• Korean Journal of Pharmacognosy
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• v.42 no.2
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• pp.149-154
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• 2011

Seventeen 30% EtOH extracts from the Compositae plants collected in Gangwon-do, Korea during autumn season were analyzed by HPLC using three standard caffeoylquinic acids (chlorogenic acid, 3,5-di-O-caffeoylquinic acid, 3,5-di-Omuco-quinic acid) and six flavonoids (rutin, isoquercitrin, astragalin, quercitrin, quercetin and kaempferol) to find the composition of phenolic compounds and also assayed to evaluate the peroxynitrite (ONOO$^-$) scavenging effect. The extracts with $IC_{50}$ values less than 2.0 ${\mu}g/ml$ were as follows: Aster tartaricus ($IC_{50}$, $1.26{\pm}0.10\;{\mu}g/ml$), A. maaki ($1.45{\pm}0.03\;{\mu}g/ml$), Solidago virga-aurea, ($1.45{\pm}0.03\;{\mu}g/ml$), Picris hierraciodes var. glabrescens ($1.45{\pm}0.04 \;{\mu}g/ml$), Lactuca triangulata ($1.50{\pm}0.09\;{\mu}g/ml$), Chrysanthemum zawadskii ssp. acutilobum, ($1.79{\pm}0.14\;{\mu}g/ml$). Particularly, the proportion of total phenolic compounds measured in the extract of L. triangulata was highest as the value 54.51%.

• Korean Journal of Plant Resources
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• v.11
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• pp.89-109
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• 1998

Screening of new antioxidants form oriental medicines resulted in the isolation of a new antioxidative compound and eight known compounds from the stem bark of Kalopanax pictus. On the basis of various spectrosopic studies, the structure of the new compound was determined to be 4-rhamnose-3,5-dimethoxybenzoic acid methly ester. Other known compounds were identified as ferulic acid, 4,5,6,-trihydroxyflavanone, 2', 4',4' -trihydroxychalcone, caffeic acid, coniferyl alcohol, syringin, 1,3-di-O-caffeoylquinic acid. These compounds showed lipid peroxidation inhibitory acitivity in rat liver microsomes and free radical scavenging acitivity.

• Korean Journal of Pharmacognosy
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• v.52 no.2
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• pp.112-117
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• 2021

Helianthus annuus L. has been reported with various pharmacological activities such as antibacterial, antidiabetic, and antioxidant effects. According to recent studies, H. annuus L. is known to contain components such as phenolic compounds, flavonoids, alkaloids, sesquiterpenoids, and lignans. The seeds of H. annuus L. have been reported to contain chlorogenic acid and di-O-caffeoylquinic acid as major components. However, studies on the main components and content of leaves of H. annuus L. are still incomplete. Therefore, in this study, the contents of four major components of H. annuus L. were evaluated by simultaneous quantitative analysis with high performance liquid chromatography (HPLC)-diode array detector (DAD). The isolated four compounds Caffeoylquinic acid(CQA), 3,4-dicaffeoylquinic acid(3,4-DCQA), 3,5-dicaffeoylquinic acid(3,5-DCQA) and 4,5-dicaffeoylquinic acid(4,5-DCQA) were shown in a large linearity with a correlation coefficient (R²) of 0.99. In addition, as a result of intra-inter day analysis of four major compounds by the analysis method of this study, the accuracy of 88.46% or more and less than 112.85% and excellent precision of less than 3% were shown, the content analysis showed CQA (0.383±0.018 mg/g), 3,4-DCQA (0.282±0.017 mg/g), 3,5-DCQA (1.109±0.068 mg/g), and 4,5-DCQA (0.673±0.020 mg/g).

• Journal of the Korean Society of Food Science and Nutrition
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• v.45 no.1
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• pp.61-67
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• 2016

An HPLC analysis method was developed for standard determinations of chlorogenic acid, 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid as functional health materials in Ligularia fischeri extract. HPLC was performed on a $C_{18}$ Kromasil column ($4.6{\times}250mm$, $5{\mu}m$ column) with a gradient elution of 0.1% (v/v) trifluoroacetic acid and acetonitrile at a flow rate of 1.0 mL/min at $30^{\circ}C$. The analytes were detected at 330 nm. The HPLC method was validated in accordance with the International Conference on Harmonization guideline of analytical procedures with respect to specificity, precision, accuracy, and linearity. The limits of detection and quantitation for the four compounds were 3.0~14.6 and $9.2{\sim}44.4{\mu}g/mL$, respectively. Calibration curves showed good linearity ($r^2$ > 0.999), and the precision of analysis was satisfied (less than 0.9%). Recoveries of quantified compounds ranged from 98.96 to 101.81%. This result indicates that the established HPLC method is very useful for the determination of marker compounds in Ligularia fischeri leaf extracts.

• Natural Product Sciences
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• v.17 no.4
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• pp.342-349
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• 2011

This study was performed to determine the composition of phenolic substances contained in the leaves of Cirsium setidens (Compositae), validate the high-performance liquid chromatography (HPLC) method, and determine the in vivo sedative effect of the main component pectolinarin. Six phenolic compounds isolated from C. setidens were spectroscopically identified as chlorogenic acid (1), hyperoside (2), 3,4-di-O-caffeoylquinic acid (3), caffeic acid methyl ester (4), linarin (5), and pectolinarin (6) and then used as standard compounds for HPLC analysis. HPLC proved to be precise, accurate, and sensitive for the simultaneous analysis of the phenolic substances. In particular, six compounds showed good regression ($R^2$ > 0.999) within test ranges and recovery was in the range of 95.4 - 104.8%. The content of pectolinarin was considerably higher (156.48 mg/g) than those of other phenolic substances including the other flavone glycoside, linarin (18.99 mg/g). The contents of other phenolic substances, in order, were chlorogenic acid (8.41 mg/g), 3,4-di-O-caffeoylquinic acid (5.74 mg/g), hyperoside (4.33 mg/g), and caffeic acid methyl ester (0.51 mg/g). Oral administration with compound 6 (10 and 20 mg/kg) enhanced the sleeping time induced by pentobarbital in mice, indicating that it has a sedative effect.

• YAKHAK HOEJI
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• v.51 no.2
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• pp.88-95
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• 2007

Atractylodes macrocephala has been used for renal anorexia, gastroenteritis, cold, dyspepsia in Korean folk medicine. Specially aerial parts has been eaten as edible mountain herbs. In order to investigate the efficacy of antioxidant activity the activity guided fractionation and isolation of physiologically active substance were peformed. For the investigation of the active components from Atractylodes macrocephala MeOH extracts of aerial parts of Atractylodes macrocephala Koidzumi L. were suspended with H$_2$O, partitioned by CHCl$_3$. In order to investigate the efficacy of antioxidative activity the activity guided fractionation and isolation of physiologically active substance were peformed. CHCl$_3$, H$_2$O, 30% MeOH, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method. It was revealed that 30% MeOH and 60% MeOH fractions have significantly antioxidant activity. From 30% MeOH and 60% MeOH fraction, six flavonoids (7-methoxy-pinocembrin-7-O-${\beta}$-D-glucopyranoside, apige nin-8-C-${\beta}$-D-glucopyranoside, 4'-caffeoyl-luteolin-6-glucopyranoside, luteloin-6-C-${\beta}$-D-glucopyranoside, apigenin-6-C-${\beta}$-D-glucopyranoside, luteolin) and four phenylpropanoids (3-feruloylquinic acid, 4,5-di-O-caffeoylquinic acid, feruloyl acid, 3,5-di-O-caffeoylquinic acid) were isolated. To investigate the antioxidant activities of each compounds, we measured radical scavening activity with DPPH method and anti-lipid peroxidative efficacy on low density lipoprotein (LDL) with TBARS assay. Six compounds (III, IV, V, VI, IX, X) which have antioxidant factor showed significant activities.

• BMB Reports
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• v.46 no.10
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• pp.513-518
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• 2013

We investigated the protective effects of Gymnaster koraiensis against oxidative stress-induced hepatic cell damage. We used two different cytotoxicity models, i.e., the administration of tert-butyl hydroperoxide (t-BHP) and acetaminophen, in HepG2 cells to evaluate the protective effects of G. koraiensis. The ethyl acetate (EA) fraction of G. koraiensis and its major compound, 3,5-di-O-caffeoylquinic acid (DCQA), exerted protective effects in the t-BHP-induced liver cytotoxicity model. The EA fraction and DCQA ameliorated t-BHP-induced reductions in GSH levels and exhibited free radical scavenging activity. The EA fraction and DCQA also significantly reduced t-BHP-induced DNA damage in HepG2 cells. Furthermore, the hexane fraction of G. koraiensis and its major compound, gymnasterkoreayne B (GKB), exerted strong hepatoprotection in the acetaminophen-induced cytotoxicity model. CYP 3A4 enzyme activity was strongly inhibited by the extract, hexane fraction, and GKB. The hexane fraction and GKB ameliorated acetaminophen-induced reductions in GSH levels and protected against cell death.

• Korean Journal of Pharmacognosy
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• v.35 no.4 s.139
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• pp.368-374
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• 2004

Cervical cancer is one of the leading causes of female death. Viral oncoproteins E6 and E7 are selectively retained and expressed in carcinoma cells infected with HPV (Human papillomavirus) type 16. The HPV is cooperated in immotalization and transformation of primary keratinocyte. E6 and E7 oncoproteins interfere the functions of tumor suppressor proteins p53 and retinoblasoma protein (pRb), respectively. Among a lots of natural products, Artemisia scoparia Waldstein et Kitamura has inhibitory effects on the binding between E6 oncoprotein and tumor suppressor p53, or the binding between E6 and E6 associated protein (E6AP), an E3 ubiquitin-protein ligase. HPV oncoprotein inhibitors from Artemisia scoparia W. were isolated by solvent partition and column chromatography (Silica gel, RP-18) and the inhibitory compounds were finally purified by HPLC using an ELISA screening system based on the binding between E6 and E6AP. The aim of this study is to identify the structure of inhibitory compounds and to investigate whether these compounds have inhibitory effects on the functions of E6 oncoprotein. We investigated whether 3,5-di-O-caffeoylquinic acid (DCQA) extracted from Artemisia scoparia W. Could inhibit the function of E6 oncoprutein. DCQA inhibited the in vitro binding of E6 and E6AP which are essential for the binding and degradation of the tumor suppressor p53 and also inhibited the proliferation of human cervical cancer cell lines (SiHa and CaSKi) in a dose response manner. These results suggest that DCQA inhibited the function of E6 oncoprotein, suggesting that it can be used as a potential drug for the treatment of cervical cancers infected with HPV.

• Journal of the Korean Society of Food Science and Nutrition
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• v.46 no.6
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• pp.759-764
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• 2017

Reactive oxygen species (ROS) and advanced glycation end products (AGEs) are valuable therapeutic targets for the regulation of diabetic complications. Activity-guided isolation of the ethylacetate (EtOAc)-soluble portion of 70% ethanolic extract from aerial parts of Ainsliaea acerifolia was performed, followed by AGE formation inhibition assay for the characterization of four dicaffeoylquinic acid derivatives of a previously known structure, methyl 3,5-di-O-caffeoyl-epi-quinate (1), 3,5-di-O-caffeoyl-epi-quinic acid (2), 4,5-di-O-caffeoyl-quinic acid (3), and methyl 4,5-di-O-caffeoyl-quinate (4). The structures of these compounds were confirmed by interpretation of nuclear magnetic resonance (NMR, $^1H-$, $^{13}C-NMR$, two-dimensional NMR) and mass spectroscopic data. Among the isolates, the major secondary metabolites, 3,5-di-O-caffeoyl-epi-quinic acid (2) and 4,5-di-O-caffeoyl-quinic acid (3) showed the most potent inhibitory effects against AGE formation with $IC_{50}$ values of $0.6{\pm}0.1{\mu}M$ and $0.4{\pm}0.1{\mu}M$, respectively. Furthermore, all isolated dicaffeoylquinic acid derivatives were evaluated for their radical scavenging activities using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical, and compound 3 exhibited the most potent inhibitory effect in a concentration-dependent manner. This result suggests that the caffeoylquinic acid dimers isolated from A. acerifolia might be beneficial for the prevention of diabetic complications and related diseases.

• Biomolecules & Therapeutics
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• v.17 no.4
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• pp.412-417
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• 2009

In the course of screening for antioxidant compounds by measuring the radical scavenging effect on DPPH (1,1-diphenyl- 2-picrylhydrazyl), a total extract of the twigs of Vitex rotundifolia (Verbenaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of three iridoid compounds, 10-O-vanilloylaucubin (1), 10-O-p-hydroxybenzoylaucubin (2) and aucubin (3), two C-glycoside flavones, vitexin (4) and orientin (5), and a quinic acid derivative, 3,4-di-O-caffeoylquinic acid (6). Their structures were elucidated by spectroscopic studies. Among them, compounds 5 and 6 showed the significant antioxidative effects on DPPH free radical scavenging test. In riboflavin-NBT-light and xanthine-NBT-xanthine oxidase systems, compounds 5 and 6 exhibited the formation of the blue formazan in a dose-dependent manner. Compounds 5 and 6 showed better superoxide quenching activities than vitamin C.