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Objective: To study the chemical constituents in the fruits of Actinidia arguta. Methods: The compounds were isolated by column chromatography on silica gel, ODS, and Sephadex LH-20, preparative TLC, and semi-preparative HPLC. The structures were established by the analyses of the spectroscopic data. Results: Fifteen compounds were obtained from the n-BuOH fraction of the 75% ethanol extract of the fruits of A. arguta and identified as (2R,6R,9R)-trihydroxy-megastigmane-4,7E-dien-3-one-9-O-β-D- glucopyranoside (1), (6S,9R)-roseoside (2), quercetin-3-O-b-D-galactopyranside (3), astragalin (4), vanillic acid-4-O-β-D- glucopyranoside (5), 1-O-feruloyl-β-D-glucopyranoside (6), ferulic acid-4-O-β-D-glucopyranoside (7), rhodioloside (8), 3-hydroxy-1-(4-O-β-D-glucopyranosyl-3- methoxyphenyl) propan-1-one (9), 5-O-caffeoyl quinic acid methyl ester (10), 5-O-caffeoyl quinic acid butyl ester (11), 5-O-feruloyl quinic acid methyl ester (12), 5-O-coumaroyl quinic acid methyl ester (13), caffeic acid (14), and protocatechuic acid (15). Conclusion: Compound 1 is a new norsesquiterpene glycoside with the megastigmane scaffold, named actinargutaside A. Compounds 2, 5, and 7-13 are isolated from the Actinidia genus for the first time and compound 6 is firstly isolated from A. arguta.
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ABSTRACT Persea americana Mill., Lauraceae, commonly known as the avocado, is native to tropical and subtropical regions, including Brazil. From the leaves of P. americana, one previously undescribed flavonol glycoside (1) together with ten known flavonoids (2-11), four megastigmane glycosides (12-15) and two lignans (16-17) were isolated. Their structures were determined by extensive spectroscopic methods including 1D- and 2D-nuclear magnetic resonance and mass spectrometry data. This is the first investigation that reports megastigmane glycoside and lignan classes within the genus Persea. All the isolated compounds have been assessed through the cell survival of larval zebrafish following neomycin-induced damage and the cell viability of a House Ear Institute-Organ of Corti 1 mouse auditory cell line. Among the tested compounds, juglanin (2) and (+)-lyoniresinol (16) showed significant cell regeneration in neomycin-damaged hair cell without cellular toxicity.
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Objective: Dichocarpum auriculatum, an endangered perennial herb, is endemic to China and has been used as folk medicines for the treatment of cough, hepatitis, scrofula, and epilepsy. However, there is no phytochemical report on this herbal so far. For the resource development and protective importance of this endangered medicinal plant, a phytochemical study was undertaken. Methods: The chemical constituents were purified by silica gel column, Sephadex LH-20 column, and semi-preparative reversed phase HPLC. NMR and MS spectra were used for structural identification. Results: Thirteen compounds were isolated from D. auriculatum. Their structures were characterized as jatrorrhizine (1), berberine (2), steponine (3), magnoflorine (4), coclauril (5), menisdaurin (6), menisdaurilide (7), aquilegiolide (8), (6R, 9S)-3-oxo-α-ionol-β-D-glucopyranoside (9), blumenol C glucoside (10), palmitic acid (11), dibutylphthalate (12), and auriculatum A (13). Conclusion: Compound 13 is a new diester terephthalate derivative. All the compounds are obtained from the genus Dichocarpum for the first time, and compounds 9 and 10 have potential chemotaxonomic significance to the genus Dichocarpum.
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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 Whole Plants of Patrinia villosa (Thunb.) Juss. METHODS: Compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, Sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by physiochemical properties and spectral analysis. RESULTS: Nine compounds were isolated and identified as (E, 4R)-4-hydroxy-4, 5, 5-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enone (1), vomifoliol (2), cis-4-hydroxymellein (3), dehydrovomifoliol (4), 3R, 5S, 6R, 7E, 9S-3, 5, 6, 9-tetrahydroxy-7-megastigmane (5), loliolide (6), 4-methoxybenzyl alcohol (7), sphenanthin A (8), and urea (9). CONCLUSION: Compounds 1-7 are isolated fromPatrinia genus for the first time.
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The present study was designed to investigate the chemical constituents of the whole herb of Dichrocephala benthamii. A new megastigmane glucoside (compound 1), together with its four known analogues (compounds 2-5), was obtained. Their structures were elucidated on the basis of spectroscopic analyses (UV, IR, MS, and 1D and 2D NMR). The absolute configuration of compound 1 was assigned on the basis of CD method and chemical evidence. In addition, their cytotoxicity against human hepatoma cells (HepG-2) was evaluated by the MTT method. Compound 5 showed weak activity against HepG-2, while the other compounds did not show remarkable inhibitory effects.
Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Chemistry , Pharmacology , Asteraceae , Chemistry , China , Cyclohexanones , Chemistry , Pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal , Chemistry , Glucosides , Chemistry , Pharmacology , Hep G2 Cells , Molecular Structure , Norisoprenoids , Chemistry , Pharmacology , Plants, MedicinalABSTRACT
Objective: To study the chemical constituents in 60% ethanol extract from the aerial parts of Matteuccia struthiopteris. Methods: Diaion HP20 macroporous adsorption resin column chromatography (CC), silica gel CC, ODS CC, Sephadex LH-20 CC, and PHPLC were used for the isolation and purification. Structures were identified on the basis of chemical evidences and spectroscopic analyses. Results: Twelve compounds were isolated and identified as 4,7-megastigmadiene-3,9-diol (1), blumenol A (2), dehydrovomifoliol (3), bridelionol F (4), bridelionol B (5), 3,5,6-trihydroxy-7-megastigmen-9-one (6), 5β,6α-dihydroxy-3β-(β-D- glucoyranosyloxy)-7-megastigmen-9-one (7), byzantionoside A (8), dearabinosyl pneumonanthoside (9), 3-hydroxy-β-damascone glucoside (10), amarantholidoside IV (11), and icariside C3 (12). Conclusion: Compounds 1-12 are reported from the plants of Matteuccia Todaro for the first time.
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AIM@#To study the chemical constituents of the aerial parts of Cirsium setosum (Willd.) MB..@*METHODS@#The chemical constituents were isolated and purified by various chromatographic techniques. Their structures were determined on the basis of physical properties and spectroscopic data.@*RESULTS@#A new megastigmane glycoside and six known compounds were obtained and identified as (7E, 9R)-9-hydroxy-5, 7-megastigmadien-4-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyanoside (1), (6R, 7E, 9R)-9-hydroxy-4, 7-megastigmadien-3-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2), urolignoside (3), 4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4$\prime $-neolignan-7-O-β-D-glucopyranoside (4), citroside A (5), salidrosidin (6), and adenosine (7).@*CONCLUSION@#Compound 1 is a new megastigmane glycoside, named as Xiaojiglycoside A.