Search Results (48)

Zanthoxylum caribaeum Lam. is a member of the Rutaceae Family that can be naturally found in South and central America (Brazil, Paraguay, Bolivia, Caribbean, etc.). Its traditional medicinal uses are well documented among native communities, such as that of the Guarani, in Paraguay. More than 60 metabolites, including alkaloids, terpenoids, coumarins, and alkylamides, have been identified in its leaves, bark, and fruits. The biological activities and mechanisms of action of several of these compounds, as well as those of crude extracts, have also been investigated by previous studies. As a medicinal and edible plant, Z. caribaeum shows promising applications in the pharmacological industry. For the last 25 years, a significant amount of research has been conducted with Z. caribaeum to better understand its toxicity and complex mechanisms of action, bringing science-based clinical safety to its traditional uses. This review integrates available knowledge chemical and biological data on this species. It emphasizes the diversity of bioactive metabolites, their associated bioactivities, and provides an updated overview of the plant’s advances in ethnopharmacology, phytochemistry, pharmacology, agricultural exploitation, and potential utilization. Full article

The tomato russet mite, Aculops lycopersici, is considered one of the most important crop pests globally. The main control strategy is based on synthetic acaricides; however, they create resistant strains and ecological risks. In this context, biopesticides could be a viable and sustainable alternative for eriophyid control. In the present study, the toxic effects of a N-alkylamides-enriched extract obtained from Acmella oleracea and of carlina oxide, the main bioactive component of Carlina acaulis, on A. lycopersici were evaluated, as well as their side effects on the phytoseiid Typhlodromus exhilaratus under laboratory conditions. Six concentrations were tested for each product against A. lycopersici adults (0, 320, 640, 1280, 2500, and 5000 μL L⁻¹), and the median concentration (1280 μL L⁻¹) was evaluated against eggs and females of the phytoseiid T. exhilaratus. Both the N-alkylamides-enriched extract and carlina oxide showed total lethal effects (100% of mortality) towards A. lycopersici at the two highest concentrations. Moderate-to-high mortality was also recorded with the lower concentrations: from 42.22 to 97.78%. Probit analysis identified LC₅₀ values of 205.32 μL L⁻¹ for carlina oxide and 253.79 μL L⁻¹ for the N-alkylamides-enriched extract, respectively. Carlina oxide showed a moderate ovicidal effect on T. exhilaratus eggs (50.00% hatching rate) on T. exhilaratus, and caused 39.13% mortality on females, whereas the N-alkylamides-enriched extract was less toxic, with a hatching rate of 88.00% and a mortality rate of 18.75% on females. In conclusion, carlina oxide and the N-alkylamides-enriched extract showed high toxicity on A. lycopersici, with a reduced effect on phytoseiid. These results highlight the potential of these products as sustainable means for the management of tomato russet mite. Full article

Background: Chemotherapy-induced neuropathic pain is a major side effect of antineoplastic treatment. This study investigated the neuroprotective potential of Acmella oleracea L. extracts containing the N-alkylamide spilanthol, phenolic acids, and glycosylated flavonoids. Methods: Hydroalcoholic extracts of aerial parts (AP) and roots (R) of in vitro seedlings were quali-quantitatively characterized by HPLC-DAD-MS and by ¹H-NMR. Different concentrations (15–150 µg/mL) of AP and R were tested in SH-SY5Y cells differentiated into neurons exposed to oxaliplatin (10 µM), assessing cell viability (MTT), cytotoxicity (LDH), SOD activity, and expression of ATF-3, Ire1α, and Nf-H genes. To evaluate the impact on neuropathic pain, CD-1 mice were treated intraperitoneally with oxaliplatin (2.4 mg/kg), the effect of AP and R extracts (200–1200 mg/kg) were measured by the cold plate test. Results: AP extract was rich in phenols and alkylamides, whereas R extract showed higher phenolic levels but lower alkylamides content. Both extracts significantly reduced mortality and cytotoxicity and counteracted oxidative imbalance by enhancing SOD activity. Gene expression analysis confirmed their neuroprotective effects. In vivo, oxaliplatin induced a 50% reduction in pain threshold, while acute treatment with AP and R extracts dose-dependently alleviated neuropathic pain. Despite the lower spilanthol content in R extract, its efficacy was comparable to AP, suggesting an important role of phenolic compounds. Conclusions: Extracts from both aerial parts and roots of A. oleracea show promise in alleviating chemotherapy-induced neuropathy through mechanisms not solely related to spilanthol. Further studies to elucidate the contribution of phenolic components are desirable. Full article

Plastics pollution is a critical global environmental issue, with growing concern over the increasing presence of nanoplastic particles. Plastics are major environmental pollutants that adversely affect human health, particularly when plastics from food sources enter the body and pose potential risks to reproductive health. Echinacea purpurea is an immunologically active medicinal plant containing phenolic acids and alkylamides. Nanoparticles present a promising approach to enhance the effectiveness, stability, and bioavailability of Echinacea purpurea ethanol extract (EE) active components. This study aimed to determine the protective effects of chitosan-silica-Echinacea purpurea nanoparticles (CSE) against reproductive injury induced by polystyrene nanoplastics (PS-NPs) in male rats. The results showed that CSE dose-dependently reduced oxidative damage and protected intestinal and reproductive health. Furthermore, CSE improved gut microbiota dysbiosis, preserved barrier integrity, and attenuated PS-NPs-induced inflammation in the colon, brain, and gonads. Inflammatory factors released from the gut can enter the bloodstream, cross the blood–brain barrier, and potentially modulate the hypothalamic–pituitary–gonadal (HPG) axis. CSE has also been shown to elevate neurotransmitter levels in the colon and brain, thereby repairing HPG axis dysregulation caused by PS-NPs through gut–brain communication and improving reproductive dysfunction. This study enhances our understanding of CSE in modulating the gut–brain and HPG axes under PS-NPs-induced damage. CSE demonstrates the capacity to provide protection and facilitate recovery by mitigating oxidative stress and inflammation, restoring gut microbiota balance, and preserving hormone levels in the context of PS-NPs-induced injury. Full article

Affinin (spilanthol) is the main bioactive alkylamide present in Heliopsis longipes roots, exerting antinociceptive and anti-inflammatory effects that involve the activation of TRP channels. Previous studies indicated that affinin reduces the LPS-induced increase in pro-inflammatory cytokine production in murine macrophages. However, no studies have evaluated whether affinin produces antinociceptive, anti-inflammatory, and behavioral effects in experimental animals treated with LPS, nor has the mechanism of action involved in these pharmacological effects been established. The present study evaluated whether affinin induces hypothermia, catalepsy, hypolocomotion, and analgesia and, moreover, whether the analgesia involves the activation of the CB1 cannabinoid receptor and TRPV1 and TRPA1 channels. Subsequently, the anti-inflammatory activity and behavioral effects induced by affinin (20 mg/kg) in mice were evaluated via LPS (2.5 mg/kg)-induced hypothermia. The results of the experiments indicate that the analgesic effect of affinin involves the activation of the CB1 cannabinoid receptors and the TRPV1 and TRPA1 channels. Additionally, affinin reduced the severity of LPS-induced hypothermia and attenuated the increase in TNF-α and IL-6 levels in serum. The results obtained demonstrate that affinin induces antinociceptive, anti-hypothermic, and anti-inflammatory activities, which involve the CB1 receptor and the TRPV1 and TRPA1 channels and the suppression of pro-inflammatory cytokines. Full article

Background/Objectives: Natural products are gaining increasing importance due to the large variety of biological activities exerted by their constituents. Among these, the products deriving from Acmella oleracea (L.) R.K. Jansen can be exploited for their local anaesthetic, myorelaxant, anti-inflammatory/analgesic, and antifungal properties. In this regard, there is a need to develop novel formulations for the topical delivery of A. oleracea-derived extracts to widen their use in the pharmaceutical and cosmetic fields. Methods: Nanoformulations, i.e., nanoemulsions (NEs) and microemulsions (MEs), were investigated as a strategy to encapsulate an extract from A. oleracea at the nanoscale level in water and then incorporated into xanthan gum-based hydrogels. Results: Only NEs provided a physically stable formulation, while the precipitation of solid hydrophobic components from the extract was observed during ME preparation under all tested conditions despite the use of ethyl oleate as an oily co-solvent. The optimized NE-based hydrogel remained physically stable over six months, as confirmed by rheological measurements and polarized optical microscope observation, without a phase separation phenomenon. Therefore, NEs resulted more suitable nanodispersed systems than MEs for the encapsulation of A. oleracea extract, which contains a large amount of hydrophobic constituents that are solid at room temperature. Furthermore, the sustained spilanthol release across an artificial membrane (Franz cell apparatus) and the cytotoxic profile on HaCaT cell line support its potential topical application. Conclusions: The outcomes of this study provided valuable insights into the formulation of A. oleracea extract, broadening its fields of applicability, including topical administration. Full article

Acmella oleracea (L.) R.K. Jansen, also called jambù, is a medicinal and aromatic plant native to the Brazilian Amazon rainforest and phytochemically characterized by N-alkylamides with spilanthol as the main active compound. Jambù recently attracted the interest of many companies because of its wide range of pharmaceutical, nutraceutical, and cosmetic applications. In this context, it is desirable to identify eco-friendly cultivation methods that not only minimize the environmental footprint but also support the biosynthesis of the plant’s valuable bioactive compounds. The zero-discharge approach of aquaponics makes this growing system an eco-friendly and sustainable production strategy for crops. Thus, a greenhouse experiment was conducted on two jambù cultivars, i.e., cv ‘purple’ and cv ‘yellow’, grown in aquaponic and hydroponic systems. The objective was to compare their contents of N-alkylamides, their numbers of capitula, which are the main source of these bioactives, and their volatile profiles. The results highlighted differences between the two cultivars and among plants harvested at different periods. Interestingly, aquaponics yielded plants with a high N-alkylamide content, which was comparable to that obtained with hydroponics. Overall, this study highlighted the feasibility of adopting aquaponics to grow A. oleracea, paving the way for circular economy-based and sustainable agricultural practices. Full article

This study investigates the transformation of Acmella oleracea with the Agrobacterium rhizogenes rolC gene and evaluates its impact on phytochemical composition and biological activity. A total of 480 plant nodes were subjected to Agrobacterium−mediated transformation, leading to the regeneration of 35 putative transgenic plants. Molecular analysis confirmed the presence of the rolC transgene in 17 clones, of which four (C123, C127, C129, and C132) exhibited rolC mRNA expression. Phytochemical profiling of hydroalcoholic extracts of aerial parts (AP) and roots (R) revealed significant differences (p ≤ 0.05) between transgenic and non-transgenic plants (CTR). Compared to non−transgenic plants, transgenic AP exhibited lower total phenolic content but retained or increased flavonoid concentrations, particularly flavan−3−ols, whereas R extracts consistently showed reduced secondary metabolite levels. LC−DAD−ESI−MS analysis identified a diverse metabolite profile, with AP being notably rich in flavonoids (48.65%) and alkylamides (32.43%), including spilanthol. Functional assessments across antioxidant and anti−inflammatory assays demonstrated that R extracts exhibited stronger bioactivity compared to AP extracts, as indicated by lower IC₅₀ values (0.004–2.18 mg/mL for R vs. 0.007–7.24 mg/mL for AP). However, iron−chelating capacity was higher in AP extracts, correlating with flavonoid concentration. Hierarchical clustering confirmed that transgenic lines C123 and C127 most closely resembled the control, while C129 and C132 displayed distinct metabolic profiles. These findings highlight rolC’s role in modulating secondary metabolite synthesis, influencing both the phytochemical composition and functional properties of A. oleracea extracts. Full article

Ceiba (syn. Chorisia) trees have attracted multifaceted attention not only due to their ornamental and economic value but also for their remarkable metabolic diversity and therapeutic properties. In view of that, this work explores the chemical composition of Ceiba chodatii Hassl. and its biological potential. Overall, GC–MS-based analysis of the lipoidal constituents of C. chodatii flowers revealed the presence of diverse classes of metabolites that were dominated by long-chain aliphatic esters (77.016%), ketones (6.396%), aliphatic hydrocarbons (5.757%), fatty alcohols (3.718%), aromatic acid esters (2.794%), alkylamides (1.58%), aldehydes (1.035%), aromatic hydrocarbons (0.31%), and ethers (0.29%). In addition, repeated chromatographic fractionation of different fractions of the total alcoholic extract of the flowers afforded 13 metabolites of varied structural types, including fatty esters and alcohols, phytosterols, monoglycerides, furanoids, and flavonoid glycosides. Structures of the obtained compounds were determined by different spectroscopic techniques, such as 1H- and 13C-NMR, APT, DEPT, and EI–MS analyses. Noteworthily, a wide range of the metabolites identified herein using different analytical approaches were described for the first time in the plant species under study or in those belonging to the genus Ceiba. Finally, the total extract and different fractions of C. chodatii flowers as well as the isolated flavonoids showed weak anti-infective potential against a group of human pathogens at concentration ranges up to 200 and 20 µg/mL, respectively. In contrast, the total extract and different fractions of the flowers exerted mild to moderate anti-proliferative activities against MDA-MB-468 cells, with IC₅₀ in the range of 21.69–47.60 μg/mL. Full article

Echinacea purpurea is a perennial medicinal herb with important immunomodulatory and anti-inflammatory properties, especially purported for the alleviation of cold and flu symptoms. Different classes of secondary metabolites of the plant, such as alkylamides, caffeic acid derivatives, polysaccharides, flavonoids, and glycoproteins, are believed to be biologically and pharmacologically active. Although previous research suggests that the alkylamides present in Echinacea may be responsible for reducing the symptoms associated with the common cold or flu through their immunomodulatory activity, the roles of specific alkylamides and their targets (i.e., immune and/or antiviral) have not been well-elucidated or established. This study tested the antiviral and cytokine regulatory activity of various specific alkylamides that are present predominantly in Echinacea root extracts and found that one specific alkylamide, Dodeca-2E,4E-Dienoic acid isobutylamide, had potent antiviral activity against rhinovirus (the causative agent of most common colds) and influenza virus, as well as potent inhibition of IL-8 cytokine production. IL-8 is responsible for many of the symptoms associated with the common cold and is upregulated in other common respiratory infections. The broad activity and low cytotoxicity of this specific alkylamide support its potential use for treating rhinovirus and influenza virus infections. Full article

Spilanthol is a major N-alkylamide constituent of Acmella oleracea (L.) R.K. Jansen with diverse pharmacological properties. We recently showed the applicability of NADES (natural deep eutectic solvents) for the green extraction of spilanthol. However, the purification of targets from NADES poses a challenging step due to their non-volatility. A simple green method to retrieve spilanthol with minimal instrumental effort was devised, fractioning NADES (choline chloride/methylurea, choline chloride/1,2-propanediol, choline chloride/citric acid) and dry ethanolic extracts by SPE on C18 material, eluting merely with ethanolic solutions. The relative distribution of spilanthol and organic adulteration in SPE fractions were detected by HPLC-DAD, followed by scale-up, quantification and purity determination in an NMR-based approach. Isocratic elution with 52% ethanol (v/v) proved suitable in all experiments. The three purest 10 mL fractions combined yielded 12.21 mg spilanthol at 71.65% purity from NADES extract ChCl/P (choline chloride/1,2-propanediol, molar ratio 1:2, +20% m/m water). Ethanolic extract samples showed purities ranging from 77.27 to 80.27% in combined raw fractions. For all samples, purity increased by removing non-soluble substances from organic solutions. Pooled NADES extract fractions showed 89.71% in final samples, ethanolic extracts 87.25 to 91.93%. The highest purities of individual fractions per extract were 89.23 to 94.15%. This cheap and simple purification process is promising to acquire spilanthol for research purposes or as a sample preparation step before HPLC on a semi-preparative to preparative scale, as the substance is highly priced and scarcely available on the market. Organic solvents can be reused, and preliminary scale-up possibilities are shown. Full article

Common wheat (Triticum aestivum L.) is one of the most valuable cereal crops worldwide. This study examined leaf extracts of 30 accessions of T. aestivum and its subspecies using 48 h maceration with methanol by GC-MS and GCxGC-MS. The plants were grown from seeds of the wheat genetics collection of the Wheat Genetics Sector of the Institute of Cytology and Genetics, SB RAS. The analysis revealed 263 components of epicuticular waxes, including linear and branched alkanes, aliphatic alcohols, aldehydes, ketones, β-diketones, carboxylic acids and their derivatives, mono- and diterpenes, phytosterols, and tocopherols. Hierarchical cluster analysis and principal component analysis were used to identify and visualize the differences between the leaf extracts of different wheat cultivars. Three clusters were identified, with the leading components being (1) octacosan-1-ol, (2) esters of saturated and unsaturated alcohols, and (3) fatty acid alkylamides, which were found for the first time in plant extracts. The results highlight the importance of metabolic studies in understanding the adaptive mechanisms and increasing wheat resistance to stress factors. These are crucial for breeding new-generation cultivars with improved traits. Full article

Polytetrafluoroethylene (PTFE) and, by extension, fluoropolymers are ubiquitous in science, life, and the environment as perfluoroalkyl pollutants (PFAS). In all cases, it is difficult to transform these materials due to their chemical inertness. Herein, we report a direct amination process of PTFE and some fluoropolymers such as polyvinylidene fluoride (PVDF) and Nafion by lithium alkylamide salts. Synthesizing these reactants extemporaneously between lithium metal and an aliphatic primary di- or triamine that also serves as a solvent leads to the rapid nucleophilic substitution of fluoride by an alkylamide moiety when in contact with the fluoropolymer. Moreover, lithium alkylamides dissolved in suitable solvents other than amines can react with fluoropolymers. This highly efficient one-pot process opens the way for further surface or bulk modification if needed, providing an easy, inexpensive, and fast experiment protocol on large scales. Full article

For centuries, medicinal plants have been used as sources of remedies and treatments for various disorders and diseases. Recently, there has been renewed interest in these plants due to their potential pharmaceutical properties, offering natural alternatives to synthetic drugs. Echinacea, among the world’s most important medicinal plants, possesses immunological, antibacterial, antifungal, and antiviral properties. Nevertheless, there is a notable lack of thorough information regarding the echinacea species, underscoring the vital need for a comprehensive review paper to consolidate existing knowledge. The current review provides a thorough analysis of the existing knowledge on recent advances in understanding the physiology, secondary metabolites, agronomy, and ecology of echinacea plants, focusing on E. purpurea, E. angustifolia, and E. pallida. Pharmacologically advantageous effects of echinacea species on human health, particularly distinguished for its ability to safeguard the nervous system and combat cancer, are discussed. We also highlight challenges in echinacea research and provide insights into diverse approaches to boost the biosynthesis of secondary metabolites of interest in echinacea plants and optimize their large-scale farming. Various academic databases were employed to carry out an extensive literature review of publications from 2001 to 2024. The medicinal properties of echinacea plants are attributed to diverse classes of compounds, including caffeic acid derivatives (CADs), chicoric acid, echinacoside, chlorogenic acid, cynarine, phenolic and flavonoid compounds, polysaccharides, and alkylamides. Numerous critical issues have emerged, including the identification of active metabolites with limited bioavailability, the elucidation of specific molecular signaling pathways or targets linked to echinacoside effects, and the scarcity of robust clinical trials. This raises the overarching question of whether scientific inquiry can effectively contribute to harnessing the potential of natural compounds. A systematic review and analysis are essential to furnish insights and lay the groundwork for future research endeavors focused on the echinacea natural products. Full article

Antimicrobial peptides (AMPs) have recently attracted attention as promising antibacterial agents capable of acting against resistant bacterial strains. In this work, an approach was applied, consisting of the conjugation of a peptide related to the sequences of bactenecin 7 (Bac7) and oncocin (Onc112) with the alkyl(triphenyl)phosphonium (alkyl-TPP) fragment in order to improve the properties of the AMP and introduce new ones, expand the spectrum of antimicrobial activity, and reduce the inhibitory effect on the eukaryotic translation process. Triphenylphosphonium (TPP) derivatives of a decapeptide RRIRPRPPYL were synthesized. It was comprehensively studied how the modification of the AMP affected the properties of the new compounds. It was shown that while the reduction in the Bac7 length to 10 a.a. residues dramatically decreased the affinity to bacterial ribosomes, the modification of the peptide with alkyl-TPP moieties led to an increase in the affinity. New analogs with structures that combined a decapeptide related to Bac7 and Onc112—Bac(1–10, R/Y)—and TPP attached to the C-terminal amino acid residue via alkylamide linkers, inhibited translation in vitro and were found to be more selective inhibitors of bacterial translation compared with eukaryotic translation than Onc112 and Bac7. The TPP analogs of the decapeptide related to Bac7 and Onc112 suppressed the growth of both Gram-negative bacteria, similar to Onc112 and Bac7, and Gram-positive ones, similar to alkyl-TPP derivatives, and also acted against some resistant laboratory strains. Bac(1–10, R/Y)-C2-TPP, containing a short alkylamide linker between the decapeptide and TPP, was transferred into the E. coli cells via the SbmA transporter protein. TPP derivatives of the decapeptide Bac(1–10, R/Y) containing either a decylamide or ethylamide linker caused B. subtilis membrane depolarization, similar to alkyl-TPP. The Bac(1–10, R/Y)-C2-TPP analog was proven to be non-toxic for mammalian cells using the MTT test. Full article