• 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.

• Food Science and Biotechnology
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• v.17 no.5
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• pp.1060-1065
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• 2008

A novel benzoyl glucoside (4) and 13 known phenolic compounds were isolated from the leaves of Camellia japonica by a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The structure of 4 was determined to be 4-hydroxy-2-methoxyphenol 1-O-$\beta$-D-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (camelliadiphenoside). The 13 known compounds were identified as (E)-coniferyl alcohol (1), (-)-epicatechin (2), 4-hydroxyphenol 1-O-$\beta$-D-(6-O-p-hydroxybenzoyl) glucopyranoside (3), naringenin 7-O-$\beta$-D-glucopyranoside (5), quercetin 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (6), kaempferol 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (7), (+)-catechin (8), 1,6-di-O-p-hydroxybenzoyl-$\beta$-D-glucopyranoside (9), phloretin 2'-O-$\beta$-D-glucopyranoside (10), quercetin 3-O-$\beta$-D-glucopyranoside (11), quercetin 3-O-$\beta$-D-galactopyranoside (12), kaempferol 3-O-$\beta$-D-galactopyranoside (13), and kaempferol 3-O-$\beta$-D-glucopyranoside (14). Their chemical structures were determined by the spectroscopic data of fast atom bondardment mass spectrometry (FABMS) and nuclear magnetic resonance (NMR). Flavonoids having the catechol moiety showed significantly higher DPPH radical scavenging activity than other isolated compounds having monohydroxy phenyl group.

• Korean Journal of Environment and Ecology
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• v.28 no.5
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• pp.574-587
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• 2014

In this study, vertical distribution patterns of Quercus mongolica Fisch. ex Ledeb. and Q. serrata Murray in Korea were recognized and possibility of introgressive hybridization and gene flow between Q. mongolica and Q. serrata in Mt. Jiri was inferred by flavonoid analyses. The most critical factor on distribution patterns was the altitude in accordance with temperature condition. A zonal distribution was recognized: Quercus mongolica zone in the upper area and Q. serrata zone in the lower area. In Central Korea, the range of vertical distribution of Q. mongolica was above alt. 100m, almost everywhere, whereas that of Q. serrata was from alt. 0 m to alt. 500(-700) m, and the species is rare above that altitude. But in Southern Korea, Q. serrata is found up to above alt. 1,000 m, whereas frequency of Q. mongolica reduces as elevation in decline and the species is rare below alt. 300 m, even though pure stands being formed on higher mountain slope. Altitudinal distribution of the two species, however, overlaps, where the two species occur together. Thirty-seven individuals of Q. mongolica and Q. serrata in Mt. Jiri and other area were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols kaempferol, quercetin, isorhamnetin, myricetin, and four compounds among the flavonoid compounds were acylated. Kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside and its acylated compounds were major constituents and present in all individuals. Quercus mongolica is distinguished from Q. serrata by the presence of quercetin 3-O-arabinosylglucoside and by high concentration of three acylated compounds, acylated kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside, and by relatively low concentration or lacking of rhamnosyl flavonol compounds. There are intraspecific variations in flavonoid profiles for Q. mongolica and Q. serrata, the flavonoid profiles for individuals of two species in hybrid zone (sympatric zone) tend to be similar to each other, qualitatively and quantitatively. These findings strongly suggest that gene exchange or gene flow occurs through the introgressive hybridization between Q. mongolica and Q. serrata in Mt. Jiri. Therefore, Quercus crispula, occupying morphologically intermediate position between Q. mongolica and Q. serrata, is suspected of being a hybrid taxon of two putative parental species.

• Journal of Life Science
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• v.24 no.10
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• pp.1092-1101
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• 2014

In this study, the distribution patterns of Quercus mongolica and Q. serrata in Korea were investigated, and the possibility of introgressive hybridization and gene flow between Q. mongolica and Q. serrata in Mt. Seorak was inferred by flavonoid analyses. The most critical factor in the vertical and horizontal distribution patterns of Q. mongolica and Q. serrata was the temperature, in accordance with latitude and altitude. The species showed a zonal distribution, with a Q. mongolica zone in the upper area and a Q. serrata zone in the lower area. In Mt. Seorak, Central Korea, the range of the vertical distribution of Q. mongolica was generally above an altitude of 100 m, whereas that of Q. serrata was an altitude of 0-400 m (-500) and rarely above an altitude of 500 m. However, in Mt. Jiri, Southern Korea, Q. serrata was found up to an altitude of 1,000~1,200 m, whereas the frequency of Q. mongolica was reduced at lower elevations and the species was rare below an altitude of 300 m, although pure stands were found on higher mountain slopes above an altitude of 1,200 m. The altitudinal distribution of the two species overlapped, where the two species occurred together. The leaf flavonoid constituents of thirty-four individuals of Q. mongolica and Q. serrata in Mt. Seorak and Mt. Jiri, Korea were examined. Twenty-four flavonoid compounds were isolated and identified. These were glycosylated derivatives of flavonols kaempferol, quercetin, isorhamnetin, myricetin. Five compounds among the flavonoid compounds were acylated. Kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside, and its acylated compounds were major constituents and present in all individuals. Quercus mongolica is distinguished from Q. serrata by the presence of quercetin 3-O-arabinosylglucoside, a high concentration of three acylated compounds (kaempferol 3-O-glucoside, quercetin 3-O-glucoside, and quercetin 3-O-galactoside), and a relatively low concentration or lack of rhamnosyl flavonol compounds. Intraspecific variations, however, were found in the flavonoid profiles of Q. mongolica and Q. serrata, and the flavonoid profiles of individuals belonging to the two species in a hybrid zone (sympatric zone) tended to be similar, qualitatively and quantitatively. These findings strongly suggest that gene exchange or gene flow occurs through introgressive hybridization between Q. mongolica and Q. serrata in Mt. Seorak.

• Archives of Pharmacal Research
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• v.27 no.1
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• pp.40-43
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• 2004

All ten compounds were isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as three iridoid glycosides, asperuloside, geniposidic acid and asperulosidic acid, a coumarin glycoside, scopolin, and six flavonoids, rutin, kaempferol-3-0-rutinoside, quercitrin, astragalin, isoquercitrin and quercetin by spectroscopic analysis.

• Horticultural Science & Technology
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• v.28 no.6
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• pp.921-927
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• 2010

The objective of this study was to improve the breeding efficiency and consumption of red onion by analysis of chemical components. The red cultivar S&P5294 ($52.9mg{\cdot}g^{-1}$ F.W.) resulted in the highest sugar content, and sweetness whereas 'Redprime' had the lowest. For the pyruvic acid content the cultivar 'Redsun' showed the highest value, followed by 'Sunpower' (yellow onion) and S&P7270. Breeding lines had higher sugar content and sweetness than 'Redprime' and 'Sunpower', while they had less pyruvic acid value than 'Redsun' and 'Sunpower'. The the same trend was verified for the total phenol and total flavonoid, of which breeding lines were found to have more content than 'Redprime' or 'Sunpower'. Three major flavonoids, rutin (quercetin glycoside), myricetin, and quercetin, were identified and quantified whereas kaempferol was not detected in all cultivars. Rutin was the major flavonoid present in all cultivars (136.9 to $169.9{\mu}g{\cdot}g^{-1}$ F.W.), followed by quercetin (62.5 to $135.7{\mu}g{\cdot}g^{-1}$ F.W.). Relatively smaller amount of myricetin (11.2 to $16.1{\mu}g{\cdot}g^{-1}$ F.W.) was also detected. Among nine cultivars, 'Redsun' exhibited significantly ($p$ < 0.05) higher content of quercetin and rutin (135.7 and $169.9{\mu}g{\cdot}g^{-1}$ F.W., respectively), and S&P5296 had the highest content of myricetin($16.1{\mu}g{\cdot}g^{-1}$ F.W.). Breeding lines had more quercetin, rutin and myricetin contents than the cultivars 'Redprime' and 'Sunpower'. Hampyeong had the highest content for total phenol and total flavonoid, followed by Andong and Changyeong whereas Changyeong had the highest value for rutin, myricetin and quercetin followed by Hampyeong and Andong. Among red onion cultivars, 'Redsun' showed the highest value for anthocyanin, followed by S&P5295 and S&P5296, which the cultivar 'Redprime' had significantly (p<0.05) lower content(35.5 mg%).

• Journal of Life Science
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• v.29 no.12
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• pp.1371-1377
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• 2019

Oxidative stress induced by the over-production of reactive oxygen species (ROS) in the brain is the most common cause of neurodegenerative diseases such as Alzheimer's. In the present study, we investigated the protective effects of flavonoids and their glycosides, namely kaempferol, kaempferol-3-O-glucoside, quercetin, and quercetin-3-β-D-glucoside, against H₂O₂-induced oxidative stress in the C6 glial cells. The H₂O₂-treated glial cells exhibited decreased cell viability and increased ROS production when compared with normal cells. However, cells treated with each of the four flavonoids/glycosides demonstrated significantly increased viability and suppressed ROS production when compared with the H₂O₂-treated control group. These results indicate that flavonoids/glycosides attenuate oxidative stress induced by H₂O₂ in C6 glial cells. To confirm the protective molecular mechanisms, we measured pro-inflammatory factors such as inducible nitric oxide synthase, cyclooxygenase-2, and interleukin-1β. H₂O₂ treatment was seen to elevate these factors and decrease IκB-α in the C6 glial cells, while the flavonoids/glycosides induced a down-regulation of the pro-inflammatory factors and increased IκB-α, indicating a neuroprotective effects through attenuation of the inflammation. In particular, quercetin and its glycoside showed a higher neuroprotective effect than the kaempferol treatments. These results suggest that these flavonoids and their glycosides could be promising therapeutic agents for neurodegenerative diseases via the attenuation of oxidative stress.

• Applied Biological Chemistry
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• v.48 no.1
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• pp.98-102
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• 2005

The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.

• Journal of the Korean Society of Food Science and Nutrition
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• v.44 no.6
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• pp.823-831
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• 2015

Evaluation of biological activity and analysis of functional constituents from water and ethanol extracts of four different parts of mulberry (Morus alba L.) tree were carried out to develop functional ingredients and foods using extracts of mulberry tree. The water and ethanol extracts of four different parts of mulberry tree were prepared and their biological activities and functional constituents determined by in vitro assays and HPLC, respectively. In general, ethanol extracts showed stronger biological activities and higher functional constituents than water extracts. Ethanol extracts of mulberry fruit, root bark, and twig showed stronger antioxidant ($IC_{50}=128.4{\mu}g/mL$), ${\alpha}$-glucosidase ($IC_{50}=12.0{\mu}g/mL$), and lipoxygenase ($IC_{50}=36.3{\mu}g/mL$) and tyrosinase ($IC_{50}=410.3{\mu}g/mL$) inhibitory activities, respectively, than those of other parts. Mulberry fruit and leaf showed the highest contents of anthocyanin (cyanidin 3-glucoside: 213.20 mg/100 g) and chlorogenic acid (514.97 mg/100 g), and especially ethanol extract of mulberry leaf contained higher quercetin 3-O-(6-O-malonyl)glucoside (143.25 mg/100 g) and kaempferol 3-O-(6-O-malonyl)glucoside (30.25 mg/100 g) contents without water extract of mulberry leaf. Meanwhile, mulberry twig contained both oxyresveratrol glycoside (48.90 mg/100 g) and its aglycone (21.88 mg/100 g), whereas mulberry root bark contained mostly oxyresveratrol glycoside (724.05 mg/100 g). Additionally, mulberry root bark and leaf contained much higher ${\gamma}$-aminobutyric acid (223.90 mg/100 g) and 1-deoxynojirimycin (86.07 mg/100 g) contents, respectively, than other parts of mulberry tree. These results suggest that high quality processed foods and functional foods using mixtures of mulberry fruits, leaves, twigs, and root barks should be developed for prevention and inhibition of several pathological disorders.

• Journal of Korean Medicine for Obesity Research
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• v.21 no.1
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• pp.1-9
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• 2021

Objectives: The enzymatic hydrolysis is one of the processing methods that improve its effectiveness on medicinal herbs. In this research, changes in ingredients and activity by enzymatic hydrolysis were studied. Methods: For this study, a carbohydrate hydrolase such as viscozyme, which converts glycosides to aglycone, was applied to induce constituent changes in Sophora japonica Linne, Houttuynia cordata Thunberg and Leonurus japonicus Houttuyn. Changes in antioxidant activity were measured using the 1,1-diphenyl-2-picrylhydrazl (DPPH) method, and changes in ingredients were analyzed by high performance liquid chromatography. Results: As a result of enzymatic hydrolysis, the content of quercetin was increased from 1.26 mg/g to 29.66 mg/g in Sophora japonica Linne, from 0 mg/g to 0.66 mg/g in Houttuynia cordata Thunberg and from 0.43 mg/g to 0.71 mg/g in Leonurus japonicus Houttuyn. As a result of the antioxidant experimentation, the IC₅₀ of Sophora japonica Linne decreased from 5 ug/ml (MeOH extract) and 9.1 ug/ml (EtOAc fraction) to 3.0 ug/ml, Houttuynia cordata Thunberg decreased from 15.6 ug/ml (MeOH extract) and 13.6 ug/ml (EtOAc fraction) to 11.2 ug/ml, and Leonurus japonicus Houttuyn decreased from 14.4 ug/ml (MeOH extract) and 12.6 ug/ml (EtOAc fraction) to 10.2 ug/ml. Conclusion: In conclusion, it was confirmed that glycoside rutin contained in the three medicinal herbs was changed to quercetin which is the aglycone, by the enzymatic hydrolysis using viscozyme. In terms of antioxidant activity, Sophora japonica Linne showed a significant antioxidant activity value that closes to the control group butylated hydroxyanisole. Houttuynia cordata Thunberg and Leonurus japonicus Houttuyn showed a minor increase in antioxidant activity.