Nowadays, secondary raw materials (SRM) obtained from plant matrices are of great interest for circular economy, suitable for sustainable measures to reduce environmental impact. This work focused on the extraction, characterization and quantification of compounds obtained from leaves and fruits of the Sicilian sumac, Rhus coriaria L. and their application as natural dyes on textile fibres. Extractions were performed with Extractor Naviglio®, maceration and ultrasound assisted methods and food-grade solvents (aqueous and hydroalcoholic) to evaluate the yields for dye compounds. The presence of colouring molecules was evaluated by UV-Vis spectrophotometer, and the extracts selected for colouring were quantified and characterized by LC-MS. The results showed that Extractor Naviglio® achieved the best extraction yield, and the ethanol-water mixture extracts had a higher amount of total phenolic compounds (TPC) and a higher content of total colouring compounds (TCC). These extracts were selected for subsequent applications as dyes for linen, cotton and wool. The chemical profile of selected extracts was rich in compounds such as gallotannin and anthocyanin class. Fibre dyeing was verified by recording CIELAB colouring coordinates. The results suggest that the dyes obtained from R. coriaria can be of great interest for artisanal and industrial processes, in accordance with environmental sustainability.

Rhus chinensis Mill., an economically valuable Anacardiaceae species, is parasitized by the galling aphid Schlechtendalia chinensis, resulting in the formation of the Chinese gallnut (CG). Here, we report a chromosomal-level genome assembly of R. chinensis, with a total size of 389.40 Mb and scaffold N50 of 23.02 Mb. Comparative genomic and transcriptome analysis revealed that the enhanced structure of CG and nutritional metabolism contribute to improving the adaptability of R. chinensis to S. chinensis by supporting CG and galling aphid growth. CG was observed to be abundant in hydrolysable tannins (HT), particularly gallotannin and its isomers. Tandem repeat clusters of dehydroquinate dehydratase/shikimate dehydrogenase (DQD/SDH) and serine carboxypeptidase-like (SCPL) and their homologs involved in HT production were determined as specific to HT-rich species. The functional differentiation of DQD/SDH tandem duplicate genes and the significant contraction in the phenylalanine ammonia-lyase (PAL) gene family contributed to the accumulation of gallic acid and HT while minimizing the production of shikimic acid, flavonoids, and condensed tannins in CG. Furthermore, we identified one UDP glucosyltransferase (UGT84A), three carboxylesterase (CXE), and six SCPL genes from conserved tandem repeat clusters that are involved in gallotannin biosynthesis and hydrolysis in CG. We then constructed a regulatory network of these genes based on co-expression and transcription factor motif analysis. Our findings provide a genomic resource for the exploration of the underlying mechanisms of plant-galling insect interaction and highlight the importance of the functional divergence of tandem duplicate genes in the accumulation of secondary metabolites.

Twenty oenotannins from different botanical origins were studied in model wine solution (1 g/L, 12% ethanol, pH 3.5). An original device was created for measuring Oxidation-Reduction potential (ORp) of the solutions at 20 °C in strict anoxic condition by the electrochemical method of the platinum electrode zero-current potential. Reactivity against proteins and antioxidant properties were related to the chemical structure and, consequently, to the botanical origin of the oenotannins. The highest turbidity after BSA addition (ΔNTU > 1000) values were measured for the gallic hydrolysable tannins. The ORp versus standard hydrogen electrode ranged from 420 to 260 mV. The ellagitannins had the highest antioxidant power (AP%), followed by condensed tannins and gallotannins, highlighting a correlation with the phenolic profile. Based on these findings, two formulations were prepared as a blend of some of the tested oenotannins, with the ability to increase (MIX1) and decrease (MIX2) the ORp of the model wine.

Pentagalloyl glucose (PGG) is a natural hydrolyzable gallotannin abundant in various plants and herbs. It has a broad range of biological activities, specifically anticancer activities, and numerous molecular targets. Despite multiple studies available on the pharmacological action of PGG, the molecular mechanisms underlying the anticancer effects of PGG are unclear. Here, we have critically reviewed the natural sources of PGG, its anticancer properties, and underlying mechanisms of action. We found that multiple natural sources of PGG are available, and the existing production technology is sufficient to produce large quantities of the required product. Three plants (or their parts) with maximum PGG content were Rhus chinensis Mill, Bouea macrophylla seed, and Mangifera indica kernel. PGG acts on multiple molecular targets and signaling pathways associated with the hallmarks of cancer to inhibit growth, angiogenesis, and metastasis of several cancers. Moreover, PGG can enhance the efficacy of chemotherapy and radiotherapy by modulating various cancer-associated pathways. Therefore, PGG can be used for treating different human cancers; nevertheless, the data on the pharmacokinetics and safety profile of PGG are limited, and further studies are essential to define the clinical use of PGG in cancer therapies.

Chitosan functionalization is a growing field of interest to enhance the unique characteristics of metal oxide nanoparticles. In this study, a facile synthesis method has been used to develop a gallotannin loaded chitosan/zinc oxide (CS/ZnO) nanocomposite. Initially, white color formation confirmed the formation, and physico-chemical natures of the prepared nanocomposite were examined using X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) coupled with energy dispersive spectroscopy (EDS), and transmission electron microscopy (TEM). Crystalline of CS amorphous phase and ZnO patterns were demonstrated by XRD. FTIR revealed the presence of CS and gallotannin bio-active groups in the formed nanocomposite. Electron microscopy study exhibited that the produced nanocomposite had an agglomerated sheets like morphology with an average size of 50-130 nm. Further, the produced nanocomposite was evaluated for methylene blue (MB) degradation activity from aqueous solution. After 30 min of irradiation, the efficiency of nanocomposite degradation was found to be 96.64 %. Moreover, prepared nanocomposite showed a potential and concentration-dependent antibacterial activity against S. aureus. In conclusion, our findings demonstrated that prepared nanocomposite can be used as an excellent photocatalyst as well as a bactericidal agent in industrial and clinical sectors.

Smilax sieboldii, a climbing tree belonging to Smilacaceae, has been used in traditional oriental medicine for treating arthritis, tumors, leprosy, psoriasis, and lumbago. To evaluate the anti-obesity effects of S. sieboldii (Smilacaceae), we screened methylene chloride (CH2Cl2), ethyl acetate (EtOAc), aqueous-saturated n-butanol, and ethanol (EtOH) extracts of the whole plant at various concentrations to inhibit adipogenesis in adipocytes. The 3T3-L1 cell line with Oil red O staining with the help of fluorometry was used as an indicator of anti-obesity activity. Bioactivity-guided fractionation of the EtOH extract and subsequent phytochemical investigation of the active CH2Cl2- and EtOAc-soluble fractions resulted in the isolation of 19 secondary metabolites (1-19), including a new α-hydroxy acid derivative (16) and two new lanostane-type triterpenoids (17 and 18). The structures of these compounds were characterized using various spectroscopic methods. All the isolated compounds were screened for adipogenesis inhibition at a concentration of 100 μM. Of these, compounds 1, 2, 4-9, 15, and 19 significantly reduced fat accumulation in 3T3-L1 adipocytes, especially compounds 4, 7, 9, and 19, showing 37.05 ± 0.95, 8.60 ± 0.41 15.82 ± 1.23, and 17.73 ± 1.28% lipid content, respectively, at a concentration of 100 μM. These findings provide experimental evidence that isolates from S. sieboldii extracts exert beneficial effects regarding the regulation of adipocyte differentiation.

Nonalcoholic fatty liver disease (NAFLD) is a worldwide prevalent chronic liver disease characterized by hepatic steatosis. Water caltrop, the fruit of Trapa natan, is widely cultivated as an edible vegetable in Asian countries. In China, water caltrop pericarp has long been used as a functional food to treat metabolic syndrome, yet the bioactive substances and their pharmacological mechanisms remain unclear. In this study, a natural gallotannin, 1,2,3,6-tetra-O-galloyl-β-D-glucopyranoside (GA), was isolated from water caltrop pericarp and evaluated for its therapeutic effect on NAFLD. Treatment of GA (15 and 30 mg/kg/day) suppressed the body weight gain (p < 0.001) and ameliorated lipid deposition (p < 0.001) in high-fat diet (HFD)-induced NAFLD mice. GA was able to alleviate HFD-induced insulin resistance (p < 0.001), oxidative stress (p < 0.001), and inflammation (p < 0.001), thereby restoring the liver function in HFD-induced NAFLD mice. Mechanistically, GA diminished the aberrant signaling pathways including AMPK/SREBP/ACC, IRs-1/Akt, IKK/IκB/NF-κB in HFD-induced NAFLD mice and modified gut microbiota dysbiosis in these mice as well. The current findings suggest that GA is a promising novel agent for NAFLD therapy.

Phytochemical is considered an alternative method for cyanobacterial bloom control in aquatic environments. When cyanobacteria are treated with anti-algal materials produced from plant tissues, they tend to exhibit growth inhibition or necrosis of cells. These different anti-algal responses have not been well discussed, and thus, the modes of anti-algal action in cyanobacteria remain obscure. In this study, transcriptomic and biochemical researches were conducted to understand the mechanisms of cyanobacterial growth inhibition and necrosis in harmful cyanobacterial cells exposed to allelopathic materials. The cyanobacteria Microcystis aeruginosa was treated with aqueous extracts of walnut husk, rose leaf, and kudzu leaf. Walnut husk and rose leaf extracts induced mortality of cyanobacterial population with cell necrosis, whereas kudzu leaf extract exhibited poorly grown cells with shrunk size. Through RNA sequencing, it was revealed that the necrotic extracts significantly downregulated critical genes in enzymatic chain reactions for carbohydrate assembly in the carbon fixation cycle and peptidoglycan synthesis. Compared to the necrotic extract treatment, expression of several genes related to DNA repair, carbon fixation, and cell reproduction was less interrupted by the kudzu leaf extract. Biochemical analysis of cyanobacterial regrowth was performed using gallotannin and robinin. Gallotannin was identified as the major anti-algal compound in walnut husk and rose leaf affecting cyanobacterial necrosis, whereas robinin, which is the typical chemical in kudzu leaf, was associated with growth inhibition of cyanobacterial cells. These combinational studies using RNA sequencing and regrowth assays provided evidence supporting the allelopathic effects of plant-derived materials on cyanobacterial control. Furthermore, our findings suggest novel algicidal scenarios with different responses in the cyanobacterial cells depending on the type of anti-algal compounds.

BACKGROUND: Algal infestation in Korean lakes, rivers, and in agroecosystems is a catastrophic problem resulting in contaminated drinking and agricultural irrigation water. Developing allelochemical-based algicides has previously faced difficulties, including dosage requirements and chemical instability. Despite these challenges, these algicides have enormous potential for eco-friendly use. This study presents the efficient use of tannin derivatives as antialgal chemicals modeled on a tannin-rich stem extract of Rhus chinensis in a thermal processing application.
RESULTS: Tannic acids are the key component of algal necrosis in R. chinensis stem extract, and although heat extraction from the stem increased the crude extraction yield 1.8-fold, the procedure induced the conversion of tannic acids to gallic acid, resulting in lower antialgal activity. Gallotannin showed stronger antialgal activity (The 50% lethal dosage (LD50 )= 44.6 mg L-1 ) than gallic acid (LD50  = 99.2 mg L-1 ), and the nonheated extract exhibited 3.7-fold lower LD50 (0.66 g L-1 ) than the heated extract (LD50  = 2.45 g L-1 ), resulting in 2.6-fold higher content of gallotannin.
CONCLUSIONS: These results demonstrate that heat treatment of R. chinensis stems during the extraction process is not beneficial to algal control because of the acceleration of thermal tannin degradation, despite it showing higher crude extract yields. Therefore, it is suggested extraction processes minimizing the loss of tannic acids should be the preferred methods used to develop tannin-based natural algicides for controlling algal infestation. Tannic acids showed higher toxicity into necrosis of M. aeruginosa than gallic acid where heat-processed extraction of R. chinensis stems produces more gallic acid content resulting in thermal degradation of tannic complexes than the extraction of nonthermal treatment. © 2022 Society of Chemical Industry.

A phytochemical investigation of the roots of Euphorbia fischeriana Steud. led to the isolation of eleven undescribed gallotannins, fishertannins A-K, together with four known analogues. Their structures were elucidated by the comprehensive spectroscopic data including UV, IR, HR-ESI-MS, and NMR, while the absolute configurations of the sugar moiety were determined by the acid hydrolysis and HPLC analyses. Fishertannin A possessed an unusual skeleton comprised of acetophenone, galloyl group, arabinofuranosyl and glucopyranosyl moieties. Fishertannin B, fishertannin H, fishertannin K, 1,2,3-tri-O-galloyl-β-D-glucopyranose, 3,4,6-tri-O-galloyl-D-glucopyranose, and 1,6-di-O-galloyl-β-D-glucopyranose displayed the potent α-glucosidase inhibitory activities with the IC50 values of 15.48-177.13 μM. Examination of the structure-activity relationships (SAR) demonstrated that the galloyl and glucopyranosyl moieties played a key role in the inhibitory activity for both α-glucosidase and α-amylase inhibitory activity. Among all isolates, 1,2,3-tri-O-galloyl-β-D-glucopyranose showed the most potent and highly specific inhibitory activity against α-glucosidase with an IC50 value of 15.48 ± 0.60 μM. The kinetic analysis of 1,2,3-tri-O-galloyl-β-D-glucopyranose disclosed the mixed inhibition type on α-glucosidase, and the molecular docking visualized the stable binding with the catalytic pocket of α-glucosidase (pdb 3A4A). These findings indicated the excellent antidiabetic potential of the gallotannins from E. fischeriana, while 1,2,3-tri-O-galloyl-β-D-glucopyranose could be developed as a promising candidate for the treatment of T2DM with fewer side effects.