• Title/Summary/Keyword: Glucopyranoside

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Antioxidant Components of the Aerial Parts of Bidens frondosa L. (미국가막사리 지상부의 항산화 성분)

  • Ahn, Dalrae;Kim, Dae Keun
    • Korean Journal of Pharmacognosy
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    • v.47 no.2
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    • pp.110-116
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    • 2016
  • As a part of an ongoing search for natural plants with antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH), a total extract of the aerial parts of Bidens frondosa L. (Compositae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of five compounds, quercetin-3-O-${\beta}$-D-glucopyranoside (1), luteolin-7-O-${\beta}$-D-glucopyranoside (2), 7,8,3',4'-tertrahydroxy-flavanone (3), okanin-4-O-${\beta}$-D-glucopyranoside (4), and okanin (5). Their structures were elucidated by spectroscopic studies. Compounds 3-5 were isolated for the first time from this plant. Among them, compounds 3 and 5 showed the significant radical scavenging effects on DPPH, and compounds 3 and 5 also showed the potent riboflavin and xanthine originated superoxide quenching activities.

A New Acetophenone of Aerial Parts from Rumex aquatica

  • Yoon, Hwan-Min;Park, Ji-Yeun;Oh, Mi-Hyun;Kim, Kyung-Hee;Han, Jung-Hoon;Whang, Wan-Kyunn
    • Natural Product Sciences
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    • v.11 no.2
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    • pp.75-78
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    • 2005
  • A new acetophenone named rumexin $(3-hydroxy-5-methyl-4-O-{\beta}-D-glucopyranosyl\;acetophenone)$ was isolated from methanolic extract of Rumex aquatica together with eight known compounds, $quercetin-3-O-{\beta}-D-glucuropyranoside$, $musizin-8-O-{\beta}-D-glucopyranoside$, $quercetin-3-O-{\alpha}-L-rhamnoside$, $emodin-8-O-{\beta}- D-glucopyranoside$, caffeic acid, $1-O-caffeoyl-{\beta}-D-glucopyranoside$, 1-methyl caffeic acid, $kaempferol-3-O-{\beta}-D-glucuropyranoside$. All of the above compounds were isolated from Rumex aquatica for the first time, and structures of compounds were established by spectroscopic means.

Phenolic Components from the Aerial Parts of Bromus japonicus Thunb. (참새귀리 지상부의 페놀성 성분)

  • Tao, Chao;Ahn, Dal-Rae;Xing, Ming Ming;Lee, Eun-Byeol;Kim, Dae-Keun
    • Korean Journal of Pharmacognosy
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    • v.43 no.3
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    • pp.213-216
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    • 2012
  • Six phenolic compounds were isolated from the aerial parts of Bromus japonicus (Gramineae) through repeated column chromatography. Their chemical structures were elucidated as luteolin (1), caffeic acid (2), luteolin-7-O-${\beta}$-D-glucopyranoside (3), quercetin-3-O-${\beta}$-D-galactopyranoside (4), quercetin-3-O-${\beta}$-D-glucopyranoside (5), and luteolin-4'-O-${\beta}$-D-glucopyranoside (6), respectively, by spectroscopic analysis. These compounds were isolated for the first time from this plant.

A New Steroidal Glycoside from Allium macrostemon Bunge

  • Kim, Yun Sik;Cha, Joon Min;Kim, Dong Hyun;Lee, Tae Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.24 no.1
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    • pp.54-58
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    • 2018
  • A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (2), phenylethyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (3), (Z)-3-hexenyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

Cytotoxic Anthraquinones and Stilbenes from Reynoutria sachalinensis (Fr. Schm.) Nakai

  • Jin, Wenyi;Na, Min-Kyun;Song, Gyu-Yong;Lee, Young-Mi;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.2
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    • pp.80-84
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    • 2005
  • Five known anthraquinones, physcion (1), I-O-methylemodin (2), emodin (3), $physcion-8-O-{\beta},-D-glucopyranoside$ (5), $emodin-8-O-{\beta},-D-glucopyranoside$ (6) and two known stilbenes, trans-resveratrol (4), $trans-resveratrol-3-O-{\beta},-D-glucopyranoside$ (7) were isolated from MeOH extract of Reynoutria sachalinensis (Polygonaceae). All structures were unambiguously established by 1D and 2D NMR and MS data and the compounds were evaluated for their cytotoxicity against L1210, HL-60, BI6F10 tumor cell lines in MTT assay. Among the compounds, trans-resveratrol (4) exhibited significant cytotoxic activity with $IC_{50}$ values of 9.2, 6.7 and $9.8\;{\mu}g/ml$, against the test cell lines respectively, but compounds 1-3 exhibited the moderate cytotoxic activity.

Chemical Constituents from the Fruits of Prunus mume

  • Jin, Qinghao;Lee, Chul;Lee, Jin-Woo;Lee, In-Sun;Lee, Mi-Kyeong;Jeon, Won-Kyung;Hwang, Bang-Yeon
    • Natural Product Sciences
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    • v.18 no.3
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    • pp.200-203
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    • 2012
  • The chromatographic separation of a methanol extract of Prunus mume (Rosaceae) led to the isolation of 5-hydroxymethyl-2-furaldehyde (1), 4-O-caffeoylquinic acid methyl ester (2), prunasin (3), 5-O-caffeoylquinic acid methyl ester (4), benzyl-O-${\beta}$-D-glucopyranoside (5), and liquiritigenin-7-O-${\beta}$-D-glucopyranoside (6). Their structures were determined by 1D, 2D-NMR and MS data analysis as well as by comparison of their data with the published values.

A Tannin Compound Isolated from the Underground Part of Rosa rugosa Thunb (해당화 지하부에서 분리한 탄닌 화합물)

  • Park, Jong-Cheol;Young, Han-Suk;Lee, Seung- Ho
    • Korean Journal of Pharmacognosy
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    • v.24 no.4
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    • pp.319-321
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    • 1993
  • A tannin compound has been isolated from the underground part of Rosa rugosa Thunb. and its structure has been established to be methyl gallate $3-O-{\beta}-D-(6'-O-galloyl)-glucopyranoside(1)$ on the basis of chemical and spectroscopic evidences. This compound was the first example in this plant.

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Efficient Isolation of Dihydrophaseic acid 3'-O-β-D-Glucopyranoside from Nelumbo nucifera Seeds Using High-performance Countercurrent Chromatography and Reverse-phased High-performance Liquid Chromatography

  • Rho, Taewoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.288-292
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    • 2018
  • High-performance countercurrent chromatography (HPCCC) coupled with reversed-phase highperformance liquid chromatography (RP-HPLC) method was developed to isolate dihydrophaseic acid 3'-O-${\beta}$-D-glucopyranoside (DHPAG) from the extract of Nelumbo nucifera seeds. Enriched DHPAG sample (2.3 g) was separated by HPCCC using ethyl acetate/n-butanol/water system (6:4:10, v/v/v, normal-phase mode, flow rate: 4.0 mL/min) to give 23.1 mg of DHPAG with purity of 88.7%. Further preparative RP-HPLC experiment gave pure DHPAG (16.3 mg, purity > 98%). The current study demonstrates that utilization of CCC method maximizes the isolation efficiency compared with that of solid-based conventional column chromatography.

Two new megastigmane glycosides from Phyllanthus ussuriensis

  • Ryu , Min-Youl;Kim, Chul-Young;Kim, Jin-Woong
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.191.2-191.1
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    • 2003
  • Phyllanthus ussuriensis Rupr. et Maxim. (Euphorbiaceae) has long been used in folk medicine to treat kidney and urinary bladder disturbances, intestinal infections, diabetes, and hepatitis. Reported chemical constituents of this species are one flavonoid (rutin), two gallotannins (gallic acid, methyl gallate) and two ellagitannins.An investigation of the n-BuOH fraction of P. ussuriensis led to the isolation of two new megastigmane glycosides, 10-hydroxy-4,7-megastigmadiene-3-one-9-O-b-D-glucopyranoside (1), 10- hydroxy-4,6-megastigmadiene-3-one-9-O-b-D-glucopyranoside (2) and two known compounds roseoside (3) and 3-oxo-a-ionol-9-O-b-D-glucopyranoside (4). (omitted)

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Alkyl Glycosides from the Flowers of Magnolia obovata (황목련 꽃으로부터 Alkyl Glycoside의 분리 동정)

  • Oh, Eun-Ji;Seo, Kyeong-Hwa;Kwon, Jung-Hwa;Lee, Dae-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.3
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    • pp.233-236
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    • 2015
  • The flowers of Magnolia obovata were extracted with aqueous MeOH and fractionated into EtOAc, n-BuOH, and $H_2O$ fractination. Three alkyl glycosides were isolated from the EtOAc fraction through repeated silica gel and ODS column chromatography. The structures were identified to be 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galacto-pyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), and 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3) on the basis of spectroscopic analyses such as fast atom bombardment mass spectrometry, infrared spectroscopy, 1D nuclear magnetic resonance (NMR) ($^1H$ and $^{13}C-NMR$), and 2D NMR (gCOSY, gHSQC, and gHMBC). These compounds were isolated for the first time from the flower of M. obovata in this study.