• Natural Product Sciences
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• v.23 no.3
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• pp.183-191
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• 2017

Luteolin 5-O-glucoside is the major flavonoid from Korean thistle, Cirsium maackii. We previously reported the anti-inflammatory activities of luteolin 5-O-glucoside in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. In this study, we determined the anti-inflammatory mechanisms of luteolin 5-O-glucoside through the inhibition of nitric oxide (NO) production in vitro and in vivo. Results revealed that luteolin 5-O-glucoside dose-dependently inhibited NO production and expression of iNOS and COX-2 in LPS-induced RAW 264.7 cells. Luteolin 5-O-glucoside also significantly inhibited the translocation of $NF-{\kappa}B$, the activation of MAPKs, and ROS generation in LPS-induced RAW 264.7 cells. In addition, protein expressions of Nrf-2 and HO-1 were also upregulated by luteolin 5-O-glucoside treatment. Moreover, luteolin 5-O-glucoside inhibited ${\lambda}-carrageenan-induced$ mouse paw edema by 65.34% and 48.31% at doses of 50 and 100 mg/kg body weight, respectively. These findings indicate potential anti-inflammatory effect of luteolin 5-O-glucoside particularly by downregulating $NF-{\kappa}B$ and upregulating HO-1/Nrf-2 pathway.

• Korean Journal of Pharmacognosy
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• v.47 no.3
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• pp.211-216
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• 2016

In the course of our continuing search for biologically active components from Korean medicinal plants, we isolated the main compound, luteolin 5-glucoside from aqueous fraction of Ajuga spectabilis. The structure was elucidated by the basis of $^1H$ and $^{13}C$ NMR and TOF ESI-MS data. Quantitative analysis of luteolin 5-glucoside was carried out on a XBridge C18 column ($S-5{\mu}m$, $4.6{\times}250mm$) with gradient elution composed of acetonitrile:water. The results exhibit that the average content of main compound in A. spectabilis were 0.048%. Oxidative stress plays a major role Alzheimer's disease (AD) and other neurodogenerative disease. AD is major health problem and there is currently no clinically accepted treatment to cure or stop its progression. Pretreatment with luteolin 5-glucoside markedly attenuated $H_2O_2$-induced cell viability loss in a dose-dependent manner. Luteolin 5-glucoside also inhibited the formation of intracellular reactive oxygen species in SH-SY5Y. The results suggest that luteolin 5-glucoside from A. spectabilis has protective effects against oxidative stress-induced cytotoxicity, which might be a potential therapeutic compound for treating and/or preventing neurodegenerative disease implicated with oxidative stress.

• Archives of Pharmacal Research
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• v.25 no.3
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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.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.33 no.3
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• pp.139-144
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• 2007

In the previous study, we reported the antioxidative activity of Equisetum arvense extracts. In this study, its inhibitory effect on elastase and components were investigated. Aglycone fractions obtained from the deglycosylation reaction of ethylacetate fraction among the Equisetum arvense extracts, showed 4 bands and 4 peaks in TLC and HPLC experiments, respectively. Four components were identified as luteolin(composition ratio, 19.12%), quercetin(12.87), apigenin(15.81) and kaempferol(52.20). TLC chromatogram of ethylacetate fraction of Equisetum arvense extract revealed 7 bands and HPLC chromatogram showed 8 peaks, which were identified as kaempferol-3,7-O-diglucoside(composition ratio, 15.74%), luteolin-5-O-glucoside(galuteolin, 11.91), apigenin-5-O-glucoside(12.91), kaempferol-3-O-glucoside(astragalin, 27.94), quercetin-glycoside(10.81, structure was not determined), kaempferol-glycoside (12.33, structure was not determined), luteolin(3.72) and apigenin(4.62) in the order of elution time. The inhibitory effect of aglycone fraction on elastase($IC_{50}$, $9.8{\mu}g/mL$) was very high. But ethylacetate fraction(flavonoid glycosides) rarely exhibited the inhibitory activity on elastase. Combined with the previous results of the antioxidative activity of Equisetum arvense extracts, it is concluded that the inhibitory activity on elastase of the aglycone fraction could be applicable to new functional cosmetics for smoothing wrinkles.

• Korean Journal of Pharmacognosy
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• v.26 no.4
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• pp.337-343
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• 1995

Two flavone glycosides were isolated from the aerial part of Angelica keiskei Koidz and identified by means of spectral analysis as luteolin-$7-O-{\beta}-{_D}-glucoside$ and Iuteolin-7-O-rutinoside. Intraperitoneal administration of methanolic extract(100mg/kg) and $luteolin-7-O-{\beta}-{_D}-glucoside(5mg/kg)$ isolated from this plant produced a significant hypolipemic activity.

• Korean Journal of Pharmacognosy
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• v.31 no.3
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• pp.340-344
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• 2000

Lonicerae Flos, the flower of Lonicera japonica Thunb., has been used as a diuretic, stomachic, antipyretic, analgesic and anti-inflammatory agent in Korea. In order to evaluate the quality of Lonicerae Flos, the method of isolation and quantitative determination of luteolin $7-O-{\beta}-D-glucoside$ as a reference standard compound has been developed. Different specimens of Lonicerae Flos were collected from twenty Korean markets and were analyzed with HPLC using the mobile phase of MeOH-4.5% acetic acid solution (16.5:83.5). The average content of luteolin $7-O-{\beta}-D-glucoside$ from Lonicerae Flos in Korean markets was $0.43{\pm}0.34%$.

• Natural Product Sciences
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• v.26 no.4
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• pp.289-294
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• 2020

Eclipta prostrata is an annual herb, belonging to Asteraceae family, and has been traditionally used to improve immunity and treat hepatitis and bacterial disease in Korea. In this study, a new coumestan glucoside (1) along with ten known compounds (2 - 11) was isolated from E. prostrata. The chemical structures of isolates were elucidated to be wedelolactone-9-O-β-D-glucopyranoside (1), wedelolactone (2), demethylwedelolactone (3), apigenin (4), apigenin-7-sulfate (5), luteolin (6), luteolin-7-sulfate (7), luteolin-7-O-β-D-glucopyranoside (8), pratensein-7-O-β-D-glucopyranoside (9), 3,4-di-O-caffeoylquinic acid (10) and 3,5-di-O-caffeoylquinic acid (11) based on the spectroscopic evidence.

• Natural Product Sciences
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• v.21 no.1
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• pp.42-48
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• 2015

Lactuca raddeana (Compositae) is used to treat obesity and complications due to diabetes. The five phenolic compounds including chlorogenic acid, chicoric acid, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, luteolin were qualitatively identified by LC-ESI-MS analysis. The contents were quantitatively determined by HPLC, under the condition of a Capcell Pak C18 column ($5{\mu}m$, $250mm{\times}4.6mm\;i.d.$) and a gradient elution of 0.05% trifluoroacetic acid (TFA) and 0.05% TFA in $MeOH-H_2O$ (60 : 40). The contents of chicoric acid (100.99 mg/g extract) and luteolin 7-O-glucoside (101. 69 mg/g extract) were high, while those of other three phenolic substances were very low. The 3T3-L1 adipocyte cells treated with chicoric acid and luteolin 7-O-glucuronide significantly suppressed the accumulation of fat, suggesting they are effective against obesity. Since high level of peroxynitrite (ONOO) causes cardiovascular disease in obese patients, its scavenging activity was also studied.

• Journal of Applied Biological Chemistry
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• v.51 no.2
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• pp.57-60
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• 2008

Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.

• Korean Journal of Plant Resources
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• v.25 no.5
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• pp.640-646
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• 2012

This research was attempted to determine the composition of flavone glycosides (luteolin 7-O-glucoside, luteolin 7-O-glucuronide, linarin) in addition to luteolin simultaneously in aerial part of Youngia japonica (Compositae) by high-performance liquid chromatography. The MeOH extract was further fractionated into the three parts, $CHCl_3$ fraction, EtOAc fraction and BuOH fraction, to investigate the contents of the four flavones in the three fractions. The content of luteolin 7-O-glucuronide (10.07 mg/g) was highest in the MeOH extract among those of the flavones. These four compounds were observed to be less than 1.0 mg/g in $CHCl_3$- and EtOAc fractions but relatively high in BuOH fraction.