• Title/Summary/Keyword: glucoside

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Flavonoids from the Flower of Clerodendrum trichotomum (누리장나무 꽃의 Flavonoid 성분)

  • Lee, Jong-Wook;Kang, Se Chan;Bae, Jong Jin;Lee, Kyung Bok;Kwak, Jong Hwan
    • Korean Journal of Pharmacognosy
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    • v.46 no.4
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    • pp.289-294
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    • 2015
  • Seven flavonoids were isolated from the flower of Clerodendrum trichotomum. Their structures were identified as apigenin (1), genistein (2), chrysoeriol (3), genistein 7-O-glucoside (4), kaempferol 3-O-glucoside (5), isorhamnetin 3-O-glucoside (6) and apigenin 7-O-glucoside (7) on the basis of spectral data. These compounds were isolated from C. trichotomum for the first time. The antioxidant activity of compounds 1-7 were evaluated by the ORAC (oxygen radical absorbance capacity) assay, and the ORAC values were expressed as relative trolox equivalent. All isolated compounds exhibited antioxidant activity.

A Phenolic Glucoside Isolated from Prunus serrulata var. spontanea and its Peroxynitrite Scavenging Activity

  • Jung Hyun Ah;Chung Hae Young;Kang Sam Sik;Hyun Sook Kyung;Kang Hye Sook;Choi Jae Sue
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1127-1130
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    • 2005
  • A new phenolic glucoside (1), pursargentoside, was isolated from the leaves of Prunus serrulata var. spontanea, along with three other known compounds, orobol 7-O-glucoside (2), $1{\beta}$, $2{\alpha}$, $3{\alpha}$, 24-tetrahydroxy-urs-12-en-28-oic acid (3), and chlorogenic acid (4). The structure of pursargentoside (1) was identified by spectroscopic data analysis including 1D and 2D NMR spectroscopy, as 2-O-${\beta}$-(6'-benzoyl)-glucopyranosyl o-(Z)-coumaric acid. Compounds 1, 2, and 4 exhibited ONOO- scavenging activity, whereas compound 3 was determined to be virtually inactive.

Extractives from Wood of Euonymus japonica (사철나무(Euonymus japonica) 목부의 추출성분)

  • Kim, Woo-Jin;Lee, Kyoung-Tae;Lee, Hak-Ju;Cho, Sung-Taig
    • Journal of Korean Society of Forest Science
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    • v.103 no.1
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    • pp.113-121
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    • 2014
  • From the bark of Euonymus japonica, ten compounds were isolated by column chromatography and identified as follows. The structures were determined as : (-)-epicatechin, (-)-epigallocatechin, vanillic acid, 2,4-dimethoxyphenol-1-glucoside, 2, 4, 6-trimethoxyphenol-glucoside, 5-caffeoylquinic acid, 4-caffeoyuinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 1, 5-dicaffeoylquinic acid.

A New Stereoisomeric Monoterpene Glycoside from Clematis heracleifolia leaves

  • Kim, Mi Ae;Yang, Heejung;Kim, Myong Jo;Chun, Wanjoo;Kwon, Yongsoo
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.107-110
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    • 2016
  • A new stereoisomeric monoterpene glycoside and five already-known compounds were isolated from the n-BuOH soluble fraction of Clematis heracleifolia leaves. On the basis of spectral data, the structures of the isolated compounds were identified as protocatechuic acid (1), ferulic acid (2), caffeic acid (3), aesculin (4), (6Z)-9-hydroxylinaloyl glucoside (5), and 9-hydroxylinaloyl glucoside (6) and these were isolated for the first time from this plant. Among these compounds, (6Z)-9-hydroxylinaloyl glucoside (5) is a newly isolated from plant source.

The Chemical Structures and Their Antioxidant Activity of the Components Isolated from the Heartwood of Hemiptelea davidii (시무나무(Hemiptelea davidii) 심재의 성분과 그 항산화 활성)

  • Chang, Bok-Sim;Kwon, Yong-Soo;Kim, Chang-Min
    • Korean Journal of Pharmacognosy
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    • v.35 no.1 s.136
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    • pp.80-87
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    • 2004
  • From the $CHCl_3$ and BuOH soluble fractions of the heartwood of Hemiptelea davidii, eleven compounds have been isolated. On the basis of spectral data, they were identified as ${\beta}-sitosterol$ (1), scopoletin (2), kaempferol (3), 4-hydroxybenzoic acid (4), 2-(4-hydroxyphenyl) ethanol (5), aromadendrin (6), scopolin (7), kaempferol 6-C-glucoside (8), aromadendrin 6-C-glucoside (9), taxifolin 6-C-glucoside (10) and quercetin 6-C-glucoside (11), respectively. Among these compounds, compounds 3, 8, 10, and 11 showed potent DPPH radical scavenging activity with $IC_{50}$ values of 11.9, 14.7, 10.3 and $6.2\;{\mu}g/ml$, respectively.

The Chemical Constituents and Their Pharmacological Activities of Endemic Medicinal Plants in Korea -Pharmacologically Active Constituents of Fraxinus Species- (한국 특산 생약의 약효성분 및 약리활성 -Fraxinus spp.의 약효 성분-)

  • Kim, Il-Hyuk;Kim, Chang-Johng;Yook, Chang-Soo
    • Korean Journal of Pharmacognosy
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    • v.24 no.3
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    • pp.197-202
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    • 1993
  • Three components, fraxetin-8-glucoside, esculetin-6-glucoside and mannitol, were isolated from the stem bark of Fraxinus chiisanensis var. stenophylla, F. japonica var. intermedia and F. densata. The MeOH extract of the cortex of F. densata had the antiinflammatory activity on the carrageenin-induced paw edema in rat. The MeOH extracts of the cortex of all three Fraxinus spp. have the potent analgesic activity on the HOAc-induced writhing syndrome in mouse and the hepatoprotective activity on the $CCl_4-induced$ fatty liver in rat: protection of ballooning formation and inhibition of sGPT and sGOT increased by $CCl_4$.

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Flavone Glucosides from the Leaves of Helianthus tuberosus

  • Chae, Sung-Wook;Lee, Sang-Hyun;Kang, Sam-Sik;Lee, Ho-Jin
    • Natural Product Sciences
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    • v.8 no.4
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    • pp.141-143
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    • 2002
  • Two flavone glucosides have been isolated from the leaves of Helianthus tuberosus (jerusalem artichoke). Their structures were identified as kaempferol 3-O-glucoside (1) and quercetin 7-O-glucoside (2) by spectroscopic analysis and confirmed by comparison with reported data. These flavonoids were isolated for the first time from this plant part.

Comparative Study of the Inhibitory Effect of Luteolin and Luteolin-7-Glucoside on Rat Aortic Vascular Smooth Muscle Cell Proliferation

  • Kim, Jin-Ho;Kim, Soo-Yeon;Lim, Yong;Pyo, Hyeong-Bae;Park, Byeoung-Soo;Yoo, Hwan-Soo;Yun, Yeo-Pyo
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.102.2-103
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    • 2003
  • It has been previously reported that luteolin and luteolin-7-glucoside displayed the potent anti-oxidant and anti-inflammatory effects, which have also been successful in reducing vascular smooth muscle cells(VSMCs) proliferation. In this study, a possible anti-proliferative effect and its mechanism on rat aortic VSMCs by luteolin and luteolin-7-glucoside were investigated. Luteolin significantly inhibited the platelet-derived growth factor(PDGF)-BB-induced proliferation of rat aortic VSMCs. While luteolin-7-glucoside weakly inhibited the proliferation. (omitted)

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Rapid Isolation of Cyanidin 3-Glucoside and Peonidin 3-Glucoside from Black Rice (Oryza sativa) Using High-Performance Countercurrent Chromatography and Reversed-Phase Column Chromatography

  • Jeon, Heejin;Choi, Janggyoo;Choi, Soo-Jung;Lee, Chang Uk;Yoon, Shin Hee;Kim, Jinwoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.21 no.1
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    • pp.30-33
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    • 2015
  • Anthocyanins are water soluble plant pigments which are responsible for the blue, red, pink, violet colors in several plant organs such as flowers, fruits, leaves and roots. In recent years, anthocyanin-rich foods have been favored as dietary supplements and health care products due to diverse biological activities of anthocyanins including antioxidant, anti-allergic, anti-diabetic, anti-microbial, anti-cancer and preventing cardiovascular disease. High-performance countercurrent chromatography (HPCCC) coupled with reversed-phase medium pressure liquid chromatography (RP MPLC) method was applied for the rapid and efficient isolation of cyanidin 3-glucoside (C3G) and peonidin 3-glucoside (P3G) from black rice (Oryza sativa L., Poaceae). The crude black rice extract (500 mg) was subjected to HPCCC using two-phase solvent system composed of tert-butyl methyl ether/n-butanol/ acetonitrile/0.01% trifluoroacetic acid (TBME/B/A/0.01% TFA, 1 : 3 : 1 : 5, v/v, flow rate - 4.5 mL/min, reversed phase mode) to give enriched anthocyanin extract (37.4 mg), and enriched anthocyanin extract was sequentially chromatographed on RP-MPLC to yield C3G (16.5 mg) and P3G (8.7 mg). The recovery rate and purity of isolated C3G were 76.0% and 98.2%, respectively, and those of P3G were 58.3% and 96.3%, respectively. The present study indicates that HPCCC coupled with RP-MPLC method is more rapid and efficient than multi-step conventional column chromatography for the separation of anthocyanins.

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.