RESUMO
Volatiles metabolites from the liverwort Plagiochila porelloides harvested in Corsica were investigated by chromatographic and spectroscopic methods. In addition to already reported constituents, three new compounds were isolated by preparative chromatography and their structures were elucidated by mass spectrometry (MS) and NMR experiments. Hence, an atypic aliphatic compound, named 1,2-dihydro-4,5-dehydronerolidol and two isomers, (E) and (Z), possessing an unusual humbertiane skeleton (called p-menth-1-en-3-[2-methylbut-1-enyl]-8-ol) are newly reported and fully characterized in this work. The in vitro antiprotozoal activity of essential oil and extract of P. porelloides against Trypanosoma brucei brucei and Leishmania mexicana mexicana and cytotoxicity were determined. Essential oil and Et2O extract showed a moderate activity against T. brucei with IC50 values: 2.03 and 5.18 µg/mL, respectively. It is noteworthy that only the essential oil showed a high selectivity (SI = 11.7). Diethyl oxide extract exhibited moderate anticancer (cancerous macrophage-like murine cells) activity and also cytotoxicity (human normal fibroblast) with IC50 values: 1.25 and 2.96 µg/mL, respectively.
Assuntos
Antiprotozoários , Hepatófitas , Óleos Voláteis , Trypanosoma brucei brucei , Animais , Camundongos , Humanos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antiprotozoários/farmacologia , Antiprotozoários/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Plasmodium falciparumRESUMO
The chemical composition of essential oils extracted from aerial parts of Eryngium campestre collected in 37 localities from Western Algeria was characterized using GC-FID and GC/MS analyses. Altogether, 52 components, which accounted for 70.1 to 86.8% of the total composition oils were identified. The main compounds were Germacrene D (0.4-53.4%), Campestrolide (1.6-35.3%), Germacrene B (0.2-21.5%), Myrcene (0.1-8.4%), α-Cadinol (0.2-7.6%), Spathulenol (0.1-7.6%), Eudesma-4(15)-7-dien-1-ß-ol (0.1-7.6%) and τ-Cadinol (0.3-5.5%). The chemical compositions of essential oils obtained from separate organs and during the complete vegetative cycle of the plant were also studied. With the uncommon 17-membered ring lactone named Campestrolide as the main component, Algerian E. campestre essential oils exhibited a remarkable chemical composition. A study of the chemical variability using statistical analysis allowed the discrimination of two main clusters according to the geographical position of samples. The study contributes to the better understanding of the relationship between the plant and its environment. Moreover, the antimicrobial activity of the essential oil was assessed against twelve strains bacteria and two yeasts involved in foodborne and nosocomial infections using paper disc diffusion and dilution agar assays. The in vitro study demonstrated a strong activity against Gram-positive strains such as S. aureus, B. cereus, and E. faecalis. The cytotoxicity and antiparasitic activities (on Lmm and Tbb) of the collective essential oil and one sample rich in campestrolide, as well as some enriched fractions or fractions containing other terpenic compounds, were also analyzed. Campestrolide seems to be one compound responsible for the cytotoxic and antileishmanial effect, while myrcene or/and trans-ß-farnesene have a more selective antitrypanosomal activity.
Assuntos
Anti-Infecciosos/química , Eryngium/química , Óleos Voláteis/química , Argélia , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , Análise por Conglomerados , Infecção Hospitalar/tratamento farmacológico , Doenças Transmitidas por Alimentos/tratamento farmacológico , Fungos/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Óleos Voláteis/farmacologia , Componentes Aéreos da Planta/química , Óleos de Plantas/química , Óleos de Plantas/farmacologiaRESUMO
The chemical composition of a hexanic extract of Eryngium campestre, obtained from its aerial parts, was investigated by GC-FID, GC/MS, HRMS, NMR and VCD analyses. The main compounds were germacrene D (23.6%), eudesma-4(15)-7-dien-1-ß-ol (8.2%) and falcarindiol (9.4%), which are associated with a new uncommon and naturally found 17-membered ring lactone. This 17-membered ring features conjugated acetylenic bonds, named campestrolide (23.0%). The crude extract showed moderate antitrypanosomal (Trypanosoma brucei brucei), antileishmanial (Leishmania mexicana mexicana) and anticancer (cancerous macrophage-like murine cells) activities, and also displayed cytotoxicity, (human normal fibroblasts) in similar concentration ranges (IC50 = 3.0, 3.9, 4.0 and 4.4 µg/mL respectively). Likewise, campestrolide displayed low activity on all tested cells (IC50: 12.5â»19.5 µM) except on Trypanosoma, on which it was very active and moderately selective (IC50 = 2.2 µM. SI= 8.9). In conclusion, the new compound that has been described, displaying a singular structure, possesses interesting antitrypanosomal activity that should be further investigated and improved.
Assuntos
Eryngium/química , Lactonas/química , Lactonas/farmacologia , Animais , Antiprotozoários/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Morte Celular/efeitos dos fármacos , Linhagem Celular , Humanos , Concentração Inibidora 50 , Leishmania/efeitos dos fármacos , Espectrometria de Massas , Camundongos , Extratos Vegetais/química , Tripanossomicidas/farmacologiaRESUMO
Cytological analysis of thyroid nodules detected using ultrasound-guided fine-needle aspiration technique is an efficient method for the diagnosis of well-differenciated tumors such as papillary thyroid carcinoma. However, for between 10 to 30% of all the nodules, the cytological analysis based on fine-needle aspiration biopsies leads to an "indeterminated" identification. Consequently, a surgical excision is then necessary for a definite histological diagnosis of the lesions, resulting in 85% of the patient with indeterminated nodules undergoing unnecessary surgery since their tumor is finally diagnosed as benign. In this work, we discuss how HRMAS (1)H NMR-based metabolomics could be a complementary tool for the diagnosis of these elusive cases. We first showed that our approach was able to discriminate clearly any types of thyroid lesions from healthy tissues. Then we proceeded to demonstrate that the information produced by (1)H HRMAS NMR spectra differentiate tumors according to their malignancy grade, even when they belong to the "indeterminate" category. Analysis of the discriminating spectral area in this last case points out toward a possible increase of phenylalanine, taurine, and lactate and a decrease of choline and choline derivatives, myo- and scyllo-inositol in the malignant tumors compared to the benign ones.