RESUMO
One new and five known sesquiterpene coumarins were isolated from the roots of Ferula pseudalliacea. The structures were elucidated by 1D and 2D NMR, and HR-ESIMS data as 4'-hydroxy kamolonol acetate (1), kamolonol (2), szowitsiacoumarin A (3), farnesiferon B (4), farnesiferol C (5), and flabellilobin A (6). The absolute configuration of compounds 1, 2, and 4 was established by comparison of experimental and simulated electronic circular dichroism spectra using time dependence density function theory. 4'-Hydroxy kamolonol acetate and kamolonol showed antibacterial activity against Heliobacter pylori and Staphylococcus aureus at a concentration of 64 µg/mL. Kamolonol, 4'-hydroxy kamolonol acetate, and farnesiferon B displayed a cytotoxic activity in HeLa cells, with an IC50 of 3.8, 4.5, and 7.7 µM, respectively.
Assuntos
Antibacterianos/farmacologia , Cumarínicos/farmacologia , Ferula/química , Sesquiterpenos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Cumarínicos/química , Cumarínicos/isolamento & purificação , Células HeLa , Helicobacter pylori/efeitos dos fármacos , Humanos , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Ressonância Magnética Nuclear Biomolecular , Extratos Vegetais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacosRESUMO
Dried leaves of Satureja khuzestanica Jamzad are a popular herbal medicine and dental anesthetic among the nomadic inhabitants of southwestern Iran. The present study establishes criteria for identification of S. khuzestanica dried whole, fragmented and powdered leaves for specification as a herbal substance using macroscopic and microscopic characterization. Quantitative microscopy techniques were also considered. Macroscopically leaves exhibit a grayish-green color, are broadly ovate in shape with an acute apex, attenuate base, and ciliate margin and have a surface covered by an indumentum of glandular and non-glandular trichomes. Microscopically leaves have an isobilateral amphistomatic structure containing peltate glandular trichomes consisting of a multiseriate stalk (five cells) and an enlarged secretory head composed of 12 cells, capitate glandular trichomes of variable morphology together with two types of non-glandular trichomes. Oval-shaped hygromorphic diacytic stomata with an adaxial stomatal index of 13.54, collateral vascular bundles consisting of xylem, and three layers of sclerenchymatous tissue close to phloem together with cluster, prismatic and raphide calcium oxalate crystals were also identified as useful pharmacognostic parameters for identification of S. khuzestanica dried leaves.
Assuntos
Medicina Herbária/métodos , Folhas de Planta/anatomia & histologia , Folhas de Planta/citologia , Plantas Medicinais/anatomia & histologia , Plantas Medicinais/citologia , Satureja/anatomia & histologia , Satureja/citologia , Biometria , Irã (Geográfico) , Microscopia , Plantas Medicinais/classificação , Satureja/classificaçãoRESUMO
The first disesquiterpene coumarin, sanandajin, five sesquiterpene coumarins, kamolonol acetate, fekrynol acetate, ethyl galbanate, methyl galbanate, farnesiferol B, and a sesquiterpene, aristolone, were isolated from a n-hexane extract of Ferula pseudalliacea roots. The structures were elucidated by 1D and 2D NMR, HR-ESIMS data, and kamolonol acetate was confirmed by single-crystal X-ray analysis. The absolute configuration of compounds was established by comparison of experimental and simulated ECD spectra using time dependence density function theory (TDDFT). In vitro antiplasmodial activity against Plasmodium falciparum K1 strain was determined. sanandajin, kamolonol acetate and methyl galbanate showed moderate antiplasmodial activity, with IC(50) values of 2.6, 16.1 and 7.1 µM, respectively.