syringin and 1-1-diphenyl-2-picrylhydrazyl

To study the chemical constituents from Pachysandra terminalis and their antioxidant activity.. Chemical constituents were isolated by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). The structures of isolated compounds were elucidated on the basis of spectral data analysis. DPPH method was used to evaluate the free radical scavenging activity of the isolated compounds.. Six compounds were isolated and their structures were identified as follow: 2-Phenylethyl-beta-D-glucopyranoside (1), (+)Pinoresinol-4'-O-beta-D-glucopyranoside (2), Pinoresinol (3), cis-Syringin (4), 4-hydroxy-4-(3-oxo-l-butenyl)-3,5,5-trimethylcyclohex-2-en-l-one (5), 3alpha-hydroxy-5,6-epoxy-7-megastigmen-9-one (6). Compounds 2, 4, 5 showed obviously antioxidant activity, their DPPH free radical scavenging rates were 82.50%, 87.36%, and 84.56% on the concentration of 50 micromol/L, respectively.. Compounds 1-6 are isolated from this genus for the first time. Compounds 2, 4, and 5 showed significant antioxidant activities.

Topics: Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Free Radical Scavengers; Furans; Glucosides; Glycosides; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Pachysandra; Phenylethyl Alcohol; Phenylpropionates; Picrates; Plant Extracts; Plants, Medicinal

A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-butyrolactone lignans, styraxlignolides C-F (2-5), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica. Known compounds, taraxerol (6), syringin (7), and (-)-pinoresinol glucoside (8), were also obtained. The structures of styraxligonolides B-F were determined as 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(3' ',4' '-methylenedioxyphenyl)-8-oxo-3,7-dioxabicyclo[3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3' '-hydroxy-4' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (3), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4' '-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3' ',4' '-dimethoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Styraxlignolide C (2), styraxlignolide D (3), styraxlignolide E (4), and (-)-pinoresinol glucoside (8) exhibited weak radical-scavenging activity in the DPPH assay, with IC50 values of 380, 278, 194, and 260 microM, respectively.

Topics: 4-Butyrolactone; Antioxidants; Biphenyl Compounds; Furans; Glucosides; Glycosides; Korea; Lignans; Molecular Structure; Oleanolic Acid; Phenylpropionates; Picrates; Plant Bark; Plants, Medicinal; Stereoisomerism; Styrax

The antioxidant activities of Acanthopanax senticosus stems were evaluated in CCl4-intoxicated rats. The n-butanol fraction from the water extract of the stems, when pretreated orally at 200 mg/kg/day for 7 consecutive days in rats, was demonstrated to exhibit significant increases in antioxidant enzyme activities such as hepatic cytosolic superoxide dismutase, catalase and glutathione peroxidase by 30.31, 19.82 and 155%, respectively. The n-butanol fraction whereas showed a significant inhibition of serum GPT activity (65.79% inhibition) elevated with hepatic damage induced by CCl4-intoxication. Eleutheroside B, a lignan component, isolated from the n-butanol fraction was found to cause a moderate free radical scavenging effect on DPPH, its scavenging potency as indicated in IC50 value, being 58.5 microM. These results suggested that the stems of A. senticosus possess not only antioxidant but also hepatoprotective activities.

Topics: Administration, Oral; Alanine Transaminase; Animals; Antioxidants; Aspartate Aminotransferases; Biphenyl Compounds; Butanols; Carbon Tetrachloride Poisoning; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Eleutherococcus; Free Radical Scavengers; Glucosides; Hepatocytes; Indicators and Reagents; Lignans; Male; Phenylpropionates; Picrates; Plant Extracts; Plant Stems; Rats; Rats, Sprague-Dawley; Silymarin; Solubility; Water