• 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.

• YAKHAK HOEJI
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• v.58 no.5
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• pp.314-321
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• 2014

Cibotii Rhizoma, the dried rhizome of Cibotium barometz J. Smith (C. barometz), has long been used to treat bone or nervous system disorders. In this regard, we isolated three main phenolic compounds, onitin-4-O-${\beta}$-D-glucopyranoside (1), irisdichototins E & F epimeric mixture (2), and protocatechuic acid (3) from C. barometz methanol extract. In addition, we screened their antioxidative activities by DPPH, ABTS radical, and superoxide scavenging assays. Among these three compounds, irisdichototins E & F and protocatechuic acid showed strong antioxidant activities. Also, the antioxidant activities of the C. barometz extracts were proportional to the contents of irisdichototins E & F and protocatechuic acid, thus these two phenolic compounds could be main active compounds of C. barometz. In addition, onitin-4-O-${\beta}$-D-glucopyranoside is considered as a marker compound of C. barometz because this compound is specifically contained in C. barometz which belongs to Pteridophyta order. A rapid analysis method for the simultaneous determination of phenolic compounds was also developed by UPLC (Ultra Performance Liquid Chromatography). Using the developed method, the two active compounds (irisdichototins E & F and protocatechuic acid) and a marker compound (onitin-4-O-${\beta}$-D-glucopyranoside) were successfully quantified in 14 commercial samples that were collected from different regions.

• Natural Product Sciences
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• v.24 no.4
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• pp.259-265
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• 2018

The three flavone glycosides, 4'-O-methylisoscutellarein 7-O-(6'''-O-acetyl)-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (1), isoscutellarein 7-O-(6'''-O-acetyl)-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (3), and isoscutellarein 7-O-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (4) in addition to a flavonol glycoside, kaempferol 3-O-${\beta}$-D-glucopyranoside (astragalin, 2), were isolated from Stachys japonica (Lamiaceae). In cholinesterase inhibition assay, compound 1 significantly inhibited aceylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities ($IC_{50}s$, $39.94{\mu}g/ml$ for AChE and $86.98{\mu}g/ml$ for BChE). The content of isolated compounds were evaluated in this plant extract by HPLC analysis. Our experimental results suggest that the flavonoid glycosides of S. japonica could prevent the memory impairment of Alzheimer's disease.

• Archives of Pharmacal Research
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• v.27 no.4
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• pp.390-395
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• 2004

The methanol extract obtained from the aerial parts of Aceriphyllum rossii (Saxifragaceae) was fractionated into ethyl acetate (EtOAc), n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded six flavonol glycosides. They were identified as kaempferol 3-O-$\beta$-D-glucopyranoside (astragalin, 1), quercetin 3-O-$\beta$-D-glucopyranoside (isoquercitrin, 2), kaempferol 3-O-$\alpha$-L-rhamnopyranosyl $(1{\to}6)-\beta$-D-glucopyranoside (3), quercetin 3-O$\alpha$-L-rharnnopyranosyl $(1{\to}6)-\beta$-D-qlucopyrano-side (rutin, 4), kaempferol 3-O-[$\alpha$-L-rharnnopyranosyl $(1{\to}4)-\alpha$-L-rhamnopyranosyl $(1{\to}6)-\beta$-D-glucopyranoside] (5) and quercetin 3-O-[$\alpha$-L-rhamnopyranosyl $(1{\to}4)\alpha$-L-rhamnopyranosyl $(1{\to}6)\beta$-D-glucopyranoside] (6) on the basis of several spectral data. The antioxidant activity of the six compounds was investigated using two free radicals such as the ABTS free radical and superoxide anion radical. Compound 1 exhibited the highest antioxidant activity in the ABTS $\{2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)\}$ radical scavenging method. 100 mg/L of compound 1 was equivalent to $72.1\pm1.4\;mg/L$ of vitamin C, and those of compounds 3 and 5 were equivalent to $62.7\pm0.5\;mg/L$ and $54.3\pm1.3\;mg/L$ of vitamin C, respectively. And in the superoxide anion radical scavenging method, compound 5 exhibited the highest activity with an $IC_{50}$ value of $17.6{\pm}0.3{\mu}M$. In addition, some physical and spectral data of the flavonoids were confirmed.

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.865-872
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• 2002

In the course of the investigations of natural antioxidants, we examined the antioxidant activities of the methanol (MeOH) extracts of some selected Prunus species, including P. buergeriana, P. davidiana, P padus, P. pendula for. ascendens, P. sargentii, P. serrulata var. spontanea and P. yedoensis by three methods as represented by the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical, total ROS (reactive oxygen species) and the peroxynitrite ($ONOO^-$) scavenging activity tests. We also evaluated the activities of the organic solvent-soluble fractions, including the dichloromethane ($CH_2Cl_2$), ethyl acetate (EtOAc), n-butanol (n-BuOH) fractions and the water ($H_2O$) layer of P. serrulata var. spontanea leaves. By means of bioassay-directed fractionation, we isolated eleven known flavonoids (1-11) from the EtOAc soluble fraction of the MeOH extract of the Prunus serrulata var. spontanea leaves, exhibiting strong antioxidant activity and characterized as prunetin (1), genistein (2), quercetin (3), prunetin $4'-O-{\beta}-glucopyranoside$ (4), kaempferol $3-O-{\alpha}-arabinofuranoside$ (5), prunetin $5-O-{\beta}-glucopyranoside$ (6), kaempferol $3-O-{\beta}-xylopyranoside$ (7), genistin (8), kaempferol $3-O-{\beta}-glucopyranoside$ (9), quercetin $3-O-{\beta}-glucopyranoside$ (10) and kaempferol $3-O-{\beta}-xylopyranosyl-(1{\rightarrow}2)-{\beta}-glucopyranoside$ (11). Compounds 3 and 10 showed good activities in all tested model systems. Compounds 2 and 8 showed scavenging activities in the DPPH and $ONOO^-$ tests, while compounds 5, 7, 9 and 11 were active in the $ONOO^-$ and ROS tests. On the other hand, compounds 1, 4 and 6 did not show any activities in the tested model systems.

• Preventive Nutrition and Food Science
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• v.10 no.1
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• pp.1-5
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• 2005

Eight flavonoids, apigenin-6-C-β-D-glucopyranosy l-8-C-β-D-glucopyranoside (AGG), quercetin 7-O-β-D­glucopyranoside (QG), luteolin 7-O-β-D-glucopyranoside (LG), quercetin 7-O-(6'-O-acetyl)-β-D-glucopyranoside (QAG), luteolin 7-O-(6'-O-acetyl)-β-D-glucopyranoside(LAG), quercetin (Q), luteolin (L) and acacetin 7-O-β­D-glucuronide (AG) were determined by HPLC in the safflower (Carthamus tinctorius L.) leaf during growth and processing. During growth, levels of five flavonoid glycosides (AGG, QG, LG, QAG, & LAG) in the leaf increased progressively at over time according to growth stages, reached a maximum before June 11, and then decreased sharply, while those of three flavonoid aglycones (Q, L, & AG) increased greatly at the early stage of growth, reached a peak before May 28, and then decreased rapidly. During the steaming process, contents of five flavonoid glycosides increased rapidly with increased steaming time, reached a maximum after 5 min of steaming, and then decreased, whereas those of flavonoid aglycones except for AG decreased sharply with increased steaming time. During the roasting process, contents of three flavonoid glycosides decreased rapidly with increased roasting time, whereas those of two acetylflavonoid glycosides (QAG & LAG) and three flavonoid aglycones increased progressively with increased roasting time, reached a maximum after 3 min of roasting, and then decreased. These results suggest that appropriate steamed and roasted safflower leaves are a rich source of flavonoids, and may be a good source of bioactive components as a functional leaf tea.

• YAKHAK HOEJI
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• v.51 no.2
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• pp.88-95
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• 2007

Atractylodes macrocephala has been used for renal anorexia, gastroenteritis, cold, dyspepsia in Korean folk medicine. Specially aerial parts has been eaten as edible mountain herbs. In order to investigate the efficacy of antioxidant activity the activity guided fractionation and isolation of physiologically active substance were peformed. For the investigation of the active components from Atractylodes macrocephala MeOH extracts of aerial parts of Atractylodes macrocephala Koidzumi L. were suspended with H$_2$O, partitioned by CHCl$_3$. In order to investigate the efficacy of antioxidative activity the activity guided fractionation and isolation of physiologically active substance were peformed. CHCl$_3$, H$_2$O, 30% MeOH, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method. It was revealed that 30% MeOH and 60% MeOH fractions have significantly antioxidant activity. From 30% MeOH and 60% MeOH fraction, six flavonoids (7-methoxy-pinocembrin-7-O-${\beta}$-D-glucopyranoside, apige nin-8-C-${\beta}$-D-glucopyranoside, 4'-caffeoyl-luteolin-6-glucopyranoside, luteloin-6-C-${\beta}$-D-glucopyranoside, apigenin-6-C-${\beta}$-D-glucopyranoside, luteolin) and four phenylpropanoids (3-feruloylquinic acid, 4,5-di-O-caffeoylquinic acid, feruloyl acid, 3,5-di-O-caffeoylquinic acid) were isolated. To investigate the antioxidant activities of each compounds, we measured radical scavening activity with DPPH method and anti-lipid peroxidative efficacy on low density lipoprotein (LDL) with TBARS assay. Six compounds (III, IV, V, VI, IX, X) which have antioxidant factor showed significant activities.

• Natural Product Sciences
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• v.11 no.1
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• pp.41-44
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• 2005

Chemical investigation of the aerial parts of Chloranthus japonicus Sieb. led to the isolation a new compound, 9-hydroxy heterogorgiolide (1) and $isofraxidin-7-O-{\beta}-D-glucopyranoside$ (2), the isolation of which is reported for the first time from this plant, along with the known components, ${\beta}-sitosterol,\;{\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$, palmitic acid and octacosanoic acid. The structures of compound 1 and 2 were determined on the basis of spectroscopic data including two dimensional NMR and high resolution MS.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.45 no.2
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• pp.83-87
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• 2000

The five phenolic compounds of peony root were isolated by Sephadex LH-20 column chromatography. Their chemical structures were identified by spectroscopic methods (UV, FT-IR, FAB-MS and $^1H$ .&^13C$-NMR). The complete structures of these compounds were elucidated to be (+)-taxifolin-3-0-$\beta$-D-glucopyranoside, benzoic acid, gallic acid, (-)-epicatechin and (+)-catechin. The concentrations of five phenolic compounds in the peony root of three Korean cultivars (Youngchonjakyak, Euisungjakyak and Jomjakyak) were determined by reverse-phase HPLC. The constituents concentration in Youngchonjakyak were generally higher than in Euisungjakyak and Jomjakyak. The concentrations of (+)-taxifolin-3-O-$\beta$-D-glucopyranoside, benzoic acid, gallic acid, (-)-epicatechin and (+)-catechin in three different cultivars were ranged 0.23-0.52%, 0.20-0.30%, 0.26-0.28%, 0.09-0.12% and 0.34-0.63%, respectively.

• 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.