Search

Leucas zeylanicais one of the most precious gifts of nature to the entire civilization. It offers folkloric system a dependable option to heal numerous diseases like- burning urination, toothaches, common skin diseases, gout, inflammatory conditions, rheumatic diseases, abdominal pain, worms, anorexia, colic, flatulence, etc. Many of these ancient practices have got their scientific resemblances like- using as an agent for treating common pains, oxidative stresses, microbial infections, sleep disorders, inflammations, gout associated pains, thrombosis and sunlight related skin damages. Some researchers also isolated a huge bunch of vital phytochemicals like- torosaflavone A, drymariatin C, daidzein, luteolin 3′,4′-dimethyl ether, apigenin, tricin, chrysoeriol, linarigenin, β-sitosterol, stigmasterol, hexadecanoic acid, octadecanoic acid, 9,12,15- octadecatrienoic acid, farnesene, β-caryophyllene, caryophyllene oxide, phytol, β-cubebene, α-selinene, α-tocopherol etc. from different crude extracts ofLeucas zeylanica. Making proper correlation between these phytoconstituents with the general utilizations of this plant will assist scientists to develop auspicious lead compounds. This review covers a summary of ethnomedicinal, phytochemical and biological studies of several crude preparations ofLeucas zeylanica.

The brown planthopper (BPH), Nilaparvata lugens, is an important pest that affects rice (Oryza sativa) production in Asia. The flavone tricin (5,7,4ʹ-trihydroxy-3ʹ,5ʹ-dimethoxy flavone) is a valuable secondary metabolite commonly found in rice plants that can defend rice plants against infestation by BPH. BPH damage can reduce the metabolic level of tricin in rice. Our preliminary transcriptome research results showed that BPH salivary protein 7, NlSP7, is highly responsive to tricin stimuli. However, the function of NlSP7 in mediating the interaction between the rice plant and the BPH is unknown. In this study, we cloned the NlSP7 gene in N. lugens and found that its mRNA level was greater in the presence of high tricin content than low tricin content, regardless of whether the BPHs were fed a rice plant diet or an artificial diet containing 100 mg/L tricin. Knocking down NlSP7 resulted in BPH individuals spending more time in the non-penetration and pathway phase, and less time feeding on the phloem of rice plants. These changes decreased BPH food intake, feeding behavior, and fitness, as well as the tricin content of the rice plants. These findings demonstrate that the salivary protein NlSP7 of BPH functions as an effector for tricin metabolism in rice.

Agriophyllum squarrosum (L.) Moq., a pioneer plant endemic to the temperate deserts of Asia, could be domesticated into an ideal crop with outstanding ecological and medicinal characteristics. A previous study showed differential flavonoid accumulation between two in situ altitudinal ecotypes. To verify whether this accumulation was determined by environmental or genetic factors, we conducted flavonoid-targeted metabolic profiling among 14 populations of A. squarrosum collected from regions with different altitudes based on a common garden experiment. Results showed that the most abundant flavonoid in A. squarrosum was isorhamnetin (48.40%, 557.45 μg/g), followed by quercetin (13.04%, 150.15 μg/g), tricin (11.17%, 128.70 μg/g), isoquercitrin (7.59%, 87.42 μg/g), isovitexin (7.20%, 82.94 μg/g), and rutin (7.00%, 80.62 μg/g). However, based on a common garden at middle-altitude environment, almost none of the flavonoids was enriched in the high-altitude populations, and even some flavonoids, such as quercetin, tricin, and rutin, were significantly enriched in low-altitude populations. This phenomenon indicated that the accumulation of flavonoids was not a result of local adaptation to high altitude. Furthermore, association analysis with in situ environmental variables showed that the contents of quercetin, tricin, and rutin were strongly positively correlated with latitude, longitude, and precipitation gradients and negatively correlated with temperature gradients. Thus, we could conclude that the accumulations of flavonoids in A. squarrosum were more likely as a result of local adaption to environmental heterogeneity combined with precipitation and temperature other than high altitude. This study not only provides an example to understand the molecular ecological basis of pharmacognosy, but also supplies methodologies for developing a new industrial crop with ecological and agricultural importance.

Tricin, one of the flavones present in edible Poaceae species, was shown to interfere with intestinal inflammatory-related carcinogenesis and suppress metastasis in colon cancer mice models. Those botanical foods and medicinal herbs which contain high content of tricin may be considered as health supplements for colon health. Hence, the present study aimed to identify and quantify the content of tricin in various medicinal herbs, edible botanicals and some agricultural by-products by LC-MS. A list of “top 10 tricin-rich botanicals/medicinal herbs” was built. From the results, the top three high tricin content botanicals are the dried culms of Triticum aestivum (wheat straw), dried culms of Oryza sativa (rice straw) and mature fruits of Imperata cylindrica. Furthermore, a simple, straightforward isolation method has been developed to isolate tricin from wheat straw which achieved 50% isolation rate (percentage yield of 0.05% w/w) with purity of not less than 98%.

Lignocellulose, the structural component of plant cells, is a major agricultural byproduct and the most abundant terrestrial source of biopolymers on Earth. The complex and insoluble nature of lignocellulose limits its conversion into value-added commodities, and currently, efficient transformation requires expensive pretreatments and high loadings of enzymes. Here, we report on a fungus from the Parascedosporium genus, isolated from a wheat-straw composting community, that secretes a large and diverse array of carbohydrate-active enzymes (CAZymes) when grown on lignocellulosic substrates. We describe an oxidase activity that cleaves the major β-ether units in lignin, thereby releasing the flavonoid tricin from monocot lignin and enhancing the digestion of lignocellulose by polysaccharidase mixtures. We show that the enzyme, which holds potential for the biorefining industry, is widely distributed among lignocellulose-degrading fungi from the Sordariomycetes phylum.

Investigation of the chemical constituents of Salvia judaica growing wild in Jordan led to the isolation and identification of 15 known compounds. These included: luteolin-3'-methyl ether (1), indole-3-carboxyaldehyde (2), p-hydroxybenzaldehyde (3), tricin (4), apigenin (5), methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (6), methyl rosmarinate (7), rosmarinic acid (8), salvigenin (9), β-sitosterol (10), 3β, 28-dihydroxyurs-12-ene (11), cirsilineol (12), 2,3-dihydroxyurs-12-en-28-oic acid (13), β-sitosteryl glucoside (14), and tormentic acid (15). Compounds 6 and 7 exhibited strong radical scavenging and chelating activities as compared to α-tocopherol and ascorbic acid, compound 7 showed a 2-fold greater antioxidant activity as compared to compound 6. Furthermore, low doses of compounds 6 and 7 were able to inhibit the growth of leukemic (HL-60, Jurkat, K562 and CCRF-SB) and solid tumor cells (MCF-7, MDA-MB-231 and Caco-2). Compound 7 showed a ca. 3-4-fold stronger cytotoxicity against the tested cells as compared to compound 6.

Non-centrifugal sugar product (NCS) is produced without molasses removal and contains nutrients and phytochemicals inherently found in sugarcane. To obtain a high-quality product, clarifying raw cane juice, especially following the traditional process, is the most important step to remove contamination as insoluble and suspended matter impurities from the rind during harvesting and pressing. Calcium oxide (CaO) is a promising chemical, widely used as a liming agent to clarify raw juice by the traditional non-centrifugal sugar process. However, use of traditional methods and different cane cultivars affect the quality of sugar products. Clarification by calcium oxide at different pH levels and the diversity of cane cultivars also affect physicochemical components. Bioactive compounds among the obtained products were evaluated. Clarifying juice at pH 8.5 gave highest insoluble solids (47.52 g) removed from cane juice and lowest sediment value (0.68%) of non-centrifugal sugar but caused greatest loss of policosanol and tricin contents. Using calcium oxide clarification, Suphanburi 50 cultivar gave NCS with the highest sugar yield (17.75%) but lowest color value (2100 IU) and phytochemical contents. LK 92-11 cane cultivar produced NCS with the highest color value (6533.3 IU), total phenolic content (1124.09 mg GAE/100 g), total flavonoid content (143.82 mg RUE/100 g), policosanol content (4.13 mg/100 g) and tricin content (50.82 µg/100 g).

Purpose: Discovering new antimyocardial ischemia drug candidates that are highly efficient, have low toxicity, and originate from natural products is a popular trend for new cardiovascular drug development at present. The ethanol extract of Livistona chinensis leaves showed a favorable antioxidant activity in our preliminary screening test. This study aims to screen out antioxidants from the herb leaves further and evaluate their efficacy in acute myocardial ischemia treatment at the cellular level. Materials and methods: Guided with online 1, 1-diphenyl-2-picrylhydrazyl (DPPH)-high-performance liquid chromatography (HPLC) screening, antioxidants were first separated and isolated from the ethanol extract of L. chinensis leaves by preparative-HPLC. Subsequently, offline DPPH approach was used to validate the free radical scavenging activity of the components. Ultimately, the resulting antioxidants were evaluated against the hypoxia/reoxygenation (H/R)-, H2O2-, or adriamycin (ADM)-induced injury in H9c2 cells to verify their cardioprotective effects in vitro. Results: Five antioxidant ingredients, namely, orientin, isoorientin, vitexin, isovitexin, and tricin, were quickly distinguished and isolated from L. chinensis leaves. The IC50 values of these ingredients were further examined by offline DPPH assay, as follows: 15.51±0.22, 6.64±0.38, 11.86±0.24, 8.89±0.66, and 31.86±0.24 μg/mL, respectively. Out of these ingredients, isoorientin showed the strongest antioxidation, which was equivalent to that of the positive control drug (vitamin C, IC50: 6.99±0.62 μg/mL). Using H/R-, H2O2-, and ADM-induced H9c2 cell injury models, the five ingredients had different extents of cardioprotective effects in vitro. In particular, isoorientin showed the strongest protection. All the five ingredients also showed insignificant cytotoxic effect to normal H9c2 cells. Conclusion: The ethanol extract of L. chinensis leaves contained five antioxidants with low cardiac cytotoxicity. Isoorientin possessed the strongest antioxidation, which can predominantly account for the myocardial protection effects within the extract.

In rice (Oryza sativa), OsF2H and OsFNSII direct flavanones to independent pathways that form soluble flavone C-glycosides and tricin-type metabolites (both soluble and lignin-bound), respectively. Production of soluble tricin metabolites requires CYP75B4 as a chrysoeriol 5'-hydroxylase. Meanwhile, the close homologue CYP75B3 is a canonical flavonoid 3'-hydroxylase (F3'H). However, their precise roles in the biosynthesis of soluble flavone C-glycosides and tricin-lignins in cell walls remain unknown. We examined CYP75B3 and CYP75B4 expression in vegetative tissues, analyzed extractable flavonoid profiles, cell wall structure and digestibility of their mutants, and investigated catalytic activities of CYP75B4 orthologues in grasses. CYP75B3 and CYP75B4 showed co-expression patterns with OsF2H and OsFNSII, respectively. CYP75B3 is the sole F3'H in flavone C-glycosides biosynthesis, whereas CYP75B4 alone provides sufficient 3',5'-hydroxylation for tricin-lignin deposition. CYP75B4 mutation results in production of apigenin-incorporated lignin and enhancement of cell wall digestibility. Moreover, tricin pathway-specific 3',5'-hydroxylation activities are conserved in sorghum CYP75B97 and switchgrass CYP75B11. CYP75B3 and CYP75B4 represent two different pathway-specific enzymes recruited together with OsF2H and OsFNSII, respectively. Interestingly, the OsF2H-CYP75B3 and OsFNSII-CYP75B4 pairs appear to be conserved in grasses. Finally, manipulation of tricin biosynthesis through CYP75B4 orthologues can be a promising strategy to improve digestibility of grass biomass for biofuel and biomaterial production.

Breeding approaches to enrich lignins in biomass could be beneficial to improving the biorefinery process because lignins increase biomass heating value and represent a potent source of valuable aromatic chemicals. However, despite the fact that grasses are promising lignocellulose feedstocks, limited information is yet available for molecular-breeding approaches to upregulate lignin biosynthesis in grass species. In this study, we generated lignin-enriched transgenic rice (Oryza sativa), a model grass species, via targeted mutagenesis of the transcriptional repressor OsMYB108 using CRISPR/Cas9-mediated genome editing. The OsMYB108-knockout rice mutants displayed increased expressions of lignin biosynthetic genes and enhanced lignin deposition in culm cell walls. Chemical and two-dimensional nuclear magnetic resonance (NMR) analyses revealed that the mutant cell walls were preferentially enriched in γ-p-coumaroylated and tricin lignin units, both of which are typical and unique components in grass lignins. NMR analysis also showed that the relative abundances of major lignin linkage types were altered in the OsMYB108 mutants.

This study was undertaken to determine the effects of enzyme-treated Zizania latifolia (ETZL) and of its major compound tricin on skin photo-aging and to investigate the mechanisms involved. It was found ETZL and tricin suppressed matrix metalloproteinase (MMP) production and increased type I-procollagen production in UVB-irradiated human dermal fibroblasts (HDFs). Furthermore, ETZL and tricin significantly up-regulated the expressions of the antioxidant enzymes HO-1 and SOD1, reduced UVB-induced reactive oxygen species (ROS) generation and mitogen-activated protein kinase (MAPK) induction by ROS and thereby attenuated activator protein-1 (AP-1) expression. In addition, ETZL and tricin both reduced the phosphorylations of IκBα and IKKα/ß and κB blocked the nuclear translocation of nuclear factor-κB (NF-κB) p65. These results show that ETZL have skin protective effects against UVB and suggest tricin as major efficacious material in ETZL protecting skin photoaging.

Synergistic fungal pretreatment involving white-rot and brown-rot fugal pretreatment has shown great potential for enhancing the yield of sugars from biomass time-effectively and environmentally benign. In this work, the effects of this integrated fungal pretreatment on lignin characteristics and thermal behavior of corncob were examined in the view of whole plant valorization. The results show that an efficient deconstruction of lignin was achieved by white-rot fungus, and subsequent brown-rot fungus promoted the preferential breakdown of guaiacyl units, further enhancing lignin extraction efficiency (62.3%). Consequently, less phenolic hydroxyl, methoxyl, tricin, ester-linked p-coumaric acid, more carboxylic acid, ratio of syringyl to guaiacyl units, β-O-4' linkage and molecular weight were found in W-BL. Thermal stability was improved and the increased phenol and alkyl-phenols contents in pyrolysis products demonstrated that synergistic fungal pretreatment definitely improved the lignin oil quality. These discoveries provide new insights into set strategy for microbial screening, pretreatment and lignin processing.

Some errors were discovered relating to the published equation coefficients of Cheng and co-workers [J. Chem. Thermodyn. 89 (2015) 89–92] for mathematically describing the solubility behaviour of tricin in water and ethanol mixtures using the modified Apelblat equation and λh equation. There was large difference between the back-calculated solubilities using the published equation coefficients and the mole fraction values as stated in the published paper for the two models. Additionally, the preferential solvation parameters (δx1,3) of tricin in the solvent mixture of ethanol (1) + water (2) were derived from their available solubility data using the inverse Kirkwood–Buff integrals method. Within the composition 0.25

To understand the lignocellulose properties of sugarcane (Saccharum sp.) bagasse with a view to its application to produce fermentable sugars, we comparatively analyzed lignocellulose properties, especially lignin chemical structures, of bagasse before and after alkaline, hydrothermal, and dilute sulfuric acid pretreatments. Wet chemical analyses and two-dimensional nuclear magnetic resonance spectroscopy determined that lignocellulose from untreated bagasse contained similar levels of guaiacyl (G) and syringyl (S) lignins with lower levels of p-hydroxyphenyl (H) and tricin (T) lignins. Alkaline pretreatment preferentially removed S and T lignins from bagasse, whereas the hydrothermal and dilute sulfuric acid pretreatments had the effect of enriching lignins (except T lignin) by reducing xylans and arabinans. Our data indicated that the alkaline and dilute sulfuric acid pretreatments relatively enriched β–5 linkages, while reducing β–O–4 and β–β substructures, in the residual lignin polymers. In contrast, hydrothermal pretreatment reduced all three major linkage types.

Sasa quelpaertensis Nakai is a dwarf bamboo grass suitable for food and health-related applications as it is a rich source of antioxidants. In this study, the leaves and culms of this plant were harvested from May to December, and the ethanol extracts of leaves (ESL) and culms (ESC), and the hot water extracts of leaves (HSL) and culms (HSC) were prepared. Extracts were evaluated for the seasonal changes in the content of p-coumaric acid, tricin, total phenolics (TP), and total flavonoids (TF) content; as well as for the antioxidant and anti-inflammatory activities. The p-coumaric acid in HSL and tricin contents in ESL rapidly decreased from June to October, and remained relatively constant until December. TP and TF contents in ESL were gradually increased from October and reached the highest level in December. The phenolic compounds (p-coumaric acid, tricin, TP and TF contents) in ESL showed an excellent correlation with antioxidant activities, indicating that ESL contained the highest levels of antioxidant and anti-inflammatory substances. Taken together, these results suggest that the optimal time to harvest this plant is from October to December.

Background Ulcerative colitis is a subtype of inflammatory bowel disease, characterized by relapsing inflammation in the gastrointestinal tract with limited treatment options. Previous studies suggested that the natural compound tricin, a flavone isolated from rice bran, could suppress chemically-induced colitis in mice, while our recent study also demonstrated the anti-metastatic effect of tricin in colon tumor-bearing mice. Hypothesis/Purpose Here we further investigated the underlying mechanism of the inhibitory effects of tricin on lipopolysaccharides-activated macrophage RAW264.7 cells and explored the efficacy of tricin in acute colitis mouse model induced by 4.5% dextran sulfate sodium (DSS) for 7 days. Methods Tricin (75, 100, and 150 mg/kg) or the positive control drug sulfasalazine (200 mg/kg) were orally administered to mice for 7 days. Stool consistency scores, stool blood scores, and body weight were recorded daily. Disease activity index (DAI) was examined on day 7, and colon tissues were collected for biochemical analyses. The fecal microbiome of colitis mice after tricin treatment was characterized for the first time in this study using 16S rDNA amplicon sequencing. Results Results showed that tricin (50 µM) remarkably reduced nitric oxide production in lipopolysaccharides-activated RAW264.7 cells and the anti-inflammatory activity of tricin was shown to act through the NF-κB pathway. Besides, tricin treatment at 150 mg/kg significantly reversed colon length reduction, reduced myeloperoxidase activities and DAI scores, as well as restored the elevated myeloid-derived suppressive cells population in acute colitis mice. The influence from DSS on gut microbiota, such as the increased population of Proteobacteria phylum and Ruminococcaceae family, was shown to be relieved after tricin treatment. Conclusion Our present study firstly demonstrated that tricin ameliorated acute colitis by improving colonic inflammation and modulating gut microbiota profile, which supports the potential therapeutic use of tricin for colitis treatment.

17 páginas.- 6 figuras.- 5 tablas.- referencias.- We acknowledge support of the publication fee by the CSIC Open Access Publication Support Initiative through its Unit of Information Resources for Research (URICI)., Rice (Oryza sativa L.) is a major cereal crop used for human nutrition worldwide. Harvesting and processing of rice generates huge amounts of lignocellulosic by-products such as rice husks and straw, which present important lignin contents that can be used to produce chemicals and materials. In this work, the structural characteristics of the lignins from rice husks and straw have been studied in detail. For this, whole cell walls of rice husks and straw and their isolated lignin preparations were thoroughly analyzed by an array of analytical techniques, including pyrolysis coupled to gas chromatography-mass spectrometry (Py-GC/MS), nuclear magnetic resonance (NMR), and derivatization followed by reductive cleavage (DFRC). The analyses revealed that both lignins, particularly the lignin from rice husks, were highly enriched in guaiacyl (G) units, and depleted in p-hydroxyphenyl (H) and syringyl (S) units, with H:G:S compositions of 7:81:12 (for rice husks) and 5:71:24 (for rice straw). These compositions were reflected in the relative abundances of the different interunit linkages. Hence, the lignin from rice husks were depleted in β–O–4′ alkyl-aryl ether units (representing 65% of all inter-unit linkages), but presented important amounts of β–5′ (phenylcoumarans, 23%) and other condensed units. On the other hand, the lignin from rice straw presented higher levels of β–O–4′ alkyl-aryl ethers (78%) but lower levels of phenylcoumarans (β–5′, 12%) and other condensed linkages, consistent with a lignin with a slightly higher S/G ratio. In addition, both lignins were partially acylated at the γ-OH of the side-chain (ca. 10–12% acylation degree) with p-coumarates, which overwhelmingly occurred over S-units. Finally, important amounts of the flavone tricin were also found incorporated into these lignins, being particularly abundant in the lignin of rice straw., his study has been funded by the Spanish Project AGL2017-83036-R (financed by Agencia Estatal de Investigación, AEI, and Fondo Europeo de Desarrollo Regional, FEDER). MJR thanks the Spanish Ministry of Science, Innovation and Universities for a FPI fellowship (PRE2018-083267). We acknowledge support of the publication fee by the CSIC Open Access Publication Support Initiative through its Unit of Information Resources for Research (URICI).

BackgroundBiomass composition varies from plant to plant and greatly affects biomass utilization. Lignin is a heterogeneous phenolic polymer derived mainly fromp-coumaryl, coniferyl, and sinapyl alcohols and makes up to 10–25% of lignocellulosic biomass. Recently, tricin, anO-methylated flavone, was identified as a lignin monomer in many grass species. Tricin may function as a nucleation site for lignification and is advocated as a novel target for lignin engineering to reduce lignin content and improve biomass digestibility in grasses. Thioacidolysis is an analytical method that can be adapted to analyze both lignin monomeric composition and tricin content in the lignin polymer. However, the original thioacidolysis procedure is complex, laborious, and time consuming, making it difficult to be adopted for large-scale screening in biomass research. In this study, a modified, rapid higher throughput thioacidolysis method was developed.ResultsIn combination with gas chromatography–mass spectrometry (GC–MS) and liquid chromatography–mass spectrometry (LC–MS), the modified thioacidolysis method can be used to simultaneously characterize the lignin composition and tricin content using 2–5 mg of dry samples. The modified method eliminates the solvent extraction and drastically improves the throughput; 80 samples can be processed in one day per person. Our results indicate that there is no significant difference in the determination of lignin S/G ratio and tricin content between the original and modified methods.ConclusionsA modified thioacidolysis protocol was established. The results demonstrate that the modified method can be used for rapid, high-throughput, and reliable lignin composition and tricin content analyses for screening transgenic plants for cell wall modifications or in large-scale genome-wide association studies (GWAS).

The plant Rhodiola rosea L. of family Crassulaceae was extracted using the supercritical CO2-extraction method. Several experimental conditions were investigated in the pressure range of 200–500 bar, with the used volume of cosolvent ethanol in the amount of 1% in the liquid phase at a temperature in the range of 31–70°C. The most effective extraction conditions are pressure 350 bar and temperature 60°C. The extracts were analyzed by HPLC with MS/MS identification. 78 target analytes were isolated from Rhodiola rosea (Russia) using a series of column chromatography and mass spectrometry experiments. The results of the analysis showed a spectrum of the main active ingredients Rh. rosea: salidroside, rhodiolosides (B and C), rhodiosin, luteolin, catechin, quercetin, quercitrin, herbacetin, sacranoside A, vimalin, and others. In addition to the reported metabolites, 29 metabolites were newly annotated in Rh. rosea. There were flavonols: dihydroquercetin, acacetin, mearnsetin, and taxifolin-O-pentoside; flavones: apigenin-O-hexoside derivative, tricetin trimethyl ether 7-O-hexosyl-hexoside, tricin 7-O-glucoronyl-O-hexoside, tricin O-pentoside, and tricin-O-dihexoside; flavanones: eriodictyol-7-O-glucoside; flavan-3-ols: gallocatechin, hydroxycinnamic acid caffeoylmalic acid, and di-O-caffeoylquinic acid; coumarins: esculetin; esculin: fraxin; and lignans: hinokinin, pinoresinol, L-ascorbic acid, glucaric acid, palmitic acid, and linolenic acid. The results of supercritical CO2-extraction from roots and rhizomes of Rh. rosea, in particular, indicate that the extract contained all biologically active components of the plant, as well as inert mixtures of extracted compositions.

Scutellaria araxensis is a well-known ethnobotanical herb for the treatment of various diseases in Iranian traditional medicine. In this study, dichloromethanolic fraction of partitioned methanol root and shoot extract was analysed by silica gel column chromatography, thin layer chromatography and high-performance liquid chromatography combined with photodiode-array detector, and coupled to electrospray ionization with Q-Exactive Orbitrap mass spectrometry (HPLC-PDA-ESI-MSn) in positive ion mode. Metabolites were tentatively characterized by comparing their mass spectrometry spectra with those of bibliographic data. A total of 11 flavonoids were identified from different fractions. Results showed that root and shoot produced very similar flavone patterns characterized by the presence of baicalein, tricin, tenaxin I, tenaxin II, skullcapflavon II, chrysin, wogonin and isorhamnetin. Norwogonin and apigenin-7-glucoside were identified only from shoot. Remarkably, Tenaxin I, II, tricin, apigenin-7-glucoside and norwogonin were tentatively profiled as new compounds for the first time from S. araxensis formula.

Simple Summary Over the past thirty years, the thermal modification of wood has become a universally recognised and commercialised wood modification process. Thermal modifications may affect wood properties, either positively (dimensional stability and decay resistance) or negatively (mechanical properties). The combination of the impregnation of specific reagents with thermal modification may help to overcome the negative effects on wood properties. In this study, we evaluate the effect of a combination of two zwitterionic buffers, bicine and tricine, and thermal modification of two wood species (beech and spruce) against subterranean termites and their symbiotic fauna. Bicine and tricine treatments alone had a clear influence on wood mass loss and termite survival. The flagellate protist symbiotic community was affected by the treatments and responded differently to them, as a highly adaptable community. However, the combination of bicine with the thermal modification showed a negative effect on termites and their symbionts on both wood species. The combination of these different factors should be further investigated, as these results seem to be promising with regard to the enhancement of the termite resistance of wood. Abstract The majority of thermal modification processes are at temperatures greater than 180 °C, resulting in a product with some properties enhanced and some diminished (e.g., mechanical properties). However, the durability of thermally modified wood to termite attack is recognised as low. Recent attempts at combining thermal modification with chemical modification, either prior to or directly after the thermal process, are promising. Buffers, although not influencing the reaction systems, may interact on exposure to certain conditions, potentially acting as promoters of biological changes. In this study, two zwitterionic buffers, bicine and tricine, chosen for their potential to form Maillard-type products with fragmented hemicelluloses/volatiles, were assessed with and without thermal modification for two wood species (spruce and beech), with subsequent evaluation of their effect against subterranean termites (Reticulitermes grassei Clément) and their symbiotic protists. The effect of the wood treatments on termites and their symbionts was visible after four weeks, especially for spruce treated with tricine and bicine and heat treatment (bicine HT), and for beech treated with bicine and bicine and heat treatment (bicine HT). The chemical behaviour of these substances should be further investigated when in contact with wood and also after heat treatment. This is the first study evaluating the effect of potential Maillard reactions with zwitterionic buffers on subterranean termite symbiotic fauna.

Rice (Oryza sativa L.) is a major cereal crop used for human nutrition worldwide. Harvesting and processing of rice generates huge amounts of lignocellulosic by-products such as rice husks and straw, which present important lignin contents that can be used to produce chemicals and materials. In this work, the structural characteristics of the lignins from rice husks and straw have been studied in detail. For this, whole cell walls of rice husks and straw and their isolated lignin preparations were thoroughly analyzed by an array of analytical techniques, including pyrolysis coupled to gas chromatography-mass spectrometry (Py-GC/MS), nuclear magnetic resonance (NMR), and derivatization followed by reductive cleavage (DFRC). The analyses revealed that both lignins, particularly the lignin from rice husks, were highly enriched in guaiacyl (G) units, and depleted in p-hydroxyphenyl (H) and syringyl (S) units, with H:G:S compositions of 7:81:12 (for rice husks) and 5:71:24 (for rice straw). These compositions were reflected in the relative abundances of the different interunit linkages. Hence, the lignin from rice husks were depleted in β–O–4′ alkyl-aryl ether units (representing 65% of all inter-unit linkages), but presented important amounts of β–5′ (phenylcoumarans, 23%) and other condensed units. On the other hand, the lignin from rice straw presented higher levels of β–O–4′ alkyl-aryl ethers (78%) but lower levels of phenylcoumarans (β–5′, 12%) and other condensed linkages, consistent with a lignin with a slightly higher S/G ratio. In addition, both lignins were partially acylated at the γ-OH of the side-chain (ca. 10–12% acylation degree) with p-coumarates, which overwhelmingly occurred over S-units. Finally, important amounts of the flavone tricin were also found incorporated into these lignins, being particularly abundant in the lignin of rice straw.

Ultraviolet A (UVA) is a risk factor for photoaging and wrinkle formation. Zizania latifolia is an herbaceous perennial plant. It contains many bioactive compounds such as tricin that show antioxidative and anti-inflammatory effects. The aim of this study was to investigate the antiwrinkle effect of a mixture of hydrolytic enzyme (cellulase, hemicellulase and pectinase)-treated Z. latifolia extract (ZLE) and tricin on UVA-irradiated human dermal fibroblasts (HDFs) and SKH-1 hairless mice. Treatment of UVA-irradiated HDF cells with ZLE and tricin significantly decreased UVA induced-plasma membrane rupture, generation of ROS, expression levels of total and secreted lysosomal associated membrane protein (LAMP-1), cathepsin B and metalloproteinases (MMPs) and inhibited NF-&kappa, B activation. In the animal study, UVA-damaged epidermal and dermal tissues were repaired by the ZLE and tricin treatments. Administration of ZLE or tricin to UVA-irradiated animals recovered skin surface moisture and collagen fiber in dermal tissue. Treatment of ZLE or tricin decreased wrinkle formation, secretion of MMPs and expression levels of vascular endothelial growth factor (VEGF) and cathepsin B, and increased the expression level of collagen-1 in UVA-irradiated animals. Overall, the ZLE and tricin treatments decreased the skin damage induced by UVA irradiation via inhibition of lysosomal exocytosis and ROS generation. Therefore, ZLE and tricin are promising as antiwrinkle and antiphotoaging agents.

Xanthine oxidase (XO) inhibition is a major strategy for preventing hyperuricemia and associated comorbidities, such as gout. Alfalfa extract has been demonstrated to possess XO-inhibiting activity; however, the elaborate conventional fraction-by-fraction analyses hindered the identification of the active components. In this study, we established a streamlined approach to rapidly screen, identify, and characterize XO-interacting compounds in alfalfa, by incorporating protein-subtraction, mass profiling, and molecular docking analysis. Crude extract was incubated with or without XO protein before UPLC-ESI-Q-TOF-MS/MS composition profiling. By dereplicating the component profile of XO-subtracted extract from that of untreated extract, the targets were rapidly narrowed down to twelve XO-interacting compounds, regarded as potential xanthine oxidase inhibitors (XOIs). Molecular docking analysis revealed that nine of these compounds, namely salicylic acid, tricin 7-O-glucuronopyranoside, chrysoeriol-7-glucoside, ferulic acid, apigenin 7-O-β-glucuronopyranoside, apigenin, tricin, chrysoeriol, and liquiritigenin, exhibited high affinity with XO, and depicted the possible mechanisms of inhibition. In vitro bioassay further verified the XO inhibitory activities of selected compounds, among which apigenin, chrysoeriol and liquiritigenin were more potent XO inhibitors (XOIs), with IC50 of 0.25, 0.5 and 1 µM, respectively, compared to allopurinol (IC50 = 1.41 µM), the well-known XO-inhibiting drug. Together, the results demonstrated that alfalfa is a promising natural source for potent XOIs which might be applied for nutraceuticals development and that the approach used is applicable for efficient screening, identification, and mechanistic analyses of enzyme-inhibiting compounds from plant-based resources.

In a cytopathic effect inhibition assay, a standardized Rhodiola rosea root and rhizome extract, also known as roseroot extract (SHR-5), exerted distinct anti-influenza A virus activity against HK/68 (H3N2) (IC50 of 2.8 µg/mL) without being cytotoxic. For fast and efficient isolation and identification of the extractʼs bioactive constituents, a high-performance countercurrent chromatographic separation method was developed. It resulted in a three-stage gradient elution program using a mobile phase solvent system composed of ethyl acetate/n-butanol/water (1 : 4 : 5 → 2 : 3 : 5 → 3 : 2 : 5) in the reversed-phase mode. The elaborated high-performance countercurrent chromatographic method allowed for fractionation of the complex roseroot extract in a single chromatographic step in a way that only one additional orthogonal isolation/purification step per fraction yielded 12 isolated constituents. They cover a broad polarity range and belong to different structural classes, namely, the phenylethanoid tyrosol and its glucoside salidroside, the cinnamyl alcohol glycosides rosavin, rosarin, and rosin as well as gallic acid, the cyanogenic glucoside lotaustralin, the monoterpene glucosides rosiridin and kenposide A, and the flavonoids tricin, tricin-5-O-β-D-glucopyranoside, and rhodiosin. The most promising anti-influenza activities were determined for rhodiosin, tricin, and tricin-5-O-β-D-glucopyranoside with IC50 values of 7.9, 13, and 15 µM, respectively. The herein established high-performance countercurrent chromatographic protocol enables fast and scalable access to major as well as minor roseroot constituents. This is of particular relevance for extract standardization, quality control, and further in-depth pharmacological investigations of the metabolites of this popular traditional herbal remedy.

Tricin, a flavone isolated from rice bran, has been shown to be chemopreventive in a colorectal cancer (CRC) mouse model. This study aimed to illustrate the inhibitory activities of tricin in colon cancer cells and in a metastatic CRC mouse model. BALB/c mice injected with mouse Colon26-Luc cells into the rectum wall were treated with tricin (37.5 mg/kg) daily for 18 days. Orthotopic colon tumor growth and metastasis to lungs were assessed by in vivo bioluminescence imaging. Results showed that tricin suppressed Colon-Luc cells motility and downregulated phosphorylated Akt, Erk1/2 and NF-κB expressions of human colon cancer HT-29 cells. While tricin treatment suppressed tumor growth and lung metastasis as well as altered the populations of myeloid-derived suppressor cells and regulatory T cells in spleens. In summary, the tumor microenvironment modulatory and anti-metastatic effects of tricin in colon cancer mouse model were shown for the first time, suggesting the potential development of tricin-containing food supplements for CRC patients.

13 páginas.- 8 figuras.- 3 tablas.- 63 referencias, This perspective summarizes and compares computational results for the thermodynamics of bond dissociation, coupling, and rearomatization for a number of noncanonical lignin monomer–lignol combinations that have been found to occur experimentally. The noncanonical lignin monomers discussed are tricin, caffeyl alcohol, 5-hydroxyconiferyl alcohol, and piceatannol. Among dimeric combinations, the results for bond dissociation are generally similar, but in cases for which trimers have been reported (tricin-lignol adducts), this value can be quite variable, with stereochemical and structural preferences. Among the adducts examined thus far, the energies associated with quinone methide formation and rearomatization are not dissimilar and would not impede subsequent polymerization. These fundamental studies may help to elucidate how lignin monomers are incorporated into the lignin polymer, provide leads for targeted genetic modification, and be of use in deconstruction for the production of commodity chemicals., J. Re. and J.C.d.R. were funded by the Spanish Projects CTQ2014-60764-JIN and AGL2017-83036-R (financed by Agencia Estatal de Investigacion, AEI, and Fondo Europeo de Desarrollo Regional, FEDER).

16 páginas.- 6 figuras.- 131 referencias, Lignin is conventionally defined as being formed by the oxidative polymerization of three main monolignols, p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, that are derived from the general phenylpropanoid biosynthetic pathway. Many other phenolic compounds that are also derived from the phenylpropanoid pathway are also known to perform as genuine lignin monomers in many plants, as is the case of the monolignol ester conjugates, phenolic compounds arising from the truncated biosynthesis of monolignols, or ferulate esters. Recent investigations, however, have indicated that phenolic compounds arising from beyond the canonical phenylpropanoid pathway, namely flavonoids, hydroxystilbenes, and hydroxycinnamic amides, may also behave as authentic lignin monomers and are incorporated into the lignin in some plants, further challenging the traditional definition of lignin. This is the case of the flavone tricin that is incorporated into the lignin of grasses and other monocots, the hydroxystilbene piceatannol (together with resveratrol and isorhapontigenin, at lower levels) that has been found in the lignins of palm fruit shells, their respective O-glucosides (astringin, piceid, and isorhapontin) that are present in the lignin of Norway spruce bark, or the ferulic amides feruloyltyramine, incorporated into the lignin of tobacco and potato tubers, and diferuloylputrescine, which appears to be incorporated into maize kernel lignin. These valuable compounds are potentially available in high amounts and at low cost and may be obtained from the waste products from the processing of agricultural or forest biomass., J. C. del Rıo, J. Rencoret, and A. Gutiérrez were funded by the Spanish Project AGL2017-83036-R (financed by Agencia Estatal de Investigacion, AEI, and Fondo Europeo de Desarrollo ́ Regional, FEDER). J. Ralph and H. Kim were funded by the DOE Great Lakes Bioenergy Research Center (DOE Office of Science DE-SC0018409). T. Elder was funded by the National Science Foundation (grant number ACI-1548562).

Rationale We report the top-down lignomic analysis of the virgin released lignin (VRL) small oligomers obtained from French Oak wood. Methods We have used MALDI-TOF-MS in the negative ion mode for the analysis of the complex mixture of lignin oligomers extracted from French Oak wood. High-energy CID-TOF/TOF-MS/MS analyses were used to support the postulated precursor ion structures. Results Twenty compounds were identified using MALDI-TOF-MS/MS of the VRL extracted from French Oak wood: seven tricin derivatives and/or flavonoids, three syringylglycerol derivatives, two syringol derivatives, two flavonolignin derivatives, and six miscellaneous compounds: luteoferol, lariciresinol isomer, 5-hydroxy guaiacyl derivative, syringyl -C10 H10 O2 dimer, trihydroxy benzaldehyde derivative, and aryl tetralin lignan derivative. Most of the identified compounds were in the form of carbohydrate and/or shikimic acid complexes. Conclusions The analysis of this complex mixture led to the identification of a series of lignin dimers, novel lignin-carbohydrate complexes (LCC), and unique tricin derivatives linked to different types of carbohydrates and shikimic acid moieties. This finding supports the presence of lignin-carbohydrate complexes in the isolated VRL. These analyses also showed that French Oak lignin is abundant in syringol moieties present in the lignin syringyl units or tricin derivatives. Moreover, the identification of some lignin-carbohydrate and/or flavonoid-shikimic acid complexes could provide new insight into the relationship between the biosynthesis of lignin and tricin.

To evaluate possibility as a skin whitening agent of Sorghum bicolor (S. bicolor), its antioxidant activity and anti-melanogenic effect on 3-isobutyl-1-methylxanthine (IBMX)-induced melanogenesis in B16/F10 melanoma cells were investigated. The result of total phenolic contents (TPC) indicated that 60% ethanol extract of S. bicolor (ESB) has the highest contents than other ethanol extracts. Antioxidant activity was evaluated using the 2,2&rsquo, azino-bis-(3-ethylbenzothiazolin-6-sulfonic acid) diammonium salt (ABTS)/1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activities and malondialdehyde (MDA) inhibitory effect. These results showed ESB has significant antioxidant activities. Inhibitory effect against tyrosinase was also assessed using L-tyrosine (IC50 value = 89.25 &mu, g/mL) and 3,4-dihydroxy-L-phenylalanine (L-DOPA) as substrates. In addition, ESB treatment effectively inhibited melanin production in IBMX-induced B16/F10 melanoma cells. To confirm the mechanism on anti-melanogenic effect of ESB, we examined melanogenesis-related proteins. ESB downregulated melanogenesis by decreasing expression of microphthalmia-associated transcription factor (MITF), tyrosinase and tyrosinase-related protein (TRP)-1. Finally, 9-hydroxyoctadecadienoic acid (9-HODE), 1,3-O-dicaffeoylglycerol and tricin as the main compounds of ESB were analyzed using the ultra-performance liquid chromatography-ion mobility separation-quadrupole time of flight/tandem mass spectrometry (UPLC-IMS-QTOF/MS2). These findings suggest that ESB may have physiological potential to be used skin whitening material.

Scented (joha) and black rice indigenous to northeast region (NER) of India are the two among 40,000 varieties of species Oryza sativa, prevalent for its great aroma, medicinal property, and/or equally noteworthy taste. Biochemical and target-based liquid chromatography mass spectrometry (LCMS) analysis was performed to identify and quantify the different phytonutrients from the selected rice grains of those two varieties. Biochemical assay revealed that the selected black rice (Chakhao Amubi) contains ∼1.8-fold higher amount of total phenolic and ∼2.3-fold higher amount of total flavonoid than the scented rice grain (Kon joha). The total starch content was significantly lower in scented rice in comparison to black rice grain. The health beneficial ratio of ω-6/ω-3 essential unsaturated fatty acid is notably better in scented rice grain than black rice grain. The targeted LC-MS/MS analysis confirms the presence of oryzanol and ferulic acid in both the samples. The presence of 4-hydroxy benzoic acid, apigenin, tricin, avenasterol, coumarin, coumaric acid, phenyl alanine, caffeic acid, and α-tocophenol were confirmed in the scented rice, whereas the black rice confirms the presence of protocatechuic acid and dehydroxy myricetin. Further the quantitative analysis showed that the lipids lysophosphatidylinositol (LPI) 16:0, lysophosphatidyl ethanolamine (LPE) 14:0, lysophosphatidyl choline (LPC) 18:2, LPE 18:2, phosphatidyl etanolamine (PE), along with oryzanol, hydroxy docosanoic acid are at least threefold higher in scented rice varietal; whereas, in Chakhao Amubi, the content of petunidin galactoside, LMMPE18:2, PC14:0 are higher than the scented rice grain. In conclusion, different phytonutrients including phenol, polyphenol, and flavonoid have been identified as bioactive phytochemicals in selected rice varietals. PRACTICAL APPLICATION: This work will provide the information about the nutritional benefit of studied rice varietals. The used targeted LC-MS/MS analysis will provide the one-step information about the bioactive phytochemicals. Overall, this study will help to commercialize those varieties with proper scientific evidences.

Cymbaria daurica L. is widely used in traditional Mongolian medicine for the treatment of impetigo, psoriasis, pruritus, fetotoxicity, and diabetes. Therefore, the anti-inflammatory and α-glucosidase-inhibitory activities of four polar C. daurica extracts (water, n-butanol, ethyl acetate, and petroleum ether extract) were preliminarily evaluated to identify the active extracts. We also investigated the chemical composition of the active extracts by phytochemical analysis. The n-butanol and ethyl acetate extracts exhibited significant (p < 0.05) anti-inflammatory activities by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 cells. None of the tested extracts exhibited cytotoxic effects at the effective concentrations. The ethyl acetate extract significantly inhibited α-glucosidase activity, and the inhibition potency was equivalent to that of acarbose (p > 0.05). The n-Butanol extract presented the second highest inhibitory activity. As the n-butanol and ethyl acetate extracts were found to have potent anti-inflammatory and α-glucosidase-inhibitory activities, we separated and identified 10 compounds from the extracts. Among them, vanillic acid, cistanoside F, echinacoside, arenarioside, verbascoside, isoacteoside, and tricin were isolated from C. daurica for the first time. Further, 30 compounds from the n-butanol and ethyl acetate extracts of C. daurica were identified using UHPLC-Q-Exactive. The present study demonstrates for the first time that C. daurica contains phenylethanoid glycosides. In addition, this novel HPLC method was subsequently used for simultaneous identification of five compounds in the n-butanol and ethyl acetate extracts of C. daurica. This study provides a chemical basis for further characterization and utilization of C. daurica, which could be a potential source of novel anti-diabetic and anti-inflammatory agents.

Scutellaria araxensis, S. bornmuelleri and S. orientalis are traditional herbs widely used by native Iranians for the treatment various ailments. In the current study, we used HPLC-DAD-ESI/MSn to investigate the presence of phenolic compounds of root and shoot methanolic extracts. The flavonoid composition were identified based on mass of pseudomolecular [M − H]− ions and fragmentation spectra and comparisons with literature data. A total of 26, 25, 17, 23, 19 and 26 flavonoids were identified from roots and shoots of S. araxensis, S. bornmuelleri and S. orientalis, respectively. The obtained phenolic profiles revealed the presence of the major flavonoid components of Scutellaria genus including baicalein, wogonin, scutellarein and their glycosides, as well as chrysin, tricin, skullcapflavon II, pinocembrin and phenylethanoid glycosides such as acteoside and verbascoside. This study, in addition to reveal the potency of chromatographic profiling for identification of Scutellaria flavonoids, introduces this species as a potential source of bioactive metabolites.

[EN] Health beneficial effects of sugarcane have been attributed to antioxidant components present in the plant material, phenolic compounds having been identified mainly in the raw juice, culms and leaves. However, the presence of specific natural phenolic constituents in non-refined cane sugars and their potential impact on the diet as an alternative to refined sugar have not been completely evaluated. Phenolic constituents of six commercially available sugarcane derivatives (granulated jaggery, muscovado sugar, light and regular jaggery blocks, cane honey and brown sugar) were identified and quantified, in addition to their physicochemical, antioxidant and antimicrobial properties against cariogenic bacteria. Physicochemical and antioxidant properties of raw sugars were highly related to degree of refining of each product. Specific hydroxycinnamic acids (chlorogenic, caffeic, coumaric, ferulic) and flavones (apigenin, tricin, luteolin) were identified and quantified in sugarcane products. Tricin and apigenin were the most abundant phenolics in raw sugars, both considered important bioactive constituents of foods which postulate as nutraceuticals, antiproliferative and chemopreventive agents. Some derivatives and their extracts also exhibited antibacterial properties against Streptococcus mutans and Streptococcus sobrinus. Bioactive compounds identified in raw sugars make sugarcane natural sweeteners a healthier alternative to white sugar, to be used at home and industry. Granulated jaggeries postulate as the best substitutive due to their nutritional benefits and physicochemical attributes., This work was supported by the Universitat Politecnica de Valencia (UPV/PAID2010-2420) and Generalitat Valenciana (GV/2013/047). The authors would like to acknowledge both institutions for financial support.