• Journal of the Korean Wood Science and Technology
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• v.31 no.6
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• pp.8-14
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• 2003

This study was carried out identify extractives of Amorpha fruticosa. In this study, one flavonoid glycoside, one ester and two rotenoids were isolated from fruits of A. fruticosa. The structures were determined as: kaempferol 7-O-α-L-rhamnopyranoside (I), methyl 3, 4, 5-trihydroxybenzoate (methyl gallate, II), tephrosin (III) and dalbinol (IV), respectively, on the basis of spectroscopic data.

• Korean Journal of Pharmacognosy
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• v.43 no.3
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• pp.206-212
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• 2012

Ten flavonol glycosides were isolated from the EtOAc fraction of the MeOH extract of Metaplexis japonica Makino. Structures of the flavonoids were elucidated on the basis of spectroscopic data and comparison with literature values. The flavonoids were found to be mostly common flavonol 3-glycosides. It is of interest that the sacchaide parts of the isolates were pairs of arabinosides, glucosides, galactosides, rutinosides and robinobiosides of kaempferol and quercetin. All of these compounds were isolated for the first time from this plant.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2018.04a
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• pp.13-13
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• 2018

The anti-inflammatory (INF) compounds (1-15) were isolated from Agrimonia pilosa Ledeb. (APL) by activity-guided isolation technique. The isolated compounds (1-15) were identified as quercetin-7-O-rhanmoside (1), apigenin-7-O-glycoside (2), kaempferol-7-O-glycoside (3), apigenin-7-O-[6"-(butyl)-glycoside] (4), querceitn (5), kaempferol (6), apigenin (7), apigenin-7-O-[6"-(pentyl)-glycoside] (8), agrimonolide (9), agrimonolide-6-O-glucoside (10), desmethylagrimonolide (11), desmethylagrimonolide-6-O-glucoside (12), luteolin (13), vitexin (14) and isovitexin (15). Flavonoids, compound 2, 3, 11, and 14-15 have been found in APL for the first time. Furthermore, two novel flavone derivatives, compound 4 and 8, have been isolated inceptively in plant. In the no cytotoxicity concentration ranges of $0-20{\mu}M$, nitric oxide (NO) production level of 1-15 was estimated in LPS-treated Raw 264.7 macrophage cells. The flavone aglycones, 7 (apigenin, $IC_{50}=3.69{\pm}0.34{\mu}M$), 13 (luteolin, $IC_{50}=4.62{\pm}0.43{\mu}M$), 6 (kaempferol, $IC_{50}=14.43{\pm}0.23{\mu}M$) and 5 (quercetin, $IC_{50}=19.50{\pm}1.71{\mu}M$), exhibited excellent NO inhibitory (NOI) activity in dose-dependent manner. In the structure activity relationship (SAR) study of apigenin-derivatives (APD), apigenin; Api, apigenin-7-O-glucoside; Api-G, apignenin-7-O-[6"-(butyl)-glycoside]; Api-BG and apignenin-7-O-[6"-(pentyl)-glycoside]; Api-P, from APL on INF activity was investigated. The INF mediators level such as NO, INF-cytokines, NF-KB proteins, iNOS and COX-2 were sharply increased in Raw 264.7 cells by LPS. When pretreatment with APD in INF induced macrophages, NOI activity of Api was most effective than other APD with $IC_{50}$ values of $3.69{\pm}0.77{\mu}M$. And the NOI activity was declined in the following order: Api-BG ($IC_{50}=8.91{\pm}1.18{\mu}M$), Api-PG ($IC_{50}=13.52{\pm}0.85{\mu}M$) and API-G ($IC_{50}=17.30{\pm}0.66{\mu}M$). The NOI activity of two novel compounds, Api-PG and Api-BG were lower than their aglycone; Api, but more effective than Api-G (NOI: Api-PG and Api-BG). And their suppression ability on INF cytokines such as $TNF-{\alpha}$, $IL-1{\beta}$ and IL-6 mRNA showed the similar tendency. Therefore, the anti-INF mechanism study of Api-PG and Api-BG on nuclear factor-kappa B ($NF-{\kappa}B$) pathway, representative INF mechanism, was investigated and Api was used as positive control. Api-BF was more effectively prevent the than phosphorylation of $pI{\kappa}B$ kinase (p-IKK) and p65 than Api-PG in Raw 264.7 cells. In contrast, Api-PG and Api-BG were not reduced the phosphorylation of inhibitor of kappa B alpha ($I{\kappa}B{\alpha}$). Moreover, pretreatment with Api-PG and Api-BG, dose-dependently inhibited LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNAs and proteins in macrophage cells, and their expression were correlated with their NOI activity. Therefore, APL can be utilized to health promote agent associated with their AIN metabolites.

• Journal of Life Science
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• v.16 no.3 s.76
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• pp.442-446
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• 2006

Cedrela sinensis is a broadleaf tree that is widely cultivated in Korea and China. It was used for treating enteritis, dysentery, and skin itch in oriental medicine. In this study, three major flavonoids, kaempferol-3-O-rhamnoside (1), quercetin-3-O-rhamnoside (2), and quercetin-3-O-glucoside (3), were isolated from the leaf of Cedrela sinensis. The biological activities of these compounds were tested by inhibitory activity of matrix metalloproteinases-2 (Type IV collagenase) method together with a cytotoxicity and a apoptosis test against human cancer cell lines.

• Korean Journal of Plant Taxonomy
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• v.41 no.1
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• pp.10-15
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• 2011

Fifteen populations comprising three taxa and a putative hybrid of Fallopia sect. Reynoutria in Korea were examined for their leaf flavonoid constituents. Nineteen flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols quercetin and kaempferol, and of the flavones apigenin and luteolin. Among them, quercetin 3-O-galactoside and quercetin 3-O-glucoside were major flavonoid constituents, and present in all taxa. The flavonoid data appear to be very useful for taxon delimitation, and all taxa examined are readily distinguished by their flavonoid profiles. In addition, the flavonoid data suggest that the Nonsan population may be of hybrid origin involving F. japonica var. japonica, F. forbesii, and F. sachalinensis. In F. japonica var. japonica, there is no apparent correlation between their levels of polyploidy and flavonoid chemistry, but geographical variation of the flavonoid profiles among some populations was detected.

• YAKHAK HOEJI
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• v.40 no.4
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• pp.394-399
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• 1996

As a series of the studies on the specific and indigenous plants of Mt. Halla, the constituents from stem of Rhamnus taquetii (Rhamnaceae) were investigated. From the water fraction of the MeOH extract, a new flavonol glycoside, kaempferide-3-O-${\alpha}$-L-rhamnopyranosyl(1->3)-${\alpha}$-L-rhamnopyranosyl(1-6)-${\beta}$-D-galactopyranoside, was isolated with three known compounds, quercetin, quercetin-3-methylether, kaempferol, by column chromatographic separation using Amberlite XAD-2, ODS-gel and Sephadex LH-20 and elucidated physico-chemical evidences($^1H-NMR,\;^{13}C-NMR$,IR, EI-Mass, FAB-Mass, and G.C.),respectively.

• Archives of Pharmacal Research
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• v.27 no.7
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• pp.751-756
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• 2004

Flavonoids have been demonstrated to exhibit a wide range of biological activities including anti-inflammatory and neuroprotective actions. Although a significant amount of flavonoids has been identified to be present as glycosides in medicinal plants, determinations of the biological activities of flavonoids were mainly carried out with aglycones of flavonoids. Therefore, the exact role of the glycosidation of flavonoid aglycones needs to be established. In an attempt to understand the possible role of glycosidation on the modulation of the biological activities of flavonoids, diverse glycosides of kaempferol, quercetin, and aromadendrin were examined in terms of their anti-inflammatory activity determined with the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglial cells. The results indicated that glycosidation of aglycones attenuated the suppressive activity of aglycones on LPS-induced NO production. Although attenuated, some of glycosides, depending on the position and degree of glycosidation, maintained the inhibitory capability of LPS-induced NO production. These findings suggest that glycosidation of flavonoid aglycones should be considered as an important modulator of the biological activities of flavonoids.

• Natural Product Sciences
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• v.16 no.4
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• pp.217-222
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• 2010

A phytochemical investigation of the ethanolic extract of Erythrina caffra flowers from an Egyptian origin yielded three C-flavonoidal glycosides; 5,7,4'-trihydroxyflavone-8-C-$\beta$-D-glucopyranoside (vitexin) (1), 5,7,4'-trihydroxyflavone-6-C-$\beta$-D-glucopyranosyl-(1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (isovitexin-2"-$\beta$-D-glucopyranoside) (2), 5, 7, 4'-trihydroxyflavone-6, 8-di-C-$\beta$-D-glucopyranoside (vicenin-2) (3) and one O-flavonoidal glycoside; kaempferol-3-O-$\beta$-D.glucopyranosyl) (1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (4). The structures of the isolated compounds (1 - 4) were elucidated using different spectral techniques (UV, 1D and 2D NMR and HRESIMS). This is the first report for the isolation of flavonoidal glycosides from Erythrina caffra. The antibacterial, antifungal, antimalarial, and antileishmanial activities of the isolates were evaluated. In addition, the cytotoxic activity of the ethanolic extract and the main fractions were tested using brine shrimp bioassay.

• 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.