RESUMEN
Objective: To investigate the flavonoids and lignans from the flowers of Stellera chamaejasme and their structure-activity relationship (SAR) of antioxidant activity. Methods: The compounds were isolated by column chromatography and HPLC packed with macroporous resin, silica gel, and Sephadex LH-20. Their structures were elucidated by spectroscopic analysis. Their anti-oxidant activities in vitro were evaluated by DPPH, ABTS, and FRAP assays. Results: Twelve compounds were isolated from the flowers of S. chamaejasme, and identified as artemisetin (1), quercetin (2), isoscutellarein-8-O-β-D-glucuronopyranoside (3), quercetin-3-O-β-D- glucopyranoside (4), astragalin (5), hypolaetin-8-O-β-D-glucuronopyranoside (6), kaempferol 3-O-β-D-glucopyranosyl-(1→2)-O-α- L-xylopyranoside (7), rel-(3R,3'S,4R,4'S)-3,3',4,4'-tetrahydro-6,6'-dimethoxy [3,3'-bi-2H-benzopyran]-4,4'-diol (8), matairesinol (9), uralenol (10), cycloastragenol (11), and (+)-pinoresinol (12). Conclusion: Compounds 1, 3, 5-7, and 10 are isolated from this plant for the first time, and compounds 2, 4, 5, and 10 showed significant antioxidant activity, and the SAR analysis suggested that the glycosylation at the C-8 or C-3 position of flavonoids could weaken their antioxidant activity.
RESUMEN
Objective: To study the glycosides from the 70% ethanol extract of Lonicera macranthoides. Methods: The compounds were isolated and purified by column chromatography of HP-20 macroporous resin, silica gel, ODS, Sephadex LH-20, and semi-preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. Results: Eight compounds were isolated and identified as 7,3’,4’-trimethoxylquercetin-3-O-α-L-arabinadosyl-(1→6)-O-β-D-glucopyranoside (1), 7,3’,4’-trimethoxylquercetin-3-O-rutoside (2), quercetin-3-O-β-D-glucopyranoside (3), (2E,6S)-8-[α-L-arabinopyranosyl-(1″→6’)- β-D-glucopyranosyl]-2,6-dimethyloct-2-eno-1,2″-lactone (4), kankanoside E (5), betulalbuside A (6), shomaside F (7), and amarantholidoside V (8), respectively. Conclusion: Compound 1 is a new compound named methoxylquercetinside, while compounds 5-8 are isolated from the genus of Lonicera for the first time.
RESUMEN
Objective To isolate and identify chemical ingredients with anti-complement activity from Aster ageratoides and investigate the key targets and anti-inflammatory activities of obtained compounds with good anti-complement activity. Methods Using silica gel column, sephadex LH-20 column, Medium Pressure Liquid Chromatography system, and Semi-preparative HPLC, chemical ingredients that displayed anti-complement activity were isolated. Their chemical structures were identified by 1H-NMR and 13C-NMR and their anti-complement activities and targets were investigated by erythrocyte hemolysis in vitro. In addition, using LPS-stimulated RAW264.7 cells, we investigated the anti-inflammatory activity of compound 2. Results A total of 14 compounds were obtained from A. ageratoides and identified as oleanolic acid (1), quercetin (2), kaempferol (3), 3,5,7,3’-tetrahydroxy- 4’-methoxyflavone (4), kaempferol-7-O-α-L-rhamnopyranoside (5), quercetin-3-O-β-D-glucopyranoside (6), kaempferol-3-O-α-L- rhamnoside (7), quercetin-3-O-α-L-rhamnoside (8), kaempferide-3-O-β-D-glucopyranoside (9), kaempferol-3-O-β-D- glucopyranoside (10), kaempferol-7-O-β-D-glucopyranoside (11), kaempferol-3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside (12), kaempferide-3-O-α-L-rhamnoside-(1→6)-β-D-glucopyranoside (13), and rutin (14). They all exhibited anti-complement activity to some certain degree and good structure-activity relationship. The targets of compounds 1 and 2 were C1q, C5, and C9 and C1q, C2, C5, and C9, respectively. The anti-inflammatory experiments indicated that compound 2 exhibited a significant biological activity, which significantly suppressed the release of NO, TNF-α, and IL-6 and expressions of iNOS and COX-2. Conclusion A total of 14 compounds were obtained and they all displayed anticomplement activity, of which compounds 1, 4, 6, 9, 12, and 13 are firstly discovered in A. ageratoides. Compound 2 exhibited a significant anti-inflammatory activity.
RESUMEN
Objective To study the chemical constituents from Calystegia sepium. Methods The compounds were isolated and purified by silica gel column chromatography, Sephadex LH-20, ODS column chromatography, preparative HPLC and so on. Their structures were determined on the basis of physicochemical properties and their spectroscopic data, as well as literatures. Results A total of 20 compounds were separated and identified as tyrosol (1), quercetin-3-O-β-D-glucopyranoside (2), scutellarein-7-O-β- glucopyranoside (3), kaempferol-3-O-β-D-glucopyranoside (4), kaempferol-3-O-galactoside (5), kaempferol-3-O-β-robinobioside (6), nicotiflorin (7), rutin (8), uridine (9), tachioside (10), 2-methoxy-4-(2’-hydroxyethyl)-phenyl-1-O-β-D-glucopyranoside (11), 4-hydroxyphenethylol-4-O-β-D-glucopyranoside (12), polybotrin (13), pyridine-3,5-dicarboamide (14), skimmin (15), benzylalcohol-β-D-glucopyranoside (16), 5-hydroxyl-2-hydroxymethylpyridine (17), picein (18), 5-hydroxymethyl-furaldehyde (19), and sessiline (20). Conclusion Compounds 1-20 are isolated from Calystegia sepium for the first time.
RESUMEN
OBJECTIVE: To investigate the chemical constituents of the aerial parts of Ribes diacanthum Pall. METHODS: The compounds were isolated and purified by silica gel, Sephadex LH-20 colunm chromatography and HPLC. The structures were elucidated on the basis of spectral data and physiochemical properties. RESULTS: Nineteen compounds were isolated from 95% ethanol extracts and identified as quercetin (1), quercetin-3-O-β-D-glucopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), quercetin-3-O-β-D-neohesperoside (4), mearnsetin (5), myricetin-3-O-α-L-rhamnoside (6), myricetin-3-O-β-D-glucopyranoside (7), mearnsetin 3-O-β-D-glucopyranoside (8), mearnsetin 3-O-α-L-rhamnopyranoside (9), kaempferol-3-O-β-D-glucopyranoside (10), kaempferol 3-O-β-D-(2-O-α-L-rhamnopyranosyl) glucopyranoside (11), kaempferol 3-(2'', 6''-di-O-α-L-rhamnosyl)-β-D-glucoside (12), 1, 2, 4-trihydroxybenzene (13), vanillic acid (14), protocatechuic acid (15), 4-hydroxy benzoic acid (16), gallic acid (17), blumenol C glucoside (18), conocarpan (19). CONCLUSION: All the compounds are isolated from the title plant and the NMR data for 8 is reported here for the first time.
RESUMEN
Objective: To investigate the chemical constituents from the roots and rhizomes of Rhodiola sachalinensis. Methods: The chemical constituents were isolated by repeated silica gel chromatography, medium pressure column chromatography, and semi-preparative liquid chromatography, and their structures were elucidated by chemical properties and spectroscopic analyses. Results: Eighteen compounds were isolated and identified to be gallic acid (1), p-hydroxybenzoic acid (2), salidroside (3), benzyl-O-β-D-glucopyranodide (4), phenylethyl-8-O-β-D-glucopyranodide (5), cinnamyl-β-D-glucopyranoside (6), sachalinol (7), quercetin (8), quercetin-3-O-β-D-glucopyranoside (9), kaempferol (10), kaemferol-7-O-α-L-rhamnopyranoside (11), kaempferol- 7-O-β-D-glucopyranoside (12), kaemnpferol-3-O-α-L-rhamnoside (13), kaempferol-3-O-β-D-glucopyranoside-7-O-α-L-rhamnoside (14), tricin (15), tamarixetin (16), herbacetin-7-O-α-L-rhamnoside (17), and herbacetin-3-O-β-D-glucopyranoside-7-O-α-L- rhamnoside (18). Conclusion: Compounds 9, 12, and 16 are obtained from the plants in Rhodiola L. for the first time. Compounds 2, 7, 8, 14, and 18 are obtained from this plant for the first time.