RESUMO
The present study describes the chemical and enantiomeric composition of a new essential oil, distilled from the dry leaves of Gynoxys buxifolia (Kunth) Cass. The chemical analysis was conducted by GC-MS and GC-FID, on two orthogonal capillary columns. A total of 72 compounds were detected and quantified with at least one column, corresponding to about 85% by weight of the whole oil mass. Of the 72 components, 70 were identified by comparing the respective linear retention indices and mass spectra with data from the literature, whereas the two main constituents were identified by preparative purification and NMR experiments. The quantitative analysis was carried out calculating the relative response factor of each compound according to their combustion enthalpy. The major constituents of the EO (≥3%) were: furanoeremophilane (31.3-28.3%), bakkenolide A (17.6-16.3%), caryophyllene oxide (6.0-5.8%), and (E)-ß-caryophyllene (4.4%). Additionally, the hydrolate was also analyzed with respect to the dissolved organic phase. About 40.7-43.4 mg/100 mL of organic compounds was detected in solution, of which p-vinylguaiacol was the main component (25.4-29.9 mg/100 mL). Finally, the enantioselective analysis of some chiral terpenes was carried out, with a capillary column based on ß-cyclodextrin chiral stationary phase. In this analysis, (1S,5S)-(-)-α-pinene, (1S,5S)-(-)-ß-pinene, (S)-(+)-α-phellandrene, (S)-(+)-ß-phellandrene, and (S)-(-)-terpinen-4-ol were detected as enantiomerically pure, whereas (S)-(-)-sabinene showed an enantiomeric excess of 69.2%. The essential oil described in the present study is a good source of two uncommon volatile compounds: furanoeremophilane and bakkenolide A. The former lacks bioactivity information and deserves further investigation, whereas the latter is a promising selective anticancer product.
RESUMO
The search for anti-infective activity in the antipyretic plant Senecio smithioides was conducted. Petroleum ether (PE), dichloromethane (CH2Cl2), ethyl acetate (EtOAc) and hydroethanolic (96% EtOH) extracts, and compounds 9-oxoeuryopsin (1), epoxydecompostin (2) and senecionine (3) were obtained from the aerial parts. All extracts and 1 were tested against chloroquine-resistant strain of Plasmodium falciparum (ref. chloroquine), Trypanosoma cruzi (ref. nifurtimox), Leishmania braziliensis, Leishmania amazonensis and Leishmania donovani (ref. pentamidine), Staphylococcus aureus and Escherichia coli (ref. gentamicin) and, Neurospora crassa and Candida albicans (ref. ketoconazole). The PE extract exhibited the strongest in vitro activity against Plasmodium falciparum IC50 < 1.0 µg/mL. 1 was established as a potent antiplasmodial compound with an IC50 = 1.2 µg/mL, 5.2 µM. Other antiparasitic activities were recorded for all extracts and 1. Antibacterial and antifungal activity was negligible.
RESUMO
Compound, 10H-9-oxofuranoeremophilane was isolated from Senecio filaginoides var. filaginoides, and its structure established on the basis of spectral analysis and and comparison with literature data. Antimicrobial activity was demonstrated against Candida spp but not against bacteria (Staphylococcus aureus, Escherichia coli and Pseudomona aeruginosa). Besides, the compound showed antifungal activity and effect on mycelial growth of the phytopathogenic fungus Botrytis cinerea. and comparison with literature data.
Un compuesto, 10H-9-oxofuranoeremofilano fue aislado de Senecio filaginoides var. filaginoides, esta estructura fue establecida sobre la base del análisis espectral y comparación con datos bibliográficos. La actividad antimicrobiana fue demostrada contra Candida spp pero no contra las bacterias (S.aureus, E.coli y P. aeruginosa). Además el compuesto mostró actividad antifúngica y efectos sobre el crecimiento micelial del hongo fitopatógeno Botrytis cinerea.