RESUMO
Phytochemical study on the 95% ethyl alcohol extract of stems of Chenopodium ambrosioides resulted in the isolation of two new polyol monoterpenes, 4-hydroxy-4(α or ß)-isopropyl-2-methyl-2-cyclohexen-1-one (1) and 1-methyl-4ß- isopropyl-1-cyclohexene-4α,5α,6α-triol (2), together with five known compounds, (1S,2S,3R,4S)-1-methyl-4-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (3), (1R,2S,3S,4S)- 1,2,3,4-tetrahydroxy-p-menthane (4), (1R,2S)-3-p-menthen-1,2-diol (5), (1R,4S)-p- menth-2-en-1-ol (6) and 1,4-dihydroxy-p-menth-2-ene (7). The structures of the new compounds were established on the basis of detailed spectroscopic evidence including extensive 1D and 2D NMR techniques. Compounds 1-7 were evaluated for their anti-inflammatory activity, and compound 1 showed moderate ability to inhibit NO production of LPS-stimulated RAW 264.7 macrophages with an IC50 value of 16.83 µM.
Assuntos
Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Chenopodium ambrosioides/química , Monoterpenos/isolamento & purificação , Animais , Anti-Inflamatórios não Esteroides/isolamento & purificação , Linhagem Celular , Avaliação Pré-Clínica de Medicamentos/métodos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/farmacologia , Caules de Planta/química , Polímeros/químicaRESUMO
Five new diterpenoids (1-5) were isolated from the roots of Aralia melanocarpa, together with four known compounds, 7ß-hydroxy-ent-pimara-8(14),15-diene-19-oic acid (6), 18-norpimara-8(14),15-dien-4-ol (7), ent-16ßH,17-isovalerate-kauran-19-oic acid (8), and ent-16α,17-dihydroxykauran-19-oic acid (9). Based on the MS, IR, and NMR spectral analysis, the structures of the five new diterpenoids (1-5) were elucidated. The cytotoxic activities of compounds 1-9 were assayed, and compounds 1 and 2 showed cytotoxicity in four cancer cell lines with IC50s from 4.2 to 8.2 µM.
