• Title/Summary/Keyword: Flavonol glycoside

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Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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Phytochemical variation of Quercus mongolica Fisch. ex Ledeb. and Quercus serrata Murray (Fagaceae) in Mt. Jiri, Korea - Their taxonomical and ecological implications - (지리산 신갈나무와 졸참나무의 식물화학적 변이 양상 - 분류학적, 생태학적 의미 -)

  • Park, Jin Hee
    • Korean Journal of Environment and Ecology
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    • v.28 no.5
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    • pp.574-587
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    • 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.

Flavonoid Profiles of Quercus mongolica Fisch. ex Ledeb. and Q. serrata Murray (Fagaceae) in Mt. Seorak, Korea: Taxonomical and Ecological Implications (설악산 신갈나무와 졸참나무의 플라보노이드 조성과 분류학적, 생태학적 의미)

  • Park, Jin Hee
    • Journal of Life Science
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    • v.24 no.10
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    • pp.1092-1101
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    • 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.

Antioxidative Activity and Flavonol Glycosides Analysis in Callus Derived from Leaf Tissue of Ginkgo biloba L. (은행(Ginkgo biloba L.)의 잎 유래 캘러스의 항산화능력 및 플로보놀 배당체 검정)

  • Kim, Jung-Suk;Park, Hye-Jeong;Park, Hyeon-Yong
    • Korean Journal of Plant Resources
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    • v.24 no.4
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    • pp.461-471
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    • 2011
  • This study was carried out to establish an in vitro culture method of callus having a high antioxidant activity from Ginkgo biloba L. Leaf explants were cultured on Murashige and Skoog's medium supplemented with various growth regulators. The explants were incubated in the dark or 3,000 lux cool-white light. Methanol extracts from incubated callus were evaluated for scavenging activity of the free radicals using DPPH. The best callus growth rate was achieved in MS medium combined with 10 ${\mu}M$ NAA and 5 ${\mu}M$ kinetin in the light condition. Total antioxidant activity of cell aggregates in suspension culture [MS medium supplemented with 10 ${\mu}M$ NAA in the light] was up to 80% of ascorbic acid. By means of HPLC analysis, quantification of the quercetin dehydrate and keamperol profiles from suspension callus was compared. Contents of quercetin dehydrate and keamperol from leaf extracts were 0.07 and 2.24 ${\mu}g/20{\mu}l$, and those from callus 0.56 and 0.18 ${\mu}g/20{\mu}l$, respectively.

Effect of Mulberry Leaf Sprayed with Rutin and GABA on Silkworm Growth (Rutin 및 GABA 첨식이 누에 성장에 미치는 영향)

  • 방해선;이완주
    • Journal of Sericultural and Entomological Science
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    • v.38 no.2
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    • pp.108-112
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    • 1996
  • This experiment was carried out to investigate the feeding effect of rutin (quercetin-3-o-${\beta}$-rutinoside) and ${\gamma}$-aminobutyric acid(GAB) sprayed on mulberry leaves on silkworm growth. Amount of ingest, digest and feces showed no difference statistically except rutin. Rutin made 6% increase of amount of digest, compared to the control. However, rutin or GABA decreased maximaly silkworm weight by 28% during the experimental period. GABA showed body weight loss by 15%, rutin by 7% respectively, compared to the control. Rutin and GABA extended three days larval period and extended one day mounting period and decreased 15.4% and 91% in number of mounted silkworm compared with the control, respectively.

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Quercetin-3-O-β-D-Glucuronide Suppresses Lipopolysaccharide-Induced JNK and ERK Phosphorylation in LPS-Challenged RAW264.7 Cells

  • Park, Jin-Young;Lim, Man-Sup;Kim, Song-In;Lee, Hee Jae;Kim, Sung-Soo;Kwon, Yong-Soo;Chun, Wanjoo
    • Biomolecules & Therapeutics
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    • v.24 no.6
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    • pp.610-615
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    • 2016
  • Quercetin, a flavonol, has been reported to exhibit a wide range of biological properties including anti-oxidant and anti-inflammatory activities. However, pharmacological properties of quercetin-3-O-${\beta}$-D-glucuronide (QG), a glycoside derivative of quercetin, have not been extensively examined. The objective of this study is to elucidate the anti-inflammatory property and underlying mechanism of QG in lipopolysaccharide (LPS)-challenged RAW264.7 macrophage cells in comparison with quercetin. QG significantly suppressed LPS-induced extracellular secretion of pro-inflammatory mediators such as nitric oxide (NO) and $PGE_2$, and pro-inflammatory protein expressions of iNOS and COX-2. To elucidate the underlying mechanism of the anti-inflammatory property of QG, involvement of MAPK signaling pathways was examined. QG significantly attenuated LPS-induced activation of JNK and ERK in concentration-dependent manners with a negligible effect on p38. In conclusion, the present study demonstrates QG exerts anti-inflammatory activity through the suppression of JNK and ERK signaling pathways in LPS-challenged RAW264.7 macrophage cells.

Anticancer Properties of Icariside II in Human Oral Squamous Cell Carcinoma Cells

  • Kim, In-Ryoung;Kim, Young-Seok;Yu, Su-Bin;Kang, Hae-Mi;Kwak, Hyun-Ho;Park, Bong-Soo
    • International Journal of Oral Biology
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    • v.41 no.1
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    • pp.1-8
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    • 2016
  • OSCC is currently the most common malignancy of the head and neck, affecting tens of thousands of patients per year worldwide. Natural flavonoids from plants are potential sources for novel anti-cancer drugs. Icariin is the active ingredient of flavonol glycoside, which is derived from the medical plant Herba Epimedii. A metabolite of icariin, icariside II exhibits a variety of pharmacological actions, including anti-rheumatic, anti-depressant, cardiovascular protective, and immunomodulatory functions. However, the exact mechanism causing the apoptosis-inducing effect of icariside II in OSCC is still not fully understood. In the present study, we assessed the anti-cancer effect of icariside II in OSCC cell lines by measuring its effect on cell viability, cell proliferation, and mitochondria membrane potential (MMP). Icariside II treatment of OSCC cells resulted in a dose- and time-dependent decrease in cell viability. Hoechst staining indicated apoptosis in icariside II-treated HSC cells. Icariside II inhibited cell proliferation and induced apoptosis in HSC cells, with significant increases in all present parameters in HSC-4 cells. The results clearly suggested that icariside II induced apoptosis via activation of intrinsic pathways and caspase cascades in HSC-4 cell lines. The collective findings of the study suggested that Icariside II is a potential treatment for OSCC; in addition, the data could provide a basis for the development of a novel anti-cancer strategy.

Constituents of Flowers of Carthamus tinctorius L. and Their Antioxidant Activity (홍화의 성분 분리 및 항산화 활성)

  • Choi, Hyun-Gyu;Jiang, Yan-Fu;Park, Sung-Hee;Son, Ae-Ryang;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.42 no.2
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    • pp.110-116
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    • 2011
  • As part of our ongoing study focused on the discovery of antioxidants from natural products by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, methanol extract of flowers of Carthamus tinctorius L. was found to show potent antioxidant activity. Activity-guided fractionation of the methanol extract lead to the isolation of twenty compounds including two flavonol glycosides, quercertin-3-O-${\beta}$-D-glucopyranoside (12) and kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl-${\beta}$-D-glucopyranoside (18), two flavanone glycosides, (2S)-4',5,6,7-tetrahydroxyflavanone 6-O-${\beta}$-D-glucopyranoside (15) and (2R)-5,7,8',4-tetrahydroxyflavanone 8-O-${\beta}$-D-glucopyranoside (16), and two acetylenic glycosides, 8Z-decaene-4,6-diyne-1-O-${\beta}$-D-glucopyranoside (13) and 4,6-decadiyne-1-O-${\beta}$-D-glucopyranoside (14). Their chemical structures were identified by using spectroscopic analysis. Among them, compounds 12-18 were tested in DPPH assay. Compounds 13-16 were first reported to their antioxidant activity. Quercertin-3-O-${\beta}$-D-glucopyranoside (12) showed the most potent inhibitory effect on DPPH with $IC_{50}$ value of 56.7 ${\mu}M$.

Neuroprotective Effects of Ginkgo biloba extract, GBB, in the Transient Ischemic Rat Model

  • Oh, Jin-Kyung;Jung, Ji-Wook;Oh, Hye-Rim;Han, Yong-Nam;Ryu, Jong-Hoon
    • Biomolecules & Therapeutics
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    • v.15 no.3
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    • pp.169-174
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    • 2007
  • In the present study, we investigated the neuroprotective effects of standardized Ginkgo biloba extract (GBB) (total terpene trilactones, 13 ${\pm}$ 3%; biflavone, 4.5 ${\pm}$ 1.5%; flavonol glycoside, < 8%; proanthocyanidine, under detection limit) on ischemia-reperfusion-induced brain injury in the rats. Ischemia was induced by the intraluminal occlusion of the right middle cerebral artery for 2 h and reperfusion was continued for 22 h. GBB was orally administered, promptly prior to reperfusion and 2 h after. Total infarction volume in the ipsilateral hemispheres of ischemia-reperfusion rats were significantly reduced by treatment with GBB in a dose-dependent manner (P<0.05). The therapeutic time window of GBB was 3 h in this ischemia-reperfusion rat model. Furthermore, GBB also significantly inhibited increased neutrophil infiltration of ischemic brain tissue, as estimated by myeloperoxidase activity. These findings suggest that GBB plays a crucial protective role in ischemia-induced brain injury, in part, via inhibition of neutrophil infiltration, and suggest that this GBB could serve as a neuroprotective agent following transient focal ischemic brain injury.