• Title/Summary/Keyword: 7-O-{\beta}-D-glucoside$

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Flavonoids from Salix hallaisanensis Leaves (떡버들 잎의 플라보노이드)

  • Oh, Mi-Hyun;Ham, In-Hye;Chung, Sung-Hee;Whang, Wan-Kyun
    • Korean Journal of Pharmacognosy
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    • v.36 no.4 s.143
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    • pp.282-290
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    • 2005
  • The MeOH extract of the the leaves of Salix hallaisanensis (Salicaceae) was partitioned successively with $CHCl_3$, 20% MeOH, 40% MeOH and 60% MeOH solution. From the fractions obtained, 9 compounds were isolated, $diosmetin-7-O-{\beta}-d-glucoside$ (I), $diosmetin-7-O-{\beta}-D-glucosyl-(1{\rightarrow)6)-{\beta}-d-glucoside$ (II), $diosmetin-7-O-{\beta}-d-xylosyl-(1{\rightarrow}6)-{\beta}-D-glucoside$ (III), $quercetin-3-O-{\beta}-d-galactoside$ (hyperoside) (IV), $quercetin-3-O-{\alpha}-l-rhamnosyl-(1{\rightarrow}6)-{\beta}-D-glucoside(rutin)$ (V), luteolin (VI), $luteolin-7-O-{\beta}-d-glucoside$ (VII), $kaempferol-3-O-{\alpha}-l-rhamnosyl-(1{\rightarrow}6)-{\beta}-D-glucoside$ (VIII), and (+)-catechin (IX).

Isoflavone Compounds of the Heartwood of Maackia fauriei (솔비나무(Maackia fauriei)의 이소플라본 화합물)

  • Hwang, Myoung-Hui;Kwon, Yong-Soo;Kim, Chang-Min
    • YAKHAK HOEJI
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    • v.41 no.4
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    • pp.444-449
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    • 1997
  • Five flavonoids were isolated from the heartwoods of Maackia fauriei. On the basis of spectroscopic evidences, the structure of these compounds were established as (-)maa ckiain(3-hydroxy-8,9-methylenedioxypterocarpan), ononin(4'-methoxyisoflavone- 7-O-${\beta}$-D-glucoside), wistin(4',6-dimethoxyisoflavone-7-O-${\beta}$-D-glucoside), daidzin(4'-hydroxyisoflavone-7-O-${\beta}$-D-glucoside) and 2'-methoxy-4'- hydroxyisoflavone-6-O-${\beta}$-D-glucoside. In these compounds, 2'-methoxy-4'-hydroxyisoflavone-6-O-${\beta}$-D-glucoside was for the first time isolated from the plant source.

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Active Oxygen Scavenging Activity of Luteolin-7-O-$\beta$-D-Glucoside Isolated from Humulus japonicus (환삼덩굴로부터 분리한 Luteolin-7-O-$\beta$-D-Glucoside의 활성산소 소거능)

  • 정신교;박승우;박종철
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.29 no.1
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    • pp.106-110
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    • 2000
  • We investigated the active oxygen scavenging activity and active compound from Humulus japonicus. The ethyl acetate and butanol fraction exhibited strong scavenging effects on hydroxyl radical. Furthermore active compound was isolated and purified using Amberlite XAD-2 column chromatography and preparative HPLC from ethyl acetate fracton, and major compound was identified as a luteolin-7-O-$\beta$-D-glucoside by the MS, UV, 1H-NMR and 13C-NMR analyses. Luteolin-7-O-$\beta$-D-glucoside exhibited strong scavenging effect on active oxygens such as superoxide radical, hydroxyl radical and hydrogen peroxide.

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Glucosylation of Isoflavonoids in Engineered Escherichia coli

  • Pandey, Ramesh Prasad;Parajuli, Prakash;Koirala, Niranjan;Lee, Joo Ho;Park, Yong Il;Sohng, Jae Kyung
    • Molecules and Cells
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    • v.37 no.2
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    • pp.172-177
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    • 2014
  • A glycosyltransferase, YjiC, from Bacillus licheniformis has been used for the modification of the commercially available isoflavonoids genistein, daidzein, biochanin A and formononetin. The in vitro glycosylation reaction, using UDP-${\alpha}$-D-glucose as a donor for the glucose moiety and aforementioned four acceptor molecules, showed the prominent glycosylation at 4' and 7 hydroxyl groups, but not at the $5^{th}$ hydroxyl group of the A-ring, resulting in the production of genistein 4'-O-${\beta}$-D-glucoside, genistein 7-O-${\beta}$-D-glucoside (genistin), genistein 4',7-O-${\beta}$-D-diglucoside, biochanin A-7-O-${\beta}$-D-glucoside (sissotrin), daidzein 4'-O-${\beta}$-D-glucoside, daidzein 7-O-${\beta}$-D-glucoside (daidzin), daidzein 4', 7-O-${\beta}$-D-diglucoside, and formononetin 7-O-${\beta}$-D-glucoside (ononin). The structures of all the products were elucidated using high performance liquid chromatography-photo diode array and high resolution quadrupole time-of-flight electrospray ionization mass spectrometry (HR QTOF-ESI/MS) analysis, and were compared with commercially available standard compounds. Significantly higher bioconversion rates of all four isoflavonoids was observed in both in vitro as well as in vivo bioconversion reactions. The in vivo fermentation of the isoflavonoids by applying engineered E. coli $BL21(DE3)/{\Delta}pgi{\Delta}zwf{\Delta}ushA$ overexpressing phosphoglucomutase (pgm) and glucose 1-phosphate uridyltransferase (galU), along with YjiC, found more than 60% average conversion of $200{\mu}M$ of supplemented isoflavonoids, without any additional UDP-${\alpha}$-D-glucose added in fermentation medium, which could be very beneficial to large scale industrial production of isoflavonoid glucosides.

Chemical Constituents of Gomphrena globosa. II

  • Dinda, Biswanath;Ghosh, Biplab;Achari, Basudev;Arima, Shiho;Sato, Nariko;Harigaya, Yoshihiro
    • Natural Product Sciences
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    • v.12 no.2
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    • pp.89-93
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    • 2006
  • One new sterol glucoside, $gomphsterol\;{\beta}-D-glucoside$ 1 along with known compounds, ${\beta}-sitosterol$, stigmasterol, campesterol, $stigmasterol-{\beta}-D-glucoside$, friedelin, 3-epi-friedelinol, allantoin, and $chrysoeriol-7-O-{\beta}-D-glucoside$ have been isolated from the aerial parts of Gomphrena globosa (Amaranthaceae). On the basis of spectroscopic (including 2D NMR) and chemical studies, the structure of 1 was elucidated as $(22E,24S)-24-ethylcholesta-7,9(11),22-trien-3{\beta}-ol-3-O-{\beta}-D-glucopyranoside$. Known compounds are reported for the first time from this plant species.

Effects of Compounds Isolated from Ainsliaea acerifolia on the Hepatic Alcohol Dehydrogenase Activity (단풍취로부터 분리한 Apigenin $7-O-{\beta}-D-glucoside$가 알콜대사효소에 미치는 영향)

  • Zee, Ok-Pyo;Shin, Mal-Shick;Moon, Hyung-In
    • Applied Biological Chemistry
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    • v.42 no.2
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    • pp.162-165
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    • 1999
  • Effects of compounds isolated from Ainsliaea acerifolia on alcohol metabolism in rats were examined and the results were as follows: Apigenin $7-O-{\beta}-D-glucoside$, after a single oral administration to rats, was found to cause a significant decrease in the serum ethanol concentration as well as enhancement of liver cytosolic alcohol dehydrogenase(ADH) activity.

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Phytochemical Studies on Astragalus Root (2);Flavonoids and a Lignan

  • Lee, Eun-Ju;Yean, Min-Hye;Jung, Hye-Sil;Kim, Ju-Sun;Kang, Sam-Sik
    • Natural Product Sciences
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    • v.14 no.2
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    • pp.131-137
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    • 2008
  • From the 70% EtOH extract of the roots of Astragalus membranaceus (Leguminosae), eleven flavonoid derivatives and a lignan, were isolated and identified as liquiritigenin (1), daidzein (2), formononetin (3), sophorophenolone (4), calycosin (5), methylnissolin (6), isomucronulatol (7), isomucronulatol 7-O-glucoside (8), methylnissolin 3-O-glucoside (9), calycosin 7-O-glucoside (10), (+)-syringaresinol O-${\beta}$-D-glucoside (11), and isomucronulatol 7,2'-di-O-glucoside (12), by spectroscopic methods. This is the second report of the isoflavonoid derivatives sophorophenolone (4) and isomucronulatol 7,2'-di-O-glucoside (12) from a natural source, as well as the first report of compounds liquiritigenin (1), daidzein (2) and (+)-syringaresinol O-${\beta}$-D-glucoside (11) from the species A. membranaceus.

Nitric Oxide Inhibitory Constituents from Fruits of Opuntia humifusa

  • Kang, You-Jeng;Kim, Hae-Young;Lee, Chul;Park, So-Young
    • Natural Product Sciences
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    • v.20 no.3
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    • pp.211-215
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    • 2014
  • Opuntia humifusa, also called as Cheonnyuncho, is a cactus widely cultivated in southern regions of Korea. It has been known to have diverse biological activities, but most of the studies were performed with the MeOH extracts or solvent-partitioned fractions. Furthermore, the efforts to identify the responsible compounds for the biological activities are very limited. In this study, we tested the inhibitory effect of extracts and solvent-partitioned fractions of O. humifusa against LPS-induced nitric oxide (NO) production in Raw264.7 cells. The butanol fractions of O. humifusa efficiently inhibited the production of NO in Raw264.7 cells, but it was not due to the reduction of cell viability. Bioassay-guided isolation of butanol fractions of O. humifusa allowed the isolation of three flavonoids isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1), isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) and isorhamnetin 3-O-${\beta}$-$\small{D}$-(6-O-${\alpha}$-$\small{L}$-rhamnosyl)glucoside (3), and one lignan syringaresinol O-${\beta}$-$\small{D}$-glucopyranoside (4). Among them, isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1) and isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) exhibited the moderate inhibitory effects against LPS-induced NO production. This is the first time to report anti-inflammatory effects of these compounds.

Antioxidative Flavonoids from Leaves of Carthamus tinctorius

  • Lee, Jun-Young;Chang, Eun-Ju;Kim, Hyo-Jin;Park, Jun-Hong;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.313-319
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    • 2002
  • A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

Inhibitory Effects of Kaempferol-7-O-β-D-glucoside on LPS-induced NO, PGE2 and Inflammatory Cytokines Production in RAW264.7 Macrophages (LPS유도 대식세포에서 Kaempferol-7-O-β-D-glucoside의 NO, PGE2 및 염증성 사이토카인 생성 저해 효과)

  • Park, Jong Cheol;Han, Hee-Soo;Lee, Seung-Bin;Lee, Kyung-Tae
    • Korean Journal of Pharmacognosy
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    • v.47 no.4
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    • pp.295-300
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    • 2016
  • Flavonoids are widely reported to be beneficial to human health. Among flavonoids, in general, flavonoid aglycons have better biological activities than flavonoid glycosides, in that aglycons can easily penetrate through cell membrane because of their low polarity. Therefore, kaempferol, quercetin and various their glycosides were evaluated for their abilities to inhibit NO and $PGE_2$ productions in LPS-induced RAW 264.7 cells. Of these flavonoids and flavonoid glycosides, kaempferol-7-O-${\beta}$-D-glucoside(kp-7-glu) which possesses a glycoside at C-7 position of the A ring in kaempferol, potently inhibited NO, $PGE_2$ and $TNF-{\alpha}$, $IL-1{\beta}$, IL-6 productions in LPS-induced RAW 264.7 macrophages.