Disentangling the chemistry of Australian plant exudates from a unique historical collection.

For thousands of years, the unique physicochemical properties of plant exudates have defined uses in material culture and practical applications. Native Australian plant exudates, including resins, kinos, and gums, have been used and continue to be used by Aboriginal Australians for numerous technical and cultural purposes. A historic collection of well-preserved native Australian plant exudates, assembled a century ago by plant naturalists, gives a rare window into the history and chemical composition of these materials. Here we report the full hierarchical characterization of four genera from this collection, Xanthorrhoea, Callitris, Eucalyptus, and Acacia, from the local elemental speciation, to functional groups and main molecular markers. We use high-resolution X-ray Raman spectroscopy (XRS) to achieve bulk-sensitive chemical speciation of these plant exudates, including insoluble, amorphous, and cross-linked fractions, without the limitation of invasive and/or surface specific methods. Combinatorial testing of the XRS data allows direct classification of these complex natural species as terpenoid, aromatic, phenolic, and polysaccharide materials. Differences in intragenera chemistry was evidenced by detailed interpretation of the XRS spectral features. We complement XRS with Fourier-transform infrared (FT-IR) spectroscopy, gas chromatography­mass spectrometry (GC-MS), and pyrolysis­GC-MS (Py-GC-MS). This multimodal approach provides a fundamental understanding of the chemistry of these natural materials long used by Aboriginal Australian peoples.

Exploring the bio-insecticidal activity of Eucalyptus globulus essential oil/ß-cyclodextrin inclusion complexes: In vitro and in silico assessment against Ephestia kuehniella larvae.

Owing to their beneficial functional capabilities, essential oils were largely used. However, their low aqueous solubility, instability, and high volatility urged scientists to their encapsulation with cyclodextrins (CDs) to tackle their shortcomings. In this study, the co-precipitation method was used to prepare ß-CD/Eucalyptus globulus essential oil (EGEO) inclusion complexes (ICs). ß-CD/EGEO ICs were prepared at ratios (w:w) 1:2 and 1:4 with an encapsulation efficiency of 93 and 96%, respectively. The ICs characterization using the Fourier transform Infrared spectroscopy, differential scanning calorimetry, X-ray powder diffraction, Dynamic Light Scattering, and Laser Doppler Velocimetry confirmed the formation of ß-CD/EGEO ICs. The insecticidal activity of the free EGEO and ICs was explored and displayed that the complex ß-CD/EGEO 1:4 had the highest activity with the lowest LC50 against Ephestia kuehniella larvae (5.03 ± 1.16 mg/g) when compared to the free oil (8.38 ± 1.95 mg/g). Molecular docking simulations stipulated that the compound α-Bisabolene epoxide had the best docking score (ΔG = -7.4 Kcal/mol) against the selected insecticidal target α-amylase. Additionally, toxicity evaluation of the studied essential oil suggested that it could be safely used as a potent bioinsecticide as compared to chemical insecticides. This study reveals that the formation of ß-CD/EGEO ICs enhanced the oil activity and stability and could be a promising and safe tool to boost its application in food or pharmaceutical fields.

Eucalyptus Essential Oil Based Nanoemulsions: Preparation and Biological Activities.

Eucalyptus essential oil has remarkable industrial importance and biological properties due to its effectiveness against various diseases, reported throughout human history. Despite the extraordinary bioactivities of essential oil, its applications are limited due to volatility, insolubility in water, and less stability. Formulation of nanoemulsion is the best way to enhance the bio-efficacy of this essential oil and eliminate the factors responsible for limited application. This review article compiles the information regarding formulation of Eucalyptus essential oil-based nanoemulsion and their several biological activities and medicinal properties including antibacterial, antifungal, larvicidal, insecticidal, and cytotoxic activities etc. The bio-efficacy of essential oil-based nanoemulsion has also been found to be enhanced as compared utilization of essential oil alone. This review can be beneficial for researchers working on medicinal plant-based natural products, specifically containing Eucalyptus essential oil, to explore new research horizons in this emerging field.

Effect of Eucalyptus globulus and Ferula assafoetida essential oils and their nanoformulations on the life table parameters of Tetranychus urticae (Acari: Tetranychidae).

One of the most damaging pests of agricultural crops across the globe is the two-spotted spider mite, Tetranychus urticae Koch. A wide variety of arthropods and plant pathogens can be controlled by essential oils, which are secondary metabolites produced by plants. It is possible to enhance the stability as well as the anti-pest efficiency of plant essential oils by encapsulation. Water distillation was used to extract the essential oils from Eucalyptus globulus and Ferula assafoetida. The chitosan nanoparticles were used to load both essential oils into nanoformulations. Studies were conducted on T. urticae life table characteristics under experimental circumstances to determine the sublethal impacts of essential oils and their nanoformulations. Intrinsic growth rate (r) for population exposed to E. globulus, F. assafoetida essential oils, their nanoformulations and the control were 0.1, 0.069, 0.051, 0.018 and 0.21 per day, respectively. F. assafoetida and E. globulus nanoformulations resulted the lowest fecundity compared to the other treatments. According the result of the lethal and sublethal effects of purified essential oils and nanoformulations of F. assafoetida and E. globulus, they would be recommended for controlling the two-spotted spider mites, T. urticae.

Green synthesis and characterization of magnetite nanoparticles using Eucalyptus globulus leaves for water treatment and agronomic valorization.

This work presents a new process, based on the green nanoparticles Fe3O4 and magnetization coupling for the treatment of saline well water. In this context, iron nanoparticles were synthesized using Eucalyptus globulus leaves. The nanomaterials were characterized by scanning electron microscopy and infrared for identification. Batch experiments were conducted to illustrate the optimal parameters related to contact times and the mass of nanoparticles. The latter marked an optimal contact time of 100 min and a mass of 56 mg/L accompanied by a magnetic treatment for a contact time of 48 min. The results showed a significant (R2 = 0.93) water salinity reduction (67%) and a potential for improvement in the germination of tomato seeds (81%) through the investigation of the evolution of the length of the roots, the stems, and the number of germinated seeds.

Investigation of Eucalyptus camaldulensis and Tamarix aphylla species' capacities for methylene blue removal in wastewater and heavy metal remediation in soil.

In the contemporary landscape, the reuse of wastewater holds paramount significance. Concurrently, wastewater carries an array of pollutants encompassing chemical dyes and heavy metals. This study delves into the potential of Tamarix aphylla (TA) and Eucalyptus camaldulensis (EC) species for mitigating heavy metals in soil and eliminating methylene blue dye (MB) from wastewater. The research begins with assessing the dye adsorption process, considering pivotal factors such as initial pH, adsorbent dosage, initial dye concentration, and contact time. Outcomes reveal EC's superiority in dye removal compared to TA. As a bioremediation agent, EC exhibits a 90.46% removal efficacy for MB within 15 min, with pH 7.0 as the operative condition. Equilibrium analysis employs Temkin (T), Freundlich (F), and Langmuir (L) isotherms, revealing an excellent fit with the L isotherm model. The study delves further by probing surface adsorption kinetics through pseudo-first-order (PFO) and pseudo-second-order (PSO) models. Furthermore, to discern the divergent impacts of EC and TA on soil heavy metal reduction, soil samples were collected from three distinct zones: an untouched control area, alongside areas where EC and TA were cultivated at the Yazd wastewater site in Iran. Heavy metal levels in the soil were meticulously assessed through rigorous measurement and statistical scrutiny. The findings spotlight TA-cultivated soil as having the highest levels across all examined factors. Ultimately, EC emerges as the superior contender, proficiently excelling in both MB eliminations from wastewater and heavy metal amelioration in the soil, positioning it as the preferred phytoremediation agent.

Eucalyptus Oils Phytochemical Composition in Correlation with Their Newly Explored Anti-SARS-CoV-2 Potential: in Vitro and in Silico Approaches.

Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is the latest arisen contagious respiratory pathogen related to the global outbreak of atypical pneumonia pandemic (COVID-19). The essential oils (EOs) of Eucalyptus camaldulensis, E. ficifolia F. Muell., E. citriodora Hook, E. globulus Labill, E. sideroxylon Cunn. ex Woolls, and E. torquata Luehm. were investigated for its antiviral activity against SARS-CoV-2. The EOs phytochemical composition was determined using GC/MS analysis. Correlation with the explored antiviral activity was also studied using multi-variate data analysis and Pearson's correlation. The antiviral MTT and cytopathic effect inhibition assays revealed very potent and promising anti SARS-CoV-2 potential for E. citriodora EO (IC50 = 0.00019 µg/mL and SI = 26.27). The multivariate analysis revealed α-pinene, α-terpinyl acetate, globulol, γ -terpinene, and pinocarvone were the main biomarkers for E. citriodora oil. Pearson's correlation revealed that globulol is the top positively correlated compound in E. citriodora oil to its newly explored potent anti SARS-CoV-2 potential. A molecular simulation was performed on globulol via docking in the main active sites of both SARS-CoV-2 viral main protease (Mpro) and spike protein (S). In silico predictive ADMET study was also developed to investigate the pharmacokinetic profile and predict globulol toxicity. The obtained in silico, in vitro and Pearson's correlation results were aligned showing promising SARS-CoV-2 inhibitory activity of E. citriodora and globulol. This study is a first record for E. citriodora EO as a novel lead exhibiting potent in vitro, and in silico anti SARS-CoV-2 potential and suggesting its component globulol as a promising candidate for further extensive in silico, in vitro and in vivo anti-COVID studies.

Camaldulensals A-C, the First Meroterpenoids Possessing Two Spatially Separated Formyl Phloroglucinols Conjugated to a Terpene Core from the Leaves of Eucalyptus camaldulensis Dehnh.

Three new bis-formyl phloroglucinol-meroterpenoids (1-3), three new euglobal type formyl phloroglucinol-meroterpenoids (4-6), and one new dimeric formyl phloroglucinol (7) were isolated from the leaves of Eucalyptus camaldulensis. Camaldulensal A (1) is the first bis-isovaleryl-formyl-phloroglucinol-sesquiterpenoid. It features a novel 6/6/10/3/6/6 fused ring system and contains six stereogenic centers. Camaldulensals B (2) and C (3) are the first bis-isovaleryl-formyl-phloroglucinols, each conjugated to a monoterpene. Formyl phloroglucinol compounds (FPCs) containing two spatially separated formyl phloroglucinols conjugated to a terpene core such as 1-3 have not been reported previously. The structures of these compounds were elucidated by spectroscopic methods and computational analysis. Camaldulensals B (2) and C (3) exhibited significant antibacterial activity against methicillin-susceptible and methicillin-resistant Staphylococcus aureus. Structure activity relationships are discussed in relation to previously reported antibacterial activities of other molecules from the FPC structure class.

NMR Fingerprints of Formyl Phloroglucinol Meroterpenoids and Their Application to the Investigation of Eucalyptus gittinsii subsp. gittinsii.

NMR fingerprints provide powerful tools to identify natural products in complex mixtures. Principal component analysis and machine learning using 1H and 13C NMR data, alongside structural information from 180 published formyl phloroglucinols, have generated diagnostic NMR fingerprints to categorize subclasses within this group. This resulted in the reassignment of 167 NMR chemical shifts ascribed to 44 compounds. Three pyrano-diformyl phloroglucinols, euglobal In-1 and psiguadiols E and G, contained 1H and 13C NMR data inconsistent with their predicted phloroglucinol subclass. Subsequent reinterpretation of their 2D NMR data combined with DFT 13C NMR chemical shift and ECD calculations led to their structure revisions. Direct covariance processing of HMBC data permitted 1H resonances for individual compounds in mixtures to be associated, and analysis of their 1H/13C HMBC correlations using the fingerprint tool further classified components into phloroglucinol subclasses. NMR fingerprinting HMBC data obtained for six eucalypt flower extracts identified three subclasses of pyrano-acyl-formyl phloroglucinols from Eucalyptus gittinsii subsp. gittinsii. New, eucalteretial F and (+)-eucalteretial B, and known, (-)-euglobal VII and eucalrobusone C, compounds, each belonging to predicted subclasses, were isolated and characterized. Staphylococcus aureus and Plasmodium falciparum screening revealed eucalrobusone C as the most potent antiplasmodial formyl phloroglucinol to date.

Chemodiversity and α-Glucosidase Activity of Eucalyptus Species from Northwestern Himalaya, India.

The aim of current work was to determine essential oils (EOs) composition from three Eucalyptus species, including E. citriodora, E. camaldulensis and E. globulus and assess their α-glucosidase inhibitory activity. The EOs were collected using the hydrodistillation technique and characterized by GC/MS, GC-FID and NMR. The isolated EOs from leaves parts of Eucalyptus species varied from 0.56 to 1.0 % on fresh weight basis. The content of the EOs was distinct according to the species. The most abundant metabolites were identified as citronellal (0-83.0 %), 1,8-cineole (0.2-44.8 %), spathulenol (0.4-16.1 %) α-pinene (0.4-15.9 %), p-cymene (3.7-11.9 %), citronellol (0-8.6 %), ß-eudesmol (5.3-8.6 %) and ß-pinene (0-7.1 %). The EOs obtained from targeted samples exhibited strong α-glucosidase inhibitory activity. These results are encouraging and underline that the EOs of Eucalyptus species may be a promising alternative source of natural antidiabetic.

Production and Characterization of Cellulose Nanocrystals from Eucalyptus Dissolving Pulp Using Endoglucanases from Myceliophthora thermophila.

Endoglucanase (EG) is a key enzyme during enzymatic preparation of cellulose nanocrystals (CNCs). Myceliophthora thermophila is a thermophilic fungus that has thermal properties and a high secretion of endoglucanases (EGs), and could serve as potential sources of EGs for the preparation of CNCs. In this work, four different GH families (GH5, GH7, GH12, and GH45) of EGs from M. thermophila were expressed and purified, and their enzymatic characteristics and feasibility of application in CNC preparation were investigated. It was shown that the MtEG5A from M. thermophila has good potential in the enzymatic preparation of CNCs using eucalyptus dissolving pulp as feedstock. It was also observed that there was a synergistic effect between the MtEG5A and other MtEGs in the preparation of CNCs, which improved the yield and properties of CNCs obtained by enzymatic hydrolysis. This study provides a reference for understanding the enzymatic characteristics of different families of EGs from M. thermophile and their potential application in nanocellulose production.

Exploiting the Integrated Valorization of Eucalyptus globulus Leaves: Chemical Composition and Biological Potential of the Lipophilic Fraction before and after Hydrodistillation.

E. globulus leaves have been mainly exploited for essential oil recovery or for energy generation in industrial pulp mills, neglecting the abundance of valuable families of extractives, namely, triterpenic acids, that might open new ways for the integrated valorization of this biomass. Therefore, this study highlights the lipophilic characterization of E. globulus leaves before and after hydrodistillation, aiming at the integrated valorization of both essential oils and triterpenic acids. The lipophilic composition of E. globulus leaves after hydrodistillation is reported for the first time. Extracts were obtained by dichloromethane Soxhlet extraction and analyzed by gas chromatography-mass spectrometry. In addition, their cytotoxicity on different cell lines representative of the innate immune system, skin, liver, and intestine were evaluated. Triterpenic acids, such as betulonic, oleanolic, betulinic and ursolic acids, were found to be the main components of these lipophilic extracts, ranging from 30.63-37.14 g kg-1 of dry weight (dw), and representing 87.7-89.0% w/w of the total content of the identified compounds. In particular, ursolic acid was the major constituent of all extracts, representing 46.8-50.7% w/w of the total content of the identified compounds. Other constituents, such as fatty acids, long-chain aliphatic alcohols and ß-sitosterol were also found in smaller amounts in the studied extracts. This study also demonstrates that the hydrodistillation process does not affect the recovery of compounds of greatest interest, namely, triterpenic acids. Therefore, the results establish that this biomass residue can be considered as a promising source of value-added bioactive compounds, opening new strategies for upgrading pulp industry residues within an integrated biorefinery context.

Comparison of Chemical Compositions and Antioxidant Activity of Essential Oils from Litsea Cubeba, Cinnamon, Anise, and Eucalyptus.

The purpose of this study was to compare the antioxidant activity of litsea cubeba oil (LCO), cinnamon oil (CO), anise oil (AO), and eucalyptus oil (EUC) in vitro. The chemical compositions of the essential oils (EOs) were analyzed using gas chromatography-mass spectrometry (GC-MS). The antioxidant activity of the four EOs was evaluated through scavenging DPPH free radicals, chelating Fe2+, scavenging hydroxyl free radicals, and inhibiting yolk lipid peroxidation. The results showed that the major compounds found in LCO, CO, AO, and EUC are citral (64.29%), cinnamaldehyde (84.25%), anethole (78.51%), and 1,8-cineole (81.78%), respectively. The four EOs all had certain antioxidant activity. The ability to scavenge DPPH radical was ranked in the order of LCO > CO > AO > EUC. The hydroxyl radical scavenging ability was ranked in the order of EUC > CO > LCO > AO. The chelating Fe2+ capacity was ranked in the order of EUC > AO > CO > LCO. The yolk lipid peroxidation inhibition ability was ranked in the order of CO > AO > EUC > LCO. In different antioxidant activity assays, the antioxidant activity of the EOs was different. It was speculated that the total antioxidant activity of an EO may be the result of the joint action of different antioxidant capacities.

Comparative Bioactivity Evaluation of Chemically Characterized Essential Oils Obtained from Different Aerial Parts of Eucalyptus gunnii Hook. f. (Myrtaceae).

Essential oils (EOs) obtained by hydro-distillation from different parts of twigs (EOT), leaves (EOL), and fruits (EOF) of Eucalyptus gunnii Hook. f. were screened for their chemical composition, insecticidal, repellence, and antibacterial properties. Based on GC and GC/MS analysis, 23 constituents were identified across the twigs, leaves, and fruits, with 23, 23, and 21 components, respectively. The primary significant class was oxygenated monoterpenes (82.2-95.5%). The main components were 1,8-cineole (65.6-86.1%), α-terpinyl acetate (2.5-7.6%), o-cymene (3.3-7.5%), and α-terpineol (3.3-3.5%). All three EOs exhibited moderate antibacterial activities. EOL was found to have higher antibacterial activity against all tested strains except Dickeya solani (CFBP 8199), for which EOT showed more potency. Globally, Dickeya solani (CFBP 8199) was the most sensitive (MIC ≤ 2 mg/mL), while the most resistant bacteria were Dickeya dadantii (CFBP 3855) and Pectobacterium carotovorum subsp. carotovorum (CFBP 5387). Fumigant, contact toxicity, and repellent bioassays showed different potential depending on plant extracts, particularly EOT and EOL as moderate repellents and EOT as a medium toxicant.

Effects of Melaleuca alternifolia Chell (Tea Tree) and Eucalyptus globulus Labill. Essential Oils on Antibiotic-Resistant Bacterial Biofilms.

In the present investigation, the anti-biofilm potential of two essential oils (EOs), Melaleuca alternifolia Chell (Tea-Tree) (TTO) and Eucalyptus globulus Labill. (EEO) was characterized and tested "in vitro" against both mature biofilms and biofilms in the process of formation, produced by strains belonging to three main categories of antibiotic resistant bacteria (ARB): Vancomycin-resistant enterococci (VRE), methicillin-resistant Staphylococcus aureus (MRSA) and broad-spectrum ß-lactamase-producing Escherichia coli (ESBL). The study was carried out in 96-well microtiter-plates using EOs alone, in association with each other and in combination with antibiotics against both single and multi-species biofilm. The study demonstrated the ability of TTO and EEO to counteract the ARB strains in sessile form, with promising results in particular against the biofilm in formation. Mature biofilm by ESBL E. coli was the most sensitive in the results from the quantification study of viable cells performed in multi-species biofilms. Lastly, in all tests, carried out using TTO/EEO associations and EOs/antibiotic combinations, the synergistic effect which emerged from the FIC-index has been confirmed, and both the reduction of biofilm in formation, and the removal of mature structure was obtained at very low concentrations, with values from 4 to >512-fold lower than the minimum inhibitory concentration (MIC) of the single compounds.

Chemical Composition, Antioxidant and Antibacterial Activities and Acute Toxicity of Cedrus atlantica, Chenopodium ambrosioides and Eucalyptus camaldulensis Essential Oils.

The essential oils yield of Cedrus atlantica, Chenopodium ambrosioides and Eucalyptus camaldulensis was different. C. ambrosioides gave a relatively higher yield (2.1 ± 0.1%), while that of C. atlantica was low (1.0 ± 0.1%) and that of E. camaldulensis was lower (0.75 ± 0.1% of dry matter). The active ingredients of the essential oils and some of their biological effects were also determined. The characterization of their chemical compositions showed that the three essences have different chemical profiles: C. atlantica was richer in sesquiterpenes (ß-Himachalene (54.21%) and γ -Himachalene (15.54%)), C. ambrosioides was very rich in monoterpene peroxides and monoterpenes (α-Terpinene (53.4%), ascaridole (17.7%) and ρ-Cymene (12.1%)) and E. camaldulensis was very rich in monoterpene compounds and monoterpenols (p-cymene (35.11%), γ-Eudesmol (11.9%), L-linalool (11.51%) and piperitone (10.28%)). The in vitro measurement of antioxidant activity by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) reduction assay showed a significant performance of the eucalyptus oil and average performance of the other two (C. atlantica and C. ambrosioides). The in vitro bio-test for their antimicrobial effects showed that the antibacterial activity differed depending on the essential oil and the concentration used, and that their bactericidal efficacy was similar or superior to that of synthetic antibiotics. The toxicity test on rats revealed that the LD50 of the three essential oils was 500 mg/kg body weight, which classifies them as category four cytotoxic natural products at high doses.

Chemical Composition, Antibacterial Properties, and Anti-Enzymatic Effects of Eucalyptus Essential Oils Sourced from Tunisia.

This study was conducted to examine the chemical composition of the essential oils (EOs) from six Tunisian Eucalyptus species and to evaluate their anti-enzymatic and antibiofilm activities. The EOs were obtained through hydro-distillation of dried leaves and subsequently analyzed using GC/MS. The main class of compounds was constituted by oxygenated monoterpenes, particularly prominent in E. brevifolia (75.7%), E. lehmannii (72.8%), and E. woollsiana (67%). Anti-enzymatic activities against cholinesterases, α-amylase, and α-glucosidase were evaluated using spectrophotometric methods. Notably, the E. brevifolia, E. extensa, E. leptophylla, E. patellaris, and E. woollsiana EOs displayed potent acetylcholinesterase (AChE) inhibition (IC50: 0.25-0.60 mg/mL), with E. lehmannii exhibiting lower activity (IC50: 1.2 mg/mL). E. leptophylla and E. brevifolia showed remarkable α-amylase inhibition (IC50: 0.88 mg/mL), while E. brevifolia and E. leptophylla significantly hindered α-glucosidase (IC50 < 30 mg/mL), distinguishing them from other EOs with limited effects. Additionally, the EOs were assessed for their anti-biofilm properties of Gram-positive (Staphylococcus aureus and Listeria monocytogenes) and Gram-negative (Acinetobacter baumannii, Pseudomonas aeruginosa and Escherichia coli) bacterial strains. The E. extensa EO demonstrated the main antibiofilm effect against E. coli and L. monocytogenes with an inhibition > 80% at 10 mg/mL. These findings could represent a basis for possible further use of Eucalyptus EOs in the treatment of human microbial infections and/or as a coadjutant in preventing and treating Alzheimer's disease and/or diabetes mellitus.

Anti-inflammatory mechanisms of eucalyptol rich Eucalyptus globulus essential oil alone and in combination with flurbiprofen.

Inflammation is the core contributor in the pathogenesis of various acute and chronic illness including appendicitis, bronchitis, arthritis, cancer and neurological diseases. NSAIDs, commonly used medications for inflammatory diseases, on prolonged use cause GI bleeding, ulcers and many more issues. Plant-based therapeutic agents including essential oils in combination with low-dose synthetic drugs have been shown to produce synergistic effects and reduce complications of synthetic drugs. This study was designed to evaluate the anti-inflammatory, analgesic and anti-pyretic properties of Eucalyptus globulus essential oil alone and in combination with flurbiprofen. GC-MS analysis was performed to screen chemical composition of oil. In vitro anti-inflammatory assay (membrane stabilization assay) and in vivo inflammatory acute (carrageenan and histamine-induced paw oedema) and chronic (cotton pellet-induced granuloma and Complete Freund's adjuvant-induced arthritis) models were performed to check anti-inflammatory properties. Acetic acid-induced algesia and yeast-induced pyrexia models were performed to check analgesic and anti-pyretic properties. qRT-PCR was performed to study the effect of treatments on the expression of inflammatory biomarkers. GC-MS analysis of E. globulus essential oil showed the presence of eucalyptol along with other active biomolecules. 500 + 10 mg/kg of oil-drug combination showed significantly (p < 0.05) better in vitro membrane stabilization effects as compared with groups treated with 500 mg/kg of E. globulus oil and 10 mg/kg of Flurbiprofen alone. 500 + 10 mg/kg of oil-drug combination showed significantly (p < 0.05) better anti-inflammatory, analgesic and antipyretic effects as compared to 500 mg/kg of E. globulus oil alone in all in vivo models. When comparison was done between 500 + 10 mg/kg of oil-drug combination-treated and 10 mg/kg Flurbiprofen-treated group, the former group showed significantly (p < 0.05) better anti-inflammatory and anti-pyretic effects, but there were non-significant differences in the analgesic model. Animal group treated with 10 mg/kg of Flurbiprofen showed significantly (p < 0.05) better anti-inflammatory and analgesic effects than group treated with 500 mg/kg of oil alone while, there were non-significant differences in anti-pyretic effects. qRT-PCR analysis showed significant (p < 0.05) down-regulation in the expression of IL-4 and TNF-α in serum samples of animals treated with 500 + 10 mg/kg of oil-drug combination as compared to the diseased control (arthritic) group. Overall, the current research demonstrates that Eucalyptus globulus essential oil in combination with flurbiprofen showed better anti-inflammatory, analgesic and anti-pyretic effects than oil and flurbiprofen alone which is attributed to the down-regulation of pro-inflammatory biomarkers (IL-4 and TNF-α). Further studies are required to formulate a stable dosage form and to check the anti-inflammatory efficacy in different inflammatory disorders.

Mass spectrometry-based forest tree metabolomics.

Research in forest tree species has advanced slowly when compared with other agricultural crops and model organisms, mainly due to the long-life cycles, large genome sizes, and lack of genomic tools. Additionally, trees are complex matrices, and the presence of interferents (e.g., oleoresins and cellulose) challenges the analysis of tree tissues with mass spectrometry (MS)-based analytical platforms. In this review, advances in MS-based forest tree metabolomics are discussed. Given their economic and ecological significance, particular focus is given to Pinus, Quercus, and Eucalyptus forest tree species to better understand their metabolite responses to abiotic and biotic stresses in the current climate change scenario. Furthermore, MS-based metabolomics technologies produce large and complex datasets that require expertize to adequately manage, process, analyze, and store the data in dedicated repositories. To ensure that the full potential of forest tree metabolomics data are translated into new knowledge, these data should comply with the FAIR principles (i.e., Findable, Accessible, Interoperable, and Re-usable). It is essential that adequate standards are implemented to annotate metadata from forest tree metabolomics studies as is already required by many science and governmental agencies and some major scientific publishers. © 2019 John Wiley & Sons Ltd. Mass Spec Rev 40:126-157, 2021.

Eucarbwenstols A-H, eight novel compounds from Eucalyptus robusta prevents MPC-5 injury via ROS modulation and regulation of mitochondrial membrane potential.

BACKGROUND: The damage of podocytes is a primary hallmark of lupus nephritis (LN). Therefore, finding an effective way to inhibit the podocyte injury is important for improving the survival and development of patients with LN. Eucalyptus robusta exhibits anti-inflammatory properties. However, whether Formyl phloroglucinol meroterpenoids (FPMs), which are specialized metabolites of the genus Eucalyptus, is an anti-inflammatory active ingredient of E. robusta remains to be determined. PURPOSE: This study asimed to identify novel FPMs from E. robusta and investigated their anti-inflammatory effects. METHODS: Various separation methods were used to isolate and identify the compounds in the PE extract of E. robusta. The structures of the isolates were determined using 1D/2D NMR data and electron circular dichroism (ECD) calculations. The level of mitochondrial reactive oxygen species (ROS) level and mitochondrial membrane potential (MMP) of the podocyte cell line, MPC-5, were assessed using a multifunctional microplate reader combined with flow cytometry and fluorescence microscopy. RESULTS: Eight novel FPMs (1-8, Eucarbwenstols A-H, Fig. 1) and 15 known FPMs (9-23) were purified from the PE extract of E. robusta. It is noteworthy that compound 1 possesses an unprecedented FPM carbon skeleton. Among these compounds, compounds 1, 2, 4 and 5 showed the most promising potential for protecting MPC-5 cells because pretreatment with pro-inflammatory cytokines TGF-ß, IFN-α and IL-6 decreased ROS production and ameliorated the mitochondrial state. CONCLUSIONS: Our research contributes to the characterization of E. robusta constituents and highlights the anti-inflammatory effects of FPMs.