• Korean Journal of Plant Resources
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• v.33 no.1
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• pp.40-49
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• 2020

The objectives of this study were to evaluate total phenolic content (TPC) and individual phenolic compounds in leaves of perilla genetic resources, assess whether they could be used as distinguishing factor among germplasms, and evaluate their relationship with some quantitative and qualitative morphological characters. TPC and individual phenolic compounds were determined using Folin-Ciocalteu method and UPLC-PDA system, respectively. Wide variations in TPC (7.99 to 133.70 mgGAE/g DE), rosmarinic acid (ND to 21.05 mg/g DE), caffeic acid (ND to 1.17 mg/g DE), apigenin-7-O-diglucuronide (ND to 2.21 mg luteolin equivalent (mgLUE)/g DE), scutellarein-7-O-glucuronide (ND to 5.25 mg LUE/g DE), and apigenin-7-O-glucuronide (ND to 2.81 mg LUE/g DE) were observed. Intensities of green pigment at abaxial and adaxial leaf surfaces were positively correlated with phenolic compounds whereas leaf length and width had negative correlation. Purple pigmented accessions were shorter in leaf length and width but exhibited higher amount of phenolic compounds compared to green pigmented accessions in most cases. Leaf shape was not related with content of phenolic compounds, color of leaves, and length/width of leaves. TPC and individual phenolic compounds along with morphological characters could be useful distinguishing factors for perilla genetic resources.

• Natural Product Sciences
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• v.25 no.4
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• pp.326-333
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• 2019

The purpose of our study was to evaluate anti-AD potential of Cirsium maackii flowers. MeOH extract, CH₂Cl₂, EtOAc, and n-BuOH fraction of this flower notably inhibited BACE1 (IC₅₀ = 76.47 ± 1.66, 22.98 ± 1.45, 8.65 ± 0.63, and 72.47 ± 3.04 ㎍/mL, respectively). β-amyrenone (49.70 mg) (1), lupeol acetate (1.43 g) (2), lupeol (1.22 g) (3), lupenone (23.70 mg) (4), β-sitosterol (1.01 g) (6), and β-sitosterol glucoside (13.00 mg) (7) from CH₂Cl₂, apigenin (100.20 mg) (8), luteolin (19.00 mg) (9), apigenin 7-O-glucuronide methyl ester (21.30 mg) (14), and tracheloside (53.70 mg) (5) from EtOAc, apigenin 5-O-glucoside (11.00 mg) (10), luteolin 5-O-glucoside (11.00 mg) (11) and apigenin 7-O-glucuronide (91.00 mg) (12) from n-BuOH, and luteolin 7-O-glucuronide (22.00 mg) (13) from H₂O fraction were isolated. HPLC showed high levels of 8, 9 and 12 in MeOH extract (33.07 ± 0.07, 31. 44 ± 0.17 and 16.89 ± 0.33 mg/g, respectively), EtOAc (161.01 ± 1.78, 96.93 ± 0.34 and 73.38 ± 0.06 mg/g, respectively), and n-BuOH fraction (32.18 ± 0.33, 44.31 ± 0.32 and 105.94 ± 0.36 mg/g, respectively). Since, 3 and 9 are well-known BACE1 inhibitors, the anti-AD activity of C. maackii flower might be attributable to their presence.

• Korean Journal of Breeding Science
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• v.41 no.4
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• pp.391-396
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• 2009

Perilla frutescens, which belonging to the Labiatae family, is widely cultivated oil crop and have been used traditional herbal medicine in East Asia such as Korea, China, and Japan. Especially, the leaves and the seeds of this species are important in Korean traditional cooking, as one of the popular garnish and food colorants. Numerous studies have revealed that the beneficial health effects of perilla are due to its several phytochemicals contents, such as rosmarinic acid, caffeic acid, luteolin, and apigenin. For this reason, increasing the content of phytochemicals in perilla hasbecome a major breeding objective. The genetic diversity of the rosmarinic acid, caffeic acid, luteolin, and apigenin content in perilla seed is poorly documented. We analyzed the rosmarinic acid, caffeic acid, luteolin, and apigenin content of 203 accessions of perilla germplasm by high performance liquid chromatography (HPLC). The rosmarinic acid and luteolin contents ofgermplasms were ranged from $15.7{\mu}g/g$ to $2717.1{\mu}g/g$ and from $1.6{\mu}g/g$ to $582.4{\mu}g/g$ respectively.

• 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 the Korean Society of Food Science and Nutrition
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• v.21 no.3
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• pp.296-301
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• 1992

From the leaves of Ixeris sonchifolia (Compositae), luteolin and its glucoside and apigenin glucuronide were isolated and their structures were characterized on the basis of spectral data. Besides these flavonoids, the composition and relative content of free amino, acids and related compounds, compared to standards determined under identical conditions was also investigated using automatic amino acid analyzer. Major free amino acids were glutamic acid, aspartic acid, serine, proline, valine and arginine.

• Archives of Pharmacal Research
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• v.26 no.2
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• pp.151-156
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• 2003

We investigated the anti-proliferative effects of luteolin and apigenin, isolated from Ixeris sonchifolia Hance, on HepG2 human hepatocellular carcinoma cells. In MTT assay luteolin showed more efficient anti-proliferative effects on cells than apigenin did. According to propidium iodide staining and flow cytometry studies, we postulated that these effects might be a result of cell cycle arrest. Hence we examined the changes of protein expressions related to cell cycle arrest. Western blotting data demonstrated that the down-regulated expression of CDK4 was correlated to the increase of p53 and CDK inhibitor $p21^{WAF1/CIP1}$ protein. These data suggest that luteolin may have potential as an anti-cancer agent.

• Archives of Pharmacal Research
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• v.20 no.2
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• pp.148-154
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• 1997

The antioxidant activity of Artemisia iwayomogi was determined by measuring the radical scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. The methanol extract of A. iwayomogi showed strong antioxidant activity, and thus fractionated with several solvents. The antioxidant activity potential of the individual fraction was in the order of ethyl acetate > n-butanol > water > chloroform > n-hexane fraction. The ethyl acetate and n-butanol soluble fractions exhibiting strong antioxidant activity were further purified by repeated sitica get and Sephadex LH-20 column chromatography. Antioxidant chlorogenic acid was isolated as one of the active principles from the n-butanol fraction, together with the inactive components, 1octacosanol, scopoletin, scopolin, apigenin $7, 4^{I}$-di-O-methylether, luteolin $6, 3^{I}$-di-O-methylether (jaceosidin), apigenin methylether (genkwanin), 2, 4-dihydroxy-6-methoxyacetophenone $4-O-{\beta}-$D-glucopyranoside and quebrachitol. The antioxidant activity of chlorogenic acid was comparable to that of L-ascorbic acid, which is a well known antioxidant.

• YAKHAK HOEJI
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• v.47 no.5
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• pp.300-306
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• 2003

Rhizoma of Smilax china has been used as anti-inflammatory and analgesic, antiedemic agent in Korean folk medicine. In order to investigate the efficacy of anti-oxidative activity, the activity-guided fractionation and the isolation were performed. Each fractions ($H_2O$ fraction, 20％, 40％, 60％, 100％ MeOH fractions and CHCl$_3$ fraction) was examined antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging potential. It was revealed that 40％, 20％ MeOH fractions and $H_2O$ fractions have significant anti-oxidative activity. From 40％ and 20％ MeOH fractions two flavonoid glycosides and one procyanidin were isolated and elucidated apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside, apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow6)-$\beta$-D-glucopyranoside and catechin(4$\alpha$\longrightarrow6)epicatechin through their physicochemical data and IR, FAB-MS, $^{13}$ C-NMR, and $^1$H-NMR analysis with authentics, respectively. The isolated compounds were examined by DPPH method. Apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside and catechin (4$\alpha$\longrightarrow6) epicatechin showed powerful radical scavenging activities on DPPH radical among three compounds.

• Culinary science and hospitality research
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• v.15 no.3
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• pp.284-293
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• 2009

This study investigated chemical composition and antioxidant activity in the aerial parts or roots of Korean and Chinese Cirsium. Water was abundant in their roots than their aerial parts, and its content was similar between Korean Cirsium and Chinese one. Ash was abundant in the aerial parts of Korean one. Protein was abundant in the aerial parts of Korean one and the roots of Chinese one. Lipid content was abundant in the roots of Chinese one. Carbohydrate was abundant in the roots of Korean one while K content was abundant in the roots of Chinese one. Ca and Mg contents were abundant in the aerial parts of Korean one. P and Fe contents were abundant in the aerial parts of Korean one. Cu content was abundant in the aerial parts of Korean and Chinese ones. Vitamin A and vitamin C were not detected, but vitamin E and $\beta$-carotene were contained 5.35 IU/100 g, 1113.18 ${\mu}g$/100 g in the aerial parts of Korean one. Yield, total phenolics and total flavonoid contents were abundant in the roots of Korean one. Silymarin, cynarin, and narirutin were not detected in Korean and Chinese ones, but apigenin was identified in the aerial parts of Korean one. Acacetin was identified in the roots of Chinese one. Antioxidant activity was low in Korean and Chinese ones. These results suggest that nutrition composition, total phenolic content, total flavonoid content and apigenin content in the aerial parts of Korean Cirsium was superior than those in the roots of Korean and Chinese Cirsium.

• Journal of Life Science
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• v.19 no.8
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• pp.1009-1015
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• 2009

The beneficial use of sedatives is often required for medically ill patients. This study examined the effect of plant flavonoids and diazepam peripheral-type benzodiazepine receptor (PBR) activation and glucose utilization in breast cancer cells, along with their interactions. In estrogen receptor negative MDA-MB-231 cells, the anti-proliferative activity of fisetin (3,7,3',4'-tetrahydroxyflavone) and diazepam was more prominent than in estrogen receptor positive MCF-7 cells. Unlike PBR ligands, treatment with $10^{-6}$ M concentration of diazepam for 3 days exhibited anti-proliferative effects, while similar to apigenin (4',5,7-Trihydroxyflavone) and fisetin, diazepam hardly affected the PBR mRNA expression by MDA-MB-231 cells. Treatment with $10^{-6}$ M concentration of flavonoids and diazepam for 3 days inhibited the glucose utilization of MDA-MB-231 cells. Treatment with $10^{-6}$ M concentration of flavonoids and diazepam for 6 days showed increased cytotoxicity and reduced the PBR mRNA expression of the MDA-MB-231 cells. Apigenin enhanced diazepam-induced anti-proliferative effects on the MDA-MB-231 cells as well. All together, this study showed the in vitro anti-proliferative activity of flavonoids and diazepam on MDA-MB-231 breast cancer cells, plus additive enhancements. In conclusion, this study provides experimental basis for advanced trials in the future.