RESUMO
Five Lycopodium alkaloids featuring novel C17N2 (1 and 2), C29N3 (3 and 4), and C15N2 (5) skeletons were isolated from Lycopodium japonicum. Compound 1 is the first natural product containing a 3-aza[3.3.3]propellane motif. The structures of these compounds were elucidated by spectroscopic analysis, X-ray crystallography, and computational methods. Compounds 1 and 3-5 significantly inhibited TGF-ß1-induced fibronectin deposition in HK-2 cells at a nontoxic concentration of 20 µM.
Assuntos
Alcaloides , Lycopodium , Alcaloides/química , Alcaloides/farmacologia , Cristalografia por Raios X , Fibrose , Lycopodium/química , Estrutura MolecularRESUMO
A phytochemical investigation on the whole plant of Plantago maxima Juss. ex Jacq led to the isolation of a new and rare chlorinated iridoid glycoside named plantomoside (1), along with three known compounds, geniposidic acid (2), 10-deoxygeniposidic acid (3), and viteoid II (4). The structure of 1 was determined through 1 D and 2 D NMR spectroscopic data analysis, HR-ESI-MS, and acid hydrolysis.
Assuntos
Cloro/química , Glicosídeos Iridoides/isolamento & purificação , Plantago/química , Animais , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Humanos , Glucosídeos Iridoides/química , Glucosídeos Iridoides/isolamento & purificação , Glicosídeos Iridoides/química , Glicosídeos Iridoides/farmacologia , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico/biossíntese , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7RESUMO
Lycocasuarines I-Q (1-9), nine new lycodine-type Lycopodium alkaloids were isolated from the aerial parts of Lycopodiastrum casuarinoides (Spring) Holub ex R.D.Dixit. Their structures were unambiguously determined via extensive spectroscopic analyses, including HRESIMS, NMR, and electronic circular dichroism (ECD). The new alkaloids were evaluated for their in vitro inhibitory activity against acetylcholinesterase (AChE). Compounds 3, 5-8 exhibited marginal or weak activities with IC50 values ranging from 97.2 to 171.9⯵M.
Assuntos
Alcaloides/farmacologia , Inibidores da Colinesterase/farmacologia , Lycopodiaceae/química , Alcaloides/isolamento & purificação , China , Inibidores da Colinesterase/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/químicaRESUMO
Thirteen previously undescribed lycodine-type Lycopodium alkaloids, namely, five alkaloids (lycocasuarines D-H) each possessing an uncommon five-membered C ring and eight Lycopodium alkaloid glycosides (casuarinosides A-H), together with a known analog, were isolated from the aerial parts of Lycopodiastrum casuarinoides (Spring) Holub ex R.D.Dixit (Lycopodiaceae). The structures of the compounds were elucidated by extensive spectroscopic analysis, single-crystal X-ray diffraction, and chemical methods. In addition, the acetylcholinesterase inhibitory activity of the isolated compounds was evaluated.