Search Results (17)

Salicylic acid (SA) is involved in plant defense responses to environmental stressors by modulating gene expression and specialized metabolites production, enhancing plant adaptive resilience through systemic signaling pathways. This study investigates the impact of exogenous application of SA on the metabolism of iridoids and phenolic compounds—characteristic specialized metabolites of the Nepeta species, associated with diverse biological activities. Nepetalactone (NL) is a characteristic monoterpene iridoid, while rosmarinic acid (RA) represents the most abundant phenolic compound within the genus. We explored the effects of varying SA concentrations (2 µM, 5 µM, 10 µM, and 20 µM) on iridoid and phenolic metabolism in in vitro-grown Nepeta nuda, following 7 days and 28 days of elicitation. A significant increase in trans,trans-NL content was observed after 7-day exposure to 2 µM SA, while prolonged exposure led to a decrease in its levels, particularly at higher SA concentrations. Gene expression analysis revealed that 7 days of exposure to lower concentrations of SA upregulated genes coding for NAD-dependent nepetalactol-related short-chain dehydrogenase/reductases (NEPSs), key regulatory enzymes catalyzing the final steps of NL biosynthesis. In contrast, prolonged exposure to 20 µM SA downregulated genes coding for geraniol 8-hydroxylase (NnG8H) and 8-hydroxygeraniol oxidoreductase (Nn8HGO), which resulted in reduced iridoid content. Conversely, SA treatment notably increased RA content after prolonged exposure to 20 µM SA, which is a result of the enhanced expression of all analyzed RA biosynthesis-related genes. These findings demonstrate that both concentration and duration of SA treatment are critical determinants of elicitation outcomes in N. nuda. Strategic manipulation of these parameters can redirect metabolic flux toward either iridoid or phenolic compounds production, and enhance biotechnological production of specialized metabolites in N. nuda. Full article

Nepetalactone (NL) is a volatile iridoid monoterpene widely used in biopesticidal and repellent applications, yet its toxicokinetic behavior and metabolic fate as a pure compound remain poorly characterized. This study aimed to provide an integrated toxicokinetic evaluation of NL by combining in silico absorption, distribution, metabolism, excretion and toxicity (ADMET) modeling with in vitro metabolism assays using rat and human liver microsomes, supported by UHPLC–MS/MS analysis for metabolite identification. The in silico biotransformation predicted extensive phase I oxidation followed by phase II conjugation, while ADMET predictions indicated low systemic persistence and limited toxicological concern for most metabolites. The performed in vitro microsomal assays confirmed the in silico prediction by a rapid and time-dependent NL metabolism via both oxidative (86% reduction in NL concentration after 120 min) and conjugative (89% reduction in NL concentration after 120 min) pathways in rat and human systems, with comparable depletion kinetics between species. UHPLC–MS/MS enabled the identification of multiple phase I and phase II metabolites, pointing to pronounced interspecies differences in conjugative metabolism. In this sense, while oxidoreduction and hydrolysis reactions were consistent with previously reported iridoid metabolism. This study suggests the possible formation of previously unreported amino acid-related derivatives, although these require further confirmation. Overall, these findings advance the understanding of NL biotransformation, propose a new, previously unknown, metabolic pathway for iridoids, and provide relevant data to support human health and environmental risk assessment frameworks. Full article

The reliance on synthetic repellents such as N,N-diethyl-meta-toluamide (DEET) has raised health and environmental concerns, prompting the search for safer, plant-based alternatives. Catnip (Nepeta cataria L.), a rich source of iridoid monoterpenes, particularly nepetalactones, known for strong insect-repellent activity. However, their efficient extraction and molecular mechanisms in insect inhibition remains challenging. This study examined the chemical composition, protein–ligand interactions, and safety profiles of nepetalactones in comparison with DEET, with particular focus on mosquito odorant-binding proteins (OBPs) from Anopheles gambiae (AgamOBP), Culex quinquefasciatus (CquiOBP), and Aedes aegypti (AaegOBP). GC–MS/MS analysis identified nepetalactone isomers as the predominant constituents in catnip extracts obtained via steam distillation and olive oil extraction from dried leaves. Molecular docking results indicated that cis,cis-, cis,trans-, and nepetalactone isomers exhibited higher binding affinities toward the target OBPs than DEET. Furthermore, molecular dynamics simulations confirmed that all nepetalactone–OBP complexes exhibited stable conformations characterized by low average RMSD values and persistent hydrogen bond formation. Notably, cis,trans-NL–AaegOBP, NL–AaegOBP, and cis,cis-NL–AgamOBP complexes displayed lower binding free energies (ΔG_MM-PBSA) compared to DEET. These findings suggest that nepetalactones stabilize OBP–ligand interactions while inducing subtle conformational flexibility, potentially disrupting mosquito odorant recognition in a manner distinct from DEET. ADMET predictions indicated that nepetalactones exhibit favorable absorption, distribution, and safety profiles with reduced predicted toxicity compared to DEET. Collectively, these results establish nepetalactones as promising candidates for the development of effective, safe, and sustainable plant-based repellents. Full article

The study characterized the essential oils of eight aromatic medicinal plants (Tagetes filifolia, Aloysia citrodora, Cymbopogon citratus, Eucalyptus globulus, Chamaemelum nobile, Piper aduncum, Minthostachys mollis, and Rosmarinus officinalis) using Raman spectroscopy and gas chromatography–mass spectrometry (GC–MS). Raman spectra allowed the identification of bands associated with C–H, C=C, C–O, and C=O bonds, evidencing the presence of monoterpenes, sesquiterpenes, and oxygenated compounds. GC–MS analysis confirmed these results, detecting 224 compounds, predominantly terpenoids. Among the major compounds, cis,cis-nepetalactone (30.16%), β-caryophyllene (up to 18.26%), citronellol (10.92%), citral, and linalool were found. The combination of both techniques made it possible to relate the chemical composition to the molecular structure. This showed that the differences between species are mainly due to the proportion of oxygenated compounds (citral, linalool, geraniol) compared with aromatic hydrocarbons (β-caryophyllene, D-limonene, β-pinene). Additionally, the presence of cis,cis-nepetalactone in M. mollis was reported for the first time, representing a significant chemical finding. Full article

Light quality and duration profoundly influence the growth and productivity of plant species. This study investigated the effects of a blue–red LED light combination, known to induce flowering, on the physiological state and content of biologically active substances in catmint (Nepeta nuda L.) grown under controlled in vitro conditions. White light (W) was used as a control and compared with two blue–red intensities: BR (high-intensity blue–red light) and BRS (low-intensity blue–red light or “BR with shadow”). BR-treated plants showed increased leaf area, mesophyll thickness, biomass and starch content but reduced levels of plastid pigments. BR also modified the oxidative state of plants by inducing lipid peroxidation while simultaneously activating ROS scavenging mechanisms and enhancing phenolic antioxidants. Interestingly, BR decreased the accumulation of the Nepeta sp.-specific iridoid, nepetalactone. These effects appear to be regulated by the phytohormones auxin, abscisic acid and jasmonates. BRS treatment produced effects similar to the W control but led to increased plant height and reduced leaf area and thickness. Both BR and BRS regimes induced the accumulation of proteins and amino acids. We conclude that blue–red light can enhance the survival capacity of micropropagated N. nuda during subsequent soil adaptation, suggesting that similar light pre-treatment could improve plant performance under stress conditions. Full article

Lemon catnip (Nepeta cataria var. citriodora) is an underutilized aromatic and medicinal plant known for its high essential oil yield and distinctive lemon-like scent, and is widely used in the pharmaceutical, cosmetic, food, and biopesticide industries. Unlike typical catnip, it lacks nepetalactones and is rich in terpene alcohols, such as nerol and geraniol, making it a promising substitute for lemon balm. Despite its diverse applications, little attention has been paid to the valorization of byproducts from essential oil distillation, such as hydrolates and their secondary recovery oils. This study aimed to thoroughly analyze the volatile compound profiles of the essential oil from Lemon catnip and the recovery oil derived from its hydrolate over three consecutive growing seasons, with particular emphasis on how temperature and precipitation influence the major volatile constituents. The essential oil was obtained via semi-industrial steam distillation, producing hydrolate as a byproduct, which was then further processed using a Likens–Nickerson apparatus to extract the recovery oil, also known as secondary oil. Both essential and recovery oils were predominantly composed of terpene alcohols, with nerol (47.5–52.3% in essential oils; 43.5–54.3% in recovery oils) and geraniol (25.2–27.9% in essential oils; 29.4–32.6% in recovery oils) as the primary components. While sesquiterpene hydrocarbons were mostly confined to the essential oil, the recovery oil was distinguished by a higher presence of monooxygenated and more hydrophilic terpenes. Over the three-year period, elevated temperatures led to increased levels of geraniol, geranial, neral, and citronellal in both oils, whereas cooler conditions favored the accumulation of nerol and linalool, especially in the recovery oils. Higher precipitation was associated with elevated concentrations of nerol and linalool but decreased levels of geraniol, geranial, and neral, possibly due to dilution or degradation processes. Full article

Many specialized metabolites found in plants have significant potential for developing environmentally friendly weed management solutions. This review focuses on the phytotoxic effects of volatile terpenes and phenolic compounds, particularly nepetalactone, an iridoid monoterpenoid from Nepeta species, and phloretin, a dihydrochalcone predominantly found in the genus Malus. We highlight current findings on their herbicidal effects, including morphological, physiological, and biochemical responses in target plants. These results underscore their potential for developing sustainable herbicides that could control weeds with minimal environmental impact. We also discuss their soil persistence and methods to enhance their solubility, chemical stability, and bioavailability. Additionally, the possible effects on non-target organisms, such as pollinators, non-pollinating insects, and soil microbiota, are considered. However, further research and a deeper understanding of their long-term ecological impact, along with a resistance development risk assessment, is essential for the potential development of bioherbicides that could be applied in sustainable weed management practices. Full article

Catnip (Nepeta cataria L.) plants produce a wide array of specialized metabolites with multiple applications for human health. The productivity of such metabolites, including nepetalactones, and natural insect repellents is influenced by the conditions under which the plants are cultivated. In this study, we assessed how field-grown catnip plants, transplanted after being propagated via either single-node stem cuttings or seeds, varied regarding their phytochemical composition throughout a growing season in two distinct environmental conditions (Pittstown and Upper Deerfield) in the state of New Jersey, United States. Iridoid terpenes were quantified in plant tissues via ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry (UHPLC-QqQ-MS), and phenolic compounds (phenolic acids and flavonoids) were analyzed via UHPLC with diode-array detection (UHPLC-DAD). The highest contents of total nepetalactones in Pittstown were found at 6 weeks after transplanting (WAT) for both seedlings and cuttings (1305.4 and 1223.3 mg/100 g, respectively), while in Upper Deerfield, the highest contents for both propagules were at 11 WAT (1247.7 and 997.1 mg/100 g, respectively) for seed-propagated and stem cuttings). The highest concentration of nepetalactones was associated with floral-bud to partial-flowering stages. Because plants in Pittstown accumulated considerably more biomass than plants grown in Upper Deerfield, the difference in nepetalactone production per plant was striking, with peak productivity reaching only 598.9 mg per plant in Upper Deerfield and 1833.1 mg per plant in Pittstown. Phenolic acids accumulated in higher contents towards the end of the season in both locations, after a period of low precipitation, and flavone glycosides had similar accumulation patterns to nepetalactones. In both locations, rooted stem cuttings reached their maximum nepetalactone productivity, on average, four weeks later than seed-propagated plants, suggesting that seedlings have, overall, better agronomic performance. Full article

Nepeta nuda L. is a medicinal plant enriched with secondary metabolites serving to attract pollinators and deter herbivores. Phenolics and iridoids of N. nuda have been extensively investigated because of their beneficial impacts on human health. This study explores the chemical profiles of in vitro shoots and wild-grown N. nuda plants (flowers and leaves) through metabolomic analysis utilizing gas chromatography and mass spectrometry (GC–MS). Initially, we examined the differences in the volatiles’ composition in in vitro-cultivated shoots comparing them with flowers and leaves from plants growing in natural environment. The characteristic iridoid 4a-α,7-β,7a-α-nepetalactone was highly represented in shoots of in vitro plants and in flowers of plants from nature populations, whereas most of the monoterpenes were abundant in leaves of wild-grown plants. The known in vitro biological activities encompassing antioxidant, antiviral, antibacterial potentials alongside the newly assessed anti-inflammatory effects exhibited consistent associations with the total content of phenolics, reducing sugars, and the identified metabolic profiles in polar (organic acids, amino acids, alcohols, sugars, phenolics) and non-polar (fatty acids, alkanes, sterols) fractions. Phytohormonal levels were also quantified to infer the regulatory pathways governing phytochemical production. The overall dataset highlighted compounds with the potential to contribute to N. nuda bioactivity. Full article

Catnip (Nepeta cataria L.) is of scientific interest largely due to the production of nepetalactones, volatile iridoid terpenes with strong arthropod repellent activity. However, the plant can also produce other bioactive volatile iridoids, such as nepetalic acid (NA), nepetalactam (NT) and dihydronepetalactone (DHNL) that have not been studied extensively. Germplasm studies on plants that can produce such compounds are scarce. The present study evaluated the chemical diversity of catnip genotypes with a focus on NA, NT and DHNL. A total of 34 genotypes were harvested at different times over two years. The ethanolic extract of the plants was screened for iridoids by ultra-high-performance liquid chromatography/triple quadrupole mass spectrometry. CR9 × CR3 genotype had the highest value for biomass yield, while cultivar CR9 had the highest value for accumulated NA. Genotype UK.2 had the highest value for accumulated NT yield and CR5 had the highest value for accumulated DHNL. Overall, patented cultivars and elite selections performed better than other less studied genotypes. Harvest time influenced the accumulation of secondary metabolites differentially for the genotypes. This is the first germplasm study with a focus on these iridoid compounds, yet more studies are necessary as genotype characterization is essential for breeding and standardization of products for industry. Full article

Agastache rugosa (baechohyang) is one of the most important aromatic plants native to the Republic of Korea. A. rugosa fragrance has been used to prepare incense since the Goryeo Dynasty in Korea. The present study aimed to explore the variation in the composition of essential oils from A. rugosa among native populations in Korea. The seeds of A. rugosa were collected from 90 different sites in Korea and seedlings were raised in the nursery. Essential oils were extracted from these populations by the steam distillation extraction method and their chemical compositions were analyzed by GC-MS. The yield of essential oils of A. rugosa ranged between 0.11% and 0.86%. A total of 204 components were identified from 90 populations of A. rugosa. Out of 204 components, 32 components were common in more than 40 individuals of A. rugosa and these 32 components were selected for principal component analysis (PCA). On the basis of the essential oil compositions, six chemotypes—estragole, pulegone, methyl eugenol, menthone, isopulegone, and nepetalactone—were distinguished according to their major components. As a result of the cluster analysis, 90 individuals of A. rugosa could be classified into three groups: estragole, methyl eugenol, and pulegone. A. rugosa exhibited significant chemical diversity among the individuals. The distribution of chemotypes is associated with the collection of seeds, suggesting that genetic diversity may influence the variations in the chemical compositions and concentrations within the species. This chemical diversity serves as the background to select cultivars for the cultivation and industrial applications of A. rugosa cultivars with high essential oil yield and concentration of its chemical components. Full article

Unlike other studies that only determined the chemical composition of essential oils depending on their geographic origin, this research investigated the effect of weather conditions (temperature, precipitation, and insolation) on the chemical composition of Nepeta nuda L. essential oil. The collection of wild-growing N. nuda was carried out during three successive years, 2019, 2020, and 2021 at Rtanj Mountain (Serbia) on the same date (July 7th). Essential oil extraction from the plant was performed by hydro-distillation. After gas chromatographic-mass spectrometric analysis, a total of 102 volatile compounds were separated from N. nuda, during the observed period, 28 were unidentified, compromising between 5.0% and 8.7%, depending on the year. A multiple linear regression model was created, and statistical analyses were performed to provide knowledge about the prediction, feature profile, and the similarity in contents of active compounds of the N. nuda essential oil. The influence of temperature on the accumulation of the most abundant component, 1,8-cineole, was positive, while the impact of precipitation and insolation was negative. According to the cluster tree, there are four chemotypes of N. nuda essential oil: with nepetalactone, 1,8-cineole, mixed (nepetalactone+1,8-cineole+germacrene D), and nonspecific chemotypes. Bearing in mind that the biological activity of a raw material depends on the chemotype and environmental factors, this is a topic that deserves a more detailed approach. The N. nuda and its essential oil are promising materials with high biological potential, and these deserve further detailed investigation. Full article

Cyclodextrin inclusion complexes have been successfully used to encapsulate essential oils, improving their physicochemical properties and pharmacological effects. Besides being well-known for its effects on cats and other felines, catnip (Nepeta cataria) essential oil demonstrates repellency against blood-feeding pests such as mosquitoes. This study evaluates the tick repellency of catnip oil alone and encapsulated in β-cyclodextrin, prepared using the co-precipitation method at a 1:1 molar ratio. The physicochemical properties of this inclusion complex were characterized using GC-FID for encapsulation efficiency and yield and SPME/GC-MS for volatile emission. Qualitative assessment of complex formation was done by UV-Vis, FT-IR, ¹H NMR, and SEM analyses. Catnip oil at 5% (v/v) demonstrated significant tick repellency over time, being comparable to DEET as used in commercial products. The prepared [catnip: β-CD] inclusion complex exerted significant tick repellency at lower concentration of the essential oil (equivalent of 1% v/v). The inclusion complex showed that the release of the active ingredient was consistent after 6 h, which could improve the effective repellent duration. These results demonstrated the effective tick repellent activity of catnip essential oil and the successful synthesis of the inclusion complex, suggesting that β-CDs are promising carriers to improve catnip oil properties and to expand its use in repellent formulations for tick management. Full article

Two Balkan Peninsula endemics, Nepeta rtanjensis and N. argolica subsp. argolica, both characterized by specialized metabolite profiles predominated by iridoids and phenolics, are differentiated according to the stereochemistry of major iridoid aglycone nepetalactone (NL). For the first time, the present study provides a comparative analysis of antimicrobial and immunomodulating activities of the two Nepeta species and their major iridoids isolated from natural sources—cis,trans-NL, trans,cis-NL, and 1,5,9-epideoxyloganic acid (1,5,9-eDLA), as well as of phenolic acid rosmarinic acid (RA). Methanol extracts and pure iridoids displayed excellent antimicrobial activity against eight strains of bacteria and seven strains of fungi. They were especially potent against food-borne pathogens such as L. monocytogenes, E. coli, S. aureus, Penicillium sp., and Aspergillus sp. Targeted iridoids were efficient agents in preventing biofilm formation of resistant P. aeruginosa strain, and they displayed additive antimicrobial interaction. Iridoids are, to a great extent, responsible for the prominent antimicrobial activities of the two Nepeta species, although are probably minor contributors to the moderate immunomodulatory effects. The analyzed iridoids and RA, individually or in mixtures, have the potential to be used in the pharmaceutical industry as potent antimicrobials, and in the food industry to increase the shelf life and safety of food products. Full article

This study was designed to evaluate, for the first time, the antioxidant and antimicrobial activities of Nepeta × faassenii essential oil (NEO). Twenty-six compounds were identified by gas chromatography and mass spectrometry analysis, of which 4a alpha,7alpha,7a alpha-nepetalactone (34.12%), elemol (23.23%), spiro(5,6)dodecane (13.73%), and 3,4 alpha-dihydro-4a alpha, 7 alpha, 7a alpha-nepetalactone (7.93%) were the major compounds. The NEO exhibited broad-spectrum antibacterial effects, and possesses potent antifungal activity on Candida albicans and Candida parapsilosis. NEO’s antioxidant activity was evaluated against cold-pressed sunflowers oil by peroxide, thiobarbituric acid, 1,1-diphenyl- 2-picrylhydrazyl radical, and β-carotene/linoleic acid bleaching methods. The NEO showed strong scavenging (IC50: 0.032 ± 0.005 mg/mL) and relative antioxidative activity (RAA%: 92.31 ± 0.17%) in 1,1-diphenyl- 2-picrylhydrazyl radical and β-carotene/linoleic acid bleaching assays, respectively. Moreover, during 24 days of the incubation period, the oil inhibits the primary lipid oxidation significantly better (p < 0.05) than butylated hydroxyanisole (BHA). In the case of secondary lipid oxidation, the oil performed significantly better (p < 0.001) than BHA from day 8 to day 12 of the incubation period. The biological activities recorded suggest that NEO may represent an antioxidant and antimicrobial agent with applications in medicine or the food industry. Full article