versus cyclic polyol, substitution of the anomeric position of glucose and 4C1 versus 1C4 conformation of the glucopyranose core.

The Mastic Tree (Pistacia lentiscus L.) Leaves as Source of BACs: Effect of Growing Location, Phenological Stage and Extraction Solvent on Phenolic Content.

SUMMARYResearch backgroundMastic tree (Pistacia lentiscus L.) of the Anacardiaceae family is an evergreen shrub from Mediterranean countries where it is used in traditional medicine. Analysis of P. lentiscus leaf, stem, fruit and root extracts showed high concentrations of principal groups of secondary metabolites (flavonoids, phenolic acids and tannins), suggesting the plant possesses great biological potential. Therefore, the aim of this research is to evaluate the impact of environmental parameters and the extraction solvent type on the concentration of phenols in mastic tree leaf extracts grown at four different locations along the Adriatic coast (Barbariga, Lun, Hvar and Vela Luka) during three phenological stages (early flowering, early fruiting and late fruiting).Experimental approachSince mastic tree plant has phenolic compounds with different structures and chemical properties, ethanolic and methanolic leaf extracts were analysed using high-performance liquid chromatography (HPLC) coupled with UV/Vis PDA detector. Phenolic compounds were identified by comparing the retention times and spectral data with those of standards at 280 and 340 nm.Results and conclusionsIn all samples, phenolic acids and flavonol glycosides were quantified, while catechin was quantified only in methanolic extracts. The 5-O-galloylquinic acid was determined as a predominant phenolic compound in all samples followed by monogalloyl glucose, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid and gallic acid, respectively. Myricetin-3-O-rhamnoside was found to be the predominant flavonol glycoside followed by myricetin-3-O-glucoside, myricetin-3-O-glucuronide, quercetin-3-O-rhamnoside and derivative of flavonol glycoside. The mass concentration of these compounds significantly varied during different phenological stages, at different growing locations and used extraction solvents. The highest phenolic mass concentration was determined in the samples harvested at Hvar growing location and extracted in 80% methanol. The highest total phenolic acid mass concentration was obtained in the samples harvested during the flowering phenological stage and the highest total flavonoid mass concentration in the samples harvested during the early fruiting stage.Novelty and scientific contributionThe obtained data provide a better understanding of the P. lentiscus species phenolic concentration, which can lead to further investigations regarding the valorisation of mastic tree leaves as pharmaceutical products or as food products with added value.

Terminalia bellirica (Gaertn.) roxb. (Bahera) in health and disease: A systematic and comprehensive review

BackgroundTerminalia 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. PurposeThe 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. MethodsPubMed, 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. ResultsA 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. ConclusionPreclinical 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.

Inducing Plant Defense Reactions in Tobacco Plants with Phenolic-Rich Extracts from Red Maple Leaves: A Characterization of Main Active Ingredients

Red maple leaf extracts (RME) were tested for their plant defense inducer (PDI) properties. Two extracts were obtained and compared by different approaches: RME1 using ethanol–water (30–70%, v/v, 0.5% HCl 1N) and RME2 using pure water. Both extracts titrated at 1.9 g L−1 in polyphenols and infiltrated into tobacco leaves efficiently induced hypersensitive reaction-like lesions with topical accumulation of auto-fluorescent compounds noted under UV and scopoletin titration assays. The antimicrobial marker PR1, β−1,3-glucanase PR2, chitinase PR3, and osmotin PR5 target genes were all upregulated in tobacco leaves following RME1 treatment. The alkaline hydrolysis of RME1 and RME2 combined with HPLC titration of gallic acid revealed that gallate functions were present in both extracts at levels comprised between 185 and 318 mg L−1. HPLC-HR-MS analyses and glucose assay identified four gallate derivatives consisting of a glucose core linked to 5, 6, 7, and 8 gallate groups. These four galloyl glucoses possessed around 46% of total gallate functions. Their higher concentration in RME suggested that they may contribute significantly to PDI activity. These findings define the friendly galloyl glucose as a PDI and highlight a relevant methodology for combining plant assays and chemistry process to their potential quantification in crude natural extracts.

LC-MS Profile, Gastrointestinal and Gut Microbiota Stability and Antioxidant Activity of Rhodiola rosea Herb Metabolites: A Comparative Study with Subterranean Organs.

Golden root (Rhodiola rosea L., Crassulaceae) is a famous medical plant with a one-sided history of scientific interest in the roots and rhizomes as sources of bioactive compounds, unlike the herb, which has not been studied extensively. To address this deficiency, we used high-performance liquid chromatography with diode array and electrospray triple quadrupole mass detection for comparative qualitative and quantitative analysis of the metabolic profiles of Rhodiola rosea organs before and after gastrointestinal digestion in simulated conditions together with various biochemical assays to determine antioxidant properties of the extracts and selected compounds. R. rosea organs showed 146 compounds, including galloyl O-glucosides, catechins, procyanidins, simple phenolics, phenethyl alcohol derivatives, (hydroxy)cinnamates, hydroxynitrile glucosides, monoterpene O-glucosides, and flavonol O-glycosides, most of them for the first time in the species. The organ-specific distribution of compounds found for catechins, procyanidins, and cinnamyl alcohols and glucosides was typical for underground organs and flavonoids and galloylated glucoses concentrated in the herb. Extracts from rhizomes, leaves and flowers showed high phenolic content and were effective scavengers of free radicals (2,2-diphenyl-1-picrylhydrazyl (DPPH•), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+), O2•−, •OH) and protected β-carotene in a bleaching assay. Digestion in the gastric and intestine phase influenced the composition of R. rosea extracts negatively, affecting the content of catechins, procyanidins, and galloyl glucoses, and therefore, the antioxidativity level. After gut microbiota treatment, the antioxidant capacity of rhizome extract was lower than leaves and flowers due to the aglycone composition found in the colonic phase of digestion. Our study demonstrated that the herb of R. rosea is a rich source of metabolites with high antioxidant properties and could be a valuable plant for new bioactive products.

Antibacterial and anti-inflammatory activity of bistort (Bistorta officinalis) aqueous extract and its major components. Justification of the usage of the medicinal plant material as a traditional topical agent

Ethnopharmacological relevanceBistort rhizome (Bistorta officinalis) is a traditionally used plant material popular in Europe and Asia in the treatment of diarrhea and as a topical agent for skin conditions. It contains tannins mostly condensed flavan-3-ol derivatives. However, the in-depth phytochemical investigation of infusions from this plant materials is still lacking. Additionally, the scientific reports supporting the traditional topical application of bistort rhizome are scarce. Aim of the studyThe major objective of the present study was to comprehensively investigate the chemical composition of infusion from subterranean parts of common bistort both using hyphenated chromatographic technique and isolation approach. Additionally, the influence of water extract on pro-inflammatory functions of human neutrophils was performed. As bacterial infections play a crucial role in the generation of skin inflammations the antimicrobial activity of the infusion and its major components was established. Material and methodsThe chemical composition of the infusion was established using UHPLC-DAD-MS3 method. Major compounds which could not be identified using chromatographic analysis were isolated by column chromatography and preparative HPLC. Obtained pure phytochemicals were identified by NMR analysis. The influence of the extract and compounds on the cell viability and apoptosis was evaluated by flow cytometry. The release of pro-inflammatory cytokines after LPS stimulation was established by ELISA. Finally, the antimicrobial assays were performed by establishing MIC and MBC values using several bacterial strains. ResultsThe UHPLC analysis revealed the infusion contained mainly, galloyl glucose derivatives, procyanidins and chlorogenic acid. Several compounds were isolated and identified for the first time from the investigated plant material. It was shown that the infusion and its constituents influenced the release of proinflammatory cytokines such as IL-1β, TNF-α and IL-8 and also affected the viability and apoptosis of healthy cells. Both extract and isolated natural products displayed antimicrobial activity against skin pathogens. ConclusionsThe results obtained in the present study support that the infusions from common bistort influence key biological processes are crucial for skin conditions with the inflammatory background. The study justifies the traditional topical application of common bistort.