• Archives of Pharmacal Research
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• v.28 no.5
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• pp.573-581
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• 2005

Flavonoids, a group of low molecular weight phenylbenzopyrones, have various pharmacological properties including antioxidant activity, anticancer, and immunomodulatory effects. In the present study, lipopolysaccharide (LPS) and phorbol 12-myristate 13-acetate/phytohemagglutinin (PMA/PHA) were used as stimulants for RAW 264.7 macrophages and human peripheral blood mononuclear cell (hPBMC), and tumor necrosis factor (TNF)-${\alpha}$ and interleukin (IL)-2 productions were measured. In addition, flavonoids were examined for their effects on LPS-induced NO production in RAW 264.7 macrophages. The results showed that all compounds were not strongly cytotoxic at the tested concentrations on hPBMC and RAW 264.7 macrophages. On immunomodulatory properties, catechin, epigallocatechin (EGC), naringenin, and fisetin repressed NO production and TNF-${\alpha}$ secretion. Furthermore, catechin, epigallocatechin gallate (EGCG), epicatechin (EC), luteolin, chrysin, quercetin, and galangin increased IL-2 secretion while EGC, apigenin, and fisetin inhibited the secretion. These results indicated that flavonoids have the capacity to modulate the immune response and have a potential anti-inflammatory activity. There was no obvious structure-activity relationship regard to the chemical composition of the flavonoids and their cell biological effects.

• Food Science and Preservation
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• v.4 no.2
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• pp.181-187
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• 1997

New HPLC method was developed for determination of some flavonoids such as naringin, hesperidin, neohesperidin, rutin, quercitrin, naringenin, hesperetin and apigenin and their contents in citrus juice and citrus peel from citrus varieties Brown in Cheju. Detection was at 280nm and reverse phase ${\mu}$-Bondapak C-18 column was used. Water/methanol/acetic acid as the mobile phase was better than water/acetonitrile/acetic acid. Flavonoids were more stable in 20% n,n-dimethylformamide in methanol(20% DMF) than methanol and pH 12 adjusted by 1N-sodium hydroxide solution. Standard flavonoid solutions were injected three times consecutively and the reproduciability was 0.236 to 3.550%, Correlation coefficient of the calibration curve was 0.9946 to 0.9999. The exiraction efficiency of hesperidin from citrus peel was evaluated with different extraction method such as reflux, ultra-sonicating method, using three solvents (aqueous solutions with pH12 adjusted by 1N-sodium hydroxide, methanol and 20% DMF), respectively. The reflux for 4 hour in 20% DMF was the most efficient of the tested methods and solvents, and recovery percentage were 78.0∼130.0%. Flavonoids were determined in citrus juice. Naringin was 68.2mg/100$m\ell$ in Natsudaidai, Hesperidin were 85.6mg/100$m\ell$ in Sankyool and Neohesperidin was 25.3mg/100$m\ell$ in Dangyooja. Flavonoids were determined in citrus peel. Naringin was 110mg/g in Dangyooja, Hesperidin was 242mg/g in Hungjin and Neohesperidin was 87.9mg/g in Dangyooja.

• Preventive Nutrition and Food Science
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• v.7 no.1
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• pp.1-4
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• 2002

Eleven flavonoids, including rutin, naringin, hesperidin, neohesperidin, quercetin, naringenin, kaempferol, hesperetin, nobiletin, 3,5,6,7,8,3',4'-methoxylated flavone and tangeretin in the peel of late maturing citrus fruit species of Mucott (smith tangerine), Singamha (C. natsudidai), Sambogam (C. sulcata), Hongpalsak (C. hassaku), Seminol (Dancy tangerine) and Jawdung (C. aurantium) harvested during from August to December were analyzed with HPLC. The mobile phase consisted of water and acetonitrile with 0.5% acetic acid. Wavelength in UV detector was determined at 254 nm. Naringin and neohesperidin content in the peel of Jawdung harvested at the early stage of maturation were 34.02 mg/g and 13.68 mg/g, respectively, and it was highest among the tested citrus fruits. Hesperidin content in the peel of Mucott harvested at the earthy stage of maturation was 12.48 mg/g. Rutin content of Sambogam harvested at the early stage of maturation was 5.13 mg/g. Quercetin, naringein, kaempferol, nobiletin, 3,5,6,7,8,3',4'-methoxylated flavone flavonoids were in trace. Flavonoid contents of Singamha, Sambogam and Jawdung were high in the peel of fruits at the early stage of maturation, after which time they decreased rapidly.

• Bulletin of the Korean Chemical Society
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• v.26 no.8
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• pp.1203-1208
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• 2005

A computational study based on molecular dynamics (MD) simulations was performed in order to explain the difference in aqueous solubilities of two flavonoid/$\beta$-cyclodextrin ($\beta$-CD) complexes, hesperetin/$\beta$-CD and naringenin/$\beta$-CD. The aqueous solubility of each flavonoid/$\beta$-CD complex could be characterized by complexwater interaction not by flavonoid-CD interaction. The radial distribution of water around each inclusion complex elucidated the difference of an experimentally observed solubility of each flavonoid/$\beta$-CD complex. The analyzed results suggested that a bulky hydrophobic moiety (-$OCH_3$) of B-ring of hesperetin nearby primary rim of $\beta$-CD was responsible for lower aqueous solubility of the hesperetin/$\beta$-CD complex.

• Journal of Microbiology and Biotechnology
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• v.16 no.4
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• pp.619-622
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• 2006

Biotransformation is a good tool to synthesize regioselective compounds. It could be performed with diverse sources of genes, and microorganisms provide a myriad of gene sources for biotransformation. We were interested in modification of flavonoids, and therefore, we cloned a putative O-methyltransferase from Bacillus cereus, BcOMT-2. It has a 668-bp open reading frame that encodes a 24.6-kDa protein. In order to investigate the modification reaction mediated by BcOMT-2, it was expressed in E. coli as a His-tag fusion protein and purified to homogeneity. Several substrates such as naringenin, luteolin, kaempferol, and quercetin were tested and reaction products were analyzed by thin layer chromatography (TLC) and high performance liquid chromatography (HPLC). BcOMT-2 could transfer a methyl group to substrates that have a 3' functional hydroxyl group, such as luteolin and quercetin. Comparison of the HPLC retention time and UV spectrum of the quercetin reaction product with corresponding authentic 3'-methylated and 4'-methylated compounds showed that the methylation position was at either the 3'-hydroxyl or 4'-hydroxyl group. Thus, BcOMT-2 transfers a methyl group either to the 3'-hydroxyl or 4'-hydroxyl group of flavonoids when both hydroxyl groups are available. Among several flavonoids that contain a 3'- and 4'-hydroxyl group, fisetin was the best substrate for the BcOMT-2.

• Korean Journal of Pharmacognosy
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• v.54 no.2
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• pp.53-60
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• 2023

Athyrium acutipinnulum, called as Ulleungdo ladyfern (Seom-go-sa-ri), is a native plant of South Korea. A. acutipinnulum has been consumed as foods and also traditionally used for the treatment of epilepsy, gonorrhea and nerve disorder. The methanolic extract and EtOAc soluble fraction of A. acutipinnulum showed the antioxidant activity. Fractionation using various chromatographic techniques resulted in the isolation of 13 compounds. The structures were elucidated on the basis of spectroscopic methods as seven phenolic compounds, methyl 2-hydroxy-3-phenylpropanoate (1), protocatechualdehyde (2), caffeic acid (3), trans-p-coumaric acid (4), (-)-4-E-caffeoyl-L-threonic acid (5), 5-O-caffeoyl shikimic acid (6) and 5-O-caffeoyl quinic acid (7), three flavonoids, quercetin 3-O-β-glucoside (8), naringenin-7-O-β-glucoside (9) and sutchenoside A (10), two steroids, ponasterone A (11) and ecdysone (12) and a coumarin, esculetin (13). Among them, compounds 5 and 10 were first reported from Athyrium spp and compounds 2, 5, 6 and 7 showed the antioxidant activity.

• Archives of Pharmacal Research
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• v.16 no.1
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• pp.18-24
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• 1993

In this inverstigation, the various flavonoid aglycones were evaluated for their inhibitory activities against croton-oil or arachidonic acid induced mouse ear edema by oral or topical administration. The compounds tested were thirteen derivatives of flavan-3-ol(catechin and epicatechin), flavanone (flavanone and naringenin), flavone (flavone, chrysin and apigenin), flavonol(favonol, galangin, quercetin and morin) and isoflavone (biochanin A and 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone), along with hydrocortisone, indomethacin, 4-bormophenacyl bromide, nordihydroguaiaretic acid and phenidone as positive controls. A(isoflavone) were found to show broad inhibitoty activities (14-52%) against croton-oil or arachidonic acid induced ear edema by oral or topical application at the dose of 2 mg/mouse, although they showed less activity than hydrocortisone (26-88%) or indomethacin (36-80%). Flavonoid agtlycones tested showed higher activity when aplied topically than by the oral administration. It was also found that they inhibited arachidonic acid induced edema more profoundly than croton-oil induced edema by topical application. In arachidonic acid induced edema when applied topically, flavone derivatives such as flavone, chrysin and apigenin were revealed to be the good inhibitory agents in addition to flavonols and isoflavones. When quercetin and biochanin. A were selected for evaluating in carrageenan induced rat pleurisy and biochanin both flavonoids showed antiinflammatory activity at the dose of 70 mg/kg by the oral adminis-tration. All of these results revealed that flavonoid aglycones, especially 5,7-dihydroxy-flavonols having hydroxyl group(s) in B-ring and biochanin A (isoflavone) possessed in vivo antiinflammatory activity.

• Herbal Formula Science
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• v.26 no.3
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• pp.237-250
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• 2018

Objectives : This study is a pharmacological network approach, aimed to identify the potential active compounds contained in Curcumae Radix, and their associated targets, to predict the various bio-reactions involved, and finally to establish the cornerstone for the deep-depth study of the representative mechanisms. Methods : The active compounds of Curcumae Radix have been identified using Traditional Chinese Medicine System Pharmacology Database and Analysis Platform. The UniProt database was used to collect each of information of all target proteins associated with the active compounds. To find the bio-metabolic processes associated with each target, the DAVID6.8 Gene Functional classifier tool was used. Compound-Target and Target-Pathway networks were analyzed via Cytoscape 3.40. Results : The target information from 32 potential active compounds of Curcumae Radix was collected through TCMSP analysis. The active compounds interact with 133 target genes engaging in total of 885 biological pathways. The most relevant pathway was the lipid-related metabolism, in which 3 representative active compounds were naringenin, oleic acid, and ${\beta}-sitosterol$. The mostly targeted proteins in the lipid pathway were ApoB, AKT1 and PPAR. Conclusions : The pharmacological network analysis is convenient approach to predict the overall metabolic mechanisms in medicinal herb research, which can reduce the processes of various experimental trial and error and provide key clues that can be used to validate and experimentally verify the core compounds.

• 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.

• Horticultural Science & Technology
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• v.34 no.5
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• pp.677-691
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• 2016

To assess South Korean commercial tomato cultivars, regular and cherry tomato cultivars were grown in the greenhouse and evaluated for color attributes, titratable acidity, pH, total soluble solids, carotenoids (lycopene and ${\beta}$-carotene), total phenols, flavonoids, vitamin C, and antioxidant activity. Significant differences (p < 0.05 using Duncan's multiple range test (DMRT)) were observed in the levels of most phytochemicals, quality parameters, and antioxidant activity among the twenty South Korean tomato cultivars tested. Lycopene and ${\beta}$-carotene contents varied significantly (p < 0.05 using DMRT), from $0.95mg{\cdot}100g^{-1}$ to $5.12mg{\cdot}100g^{-1}$ and $0.65mg{\cdot}100g^{-1}$ to $3.56mg{\cdot}100g^{-1}$ of fresh weight, respectively. ${\beta}$-carotene contents exhibited the highest genetic variation (59.2%), followed by naringenin (52.8%) and other phytochemicals. Most of the cherry tomato cultivars had statistically higher levels (p < 0.05 using DMRT) of carotenoids, phenols, flavonoids, vitamin C, and antioxidant activity compared to the regular tomato varieties, suggesting their higher nutritional value. Lycopene content was highest in the cultivars YoYo, Jicored, Titi-Chal, TY-Endorphin, and Rubyking. Cultivars Rubyking, TY-Endorphin, and Titi-Chal also showed relatively higher antioxidant activities in three assays: 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and ferric ion reducing antioxidant power (FRAP) assays. All the antioxidants, except luteolin, were positively correlated with antioxidant activities; the highest correlation was observed between total phenol and antioxidant activities, followed by the correlation between rutin and vitamin C. Cultivars identified to have superior nutritional status would be useful in tomato breeding programs to further improve quality and health benefits of tomatoes for the fresh and processed markets.