Search Results (12)

Background/Objectives: The genus Ferula has been traditionally used for the treatment of various illnesses, but the potential of Ferula persica var. latisecta against different Alzheimer’s disease (AD) hallmarks has never been achieved. Methods: In this work, a pressurized liquid extraction (PLE) method was optimized to extract F. persica L. aerial parts and roots. Four different solvents (water, ethanol, ethyl acetate (EtAc), and cyclopentyl methyl ether (CPME)) were first tested, and the extraction yield, total phenolic content, reactive oxygen species scavenging capacity, and acetylcholinesterase (AChE) inhibition activity were evaluated. Results: The results indicated that EtAc and CPME were the best solvents to be used, with the results obtained from the aerial parts being better than those obtained from the root samples. Thereafter, the PLE method was further optimized by combining these solvents in different percentages (100% EtAc, 100% CPME, and 50:50% (v/v) EtAc:CPME) and temperatures (50, 115, and 180 °C). Response surface methodology was then applied to analyze the data, and two optimum extraction conditions were obtained: EtAc:CPME (79:21%) at 180 °C for the aerial parts and 100% CPME at 180 °C for the roots. At these conditions, the total flavonoid content (TFC) and the inhibitory capacities against butyrylcholinesterase (BChE) and lipoxygenase (LOX) enzymes were also evaluated, indicating that the aerial part extracts had higher TFC and LOX inhibitory capacity than the root extracts but lower activity against BChE. The comprehensive LC/GC-MS chemical characterization allowed for the tentative identification of 222 compounds belonging to 66 chemical subclasses, the abundancies of which widely varied depending on the matrix and the extraction conditions used. Conclusions: The results obtained together with the application of advanced statistical analysis and molecular docking simulations suggested several sesquiterpenoids, such as selina-3,7(11)-diene, guaiol acetate, α-cyperone, and farnesyl acetate, as the molecules responsible of the in vitro results observed, with good neuroprotective potential against AD. Full article

Ilama leaves are an important source of secondary metabolites with promising anticancer properties. Cancer is a disease that affects a great number of people worldwide. This work aimed to investigate the in vivo, in vitro and in silico anticancer properties of three acyclic terpenoids (geranylgeraniol, phytol and farnesyl acetate) isolated from petroleum ether extract of ilama leaves. Their cytotoxic activity against U-937 cells was assessed using flow cytometry to determine the type of cell death and production of reactive oxygen species (ROS). Also, a morphological analysis of the lymph nodes and a molecular docking study using three proteins related with cancer as targets, namely, Bcl-2, Mcl-1 and VEGFR-2, were performed. The flow cytometry and histomorphological analysis revealed that geranylgeraniol, phytol and farnesyl acetate induced the death of U-937 cells by late apoptosis and necrosis. Geranylgeraniol and phytol induced a significant increase in ROS production. The molecular docking studies showed that geranylgeraniol had more affinity for Bcl-2 and VEGFR-2. In the case of farnesyl acetate, it showed the best affinity for Mcl-1. This study provides information that supports the anticancer potential of geranylgeraniol, phytol and farnesyl acetate as compounds for the treatment of cancer, particularly with the potential to treat non-Hodgkin’s lymphoma. Full article

Weeds are considered the main reason for crop yield loss in the world. Weed control and management include various treatments such as cultural, physical, chemical, and biological methods. Chemical control of weeds is the most common method; however, the application of commercial synthetic herbicides caused several dangerous hazards in the environment including the appearance of resistant weed biotypes. Prosopis farcta (Banks & Sol.) J.F.Macbr. (Family: Fabaceae), is a common weed plant in the Middle East, where it is hard to eliminate due to its deep and overlapped roots. On the other side, it has many traditional uses around the world. Herein, the essential oil (EO) of P. farcta above-ground parts was extracted via hydrodistillation techniques and then analyzed using gas chromatography-mass spectroscopy (GC-MS). From the GC-MS analysis, 47 compounds were identified with a relative concentration of 98.02%, including terpenes as the main components (95.08%). From overall identified compounds, cubenol (19.07%), trans-chrysanthenyl acetate (17.69%), torreyol (8.28%), davana ether (3.50%), camphor (3.35%), and farnesyl acetone (3.13%) represented the abundant constituents. Furthermore, the phytotoxic activity of the P. farcta EO was assessed against the weed Dactyloctenium aegyptium (L.) Willd. The EO of P. farcta, at a concentration of 100 µL L⁻¹, significantly inhibited the germination, seedling shoot growth, and seedling root growth by 64.1, 64.0, and 73.4%, respectively. The results exhibited that the seedling root growth is the most affected followed by the seed germination and seedling shoot growth with respective IC₅₀ at 64.5, 80.5, and 92.9 µL L⁻¹. It can be concluded that weeds are not absolutely harmful, but they may have beneficial uses, such as, for example as a source of phytochemicals with application in weed control practices (bioherbicides). It is advised to conduct additional research to characterize the allelopathic action of the major chemicals in their pure form, either alone or in combination, against a variety of weeds. Full article

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as antilymphoma agents. We identified the terpenoids farnesyl acetate (FA), phytol (PT) and geranylgeraniol (Gg) using gas chromatography–mass spectroscopy (GC-MS) and spectroscopic (¹H, and ¹³C NMR) methods applied to petroleum ether extract of leaves from A. macroprophyllata (PEAm). We investigated antitumor potential in Balb/c mice inoculated with U-937 cells by assessing brine shrimp lethality (BSL), and cytotoxic activity in these cells. In addition, to assess the potential toxicity of PEAm, FA, PT and Gg in humans, we tested their acute oral toxicity in mice. Our results showed that the three terpenoids exhibited considerable antilymphoma and cytotoxic activity. In terms of lethality, we determined a median lethal dose (LD₅₀) for thirteen isolated products of PEAm. Gg, PT and AF all exhibited a higher lethality with values of 1.41 ± 0.42, 3.03 ± 0.33 and 5.82 ± 0.58 µg mL⁻¹, respectively. To assess cytotoxic activity against U-937 cells, we calculated the mean cytotoxic concentration (CC₅₀) and found that FA and PT were closer in respect to the control drug methotrexate (MTX, 0.243 ± 0.007 µM). In terms of antilymphoma activity, we found that FA, PT and Gg considerably inhibited lymph node growth, with median effective doses (ED₅₀) of 5.89 ± 0.39, 6.71 ± 0.31 and 7.22 ± 0.51 mg kg⁻¹ in females and 5.09 ± 0.66, 5.83 ± 0.50 and 6.98 ± 0.57mg kg ⁻¹ in males, respectively. Regarding acute oral toxicity, we classified all three terpenoids as category IV, indicating a high safety margin for human administration. Finally, in a molecular docking study of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, we found binding of terpenoids to some amino acids of the catalytic site, suggesting an effect upon activity with a resulting decrease in the synthesis of intermediates involved in the prenylation of proteins involved in cancer progression. Our findings suggest that the acyclic terpenoids FA, PT, and Gg may serve as scaffolds for the development of new treatments for non-Hodgkin’s lymphoma. 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

The diamondback moth, Plutella xylostella (L.) (Lepidoptera: Plutellidae), is the most important pest of cruciferous vegetables worldwide. In this study, we evaluated the properties of selected farnesyl derivative compounds against P. xylostella. The toxicity and sublethal concentration (LC₅₀) of farnesyl acetate, farnesyl acetone, farnesyl bromide, farnesyl chloride, and hexahydrofarnesyl acetone were investigated for 96 h. The leaf-dip bioassays showed that farnesyl acetate had a high level of toxicity against P. xylostella compared to other tested farnesyl derivatives. The LC₅₀ value was 56.41 mg/L on the second-instar larvae of P. xylostella. Then, the sublethal effects of farnesyl acetate on biological parameters of P. xylostella were assessed. Compared to the control group, the sublethal concentration of farnesyl acetate decreased pupation and emergence rates, pupal weight, fecundity, egg hatching rate, female ratio, and oviposition period. Furthermore, the developmental time of P. xylostella was extended after being exposed to farnesyl acetate. Moreover, the application of farnesyl acetate on P. xylostella induced morphogenetic abnormalities in larval–pupal intermediates, adults that emerged with twisted wings, or complete adults that could not emerge from the cocoon. These results suggested that farnesyl acetate was highly effective against P. xylostella. The sublethal concentration of farnesyl acetate could reduce the population of P. xylostella by increasing abnormal pupal and adults, and by delaying its development period. Full article

The variation in habitat has a direct effect on the plants and as a consequence, changes their content of the bioactive constituents and biological activities. The present study aimed to explore the variation in the essential oils (EOs) and phenolics of Heliotropium curassavicum collected from the coastal and inland habitats. Additionally, we determined their antioxidant and allelopathic activity against the weed, Chenopodium murale. Fifty-six compounds were identified as overall from EOs, from which 25 components were identified from the coastal sample, and 52 from the inland one. Sesquiterpenes were the main class in both samples (81.67% and 79.28%), while mono (3.99% and 7.21%) and diterpenes (2.9% and 1.77%) represented minors, respectively. Hexahydrofarnesyl acetone, (-)-caryophyllene oxide, farnesyl acetone, humulene oxide, farnesyl acetone C, and nerolidol epoxy acetate were identified as major compounds. The HPLC analysis of MeOH extracts of the two samples showed that chlorogenic acid, rutin, and propyl gallate are major compounds in the coastal sample, while vanilin, quercetin, and 4′,7-dihydroxyisoflavone are majors in the inland one. The EOs showed considerable phytotoxicity against C. murale with IC₅₀ value of 2.66, 0.59, and 0.70 mg mL⁻¹ for germination, root, and shoot growth, respectively from the inland sample. While the coastal sample attained the IC₅₀ values of 1.58, 0.45, and 0.66 mg mL⁻¹. MeOH extracts revealed stronger antioxidant activity compared to the EOs. Based on IC₅₀ values, the ascorbic acid revealed 3-fold of the antioxidant compared to the EO of the coastal sample and 4-fold regarding the inland sample. However, the ascorbic acid showed 3-fold of the antioxidant activity of the MeOH extracts of coastal and inland samples. Although H. curassavicum is considered as a noxious, invasive plant, the present study revealed that EO and MeOH extracts of the H. curassavicum could be considered as promising, eco-friendly, natural resources for antioxidants as well as weed control, particularly against the weed, C. murale. Full article

Twelve terpenoids were evaluated in the treatment of type 2 diabetes mellitus: seven monoterpenes (geranyl acetate (1), geranic acid (2), citral (3), geraniol (4), methyl geranate (5), nerol (6), and citronellic acid (7)), three sesquiterpenes (farnesal (8), farnesol (9), and farnesyl acetate (10)), one diterpene (geranylgeraniol (11)), and one triterpene (squalene (12)) were selected to carry out a study on normoglycemic and streptozotocin-induced diabetic mice. Among these, 2, 3, 7, 8, 9, and 10 showed antihyperglycemic activity in streptozotocin-induced diabetic mice. They were then selected for evaluation in oral sucrose and lactose tolerance tests (OSTT and OLTT) as well as in an oral glucose tolerance test (OGTT). In the OSTT and OLTT, compounds 3, 7, 8, 9, and 10 showed a reduction in postprandial glucose peaks 2 h after a sucrose or lactose load (comparable to acarbose). In the case of the OGTT, 2, 7, 8, 9, and 10 showed a reduction in postprandial glucose peaks 2 h after a glucose load (comparable to canagliflozin). Our results suggest that the control of postprandial hyperglycemia may be mediated by the inhibition of disaccharide digestion, such as sucrose and lactose, and the regulation of the absorption of glucose. The first case could be associated with an $\propto$ -glucosidase inhibitory effect and the second with an inhibition of the sodium–glucose type 1 (SGLT-1) cotransporter. Finally, five acyclic terpenes may be candidates for the development and search for new α-glucosidase and SGLT-1 cotransporter inhibitors. Full article

Natural biopesticide development for invasive populations of red palm weevils is mainly responsible for the destruction of date palms and demands an extensive screening program of plant secondary metabolites. In the current study, the pesticidal potential of sesquiterpenes (C₁₅ H₂₄), an important class of plant secondary metabolites primarily composed of three isoprene units, was evaluated by laboratory toxicity, feeding performance bioassays, and host detoxification gene expression patterns. Dose-mortality response bioassays performed against mid-aged eighth-instar red palm weevil larvae revealed dose-dependent mortality. Only three sesquiterpenes, including Farnesol (LD₅₀ = 6559 ppm) and Farnesyl acetate (LD₅₀ = 7867 ppm), are considered to have significant toxicity, with Picrotoxin (LD₅₀ = 317 ppm) being the most toxic. Furthermore, highly toxic sesquiterpene (Picrotoxin) established in the current study tremendously reduced the feeding performance indices, including the efficacy of conversion of digested food (ECD) (81.74%) and the efficacy of conversion of ingested food (ECI) (73.62%). The least toxic sesquiterpenes, including β-Caryophyllene, (+)-Cedrol, Nerolidol, (+)-Nootkatone, and Parthenolide, observed in the current study failed to impart significant reductions of ECI and ECD indices. Lethality of the least toxic sesquiterpenes was overcome by greatly inducing gene expressions of Glutathione S transferase (GST) and Cytochrome P450. These encouraging results enabled us to suggest Picrotoxin as a promising biopesticide for the control of red palm weevil infestations. Full article

Fresh jasmine flowers have been used to make jasmine teas in China, but there has been no complete information about volatile organic compound emissions in relation to flower developmental stages and no science-based knowledge about which floral stage should be used for the infusion. This study monitored volatile organic compounds emitted from living flowers of Jasminum sambac (L.) Ait. ‘Bifoliatum’ at five developmental stages and also from excised flowers. Among the compounds identified, α-farnesene, linalool, and benzyl acetate were most abundant. Since α-farnesene is synthesized through the Mevalonate pathway, four genes encoding 3-hydroxy-3-methylglutaryl coenzyme A synthase, 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR), farnesyl pyrophosphate synthase, and terpene synthase were isolated. Their expression patterns in living flowers at the five stages and in excised flowers coincided with the emission patterns of α-farnesene. Application of lovastatin, a HMGR inhibitor, significantly reduced the expression of the genes and greatly decreased the emission of α-farnesene. The sweet scent was diminished from lovastatin-treated flowers as well. These results indicate that α-farnesene is an important compound emitted from jasmine flowers, and its emission patterns suggest that flowers at the opening stage or flower buds 8 h after excision should be used for the infusion of tea leaves. Full article

By implementing a common and industrially used method, 30 compounds which are structurally related to geranyl acetone, nerolidol, farnesal, farnesol and farnesyl acetate were obtained. Their antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, Escherichia coli, Klebsiella pneumoniae and Acinetobacter baumannii bacteria was investigated. Pharmacophore models were proposed based on the obtained results and 3D QSAR modelling. Cytotoxic effects against mainly human immortalised and normal cell lines of different origin (malignant melanoma MeWo, colorectal adenocarcinoma HT29, promyelocytic leukemia HL60, gingival fibroblasts HFIG, skin keratinocytes HaCaT and rat small intestine epithelium IEC6) were examined. The odour descriptions of newly synthesised compounds are given. Full article

We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/ H₂O₂/pyridine. The reactions, performed in CH₂Cl₂/H₂O at 25 °C, have shown good regio- and stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), ¹H-, ¹³C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects. Full article