• YAKHAK HOEJI
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• v.59 no.3
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• pp.120-126
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• 2015

Akebiae caulis have been used in folk medicines for diuretic, menstrual pain, and diuretic pain. It has been also resolved nephritis and cystitis. In this study, we isolated three phenolic compounds from 70% methanol extract using the open column chromatography. These isolated compounds which were 2-(3,4-dihydroxyphenyl)-ethyl-${\beta}$-D-glucopyranoside, 5-O-caffeoylquinic acid, and syringoylglycerol 2-O-${\beta}$-D-glucoside were determined by physico-chemical apparatus. Furthermore, we conducted DPPH and ABTS assay in order to screen the antioxidant activity of isolated three compounds. Also, we developed a rapidly HPLC-UV analysis method of two phenolic compounds (2-(3,4-dihydroxyphenyl)-ethyl-${\beta}$-D-glucopyranoside, 5-O-caffeoylquinic acid) for evaluating the Akebiae Caulis collected 30 samples from different regions. From the experiments, all three isolated compounds showed the significant antioxidant activity. We suggested that the content criteria of marker compounds were shown by a simple and rapid HPLC-UV method. The contents respectively were 0.009% (2-(3,4-dihydroxyphenyl)-ethyl-${\beta}$-D-glucopyranoside) and 0.036% (5-O-caffeoylquinic acid).

• Journal of the Korean Society of Food Science and Nutrition
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• v.41 no.10
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• pp.1417-1422
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• 2012

Alkyl glucosides were synthesized using the transglycosylation reaction of Celluclast, the cellulase from Trichoderma reesei, with cellobiose and various alcohols. Glucose as a by-product of the reaction was removed using the immobilized yeast system. Among the alkyl glucoside products, the acceptor products of methanol and ethanol were confirmed as methyl ${\beta}$-D-glucopyranoside and ethyl ${\beta}$-D-glucopyranoside via MALDI-TOF MS and enzymatic analysis. Optimal yields of methyl ${\beta}$-glucoside and ethyl ${\beta}$-glucoside were 65.3% (mol/mol) and 59.0% (mol/mol), respectively, based on cellobiose consumed.

• Food Science and Biotechnology
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• v.16 no.5
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• pp.854-857
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• 2007

In this study, the crude methanol extract of mulberry leaves was fractionated with chloroform, ethyl acetate, n-butanol, and water, successively. The antioxidant activities of the fractions were examined with the 2-deoxyribose oxidation and linoleic acid peroxidation methods. The ethyl acetate fraction showed the strongest antioxidant activity. From it we isolated chlorogenic acid, caffeic acid, quercetin $3-O-{\beta}-D-glucopyranoside$, and kaempferol $3-O-{\beta}-D-glucopyranoside$ with preparatory octadecyl silane-high performance liquid chromatography (ODS-HPLC), and identified the compounds by nuclear magnetic resonance (NMR) and fast atom bombardment mass (FAB-MS) analyses. Overall, quercetin $3-O-{\beta}-D-glucopyranoside$ showed the strongest antioxidant activity by both the 2-deoxyribose oxidation and rat liver microsome peroxidation methods.

• Bulletin of the Korean Chemical Society
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• v.32 no.5
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• pp.1721-1724
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• 2011

• Korean Journal of Pharmacognosy
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• v.30 no.4
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• pp.417-419
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• 1999

$Three\;compounds-ethyl-{\beta}-D-glucopyranoside$, 1,2,3,7-tetramethoxyxanthone, 1,7-dimethoxyxanthone-were isolated from roots of Polygala tenuifolia. The structures of these compounds were establised on the basis of spectral evidence including 2D NMR and HMBC studies. $Ethyl-{\beta}-D-glucopyranoside$ was isolated for the first time from Polygala genus and HMBC data of these compounds were first reported.

• Natural Product Sciences
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• v.20 no.2
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• pp.95-101
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• 2014

Five lignan glycosides, seven megastigmane glycosides, and seven phenolic compounds were isolated by repeated column chromatography from the MeOH extract of Salsola komarovii. Their structures were determined to be lariciresinol-9-O-${\beta}$-$\small{D}$-glucopyranoside (1), alangilignoside C (2), conicaoside (3), (+)-lyoniresinol 9'-O-${\beta}$-$\small{D}$-glucopyranoside (4), (8S,8'R,7'R)-9'-[(${\beta}$-glucopyranosyl)oxy]lyoniresinol (5), blumenyl B ${\beta}$-$\small{D}$-glucopyranoside (6), blumenyl A ${\beta}$-$\small{D}$-glucopyranoside (7), staphylionoside D (8), icariside $B_2$ (9), (6R,9S)-3-oxo-${\alpha}$-ionol ${\beta}$-$\small{D}$-glucopyranoside (10), 3-oxo-${\alpha}$-ionol 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (11), blumenol B 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (12), benzyl 6-O-${\beta}$-$\small{D}$-apiofuranosyl-${\beta}$-$\small{D}$-glucopyranoside (13), canthoside C (14), tachioside (15), isotachioside (16), biophenol 2 (17), 2-(3,4-dihydroxy)-phenyl-ethyl-${\beta}$-$\small{D}$-glucopyranoside (18), and cuneataside C (19) by spectroscopic methods. All the isolated compounds 1 - 19 were reported from this source for the first time. Compounds 2, 3 and 6 upregulated NGF secretion to $118.8{\pm}3.6%$, $128.2{\pm}9.3%$ and $111.1{\pm}7.1%$ without significant cell toxicity.

• Korean Journal of Pharmacognosy
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• v.44 no.1
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• pp.16-21
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• 2013

The fruits of Pourthiaea villosa were extracted with methanol and its extract was fractionated with n-hexane, methylene chloride, ethyl acetate and n-butanol. Repeated column chromatography of silica gel, sephadex LH-20 and HPLC led to the isolation of nine phenolic compounds from ethyl acetate soluble fraction. The chemical structures were elucidated as kaemferol-3-O-${\beta}$-D-glucopyranoside (astragalin) (1), isorhamnetin-3-O-${\beta}$-D-glucopyranoside (2), kaempferol-3-O-${\beta}$-D-xylopyranosyl($1{\rightarrow}2$)-${\alpha}$-L-rhamnopyranoside (3), caffeic acid (4), quercetin-3-O-${\beta}$-D-xylopyranosyl($1{\rightarrow}2$)-a-L-rhamnopyranoside (5), quercetin-3-O-${\beta}$-D-xylopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranoside (6), quercetin-3-O-${\beta}$-D-xylopyranosyl($1{\rightarrow}2$)-${\beta}$-D-galactopyranoside (7), quercetin-3-O-${\alpha}$-L-rhamnopyranoside (quercitrin) (8), and kaempferol-3-O-${\alpha}$-L-rhamnopyranoside (afzelin) (9) by spectroscopic techniques. These compounds were isolated from this plant for the first time.

• Journal of the Korean Wood Science and Technology
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• v.34 no.3
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• pp.73-83
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• 2006

The dried needles (1.5 kg) of Abies koreana and Abies holophylla were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$, $^{13}C-NMR$, COSY, HETCOR, FAB and EI-MS. The needles of Abies koreana and Abies holophylla contained a large amount of aromadendrin-7-O-${\beta}$-D-glucopyranoside (compound III), polydatin (compound VI), (-)-rhododendrol-2-O-${\beta}$-D-glucopyranoside (compound VII), in addition to a small amount of (+)-catechin (compound I), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound IV), myricetin-3-O-${\beta}$-D-glucopyranoside (compound V), naringenin-7-O-${\beta}$-D-glucopyranoside (compound II). DPPH analysis was also tested to investigate the antioxidative effects on the isolated compounds and (+)-catechin and polydatin were effective.

• Journal of the Korean Chemical Society
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• v.47 no.1
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• pp.43-46
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• 2003

From Portulaca oleracea which is widely distributed in Korea and has long been used as a folk medicine, two biophenolic glycosides, 3-hydroxy-1-(2-hydroxyethyl)phenyl-4-O-${\beta}$-D-glucopyranoside (1) and 2-(3,4-dihydroxyphenyl) ethyl-O-${\beta}$-D-glucopyranoside (2) were isolated using column chromatography and reversed-phase HPLC. $^{13}C$ NMR spectral assignment for these compounds was revised by the extensive 2-D NMR experiments such as NOESY, HMQC, and HMBC. These compounds showed a considerable antioxidant effect in DPPH assay system.

• Archives of Pharmacal Research
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• v.28 no.9
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• pp.1031-1036
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• 2005

[ $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ ] (1) was isolated from an ethyl acetate extract of the root bark from Lycium chinense Miller, and its structure was determined using 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC. $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ exhibited potent antimicrobial activity against antibiotic-resistant bacterial strains, methicillin-resistant Staphylococcus aureus (MRSA) isolated from patients, and human pathogenic fungi without having any hemolytic effect on human erythrocytes. In particular, compound 1 induced the accumulation of intracellular trehalose on C. albicans as stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae caused by the pathogenesis. This indicates that $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ has excellent potential as a lead compound for the development of antibiotic agents.