Facile Synthesis and First Antifungal Exploration of Tetracyclic Meroterpenoids: (+)-Aureol, (-)-Pelorol, and Its Analogs.

As an important bioactive molecular backbone, drimane meroterpenoids have drawn a great deal of attention from both pharmacologists and chemists. Inspired by the prevalidated success of conformational restriction in the discovery of novel pharmaceutical leads, two distinct tetracyclic drimane meroterpenoids, (-)-pelorol and (+)-aureol, were synthesized from the inexpensive starting material (-)-sclareol through 10 and 8 steps with 5.6% and 5.4% overall yield, respectively. The mild conditions, operational facility, and scalability enabled the expedient synthesis and biological exploration of not only natural products themselves but also their mimics. The first agrochemical exploration showed (-)-pelorol and (+)-aureol possessed good antifungal activity against Rhizoctonia solani, with EC50 values of 7.7 and 6.9 µM, respectively. This revealed that tetracyclic drimane meroterpenoids are valuable models for antifungal lead discovery.

Bioinformatics-Guided Reconstitution of Biosynthetic Machineries of Fungal Eremophilane Sesquiterpenes.

Eremophilanes exhibit diverse biological activities and chemical structures. This study reports the bioinformatics-guided reconstitution of the biosynthetic machinery of fungal eremophilanes, eremofortin C and sporogen-AO1, to elucidate their biosynthetic pathways. Their biosyntheses include P450-catalyzed multistep oxidation and enzyme-catalyzed isomerization by the DUF3237 family protein. Successful characterization of six P450s enabled us to discuss the functions of eremophilane P450s in putative eremophilane biosynthetic gene clusters, providing opportunities to understand the oxidative modification pathways of fungal eremophilanes.

Total Synthesis of a TNBC-Selective Cytotoxic Bromo Nor-eremophilane, PC-A, and Its Preliminary Structure-Activity Relationships.

PC-A (1), a bromo nor-eremophilane, showed selective antiproliferative activity against a triple-negative breast cancer (TNBC) cell line. This unique activity prompted us to establish a total synthesis to facilitate a structure-activity relationship (SAR) study and selectivity optimization. An enantioselective first total synthesis of 1 was achieved starting from (R)-carvone through a side chain extension with a Mukaiyama aldol reaction and decalin construction. The synthesized decalin derivatives and debromo PC-A (2) were evaluated for antiproliferative activity against five human tumor cell lines, including TNBC, to assess preliminary SAR correlations.

Exploring the composition and potential uses of four hops varieties through different extraction techniques.

Hydrophilic, lipophilic extracts and essential oil of four hops varieties from Slovenia were examined in this study. Lipophilic extracts were obtained by supercritical extraction (SFE), while for hydrophilic extracts ultrasound and microwave extraction were employed. Essential oils were isolated by the hydrodistillation process. The lipophilic composition of essential oils and lipophilic extracts was determined by GC-MS analysis. Monoterpenes and sesquiterpene hydrocarbons were the most abundant class of compounds in oils (62.27-79.65 %), with myrcene being the most abundant constituent. Limonene and trans-caryophyllene were two terpenes determined in all essential oils while only trans-caryophyllene was detected in SFE samples. Antioxidant, antimicrobial, and cytotoxic activity, determined by applying in vitro assays, was more influenced by extraction technique than by varieties. Molecular docking was carried out to gain insight into the potential cancer protein targets BCL-2 and MMP9, whereby humulene epoxide II displayed good binding configuration within the cavities of the two proteins.

Effect of free and nanoemulsified ß-caryophyllene on monocrotaline-induced pulmonary arterial hypertension.

Pulmonary arterial hypertension (PAH) is characterized by increased pulmonary vascular resistance (PVR), right ventricular (RV) failure and premature death. Compounds with vasodilatory characteristics, such as ß-caryophyllene, could be promising therapeutics for PAH. This study aimed to determine the effects of free and nanoemulsified ß-caryophyllene in lung oxidative stress and heart function in PAH rats. Male Wistar rats (170 g, n = 6/group) were divided into four groups: control (CO), monocrotaline (MCT), monocrotaline + ß-caryophyllene (MCT-Bcar) and monocrotaline + nanoemulsion with ß-caryophyllene (MCT-Nano). PAH was induced by MCT (60 mg/kg i.p.), and 7 days later, treatment with ß-caryophyllene, either free or in a nanoemulsion (by gavage, 176 mg/kg/day) or vehicle was given for 14 days. Echocardiographic and hemodynamic measurements were performed, and after, the RV was collected for morphometry and the lungs for evaluation of oxidative stress, antioxidant enzymes, total sulfhydryl compounds, nitric oxide synthase (NOS) activity and endothelin-1 receptor expression. RV hypertrophy, increased PVR and RV systolic and diastolic pressures (RVSP and RVEDP, respectively) and increased mean pulmonary arterial pressure (mPAP) were observed in the MCT group. Treatment with both free and nanoemulsified ß-caryophyllene reduced RV hypertrophy, mPAP, RVSP and lipid peroxidation. The reduction in RVSP was more pronounced in the MCT-Nano group. Moreover, RVEDP decreased only in the MCT-Nano group. These treatments also increased superoxide dismutase, catalase and NOS activities and decreased endothelin-1 receptors expression. Both ß-caryophyllene formulations improved mPAP, PVR and oxidative stress parameters. However, ß-caryophyllene in a nanoemulsion was more effective in attenuating the effects of PAH.

Dimeric eremophilane-type sesquiterpenoids from the peeled stems of Syringa pinnatifolia.

A continued phytochemical investigation guided by 1H NMR and LC-MS data on the ethanol extract from the peeled stems of Syringa pinnatifolia Hemsl. led to the isolation of 16 undescribed dimeric eremophilane sesquiterpenoids, namely syringenes R-Z (1-9) and A1-G1 (10-16). These structures were elucidated by extensive analysis of spectroscopic data, including HRESIMS, NMR, quantum-mechanics-based computational analysis of NMR chemical shifts, and single-crystal X-ray diffraction analyses, and a concise rule for determination of relative configuration of angular methyl was proposed. The results of the cardioprotective assay demonstrated that 3 exhibits a protective effect against hypoxia-induced injuries in H9c2 cells. This effect was observed at a concentration of 10 µM, with a protective rate of 28.43 ± 11.80%.

Functional characterization of terpene synthases SmTPS1 involved in floral scent formation in Salvia miltiorrhiza.

Plants attract beneficial insects and promote pollination by releasing floral scents. Salvia miltiorrhiza, as an insect-pollinated flowering plant, which has been less studied for its floral aroma substances. This study revealed that S. miltiorrhiza flowers produce various volatile terpenoids, including five monoterpenes and ten sesquiterpenes, with the sesquiterpene compound (E)-ß-caryophyllene being the most abundant, accounting for 28.1% of the total volatile terpenoids. Y-tube olfactometer experiments were conducted on the primary pollinator of S. miltiorrhiza, the Apis ceranas. The results indicated that (E)-ß-caryophyllene compound had an attractive effect on the Apis ceranas. By comparing the homologous sequences with the genes of (E)-ß-caryophyllene terpene synthases in other plants, the SmTPS1 gene was selected for further experiment. Subcellular localization experiments showed SmTPS1 localized in the cytoplasm, and its in vitro enzyme assay revealed that it could catalyze FPP into ß-Elemene, (E)-ß-caryophyllene and α-Humulene. Overexpression of SmTPS1 in S. miltiorrhiza resulted in a 5.29-fold increase in gene expression. The GC-MS analysis revealed a significant increase in the concentration of (E)-ß-caryophyllene in the transgenic plants, with levels 2.47-fold higher compared to the empty vector plants. Furthermore, Y-tube olfactometer experiments showed that the transgenic plants were significantly more attractive to Apis ceranas compared to the empty vector plants. Co-expression analysis suggested that four SmMYCs (SmMYC1, SmMYC5, SmMYC10, and SmMYC11) may be involved in the transcriptional regulation of SmTPS1. The yeast one-hybrid screen and the Dual luciferase assay indicated that SmMYC10 positively regulates the expression of SmTPS1. In conclusion, this study lays a foundation for the functional analysis and transcriptional regulation of terpene synthase genes in S. miltiorrhiza.

Liposomal nanoformulations with trans-caryophyllene and caryophyllene oxide: do they have an inhibitory action on the efflux pumps NorA, Tet(K), MsrA, and MepA?

This study aimed to evaluate the antibacterial and inhibitory action of NorA, Tet(K), MsrA and MepA efflux pumps in S. aureus strains using the sesquiterpenes named trans-caryophyllene and caryophyllene oxide, both isolated and encapsulated in liposomes. The antibacterial and inhibitory action of these efflux pumps was evaluated through the serial microdilution test in 96-well microplates. Each sesquiterpene and liposome/sesquiterpene was combined with antibiotics and ethidium bromide (EtBr). The antibiotics named norfloxacin, tetracycline and erythromycin were used. The 1199 B, IS-58, RN4220 and K2068 S. aureus strains carrying NorA, Tet(K), MsrA and MepA, respectively, were tested. In the fluorescence measurement test, K2068 S. aureus was incubated with the sesquiterpenes and EtBr, and the fluorescence emission by EtBr was measured. The tested substances did not show direct antibacterial activity, with MIC >1024 µg/mL. Nonetheless, the isolated trans-caryophyllene and caryophyllene oxide reduced the MIC of antibiotics and EtBr, indicating inhibition of NorA, Tet(K) and MsrA. In the fluorescence test, these same sesquiterpenes increased fluorescence emission, indicating inhibition of MepA. Therefore, the sesquiterpenes named trans-caryophyllene and caryophyllene oxide did not show direct antibacterial action; however, in their isolated form, they showed possible inhibitory action on NorA, Tet(K), MsrA and MepA efflux pumps. They may also act in antibiotic potentiation. Further studies are needed to identify the mechanisms involved in antibiotic potentiation and efflux pump inhibitory action.

Chemical Composition of Essential Oils from Natural Populations of Artemisia scoparia Collected at Different Altitudes: Antibacterial, Mosquito Repellent, and Larvicidal Effects.

The current study aimed to evaluate the presence of chemical variations in essential oils (EOs) extracted from Artemisia scoparia growing at different altitudes and to reveal their antibacterial, mosquito larvicidal, and repellent activity. The gas chromatographic-mass spectrometric analysis of A. scoparia EOs revealed that the major compounds were capillene (9.6-31.8%), methyleugenol (0.2-26.6%), ß-myrcene (1.9-21.4%), γ-terpinene (1.5-19.4%), trans-ß-caryophyllene (0.8-12.4%), and eugenol (0.1-9.1%). The EO of A. scoparia collected from the city of Attock at low elevation was the most active against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa bacteria (minimum inhibitory concentration of 156-1250 µg/mL) and showed the best mosquito larvicidal activity (LC50, 55.3 mg/L). The EOs of A. scoparia collected from the high-altitude areas of Abbottabad and Swat were the most repellent for females of Ae. aegypti and exhibited repellency for 120 min and 165 min, respectively. The results of the study reveal that different climatic conditions and altitudes have significant effects on the chemical compositions and the biological activity of essential oils extracted from the same species.

[ß-Caryophyllene downregualtes inflammatory cytokine expression and alleviates systemic inflammation in mice by inhibiting the NF-κB signaling pathway].

Objective To investigate the anti-inflammatory mechanism of ß-caryophyllene (BCP) on lipopolysaccharide (LPS)-induced systemic inflammation in mice. Methods C57BL mice were divided into control group, LPS-treated group, dexamethasone-treated group, and BCP-treated group. Twelve hours after the establishment of the whole body inflammation model by intraperitoneal injection of LPS, the serum levels of interleukin 1ß(IL-1ß), tumor necrosis factor α (TNF-α), and IL-6 were measured by ELISA. The protein levels of nuclear factor κB p65(NF-κB p65), myeloid differentiation primary response 88 (MyD88), and Toll-like receptor 4 (TLR4) in spleen tissue were assessed by Western blot analysis. ResultsCompared with the control group, the serum levels of the inflammatory cytokines IL-1ß, TNF-α and IL-6 in the LPS-treated group were significantly increased. In addition, the pro-tein levels of NF-κB p65, MyD88 and TLR4 were increased in spleen tissues. Compared with the LPS-treated group, the protein levels of IL-1ß, TNF-α and IL-6 in the BCP-treated group were decreased significantly. Furthermore, the protein levels of NF-κB p65, MyD88 and TLR4 in spleen tissue showed a remarkable reduction. The inhibitory effect was notably better in the 3.5 µg/(L.d) BCP-treated group than in the 3 µg/(L.d) BCP-treated group. Conclusion BCP exerts anti-inflammatory effects by downregulating inflammatory cytokine expression through the inhibition of the NF-κB signaling pathway.

Beta-Caryophyllene, a Cannabinoid Receptor Type 2 Selective Agonist, in Emotional and Cognitive Disorders.

Mental disorders account for one of the most prevalent categories of the burden of disease worldwide, with depression expected to be the largest contributor by 2030, closely followed by anxiety. The COVID-19 pandemic possibly exacerbated these challenges, especially amongst adolescents, who experienced isolation, disrupted routines, and limited healthcare access. Notably, the pandemic has been associated with long-term neurological effects known as "long-COVID", characterized by both cognitive and psychopathological symptoms. In general, psychiatric disorders, including those related to long-COVID, are supposed to be due to widespread inflammation leading to neuroinflammation. Recently, the endocannabinoid system (ECS) emerged as a potential target for addressing depression and anxiety pathophysiology. Specifically, natural or synthetic cannabinoids, able to selectively interact with cannabinoid type-2 receptor (CB2R), recently revealed new therapeutic potential in neuropsychiatric disorders with limited or absent psychotropic activity. Among the most promising natural CB2R ligands, the bicyclic sesquiterpene ß-caryophyllene (BCP) has emerged as an excellent anti-inflammatory and antioxidant therapeutic agent. This review underscores BCP's immunomodulatory and anti-inflammatory properties, highlighting its therapeutic potential for the management of depression and anxiety.

Novel drimane-type sesquiterpenoids and nucleosides from the Helicoma septoconstrictum suppress the growth of ovarian cancer cells.

Four new drimane-type sesquiterpenoids and two new nucleoside derivatives (1-6), were isolated from the fungus Helicoma septoconstrictum. Their structures were determined based on the combination of the analysis of their HR-ESI-MS, NMR, ECD calculations data and acid hydrolysis. All the isolated compounds were detected for their bio-activities against MDA-MB-231, A549/DDP, A2780 and HepG2 cell lines. Helicoside C (4) exhibited superior cytotoxicity against the A2780 cell line with IC50 7.5 ± 1.5 µM. The analysis of reactive oxygen species (ROS) revealed that Helicoside C induced an increase in intracellular ROS. Furthermore, the flow cytometry and mitochondrial membrane potential (MMP) analyses unveiled that Helicoside C mediated mitochondrial-dependent apoptosis in A2780 cells. The western blotting test showed that Helicoside C could suppress the STAT3's phosphorylation. These findings offered crucial support for development of H. septoconstrictum and highlighted the potential application of drimane-type sesquiterpenoids in pharmaceuticals.

Protoilludane-Type and Related Nor-Sesquiterpenes from Phellinus hartigii and Their Anti-Hypertrophic Activities in Rat Cardiomyocytes.

Three nor-sesquiterpenes, phellinharts A-C (1-3), isolated from Phellinus hartigii, exhibited unprecedented protoilludane and cerapicane-type structures. The structures of compounds 1-3 were elucidated via spectroscopic analysis, quantum chemical calculations, and X-ray diffraction. Potential biogenic pathways involving demethylation, ring cleavage, and rearrangement were proposed. Compounds 1-3 displayed potent anti-hypertrophic activities with low cytotoxicity (CC50 > 50 µM) in rat cardiomyocytes, underscoring their therapeutic potential.

Divergent Biosynthesis of Bridged Polycyclic Sesquiterpenoids by a Minimal Fungal Biosynthetic Gene Cluster.

The bridged polycyclic sesquiterpenoids derived from sativene, isosativene, and longifolene have unique structures, and many chemical synthesis approaches with at least 10 steps have been reported. However, their biosynthetic pathway remains undescribed. A minimal biosynthetic gene cluster (BGC), named bip, encoding a sesquiterpene cyclase (BipA) and a cytochrome P450 (BipB) is characterized to produce such complex sesquiterpenoids with multiple carbon skeletons based on enzymatic assays, heterologous expression, and precursor experiments. BipA is demonstrated as a versatile cyclase with (-)-sativene as the dominant product and (-)-isosativene and (-)-longifolene as minor ones. BipB is capable of hydroxylating different enantiomeric sesquiterpenes, such as (-)-longifolene and (+)-longifolene, at C-15 and C-14 in turn. The C-15- or both C-15- and C-14-hydroxylated products are then further oxidized by unclustered oxidases, resulting in a structurally diverse array of sesquiterpenoids. Bioinformatic analysis reveals the BipB homologues as a discrete clade of fungal sesquiterpene P450s. These findings elucidate the concise and divergent biosynthesis of such intricate bridged polycyclic sesquiterpenoids, offer valuable biocatalysts for biotransformation, and highlight the distinct biosynthetic strategy employed by nature compared to chemical synthesis.

Synergistic treatment of androgenetic alopecia with follicular co-delivery of minoxidil and cedrol in metal-organic frameworks stabilized by covalently cross-linked cyclodextrins.

Androgenetic alopecia seriously affects the physical and mental health of patients. The main clinical therapeutic agent, minoxidil tincture, is challenged by solvent irritation and dose-dependent side effects. Our recent work has identified a biosafety natural product, cedrol, that is synergistic in combination with minoxidil, thereby improving medication safety by substantially reducing the clinical dose of minoxidil. In addition, ccross-linked CD-MOF were designed as carriers for hair follicle delivery, and γ-CD in the carriers was cross-linked by diphenyl carbonate with covalent bonds to protect the CD-MOF from rapid disintegration in an aqueous environment. This improved nanocarrier has a drug loading of 25%, whereas nanocarriers increased drug delivery to the hair follicles through ratchet effect, and increased human dermal papilla cells uptake of drugs via endocytosis pathways mainly mediated by lattice proteins, energy-dependent active transport, and lipid raft-dependent, thus improved cell viability, proliferation, and migration, followed by significantly enhancing the anti-androgenetic alopecia effect, with cedrol focusing on inhibiting 5α-reductase and activating Shh/Gli pathway, and minoxidil, which up-regulated VEGF, down-regulated TGF-ß, and activated ERK/AKT pathway. This drug combination provides a new therapeutic strategy for androgenetic alopecia, while the newly developed cross-linked CD-MOF has been shown to serve as a promising follicular delivery vehicle.

New sesquiterpenoids from Biscogniauxia sp.

Five new sesquiterpenoids, including a campherenane-type (1), a bergamotane-type (2), a drimane-type (3), and two bisabolane-type (5-6) sesquiterpenoids have been isolated from Biscogniauxia sp. 71-10-1-1. Their structures were determined by spectroscopic analyses, quantum chemical ECD calculations,13C chemical shifts calculations, and X-ray crystallography. This is the first report of campherenane-type and drimane-type sesquiterpenoids from Biscogniauxia. Furthermore, the anti-inflammatory assays of all compounds are evaluated, and the results showed that compounds 3 and 7 exhibited the effects against the production of the pro-inflammatory cytokine TNF-α.

Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam.

Eryngium dilatatum Lam. is a thorny Iberian Peninsula endemic species belonging to the Apiaceae family that has not been previously analysed from a chemical point of view. Following our studies on this genus, we characterized the chemical composition of the essential oils from the different parts (inflorescences, stems + leaves, and roots) of this species; these parts were gathered in Cádiz (Spain). The specimens were collected in July during the flowering period and air-dried before the oil extraction by hydro-distillation. The essential oils were analysed by gas chromatography and gas chromatography coupled with mass spectrometry. The different parts of the plant yielded low amounts of pale yellow oil, with the roots being the fraction that provided the lowest amount of oil. The chemical characterization of the essential oils showed qualitative and quantitative differences between the fractions examined, but all of them showed the same principal compound, germacrene D (9.1-46.5%). Similarly, all the fractions shared most of their representative constituents, with their percentage compositions being different from one sample to the other: α-cadinol (3.8%), bicyclogermacrene (3.5%), octanal (3.1%), and spathulenol (2.5%) were found in the inflorescences; octanal (8.1%), α-cadinol (3.7%), δ-cadinene (3.6%), (E)-caryophyllene (2.6%), bicyclogermacrene (2.5%), and spathulenol (2.4%) were found in the stems and leaves; and spathulenol (4.6%), α-cadinol (4.4%), khusinol (3.2%), α-muurolol (3.1%), and δ-cadinene (2.6%) were found in the roots. As far as we know, this is the first report about the chemical composition of this endemic species of the Iberian Peninsula. It contributes to the knowledge of this species and to the genus to which it belongs. This species could be considered as a natural source of germacrene D, which is a sesquiterpene hydrocarbon with active properties.

Chemical profile of Juniperus excelsa M. Bieb. essential oil within and between populations and its weed seed suppression effect.

The aims of this study were to (1) establish the intrapopulation and seasonal variation of Juniperus excelsа essential oil (EO); (2) compare the J. excelsa concrete and resinoid composition with its EO composition; and (3) investigate the potential herbicidal activity of J. excelsa EO against seeds of Papaver rhoeas L., Consolida orientalis (J.Gay) Schrödinger, Anthemis arvensis L., Avena fatua L., and Agrostemma githago L. Four independent studies were performed to meet these objectives. Twenty-eight individual trees were analyzed from two populations to establish intrapopulation and interpopulation variability of EOs yield and composition. In the seasonal dynamic study of leaf EO, samples from the same three trees and in the same population were collected in January, March, May, July, October, and December and their EO yield and composition determined. The EOs (intrapopulation and seasonal) were extracted by hydrodistillation, while the EO for the herbicidal test was obtained by steam distillation in a semi-commercial (SCom) apparatus. Overall, the EO yield varied significantly from 0.93% to 2.57%. α-Pinene (8.85-35.94%), limonene (11.81-50.08%), and cedrol (3.41-34.29%) were the predominant EO compounds in all samples (intrapopulation variability); however, trans-2,4-decadienol and ß-caryophyllene were predominant in some individual trees. Four chemical groups were identified in the samples collected from two natural populations (intrapopulation). This is the first report on the compositions of J. excelsa concrete and resinoid. Cedrol (15.39%), 7-hydroxy-4-methyl-coumarin (17.63%), 1-octacosanol (36.85%), tritriacontane (16.08%), and tiacontanoic acid were the main compounds in the concrete and resinoid. Juniperus excelsa EO suppressed seed germination and seedling growth of P. rhoeas, C. orientalis, A. arvensis, A. fatua, and A. githago, demonstrating its potential to be used for the development of new biopesticides. The highest EO yield with high content of limonene and cedrol was obtained from samples harvested during the winter months (December, January, and March).

Three Togolese aromatic plants' essential oils diurnal variations and their insecticidal activities against the dengue vector Aedesaegypti.

The present reported work deals with the ability of Togolese plants' essential oils (EOs) to act as repellents for Aedes aegypti mosquitoes in order to use them as personal protective requirements or actions against mosquito bites and therefore to drastically reduce the risk of contracting dengue or yellow fever. EOs studied here were extracted from dry leaves of Ageratum conyzoides L., Eucalyptus citriodora Hook, and Lantana camara Linn, three plants that were collected at different daytimes (7 a.m., 1 p.m., and 7 p.m.) at various locations in Togo. Using a Clevenger-type device, EOs were obtained by the hydrodistillation method (Clevenger, 1928). The physical parameters of the EOs such as density, refractive index, rotatory power, and organoleptic properties were determined. Then, the characterization of EOs using gas chromatography equipped with a flame ionization detector (GC/FID) and gas chromatography coupled to mass spectrometry (GC/MS) was conducted. Chemical analyses showed the presence of several main compounds from EO samples of the three plants. The major compounds were characterized and identified as: (i) precocene I (67.7, 70.6, and 66.9%) and ß-caryophyllene (17.4, 12.1, and 16.5%) for the EO of A. conyzoïdes; (ii) citronellal (63.3, 67.2, and 75.4%) and citronellol (24.5, 21.4, and 14.3%) for E. citriodora and (iii) ß-caryophyllene (15.3, 11.7, and 12.4%), sabinene (28.4, 35, and 33.3%) and eucalyptol (11.5, 14.1, and 15.6%) for L. camara at 7 a.m., 1 p.m., and 7 p.m., respectively. The yield and the chemical composition of the oils vary according to harvesting time and sunlight. The insecticidal activity of EOs was evaluated following the CDC bottle method on Aedes aegypti females. All the EOs tested on the female adults of Aedes aegypti showed significant insecticidal activity. The EO of A. conyzoïdes at 1 p.m. and 7 p.m. resulted in 100% mortality after 8 min of exposure time at the lowest concentration (0.0025%). At the same concentration for the EO of E. citriodora, the mortality rates were 83%, 38.8%, and 30.80% at 7 a.m., 1 p.m., and 7 p.m., respectively for an exposure time of 8 min. The EO extracted from the leaves of L. camara harvested at 7 a.m. was effective after an exposure time of 15 min for a concentration of 0.02%. For the same concentration, the mortality rates of the EO of L. camara harvested at 1 p.m. and 7 p.m., after 8 min were 62.9% and 52%, respectively. From these interesting results reported for the first time in Togo, EOs from leaves of three Togolese plants harvested at different times of the day appear to be a valuable alternative for mosquito vector control in Togo or abroad countries in which dengue and yellow fever constitute a terrible scourge.

Efficient Capture of Cannabis Terpenes in Olive Oil during Microwave-Assisted Cannabinoid Decarboxylation.

The development of selective extraction protocols for Cannabis-inflorescence constituents is still a significant challenge. The characteristic Cannabis fragrance can be mainly ascribed to monoterpenes, sesquiterpenes and oxygenated terpenoids. This work investigates the entrapment of Cannabis terpenes in olive oil from inflorescences via stripping under mild vacuum during the rapid microwave-assisted decarboxylation of cannabinoids (MW, 120 °C, 30 min) and after subsequent extraction of cannabinoids (60 and 100 °C). The profiles of the volatiles collected in the oil samples before and after the extraction step were evaluated using static headspace solid-phase microextraction (HS-SPME), followed by gas chromatography coupled to mass spectrometry (GC-MS). Between the three fractions obtained, the first shows the highest volatile content (~37,400 mg/kg oil), with α-pinene, ß-pinene, ß-myrcene, limonene and trans-ß-caryophyllene as the main components. The MW-assisted extraction at 60 and 100 °C of inflorescences using the collected oil fractions allowed an increase of 70% and 86% of total terpene content, respectively. Considering the initial terpene amount of 91,324.7 ± 2774.4 mg/kg dry inflorescences, the percentage of recovery after decarboxylation was close to 58% (mainly monoterpenes), while it reached nearly 100% (including sesquiterpenes) after extraction. The selective and efficient extraction of volatile compounds, while avoiding direct contact between the matrix and extraction solvents, paves the way for specific applications in various aromatic plants. In this context, aromatized extracts can be employed to create innovative Cannabis-based products within the hemp processing industry, as well as in perfumery, cosmetics, dietary supplements, food, and the pharmaceutical industry.