HR-LC-ESI-Orbitrap-MS-Based Metabolic Profiling Coupled with Chemometrics for the Discrimination of Different Echinops spinosus Organs and Evaluation of Their Antioxidant Activity.

This study aimed to assess and correlate the phenolic content and the antioxidant activity of the methanol extracts of the stems, roots, flowers, and leaves of Echinops spinosus L. from north-eastern Algeria. Qualitative analysis was performed by high-resolution mass spectrometry (HR) LC-ESI-Orbitrap-MS and (HR) LC-ESI-Orbitrap-MS/MS). Forty-five compounds were identified in the methanol extracts; some are described for the first time in E. spinosus. Targeted phenolic compounds were quantified by HPLC-DAD and it was shown that caffeoyl quinic derivatives were the most abundant compounds. Chemometric analysis was performed using principal component analysis (PCA) and hierarchical cluster analysis (HCA) based on the qualitative and quantitative LC data. The score plot discriminates different Echinopsis spinosus organs into three distinct clusters, with the stems and flowers allocated in the same cluster, reflecting their resemblance in their secondary metabolites. The antioxidant activities of the methanol extracts were assessed using cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant assay (FRAP), diphenyl picryl hydrazyl radical-scavenging capacity assay (DPPH●), and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS●+). The root extract exhibited the highest antioxidant activity, evidenced by 3.26 and 1.61 mmol Fe2+/g dried residue for CUPRAC and FRAP, respectively, and great free radical-scavenging activities estimated by 0.53 and 0.82 mmol TEAC/g dried residue for DPPH● and ABTS●+, respectively. The methanol extract of the roots demonstrated a significant level of total phenolics (TP: 125.16 mg GAE/g dried residue) and flavonoids (TFI: 25.40 QE/g dried residue TFII: 140 CE/g dried residue). Molecular docking revealed that tricaffeoyl-altraric acid and dicaffeoyl-altraric acid exhibited the best fit within the active sites of NADPH oxidase (NO) and myeloperoxidase (MP). From ADME/TOPAKT analyses, it can be concluded that tricaffeoyl-altraric acid and dicaffeoyl-altraric acid also revealed reasonable pharmacokinetic and pharmacodynamic characteristics with a significant safety profile.

Evidence for the anti-inflammatory activity of Bupleurum marginatum (Apiaceae) extracts using in vitro and in vivo experiments supported by virtual screening.

OBJECTIVES: To explore the potential anti-inflammatory activity of Bupleurum marginatum extracts using in vitro and in vivo studies supported by virtual screening. METHODS: Antioxidant activity was assessed using the DPPH˙ and inhibition of 2-deoxyribose degradation assays. Anti-inflammatory activity was determined in vitro by measuring the suppression of prostaglandin E2 release (PGE2 ) in pancreatic cancer cells (MIA-PaCa-2) and the inhibition of 5-lipoxygenase whereas the rat paw oedema was used in vivo. The major constituents were docked in 5-lipoxygenase and cyclooxygenase-II active sites. KEY FINDINGS: Methanol and dichloromethane (DCM) extracts showed IC50 of 46.99 and 162.99 µg/ml in the DPPH˙, 1.52 and 2.12 µg/ml in inhibition of 2-deoxyribose degradation assays, respectively. They reduced PGE2 release by 41.33 and 52.85% at 25 µg/ml and inhibited 5-lipoxygenase with IC50 of 45.28 and 25.92 µg/ml, respectively. 50 and 70% reduction in the diameter of the carrageenan-induced rat paws with methanol and DCM extracts, respectively, with a marked decline in the inflammation score was observed. Rutin, a predominating compound, showed a strong interaction with the key amino acids in 5-LOX active site with interaction energy of -74.59 kcal/mol. CONCLUSIONS: Our study provides evidence for an interesting anti-inflammatory activity of B. marginatum aerial parts offering a natural anti-inflammatory agent.

Application of chemometrics in quality control of Turmeric (Curcuma longa) based on Ultra-violet, Fourier transform-infrared and 1H NMR spectroscopy.

Turmeric (Curcuma longa L.) belongs to the family Zingiberaceae that is widely used as a spice in food preparations in addition to its biological activities. UV, FT-IR, 1H NMR in addition to HPLC were applied to construct a metabolic fingerprint for Turmeric in an attempt to assess its quality. 30 samples were analyzed, and then principal component analysis (PCA) and hierarchical clustering analysis (HCA) were utilized to assess the differences and similarities between collected samples. PCA score plot based on both HPLC and UV spectroscopy showed the same discriminatory pattern, where the samples were segregated into four main groups depending on their total curcuminoids content. The results revealed that UV could be utilized as a simple and rapid alternative for HPLC. However, FT-IR failed to discriminate between the same species. By applying 1H NMR, the metabolic variability between samples was more evident in the essential oils/fatty acid region.

The Genus Myrtus L. in Algeria: Composition and Biological Aspects of Essential Oils from M. communis and M. nivellei: A Review.

The genus Myrtus L. (Myrtaceae family) comprises two species, Myrtus communis L. (known as common myrtle) growing wild all around the Mediterranean basin and Myrtus nivellei Batt. and Trab. (known as Saharan myrtle), found in central Sahara. Only one country, Algeria, hosts both species, M. communis in the North and M. nivellei in the South. The aim of this review was to collect, summarize, and compare the main results reported relative to the essential oils isolated from aerial parts of both species: botanical aspects, habitat, traditional use, chemical composition, new compounds, antimicrobial activity, antioxidant activity, anti-inflammatory effect, and insecticidal activity. Both essential oils have potential applications in human health.

Myrtus communis L. as source of a bioactive and safe essential oil.

In Algeria, Myrtus communis L. is distributed throughout the Tell Atlas and the coastal regions of Algiers and Constantine. The leaves are used in respiratory disorders, diarrhea and hemorrhoids. The aims of this work were to evaluate the antifungal and anti-inflammatory potential of well characterized essential oils (EO). Since EO can be applied by inhalation, dermal application and oral administration, we used several mammalian cell lines to assess safe bioactive doses. The chemical composition of two samples was investigated by GC-FID, GC-MS and (13)C NMR spectroscopy. Monoterpene derivatives are the main compounds: α-pinene (50.8 and 33.6%), 1,8-cineole (21.9 and 13.3%), linalool (2.7 and 14.8%), and linalyl acetate (0.5 and 9.5%). The antifungal evaluation revealed that the oils were more active against Cryptococcus neoformans (yeast) and Epidermophyton floccosum, Microsporum canis, Trichophyton rubrum (dermatophytes). The anti-inflammatory potential was evaluated using an in vitro model of lipopolysaccharide (LPS)-stimulated macrophages. Assessment of cell viability was made through the MTT assay. Both oils were able to significantly inhibit NO production, without affecting cell viability, in concentrations up to 0.64 mg/mL. These promising results, disclose bioactive concentrations of Myrtle essential oils with a safety profile suggesting a potential oral and topical application or use by inhalation.

Composition and chemical variability of Eucalyptus bosistoana essential oil from Algerian Sahara.

The composition of eight oil samples isolated from leaves of Eucalyptus bosistoana F. Muell., acclimatized in Tamanrasset (southern Algeria, Saharan climate), has been investigated by GC (retention indices), GC-MS and 13C NMR spectroscopy. T wo groups may be distinguished. The five samples of group I have their composition dominated by p-cymene (32.0-39.5%), cryptone (11.5-15.6%), 1,8-cineole (7.8-10.5%) and spathulenol (6.8-16.5%). The three oil samples of group II contained mainly 1,8-cineole (55.3-63.9%) and alpha-pinene (11.6-12.1%).

New compounds, chemical composition, antifungal activity and cytotoxicity of the essential oil from Myrtus nivellei Batt. & Trab., an endemic species of Central Sahara.

ETHNOPHARMACOLOGIC RELEVANCE: Myrtus nivellei Batt. & Trab. (Myrtaceae) known as Sahara myrtle is appreciated by the Touaregs as medicinal plant. Infusion of leaves is employed against diarrhea and blennorrhea. Crushed leaves added to oil or to butter ointment have been traditionally used for the treatment of dermatosis. Aim of the study is to consider the traditional medicinal uses and the lack of scientific studies on their biological activities, the present study was designed to elucidate the chemical composition, the antifungal activity of its essential oils against fungi responsible for human infections, as well as, its cytotoxicity in the mammalian keratinocytes. MATERIALS AND METHODS: Chemical analysis of Myrtus nivellei essential oil isolated by hydrodistillation of aerial parts (leaves and flowers), was carried out using a combination of chromatographic (CC, GC with retention indices) and spectroscopic techniques (MS, (13)C NMR, 2D NMR). The antifungal activity was evaluated by using broth macrodilution methods for yeasts and filamentous fungi. Cytotoxicity was tested in HaCaT keratinocytes through the MTT assay. RESULTS: Ten samples coming from two localities of harvest were investigated. The chemical composition was largely dominated by 1,8-cineole (33.6-50.4%) and limonene (17.5-25.0%). The structure of two new compounds bearing the isoamylcyclopentane skeleton has been elucidated. The oil was more active against Cryptococcus neoformans with MIC of 0.16µL/mL followed by dermatophytes, with MICs of 0.64 and 1.25µL/mL. Furthermore, evaluation of cell viability showed no cytotoxicity in HaCaT keratinocytes at concentrations up to 1.25µL/mL. CONCLUSIONS: The composition of Myrtus nivellei oil differed from that of Myrtus communis. The structure of two di-nor-sesquiterpenoids has been elucidated. It was possible to find appropriate doses of Myrtus nivellei oil with both antifungal activity and very low detrimental effect on keratinocytes. These findings add significant information to the pharmacological activity of Myrtus nivellei essential oils, specifically to its antifungal properties, thus justifying and reinforcing the use of this plant in traditional medicine.

Chemical variability of Algerian Myrtus communis L.

The composition of 55 samples of essential oil isolated from the aerial parts of wild growing Myrtus communis L. harvested in 16 locations from East to West Algeria were investigated by GC (determination of retention indices) and (13) C-NMR analyses. The essential oils consisted mainly of monoterpenes, α-pinene (27.4-59.2%) and 1,8-cineole (6.1-34.3%) being the major components. They were also characterized by the absence of myrtenyl acetate. The compositions of the 55 oils were submitted to k-means partitioning and principal component analysis, which allowed the distinction of two groups within the oil samples, which could be subdivided into two subgroups each. Groups I (78% of the samples) and II were differentiated on the basis of the contents of α-pinene, linalool, and linalyl acetate. Subgroups IA and IB could be distinguished by their contents of α-pinene and 1,8-cineole. Subgroups IIA and IIB differed substantially in their contents of 1,8-cineole and limonene. All the samples contained 3,3,5,5,8,8-hexamethyl-7-oxabicyclo[4.3.0]non-1(6)-ene-2,4-dione (up to 4.9%).

Composition and chemical variability of leaf oil of Myrtus communis from north-eastern Algeria.

The chemical composition of 27 oil samples of Myrtus communis isolated from leaves collected in three locations in north-eastern Algeria was investigated by GC(RI) and 13C NMR spectroscopy. Yields ranged between 0.2-1.2% (w/w). The chemical composition of the oils was largely dominated by monoterpene hydrocarbons, with alpha-pinene (40.5-64.0%), 1,8-cineole (10.9-29.1%) and limonene (6.7-8.2%) being the major compounds. In all the samples, 3,3,5,5,8,8-hexamethyl-7-oxabicyclo[4.3.0]non-1(6)-ene-2,4-dione was identified (0.8-1.5%). The composition is similar to that reported for myrtle oils from Corsica, Sardinia and Tunisia, but differed from that of Moroccan and Spanish myrtle oils.