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The enantiomers (R)-(+)-β-citronellol and (S)-(−)-β-citronellol are present in many medicinal plants, but little is understood about their bioactivity against Candida yeasts. This study aimed to evaluate the behavior of positive and negative enantiomers of β-citronellol on strains of Candida albicans and C. tropicalis involved in candidemia. The minimum inhibitory concentration (MIC) and minimum fungicide concentration (MFC) were determined. The evaluation of growth kinetics, mechanism of action, and association studies with Amphotericin B (AB) using the checkerboard method was also performed. R-(+)-β-citronellol and S-(−)-β-citronellol presented a MIC50% of 64 µg/mL and a MFC50% of 256 µg/mL for C. albicans strains. For C. tropicalis, the isomers exhibited a MIC50% of 256 µg/mL and a MFC50% of 1024 µg/mL. In the mechanism of action assay, both substances displayed an effect on the fungal membrane but not on the fungal cell wall. Synergism and indifference were observed in the association of R-(+)-β-citronellol and AB, while the association between S-(−)-β-citronellol and AB displayed synergism, additivity, and indifference. In conclusion, both isomers of β-citronellol presented a similar profile of antifungal activity. Hence, they can be contemplated in the development of new antifungal drugs providing that further research is conducted about their pharmacology and toxicity.

Glioblastoma is the most prevalent type of brain tumor, and because of drug resistance, treatment for gliomas has been less successful. Citronellol is an acyclic monoterpene alcohol with various pharmacological properties. This study aimed to evaluate the effect of citronellol and its nanoformulation on glioblastoma cell proliferation. The physicochemical properties of citronellol and its synthesized silver nanoconjugates (CN@AgNPs) were evaluated using DFT and ADMET studies. The targets of the investigation (p53 and CDK4) were identified through the application of chemogenomics and analysis of the STRING protein-protein interaction network. Ligands were docked to the interaction sites of specific targets using AutoDock Vina 1.5.7. Molecular dynamics were used to mimic the citronellol complex CDK4 and p53. Because metallic bonds, which provide metals with unique strength and stability, are more resilient and long-lasting than hydrogen bonds, the results showed that the CN@AgNPs generated a more stable complex. Citronellol and CN@AgNPs were assessed by an in vitro study to determine the expression of IC 50 concentration for the top scored selected genes to confirm the cytotoxicity of the compound against the GBM cell line SF-767. The findings showed that Citronellol and CN@AgNPs had concentration-dependent cytotoxic effects. Citronellol and CN@AgNPs, with IC 50 values of 20.04 ± 4 µg/mL and 19.67 ± 4 µg/mL, respectively, decreased CDK4 expression and raised p53 expression in the SF-767 cancer cell line. In conclusion, the cytotoxicity and inhibition index of glioblastoma cells were increased by the phytocompounds coupled with AgNPs. Therefore, CN@AgNPs may be a good choice for treating cancer.

Tumor cells are characterized as redox-heterogeneous intracellular microenvironment due to the simultaneous overproduction of reactive oxygen species and glutathione. Rational design of redox-responsive drug delivery systems is a promising prospect for efficient cancer therapy. Herein, six paclitaxel-citronellol conjugates are synthesized using either thioether bond, disulfide bond, selenoether bond, diselenide bond, carbon bond or carbon-carbon bond as linkages. These prodrugs can self-assemble into uniform nanoparticles with ultrahigh drug-loading capacity. Interestingly, sulfur/selenium/carbon bonds significantly affect the efficiency of prodrug nanoassemblies. The bond angles/dihedral angles impact the self-assembly, stability and pharmacokinetics. The redox-responsivity of sulfur/selenium/carbon bonds has remarkable influence on drug release and cytotoxicity. Moreover, selenoether/diselenide bond possess unique ability to produce reactive oxygen species, which further improve the cytotoxicity of these prodrugs. Our findings give deep insight into the impact of chemical linkages on prodrug nanoassemblies and provide strategies to the rational design of redox-responsive drug delivery systems for cancer therapy. Prodrug-based self-assembled nanoparticles have emerged as an efficient drug delivery system (DDS) for cancer therapy. Here, the authors show that the type of bond in prodrug assemblies influences the efficiency of the DDS on several different levels.

The essential oil of Rosa damascena is extensively used as a key natural ingredient in the perfume and cosmetic industries. However, the productivity and quality of rose oil are a big concern from the old plantation. It is hypothesized that rejuvenation of old rose plantations through ground-level pruning at right time could improve the yield of flowers and the quality of essential oil. Consequently, a field trial was led-out with 10 treatment conditions encompassing two pruning systems (ground-level pruning and ground-level pruning followed by top pruning at the end of December) and five different months of ground-level pruning (June–October) to understand the best pruning practices. In this experiment, the flower yield ranged from 18.32 to 62.40 q ha −1 , and oil content varied from 0.035 to 0.049% under different pruning systems and months of pruning. Ground-level pruned plants, irrespective of the month, registered statistically ( p ≤ 0.05) more flower yield (618.62 and 473.29 g bush −1 ) compared with ground-level pruning followed by top pruned plants in both seasons. The average across the pruning system, ground-level pruning in October registered statistically ( p ≤ 0.05) greater yield of flowers (709.10 and 605.13 g bush −1 ) compared with the ground-level pruning from June to August. Despite significant variations in flower yield among the treatments, the percentage share of the major compounds particularly β-citronellol+nerol and geraniol in the essential oil were not affected ( p ≥ 0.05) by the pruning month and pruning system. Thus, the finding suggests that the production from the old plantation of R. damascena can be improved by ground-level pruning during October under mild-temperate conditions.

Essential oil-based bioherbicides are a promising avenue for the development of eco-friendly pesticides. This study formulated nanoemulsions containing citronella ( Cymbopogon nardus ) essential oil (CEO) as an herbicidal product using a high-pressure homogenization method with hydrophilic-lipophilic balance (HLB) values ranging 9–14.9 for the surfactant mixture (Tween 60 and Span 60). The CEO was high in monoterpene compounds (36.333% geraniol, 17.881% trans -citral, 15.276% cis -citral, 8.991% citronellal, and 4.991% β -citronellol). The nanoemulsion at HLB 14 was selected as optimal due to having the smallest particle size (79 nm, PI 0.286), confirmed by transmission electron microscopy. After 28 days of storage, particle size in the selected formulation changed to 58 and 140 nm under 4 °C and 25 °C, respectively. Germination and seedling growth assays with Echinochloa crus-galli showed that the nanoemulsion exerted a significant dose-dependent inhibitory effect at all tested HLBs (9–14.9) and concentrations (100–800 µL/L). The inhibitory effect was greatest at HLB 14. Treatment of E. cruss-galli seed with the HLB 14 nanoemulsion significantly reduced seed imbibition and α -amylase activity. Our findings support that CEO nanoemulsions have a phytotoxic effect and hence herbicidal properties for controlling E. cruss-galli . Accordingly, this nanoemulsion may have potential as a bioherbicide resource.

The prominent cultivation of lemongrass (Cymbopogon spp.) relies on the pharmacological incentives of its essential oil. Lemongrass essential oil (LEO) carries a significant amount of numerous bioactive compounds, such as citral (mixture of geranial and neral), isoneral, isogeranial, geraniol, geranyl acetate, citronellal, citronellol, germacrene-D, and elemol, in addition to other bioactive compounds. These components confer various pharmacological actions to LEO, including antifungal, antibacterial, antiviral, anticancer, and antioxidant properties. These LEO attributes are commercially exploited in the pharmaceutical, cosmetics, and food preservations industries. Furthermore, the application of LEO in the treatment of cancer opens a new vista in the field of therapeutics. Although different LEO components have shown promising anticancer activities in vitro, their effects have not yet been assessed in the human system. Hence, further studies on the anticancer mechanisms conferred by LEO components are required. The present review intends to provide a timely discussion on the relevance of LEO in combating cancer and sustaining human healthcare, as well as in food industry applications.

Terpene esters of short-chain fatty acids are essential oils that have big importance in food, cosmetic and pharmaceutical industries as flavours and fragrances. Geraniol and citronellol are the most important substances. Considering the ever-increasing demand for such products, their enzymatic production from natural raw materials by using environmentally friendly and economically attractive processes may prove advantageous. In this contribution, we would like to present an alternative option for the production of geranyl propionate using nanobioconjugates consisting of Candida rugosa lipase adsorbed onto multi-walled carbon nanotubes (CRL-MWCNTs). We investigated the effects of incubation time, temperature, solvent log P and substrate molar ratio, and determined the optimum conditions. The yield of geranyl propionate catalysed by CRL-MWCNTs nanobioconjugates was significantly influenced by two factors, namely, temperature and time of the reaction. Under the optimum reaction conditions of 55 °C, solvent n-heptane (log P = 4.0), geraniol to propionic acid molar ratio of 5:1 and reaction time of 6 h, the use of CRL-MWCNTs resulted in 51.3% production of geranyl propionate. Therefore, the investigation revealed that geranyl propionate was successfully synthesized under mild conditions with reasonably high yield within a short period of time. The CRL-MWCNTs nanobioconjugates demonstrated a potential as economical and environmentally smarter biocatalysts for the production of geranyl propionate.

A natural herbicide nanoemulsion was fabricated from citronella ( Cymbopogon nardus L.) essential oil (CEO) and a nonionic surfactant Tween 60 mixed with Span 60 at hydrophilic-lipophilic balance 14 using a microfluidization method. The main constituents of CEO were citronellol (35.244%), geraniol (21.906%), and citronellal (13.632%). CEO nanoemulsion droplet size and polydispersity index (PI) were evaluated by dynamic light scattering (DLS). The smallest droplet size (33.2 nm, PI 0.135) was obtained from a microfluidizer at 20,000 psi, 7 cycles. Nanoemulsion droplet in transmission electron microscopy correlated with DLS confirmed CEO to successfully produce nanoemulsion. The herbicidal activity of the nanoemulsion as a foliar spray was evaluated against Echinochloa cruss-galli and Amaranthus tricolor as representative narrow- and broadleaf weed plants, both of which presented visual toxicity symptoms. The modes of action of the nanoemulsion were then determined in terms of membrane integrity (relative electrolyte leakage; REL), malondialdehyde (MDA), and photosynthetic pigment contents. The results showed increase in REL and MDA which indicated the destruction of the treated plants; additionally, chlorophylls and carotenoid contents were decreased. Consequently, CEO nanoemulsion may have the possibility to act as a natural herbicide resource, and natural herbicides from citronella nanoemulsions could be good alternatives for use in sustainable agriculture.

Tyrosinase is a key enzyme in melanin synthesis, and its natural inhibitors are receiving increasing attention. Rosa × damascena Herrm. essential oil (RDEO), as important functional metabolites, was widely known due to its biological activities. But its tyrosinase inhibitory activity has not been detailed investigated. Therefore, in this paper, RDEO was comprehensively investigated the tyrosinase inhibitory, followed by the phytochemical composition analysis. Activity screening results showed that RDEO exhibited effective anti-tyrosinase activity and was a reversible and mixed-type inhibitor. CD assay results revealed that RDEO could affect the conformation of tyrosinase to reduce the activity. In B16F10 cells, RDEO (25–100 μg/mL) could inhibit intracellular tyrosinase activity and decrease melanin content. Finally, GC-MS analysis of RDEO found that citronellol (21.22%), geraniol (14.1%), eicosane (11.03%), heneicosane (6.65%) and 1-nonadecene (5.16%) were its main phytochemical compositions. This study provided data support for Rosa × damascena Herrm. essential oil as one potential natural tyrosinase inhibitor and its applications in cosmetics and medicine.

The efficacy of 30 aromatic compounds and their mutual binary combinations was assessed for acute toxicity against the larvae Culex quinquefasciatus. Based on comparison of the lethal doses, thymol and p-cymene were selected as the most effective (LD50 = 18 and 21 mg L−1, respectively, and LD90 = 25 and 30 mg L−1, respectively). Although the LD50 for terpinolene and trans-anethole was also estimated at 21 mg L−1, their LD90 was significantly higher compared to the substances above (245 and 34 mg L−1, respectively). In total, 435 binary combinations were tested, of which 249 combinations showed a significant synergistic effect, while 74 combinations showed a significant antagonistic effect on mortality. Only nine substances were identified as being able to create a synergistic effect with more than 20 substances: limonene, trans-anethole, 4-allylanisole, carvacrol, isoeugenol, menthone, carvone, borneol, and camphor. The highest synergistic effect on larval mortality was achieved for the combinations: eugenol and isoeugenol, carvone and carvacrol, carvone and 4-allylanisole, carvone and α-terpineol, carvone and menthone, limonene and trans-anethole, limonene and menthone, α-pinene and menthone, β-citronellol and menthone, carvacrol and 4-allylanisole, carvacrol and terpineol, α-terpinene and trans-anethole, camphor and menthone, camphene and menthone, and 4-allylanisole and menthone. Significant differences between achieved mortality and the mutual mixing ratio were found for the five selected binary mixtures that had shown the most significant synergistic effect in the previous tests. The mixture of limonene and trans-anethole showed the highest mortality, with the mixing ratio 1:1; the mixture of eugenol and isoeugenol caused 90.2 % mortality, with the mixing ratio 1:3. One hundred percent mortality was achieved if carvacrol was contained in a mixture with carvone in a ratio >2. After a comparison of all our results, based on our experiments, we can choose two pairs that caused mortality higher than 90 % in concentrations lower than 20 mg L−1: limonene and trans-anethole (with the mixing ratio 1:1), and carvone and carvacrol (with the mixing ratio 1:2–3). The information gained can thus be used in the development of new botanical insecticides based on essential oils (EOs) and particularly in the creation of formulations.