• Journal of Life Science
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• v.28 no.5
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• pp.509-516
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• 2018

Five phenolic compounds were isolated from the ethyl acetate fraction of leaves from Stewartia koreana, and their nitric-oxide (NO) inhibitory activities were measured to identify the major active constituents responsible for the efficacy of the extract against inflammatory reactions. These five compounds were quercetin (1), quercitrin (2), hyperin (3), quercetin-3-O-(6"-O-galloyl)-${\beta}$-D-galactopyranoside (4), and kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside (5). Among the separated compounds in the EtOAc fraction, compounds 4 and 5 were isolated for the first time, and no study has yet reported their anti-inflammatory effects. The compounds were identified by spectroscopic analysis, and the isolated compounds showed significant NO inhibitory effects in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Compound 5 showed the most potent inhibitory effect (63.35% inhibition) against LPS-induced NO production compared to that of compound 1 (17.17%), compound 2 (5.0%), compound 3 (3.92%), and compound 4 (6.32%) at $10{\mu}g/ml$ concentration. NO production was inhibited by suppressing the protein expression of inducible nitric-oxide synthase in LPS-stimulated RAW 264.7 macrophages. These results indicate that kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside might be the major active compound responsible for the anti-inflammatory effects of S. koreana.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.48 no.2
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• pp.123-134
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• 2022

In this study, the whitening and antioxidant effects of the extracts from Hydrangea petiolaris (H. petiolaris) leaves was confirmed, and the chemical structure was identified by separating the active ingredients. In the whitening tests using α-MSH stimulated B16F10 melanoma cells, the n-hexane (Hex) fraction inhibited the cellular melanogenesis and intracellular tyrosinase activities without causing cell toxicity. In addition, the Hex fraction reduced expression of tyrosinase and TRP-2 protein. Upon the anti-oxidative studies by DPPH and ABTS⁺ radicals, potent radical scavenging activities were observed in the ethyl acetate (EtOAc) fraction. Also, for the cellular protective effects on HaCat keratinocytes damaged by H₂O₂, the EtOAc fraction indicated protective effects against oxidative stress. Eight phytochemicals were isolated from the extract of H. petiolaris leaves; ethyl linoleate (1), ethyl linolenate (2), 1-linoleoyl glycerol (3), 1-linolenoyl glycerol (4), epi-catechin (5), afzelin (6), quercitrin (7), hyperin (8). Among the isolates, the compounds 5 - 8 showed DPPH and ABTS⁺ radical scavenging activities. The contents of quercitirin, a major isolated in this extract, determined by HPLC analysis were confirmed to be about 31.3 mg/g for the 70% ethanol extract and 169.8 mg/g for the EtOAc fraction. Based on these results, it was suggested that the extract from H. petiolaris leaves could be potentially applicable as whitening and anti-oxidative ingredients in cosmetic formulations.

• Korean Journal of Pharmacognosy
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• v.39 no.3
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• pp.260-264
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• 2008

Eight compounds were isolated from the EtOAc soluble fraction of Euphorbia supina MeOH extract as the radical scavengers for antioxidant activity. Their structures were identified as kaempferol (1), quercetin (2), juglanin (3), avicularin (4), astragalin (5), isoquercitrin (6), hyperin (7), and nicotiflorin (8) by spectroscopic analysis. The antioxidant activity was evaluated by the ORAC (oxygen radical absorbance capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methylpropionamidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 4, 6, and 7 exhibited potent antioxidant activity, whereas the other compounds showed weaker activity than trolox.

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.529-533
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• 2005

In the course of searching for hepatoprotective agents from natural products, six compounds were isolated from the MeOH extract of the leaves of Juglans sinensis, as guid ed by their DPPH free radical scavenging activity. The structures were determined as juglanoside B (1), quercetin 3-O-${\alpha}$-L-arabinofuranoside (avicularin, 2), quercetin 3-O-${\alpha}$-L-arabinopyranoside (guaijaverin,3), quercetin 3-O-${\alpha}$-L-rhamnopyranoside (quercitrin,4), (+)-catechin (5) and quercetin 3-O-${\beta}$- D-galactopyranoside (hyperin,6). Compounds 2-6 showed significant DPPH free radical scavenging effects. An evaluation for the hepatoprotective activity of the isolated compounds on drug-induced cytotoxicity was conducted, and compounds 1, 2, and 5 showed protective effects against nitrofurantoin-induced cytotoxicity, and compound 5 also exhibited a moderate protective effect on amiodarone-induced cytotoxicity in Hep G2 cells.

• Korean Journal of Medicinal Crop Science
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• v.13 no.2
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• pp.85-90
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• 2005

Phytochemical study on the EtOAc fraction from a MeOH extract of the leaves of Alnus hirsuta Rupr. led to the isolation of nine compounds betulin (1), betulinic acid (2), hirsutanonol (3), hirsutenone (4), quercetin (5), avicularin (6), gallic acid (7), hyperin (8), and daucosterol (9). Among them, six compounds 1, 2, 57, and 9 are report from this plant for the first time. All isolated compounds were evaluated for their antioxidant activity using DPPH radical scavenging capacity and inhibition effect on mitochondrial lipid peroxidation. Six phenolic compounds 3-8 were found to have potent antioxidant activity. Of which, compounds 3, 4 and 5 showed significant free radical scavenging activity with the $IC_{50}$ values of $18.3\;{\pm}\;2.5,\;15.7\;{\pm}\;3.8\;and\;23.5\;{\pm}\;3.1\;{\mu}m$, respectively. In addition, the compounds 3-8 exhibited inhibition effect on the mitochondrial lipid peroxidation with the $IC_{50}$ values of $88.0\;{\pm}\;6.5,\;12.6\;{\pm}\;1.2,\;8.0 \;{\pm}\;1.1,\;58.5\;{\pm}\;4.3,\;173.6\;{\pm}\;15.2,\;and\;75.0\; {\pm}\; 6.7\;{\mu}m$, respectively.

• Natural Product Sciences
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• v.22 no.1
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• pp.25-29
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• 2016

High-performance liquid chromatography was performed in order to analyze the changes in the flavonoid content (rutin, hyperin, afzelin, quercetin, and kaempferol) of Acanthopanax divaricatus and A. koreanum, in response to different cultivation methods (pinching height, planting time, and top dressing). The total flavonoid content of A. divaricatus and A. koreanum ranged from 0.201 to 0.690 mg/g with different pinching heights, 0.143 to 1.001 mg/g for different planting times, and 0.156 to 1.074 mg/g depending on the rate of fertilizer application. In both A. divaricatus and A. koreanum, the total flavonoid content in the upper section of the plant was greater than that in the lower section. These results demonstrate which cultivation methods maximize the flavonoid content of A. divaricatus and A. koreanum, and thus help to optimize flavonoid yields to improve production for nutraceutical, pharmaceutical, and cosmeceutical applications.

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.842-850
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• 2002

Tissue factor (TF, tissue thromboplastin or coagulation factor III) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification utilizing a bio-assay method of prothrombin time prolongation, was carried out to yield five active flavoniods such as hovetrichoside C (1) ($IC_{50}$ = 14.0 $\mu$g), luteolin-7-Ο-$\beta$-D-glucuronide (3) ($IC_{50}$ = 31.9$\mu$g), hyperin (4) ($IC_{50}$ = 20.8 $\mu$g), avicularin (6) ($IC_{50}$ = 54.8 $\mu$g) and quercitrin (10) ($IC_{50}$ = 135.7 $\mu$g), along with other inactive compounds such as ($\pm$)-(2E,4E)-Ο-$\beta$-D-glucopyranosyl-4'-hydroxy-$\beta$-ionylideneacetic acid ester (2), genistein-7-Ο-$\beta$-D-glucopyranoside (5), luteolin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (7), luteolin-7-Ο-$\beta$-D-glucuronide methyl ester (8), tricetin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (selagin-4'-Ο-$\beta$-D-glucopyranoside) (9), (-)-epicatechin (11), luteolin-4'-Ο-$\beta$-D-glucopyranoside (12) and apigenin-7-Ο-$\beta$-D-glucuronide methyl ester (13). The structures of the isolated compounds were elucidated through spectral analysis. Among them, compounds 1 to 9, 12 and 13 were isolated for the first time from the fruits of this plant and the compound 9 is a new flavonoid.

• Korean Journal of Plant Resources
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• v.23 no.5
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• pp.393-398
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• 2010

Naturally occurring substances which strongly scavenge peroxynitrite(ONOO-) are evaluated to be beneficial for cardiovascular, diabetic, hypercholesterolemic and obese disease. To search for bioactive substances with peroxynitritescavenging activity from the young leaves of Heracleum moellendorffii(Umbelliferae) used for a mountainous vegetable, the experiment on peroxynitrite-scavenging assay, phytochemical isolation and HPLC analysis were undertaken. Activity-guided fractionation led to the separation of astragalin and hyperoside which were identified by physicochemical and spectroscopic data. The $IC_{50}$ values of astragalin and hyperoside were shown as $5.80{\pm}0.62$ and $0.560{\pm}0.26\;{\mu}M$, respectively, in the assay. The HPLC analysis led to the quantitative determination of astragalin and hyperoside by $30.0{\pm}0.01$ and $17.0{\pm}0.02\;mg/g$ dried weight, respectively.

• Bulletin of the Korean Chemical Society
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• v.35 no.8
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• pp.2361-2366
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• 2014

A new aliphatic acid amide, ZP-amide F (1), and eight known compounds, including bungeanumamide A (2), tumuramide C (3), ZP-amide A (4), ZP-amide B (5), ZP-amide D (6), hyperin (7), quercitrin (8), and (-)-sesamin (9), were isolated from pericarps of Zanthoxylum piperitum. The effects of these compounds on $TNF{\alpha}$-induced NF-${\kappa}B$ activation and transactivational activity of PPARs, including $PPAR{\alpha}$, $PPAR{\beta}({\delta})$ and $PPAR{\gamma}$ subtypes, were evaluated. Compounds 7 and 9 exhibited potent inhibitory effects on $TNF{\alpha}$-induced NF-${\kappa}B$ activation with $IC_{50}$ values of 5.50 and $8.10{\mu}M$, respectively. Aliphatic acid amide compounds 3, 4 and 6 displayed enhanced effects on PPAR transactivational activity with $EC_{50}$ values of 47.12, 19.13 and $12.02{\mu}M$, respectively. Among them, compound 4 demonstrated an increase in $PPAR{\alpha}$ transactivational activity, compound 3 showed a moderate increase on all PPAR subtypes, whereas compound 6 displayed weak PPAR transactivational activity.

• YAKHAK HOEJI
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• v.42 no.4
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• pp.414-421
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• 1998

In order to compare the suppressive effect of quercetin and its glycosides, such as quercitrin (quercetin-3-rhamnoside), isoquercitrin (quercetin-3-glucoside), hyperin (querceti n-3-galactoside)and rutin (quercetin-3-rhamnosyl glucoside), on the genotocicity by benzo(a)pyrene(B(a)P), in vitro sister chromatid exchange(SCE) test using mouse spleen lymphocytes and in vivo micronucleus test using mouse peripheral blood were performed. B(a)P-induced SCEs in vitro were slightly decreased by the simultaneous treatment of quercetin and its glycosides, although there was no significant decrease. On the other hand, MNU induced micronucleated reticulocytes(MNRL7s) in vivo were significantly decreased with a dose-dependent manner in all compounds tested. However, there were no differences between quercetin aglycone and glycosides in the suppressive effects under experimental condition of this study. To elucidate, the action mechanism of quercetin aglycone and its glycosides against B(a)P-induced genotoxicity, the assay of DNA binding with B(a)P was studied. Quercetin aglycone and its glycosides inhibited B(a)P metabolism in the presence of S-9 mix and decreased the B(a)P/DNA binding in the calf thymus DNA with S-9 mix. These results suggest that antigenotoxicity of quercetin antiglycosides on B(a)P-induced genotoxicity is due to decrease of DNA binding with B(a)P through the inhibition of metabolism with B(a)P in the calf thymus DNA. Therefore, quercetin and its glycosides may act as an antigenotoxicity agent and may be useful as a chemopreventive agent of polycyclic aromaic hydrocarbons like B(a)P.