Résumé
Objective: To investigate the chemical constituents from whole herbs of Azolla imbricata. Methods: The chemical constituents were separated and purified by various chromatographic techniques of silica gel, ODS, Sephadex LH-20 gel, and semi-preparative HPLC. Their structures were identified by NMR and MS spectroscopic methods. Results: Twenty compounds were isolated from A. imbricata and identified as chlorogenic acid methyl ester (1), 4-O-caffeoylquinic acid (2), 3,4-O-dicaffeoylquinic acid methyl ester (3), 3,4,5-O-tricaffeoylquinic acid methyl ester (4), (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine (5), (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine (6), (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine methyl ester (7), (-)-N- [4'-hydroxy-(E)-cinnamoyl)]-L-tyrosine (8), brainicin (9), quercetin-3-O-β-D-glucoside (10), naringenin-7-O-β-D-glucoside (11), kaempferol-3-O-(6″-O-caffeoyl)-β-D-glucoside (12), caffeic acid (13), epirhododendrin (14), myzodendrone (15), trans-ferulic acid-β-D-glucoside (16), 5,7-dihydroxychromone-2-carboxylic acid (17), pinoresinol-4-O-β-D-glucoside (18), phytol (19) and trans-12-oxo-(10Z,15Z)-phytodienoic acid (20). Conclusion: Compounds 1-12, 14-18, and 20 are isolated from the genus Azolla for the first time and compound 19 is isolated from A. imbricata for the first time. Compounds 1-7, 10, 12, and 13 exhibit good antioxidant activity.
Résumé
Objective: To investigate the chemical constituents from Juniperus convallium, as well as their anticomplementary and antioxidant activities. Methods: The constituents were isolated and purified by column chromatography over silica gel, Sephadex LH-20, ODS-C18, and preparative HPLC. Their structures were identified by spectra analysis. The cell hemolysis assay was used to evaluate the anticomplementary activities and the targets through classical and alternative pathways. Also the anti-oxidant activities were tested by DPPH, ABTS and FRAP methods. Results: A total of 17 compounds were obtained from the ethyl acetate extract of J. convallium and identified as amentoflavone (1), cupressuflavone (2), cupressuflavone-4″’-O-β-D-glucosides (3), naringenin-7-O- glycoside (4), apigenin (5), tiliroside (6), quercetin 3-O-β-D-glucoside (7), quercetin-3-O-rhamnoside (8), hypolaetin-7-O-β-D- glucopyranoside (9), isomassonianoside B (10), (+)-isolariciresinol 2a-O-β-D-glucoside (11), (+)-isolarisiresinol 3a-O-β-D-glucopyranoside(12), cryptomeridiol (13), 3β-hydroxysandaracopimeric acid (14), (1R,3R,4aR,4bS,7R,10aR)-7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a- dodecahydro-3-hydroxy-1,4a,7-trimethyl-1-phenanthrene methanol (15), 4-hydroxy-5-methyl-coumarin (16) and β-sitosterol (17). Compounds 1-15 and 17 showed anticomplementary activities in different degrees (CH50: 0.05-3.99 mmol/L, AP50: 0.58 -19.13 mmol/L). The flavonoids, especially the biflavonoids, are the important anticomplementary constituents in J. convallium. Further analysis of structure-activity relationship showed that phenolic hydroxyl and glycosidic groups influenced their anticomplementary activity. Only the flavonoids (1-3, 5-9) and lignans (10-12) showed different degrees of antioxidant activities due to their hydroxyl groups. Conclusion: All the 17 compounds are isolated from J. convallium for the first time. The flavonoids and lignans are the important anticomplementary and antioxidant constituents in J. convallium with a certain structure-acticity relationship. This study provides a good reference for further research on the pharmacological substance and quality control of J. convallium.
Résumé
OBJECTIVE: To study the chemical constituents of Callicarpa nudiflora. METHODS: The chemical constituents were isolated and purified by column chromatography on silica gel, ODS, Sephadex LH-20 and MPLC. Their structures were elucidated by spectroscopic evidence and compared with those in literature. RESULTS: Nine compounds were isolated and identified as 6-O-caffeoyl ajugol(1), leucosceptoslde A(2), 6-O-caffeoly-β-glucose(3), nudifloside(4), luteolin-7-O-glucoside(5), quercetin 3'-O-β-D-glucoside(6), cistaneside C(7), acteoside(8), and syringalide A 3'-α-L-rhamnopyranoside (9). CONCLUSION: Compounds 1, 2, 6, 7, and 9 are isolated from this plant for the first time.
Résumé
Objective: To study the chemical constituents of Limonium sinense. Methods: Eleven compounds were isolated by extraction, preparation-TLC, repeat-silicagel column, Sephadex-LH20, and opened-ODS column chromatography, and identified on the basis of physicochemical constant and spectra analysis. Results: Eleven compounds were isolated and their structures were identified as isorhamnetin (1), mannitol (2), β-sitosterol (3), oleanolic acid (4), quercetin (5), quercetin-3-O-β-D-glucoside (6), ethylgallate (7), kaempferol (8), kaempferol-3-O-α-L-rhamnopyranoside (9), (+)-catechin (10), and isorhamnetin-3-rutinoside (11). Conclusion: Compounds 4, 6, 7,10, and 11 are obtained from L. sinense for the first time.