ABSTRACT
A new sesquilignan glycoside 1, together with seven known phenolic glycosides 2-8 were isolated from the aerial parts of Capsella bursa-pastoris. The chemical structure of the new compound 1 was elucidated by extensive nuclear magnetic resonance (NMR) data (¹H- and 13C-NMR, ¹H-¹H correlation spectroscopy (¹H-¹H COSY), heteronuclear single-quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), and nuclear overhauser effect spectroscopy (NOESY)) and HR-FABMS analysis. The anti-inflammatory effects of 1-8 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 4 and 7 exhibited moderate inhibitory effects on nitric oxide production in LPS-activated BV-2 cells, with IC50 values of 17.80 and 27.91 µM, respectively.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Capsella/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Animals , Cell Line , Cell Survival , Glycosides/isolation & purification , Inhibitory Concentration 50 , Lipopolysaccharides , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Nitric Oxide/metabolism , Phenols/chemistry , Plant Extracts/chemistryABSTRACT
Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.
Subject(s)
Glycosides/isolation & purification , Justicia/chemistry , Lignans/isolation & purification , Acanthaceae/chemistry , Glycosides/chemistry , Lignans/chemistry , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
AIM: To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring. METHODS: Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods. RESULTS: Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4- O-ß-D-glucopyranoside (2), (+)-medioresinol-4-O-ß-D-glucopyranoside (3), pinoresinol-4, 4'-di-O-ß-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8). CONCLUSION: Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.
Subject(s)
Benzofurans/isolation & purification , Glucosides/isolation & purification , Plant Extracts/chemistry , Selaginellaceae/chemistry , Benzofurans/chemistry , Furans/chemistry , Furans/isolation & purification , Glucosides/chemistry , Lignans/chemistry , Lignans/isolation & purification , Molecular Structure , Plant Stems/chemistry , Quercetin/chemistry , Quercetin/isolation & purificationABSTRACT
AIM@#To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring.@*METHODS@#Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods.@*RESULTS@#Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4- O-β-D-glucopyranoside (2), (+)-medioresinol-4-O-β-D-glucopyranoside (3), pinoresinol-4, 4'-di-O-β-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8).@*CONCLUSION@#Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.
