• Title/Summary/Keyword: glucopyranosyl

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Cerebrosides from Longan Arillus

  • Ryu, Ji-Young;Kim, Ju-Sun;Kang, Sam-Sik
    • Archives of Pharmacal Research
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    • v.26 no.2
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    • pp.138-142
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    • 2003
  • From the pulp of Euphoria longana (Longan Arillus), three cerebroside molecular species have been isolated. Six known cerebrosides, soyacerebrosides I and II, 1-Ο-$\beta$-D-glucopyranosyl-(2S,3R,4E,8E)-2-(2 -lignoceroylamino)-4,8-octadecadiene-1,3-diol (long an cerebroside I) and its 8Z isomer (Iongan cerebroside II), momor-cerebroside I, and phytolacca cerebroside, were identified as major components of these cerebroside molecular species. All the cerebrosides were shown to be a mixture of geometrical isomers (8E and 8Z) of sphingosine-type or phytosphingosine-type glucocerebrosides possessing 2-hydroxy fatty acids. The structures of these cerebrosides have been determined on the basis of chemical and spectroscopic evidence.

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.

Identification of New Compounds from Catharanthus roseus Hairy Root Cultures

  • Chung, Ill-Min;Ali, Mohd;Yang, Young-Mok;Peebles, Christie A. M.;Chun, Se-Chul;Lee, Sun-Joo;San, Ka-Yiu;Ahmad, Ateeque
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1294-1298
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    • 2007
  • Two new compounds lanast-5,8-dien-3β-ol-27-oic acid-3β-D-glucopyranosyl (4'-1'')-10'',11''-dimethoxy anthracene (1), 2-methoxy-6-(n-nonacontan-5'',6''-dionyl)-11-hydroxy-13-methyl-11β-D-rhamnopyranoside anthracene (2) have been isolated from the hairy root cultures of Catharanthus roseus. Their structures have been elucidated with the help of 500 MHz NMR using one- and two-dimensional NMR in combination with IR, EI/MS, FAB/MS and HRFABMS spectroscopy.

Antioxidant Compounds from the Root Bark of Hibiscus syriacus

  • Lee, Sang-Jun;Yun, Young-Sook;Lee, In-Kyoung;Ryoo, In-Ja;Yun, Bong-Sik;Yoo, Ick-Dong
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 1999.10a
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    • pp.110-117
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    • 1999
  • A new lignan named as hibiscuside, (+) pinoresinol 4-O-[-glucopyranosyl (12) -rhamnoside] (1), and a known lignan, syringaresinol (2) were isolated from the root bark of Hibiscus syriacus together with two feruloyltyramines (3,4) and three known isoflavonoids (5,6,7). The structures of these compounds have been established on the basis of their NMR, Mass, UV spectra. Among these phenolic compounds,6-O-acetyl daidzin (5), 6-O- acetyl genistin (6), and 3-hydroxy daidzein (7) with IC50 values of 8.2, 10.6, and 4.1 M, respectively, significantly inhibited lipid peroxidation in rat liver microsomes Hibiscuside (1), E and Z-N-feruloyl tyramines (3,4) exhibited moderate antioxidant activity.

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A Modified Alkaline Hydrolysis of Total Ginsenosides Yielding Genuine Aglycones nad Prosapogenols

  • Im, kwang-Sik;Chang, Eun-Ha;Je, Nam-Gyung
    • Archives of Pharmacal Research
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    • v.18 no.6
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    • pp.454-457
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    • 1995
  • To improve the yield of genuine aglycones from glycosides, the conditions of alkaline hydrolysis were investigated, and a modified method was established. The modified method empolyed pyridine as an aprotic solvent. To complete the hydrolysis and obtain 20(S)-protopanaxadiol (1) and 20(S)-protopanaxatriol(2), which are the genuine aglycones of ginsenosides, total ginsenosides were refluxed with sodium methoxide in pyridine. Addition of methanol, a protic polar solvent to the reaction miuxture, led partial hydrolysis yielding a mixture of the genuine prosapogenols. Of the prosapogenols compound 3 and 6 characteristically possessed D-glucopyranosyl moiety attached at the sterically hindered C-20 hydroxyl group. 3 and 6 were not obtaijned by other hydrolysisw methods except by the soil bacterial hydrolysis.

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A Novel Cycloartane Glycoside from Thalictrum uchiyamai

  • Choi, Young-Hee;Kim, Nan-Gyeong;Lee, Ihn-Ran
    • Archives of Pharmacal Research
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    • v.19 no.5
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    • pp.429-431
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    • 1996
  • A new cycloartane glycoside (1) was isolated from the aerial part of Thalictrum uchiyamai Nakai (Ranunculaceae). On the basis of chemical and physicochemical evidence, the aglycone structure of this compound was characterized as 116, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid, a new derivative of cycloartane triterpene. Also the oli-gosaccharide moiety of this glycoside were determined as 29-O-${alpha}$-L-rhanmnopyranosyl- ($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranose by application of HMBC technoque. Consequently, the structure of compound 1 was elucidated as 29-O-${alpha}$-L-rhanmnopyranosy-($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranosyl-16, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid ester.

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A New Indolinepeptide from Paecilomyces sp. J300

  • Kwon, Hak-Cheol;Kim, Kyung-Ran;Zee, Sang-Deuk;Cho, Sae-Yun;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.604-609
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    • 2004
  • A new indolinepeptide (3) was isolated, together with two known compounds, a cerebroside (1) and an alloxazine (2), from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic data, their structures were elucidated as (4E, 8E, 25, 2'R, 3R )-N-2'-hydroxy-hexadecanoyl-1-O-$\beta$-D-glucopyranosyl-9-methyl-4, 8-sphingadienine (1), 7,8-dimethylalloxazine (2) and 3$\beta$,5-dihydroxy-1-N-methyl-indoline-2$\beta$-carbonyl amino-D-alanyl-erythro-$\beta$-hydoxyiso-leucinyl-glycine (3).

Two New Phenolic Glycosides from Curculigo orchioides

  • Zuo, Ai-Xue;Shen, Yong;Jiang, Zhi-Yong;Zhang, Xue-Mei;Zhou, Jun;Lu, Jun;Chen, Ji-Jun
    • Bulletin of the Korean Chemical Society
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    • v.32 no.3
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    • pp.1027-1029
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    • 2011
  • Two new phenolic glycosides were isolated from the rhizomes of Curculigo orchioides Gaertn.. Based on comprehensive spectroscopic analyses including IR, MS, 1D- and 2D NMR (COSY, HSQC, and HMBC), their structures were elucidated as 3-hydroxyl-5-methyphenol-1-O-[${\beta}$-D-glucopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucopyranoside (1) and 1',3'-dimethoxyl-4-hydroxyalangifolioside (2).

Ester Derivatives from Tannase-treated Prunioside A and Their Anti-inflammatory Activities

  • Jun, Chang-Soo;Yoo, Myung-Ja;Lee, Woo-Yiel;Kwak, Kyung-Chell;Bae, Moon-Sung;Hwang, Woo-Taek;Son, Dong-Hwan;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • v.28 no.1
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    • pp.73-76
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    • 2007
  • Prunioside A, isolated from the methanol extract of Spiraea prunifolia var. Simpliciflora's root, is composed of coumaroyl, monoterpene-type, and glucosyl units. The esterase activity of tannase was used to remove the p-coumaroyl and glucopyranosyl groups. The enzymatically hydrolyzed compound was reacted with various acyl chlorides to synthesize its ester derivatives, which showed the inhibitory effects on NO production in murine machrophage?like RAW 264.7 cells stimulated with lipopolysaccharide and interferon-γ.

Ginsenoside $Rs_3$, A genuine Dammarane-Glycoside from Korean Red Ginseng

  • Baek, Nam-In;Kim, Jong-Moon;Park, Jeong-Hill;Ryu, Jae-Ha;Kim, Dong-Seon;Lee, You-Hui;Park, Jong-Dae;Kim, Shin-Il
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.280-282
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    • 1997
  • A genuine dammarane-glycoside, named as ginsenoside $ Rs_3$, was isolated from the MeOH extracts of Korean red ginseng (Panax ginseng C.A. Meyer) through repeated silica gel column chromatographies and its chemical structure was determined as (20S)-protopanaxadiol $3-O-[6^{11}-O-acetyl-{\beta}-D-glucopyranosyl (1{\rightarrow2)-{\beta}-D-$glucopyranoside on the basis of several spectral and physical evidences including HMBC and FAB-MS.

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