Search Results (28)

The growing need for developing safer and more effective methods for obtaining enantiomers of chiral compounds, particularly those with pharmacological activity, highlights the potential of biocatalysis as an appropriate pharmaceutical research direction. However, low catalytic activity and stability of free enzymes are often among the substantial limitations to the wide application of biocatalysis. Therefore, to overcome these obstacles, new technological procedures are being designed. In this study, we present optimized protocols for the immobilization of Candida antarctica lipase B (CALB) on an octyl- agarose support, ensuring high enantioselectivity in an organic reaction medium. The immobilization procedures (with drying step), including buffers with different pH values and concentrations, as well as the study of the influence of temperature and immobilization time, were presented. It was found that the optimal conditions were provided by citrate buffer with a pH of 4 and a concentration of 300 mM. The immobilized CALB on the octyl-agarose support exhibited high catalytic activity in the kinetic resolution of (R,S)-1-phenylethanol via enantioselective transesterification with isopropenyl acetate in 1,2-dichloropropane (DCP), as a model reaction for lipase activity monitoring on an analytical scale. HPLC analysis demonstrated that the (R)-1-phenylethyl acetate was obtained in an enantiomeric excess of ee_p > 99% at a conversion of approximately 40%, and the enantiomeric ratio was E > 200. Thermal and storage stability studies performed on the immobilized CALB octyl-agarose support confirmed its excellent stability. After 7 days of thermal stability testing at 65 °C in a climatic chamber, the (R)-1-phenylethyl acetate was characterized by enantiomeric excess of ee_p > 99% at a conversion of around 40% (similar values of catalytic parameters to those achieved using a non-stored lipase). The documented high catalytic activity and stability of the developed CALB-octyl-agarose support allow us to consider it as a useful tool for enantioselective transesterification in organic medium. Full article

Pastinaca L. is a small genus belonging to the Apiaceae family, traditionally used for both nutritional and medicinal purposes. Pastinaca sativa L. subsp. sativa is a biennial plant widely distributed in Europe and Asia, with recognized ethnopharmacological relevance. In this study, the essential oil (EO) obtained from the aerial parts of P. sativa subsp. sativa, collected in Alto Adige (Italy)—a previously unstudied accession—was analyzed by GC-MS, and the volatile profile has been compared with that of EOs previously studied in Bulgaria and Serbia. The EO was found to be rich in octyl acetate (38.7%) and octyl butanoate (26.7%), confirming that this species biosynthesizes these natural esters. The EO and its main constituents were tested to evaluate their antimicrobial properties. Furthermore, their biological potential was evaluated through antimicrobial, antibiofilm and antioxidant assays. This research work, in addition to evaluating possible chemotaxonomic differences at the geographical level of EOs of Pastinaca sativa subsp. sativa, has been extended to the determination of the biological properties of this accession never investigated before, with the aim of acquiring a broader vision of biofilm and antibacterial properties. Full article

Background/Objectives: This study investigates the phytochemical profile, essential oil composition, and bioactivities—including antioxidant, antimicrobial, antibio-film, and anti-quorum sensing (QS) activities—of four Heracleum L. species (H. crenatifolium Boiss, H. paphlagonicum Czeczott, H. sphondylium subsp. montanum Schleich. ex Gaudin, and H. pastinacifolium subsp. incanum (Boiss. & A.Huet) P.H.Davis). Methods: Total phenolic and flavonoid contents were quantified using the Folin–Ciocalteu and aluminum chloride colorimetric methods, respectively. Essential oils were extracted by hydrodistillation and analyzed via Gas Chromatography–Flame Ionization Detector (GC–FID) and Gas Chromatography–Mass Spectrometry (GC–MS), while Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA) evaluated chemical variability among the species. Antioxidant activities were assessed using DPPH and ABTS free radical scavenging assays. Antimicrobial activity was assessed using the broth microdilution method to determine Minimum Inhibitory Concentration (MIC) values, while antibiofilm activity was evaluated using an in vitro microplate-based biofilm model against Pseudomonas aeruginosa PAO1. Anti-QS activity was analyzed using a disc diffusion assay with Chromobacterium violaceum ATCC 12472 as the reporter strain. Results: It was observed that the amounts of total phenolic compounds and total flavonoids were higher in root extracts than in aerial parts extracts for the four species in this study (H. sphondylium subsp. montanum excluding phenolic content). In the analysis of essential oil, it was determined that the major component in the roots was mostly myristicin, and in the fruits it was mostly octyl acetate. Phenolic and flavonoid contents were positively correlated with antioxidant activity. Methanol and n-hexane extracts of H. pastinacifolium (aerial parts) and n-hexane extracts of H. paphlagonicum (root) exhibited notable antimicrobial activity, primarily against Gram-positive bacteria, but none of the extracts showed activity against Klebsiella pneumoniae ATCC 13383 or P. aeruginosa ATCC 27853. Among methanol extracts, H. pastinacifolium (aerial parts) exhibited the highest antibiofilm activity (73.2%), while H. paphlagonicum (aerial parts) showed the highest activity among n-hexane extracts (75.5%). All n-hexane extracts exhibited anti-QS activity, whereas the methanol extracts showed no activity. Conclusions: These findings underscore the chemical diversity and bioactive potential of Heracleum species, contributing to the chemotaxonomic understanding of the genus and supporting their potential applications in medicine and industry. To our knowledge, this is the first study that reveals the antibiofilm and anti-QS properties of these Heracleum species. Full article

Insect sex pheromones have been widely used in integrated pest control due to their efficiency, non-toxicity, specificity, and environmental sustainability. They are considered a key component of green pest management techniques. Polymerus pekinensis is a phytophagous plant bug on alfalfa (Medicago sativa L.) in East Asia. This study used gas chromatography–electroantennogram detection (GC–EAD) and gas chromatography–mass spectrometry (GC–MS) to analyze the whole-body extracts from male and female P. pekinensis. Octyl acetate (OA) and decyl acetate (DA) elicited the antennal response of males and were identified as the predominant components of female and male extracts, respectively. Subsequent field trials demonstrated that OA (>8 mg per lure) showed the strongest attraction to conspecific males. However, when DA was added in a lure (≥2 mg), a significant decline in captures occurred. These findings provide new insights into the understanding of sex pheromones in Miridae and benefit the development of sustainable management of P. pekinensis. Full article

The resin of Commiphora africana and the resin and bark of Boswellia papyrifera play versatile roles in traditional Sudanese culture, including use in inhalation therapy, liquid remedies, and as chewing gum. Thus, this study aimed to analyze the volatile compounds in these materials using various extraction methods and assess their biological activities. Extraction methods included MonoTrap solid-phase microextraction, smoke solvent trapping, and acetone immersion. Gas chromatography−mass spectrometry analysis of MonoTrap extracts identified highly volatile compounds, while smoke extracts contained compounds with lower volatility. Solvent immersion captured a broader range of compounds. The resin of C. africana was rich in limonene, verbenone, and β-selinene, whereas B. papyrifera extracts contained octyl acetate, trans-nerolidol, and nerolidol isobutyrate as major compounds. Biological assays showed C. africana smoke extract inhibited tyrosinase activity, with p-cymene and S-limonene acting as competitive inhibitors. It also inhibited the growth of cancer cells, A549 and MIA Paca-2, while solvent extracts from both resins inhibited all tested cell lines. Further, the acetone extracts exhibited strong antibacterial activity against Streptococcus mutans. These results highlight the differences in chemical composition between the two species, the impact of extraction methods, and the therapeutic potential of C. africana and B. papyrifera as sources of bioactive compounds. Full article

Lomatium is a genus of 98 species, widely distributed in western North America. This work presents a chemometric analysis of the essential oils of seven species of Lomatium (L. anomalum, L. dissectum var. dissectum, L. multifidum, L. nudicaule, L. packardiae, L. papilioniferum, and L. triternatum var. triternatum) from the intermountain western United States (Oregon and Idaho). The essential oils were obtained by hydrodistillation and analyzed by gas chromatographic methods. Lomatium packardiae essential oil can be characterized as limonene-rich, L. anomalum is a species rich in sabinene and α-pinene, and L. multifidum essential oils were rich in myrcene, while L. dissectum var. dissectum essential oils were dominated by octyl acetate and decyl acetate, L. papilioniferum essential oils from western Idaho had high p-cymene and 2-methyl-5-(1,2,2-trimethylcyclopentyl)phenol concentrations, while those from Oregon had relatively high β-phellandrene and sedanenolide levels. The essential oils of L. triternatum var. triternatum were too variable to confidently assign a chemical type. The major components in the L. nudicaule essential oils were β-phellandrene (16.0–45.7%), (Z)-ligustilide (5.6–47.1%), (E)-β-ocimene (3.3–9.9%), and δ-3-carene (0.2–12.6%). The enantiomeric distributions of α-pinene, camphene, sabinene, β-pinene, limonene, and linalool were also utilized to discriminate between the Lomatium taxa. There are not enough consistent data to properly characterize L. triternatum var. triternatum or the Oregon L. papilioniferum essential oils. Additional research is needed to confidently describe the chemotype(s) of these species. Full article

Natural products are thoroughly studied as valuable alternatives to synthetic insecticides. Heracleum persicum Desf. ex Fisch. (Apiaceae), commonly known as Golpar, is an Iranian medicinal plant largely employed as a spice, which has previously revealed insecticidal potential. The chemical composition of H. persicum essential oil (EO) was investigated by GC-MS and was mainly dominated by hexyl butyrate (36.1%) and octyl acetate (23.7%). The EO and its main esters were tested on three mosquito species. Aedes aegypti (L.) larvae were the most sensitive to all tested products. Lethal concentrations (LC₅₀) of 59.09, 53.59, and 47.05 ppm were recorded for the EO, hexyl butyrate, and octyl acetate, respectively. Aedes albopictus (Skuse) and Anopheles gambiae Giles demonstrated comparable sensitivity to the EO, with LC₅₀ values of 102.97 and 97.91 ppm, respectively, whereas the isolated constituents appeared more active on An. gambiae (LC₅₀ of hexyl butyrate and octyl acetate of 70.97 and 60.71 ppm, respectively) with respect to Ae. albopictus (LC₅₀ of hexyl butyrate and octyl acetate of 85.40 and 91.38 ppm, respectively). Low toxicity was registered for both EO and single components against human embryonic kidney (HEK293) cells. Overall, the H. persicum EO, hexyl butyrate, and octyl acetate could be further considered for larvicide development. Full article

A series of new isatin-3-hydrazones bearing different ammonium fragments was synthesized by a simple and easy work-up reaction of Girard’s reagents analogs with 1-(3,5-di-tert-butyl-4-hydroxybenzyl)isatin. All derivatives have been shown to have antioxidant properties. In terms of bactericidal activity against gram-positive bacteria, including methicillin-resistant strains of Staphylococcus aureus, the best compounds are 3a, 3e, and 3m, bearing octyl, acetal, and brucine ammonium centers, respectively. In addition, brucine and quinine derivatives 3l, and 3j exhibit platelet antiaggregation activity at the level of acetylsalicylic acid, and this series of isatin derivatives does not adversely affect the hemostasis system as a whole. Thus, all the obtained results can lay the groundwork for future pharmaceutical developments for the creation of effective antibacterial drugs with reduced systemic toxicity due to the presence of antioxidant properties. Full article

Heracleum persicum Desf. ex Fischer seeds are a rich source of essential oils (EOs) with high antimicrobial and antioxidant effects. In order to determine the phytochemical variability in various Iranian H. persicum populations, seed samples were collected from 10 different climatic locations. The current study indicated that hexyl butyrate (20.9–44.7%), octyl acetate (11.2–20.3%), hexyl-2-methylbutyrate (4.81–8.64%), and octyl 2-methyl butyrate (3.41–8.91%) were the major components of the EOs. The maximum (44.7%) and the minimum (20.9%) content of hexyl butyrate were obtained from Kaleibar and Sari populations, respectively. Moreover, the octyl acetate content ranged from 2% (in Mahdasht) to 20.3% in Torghabeh population. The CA and PCA analysis divided the 10 Iranian H. persicum populations into three major groups. Populations from Khanghah, Kaleibar, Shebeilo, Showt, Mahdasht, and Amin Abbad showed a distinct separation in comparison with the other populations, having high contents of hexyl butyrate (39.8%) and low contents of octyl acetate (13.5%) (Chemotype II). According to correlation analysis, the highest correlation coefficient was among habitat elevation and hexyl butyrate content. In addition, the mean annual precipitation was negatively correlated with the content of hexyl butyrate. Although octyl acetate content showed high correlation with soil EC and mean annual temperature, it was not statistically significant. In general, in order to have plants with a high content of hexyl butyrate, it is recommended to harvest these plants from regions with high altitude and low rainfall such as Kaleibar. Full article

Mandelic acid is a valuable chemical that is commonly used in the synthesis of various drugs, in antibacterial products, and as a skin care agent in cosmetics. As it is an important chemical, various methods are used to synthesize and extract this compound. However, the yields of the used processes is not significant. A dilute aqueous solution is obtained when using several production methods, such as a fermentation, etc. In this study, the reactive extraction of mandelic acid from aqueous solutions using tri-n-octylamine extractant at 298.15 K was investigated. Dimethyl phthalate (DMP), methyl isobutyl ketone (MIBK), 2-octanone, 1-octanol, n-pentane, octyl acetate, and toluene were used as diluents. The batch extraction results of the mandelic acid experiments were obtained for the development of a process design. Calculations of the loading factor (Z), distribution coefficient (D), and extraction efficiency (E%) were based on the experimental data. The highest separation yield was obtained as 98.13% for 0.458 mol.L⁻¹ of tri-n-octylamine concentration in DMP. The overall extraction constants were analyzed for the complex of acid-amine by the Bizek approach, including K₁₁, K₁₂, and K₂₃. Full article

Three novel magnetically-recoverable solid acid catalysts (hydrophobic catalysts Fe₃O₄@SiO₂-Me&PrSO₃H, Fe₃O₄@SiO₂-Oc&PrSO₃H and hydrophilic catalyst Fe₃O₄@SiO₂-PrSO₃H) were synthesized by introducing organic propylsulfonic acid and alkyl groups to Fe₃O₄@SiO₂ nanocomposites. We characterized these catalysts by FT-IR, EDS, XRD, VSM and SEM, and found that they had excellent core-shell structure and magnetic responsiveness. We also explored the impact of surface hydrophobicity on activity and stability of catalysts in ethyl acetate (EAC) synthesis reaction. The results indicated that: for reactivity and reusability, Fe₃O₄@SiO₂-Oc&PrSO₃H > Fe₃O₄@SiO₂-Me&PrSO₃H > Fe₃O₄@SiO₂-PrSO₃H. This was because octyl and methyl groups could build a hydrophobic layer on the surfaces of Fe₃O₄@SiO₂-Oc&PrSO₃H and Fe₃O₄@SiO₂-Me&PrSO₃H, and this could effectively prevent water molecules from poisoning active sites; the hydrophobicity of octyl was stronger than methyl. Fe₃O₄@SiO₂-Oc&PrSO₃H also showed higher catalytic activity in the external aqueous reaction system, which indicated that it had good water toleration. Moreover, we could easily separate Fe₃O₄@SiO₂-Oc&PrSO₃H from the reaction mixture with an external magnetic field, in the meanwhile, its reactivity could still remain above 80% after reusing 6 times. Full article

Alpinia galanga is widely cultivated for its essential oil (EO), which has been used in cosmetics and perfumes. Previous studies of A. galanga focussed mostly on the rhizome but seldom on the flower. Therefore, this study was designed to identify the chemical composition of A. galanga flower EO and firstly estimate its antioxidant, antibacterial, enzyme inhibitory, and anticancer activities. According to the results of the gas chromatography with flame ionization or mass selective detection (GC-FID/MS) analysis, the most abundant component of the EO was farnesene (64.3%), followed by farnesyl acetate (3.6%), aceteugenol (3.2%), eugenol (3.1%), E-nerolidol (2.9%), decyl acetate (2.4%), octyl acetate (2.0%), sesquirosefuran (1.9%), (E)-β-farnesene (1.7%), and germacrene D (1.5%). For the bioactivities, the EO exhibited moderate DPPH and ABTS radical scavenging effects with IC₅₀ values of 138.62 ± 3.07 μg/mL and 40.48 ± 0.49 μg/mL, respectively. Moreover, the EO showed strong-to-moderate antibacterial activities with various diameter of inhibition zone (DIZ) (8.79–14.32 mm), minimal inhibitory concentration (MIC) (3.13–6.25 mg/mL), and minimal bactericidal concentration (MBC) (6.25–12.50 mg/mL) values against Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, and Proteus vulgaris. Interestingly, the EO possessed remarkable α-glucosidase inhibition (IC₅₀ = 0.16 ± 0.03 mg/mL), which was equivalent to that of the positive control acarbose (IC₅₀ = 0.15 ± 0.01 mg/mL) (p > 0.05). It showed moderate tyrosinase inhibition (IC₅₀ = 0.62 ± 0.09 mg/mL) and weak inhibitory activity on acetylcholinesterase (AChE) (IC₅₀ = 2.49 ± 0.24 mg/mL) and butyrylcholinesterase (BChE) (IC₅₀ = 10.14 ± 0.59 mg/mL). Furthermore, the EO exhibited considerable selective cytotoxicity to K562 cells (IC₅₀ = 41.55 ± 2.28 μg/mL) and lower cytotoxicity to non-cancerous L929 cells (IC₅₀ = 120.54 ± 8.37 μg/mL), and it induced K562 cell apoptosis in a dose-dependent manner. Hence, A. galanga flower EO could be regarded as a bioactive natural product with great application potential in the pharmaceutical field. Full article

A comparative analysis of the chemical constituents present in twenty-one commercial and two lab-distilled frankincense (Boswellia carteri) essential oils was carried out using gas chromatography-mass spectrometry (GC-MS) and chiral gas chromatography-mass spectrometry (CGC-MS) for authentication. Out of the twenty-one commercial samples, six were adulterated with synthetic limonene, three were contaminated with synthetic octyl acetate, three were adulterated with castor oil, and two samples each were contaminated with frankincense resin and Boswellia occulta species, respectively, and one was contaminated with the Boswellia serrata species. Additionally, one sample was contaminated with phthalates as well as a cheap essential oil with similar compositions. Furthermore, one sample was adulterated with copaiba resin and frankincense resin in combination with synthetic octyl acetate. Additionally, one was contaminated with Boswellia serrata species, which was further adulterated with castor oil and frankincense resin. To the best of our knowledge, this is the first report to compare the enantiomeric distribution of chiral terpenoids present in commercial frankincense essential oil with lab-distilled frankincense oil for authentication. The CGC-MS analysis showed the presence of a total of eight chiral terpenoids in lab-distilled frankincense essential oils, which can be used as chemical fingerprints for the authentication of frankincense essential oil. Full article

Fragaria nilgerrensis Schlecht. is a wild diploid strawberry species. The intense peach-like aroma of its fruits makes F. nilgerrensis an excellent resource for strawberry breeding programs aimed at enhancing flavors. However, the formation of the peach-like aroma of strawberry fruits has not been comprehensively characterized. In this study, fruit metabolome and transcriptome datasets for F. nilgerrensis (HA; peach-like aroma) and its interspecific hybrids PA (peach-like aroma) and NA (no peach-like aroma; control) were compared. In total, 150 differentially accumulated metabolites were detected. The K-means analysis revealed that esters/lactones, including acetic acid, octyl ester, δ-octalactone, and δ-decalactone, were more abundant in HA and PA than in NA. These metabolites may be important for the formation of the peach-like aroma of F. nilgerrensis fruits. The significantly enriched gene ontology terms assigned to the differentially expressed genes (DEGs) were fatty acid metabolic process and fatty acid biosynthetic process. Twenty-seven DEGs were predicted to be associated with ester and lactone biosynthesis, including AAT, LOX, AOS, FAD, AIM1, EH, FAH, ADH, and cytochrome P450 subfamily genes. Thirty-five transcription factor genes were predicted to be associated with aroma formation, including bHLH, MYB, bZIP, NAC, AP2, GATA, and TCPfamily members. Moreover, we identified differentially expressed FAD, AOS, and cytochrome P450 family genes and NAC, MYB, and AP2 transcription factor genes that were correlated with δ-octalactone and δ-decalactone. These findings provide key insights into the formation of the peach-like aroma of F. nilgerrensis fruits, with implications for the increased use of wild strawberry resources. Full article

Essential oils are important compounds for the prevention and/or treatment of various diseases in which solubility and bio-accessibility can be improved by nanoemulsion systems. Heracleum persicum oil nanoemulsion (HAE-NE) was prepared and biological properties were investigated against human breast cancer cells and normal human fibroblasts foreskin. Particle size, zeta potential and poly dispersity index were 153 nm, −47.9 mV and 0.35, respectively. (E)anethole (57.9%), terpinolene (13.8%), ɣ-terpinene (8.1%), myrcene (6.8%), hexyl butyrate (5.2%), octyl butanoate (4.5%) and octyl acetate (3.7%) was detected in nanoemulsion. Proliferation of cancer cells at IC₅₀ = 2.32 μg/mL was significantly (p < 0.05) inhibited, and cell migration occurred at 1.5 μL/mL. The HAE-NE at 1.5, 2.5 and 3.5 µg/concentration up-regulated caspase 3 and enhanced sub-G1 peak of cell cycle with nil cytotoxic effects in the liver, kidney and jejunum of mice. Villus height, villus width, crypt depth and goblet cells in mice group fed with 10 and 20 mg/kg body weight of HAE-NE improved. Cellular redox state in the liver indicated 10 and 20 mg/kg body weight of nanoemulsion significantly up-regulated the expression of SOD, CAT and GPx genes. Heracleum persicum oil nanoemulsion could be an eco-friendly nanotherapeutic option for pharmaceutical, cosmetological and food applications. Full article