• 제목/요약/키워드: Glucopyranoside

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Hepatoprotective constituents from Beta vulgaris var. cycla

  • Kim, In-Kyum;Chin, Young-Won;Song, Won-Lim;Yang, Hye-Kyung;Kim, Young-Choong;Kim, Jin-Woong
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.259.1-259.1
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    • 2003
  • In the course of hepatoprotective screening for domestic plants. the aerial parts of B. vulgaris var. cycla exhibited hepatoprotective activity which was determined by using the primary cultures of rat hepatocytes injured by H2O2. Bioactivity-guided separation for this plant gave a new flavonoid (1) and the known compounds (2-4), which structures were elucidated by 1H-NMR, HMQC, 1H-1H COSY and HMBC as compound 1, apigenin 8-C-, 7-O-di-$\beta$-D-glucopyranoside, compound 2, vitexin 2"-O-$\beta$-D-glucopyranoside, compound 3, (+)-dehydrovomifoliol, and compound 4, 3-hydroxy-5$\alpha$, 6$\alpha$-epoxy-$\beta$-ionone.

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Steroidal Saponins from Dracaena humilis (Dracaenaceae) and their Chemotaxonomic Significance

  • Mouzie, Cedric Mbiesset;Ponou, Beaudelaire Kemvoufo;Fouedjou, Romuald Tematio;Teponno, Remy Bertrand;Tapondjou, Leon Azefack
    • Natural Product Sciences
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    • 제27권2호
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    • pp.122-127
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    • 2021
  • A new steroidal saponin, (23S,24S)-spirosta-5,25(27)-diene-1𝛽,3𝛽,23,24-tetrol 1-O-((2,3-diacetyl-α-L-rhamnopyranosyl)-(1→2)-[𝛽-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside)-24-O-𝛽-D-glucopyranoside (humilisoside) together with the known 𝛽-sitosterol 3-O-glucopyranoside, adenosine, dioscin, and methylprotodioscin were isolated from the leaves of Dracaena humilis. Their structures were elucidated by spectral techniques including mass spectrometry (ESIMS, HRESIMS, tandem MS-MS), 1D NMR (1H, 13C NMR), 2D NMR (HSQC, 1H-1H COSY, HMBC, NOESY), chemical method as well as by comparison with spectroscopic data reported in the literature. The chemotaxonomic significance of the isolation of these compounds is discussed. This is the first report on the phytochemical investigation of D. humilis.

연잎에서 DPPH 라디칼 소거활성을 가지는 페놀성 화합물의 분리 (Phenolic Compounds from the Leaves of Nelumbo nucifera Showing DPPH Radical Scavenging Effect)

  • 박찬흠;허종문;송경식;박종철
    • 생약학회지
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    • 제38권3호통권150호
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    • pp.263-269
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    • 2007
  • Nelumbo nucifera (Nymphaeaceae) has been widely used in a traditional oriental medicine to treat bleeding, fever, diarrhea, hemorrhoid, sunstroke, dysentery and dizziness. The leaves of this plant were refluxed with methanol, and then fractionated with organic solvents to screen the antioxidant activity using DPPH radical. Ethyl acetate and n-butanol fractions showed good DPPH radical scavenging effects and were carried out column chromatographies to isolate nine compounds. Their chemical structures were characterized as p-hydroxybenzoic acid (1), uracil (2), luteolin (3), quercetin $3-O-{\beta}-D-glucopyranoside$ (4), $rhamnetin 3-O-{\beta}-D-glucopyranoside$ (5), $isorhamnetin 3-O-{\beta}-D-glucopyranoside$ (6), $quercetin 3-O-{\beta}-D-glucuropyranoside$ (7), $quercetin 3-O-{\beta}β-D-xylofuranosyl(1{\rightarrow}2)-{\beta}-D-galactopyranoside$ (8), and adenine (9) by comparison NMR spectral data and with those in references. Compounds 1, 2, 5 and 9 were firstly isolated from this plant. Compounds 1, 3 and 4 showed potent DPPH radical scavenging activity. Especially, compound 3, luteolin showed the higher effect than ascorbic acid used as a positive control.

Radical Scavenging Constituents of Cyperus flaccidus

  • Ahn, Dal-Rae;Lee, Hyun-Jin;Xing, Ming Ming;Tao, Chao;Lee, Eun-Byeol;Lee, Tae-Gwan;Shin, Tae-Yong;Eun, Jae-Soon;Jeon, Hoon;Lim, Jong-Pil;Kim, Dae-Keun
    • Natural Product Sciences
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    • 제18권2호
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    • pp.111-115
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    • 2012
  • In the course of screening for antioxidant compounds by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging effect and superoxide quenching activity, methanol extract of Cyperus flaccidus (Cyperaceae) was found to show potent antioxidant activities. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of ten compounds, kaempferol-3,7-O-${\alpha}$-L-dirhamnopyranoside (1), caffeic acid (2), quercetin-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (3), kaempferol-3-O-${\alpha}$-L-rhamnopyranoside (4), quercetin-3-O-${\alpha}$-L-rhamnopyranoside (5), luteoiln-7-O-${\beta}$-D-glucopyranoside (6), kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (7), luteoiln (8), quercetin (9) and quercetin-3-O-${\beta}$-D-glucuronide (10). Their structures were elucidated by spectroscopic studies. Compounds 1 - 10 were isolated for the first time from this plant. Among them, compounds 2, 8 and 9 showed the significant radical scavenging effects on DPPH, and the potent xanthine-originated superoxide quenching activities.

수치에 의한 황금의 성분변화 (Change of Flavonoid Composition in Scutellaria baicalensis by Processing)

  • 김장희;양기숙;김태희
    • 약학회지
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    • 제43권1호
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    • pp.16-22
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    • 1999
  • Scutellaria baicalensis Georgi (Labiatae) has been extensively used in treatment of diarrhea, conjunctivitis, gastritis, enteritis and skin disease. As instructed in old description, the Scutellariae Radix should sometimes be processed before use. To 노디 light on the changes of chemical compositions by processing as well as processing method-activity relationships, Scutellariae Radix was heated at 16$0^{\circ}C$-20$0^{\circ}C$ for 30 min. in furnace or soaked with 20% EtOH (SPE) and boy's urine(SPU), respectively, which are one of processing methods and then heated at 17$0^{\circ}C$ for 30 min. To isolate the chemical components, Scutellariae Radix with/without processing were extracted with EtOH and EtOH extract was fractionated with ether, ethyl acetate and butanol to give respective fractions. Ether and EtOAc fractions obtained from the processed drug with urine (SPU) were subjected to chromatography to obtainsix components, oroxylin A, Wogonin, chrysin, baicalein, baicalein 7-O-$\beta$-D-glucopyranoside and $\beta$-sitosterol 3-O-$\beta$-D-glucopyranoside. All the isolated compounds were identified by means of physicochemical and spectroscopic methods (IR, $^1H-NMR,{\;}^13C-NMR$, Mass). By HPLC determination, the changes of the contents for each isolated components from SPE and SPU samples were observed. It was found that the content of nonglycosidic flavones such as oroxylin A, wogonin, chrysin and baicalein was increased markedly, whereas the content of baicalin and baicalein 7-O-$\beta$-D-glucopyranoside was significantly decreased in both samples as compared with those of Scutellariae Radix. When the sample was soaked with boy's urine, the total amount of nonglycosidic flavones was higher than that of processing with 20% EtOH.

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[ $\beta$ ]-Secretase (BACE1) Inhibitors from Sanguisorbae Radix

  • Lee, Hee-Ju;Seong, Yeon-Hee;Bae, Ki-Hwan;Kwon, Soon-Ho;Kwak, Hye-Min;Nho, Si-Kab;Kim, Kyung-A;Hur, Jong-Moon;Lee, Kyung-Bok;Kang, Young-Hwa;Song, Kyung-Sik
    • Archives of Pharmacal Research
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    • 제28권7호
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    • pp.799-803
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    • 2005
  • In the course of screening anti-dementia agents from natural products, two $\beta$-secretase (BACE1) inhibitors were isolated from the ethyl acetate soluble fraction of Sanguisorbae Radix by the activity-guided purification using silica gel, Sephadex LH-20, and RP-HPLC. They were identified as 1,2,3-trigalloyl-4,6-hexahydroxydiphenoyl-$\beta$-D-glucopyranoside (Tellimagrandin II, 1) and 1,2,3,4,6-pentagalloyl-$\beta$-D-glucopyranoside (2) and were shown to non-competitively inhibit $\beta$-secretase (BACE1) with the $IC_{50}$ values of $3.10{\times}10^{-6}M\;and\;3.76{\times}10^{-6}M$, respectively. The Ki values of 1 and 2 were $6.84{\times}10^{-6}M\;and\;5.13{\times}10^{-6}M$. They were less inhibitory to asecretase (TACE) and other serine proteases such as chymotrypsin, trypsin, and elastase, suggesting that they were relatively specific inhibitors of BACE1.

가지(Solanum melongena L.) 잎으로부터 페놀 화합물의 분리 및 동정 (Phenolic compounds from the leaves of eggplant (Solanum melongena L.))

  • 백동렬;이민지;백남인;서경화;이윤형
    • Journal of Applied Biological Chemistry
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    • 제59권2호
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    • pp.103-106
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    • 2016
  • 가지 잎으로부터 3종의 phenylpropanoid, 1종의 flavonoid glycoside, 그리고 1종의 norsesquiterpenoid glycoside 화합물을 분리 동정하였다. 가지 잎을 80 % MeOH로 추출하였으며, 얻어진 추출물을 n-hexane, EtOAc, n-BuOH 및 물 층으로 계통분획을 실시하였다. 이 중 n-BuOH 분획에 대하여 $SiO_2$, ODS 및 Sephadex LH-20 column chromatography를 반복 실시하여 5종의 화합물을 분리, 정제하였다. Nuclear magnetic resonance, infrared spectroscopy 및 mass spectrometry의 spectroscopic data를 해석하여 이 화합물들을 caffeic acid (1), chlorogenic acid (2), cryptochlorogenic acid (3), panasenoside (4), 및 (6R,7E,9R)-4,7-megastigmadien-3-one-9-${\beta}$-${\small{D}}$-glucopyranoside (5) 로 각각 동정하였다. 본 연구에서 화합물 3과 4는 가지 잎에서 처음으로 분리, 동정하였다.

덜꿩나무(Viburnum erosum)줄기로부터 이차대사산물의 분리 및 동정 (Identification of Secondary Metabolites from the Stems of Viburnum erosum)

  • 인서지;서경화;송나영;송명종;백남인
    • Journal of Applied Biological Chemistry
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    • 제57권2호
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    • pp.165-170
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    • 2014
  • 덜꿩나무(Viburnum erosum) 줄기를 실온에서 80% MeOH 수용액으로 추출하고 농축하였다. 이 추출물을 EtOAC, n-BuOH, 및 $H_2O$ 분획으로 나누었다. 이 중 EtOAc및 n-BuOH 분획에 대하여 $SiO_2$, ODS 및 Sephadex LH-20 column chromatography를 반복 수행하여 4종의 화합물을 분리, 정제하였다. 분리한 화합물의 구조는 NMR, IR, 및 MS data를 해석하여, betulinic aldehyde (1), koaburside (2), (6R,7E,9R)-9-hydroxymegastigma-4,7-dien-3-one-9-O-${\beta}$-D-glucopyranoside (3), 그리고 byzantionoside B (4)로 구조를 결정하였다. 분리된 화합물 모두 덜꿩나무에서는 처음으로 분리되었다.

고로쇠 Coumarinolignan의 β-Cyclodextrin 포접화합물 제조 및 암세포증식 억제활성 (Anti-Proliferative Effects of β-Cyclodextrin Inclusion Complexes with Coumarinolignans from Acer mono)

  • 임순호;정다운;윌리엄스다렌;게클러커트;김경근;신부안;이익수;김현정
    • 생약학회지
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    • 제46권2호
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    • pp.133-139
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    • 2015
  • Two coumarinolignans, cleomiscosins C (1) and D (2) were isolated from the heartwood of Acer mono, together with four compounds, 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (3), 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-apiofuranosyl-(1$\rightarrow$6)-${\beta}$-D-glucopyranoside (4), scopoletin (5), and (E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (6). Of them, cleomiscosins C (1) and D (2) were applied to preparing inclusion complex molecules with ${\beta}$-cyclodextrin (${\beta}$-CD) to improve the very poor solubility in cell media. The CD complexes of 1 and 2 exhibited an enhancement of water solubility which is feasible to measure their cytotoxicity using a spectrophotometer in a cell-based assay. Anti-proliferative activity of these complex molecules was successfully estimated on HCT116 human colon cancer cells, and cleomiscosin D (2) showed anti-proliferative effects at the concentration of 1.95~31.2 ${{\mu}g}$/mL in a dose-dependent manner.