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Objective: To isolate and identify the major bioactive components from the leaves of Lysiphyllum strychnifolium, an indigenous herb used in traditional Thai medicine for detoxification, longevity, and some other health related issues. Methods: Comparative HPLC analyses of the crude extracts from three provenances were carried out for an overview of characteristic compound profiles. Isolation of the major compounds was undertaken with chromatographic methods. Chemical structures were elucidated by NMR spectroscopic techniques and mass spectrometry. DPPH scavenging assay was carried out to determine the free radical scavenging activity of isolated compounds. Results: Yanangdaengin (3), a dihydrochalcone glucoside galloyl ester, has been isolated together with its corresponding dihydrochalcone glucoside trilobatin (2) as major compounds from the leaves of L. strychnifolium. Additionally, gallic acid (1) was co-chromatographically identified. Free radical scavenging activity of isolated compounds were determined. Compound 3 exhibited higher free radical scavenging activities in comparison to Trolox and quercetin. Conclusion: The isolated compounds could be used as chemical markers for quality assessment. The present work could promote the quality control and herbal medicinal product development of this plant.
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Objective: To rapidly screen the potential analgesic ingredients from Draconis Resina by live cell immobilized chromatography coupled with HRMS. Methods: An HPLC-DAD-ESI-TOF-MS technique was used to rapidly identify the main chemical constituents from Draconis Resina. Based on the bio-specific affinity adsorption of bioactive compounds with receptors or channels on cells, the potential bioactive components in Draconis Resina could be selectively bound to the target cells-mice dorsal root neurons cells, then the chemical constituents with cell target affinity were identified by LC-HRMS. Results: A total of 21 compounds with various structures were tentatively identified and characterized by HPLC-DAD-ESI-TOF-MS, and among them, 10 potentially analgesic active ingredients in Draconis Resina extract combined with dorsal root neurons cells were successfully detected and identified, including two stilbene, two homoisoflavones, one homoisoflavone, two dihydrochalcone, and three flavonoid oligomers. Conclusion: Live cell immobilized chromatography coupled with LC-DAD-HRMS analysis could provide a rapid and efficient tool for finding the potential bioactive components in Draconis Resina for the next pharmacology studies, which provide the reference for exploring of effective materials basis in Chinese medicines.
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ABSTRACT The secondary metabolites of the aerial parts of Zornia brasiliensis Vogel, Fabaceae, and the biological activity of one of these secondary metabolites were characterized in this study. A phytochemical investigation was performed using chromatographic techniques including analytical and preparative reverse-phase HPLC column sequences, which resulted in the isolation of fourteen compounds: one previously undescribed C-glycosylated dihydrochalcone (zornioside), one cyclitol (D-pinitol), one glycosylated megastigmane (roseoside) and eleven phenolic compounds: 7-methoxyflavanone, 7,4'-dimethoxyisoflavone, medicarpin, 2'-4'-dihydroxychalcone, onionin, isoorientin-3'-O-methyl ether, isovitexin, glycosylated (Z)-O-coumaric acid, glycosylated (E)-O-coumaric acid, dihydromelilotoside, and isoorientin. The structures of the isolated compounds were determined based on 1D and 2D-NMR, HRESIMS, IR and CD spectroscopic analyses. The cytotoxic activity of zornoside was assessed against tumor cell lines (MCF-7, HCC1954, T-47D, 4T1, HL60), and a non-tumor cell line (RAW264.7) using MTT assay. The compound zornioside was selectively cytotoxic for HL60 leukemia cells (IC50: 37.26 µM).
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Objective: To study the chemical constituents of Penthorum chinense. Methods: The compounds were isolated and repeatedly purified by column chromatography over macroperous resin, polyamide, silica gel, and Sephadex LH-20, preparative TLC, and preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. Results: Nine flavonoids were isolated and identified as 6'-hydroxy-2'-methoxy-dihydrochalcone-4'-O-β-D-glucopyranoside (1), kaempferol (2), qercetin (3), quercitrin (4), avicularin (5), afzelin (6), helicin (7), pinocembrin-7-O-[4″,6″-(S)-hexahydroxydiphenoyl]-β-D- glucoside (8), and pinocembrin-7-O-[3″-O-galloyl-4″,6″-(S)-hexahydroxydiphenoyl]-β-D-glucoside (9). Conclusion: Compound 1 is a new dihydrochalcone and named penchinoside. Compounds 5-7 are isolated from genus Penthorum Gronov. ex L.for the first time.
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Objective: To study the chemical constituents from Empetrum nigrum var. japonicum. Methods: Compounds were isolated from n-hexane fraction in the industrial methanol extract from E. nigrum var. japonicum by silica gel column chromatography and HPLC. The structures of the chemical constituents were identified by analysis on their spectral data. All the isolated compounds were evaluated using relevant in vitro antitumor assay against HeLa cell lines. Results: Six compounds were isolated from n-hexane fraction in the ethanol extract from E. nigrum var. japonicum and identified as 2',5'-dihydroxy-3'-methoxy-4',6'-dimethyl-dihydrochalcone (1), 4',5'-dihydroxy-2'-methoxy-3',6'-dimethyl-dihydrochalcone (2), 2',4'-dihydroxy-dihydrochalcone (3), 2',4'-dihydroxy-chalcone (4), 2'-methoxy-4'-hydroxy-dihydrochalcone (5), and 2',4',β-trihydroxy-dihydrochalcone (6). Conclusion: Compounds 1 and 2 are new compounds, compounds 5 and 6 are obtained from the plants for the first time. Compound 6 exhibits the inhibitory activity.
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Objective: To study the chemical constituents from the ethyl acetate extract fraction of 70% ethanol extract in the aerial parts of northeastern crowberry (Empetrum nigrum var. japonicum) and their effect on the alcohol fatty liver (AFL) of rats, and to provide the scientific basis for the use and development of the northeastern crowberry. Methods: Chromatography separation technology and spectral analysis technology were used for the separation, purification, structure analysis, and identification. AFL model of SD rats was induced by 45% ethanol. To observe the effect of ethyl acetate extract in northeastern crowberry on the liver index, serology, and liver tissue homogenates in AFL of rats. Results: Eight compounds were isolated and identified as β-sitosterol (1), ursolic acid (2), uvaol (3), 2',4'-dihydroxy dihydrochalcone (4), 2',4'-dihydroxy chalcone (5), 7-hydroxy flavone (6), 4'-methoxy-2'-hydroxyl-dihydroxy chalcone (7), and isoliquiritigenin (8). Compared with the model group, giving the ethyl acetate extract of northeastern crowberry could decrease the liver index of rats, reduce serum lipid metabolism of TG, TC, reduce the serum enzyme ALT, AST, liver homogenate in oxidative stress, and increase the activities of SOD and GSH. Conclusion: Compounds 1-4, and 6-8 are isolated from E. nigrum var. japonicum for the first time. The effect of ethyl acetate extract in E. nigrum var. japonicum on AFL of rats is obvious.
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Objective: To study the chemical constituents from the herbs of Empetrum nigrum var. japonicum. Methods: The compounds were isolated and purified by silica gel, MCI gel, Sephadex LH-20 column chromatographies, semi-preparative HPLC, and their structures were mainly elucidated on the basis of physicochemical characteristics and spectral analysis. Results: Twelve compounds were isolated from 95% EtOH extract of E. nigrum var. japonicum, and were identified as 3β-hydroxy-nigrum-21-en (1), 4'-hydroxy-α, β-dihydrochalcone-2'-O-β-D-glucopyranoside (2), 5-(2-phenylethyl)-3-hydroxyphenol-1-O-β-D-glucopyranoside (3), 2', 4'-dihydroxy-chalcone (4), 2'-methoxy-4'-hydroxy-α, β-dihydrochalcone (5), phenylpropionic acid (6), cinnamyl alcohol (7), quercetin (8), (-)-epicatechin (9), quercetin-3-O-α-L-arabinoside (10), hyperoside (11), and 8-methoxyquercetin-3-glucoside (12), respectively. Conclusion: Compound 1 is a new triterpenoid and compound 2 is a new dihydrochalcone.