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Fourteen compounds were isolated from the n-butanol fraction of the 95% aqueous ethanol extract of the stems and twigs of Strychnos cathayensis by D101 macroporous resin, silica gel, ODS, Sephadex LH-20 column chromatography, and semipreparative RP-HPLC. Their structures were elucidated as ethyl 4-O-β-D-allopyranosyl-vanillate (1), n-butyl 4-O-β-D-allopyranosyl-vanillate (2), n-butyl 4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillate (3), n-butyl 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillate (4), n-butyl 4-O-(6′-O-syringoyl)-β-D-glucopyranosyl-vanillate (5), n-butyl 4-O-α-L-rhamnopyranosyl-syringate (6), methyl 3-methoxy-4-(β-D-allopyranosyloxy) benzoate (7), pseudolaroside B (8), butyl syringate (9), glucosyringic acid (10), methyl syringate (11), methyl 4-hydroxy-3-methoxybenzoate (12), clemochinenoside C (13), and clemoarmanoside A (14), respectively, on the basis of spectroscopic data interpretation and by comparison with literature information. Compounds 1-6 are artificial products of phenolic acid esterified by ethanol or n-butanol. It is noted that the precursors (4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillic acid and 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillic acid) of compounds 3 and 4 are new compounds. The hepatoprotective, anti-inflammatory, antioxidant and cytotoxic activities of compounds 1-13 were evaluated in vitro at a concentration of 10 μmol·L-1. Compounds 1, 2 and 6-10 exhibited potential hepatic protection effects with cell survival rates ranging from 53.6% to 55.5% (acetaminophen, 45.4% at 8 mmol·L-1). Compound 4 demonstrated anti-inflammatory activity with nitric oxide inhibitory rate of 74.6%. Compounds 3 and 5 showed potential antioxidant activities with malondialdehyde inhibitory rates of 53.2% and 56.1%, respectively.
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The phytochemical investigation of the stems of Homalium stenophyllum afforded seven new phenolic glycosides (1-5 and 8-9) and two known compounds (6 and 7). Their structures were elucidated by comprehensive analyses of NMR spectroscopic, mass spectrometric data and chemical hydrolysis. Additionally, their anti-inflammatory activities against the NO production in LPS-induced macrophages were evaluated.
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Objective: To study the chemical constituents from the aerial part of Allium sativum. Method: The aerial part of A. sativum was treated by heating reflux extraction with 70% ethanol. The combined extracting solution was treated with decompressed recovery solvent to obtain the total extract. The total extract's thick paste was suspended with an appropriate amount of distilled water, and then extracted with petroleum ether, ethyl acetate and water-saturated n-butyl alcohol to obtain petroleum ether extraction fraction, ethyl acetate extraction fraction and n-butyl alcohol extraction fraction. The n-butyl alcohol extraction fraction was isolated and purified by positive phase silica gel column chromatography, ODS column chromatography and preparative HPLC,etc. The structures of the chemical constituents were elucidated by means of physicochemical properties and spectroscopic analysis, and spectral data, like 1H-NMR, 13 C-NMR, DEPT, HMBC and HR-ESI-MS. Result: Seven compounds were isolated and identified as 2-methoxy-phenol-1-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside(1),phenyl-ethanol-4-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside(2),trans-resveratrol 3-O-β-D-glucopyranoside(3),stigmasterol(4),β-sitosterol(5),stigmasterol-3-O-β-D-glucopyranoside(6) and daucosterol(7). Conclusion: Compound 1 is a new phenolic glycoside named dasuanxinoside J,and compounds 2-7 are isolated from A. sativum for the first time.
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Two new phenolic glycosides, 7S, 8R-urolignoside-9'-O-β-D-glucoside (1) and scrophenoside G (2), were isolated and identified from the seeds of Ginkgo biloba L., a famous traditional medicine and functional food around the world. Their structures were elucidated by spectroscopic methods (1D and 2D NMR, HR-ESI-MS, and CD), and the comparisons of spectroscopic data with the reported values in the literature.
Subject(s)
Ginkgo biloba , Chemistry , Glycosides , Chemistry , Molecular Structure , Phenols , Chemistry , Plant Extracts , Chemistry , Plants, Medicinal , Chemistry , Seeds , Chemistry , Spectrum AnalysisABSTRACT
Two new phenolic glycosides, 7S, 8R-urolignoside-9'-O-β-D-glucoside (1) and scrophenoside G (2), were isolated and identified from the seeds of Ginkgo biloba L., a famous traditional medicine and functional food around the world. Their structures were elucidated by spectroscopic methods (1D and 2D NMR, HR-ESI-MS, and CD), and the comparisons of spectroscopic data with the reported values in the literature.
Subject(s)
Ginkgo biloba , Chemistry , Glycosides , Chemistry , Molecular Structure , Phenols , Chemistry , Plant Extracts , Chemistry , Plants, Medicinal , Chemistry , Seeds , Chemistry , Spectrum AnalysisABSTRACT
Objective: To find the genuine structure with anti-acetylcholinesterase(anti-AChE)from the phenolic glycosides abundant in Leonurus japonicus(Lamiaceae).The assay for anti-AChE activity is often used to lead anti-Alzheimer's drugs. Methods: The five phenolic glycosides, tiliroside, leonurusoside C, 2'''-syringoylrutin, rutin, and lavanduliofolioside were isolated from L. japonicus. The activities of the glycosides were relatively low. Seven compounds including p-coumaric acid, caffeic acid, hydroxytyrosol, salidroside, syringic acid, kaempferol, and quercetin, which are produced by the hydrolysis of the five glycosides, were also assayed for anti-AChE activity. Results: Of those seven compounds, the five compounds other than salidroside and syringic acid exhibited potent anti-AChE activities.In particular,the IC50s of caffeic acid and quercetin were (1.05 ± 0.19)and (3.58 ± 0.02)μg/mL, respectively. Rutin was the most abundant flavonoid in the extract(9.18 mg/g as measured by HPLC). Conclusion: The substances with potent anti-AChE were caffeic acid, quercetin, p-coumaric acid, kaempferol, and hydroxytyrosol that can be produced from their glycosides.
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Objective To study the chemical constituents from seed kernels of Entada phaseoloides. Methods The constituents were isolated and purified by silica gel and preparative HPLC column chromatographic methods, and their structures were identified by means of physicochemical properties and spectral analyses. Results Eight compounds were isolated from 70% ethanol extract of the seed kernels of E. phaseoloides, and identified as 4-methoxybenzyl-O-[α-L-arabinopyranosyl-(1→6)]-β-D-glucopyranoside (1), sinapyl-O-[β-D-apiofuranosyl-(1→2)]-O-β-D-glucopyranoside (2), 2-β-D-glucopyranosyloxy-5-hydroxy-phenylacetic acid (3), 2-β-D-glucopyranosyloxy-5-hydroxy-phenylacetic acid methyl ester (4), 5-O-β-D-glucopyranosyl-3-hydrobenzo [b] furan-2-one (5), dihydrophaseic acid-4'-O-β-D-glucopyranoside (6), corchoionoside C (7), and 1'S,4'S-4'-dihydroabscisic acid-4'-O-β-glucopyranoside (8). Conclusion Compound 1 is a new compound named phaseoloideside F, compound 5 is a new natural product, and compounds 2 and 4-8 are isolated from this plant for the first time.
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Objective To find the genuine structure with anti-acetylcholinesterase (anti-AChE) from the phenolic glycosides abundant in Leonurus japonicus (Lamiaceae). The assay for anti-AChE activity is often used to lead anti-Alzheimer's drugs. Methods The five phenolic glycosides, tiliroside, leonurusoside C, 2‴-syringoylrutin, rutin, and lavanduliofolioside were isolated from L. japonicus. The activities of the glycosides were relatively low. Seven compounds including p-coumaric acid, caffeic acid, hydroxytyrosol, salidroside, syringic acid, kaempferol, and quercetin, which are produced by the hydrolysis of the five glycosides, were also assayed for anti-AChE activity. Results Of those seven compounds, the five compounds other than salidroside and syringic acid exhibited potent anti-AChE activities. In particular, the IC
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Objective To observe the anti-osteoporotic activity of representative phenolic glycosides (curculigoside, curculigine A, orcinol glucoside and orcinol rhamnoside) in Curculigo orchioides on osteoblasts in neonatal rat calvaria and on osteoclasts induced by myelomonocytes.Methods The proliferation of osteoblasts and osteoclasts were determined by MTT assay. The alkaline phosphatase (ALP) activity of osteoblasts and tartrate-resistant acid phosphatase (TRAP) of osteoclasts were detected by using p-PNPP-Na method. The mineralized nodule formation was determined by alizarin red-s (AR-S) staining. TRAP-positive multinucleated cells were counted through TRAP staining. The cytoskeleton of osteoblasts and F-actin ring of osteoclasts were labeled with rhodamine-conjugated phalloidin, and observed under confocal laser scanning microscope. The areas of osteoclastic bone resorption pit in co-culture of osteoblasts and osteoclasts were determined using computer image process. Results Curculigoside (10-9 mol/L and 10-8mol/L) significantly promoted the proliferation of osteoblasts and inhibited the TRAP activity of osteoclasts at the concentration of 10-7-10-5 mol/L (P<0.05). Curculigoside, orcinol glucoside and orcinol rhamnoside significantly decreased the number of osteoclasts (P<0.05). Curculigoside (10-10mol/L), curculigine A (10-9mol/L), orcinol glucoside (10-9mol/L) and orcinol rhamnoside (10-9mol/L) significantly increased the ALP activity and bone mineralized nodule formation of osteoblasts (P<0.01), reduced the injury of cytoskeleton of osteoblast induced by 1, 25-(OH)2-VD3, decreased the pit area formed by osteoclasts, and destroyed F-actin cytoskeleton structure and pseudopodia of osteoclasts. Conclusion Curculigoside, curculigine A, orcinol glucoside and orcinol rhamnoside, phenolic glycosides extracted from Curculigo orchioides, can promote osteoblastic bone formation and inhibit osteoclastic bone resorption, demonstrating a significant anti-osteoporotic activity.
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This review analyzed domestic and foreign literatures on intestinal absorption,introduced the current methods and models commonly used in phenolic glycosides researches and their impacts focused on intestinal absorption,summarized the research status,aims to provide a reference for improving their oral bioavailability,improve formulations,new medicine and clinical rational use of phenolic glycosides.
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Abstract Ten compounds were isolated from the stems of Viburnum plicatum Thunb.vat.tomentosum Miq.and were identified as 3,4,5-trimethoxyphenyl-l-O-β-D-glucopyranoside (1),isotachioside (2),tachioside (3),koaburaside (4),glucosyringic acid (5),lupeol (6),ursolic acid (7),chlorogenic acid (8),5-O-caffeoyl quinic acid butyl ester (9),and tricin-7-O-β-D-glucoside (10),respectively.Compounds 1-10 were isolated from this plant for the first time.
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OBJECTIVE: To establish a RP-HPLC method for the simultaneous determination of phenolic glycosides in Curculigins Rhizoma. METHODS: Angilent 1100 HPLC on a ZORBAX SB C18 column(4.6 mm × 250 mm, 5 μm) with Extend C18 guard column(4.6 mm × 12.5 mm, 5 μm) were used. The mobile phase consisted of acetonitrile(A)-0.1% phosphoric acid aqueous(B). The gradient elution program was as follows: 0-25 min, 4%-6% A; 25-58 min, 6% - 17% A; 58-85 min, 17%-22% A The flow rate was kept at 1 mL · min-1, and the column temperature was set at 30°C. The detection wavelength was 230 nm. RESULTS: The concentrations and peak areas of the 8 phenolic glycosides including 5-hydroxymethylfurfural(1), 2-hydroxy-5-(2-hydroxyethyl) phenyl-β-D-glucopyranoside(2), anacardoside (3), orcinol glucoside (4), orcinol-1-O-β-D-apiofuranosyl-(1 → 6) -β-D-glucopyrano-side(5), 2, 6-dimethoxybenzoic acid(6), curculigoside(7) and curculigine A(8) were in good linear relationship. The average recoveries of the 8 constituents met the requirement for determination. CONCLUSION: The method is simple, sensitive, reproductive, and suitable for simultaneous determination of a variety of phenolic glycosides in Curculigins Rhizoma. Copyright 2012 by the Chinese Pharmaceutical Association.
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Objective: To isolate and identify phenolic glycosides and lignans from the rhizomes of Curculigo orchioides Gaertn. Methods: Phenolic glycosides and lignans were isolated by silica gel, Sephadex LH-20 chromatography and semi-preparative HPLC methods. The structures of the isolated compounds were identified by physiochemical and spectral analysis/ Results: Five phenolic glycosides,one lignan and one sitosterol were isolated and identified from Curculigo orchioides Gaertn, namely, 2,6-dimethoxy benzolic acid(1), curculigoside A(2), curculigoside B(3), curculigine A(4), 4-dichlorine-5-hydroxyl-3-methylphenol-1-O-β- D-glucopyranosyl-(1→-6)-β-3-D-gluco-pyranosede(5), 3,3′,5,5′-tetramethoxy-7,9′:7′,9 -diepoxylignan -4, 4′-di-O-β-D-glucopyranoside(6),and β-sitosterol(7). Conclusion: Seven compounds have been isolated from Curculigo orchioides Gaertn; compound 5 is a new chlorine-containing phenol, and is named as curculigine D.
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Objective To optimize the extraction process for phenolic glycosides from Rhizoma Curculigins. Methods The contents of orcinol glucoside,curculigoside and curculigine were used as parameters, and they were determined by HPLC. The extraction conditions of phenolic glycosides from Rhizoma Curculigins were optimized using orthogonal design. The examined factors included concentration of ethanol(50% , 70% , and 95%) , extraction time (1, 1.5, and 2 h) , times of extraction (1,2, and 3) , and solvent volume (6, 8, and 10 times). Results The concentration of ethanol, extraction time, times of extraction and solvent volume significantly affected the extraction efficacy of phenolic glycosides in Rhizoma Curculigins, with the most prominent effect exerted by the ethanol concentration. The optimal extraction process was refluxing three times with 70% ethanol (10 times of solvent volume), for 2 h each time. Conclusion The present method can effectively extract phenolic glycosides from Rhizoma Curculigin, which paves a way for further research on phenolic glycosides in Rhizoma Curculigins.
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Aim To investigate the water-soluble phenolic glycosides from the whole plant of Bulbophyllum odoratissimum. Methods Column chromatography techniques were used to isolate the chemical constituents, physico-chemical constants and spectroscopic analysis were employed for structural elucidation. Results Bulbophyllinoside (1), a new phenolic glycoside and three known compounds were isolated from the whole plant of Bulbophyllum odoratissimum Lindl. Their structures were determined as 3-hydroxyphenethyl alcohol 4-O-(6'-O-β-apiofuranosyl)-β-D-glucopyranoside (1), 3-methoxyphenethyl alcohol 4-O-β-D-glucopynanoside (2), 3,5-dimethoxyphenethyl alcohol 4-O-β-D-glucopynanoside (3) and syringin (4). Conclusion Bulbophyllinoside (1) is a new compound.
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Object To study the chemical constituents in Ligustrum sinense Lour.Methods One new and four known phenolic glycosides were isolated and identified by column chromatography, MS, IR and NMR data.Results Five phenolic and two lignan components were isolated from water soluble part in methanol extract of the stem and leaves of L.sinense.The obtained compounds were identified as sinenosides I, 8′-?-hydroxyl-lariciresinol-4′-O-?-L-glucopyranoside (Ⅰ), a new compound; liriodendrin (Ⅱ); kaempferol-3-O-?-D-glucopyranoside (Ⅲ); 7-O-?-L-rhamnopyransyl-kaempeferol-3-O-?-D-glucopyranoside (Ⅳ), 7-O-?-D-rhamnopyransyl-kaempeferol-3-O-?-D-rhamnopyranoside (Ⅴ).Conclusion All the compounds were isolated from this plant for the first time.
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Objective To investigate the chemical constituents in the barks of Populus davidiana. Methods The constituent was isolated by column chromatography and its structure was determined on the basis of chemical and spectral data. Results Compound Ⅰ was identified as (E)-5-hydroxy-2-[3, 4, 5,-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy] benzyl 3-(4-hydroxypenyl) acrylate. Conclusion Compound I is a new phenolic glycoside named as davidianoside.
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Objective To investigate the chemical constituents in the barks of Populus davidiana. Methods The constituents were isolated by column chromatography and their structures were determined on the basis of chemical and spectral data. Results Sixteen compounds were isolated and twelve of them were identified as 3?-acetoxyurs-12-en-28-oicacid (Ⅰ), ?-sitosterol (Ⅱ), 4-methoxyphenol (Ⅲ), 3-methoxyphenol (Ⅳ), sakuranetin (Ⅴ), scopoletin (Ⅵ), 2R, 3R-dihydro-7-methoxy-kaempferol (Ⅶ), salicyloyltremuloidin (Ⅷ), tremuloidin (Ⅸ), ?-sitosterol-3-O-glucoside (Ⅹ), salireposide (Ⅺ), and sakuranin ( ⅩⅡ ). Conclusion Compounds Ⅰ, Ⅴ, Ⅵ, and ⅩⅡ are isolated from the plants of Populus L. for the first time.