• Journal of the Korean Society of Food Science and Nutrition
• /
• v.40 no.4
• /
• pp.517-524
• /
• 2011

Eleven polyphenolic compounds, including procatechuic and chlorogenic acids, (+)-dihydroquercetin, rutin, isoquercitrin, quercitrin, (+)-dihydrokaempferol, trans-resveratrol, moracin, quercetin and 4-prenylmoracin were isolated and purified from the methanolic extract of defatted mulberry seed residue by a series of column chromatography including silica gel, Sephadex LH-20, and ODS-A, and their chemical structures were identified by spectral analysis. The antioxidant activities of the eleven isolated polyphenolic compounds were measured spectrophotometrically using DPPH radical. Among the eleven polyphenolic compounds tested, rutin ($IC_{50}=20.2\;{\mu}M$), isoquercitrin ($IC_{50}=22.5\;{\mu}M$), quercitrin ($IC_{50}=24.6\;{\mu}M$), quercetin ($IC_{50}=27.8\;{\mu}M$), (+)-dihydroquercetin ($IC_{50}=28.9\;{\mu}M$), and chlorogenic acid ($IC_{50}=30.6\;{\mu}M$) exhibited stronger antioxidant activity than L-ascorbic acid ($IC_{50}=31.5\;{\mu}M$) and ${\alpha}$-tocopherol ($IC_{50}=52.3\;{\mu}M$), whereas procatechuic acid ($IC_{50}=68.2\;{\mu}M$) showed lower activity. In addition, (+)-dihydrokaempferol ($IC_{50}=33.8\;{\mu}M$), trans-resveratrol ($IC_{50}=36.2\;{\mu}M$), moracin ($IC_{50}=47.6\;{\mu}M$), and 4-prenylmoracin ($IC_{50}=48.2\;{\mu}M$) exhibited moderate antioxidant activity. Furthermore, levels of the eleven polyphenolic compounds from three different types of mulberry seeds were quantified by HPLC, and their contents were as follows: rutin (311~60.0 mg/100 g)> quercitrin (7.2~34.2 mg/100 g)> (+)-dihydroquercetin (13.2~33.1 mg/100 g)> quercetin (15.8~19.5 mg/100 g)> 4-prenylmoracin (10.5~43.3 mg/100 g)> isoquercitrin (5.8~15.4 mg/100 g)> chlorogenic acid (0.0~15.3 mg/100 g)> moracin (4.7~7.2 mg/100 g)> procatechuic acid (0.0~11.6 mg/100 g)> (+)-dihydrokaempferol and trans-resveratrol (<0.1 mg/100 g). The 'Daesungppong' mulberry seeds among the three cultivars had higher flavonoid contents, such as rutin and quercetin derivatives, while the 'Iksuppong' seeds had the highest contents of phenolic acids and moracin derivatives. 'Cheongilppong' had lower amounts of polyphenolic compounds than the other two mulberry seeds. These results indicate that mulberry seeds containing antioxidant polyphenolic compounds may be potentially useful sources of anti-diabetic, anti-hypertensive, and anti-aging agents for functional foods and cosmetics.

• Korean Journal of Environment and Ecology
• /
• v.28 no.5
• /
• pp.574-587
• /
• 2014

In this study, vertical distribution patterns of Quercus mongolica Fisch. ex Ledeb. and Q. serrata Murray in Korea were recognized and possibility of introgressive hybridization and gene flow between Q. mongolica and Q. serrata in Mt. Jiri was inferred by flavonoid analyses. The most critical factor on distribution patterns was the altitude in accordance with temperature condition. A zonal distribution was recognized: Quercus mongolica zone in the upper area and Q. serrata zone in the lower area. In Central Korea, the range of vertical distribution of Q. mongolica was above alt. 100m, almost everywhere, whereas that of Q. serrata was from alt. 0 m to alt. 500(-700) m, and the species is rare above that altitude. But in Southern Korea, Q. serrata is found up to above alt. 1,000 m, whereas frequency of Q. mongolica reduces as elevation in decline and the species is rare below alt. 300 m, even though pure stands being formed on higher mountain slope. Altitudinal distribution of the two species, however, overlaps, where the two species occur together. Thirty-seven individuals of Q. mongolica and Q. serrata in Mt. Jiri and other area were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols kaempferol, quercetin, isorhamnetin, myricetin, and four compounds among the flavonoid compounds were acylated. Kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside and its acylated compounds were major constituents and present in all individuals. Quercus mongolica is distinguished from Q. serrata by the presence of quercetin 3-O-arabinosylglucoside and by high concentration of three acylated compounds, acylated kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside, and by relatively low concentration or lacking of rhamnosyl flavonol compounds. There are intraspecific variations in flavonoid profiles for Q. mongolica and Q. serrata, the flavonoid profiles for individuals of two species in hybrid zone (sympatric zone) tend to be similar to each other, qualitatively and quantitatively. These findings strongly suggest that gene exchange or gene flow occurs through the introgressive hybridization between Q. mongolica and Q. serrata in Mt. Jiri. Therefore, Quercus crispula, occupying morphologically intermediate position between Q. mongolica and Q. serrata, is suspected of being a hybrid taxon of two putative parental species.

• Journal of Life Science
• /
• v.24 no.10
• /
• pp.1092-1101
• /
• 2014

In this study, the distribution patterns of Quercus mongolica and Q. serrata in Korea were investigated, and the possibility of introgressive hybridization and gene flow between Q. mongolica and Q. serrata in Mt. Seorak was inferred by flavonoid analyses. The most critical factor in the vertical and horizontal distribution patterns of Q. mongolica and Q. serrata was the temperature, in accordance with latitude and altitude. The species showed a zonal distribution, with a Q. mongolica zone in the upper area and a Q. serrata zone in the lower area. In Mt. Seorak, Central Korea, the range of the vertical distribution of Q. mongolica was generally above an altitude of 100 m, whereas that of Q. serrata was an altitude of 0-400 m (-500) and rarely above an altitude of 500 m. However, in Mt. Jiri, Southern Korea, Q. serrata was found up to an altitude of 1,000~1,200 m, whereas the frequency of Q. mongolica was reduced at lower elevations and the species was rare below an altitude of 300 m, although pure stands were found on higher mountain slopes above an altitude of 1,200 m. The altitudinal distribution of the two species overlapped, where the two species occurred together. The leaf flavonoid constituents of thirty-four individuals of Q. mongolica and Q. serrata in Mt. Seorak and Mt. Jiri, Korea were examined. Twenty-four flavonoid compounds were isolated and identified. These were glycosylated derivatives of flavonols kaempferol, quercetin, isorhamnetin, myricetin. Five compounds among the flavonoid compounds were acylated. Kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside, and its acylated compounds were major constituents and present in all individuals. Quercus mongolica is distinguished from Q. serrata by the presence of quercetin 3-O-arabinosylglucoside, a high concentration of three acylated compounds (kaempferol 3-O-glucoside, quercetin 3-O-glucoside, and quercetin 3-O-galactoside), and a relatively low concentration or lack of rhamnosyl flavonol compounds. Intraspecific variations, however, were found in the flavonoid profiles of Q. mongolica and Q. serrata, and the flavonoid profiles of individuals belonging to the two species in a hybrid zone (sympatric zone) tended to be similar, qualitatively and quantitatively. These findings strongly suggest that gene exchange or gene flow occurs through introgressive hybridization between Q. mongolica and Q. serrata in Mt. Seorak.

• Natural Product Sciences
• /
• v.17 no.4
• /
• pp.279-284
• /
• 2011

Phytochemical studies on the whole extract of Sedum hybridum L., a Mongolian medicinal plant, has been undertaken to isolate active principles responsible for its anti-oxidative and antibacterial activities. Eighteen known compounds, i.e. (1) quercetin, (2) kaempferol, (3) herbacetin-8-O-${\beta}$-D-xylopyranoside, (4) myricetin, (5) gossypetin-8-O-${\beta}$-D-xylopyranoside, (6) gallic acid, (7) 2,4,6-tri-O-galloyl-D-glucopyranose, (8) 6-O-galloylarbutin, (9) myricetin-3-O-${\alpha}$-L-arabinofuranoside, (10) quercetin-3-O-${\alpha}$-L-arabinofuranoside, (11) caffeic acid, (12) ethylgallate, (13) (-) epigallocatechin-3-O-gallate, (14) palmitic acid, (15) stearic acid, (16) stearic acid ethyl ether, (17) ${\beta}$-sitosterol and (18) ${\beta}$-sitosteryl-O-${\beta}$-D-glucopyranose have been isolated and their molecular structures identified by spectroscopic analysis. Thirteen substances including seven flavonol components (1, 2, 3, 4, 5, 9 and 10), five gallic acid derivatives (6, 7, 8, 12 and 13) and caffeic acid (11) exhibited significant, dose-dependent, DPPH radical scavenging activity. Galloyl esters 12 and 13 were revealed to be main active principles for the antibacterial property of the extract of Sedum hybridum L.

• Journal of Korea Foresty Energy
• /
• v.22 no.1
• /
• pp.30-36
• /
• 2003

2kg of pollen extracted with EtOH(98%), concentrated, and fractionated with a series of hexane, CH$_2$Cl$_2$ EtOAc and $H_2O$ on a separately funnel. Each fraction was freeze dried to give dark-brown powder and EtOAc soluble portion of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol as eluents. Spectrometric analysis such as NMR and FAB-MS including TLC were performed to characterize the structures of isolated compounds. Pollen contained a small amount of flavonol derivatives such as quercetin-3-O-$\beta$-D-glucopyranoside and kaempferol-3-O-$\beta$-D-rutinoside in addition to a small amount of flavanonol compound such as aromadendrin-5-methyl ether and acid compound such as.

• Korean Journal of Pharmacognosy
• /
• v.43 no.3
• /
• pp.201-205
• /
• 2012

In the course of screening pancreatic lipase inhibitory activity, total methanolic extract and EtOAc-soluble fraction of Duchesnea chrysantha showed significant inhibitory activity. Further fractionation and isolation of the EtOAc-soluble fraction resulted in five compounds, which were identified as trans-tiliroside (1), isovitexin (2), kaempferol-8-O-${\beta}$-glucoside (3), kaempferol-3-O-${\beta}$-glucoside (4) and quercetin-3-O-${\beta}$-glucoside (5). All the five flavonoids derivatives were first reported from this plant but showed weak inhibitory effects on pancreatic lipase activity.

• Biomolecules & Therapeutics
• /
• v.19 no.1
• /
• pp.27-32
• /
• 2011

The activation of microglia induces the overproduction of inflammatory mediators that are responsible for the neurodegenerative disorders including Alzheimer's disease and Parkinson's disease. The large amounts of prostaglandin $E_2$ ($PGE_2$) produced by inducible cyclooxygenase (COX-2) is one of the main inflammatory mediators that can contribute to neurodegeneration. The inhibition of COX-2 thus may provide therapeutic strategy for the treatment of neurodegenerative diseases. From the activity-guided purification of EtOAc soluble fraction of Siegesbeckia glabrescens, four compounds were isolated as inhibitors of $PGE_2$ production in LPS-activated microglia. Their structures were determined as 3, 4'-dimethylquercetin (1), 3, 7-dimethylquercetin (2), 3-methylquercetin (3) and 3, 7, 4'-trimethylquercetin (4) by the mass and NMR spectral data analysis. The compounds 1-4 showed dose-dependent inhibition of $PGE_2$ production in LPS-activated microglia with their $IC_{50}$ values of 7.1, 4.9, 4.4, $12.4\;{\mu}M$ respectively. They reduced the expression of protein and mRNA of COX-2 through the inhibition of I-${\kappa}B{\alpha}$ degradation and NF-$\kappa}B$ activity that were correlated with the inactivation of p38 and ERK. Therefore the active compounds from Siegesbeckia glabrescens may have therapeutic effects on neuro-inflammatory diseases through the inhibition of overproduction of $PGE_2$ and suppression of COX-2 overexpression.

• Journal of Microbiology and Biotechnology
• /
• v.26 no.11
• /
• pp.1845-1854
• /
• 2016

The transglycosylation activity of amylosucrase (ASase) has received significant attention owing to its use of an inexpensive donor, sucrose, and broad acceptor specificity, including glycone and aglycone compounds. The transglycosylation reaction of recombinant ASase from Deinococcus radiopugnans (DRpAS) was investigated using various phenolic compounds, and quercetin-3-O-rutinoside (rutin) was found to be the most suitable acceptor molecule used by DRpAS. Two amino acid residues in DRpAS variants (DRpAS Q299K and DRpAS Q299R), assumed to be involved in acceptor binding, were constructed by site-directed mutagenesis. Intriguingly, DRpAS Q299K and DRpAS Q299R produced 10-fold and 4-fold higher levels of rutin transglycosylation product than did the wild-type (WT) DRpAS, respectively. According to in silico molecular docking analysis, the lysine residue at position 299 in the mutants enables rutin to more easily position inside the active pocket of the mutant enzyme than in that of the WT, due to conformational changes in loop 4.

• Journal of Korea Foresty Energy
• /
• v.21 no.1
• /
• pp.56-64
• /
• 2002

2kg of the dried leaves of Thuja orientalis Linnaeus were ground, extracted with acetone-$H_2O$(7:3, v/v), concentrated, and fractionated with a series of hexane, $CH_2C1_2$ EtOAc and water on a separators funnel. Each fraction was freeze dried to give dark-brown powder and a EtOAc soluble portion. of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Spectrometric analyses such as NMR and FAB-MS including TLC were performed to characterize the structures of isolated compounds. The leave of Thuja orientalis Linnaeus contained a large amount of flavononol derivatives such as quercetin-3-O-$\alpha$-L-rhamnopyranoside and myricetin-3-O-$\alpha$-L-rhamnopyranoside in addition to a small amount of flavan compounds such as (+)-catechin and (+)-gallocatechin. The antioxidative activities of each fractions and isolated compounds were done by DPPH radical scavenging test, and all of them were indicated strong antioxidative activities.

• Journal of the Korean Wood Science and Technology
• /
• v.30 no.1
• /
• pp.63-71
• /
• 2002

The bark of P. alba × glandulosa, P. euramericana and P. nigra × maximounczii F₁, several Populus trees, were collected, extracted with acetone-H₂O(7:3, v/v), fractionated with hexane, chloroform and ethylacetate, and freeze dried to give some dark brown powder. Each fraction of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents and then identified by thin layer chromatography using TBA and 6% acetic acid as developing solvents. The structures of the isolated compounds were characterized by ¹H, ¹³C and 2D-NMR tools including mass spectrometry. Most of the compounds were flavonoids and salicin derivatives as follows: (+)-catechin, taxifolin, aromadendrin, eriodictyol, naringenin, sakuranetin, sakuranetin-5-O-𝛽-D-glucopyranoside, neosaturanin, salireposide, p-coumaric acid, and aesculin from P. alba × glandulosa, (+)-catechin, salireposide, populoside and salicortin from P. euramericana and (+)-catechin, quercetin, padmatin, salireposide, populoside and salicortin from P. nigra × maximounczii F₁.