• Applied Chemistry for Engineering
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• v.29 no.1
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• pp.49-55
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• 2018

In this study, we investigated the cellular protective effects and mechanisms of nicotiflorin and its aglycone kaempferol isolated from Annona muricata. The protective effect of these components against $^1O_2$-induced cell damage was also studied by using L-ascorbic acid and (+)-${\alpha}$-tocopherol as controls. Kaempferol exhibited the most potent protective effect, followed by (+)-${\alpha}$-tocopherol and nicotiflorin. L-Ascorbic acid did not exhibit any cellular protective effects. To elucidate the mechanism underlying protective effects, the quenching rate constant of the singlet oxygen, free radical-scavenging activity, ROS-scavenging activity, and uptake ratio of the erythrocyte membrane were measured. The results showed that the cell membrane penetration is a key factor determining the cellular protective effect of kaempferol and its glycoside nicotiflorin. The result from L-ascorbic acid demonstrated that the cellular protective effect of a compound depends on its ability to penetrate the cell membrane and is independent of its antioxidant capacity. In addition, it is suggested that cellular protective effects of kaempferol and (+)-${\alpha}$-tocopherol depend not only on the cell permeability, but also on free radical- and ROS-scavenging activities. These results indicate that the cell permeability and free radical- and ROS- scavenging activities of antioxidants are major factors affecting the protection of cell membranes against the oxidative damage induced by photosensitization reaction.

• Applied Biological Chemistry
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• v.48 no.1
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• pp.98-102
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• 2005

The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.

• International Journal of Industrial Entomology and Biomaterials
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• v.41 no.2
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• pp.45-50
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• 2020

Morus alba has white and/or purple fruits with a very sweet taste and low acidity. Most Korean mulberry trees have purple fruits. However, Baekokwang is a unique mulberry genetic resource in Korea with white fruits. In this study, flavonoids contents of Baekokwang mulberry leaf and fruit were analyzed using ultrahigh performance liquid chromatography coupled with diode array detection and quadrupole time-of-flight mass spectrometry (UPLC-DAD-QTOF/MS) technique. UPLC-DAD-QTOF/MS chromatogram showed that 15 flavonoids and 9 flavonoids were isolated and identified from the mulberry leaf and fruit. Total flavonoids contents of Baekokwang leaves and fruits were 812.7 mg and 35.0 mg, respectively. Baekokwang leaves had 4 major flavonoids including quercetin 3-O-(6"-O-malonyl) glucoside, 235.3 ppm, kaempferol 3-O-(6"-O-malonyl) glucoside, 132.3 ppm, kaempferol 3-O-rutinoside (nicotiflorin), 108.1 ppm, and quercetin 3-O-rutinoside (rutin), 103.8 ppm. Baekokwang fruits had 3 major flavonoids including quercetin 3-O-(6"-O-malonyl) glucoside, 13.0 ppm, quercetin 3-O-rutinoside (rutin), 7.8 ppm, and kaempferol 3-O-rutinoside (nicotiflorin), 5.7 ppm. From the above results, mulberry leaves have rich flavonoids compared to its fruits.

• Journal of Applied Biological Chemistry
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• v.66
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• pp.477-483
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• 2023

The flowers of Carthamus tinctorius (Safflower) were extracted with 80% aqueous methanol (CTex) and the concentrates were partitioned into EtOAc (CTE), n-BuOH (CTB), and H₂O (CTW) fractions. Repeated silica gel (SiO₂) and octadecyl silica gel column chromatographies for the EtOAc and n-BuOH fractions led to isolation of four flavonol glycosides. Nuclear magnetic resornance, infrarad spectroscopy, and mass spectroscopy revealed the chemical structure of the isolated compounds, astragalin (1), isoquercetin (2), nicotiflorin (3), and rutin (4). Quantitative analysis of four isolated compounds in CTex was performed by HPLC. CTex was found to contain 1 at 0.107, 2 at 0.367, 3 at 6.752, and 4 at 0.991 mg/g, respectively. Through this study, an experiment was conducted to evaluate the protective effect on pancreatic islets of the extract, solvent fractions, and all isolated compounds using a zebrafish larvae damaged by alloxan. Pancreatic islet size treated with EtOAc (CTE), n-BuOH (CTB), and H₂O (CTW) fractions and compounds 1-4 significantly increased compared to the alloxan-induced group. These results indicate that C. tinctorius flowers and its isolated compounds are used as potential anti-diabetic agents.

• Natural Product Sciences
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• v.10 no.4
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• pp.173-176
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• 2004

Six compounds were isolated from the BuOH soluble fraction of the leaves of Staphylea bumalda. On the basis of spectral data, they were identified as atragalin (1), $2-methyl-5,\;7-dihydroxy-chromone-7-O-{\beta}-D-glucopyranoside$ (2), isoquercitrin (3), nicotiflorin (4), kaempferol 3-neohesperidoside (5), kaempferol $3-O-[{\alpha}-rhamno-pyranosyl-(1\;{\to}\;4)-rhamnopyranosyl-(1\;{\to}\;6)-{\beta}-D-glucopyranoside]$ (6), respectively.

• Korean Journal of Pharmacognosy
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• v.43 no.2
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• pp.127-136
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• 2012

Eight flavonoids were isolated from the BuOH fraction of the 70% EtOH extract of Zizyphus jujuba var. spinosa seeds along with three known compounds, daucosterol (1), butyl ${\beta}$-D-fructofuranoside (2), and magnoflorine (4). On the basis of spectroscopic methods and comparison with literature values their structures were elucidated as 6"'-feruloylspinosin (3), nicotiflorin (5), 6"'-p-coumaroylspinosin (6), isospinosin (7), 6"'-vanilloylspinosin (8), spinosin (9), hovetrichoside C (10), and camelliaside B (11). Compounds 1, 2, 10, and 11 were isolated from this plant for the first time.

• 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.

• Natural Product Sciences
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• v.14 no.4
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• pp.281-288
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• 2008

From the MeOH extract of the whole plants of Lathyrus davidii (Fabaceae), thirteen constituents were isolated and identified as the flavonoids astragalin, isoquercitrin, nicotiflorin, and rutin, as the saponins soyasapogenol B 3-O-${\beta}$-D-glucuronopyranoside, azukisaponins II and V, soyasaponins II and V and as 4-O-${\beta}$-Dglucopyranosyl syringic acid, uracil and n-hexacosanol. Five saponins and 4-O-${\beta}$-D-glucopyranosyl syringic acid were isolated from the BuOH fraction as their methyl esters. Ombuoside (rutin 7,4'-di-O-methyl ether) was also isolated from the methylated BuOH-soluble fraction. However, no ombuoside was detected in the HPLC analysis of the nonmethylated BuOH fraction. Therefore, ombuoside is an artifact derived from methylation of rutin. All of these compounds were isolated for the first time from this plant.

• Natural Product Sciences
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• v.27 no.4
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• pp.284-292
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• 2021

Recently, a phytoestrogenic functional food has been developed using the fruits of Sophora japonica. Phytochemical investigation of fruits of S. japonica led to the isolation of eight flavonoid glycosides using various chromatographic techniques. The isolated compounds were identified as genistin (1), sophoricoside (2), genistein 7,4'-di-O-β-D-glucopyransoide (3), sophorabioside (4), genistein-7-O-β-D-glucopyranoside-4'-O-[(α-L-rhamnopyranosyl)-(1→2)-β-D-glucopyranoside] (5), sophoraflavonoloside (6), nicotiflorin (7) and kaempferol-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside (8), respectively, by comparison of their spectroscopic data with those reported in the literature. In addition, a new HPLC-DAD method for simultaneous determination of the isolated compounds was developed to quantitate the contents of flavonoids in S. japonica and S. flavescens. The method was validated in terms of limit of detection, limit of quantitation, specificity, linearity, precision and accuracy. The validated method was successfully applied to determine eight flavonoids in two Sophora species. The contents of eight flavonoids varied according to the parts and species. Particularly, it was found that only the fruits of S. japonica contained sophoricoside, a phytoestrogenic isoflavone.

• Journal of Applied Biological Chemistry
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• v.61 no.1
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• pp.39-46
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• 2018

Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p-coumaroyltyramine (3), trans-N-p-feruloyltyramine (4), 4-O-feruloylquinicacid (5), chlorogenic acid (6), 3-O-feruloylquinicacid (7), ferulic acid (8), protopine (9), Kaempferol 3,7-di-O-${\beta}-{\text\tiny{D}}$-glucopyranoside (10), kaempferol 3-O-${\beta}-{\text\tiny{D}}$-glucopyranosyl-7-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranoside (11), ${\alpha}-rhamnoisorobin$ (12), astragalin (13), and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines ($TNF-{\alpha}$, $IL-1{\beta}$ and IL-6) in a dose- dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.