• 생약학회지
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• 제36권4호통권143호
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• pp.282-290
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• 2005

The MeOH extract of the the leaves of Salix hallaisanensis (Salicaceae) was partitioned successively with $CHCl_3$, 20% MeOH, 40% MeOH and 60% MeOH solution. From the fractions obtained, 9 compounds were isolated, $diosmetin-7-O-{\beta}-d-glucoside$ (I), $diosmetin-7-O-{\beta}-D-glucosyl-(1{\rightarrow)6)-{\beta}-d-glucoside$ (II), $diosmetin-7-O-{\beta}-d-xylosyl-(1{\rightarrow}6)-{\beta}-D-glucoside$ (III), $quercetin-3-O-{\beta}-d-galactoside$ (hyperoside) (IV), $quercetin-3-O-{\alpha}-l-rhamnosyl-(1{\rightarrow}6)-{\beta}-D-glucoside(rutin)$ (V), luteolin (VI), $luteolin-7-O-{\beta}-d-glucoside$ (VII), $kaempferol-3-O-{\alpha}-l-rhamnosyl-(1{\rightarrow}6)-{\beta}-D-glucoside$ (VIII), and (+)-catechin (IX).

• 약학회지
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• 제41권4호
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• pp.444-449
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• 1997

Five flavonoids were isolated from the heartwoods of Maackia fauriei. On the basis of spectroscopic evidences, the structure of these compounds were established as (-)maa ckiain(3-hydroxy-8,9-methylenedioxypterocarpan), ononin(4'-methoxyisoflavone- 7-O-${\beta}$-D-glucoside), wistin(4',6-dimethoxyisoflavone-7-O-${\beta}$-D-glucoside), daidzin(4'-hydroxyisoflavone-7-O-${\beta}$-D-glucoside) and 2'-methoxy-4'- hydroxyisoflavone-6-O-${\beta}$-D-glucoside. In these compounds, 2'-methoxy-4'-hydroxyisoflavone-6-O-${\beta}$-D-glucoside was for the first time isolated from the plant source.

• 한국식품영양과학회지
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• 제29권1호
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• pp.106-110
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• 2000

We investigated the active oxygen scavenging activity and active compound from Humulus japonicus. The ethyl acetate and butanol fraction exhibited strong scavenging effects on hydroxyl radical. Furthermore active compound was isolated and purified using Amberlite XAD-2 column chromatography and preparative HPLC from ethyl acetate fracton, and major compound was identified as a luteolin-7-O-$\beta$-D-glucoside by the MS, UV, 1H-NMR and 13C-NMR analyses. Luteolin-7-O-$\beta$-D-glucoside exhibited strong scavenging effect on active oxygens such as superoxide radical, hydroxyl radical and hydrogen peroxide.

• Molecules and Cells
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• 제37권2호
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• pp.172-177
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• 2014

A glycosyltransferase, YjiC, from Bacillus licheniformis has been used for the modification of the commercially available isoflavonoids genistein, daidzein, biochanin A and formononetin. The in vitro glycosylation reaction, using UDP-${\alpha}$-D-glucose as a donor for the glucose moiety and aforementioned four acceptor molecules, showed the prominent glycosylation at 4' and 7 hydroxyl groups, but not at the $5^{th}$ hydroxyl group of the A-ring, resulting in the production of genistein 4'-O-${\beta}$-D-glucoside, genistein 7-O-${\beta}$-D-glucoside (genistin), genistein 4',7-O-${\beta}$-D-diglucoside, biochanin A-7-O-${\beta}$-D-glucoside (sissotrin), daidzein 4'-O-${\beta}$-D-glucoside, daidzein 7-O-${\beta}$-D-glucoside (daidzin), daidzein 4', 7-O-${\beta}$-D-diglucoside, and formononetin 7-O-${\beta}$-D-glucoside (ononin). The structures of all the products were elucidated using high performance liquid chromatography-photo diode array and high resolution quadrupole time-of-flight electrospray ionization mass spectrometry (HR QTOF-ESI/MS) analysis, and were compared with commercially available standard compounds. Significantly higher bioconversion rates of all four isoflavonoids was observed in both in vitro as well as in vivo bioconversion reactions. The in vivo fermentation of the isoflavonoids by applying engineered E. coli $BL21(DE3)/{\Delta}pgi{\Delta}zwf{\Delta}ushA$ overexpressing phosphoglucomutase (pgm) and glucose 1-phosphate uridyltransferase (galU), along with YjiC, found more than 60% average conversion of $200{\mu}M$ of supplemented isoflavonoids, without any additional UDP-${\alpha}$-D-glucose added in fermentation medium, which could be very beneficial to large scale industrial production of isoflavonoid glucosides.

• Natural Product Sciences
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• 제12권2호
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• pp.89-93
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• 2006

One new sterol glucoside, $gomphsterol\;{\beta}-D-glucoside$ 1 along with known compounds, ${\beta}-sitosterol$, stigmasterol, campesterol, $stigmasterol-{\beta}-D-glucoside$, friedelin, 3-epi-friedelinol, allantoin, and $chrysoeriol-7-O-{\beta}-D-glucoside$ have been isolated from the aerial parts of Gomphrena globosa (Amaranthaceae). On the basis of spectroscopic (including 2D NMR) and chemical studies, the structure of 1 was elucidated as $(22E,24S)-24-ethylcholesta-7,9(11),22-trien-3{\beta}-ol-3-O-{\beta}-D-glucopyranoside$. Known compounds are reported for the first time from this plant species.

• Applied Biological Chemistry
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• 제42권2호
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• pp.162-165
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• 1999

Spraque-Dawley계 수컷랫트에 단풍취로부터 분리한 화합물을 경구투여하고 혈청 ethanol농도와 간의 ADH 활성에 미치는 효과를 검토한 결과 알코올대사를 촉진시키는 성분은 apigenin $7-O-{\beta}-D-glucoside$로 확인되었다.

• Natural Product Sciences
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• 제14권2호
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• pp.131-137
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• 2008

From the 70% EtOH extract of the roots of Astragalus membranaceus (Leguminosae), eleven flavonoid derivatives and a lignan, were isolated and identified as liquiritigenin (1), daidzein (2), formononetin (3), sophorophenolone (4), calycosin (5), methylnissolin (6), isomucronulatol (7), isomucronulatol 7-O-glucoside (8), methylnissolin 3-O-glucoside (9), calycosin 7-O-glucoside (10), (+)-syringaresinol O-${\beta}$-D-glucoside (11), and isomucronulatol 7,2'-di-O-glucoside (12), by spectroscopic methods. This is the second report of the isoflavonoid derivatives sophorophenolone (4) and isomucronulatol 7,2'-di-O-glucoside (12) from a natural source, as well as the first report of compounds liquiritigenin (1), daidzein (2) and (+)-syringaresinol O-${\beta}$-D-glucoside (11) from the species A. membranaceus.

• Natural Product Sciences
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• 제20권3호
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• pp.211-215
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• 2014

Opuntia humifusa, also called as Cheonnyuncho, is a cactus widely cultivated in southern regions of Korea. It has been known to have diverse biological activities, but most of the studies were performed with the MeOH extracts or solvent-partitioned fractions. Furthermore, the efforts to identify the responsible compounds for the biological activities are very limited. In this study, we tested the inhibitory effect of extracts and solvent-partitioned fractions of O. humifusa against LPS-induced nitric oxide (NO) production in Raw264.7 cells. The butanol fractions of O. humifusa efficiently inhibited the production of NO in Raw264.7 cells, but it was not due to the reduction of cell viability. Bioassay-guided isolation of butanol fractions of O. humifusa allowed the isolation of three flavonoids isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1), isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) and isorhamnetin 3-O-${\beta}$-$\small{D}$-(6-O-${\alpha}$-$\small{L}$-rhamnosyl)glucoside (3), and one lignan syringaresinol O-${\beta}$-$\small{D}$-glucopyranoside (4). Among them, isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1) and isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) exhibited the moderate inhibitory effects against LPS-induced NO production. This is the first time to report anti-inflammatory effects of these compounds.

• Archives of Pharmacal Research
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• 제25권3호
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• pp.313-319
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• 2002

A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

• 생약학회지
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• 제47권4호
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• pp.295-300
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• 2016

Flavonoids are widely reported to be beneficial to human health. Among flavonoids, in general, flavonoid aglycons have better biological activities than flavonoid glycosides, in that aglycons can easily penetrate through cell membrane because of their low polarity. Therefore, kaempferol, quercetin and various their glycosides were evaluated for their abilities to inhibit NO and $PGE_2$ productions in LPS-induced RAW 264.7 cells. Of these flavonoids and flavonoid glycosides, kaempferol-7-O-${\beta}$-D-glucoside(kp-7-glu) which possesses a glycoside at C-7 position of the A ring in kaempferol, potently inhibited NO, $PGE_2$ and $TNF-{\alpha}$, $IL-1{\beta}$, IL-6 productions in LPS-induced RAW 264.7 macrophages.