Syringin: A Phenylpropanoid Glycoside Compound in Cirsium brevicaule A. GRAY Root Modulates Adipogenesis.

Cirsium brevicaule A. GRAY is a wild perennial herb, and its roots (CbR) have traditionally been used as both food and medicine on the Japanese islands of Okinawa and Amami. The present study evaluated the antiadipogenic effect of CbR using mouse embryonic fibroblast cell line 3T3-L1 from JCRB cell bank. Dried CbR powder was serially extracted with solvents of various polarities, and these crude extracts were tested for antiadipogenic activity. Treatment with the methanol extract of CbR showed a significant suppression of lipid accumulation in 3T3-L1 cells. Methanol extract of CbR was then fractionated and subjected to further activity analyses. The phenylpropanoid glycosidic molecule syringin was identified as an active compound. Syringin dose dependently suppressed lipid accumulation of 3T3-L1 cells without cytotoxicity, and significantly reduced the expressions of peroxisome proliferator-activated receptor gamma, the master regulator of adipogenesis, and other differentiation markers. It was demonstrated that syringin effectively enhanced the phosphorylation of the AMP-activated protein kinase and acetyl-CoA carboxylase. These results indicate that syringin attenuates adipocyte differentiation, adipogenesis, and promotes lipid metabolism; thus, syringin may potentially serve as a therapeutic candidate for treatment of obesity.

Metabolic Alterations in Two Cirsium Species Identified at Distinct Phenological Stages using UPLC-QTOF/MS.

INTRODUCTION: Cirsium chanroenicum and C. setidens are commonly used both in traditional folk medicine and as a food source. The quality of different species of Cirsium at different harvest times is a function of their metabolite composition, which is determined by the phenological stage. OBJECTIVE: We sought to determine the differences in the metabolite composition of two species of Cirsium during different phenological stages using ultra-performance liquid chromatography (UPLC) quadrupole time-of-flight (QTOF) mass spectrometry (MS). METHODOLOGY: Cirsium chanroenicum and C. setidens plants were collected at the floral budding and full flowering stages. Metabolic profiles of Cirsium extracts were determined using UPLC-QTOF/MS to characterise the differences between phenological stages, and the major metabolites were quantified using UPLC-QTOF/MS-multiple reaction monitoring (MRM). RESULTS: At the full flowering stage, the levels of phenolic acids as well as components of the phenylpropanoid pathway were increased. Flavonoids predominated at the full flowering stage in both species. The levels of coumaric acid, kaempferol, and pectolinarigenin differed between the two species of Cirsium. Overall, these results suggest that components of the phenylpropanoid metabolic pathway are upregulated in the full flowering stage in Cirsium, although we did observe some variation between the species. CONCLUSION: These results will help elucidate the metabolic pathways related to the different phases of the vegetative cycle, and may help determine the optimal season for the harvest of Cirsium with the highest levels of bioactive compounds. Copyright © 2017 John Wiley & Sons, Ltd.

Anti-inflammatory effects and corresponding mechanisms of cirsimaritin extracted from Cirsium japonicum var. maackii Maxim.

In this study, we investigated the anti-inflammatory effects and mechanisms of cirsimaritin isolated from an ethanol extract of the aerial parts of Cirsium japonicum var. maackii Maxim. using RAW264.7 cells. The extract and its flavonoid cirsimaritin inhibited nitric oxide (NO) production and inducible nitric oxide synthase expression in RAW264.7 cells. Cirsimaritin inhibited interleukin-6, tumor necrosis factor-α, and NO production in a concentration-dependent manner in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. From a western blot study, pretreatment with cirsimaritin inhibited phosphorylation/degradation of IκBα and phosphorylation of Akt in LPS-stimulated RAW264.7 cells. Moreover, cirsimaritin suppressed activation of LPS-induced transcription factors, such as c-fos and signal transducer and activator of transcription 3 (STAT3), in RAW264.7 cells. Collectively, these results show that cirsimaritin possesses anti-inflammatory activity, which is regulated by inhibition of c-fos and STAT3 phosphorylation in RAW264.7 cells.

Infection by a foliar endophyte elicits novel arabidopside-based plant defence reactions in its host, Cirsium arvense.

Endophytic fungi live asymptomatically within plants. They are usually regarded as nonpathogenic or even mutualistic, but whether plants respond antagonistically to their presence remains unclear, particularly in the little-studied associations between endophytes and nongraminoid herbaceous plants. We investigated the effects of the endophyte Chaetomium cochlioides on leaf chemistry in Cirsium arvense. Plants were sprayed with spores; leaf material from both subsequent new growth and the sprayed leaves was analysed 2 wk later. Infection frequency was 91% and 63% for sprayed and new growth, respectively, indicating that C. cochlioides rapidly infects new foliage. Metabolomic analyses revealed marked changes in leaf chemistry with infection, especially in new growth. Changes in several novel oxylipin metabolites were detected, including arabidopsides reported here for the first time in a plant species other than Arabidopsis thaliana, and a jasmonate-containing galactolipid. The production of these metabolites in response to endophyte presence, particularly in newly infected foliage, suggests that endophytes elicit similar chemical responses in plants to those usually produced following wounding, herbivory and pathogen invasion. Whether endophytes benefit their hosts may depend on a complex series of chemically mediated interactions between the plant, the endophyte, other microbial colonists and natural enemies.

Metabolite profiling to discriminate different species and genus from thistles in Korea using liquid chromatography with quadrupole time-of-flight mass spectrometry.

This study was designed to classify and identify closely related thistle species in the genus Cirsium, as well as Carduus and Cephalonoplos species, which are also thistles. The comprehensive and untargeted metabolite profiles of nine Korean thistles were determined using ultra high performance liquid chromatography combined with hybrid quadrupole time-of-flight mass spectrometry. The difference in metabolite profiles among species was explored using principal component analysis and hierarchical clustering analysis. The significantly different metabolites (Bonferroni-corrected P-value < 0.001) were used to construct a partial least squares discriminant analysis model to predict the species of thistle. Nine species were successfully classified using a partial least squares discriminant analysis model and confirmed using a cross-validation method. Species with similar features were grouped based on unique patterns in variable clusters. The present study suggests that liquid chromatography with quadrupole time-of-flight mass spectrometry untargeted metabolomic profiling with chemometric analysis is an efficient and powerful tool for discriminating between different species of medicinal herbs.

The effect of Cirsium arvense extract on antioxidant status in quail.

1. The herb Creeping Thistle, Cirsium arvense (C. arvense), has been used in folk medicine due to its antioxidant and anti-inflammatory effects. 2. The aim of this study was to investigate the effects of dietary C. arvense extract supplementation on performance, egg quality, nutrient digestibility and antioxidant status in quail. 3. Quails (n = 150) were allocated randomly to one of the three dietary treatments: basal diet and basal diet enriched with 100 and 200 mg C. arvense extract per kg diet. 4. Dietary enrichment with C. arvense extract altered neither performance and egg quality parameters nor nutrient digestibility. Although there were no changes in concentrations of vitamin A and E in serum, liver and egg yolk, supplemental C. arvense extract decreased MDA concentrations in serum, liver and egg yolk by 39.3, 40.5 and 51.5%, respectively, in a dose-response manner. As supplemental C. arvense extract increased to 200 mg/kg, the activity of hepatic SOD, CAT and GSH-Px increased by 14.5, 17.4 and 35.5%, respectively. 5. Addition of C. arvense extract up to 200 mg to per kg diet enhanced antioxidant status in laying quail and their eggs, without affecting performance and other egg quality parameters. 6. Future studies are needed to elucidate the mechanism behind the antioxidant effects of C. arvense extract.

Auxin and ABA act as central regulators of developmental networks associated with paradormancy in Canada thistle (Cirsium arvense).

Dormancy in underground vegetative buds of Canada thistle, an herbaceous perennial weed, allows escape from current control methods and contributes to its invasive nature. In this study, ~65 % of root sections obtained from greenhouse propagated Canada thistle produced new vegetative shoots by 14 days post-sectioning. RNA samples obtained from sectioned roots incubated 0, 24, 48, and 72 h at 25°C under 16:8 h light-dark conditions were used to construct four MID-tagged cDNA libraries. Analysis of in silico data obtained using Roche 454 GS-FLX pyrosequencing technologies identified molecular networks associated with paradormancy release in underground vegetative buds of Canada thistle. Sequencing of two replicate plates produced ~2.5 million ESTs with an average read length of 362 bases. These ESTs assembled into 67358 unique sequences (21777 contigs and 45581 singlets) and annotation against the Arabidopsis database identified 15232 unigenes. Among the 15232 unigenes, we identified processes enriched with transcripts involved in plant hormone signaling networks. To follow-up on these results, we examined hormone profiles in roots, which identified changes in abscisic acid (ABA) and ABA metabolites, auxins, and cytokinins post-sectioning. Transcriptome and hormone profiling data suggest that interaction between auxin- and ABA-signaling regulate paradormancy maintenance and release in underground adventitious buds of Canada thistle. Our proposed model shows that sectioning-induced changes in polar auxin transport alters ABA metabolism and signaling, which further impacts gibberellic acid signaling involving interactions between ABA and FUSCA3. Here we report that reduced auxin and ABA-signaling, in conjunction with increased cytokinin biosynthesis post-sectioning supports a model where interactions among hormones drives molecular networks leading to cell division, differentiation, and vegetative outgrowth.

Biologically synthesis of gold nanoparticles using Cirsium japonicum var. maackii extract and the study of anti-cancer properties on AGS gastric cancer cells.

Plant extract-mediated synthesis of metal nanoparticles (NPs) is an eco-friendly and cost-effective biosynthesis method that is more suitable for biological applications than chemical ones. We prepared novel gold NPs (AuNPs), Cirsium japonicum mediated-AuNPs (CJ-AuNPs), using a biosynthetic process involving Cirsium japonicum (Herba Cirsii, CJ) ethanol extract. The physicochemical properties of CJ-AuNPs were characterized using spectrometric and microscopic analyses. The in vitro stability of CJ-AuNPs was studied for 3 months. Moreover, the selective human gastric adenocarcinoma (AGS) cell killing ability of CJ-AuNPs was verified in cancer and normal cells. An in vitro study revealed that CJ-AuNPs trigger oxidative stress and iron-dependent ferroptosis in AGS cells. Mechanistically, CJ-AuNPs induced mitochondrial reactive oxygen species (ROS), Fe2+, and lipid peroxidation accumulation, and mitochondrial damage by destroying the glutathione peroxidase-4 (GPX4)-dependent antioxidant capacity. Furthermore, in a xenograft mouse model implanted with AGS cells, treatment with 2.5, 5, and 10 mg/kg CJ-AuNPs for 16 days reduced tumor xenograft growth in a dose dependent manner in vivo without systemic toxicity. These results demonstrate that CJ-AuNPs exert anticancer effects in vitro and in vivo by inducing ferroptosis-mediated cancer cell death. This study, based on green-synthesized nanodrug-induced ferroptosis, provides new insight into potential developments in cancer therapies.

Contamination of the guttation liquid of two common weeds with neonicotinoids from coated maize seeds planted in close proximity.

Neonicotinoid uptake by maize plants emerged from coated seeds and by two common weeds grown in close proximity to coated seeds has been studied. Uptake of thiamethoxam (TMX) and clothianidin (CLO) have been characterized via guttation liquid measurements. The creeping thistle (Cirsium arvense), a well-known maize weed, as well as red poppy or Flanders poppy (Papaver rhoeas) were chosen as model species. The results confirmed that cross-contamination may occur by uptake of the neonicotinoid AIs through soil from neighbouring plants that emerged from coated seeds. Although the levels of these neonicotinoids were substantially lower in the guttation liquid of the weeds than in that of maize plants emerged from coated seeds, the compounds were detected up to 36th day after planting of the maize seeds. The highest peak concentrations of TMX were around 150 and 21 mg L-1, while similar data for CLO were around 70 and 21 mg L-1 for maize and creeping thistle, respectively. Mostly due to its higher guttation intensity significantly lower values were determined for red poppy (0.740 mg L-1).

Nonenolides and cytochalasins with phytotoxic activity against Cirsium arvense and Sonchus arvensis: a structure-activity relationships study.

A structure-activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world. The toxic nonenolides (stagonolide, putaminoxin, pinolidoxin) and cytochalasins (deoxaphomin, cytochalasins A, B, F, T, Z2 and Z3) were isolated from phytopathogenic Stagonospora, Phoma and Ascochyta spp. The pinolidoxin (7,8-O,O'-diacetyl- and 7,8-O,O'-isopropylidene-pinolidoxin) and cytochalasins B (21,22-dihydro-, 7-O-acetyl- and 7,20-O,O'-diacetyl-cytochalasin B) derivatives were obtained by chemical modifications of the corresponding toxins. Among the 15 compounds tested, stagonolide and deoxaphomin proved to be the most phytotoxic to C. arvense and S. arvensis leaves, respectively. The tested phytotoxic nonenolides were stronger inhibitors of photosynthesis in C. arvense leaves than cytochalasines A and B. Stagonolide had less effect on membrane permeability in C. arvense leaves than cytochalasin B. Significant changes of light absorption by C. arvense leaves in visible and infrared spectra were caused by stagonolide. The functional groups and the conformational freedom of the ring, appear to be important structural features for the nonenolides toxicity, whereas and the presence of the hydroxy group at C-7, the functional group at C-20 and the conformational freedom of the macrocyclic ring are important for the cytochalasins toxicity.

Cirsimarin, a flavone glucoside from the aerial part of Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi, suppresses the JAK/STAT and IRF-3 signaling pathway in LPS-stimulated RAW 264.7 macrophages.

Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi (C. ussuriense) is known as "Dae-Gye" or "Korean milk thistle". C. ussuriense have long been used as a folk medicinal plant for inflammatory diseases such as hepatitis, nephritis, and mastitis in Korea, China, and Japan. To reveal the anti-inflammatory components of C. ussuriense, we isolated three flavone glycosides (linarin, cirsimarin, and hispidulin-7-O-neohesperidoside) from the aerial part of C. ussuriense and evaluated their inhibitory effects on LPS-induced pro-inflammatory mediators in macrophages. We also investigated the involving molecular mechanisms of cirsimarin. Among three flavone glycosides, cirsimarin showed vastly superior inhibitory potency in LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production. Cirsimarin concentration-dependently inhibited LPS-induced inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein and mRNA levels in macrophages. Cirsimarin suppressed the production and mRNA expression of tumor necrosis factor- α (TNF-α) and interleukin (IL)-6 in LPS-stimulated RAW 264.7 and bone marrow-derived macrophages. Moreover, molecular data presented that cirsimarin down-regulated the phosphorylation of Janus kinase (JAK)/signal transducer and activator of transcriptions (STATs) and p38 mitogen-activated protein kinase (MAPK), and nuclear translocation of interferon regulatory factor (IRF)-3. Collectively, cirsimarin may be an active ingredient responsible for anti-inflammatory effects of C. ussuriense and it may act as a promising therapeutic against inflammatory diseases by suppressing the JAK/STAT and IRF-3 signaling pathway.

Biodegrader metabolic expansion during polyaromatic hydrocarbons rhizoremediation.

Root-microbe interactions are considered to be the primary process of polyaromatic hydrocarbon (PAH) phytoremediation, since bacterial degradation has been shown to be the dominant pathway for environmental PAH dissipation. However, the precise mechanisms driving PAH rhizostimulation symbiosis remain largely unresolved. In this study, we assessed PAH degrading bacterial abundance in contaminated soils planted with 18 different native Michigan plant species. Phenanthrene metabolism assays suggested that each plant species differentially influenced the relative abundance of PAH biodegraders, though they generally were observed to increase heterotrophic and biodegradative cell numbers relative to unplanted soils. Further study of >1800 phenanthrene degrading isolates indicated that most of the tested plant species stimulated biodegradation of a broader range of PAH compounds relative to the unplanted soil bacterial consortia. These observations suggest that a principal contribution of planted systems for PAH bioremediation may be via expanded metabolic range of the rhizosphere bacterial community.

Enhanced visible light photocatalytic inactivation of Escherichia coli using silver nanoparticles as photocatalyst.

The silver nanoparticles (AgNPs) were green synthesized using Cirsium arvense plant extract as a reducing and stabilizing agent, with superior photo inactivation activity against Escherichia coli (E. coli). The synthesized AgNPs had crystalline structure and were characterized by UV-vis spectroscopy, XRD, HRTEM, SEM, EDX and FT-IR. The formation of nanoparticles was observed at different pH and different plant extract concentrations and it was found that at higher pH (pH>6) and at lower concentration (10 mL), the reducing and stabilizing efficiency of plant extract was increased. The synthesized AgNPs had small size (<15 nm) and spherical shape. The AgNPs were evaluated for antibacterial activity against E. coli. Before transferring it to antibacterial activity, it was placed under visible light for 120 min. The same experiment was performed in dark as a control medium. The photo irradiated AgNPs were observed to be more effective against E. coli. The results showed, that the diameter of zone of inhibition of visible light irradiated AgNPs against E. coli was 23 (±0.5)mm and in dark was 11 (±0.4)mm.

Changes in nutrient content of Cirsium arvense (L.) Scop. during the vegetation period.

Cirsium arvense /L/ Scop. nowadays is popular in all territory of Hungary, it can be found almost on every soil types. Cirsium arvense is one of the most difficulty eradicated weed of the fields, the ruderals, and also the roadsides. On the base of IV. Hungarian Weed Survey 1996-1997, it takes the fifth place in the dominance sequence of the weeds, with 1.8% average covering. In the interest of effective weed control we can know the biological characteristics of the weeds in detail. In our experiments we followed the nutrient uptake and its changing in Cirsium arvense plants. Nitrogen concentration of shoots altered between 1.5-3.6%. We established that plants can uptake potassium in a great quantity. Roots and shoots contained potassium in high concentration between 2.2-5.9%. The maximum of shoot production from the adventitious buds of the roots was in October and the minimum was in April and May.