Terpene Compounds Research Articles

Separation of biomass furans by terpenoid-based hydrophobic deep eutectic solvents probed by molecular dynamics simulations and liquid-liquid extraction experiments

Preparing furfuryl alcohol from furfural using liquid-phase hydrogenation as a raw material contains a certain amount of furfuryl alcohol (FA) and furfural (FF) in the final process wastewater, which needs to be separated. This article uses FA and FF aqueous solutions as model wastewater and hydrophobic eutectic solvents (HDESs) as extractants. Nine HDESs are prepared with three terpene compounds and three fatty acids in different proportions. Liquid extraction experiments are carried out to determine the best HDESs for separating this wastewater. Furthermore, the optimal operating conditions were determined by changing the extraction temperature, the initial concentrations of FA and FF in the wastewater, and the amount of HDESs used. Simultaneously, the ability of hydrogen bond acceptors (HBA) and hydrogen bond donors (HBD) to form hydrogen bonds and the affinity or repulsion between components were predicted using quantum chemistry (QC) calculations. The microscopic mechanism of action between HDES and the wastewater model was analysed using molecular dynamics (MD) simulation to study the effect of extraction conditions on the separation effect. Ultimately, the experimental results showed that the LLE of low-concentration (0.2 %) wastewater model with Mth-Dec (2:1) at 40 °C had a high extraction efficiency for FA and FF, which were 84.81 % and 87.49 %, respectively. The experimental results correspond to the high selectivity for FA and FF (3.30 and 3.88, respectively) in the molecular modelling results, indicating that the method proposed in this paper can be used to study related separation problems.

Anti-Staphylococcus aureus Activity of Volatile Phytochemicals and Their Combinations with Conventional Antibiotics Against Methicillin-Susceptible S. aureus (MSSA) and Methicillin-Resistant S. aureus (MRSA) Strains.

MSSA and MRSA strains are challenging human pathogens that can develop resistance to antibiotics, highlighting the need for alternative antimicrobial agents. Plant metabolites, particularly volatile phytochemicals, may offer promising antimicrobial properties. The aim was to evaluate the antimicrobial and antibiofilm efficacy of various commercial volatile phytochemicals from the terpene and terpenoid groups against reference MSSA and MRSA strains, focusing on synergistic effects in both binary combinations and combinations with antibiotics. The microdilution method was used to determine the minimum inhibitory concentrations (MICs) for antibiotics and phytochemicals. The checkerboard method assessed synergistic interactions between phytochemicals and between phytochemicals and antibiotics, while the time-kill method was used to confirm these results. Biofilm quantification was performed using the microtiter plate method to evaluate the effects of phytochemicals, antibiotics, and their binary combinations on the eradication of 48-h-old biofilms. Carvacrol and thymol demonstrated the strongest anti-staphylococcal activity, while other terpene compounds showed weaker effects. In binary combinations, carvacrol and thymol exhibited synergy against one MSSA strain (FICI = 0.50) and with tetracycline and chloramphenicol (FICI = 0.28-0.50). Synergy was also noted with streptomycin sulfate against one MRSA strain (FICI = 0.31-0.50) and with other antibiotics, including gentamicin (FICI = 0.25-0.50) and oxacillin (FICI = 0.44). Additionally, effective combinations achieved over 50% biofilm removal at both minimum inhibitory and sub-inhibitory concentrations. Results showed that synergy varies based on strain sensitivity to chemical agents, highlighting their potential for personalized therapy. Despite the difficulty in removing preformed biofilms, the findings highlight the importance of combined treatments to enhance antibiotic effectiveness.

Exploring dermatological applications of Ammoides pusilla essential oil: evaluation of anti-aging, dermatoprotective and antimicrobial properties against dermatopathogenic microorganisms

The aim of this study was the phytochemical characterization of essential oil extracted from the aerial parts (stems, leaves, and flowers) of Ammoides pusilla (Brot.) Breistr (APEO) by use of GC–MS. Importantly, GC–MS results revealed that APEO oil composed of 10 terpene compounds, of which carvacrol (52.84%), d-limonene (17.78%), β-Cymene (13.18%) and γ-Terpinene (8.46%) predominate. These compounds are recognized for their important biological properties. APEO demonstrated remarkable antimicrobial activity, outperforming positive controls in all cases. Inhibition diameters ranged from 30.20 mm against Candida glabrata to 49.80 mm against Candida albicans, with minimum inhibitory concentrations (MICs) ranging from 0.25% against Staphylococcus aureus and Micrococcus luteus to 4.00% against Candida glabrata. This antimicrobial efficacy is attributed to the oil's rich bioactive molecules. The essential oil also showed significant dose-dependent inhibition of anti-tyrosinase activity, with IC50 of 29.59 ± 1.89 µg/mL for monophenolase activity and 17.56 ± 0.76 µg/mL for diphenolase activity. At the same time, APEO showed significant inhibition of elastase, with an IC50 of 20.90 ± 3.16 µg/mL. The sun protection factor (SPF) of the essential oil was determined to be 4.323. This SPF value corresponds to an estimated 76.88% effectiveness in blocking UVB radiation. These results suggest that APEO possesses promising dermatoprotective and anti-aging properties. In conclusion, APEO exhibits notable antimicrobial, anti-tyrosinase and anti-elastase activities, paving the way for new natural therapeutic options for skin problems, with anti-aging and dermatoprotective dermal applications.

Origanum majorana L. as Flavoring Agent: Impact on Quality Indices, Stability, and Volatile and Phenolic Profiles of Extra Virgin Olive Oil (EVOO).

The flavoring of olive oils with aromatic plants is commonly used to enrich the oils with aromatic and antioxidant compounds. Origanum majorana L. was applied as a flavoring agent for extra virgin olive oil (EVOO), at concentrations of 20 g L-1 and 40 g L-1, via ultrasound-assisted maceration. The aim of this study was to evaluate the impact of flavoring on the EVOOs' quality indices, oxidative stability, and antioxidant, antiradical and antifungal activities, as well as on the oils' volatile and phenolic profile. The flavored EVOO maintained the quality indices (free fatty acids, peroxide value, extinction coefficients) below the maximum permitted levels, whereas the addition of marjoram enhanced the oxidative stability, the levels of chlorophyll and b-carotene and the total phenolic content. The incorporation of marjoram into the EVOO did not have a significant impact on the antioxidant and antiradical activities. Concerning the antifungal activity, no Zygosaccharomyces bailli cell growth was observed for two weeks in a mayonnaise prepared with the flavored EVOO at a 40 g L-1 concentration. SPME-GC-MS analysis revealed the presence of 11 terpene compounds (hydrocarbon and oxygenated monoterpenes) that had migrated from marjoram in the flavored EVOO. Twenty-one phenolic compounds were tentatively characterized by LC-QToF-MS in the EVOO samples; however, hesperetin and p-coumaric acid, originating from marjoram, were only detected in the flavored EVOO.

Illuminating Cannabis sativa L.: The Power of Light in Enhancing C. sativa Growth and Secondary Metabolite Production.

Light is crucial for higher plants, driving photosynthesis and serving as a powerful sensory signal that profoundly modulates growth, development, physiological functions, hormone activation, and biochemical pathways. Various light parameters-quality, intensity, composition, and photoperiod-exert a tremendous influence on plant growth and development, particularly in industrial hemp (Cannabis sativa L.). C. sativa, a crop of historical significance and unparalleled versatility, holds immense value in the food, fiber, and medicinal industries. The cultivation of medicinal cannabis is burgeoning in controlled environments due to evolving healthcare regulations. Optimal light conditions significantly enhance both yield and harvest quality, notably increasing the density of apical inflorescences and the ratio of inflorescence to total aboveground biomass. C. sativa metabolites, especially phenolic and terpene compounds and Phytocannabinoids like CBD (cannabidiol), THC (tetrahydrocannabinol), and CBG (cannabigerol), possess immense medicinal value. Secondary metabolites in C. sativa predominantly accumulate in the trichomes of female flowers and surrounding sugar leaves, underscoring the critical need to boost inflorescence weight and metabolite concentrations while ensuring product consistency. Different light parameters distinctly impact C. sativa's metabolic profile, providing a robust foundation for understanding the optimal conditions for synthesizing specific secondary metabolites. While the effects of light measurement on various crops are well-established, scientific evidence specifically relating to light quality effects on C. sativa morphology and secondary metabolite accumulation remains scarce. In this review, we critically summarized how different light properties can alter cannabis growth (vegetative and reproductive), physiology and metabolism. Furthermore, the mechanisms by which specific wavelengths influence growth, development, and secondary metabolite biosynthesis in C. sativa are not fully elucidated, which could be a prospective task for future researchers. Our review paves the way for a profound understanding of light's influence on C. sativa growth and advancements in greenhouse settings to maximize metabolite production for commercial use.

Aroma enhancement of dealcoholized wines using enzyme treatment and glycosidic aroma precursors

This research has studied the treatment of dealcoholized wines with glycosidic enzymatic preparation and glycosidic aroma precursors extract isolated from aromatic grapes in order to enhance the aroma profile of non-alcoholic white wines. The effect of the addition of the precursors extract and the enzymatic treatment was studied after 15 and 30 d of storage, using dealcoholized wine as control. The analysis of free and bound volatile compounds was carried out by gas chromatography-mass spectrometry (GC-MS) after isolation using solid-phase extraction (SPE). The application of multivariate statistical analysis confirmed differences in the free and bound volatile profile of the studied samples when applicated the different treatments after 15 d and 30 d of storage. The combination of both treatments increased in a significant way the aromatic profile of Verdejo dealcoholized wine, showing high concentrations of terpenic and bencenic compounds due to the addition of precursors extract from an aromatic grape variety. This brings to light that this technique could be considered as a possible way of enhancing the aroma profile of dealcoholized wines in La Mancha region, as well as a way of using by-products from the wine industry, thus contributing to the concept of circular economy.

Development of GC–MS coupled to GC–FID method for the quantification of cannabis terpenes and terpenoids: Application to the analysis of five commercial varieties of medicinal cannabis

Cannabis terpenes and terpenoids are among the major classes of pharmacologically active secondary metabolites of therapeutic interest. Indeed, these hydrocarbon molecules, responsible for the characteristic aroma of cannabis flowers, are thought to be involved in a synergistic effect known as the “entourage effect”, together with cannabinoids. Numerous analytical studies have been carried out to characterize the terpene and terpenoid contents of some cannabis varieties, but they have not proposed any real quantification or have described a limited number of analytical standards or average response factors, which may have led to over- or underestimation of the real content of the cannabis flowers. Real and reliable quantification is necessary to justify the entourage effect. Here, we report a rigorous and precise GC–FID and GC–MS method for the identification and quantification of cannabis terpenes and terpenoids. This method is distinguished by the use of a high number of analytical standards, the determination of retention indices for all compounds studied, an exhaustive comparison of databases and scientific literature, the use of relevant response factors, and internal calibration for reliable results. It was applied to the study of terpenic compounds in five commercial varieties of medicinal cannabis produced by Bedrocan International: a CBD-rich (Bedrolite®), a THC/CBD balanced (Bediol®), and three THC-dominant (Bedrocan®, Bedica® and Bedrobinol®). Two extraction solvents are described (ethanol and hexane) to compare their selectivity towards target molecules, and to describe as exhaustively as possible the terpenic profile of the five pharmaceutical-grade varieties. Twenty-three standards were used for accurate dosages. This work highlights that the choice of solvent and the analysis method reliability are critical for the study of these terpenic compounds, regarding their contribution to the entourage effect.

Gene isolation and enzymatic characterization of UDP-glycosyltransferases of terpene glucoside biosynthesis involved in linalyl-glycoside accumulation in Coffea arabica

Terpenes, one of the secondary metabolites produced by plants, have diverse physiological functions. They are volatile compounds with physiological bioactivities (e.g., insect repellent, attracting enemies, and interacting with other plants). Terpenoids are also essential for flavor and aroma in plant-derived foods. In coffee, its aroma decides the value of coffee beans. Linalool, one of the volatile terpene compounds, is dominant in the coffee aroma. Coffee, with its good flavor and aroma, has high demand worldwide. Because terpenoids generally accumulate as glycosides in plant cells, glycosylation is catalyzed by UDP-glycosyltransferases (UGTs). Two linalyl-diglycosides have been identified: terpenoids reflected as necessary for coffee flavor. However, these UGTs and their action mechanisms are unknown in the Coffea genus. To obtain knowledge of terpene UGTs and elucidate the mechanism of terpene glycosylation in coffee, this study isolated terpene UGT genes and analyzed their functions. In silico screening based on the sequence of UGT85K11, which catalyzes terpene glycosylation from Camellia sinensis, was performed to obtain sequence information on five candidate UGT genes (CaUGT4, CaUGT5, CaUGT10, CaUGT15, and CaUGT20). These genes were isolated by reverse transcription-polymerase chain reaction, and the recombinant enzymes were produced with the Escherichia coli expression system. In functional analysis using radioisotopes, CaUGT4 showed critical activity against linalool, which had a higher affinity for its substrate than that of UGT85A84 from Osmanthus fragrans. Liquid chromatography-tandem mass spectrometry also revealed that CaUGT4 mainly produces linalyl glucoside. In this study, the first linalyl UGT was isolated from coffee. These findings can be used to elucidate the fundamental mechanism of the chemical defense in plants and apply aroma precursors for the plant-derived food industry in the future.

Microbial dynamics, chemical profile, and bioactive potential of diverse Egyptian marine environments from archaeological wood to soda lake

Halophilic archaea are a unique group of microorganisms that thrive in high–salt environments, exhibiting remarkable adaptations to survive extreme conditions. Archaeological wood and El–Hamra Lake serve as a substrate for a diverse range of microorganisms, including archaea, although the exact role of archaea in archaeological wood biodeterioration remains unclear. The morphological and chemical characterizations of archaeological wood were evaluated using FTIR, SEM, and EDX. The degradation of polysaccharides was identified in Fourier transform infrared analysis (FTIR). The degradation of wood was observed through scanning electron microscopy (SEM). The energy dispersive X–ray spectroscopy (EDX) revealed the inclusion of minerals, such as calcium, silicon, iron, and sulfur, into archaeological wood structure during burial and subsequent interaction with the surrounding environment. Archaea may also be associated with detected silica in archaeological wood since several organosilicon compounds have been found in the crude extracts of archaeal cells. Archaeal species were isolated from water and sediment samples from various sites in El–Hamra Lake and identified as Natronococcus sp. strain WNHS2, Natrialba hulunbeirensisstrain WNHS14, Natrialba chahannaoensis strain WNHS9, and Natronococcus occultus strain WNHS5. Additionally, three archaeal isolates were obtained from archaeological wood samples and identified as Natrialba chahannaoensisstrain W15, Natrialba chahannaoensisstrain W22, and Natrialba chahannaoensisstrain W24. These archaeal isolates exhibited haloalkaliphilic characteristics since they could thrive in environments with high salinity and alkalinity. Crude extracts of archaeal cells were analyzed for the organic compounds using gas chromatography–mass spectrometry (GC–MS). A total of 59 compounds were identified, including free saturated and unsaturated fatty acids, saturated fatty acid esters, ethyl and methyl esters of unsaturated fatty acids, glycerides, phthalic acid esters, organosiloxane, terpene, alkane, alcohol, ketone, aldehyde, ester, ether, and aromatic compounds. Several organic compounds exhibited promising biological activities. FTIR spectroscopy revealed the presence of various functional groups, such as hydroxyl, carboxylate, siloxane, trimethylsilyl, and long acyl chains in the archaeal extracts. Furthermore, the archaeal extracts exhibited antioxidant effects. This study demonstrates the potential of archaeal extracts as a valuable source of bioactive compounds with pharmaceutical and biomedical applications.

Phytochemical Characterization of the Aerial Parts of Teucrium nuchense K. Koch: An Endemic Species of Caucasian Flora

Background: The genus Teucrium L. is frequently employed in traditional medicine, primarily for addressing disorders of the digestive and respiratory systems. Biological investigations focused on essential oils have substantiated their antibacterial, antioxidant, anti-tumor, anti-diabetic, and anti-rheumatic properties. Objective: The aim of the study was to assess the chemical composition and biological activities of the aerial parts of the endemic species Teucrium nuchense K. Koch. Methods: The chemical composition of the essential oil was analyzed using gas chromatography-mass spectrometry (GC-MS). The antioxidant activity was evaluated through the Oxygen Radical Absorbance Capacity (ORAC) assay and tested on normal skin fibroblasts (WS-1). Additionally, the antiinflammatory efficacy was assessed by monitoring nitric oxide production. The total phenolic content in the aqueous, methanolic, and chloroformic extracts was quantified using the Folin-Ciocalteu reagent. Individual compounds were isolated using preparative high-performance liquid chromatography. Their identification was accomplished using high-resolution mass spectrometry (HRMS) with an ESI-Q-TOF detector in conjunction with nuclear magnetic resonance (NMR) spectroscopy. Results: The essential oil yield was 0.32 ml/kg. Caryophyllene oxide, constituting 15.19 %, and 1- octen-3-ol, constituting 8.75%, emerged as the primary components in the essential oil. Oxygenated sesquiterpenes dominated the terpenic compounds, representing 25.1 % of the essential oil. The aqueous and methanolic extracts displayed a notable phenolic content, with percentages of 27 ± 2 % and 35 ± 0.1 %, respectively. Both the aqueous and methanolic extracts demonstrated robust antioxidant activity in the ORAC test and in vitro assessments using WS-1 cells. The methanolic extract, at a concentration of 160 μg/ml, inhibited NO formation by 90 %, without toxicity in RAW 264.7. Individual compounds, teucrioside from the phenylethanoid glycoside class, two neo-clerodane diterpenes, teucrin A, and 6-alpha-hydroxyteuscordine, were isolated. Conclusion: The essential oil extracted from the aerial parts of Teucrium nuchense is characterized by the presence of caryophyllene oxide and 1-octen-3-ol. The methanolic extract exhibits notable antioxidant as well as anti-inflammatory properties, whereas the aqueous extract demonstrates high antioxidant activity. Additionally, three compounds of teucrioside, teucrin A, and 6-α- hydroxyteuscordine have been isolated and characterized.

Evaluating larvicidal, ovicidal and growth inhibiting activity of five medicinal plant extracts on Culex pipiens (Diptera: Culicidae), the West Nile virus vector

Mosquitoes, one of the deadliest animals on the planet, cause millions of fatalities each year by transmitting several human illnesses. Synthetic pesticides were previously used to prevent the spread of diseases by mosquitoes, which was effective in protecting humans but caused serious human health problems, environmental damage, and developed mosquito pesticide resistance. This research focuses on exploring new, more effective, safer, and environmentally friendly compounds to improve mosquito vector management. Phytochemicals are possible biological agents for controlling pests and many are target-specific, rapidly biodegradable, and eco-friendly. The potential of extracts of Lantana camara, Melia azedarach, Nerium oleander, Ricinus communis, and Withania somnifera against 3rd instar Culex pipiens (Common house mosquito) larvae was evaluated. Methanol extracts had more toxic effects against Cx. pipiens larvae (95–100%, 24 h post-treatment) than aqueous extracts (63–91%, 24 h post-treatment). The methanol extracts of Nerium oleander (LC50 = 158.92 ppm) and Ricinus communis (LC50 = 175.04 ppm) were very effective at killing mosquito larvae, 24 h after treatment. N. oleander (LC50 = 373.29 ppm) showed high efficacy in aqueous plant extracts. Among the different extracts of the five plants screened, the methanol extract of R. communis recorded the highest ovicidal activity of 5% at 800 ppm concentration. Total developmental duration and growth index were highly affected by R. communis and M. azedarach methanol extracts. In field tests it was clear that plant extracts decreased mosquito larval density, especially when mixed with mosquito Bti briquette, with stability up to seven days for N. oleander. GC–MS results showed that the methanol extract had a higher number of chemical compounds, particularly with more terpene compounds. A high-performance liquid chromatography (HPLC) technique was used to detect the existence of non-volatile polyphenols and flavonoids. All five methanol extracts showed high concentrations of active ingredients such as gallic acid, chlorogenic acid (more than 100 μg/ml) and the rosmarinic acid was also found in all the five extracts in addition to 17 active polyphenols and flavonoids presented at moderate to low concentrations. Molecular modeling of 18 active ingredients detected by the HPLC were performed to the vicinity of one of the fatty acid binding proteins of lm-FABP (PDB code: 2FLJ). Rutin, Caffeic acid, coumaric acid and rosmarinic acid which presented densely in R. communis and N. oleander showed multiple and stable intermolecular hydrogen bonding and π–π stacking interactions. The inhibition ability of the fatty acid binding protein, FABP4, was evaluated with remarkable receptor inhibition evident, especially with R. communis and N. oleander having inhibitory concentrations of IC50 = 0.425 and 0.599 µg/mL, respectively. The active phytochemical compounds in the plants suggest promising larvicidal and ovicidal activity, and have potential as a safe and effective alternative to synthetic insecticides.

Investigation of the phytochemical profiling and antioxidant, anti-diabetic, anti-inflammatory, and MDA-MB-231 cell line antiproliferative potentials of extracts from Ephedra alata Decne

Ephedra is one of the many medicinal herbs that have been used as folk/traditional medicine in Jordan and other countries to cure various illnesses. Plants of this genus are well known for their antioxidant and antibacterial properties. In this study, three different solvents were used to obtain Ephedra extracts. When evaluated, the Ephedra alata Decne ethanolic extract reportedly had the greatest levels of total phenolic compounds (TPC) and total flavonoid compounds (TFC). The aqueous extracts displayed the highest antioxidant activity in the DPPH and ABTS assays, demonstrating their considerable capacity to neutralize free radicals. However, when evaluated using the FRAP method, the acetone extracts showed the strongest antioxidant activity, indicating their high reducing power. LC–MS/MS, a potent method of analysis that combines the liquid chromatographic separation properties with mass spectrometry detection and identification capabilities, was used in this study to detect and measure phytochemical content of a total of 24 phenolic compounds and 16 terpene compounds present in the extracts of Ephedra alata Decne. Various concentrations of these chemicals were found in these extracts. The extracts’ inhibitory effects on albumin denaturation and alpha-amylase activity were also assessed; the findings demonstrated the potentials of these extracts as anti-inflammatory and anti-diabetic medicines, with the acetone extract having the lowest IC50 values in the concomitant tests (306.45 µg/ml and 851.23 µg/ml, respectively). Furthermore, the lowest IC50 value (of 364.59 ± 0.45 µg/ml) for the 80% ethanol extract demonstrated that it has the strongest antiproliferative impact regarding the MDA-MB-231 breast cancer cell line. This finding indicates that this particular extract can be potentially used to treat cancer.

Disease suppression efficacy of Dysoxylum terpenoids against the bacterial sheath light pathogen, Xanthomonasoryzae pv. oryzae (Xoo) on susceptible rice (Oryza sativa L) through induced resistance through biocatalysis

The severe disease Xanthomonasoryzae pv. oryzae (Xoo) causes in rice plants is known as rice bacterial blight.As a result of the risks associated with the indiscriminate use of chemical pesticides, bio elicitors derived from plant sources may be sought after as superior and safer substitutes. Thus, the objective of the current study was to assess the potential of terpenes from Dysoxylummalabaricum (D. Meliaceae) leaf to promote plant defence and provide protection from Xoo. It was observed that D. malabaricum leaves contained eight major terpene compounds (DMT). The application of DMT induced defence enzyme synthesis (peroxidase, PO - polyphenol oxidase, PPO) and accumulation till 120 h post treatment and their levels increased further post infection of Xoo. Direct suppression of Xoo growth in-vitro evidently decreased disease incidence and severity offering effective disease control, consequently enhancing plant growth parameters and biomass. Overall, our study suggests that D. malabaricum terpenes have a significant role in preventing the growth of Xoo in rice plants, providing long-term plant protection.

Evaluation of the essential oil and tea produced from Baccharis myriocephala leaves

ABSTRACT Baccharis myriocephala is a carqueja species less studied than other Baccharis species. This study evaluated the chemical composition, toxicological and antioxidant potentials of the essential oils and infusions of B. myriocephala. Essential oils (hydrodistillation) and the volatile fractions of infusions (SPE) were analyzed by chromatographic techniques. The TPC and TFC of the infusions, and the antioxidant activities of essential oils and infusions were measured by spectrophotometry; their toxicological potentials were evaluated by Artemia salina bioassay (ASB). Twenty-eight terpenic compounds were identified in the essential oils, fourteen of them for the first time. Nine compounds were identified in the volatile fraction of the infusions, and seven of them were absent in essential oils. Infusions [IC50(DPPH) = 2.21 mg mL−1] are better antioxidants than the essential oils [IC50(DPPH) = 40.37 mg mL−1]. The essential oils were considered highly cytotoxic (LD50 = 26.64 μg mL−1), according to the ASB.

Investigation the effect of the aqueous extract of Chara vulgaris (L.) on visceral leishmaniasis.

Visceral leishmaniasis (VL) is a parasitic disease that affects public health. It is described by weight reduction, irregular fever bouts, anemia, and amplification of the spleen and liver. Three concentrations (15.6, 31.2, and 62.5 μg/mL) were used to find the potency of an aqueous extract of Chara vulgaris algae in the treatment of VL. A cytotoxicity assay was performed to show the cytotoxic effect of this extract on human cells. High-performance liquid chromatography (HPLC) test was done to determine the active compounds in the extract. Histopathological sections for infected liver and spleen were performed, as were liver function tests (alanine aminotransferase, aspartate aminotransferase, and alkaline phosphatase), which were assessed after 1 month of treatment. As cytotoxicity assay, results showed that there were no significant differences between the cells treated and those not treated with the extract. HPLC test demonstrated that phenolic and terpene compounds are the main active compounds in the extract. P-coumaric acid and ursolic acid present the highest percent among other phenolic and terpene compounds (21.84%, 17.82%), respectively. Histopathological sections showed that this extract had a significant effect in the treatment of infected tissues, and this effect was very clear after the end of the treatment period. As for the liver function tests, a significant increase (P < 0.01) in the studied liver enzymes was found in the infected group of mice compared to the healthy group, whereas in the infected and treated groups, a clear and gradual decrease in the level of enzymes was observed.

Artemisia fragrans Willd. Essential Oil: Chemical Profile and Insecticidal Potential against the Confused Flour Beetle, Tribolium confusum du Val.

The confused flour beetle, Tribolium confusum du Val, is one of the cosmopolitan and polyphagous storage insect pests. The frequent application of chemical insecticides has resulted in several side effects, including threats to human health and non-target organisms and the resistance of insect pests. In the current study, the fumigant toxicity and feeding deterrence potential of Artemisia fragrans Willd. essential oil on T. confusum adults were investigated. The essential oil was rich in terpenic compounds, in which α-thujone (27.8%) and 1,8-cineole (22.8%) were dominant. The essential oil displayed significant fumigant toxicity on T. confusum, where a concentration of 35.3 μL/L caused 100% mortality of the treated adults after 48 h. The LC30 and LC40 values (lethal concentrations to kill 30% and 40% of tested insects: 15.1 and 18.4 μL/L, respectively) significantly decreased the nutritional indices of the pest, including the consumption index, relative consumption rate, and relative growth rate. The feeding deterrence index of the essential oil were calculated as being 62.29 and 48.66% for the concentrations of 15.1 and 18.4 μL/L after 5 days, respectively. Accordingly, A. fragrans essential oil can be considered an efficient, available, and natural alternative to detrimental chemical pesticides in the management of T. confusum.

Theoretical Study of Natural Product Biosynthesis Using Computational Chemistry.

The biosynthetic pathways of natural products are complicated, and it is difficult to fully elucidate their details using experimental chemistry alone. In recent years, efforts have been made to elucidate the biosynthetic reaction mechanisms by combining computational and experimental methods. In this review, we will discuss the biosynthetic studies using computational chemistry for various terpene compounds such as cyclooctatin, sesterfisherol, quiannulatene, trichobrasilenol, asperterpenol, preasperterpenoid, spiroviolene, and mangicol.

Phytochemical characterization and multifaceted bioactivity assessment of essential oil from Clinopodium nepeta subsp. ascendens: potential for the food and pharmaceutical sectors

ABSTRACT This study delves into the biological characteristics of Clinopodium nepeta subsp. ascendens (CNEO) essential oil, an indigenous subspecies of eastern Morocco. Distinguished by its purple or pale pinkish-white flowers, CNEO was subjected to thorough phytochemical analysis via gas chromatography-mass spectrometry (GC-MS), revealing 21 terpene compounds, notably Dihydrocarvone (22.70%), Neoisomenthol (43.59%), and Pulegone (20.55%). These compounds, recognized for their biological and pharmacological attributes, were further investigated for their potential applications. Notably, CNEO exhibited dose-dependent anti-inflammatory effects by attenuating nitric oxide (NO) and prostaglandin E2 (PGE2) production. Moreover, it demonstrated promising anticancer activity against MDA-MB-468, HepG2, and HCT-15 cancer cell lines, rivaling doxorubicin’s effectiveness. These findings underscore CNEO’s nutraceutical potential, particularly in food science and industry, suggesting its use as a functional food additive with both nutritional and health benefits

Superparamagnetic iron oxide nanoparticles functionalized by biocompatible ligands with enhanced high specific absorption rate for magnetic hyperthermia

This study introduces a novel green nanocomposite system of iron oxide coated with secondary metabolites (Fe3O4@SM) and compares it with commonly used materials for hyperthermia cancer treatment. Fe3O4@SM magnetic nanoparticles were synthesized through a simple co-precipitation process using metal precursors, followed by heating in pressure reactor to obtain superparamagnetic nanoparticles (Hc = 36.5–54.1 Oe at 300 K). These nanoparticles were subsequently coated with plant-based phytochemicals. XRD analysis confirmed the presence of magnetite iron oxide nanoparticles. SEM images further confirmed the spherical shape of the synthesized nanoparticles, exhibiting a face-centered cubic (FCC) iron oxide structure with sizes ranging from 12±7–85±15 nm. Characterization through dynamic light scattering (DLS) and zeta potential (ζ) analysis demonstrated colloidal stability, with a polydispersity index (PDI) ranging from 0.226 to 0.436 and zeta potential values ranging from −29.761–1.85 mV. The surface of the nanoparticles was analyzed using GC-MS, which identified bioactive functional groups including ester (42.79 %), terpene (20.69 %), hydrocarbons (17.4 %), and carboxylic (12.37 %) compounds. Compared to Fe3O4 and Fe3O4@GO, Fe3O4@SM exhibited a higher rate of temperature increase within the therapeutic range, reaching Tmax = 45°C with a heating rate (dT/dt) of 0.273 °C/s and specific absorption rate (SAR) of 230.6 W/g at 304 kHz and 400 Oe. In vitro assays utilizing a triple negative breast cancer microenvironment confirmed the non-toxicity of these materials through a DNS assay. The developed nanoparticles offer dual mechanisms of action, combining thermal and chemo effects, making them promising candidates for hyperthermia cancer treatment.

Chemical Composition of Volatile and Extractive Components of Canary (Tenerife) Propolis.

The vegetation of the Canary Islands is characterized by a large number of endemic species confined to different altitudinal levels. It can be assumed that these circumstances determine the characteristic features of the chemical composition of local beekeeping products, including propolis. We report, for the first time, the chemical composition of propolis from Tenerife (Canary Islands). The volatile emissions of three propolis samples collected from different apiaries are represented by 162 C1-C20 compounds, of which 144 were identified using the HS-SPME/GC-MS technique. The main group of volatiles, consisting of 72 compounds, is formed by terpenoids, which account for 42-68% of the total ion current (TIC) of the chromatograms. The next most numerous groups are formed by C6-C17 alkanes and alkenes (6-32% TIC) and aliphatic C3-C11 carbonyl compounds (7-20% TIC). The volatile emissions also contain C1-C6 aliphatic acids and C2-C8 alcohols, as well as their esters. Peaks of 138 organic C3-C34 compounds were recorded in the chromatograms of the ether extracts of the studied propolis. Terpene compounds form the most numerous group, but their number and content in different samples is within very wide limits (9-63% TIC), which is probably due to the origin of the samples from apiaries located at different altitudes. A peculiarity of the chemical composition of the extractive substances is the almost complete absence of phenylcarboxylic acids and flavonoids, characteristic of Apis mellifera propolis from different regions of Eurasia and North America. Aromatic compounds of propolis from Tenerife are represented by a group of nine isomeric furofuranoid lignans, as well as alkyl- and alkenyl-substituted derivatives of salicylic acid and resorcinol.