Transgenerational plasticity in morphological characteristics and biomass of the invasive plant Xanthium strumarium.

Transgenerational plasticity (TGP) allows a plant to acclimate to external variable environments and is a potential mechanism that explains the range expansion and invasion success of some exotic plants. Most studies explored the traits of TGP associated with the success of exotic plant invasions by comparison studies among exotic, native, invasive, and noninvasive species. However, studies on the TGP of invasive plants in different resource environments are scarce, and the biological mechanisms involved are not well understood. This study aimed to determine the role of TGP in the invasiveness of Xanthium strumarium in northeast China. We measured the plant morphology of aboveground parts and the growth of three generations of the invader under different environmental conditions. The results showed that the intergenerational plasticity of X. strumarium was stronger under stress conditions. We found that the X. strumarium parent generation (F0) grown under water and/or nutrient deficiency conditions transferred the environmental information to their offspring (F1 and F2). The F1 generation grown under high-resource conditions has greater height with larger crown sizes, thicker basal diameters, and higher biomass. Both water and nutrients can affect the intergenerational transmission of plant plasticity, nutrients play a more important role compared with water. The high morphological intergenerational plasticity of X. strumarium under a pressure environment can help it quickly adapt to the new environment and accelerate the rapid expansion of the population in the short term. The root:shoot ratio and reproductive and nutrient distribution of the X. strumarium F0 and F1 generations showed high stability when the growth environment of the F0 generation differed from that of the F1 generation. The stable resource allocation strategy can ensure that the obtained resources are evenly distributed to each organ to maintain the long-term existence of the community. Therefore, the study of intergenerational transmission plasticity is of great significance for understanding the invasion process, mechanism, and prevention of invasive plants.

Phytoremediation potential of hybrids of the exotic plant Xanthium strumarium and its native congener Xanthium sibiricum for cadmium-contaminated soils.

Exotic plants could play an essential role in the restoration of heavy metal-contaminated soil. This study evaluated the tolerance of and extraction of cadmium (Cd) by ZCR (CR♀ × LT♂), hybrids of Xanthium strumarium (LT, exotic species) and X. sibiricum (CR, indigenous congener), and their parental species under different Cd treatments (0, 10, 40, and 80 mg·kg-1). The results showed that the hybrids had significantly improved tolerance to Cd. Under Cd stress, the biomass of ZCR increased by more than 50% on average compared with that of CR. Moreover, the hybrids showed a more remarkable ability to transport Cd from the root to the shoot. The Cd content of the shoots of ZCR increased by 128.33, 147.22, and 252.63% when treated with 10, 40, and 80 mg·kg-1 Cd, respectively. ZCR stored more than 70% of Cd in litter leaves, thereby reducing the toxic effects of Cd on photosynthesis and growth. The results showed that ZCR showed excellent Cd tolerance and enrichment in the presence of Cd. The hybrids of Xanthium strumarium and its native congener X. sibiricum may remediate soil Cd pollution.Novelty statementWith the changing world economy and increasing human activities, exotic plants have become a global issue of common concern to the international community. This study describes new findings on using hybrids of the exotic plant of Xanthium strumarium and its native congener Xanthium sibiricum for the restoration of cadmium-contaminated soils. Under Cd stress, the hybrids' biomass, tolerance, and ability to accumulate Cd were significantly higher than that of X. sibiricum, indicating that hybrids gained useful heavy metal extraction traits from X. strumarium.

New flavonoid glycosides from Xanthium strumarium with their protein tyrosine phosphatase 1B inhibitory activity.

Two new flavonoid glycosides named 6-hydroxy-3-methoxy-apigenin 7-O-α-ʟ-rhamnopyranoside (1) and 3-hydroxyl-apigenin 8-C-ß-ᴅ-xylopyranoside (2), along with five known compounds (3-7), were isolated from Xanthium strumarium. Their structures were elucidated on the basis of spectroscopic and physicochemical analyses. All compounds were evaluated for in vitro inhibitory activity against PTP1B. Among them, compounds 1 and 5 showed significant inhibitory activity on PTP1B with IC50 values of 11.3 ± 1.7 and 8.9 ± 0.7 µM, respectively.

Chromium Contamination from Tanning Industries and Phytoremediation Potential of Native Plants: A Study of Savar Tannery Industrial Estate in Dhaka, Bangladesh.

Tannery wastewater is a significant cause of chromium (Cr) contamination in land and water. This study assessed Cr contamination caused by the discharge of tannery wastewater in the Dhaleshwari River and identified possible native plants for phytoremediation of Cr. Water, soil and sediments samples were collected from upstream and downstream of the wastewater discharge channel of Savar tannery industrial estate situated on the bank of the river. Samples of root, stem, leaf and fruit of four selected plants (i.e., Eichhornia crassipes, Xanthium strumarium L., Cynodon dactylon, Croton bonplandianum Baill.) were also collected from those sampling points. The total Cr in acid digested samples were determined by flame atomic absorption spectrometry. High concentrations of Cr were detected in the water, soil and sediment samples collected near the wastewater discharge channel. Of all the plant species, Xanthium strumarium L. exhibited high translocation factors (TF) and bioconcentration factors (BCF) for Cr. Based on the findings of this study Xanthium strumarium L. is preferable as a native species for phytoremediation of Cr.

Natural product-based semisynthesis and biological evaluation of thiol/amino-Michael adducts of xanthatin derived from Xanthium strumarium as potential pesticidal agents.

Xanthatin, a natural sesquiterpene lactone, occurs as one of the major constituents of Xanthium plants (Compositae) and exhibits many important biological properties. To discover natural products-based pesticides, forty-nine Michael-type thiol/amino adducts of xanthatin were synthesized and characterized, while their pesticidal activities were investigated. Among them, compounds 2c, 2h, 2i, and 2t exhibited more potent antifungal activity against Botrytis cinerea (IC50 = 0.96, 0.38, 6.33, and 7.21 µg/mL, respectively) than xanthatin and the two commercial fungicides. Compounds 2t and 2u displayed broad-spectrum and excellent antifungal effects against all tested phytopathogenic fungi, while their IC50 values ranged from 7.21 to 75.88 µg/mL. Compounds 2a, 2f, 2l, 2m, 2v, 7c, 7e, 7h, 7i, and 7j showed moderate larvicidal activity against Plutella xylostella Linnaeus. Furthermore, compounds 2b, 7g, and 7h demonstrated significant ovicidal activity against P. xylostella with the LC50 values of 14.04, 10.00, and 11.95 mg/L, respectively. These findings suggest that thiol/amino appended in the C-13 position of xanthatin may improve antifungal and ovicidal activities for the derivatives. It was also noticed that the exocyclic double bond of xanthatin is crucial for its larvicidal activity. This work also provides some important hints for further design, synthesis, and structural modification of the xanthanolides sesquiterpene lactones toward development of the new environmentally friendly pesticides for sustainable agricultural production.

Influence of diesel fuel contamination on Xanthium strumarium L. germination and growth.

In this study, the effects of diesel fuel contamination on common cocklebur (Xanthium strumarium L.) seeds have been investigated. Five levels of contamination were used (0 g, 2.5 g, 5 g, 7.5 g, and 10 g diesel per 100 g of substrate). Germination was significantly reduced only at 7.5 g and 10 g diesel and the highest percentage germination (97%) was recorded at 5 g diesel. Diesel contamination caused a significant reduction in shoot length, but the decline began to be important at 7.5 g diesel. The root length was positively influenced by diesel fuel contamination, the shortest root (12.89 cm) was observed in the control and the longest (19.92 cm) at 5 g diesel. Xanthium strumarium seeds germinated successfully at different levels of contamination, its root length seemed to take advantage of the diesel fuel contamination and its shoot length was mostly affected by the high contamination levels. Therefore, we can propose this plant species as a potential candidate for the phytoremediation of sites contaminated with diesel. Furthermore, the results could help improve our understanding of the behavior of X. strumarium, and its ability to germinate and grow in different soil conditions.

Effects of manganese stress on phenology and biomass allocation in Xanthium strumarium from metalliferous and non-metalliferous sites.

Xanthium strumarium is an annual pseudometallophyte. To reveal the mechanisms of this species to adapt to metallicolous environmental conditions, phenological traits and biomass allocation of metallicolous and non-metallicolous populations of X. strumarium under six Mn2+ concentrations by pot culture experiments were performed. The results showed that both time to bolting and time to fruit setting in the metallicolous population were earlier than those in the non-metallicolous population. The number of flowers, fruits, seeds and 1000-seed weight in the metallicolous population were higher than those in the non-metallicolous population under Mn stress. Reproductive allocation and harvest index in the metallicolous population were higher than those in the non-metallicolous population. Furthermore, all the Mn concentrations in leaves, stems, roots, and fruits of the metallicolous population were higher than the counterparts of non-metallicolous population. These results suggested that metallicolous population had higher tolerance to Mn stress than non-metallicolous population, the earlier flowering and fruiting, and the enhancement in reproductive allocation may contribute to plant tolerance to Mn toxicity for X. strumarium.

Volatiles Profiling, Allelopathic Activity, and Antioxidant Potentiality of Xanthium Strumarium Leaves Essential Oil from Egypt: Evidence from Chemometrics Analysis.

The essential oil (EO) of Xanthium strumarium L. leaves (family: Asteraceae) was extracted by hydrodistillation, and then analyzed by gas chromatography-mass spectrometry (GC-MS). Forty-three essential compounds were identified. The sesquiterpenoids represented the major constituents (72.4%), including oxygenated (61.78%) and non-oxygenated (10.62%) sesquiterpenes, followed by monoterpenes (25.19%). The diterpenoids and oxygenated hydrocarbons were determined as minor compounds. The main constituents of the EO were 1,5-dimethyltetralin (14.27%), eudesmol (10.60%), l-borneol (6.59%), ledene alcohol (6.46%), (-)-caryophyllene oxide (5.36%), isolongifolene, 7,8-dehydro-8a-hydroxy (5.06%), L-bornyl acetate (3.77%), and aristolene epoxide (3.58%). A comparative analysis was stated here between the EO of Egyptian X. strumarium and those previously reported from Pakistan, Iran, and Brazil based on chemometic tools such as principal components analysis (PCA) and agglomerative hierarchical clustering (AHC). The EO of X. strumarium showed weak 1, 1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity with IC50 321.93 µL/L-1, which was comparable to ascorbic acid as a reference. However, the EO exhibited significant allelopathic potential regarding the germination and growth of the noxious weed Bidens pilosa in a concentration-dependent manner. Therefore, further study is recommended to characterize the EO from X. strumarium as an eco-friendly green bioherbicide against weeds, as well as determine their mode of actions.

Traditional Uses, Botany, Phytochemistry, Pharmacology, Pharmacokinetics and Toxicology of Xanthium strumarium L.: A Review.

Xanthium strumarium L. (Asteraceae) is a common and well-known traditional Chinese herbal medicine usually named Cang-Er-Zi, and has been used for thousands of years in China. The purpose of this paper is to summarize the progress of modern research, and provide a systematic review on the traditional usages, botany, phytochemistry, pharmacology, pharmacokinetics, and toxicology of the X. strumarium. Moreover, an in-depth discussion of some valuable issues and possible development for future research on this plant is also given. X. strumarium, as a traditional herbal medicine, has been extensively applied to treat many diseases, such as rhinitis, nasal sinusitis, headache, gastric ulcer, urticaria, rheumatism bacterial, fungal infections and arthritis. Up to now, more than 170 chemical constituents have been isolated and identified from X. strumarium, including sesquiterpenoids, phenylpropenoids, lignanoids, coumarins, steroids, glycosides, flavonoids, thiazides, anthraquinones, naphthoquinones and other compounds. Modern research shows that the extracts and compounds from X. strumarium possess wide-ranging pharmacological effects, including anti- allergic rhinitis (AR) effects, anti-tumor effects, anti-inflammatory and analgesic effects, insecticide and antiparasitic effects, antioxidant effects, antibacterial and antifungal effects, antidiabetic effects, antilipidemic effects and antiviral effects. However, further research should focus on investigating bioactive compounds and demonstrate the mechanism of its detoxification, and more reasonable quality control standards for X. strumarium should also be established.

Morphophysiological responses and tolerance mechanisms of Xanthium strumarium to manganese stress.

Effective phytoremediation of manganese (Mn) requires the careful selection of a species that has a relatively high manganese tolerance. Exploring the physiological mechanisms related to Mn stress responses is crucial for identifying and employing species for Mn phytoremediation. Xanthium strumarium is a species that can accumulate high levels of Mn, thus it is a candidate species for Mn-phytoremediation. To reveal the tolerance mechanisms of this species to manage Mn stress, the morphological, physiological, and biochemical responses of seedlings grown in water cultures under six different Mn concentrations were analyzed. The results showed that X. strumarium can accumulate high levels of Mn, even as plant growth was inhibited by rising Mn concentrations. Malondialdehyde (MDA) content increased and catalase (CAT) activity decreased along with the increased Mn concentrations, while soluble protein and proline content, as well as the superoxide dismutase (SOD) and peroxidase (POD) enzymes, all increased initially and then declined. The highest value of POD, SOD, soluble protein and proline all occurred at 5000 µM of Mn stress, which means that X. strumarium can adapt to low concentration of Mn stress. The net photosynthetic rate (Pn), stomatal conductance (Gs), intercellular CO2 concentration (Ci) and transpiration rate (Tr) decreased, and the stomatal limitation (Ls) increased in response to Mn stress. Furthermore, water use efficiency (WUE) and intrinsic water use efficiency (WUEi) increased first under low concentration of Mn, and then reduced as the concentration of Mn increased. The maximum quantum efficiency of PSII photochemistry (Fv/Fm), efficiency of excitation capture by open PSII reaction centers (Fv'/Fm'), electron transport rate (ETR) declined as Mn concentration increased. In conclusion, the above results showed that X. strumarium can be effectively used for phytoremediation of Mn-contaminated soils.

Xanthium strumarium L. seed hull as a zero cost alternative for Rhodamine B dye removal.

Treatment of polluted water has been considered as one of the most important aspects in environmental sciences. Present study explores the decolorization potential of a low cost natural adsorbent Xanthium strumarium L. seed hull for the adsorption of a toxic xanthene dye, Rhodamine B (RHB). The characterization of the adsorbent revealed the presence of high amount of carbon, when exposed to Electron Dispersive Spectroscopy (EDS). Further appreciable decolorization took place which was confirmed by Fourier Transform Infrared Spectroscopy (FTIR) analysis noticing shift in peaks. Isothermal studies indicated multilayer adsorption following Freundlich isotherm. The rate of adsorption was supported by second order kinetics directing a chemical phenomenon during the process with dominance of film diffusion as the rate governing step. Moreover paper aims at correlating the chemical arena to the mathematical aspect providing an in-depth information of the studied treatment process. For proper assessment and validation of the observed data, experimental data has been statistically treated by applying different error functions namely, Chi-square test (χ2), Sum of absolute errors (EABS) and Normalized standard deviation (NSD). Further practical applicability of the low cost adsorbent was evaluated by continuous column mode studies with 72.2% of dye recovery. Xanthium strumarium L. proved to be environment friendly low cost natural adsorbent for decolorizing RHB from aquatic system.

Identification and Functional Characterization of Sesquiterpene Synthases from Xanthium strumarium.

Xanthium strumarium synthesizes various pharmacologically active sesquiterpenes. The molecular characterization of sesquiterpene biosynthesis in X. strumarium has not been reported so far. In this study, the cDNAs coding for three sesquiterpene synthases (designated as XsTPS1, XsTPS2 and XsTPS3) were isolated using the X. strumarium transcriptome that we recently constructed. XsTPS1, XsTPS2 and XsTPS3 were revealed to have primary activities forming germacrene D, guaia-4,6-diene and germacrene A, respectively, by either ectopic expression in yeast cells or purified recombinant protein-based in vitro assays. Quantitative real-time PCRs and metabolite analysis for the different plant parts showed that the transcript abundance of XsTPS1-XsTPS3 is consistent with the accumulation pattern of their enzymatic products, supporting their biochemical functions in vivo. In particular, we discovered that none of the XsTPS2 product, guaia-4,6-diene, can be detected in one of the X. strumarium cultivars used in this study (it was named the Hubei-cultivar), in which a natural deletion of two A bases in the XsTPS2 cDNA disrupts its activity, which further confirmed the proposed biochemical role of XsTPS2 in X. strumarium in vivo.

Two new compounds from Xanthium strumarium.

One new lignan, fructusol A (1), and one new thiazine derivative, 2-hydroxy-xanthiazone (2), along with eight known ones, were isolated from the seeds of Xanthium strumarium. The structures of new compounds were elucidated on the basis of extensive spectroscopic methods. Meanwhile, compounds 1-3 were tested for their antifungal activities against Candida albicans (ATCC 10231) in vitro. No one showed obvious inhibitions (MIC90 > 128 µg/ml).

Xanthium strumarium as an Inhibitor of α-Glucosidase, Protein Tyrosine Phosphatase 1ß, Protein Glycation and ABTS⁺ for Diabetic and Its Complication.

Phytochemical investigation of the natural products from Xanthium strumarium led to the isolation of fourteen compounds including seven caffeoylquinic acid (CQA) derivatives. The individual compounds were screened for inhibition of α-glucosidase, protein tyrosine phosphatase 1ß (PTP1ß), advanced glycation end products (AGEs), and ABTS⁺ radical scavenging activity using in vitro assays. Among the isolated compounds, methyl-3,5-di-caffeoyquinic acid exhibited significant inhibitory activity against α-glucosidase (18.42 µM), PTP1ß (1.88 µM), AGEs (82.79 µM), and ABTS⁺ (6.03 µM). This effect was marked compared to that of the positive controls (acarbose 584.79 µM, sumarin 5.51 µM, aminoguanidine 1410.00 µM, and trolox 29.72 µM respectively). In addition, 3,5-di-O-CQA (88.14 µM) and protocatechuic acid (32.93 µM) had a considerable inhibitory effect against α-glucosidase and ABTS⁺. Based on these findings, methyl-3,5-di-caffeoyquinic acid was assumed to be potentially responsible for the anti-diabetic actions of X. strumarium.

Sesquiterpenes with TRAIL-resistance overcoming activity from Xanthium strumarium.

The ability of TRAIL to selectively induce apoptosis in cancer cells while sparing normal cells makes it an attractive target for the development of new cancer therapy. In search of bioactive natural products for overcoming TRAIL-resistance from natural resources, we previously reported a number of active compounds. In our screening program on natural resources targeting overcoming TRAIL-resistance, activity-guided fractionations of the extract of Xanthium strumarium led to the isolation of five sesquiterpene compounds (1-5). 11α,13-dihydroxanthinin (2) and 11α,13-dihydroxanthuminol (3) were first isolated from natural resources and xanthinosin (1), desacetylxanthanol (4), and lasidiol p-methoxybenzoate (5) were known compounds. All compounds (1-5) showed potent TRAIL-resistance overcoming activity at 8, 20, 20, 16, and 16 µM, respectively, in TRAIL-resistant AGS cells. Compounds 1 and 5 enhanced the levels of apoptosis inducing proteins DR4, DR5, p53, CHOP, Bax, cleaved caspase-3, cleaved caspase-8, and cleaved caspase-9 and also decreased the levels of cell survival protein Bcl-2 in TRAIL-resistant AGS cells in a dose-dependent manner. Compound 1 also enhanced the levels of DR4 and DR5 proteins in a time-dependent manner. Thus, compounds 1 and 5 were found to induce both extrinsic and intrinsic apoptotic cell death. Compound 1 also exhibit TRAIL-resistance overcoming activity in DLD1, DU145, HeLa, and MCF7 cells but did not decrease viability in non-cancer HEK293 cells up to 8 µM.

Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness in the field.

BACKGROUND AND AIMS: Stereochemical variation is widely known to influence the bioactivity of compounds in the context of pharmacology and pesticide science, but our understanding of its importance in mediating plant-herbivore interactions is limited, particularly in field settings. Similarly, sesquiterpene lactones are a broadly distributed class of putative defensive compounds, but little is known about their activities in the field. METHODS: Natural variation in sesquiterpene lactones of the common cocklebur, Xanthium strumarium (Asteraceae), was used in conjunction with a series of common garden experiments to examine relationships between stereochemical variation, herbivore damage and plant fitness. KEY RESULTS: The stereochemistry of sesquiterpene lactone ring junctions helped to explain variation in plant herbivore resistance. Plants producing cis-fused sesquiterpene lactones experienced significantly higher damage than plants producing trans-fused sesquiterpene lactones. Experiments manipulating herbivore damage above and below ambient levels found that herbivore damage was negatively correlated with plant fitness. This pattern translated into significant fitness differences between chemotypes under ambient levels of herbivore attack, but not when attack was experimentally reduced via pesticide. CONCLUSIONS: To our knowledge, this work represents only the second study to examine sesquiterpene lactones as defensive compounds in the field, the first to document herbivore-mediated natural selection on sesquiterpene lactone variation and the first to investigate the ecological significance of the stereochemistry of the lactone ring junction. The results indicate that subtle differences in stereochemistry may be a major determinant of the protective role of secondary metabolites and thus of plant fitness. As stereochemical variation is widespread in many groups of secondary metabolites, these findings suggest the possibility of dynamic evolutionary histories within the Asteraceae and other plant families showing extensive stereochemical variation.

Fractionation of Xanthium strumarium L. foliage phenolics, in-vitro antioxidant activities, and in-vivo anti-diabetic potential.

Introduction: The present research aimed to fractionate Xanthium strumarium L. (XSL) foliage phenolics into a set of solvents and evaluate their antioxidant potential and in-vivo anti-diabetic activity against Alloxan monohydrate-induced diabetic mice. Methodology: For this purpose, XSL foliage was fractionated into petroleum ether, ethyl acetate, ethanol, and water via orbital type shaking and tested for the presence of phenolics, and their antioxidant and antidiabetic potential. Results and discussion: The results revealed that the ethyl acetate fraction of XSL foliage contained the highest amount of total phenolics 95.25 mg GAE/g of extract, followed by ethanol (65.14 mg GAE/g), petroleum ether (25.12 mg GAE/g), water (12.20 mg GAE/g), and XSL powder (69.13 mg GAE/g). At the end of treatment time (day 18 of oral administration of 400 mg/kg body weight of mice), the ethyl acetate fraction significantly (p ≤ 0.05) lowered blood glucose level (353 ± 10.6 to 220 ± 25.5 mg/dL) which might due to the elevated level of phenolic compounds in this fraction. Conclusion: Overall, it can be speculated that ethyl acetate and ethanol may work efficiently for the enrichment of XSL phenolic without compromising their antidiabetic potential.

Green Synthesis and Characterization of Xanthium strumarium-Mediated Titanium Dioxide Nanoparticles.

Background Green synthesis of nanoparticles is a growing trend. The annual plant Xanthium strumarium L. (X. strumarium) belongs to the Asteraceae family. The herb has traditionally been used to treat a variety of ailments, including leucoderma, dangerous insect bites, epilepsy, salivation, allergic rhinitis, sinusitis, etc. Inorganic, biocompatible, and non-toxic titanium is a substance employed in the pharmaceutical and biomedical industries as well as in fields like bone tissue engineering. The aim of the study is to characterize titanium dioxide nanoparticles (TiO2NPs), which were synthesized from X.strumarium. Also, this study aims to assess the cytotoxic properties of the synthesized leaf extract and the TiO2NPs. Materials and methods In this study, the biosynthesis of TiO2NPs was made from X. strumarium leaf extract. The characterization of the green-synthesized TiO2NPs was done using the spectral analysis of an ultraviolet (UV)-visible spectrophotometer, scanning electron microscopy (SEM), and Fourier Transform Infrared Spectroscopy (FTIR). The advantage of using TiO2NPs is that they possess antimicrobial, antibacterial, chemical stability, and catalytic properties. The leaf extract and the biosynthesized nanoparticles were tested against human fibroblast cell lines for biocompatibility using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay.  Results SEM investigation showed that TiO2NPs were crystalline in nature. FTIR confirms the presence of alkyne and amine functional groups, and the pointed vertices in the X-ray diffraction (XRD) pattern show the crystalline nature of TiO2NPs. The study found that the cell viability of TiO2NPs was 110%. Conclusion TiO2NPs were synthesized from X. strumarium leaf extract and characterized using SEM, FTIR, and XRD. The TiO2NPs were found to be crystalline in nature with various functional groups. MTT assay shows that the synthesized nanoparticles are promising biocompatible agents that can be used in future research in the medical field.

Natural Sesquiterpene Lactone as Source of Discovery of Novel Fungicidal Candidates: Structural Modification and Antifungal Activity Evaluation of Xanthatin Derived from Xanthium strumarium L.

As part of our ongoing efforts to discover novel agricultural fungicidal candidates from natural sesquiterpene lactones, in the present work, sixty-three xanthatin-based derivatives containing a arylpyrazole, arylimine, thio-acylamino, oxime, oxime ether, or oxime ester moiety were synthesized. Their structures were well characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry, while the absolute configurations of compounds 5' and 6a were further determined by single-crystal X-ray diffraction. Meanwhile, the antifungal activities of the prepared compounds against several phytopathogenic fungi were investigated using the spore germination method and the mycelium growth rate method in vitro. The bioassay results illustrated that compounds 5, 5', and 15 exhibited excellent inhibitory activity against the tested fungal spores and displayed remarkable inhibitory effects on fungal mycelia. Compounds 5 and 5' exhibited more potent inhibitory activity (IC50 = 1.1 and 24.8 µg/mL, respectively) against the spore of Botrytis cinerea than their precursor xanthatin (IC50 = 37.6 µg/mL), wherein the antifungal activity of compound 5 was 34-fold higher than that of xanthatin and 71-fold higher than that of the positive control, difenoconazole (IC50 = 78.5 µg/mL). Notably, compound 6'a also demonstrated broad-spectrum inhibitory activity against the four tested fungal spores. Meanwhile, compounds 2, 5, 8, and 15 showed prominent inhibitory activity against the mycelia of Cytospora mandshurica with the EC50 values of 2.3, 11.7, 11.1, and 3.0 µg/mL, respectively, whereas the EC50 value of xanthatin was 14.8 µg/mL. Additionally, compounds 5' and 15 exhibited good in vivo therapeutic and protective effects against B. cinerea with values of 55.4 and 62.8%, respectively. The preliminary structure-activity relationship analysis revealed that the introduction of oxime, oxime ether, or oxime ester structural fragment at the C-4 position of xanthatin or the introduction of a chlorine atom at the C-3 position of xanthatin might be significantly beneficial to antifungal activity. In conclusion, the comprehensive investigation indicated that partial xanthatin-based derivatives from this study could be considered for further exploration as potential lead structures toward developing novel fungicidal candidates for crop protection.

Phytochemical investigation of the fruits of Xanthium strumarium and their cytotoxic activity.

Eight pentacyclic triterpenoids including two new ones (1, 2) were isolated from the fruits of Xanthium strumarium. Their structures were elucidated by extensive spectroscopic analysis. All isolates were evaluated for in vitro cytotoxic activity on HepG2, A549, HCT116 and SW480 cancer cells. Among them, the new compound 2 was found to exhibit significant cytotoxic activity on A549, HCT116 and SW480 cancer cells with IC50 values of 9.68, 4.27 and 7.58 µM, respectively. Further, 2 was selected for cell cycle analysis and results revealed that 2 could cause HCT116 cell cycle arrest in G1 phase. In addition, Annexin V-FITC/PI staining assay showed that 2 could induce the death of HCT116 cells.