• Title/Summary/Keyword: ${\alpha}-D-glucopyranoside$

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Constituents of Spiraea prunifolia var. simpliciflora (조팝나무 뿌리의 성분 연구)

  • Lee, Eun-Hee;Chung, Soon-Ok;Kim, Chong-Won;Woo, Mi-Hee
    • Korean Journal of Pharmacognosy
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    • v.27 no.4
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    • pp.389-396
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    • 1996
  • Spiraea prunifolia var. simpliciflora (Rosaceae) is a deciduous. latifoliate shrub growing in most parts of Korea. The roots of this plant have been used for malaria, as antipyretics and emetics. From the roots of this plant, sterol glycoside and two triterpenoids were isolated and the structures were elucidated by chemical and spectroscopic methods. They were identified as $3{\beta}-hydroxyurs-12-ene-28-oic$ acid (ursolic acid.1), $2{\alpha}$, $3{\beta}$, $19{\alpha}-trihy-droxyurs-12-ene-28-oic$ acid (tormentic acid.2) and ${\beta}-sitoste-rol-3-O-{\beta}-D-glucopyranoside$ (3).

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The Flavonoids from Caragana Chamlagu Leaves (골담초엽의 플라보노이드)

  • 마충운;함인혜;황완균
    • YAKHAK HOEJI
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    • v.43 no.2
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    • pp.143-149
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    • 1999
  • The phytochemical studies of the leaves of Caragana chamlagu were carried out as a sieries of the investigation of medicinal resources. The roots of Caragana chamlagu have been used as neuralgia, arthritis and migraine in the folk medicines of Korea. The methanolic extract of the leaves of Caragana chamlagu was suspended with water and then separated with chloroform. Compound I was isolated from precipitates of these water fraction by recrystalization. The aqueous fraction of MeOH extract was performed to column chromatography on Amberlite XAD-4 and Sephadex LH-20, and three compounds, compound II, compound III, and compound IV were isolated. The structures of the four compounds were elucidated by spectroscopic data of $^1H-NMR$, ^{13}C-NMR$, IR, and FAB-MS. Compound I-IV were tilianine ($acacetin-7-O-{\beta}-D-glycopyranoside$), rutin($quercetin-3-O-{\alpha}-L-rhamnopyranosy(1{\rightarrow}6)-{\beta}-D-glu-copyranoside$), $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-D-galactopyranoside$, and apigetrin, ($apigenin-7-O-{\beta}-D-glycopyranoside$), respectively.

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Stereospecific Synthesis of Methyl-6-deoxy-$\beta$-L-idopyranoside (Methyl-6-deoxy-$\beta$-L-idopyranoside의 합성)

  • 민신홍;박복구;옥광대
    • YAKHAK HOEJI
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    • v.30 no.6
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    • pp.352-355
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    • 1986
  • Methyl-6-deoxy-$\beta$-L-idopyranoside was prepared in good yield by treatment of methyl 2,3,4-tri-O-benzyl-6-deoxy-$\alpha$-D-xylo-hex-5-enopyranoside with H$_2$ on pd, followed by reaction of Na/NH$_3$ at $-50^{\circ}C$. The ratio of L-idopyranoside and D-glucopyranoside was 7 to 1 in 80.7%. It was confirmed that L-idopyranoside was 1C conformation as being expected.

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A Further Furostanol Glycoside From Smilax china

  • Kim, Sung-Whan;Chung, Kyu-Charn;Son, Kun-Ho;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.20 no.3
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    • pp.145-146
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    • 1989
  • A furostanol glycoside, $mp\;190{\sim}198^{\circ}$, was isolated from the MeOH extract of Smilax china rhizomes. The structure was established as a mixture of $26-O-{\beta}-_D-glucopyranosyl-(25R)-22-methoxy-furost-5-en-3\beta,26-diol\;3-O-\alpha-_L-rhamnopyranosyl-(1\rightarrow2)-\beta-_D-glucopyranoside$ and its 22-hydroxy derivative on the basis of spectral data and chemical correlations.

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Phytochemical Studies on Rehmanniae Radix Preparata (숙지황(熟地黃)의 성분연구)

  • Lee, Joo-Young;Lee, Eun-Ju;Kim, Ju-Sun;Lee, Je-Hyun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.42 no.2
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    • pp.117-126
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    • 2011
  • Twenty-two compounds were isolated from the 70% ethanolic extract of Rehmanniae Radix Preparata (Scrophulariaceae) and their structures were identified as three triterpenoids [oleanolic acid (1), pomonic acid (2) and ursolic acid (5)], an iridoid, catalpol (13), four furan derivatives [5-hydroxymethyl-2-furaldehyde acetate (3), 5-hydroxymethyl-2-furfural (6), 5-hydroxymethyl-2-furancarboxylic acid (7), and 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15)], three phenethyl alcohol glycosides [darendoside B (14), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19)], four sugar derivatives [L-arabinose (11), raffinose (20), stachyose (21), and mannitol (22)], and seven others [2,5-dihydroxyacetophenone (4), succinic acid (8), daucosterol (9), ${\beta}$-sitosterol (10), adenosine (16), uridine (18) jio-cerebroside (12)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. This is the first report of the triterpenoids oleanolic acid (1), pomonic acid (2), and ursolic acid (5) from the genus Rehmannia, as well as the first report of compounds 5-hydroxymethyl-2-furaldehyde acetate (3), 2,5-dihydroxyacetophenone (4), daucosterol (9), darendoside B (14), 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15), adenosine (16), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19) from the Rehmanniae Radix Preparata.

A New Furofuran Lignan with Antioxidant and Antiseizure Activities from the Leaves of Petasites japonicus

  • Min Byung-Sun;Cui Hui Song;Lee Hyeong-Kyu;Sok Dai-Eun;Kim Mee Ree
    • Archives of Pharmacal Research
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    • v.28 no.9
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    • pp.1023-1026
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    • 2005
  • A new furofuran lignan (1) was isolated from the n-butanol fraction of the methanolic extract of the leaves of Petasites japonicus (Sieb. et Zucc.) Maxim. (Compositae). The structure of compound 1 was determined to be $2{\alpha}-(4'-hydroxy-3'-methoxyphenyl)-6{\alpha}-(4"-hydroxy-3"-methox­yphenyl)-8{\alpha}-hydroxy-3, 7-dioxabicyclo[3.3.0]octane\;4'-O-({\beta}-D-glucopyranoside)$ by spectroscopic methods including 2D-NMR. In further studies, it was found that the compound 1 expressed an antioxidant activity in DPPH radical scavenging assay, and moreover, ameliorated the seizure in kainic acid-treated mice.

Enzymatic Glycosylation of Fatty Acids by Methyl Glycosides (메틸글리코시드에 의한 지방산의 효소적 배당화)

  • SunWoo, Hwan;Kim, Chong-Tai;Kim, Hae-Sung
    • Journal of the Korean Applied Science and Technology
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    • v.16 no.1
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    • pp.83-94
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    • 1999
  • Glycoside fatty acid esters were synthesized by lipase-catalyzed glycosylation of fatty acids with methyl glycoside in solvent and solvent free process. Optimum condition of solvent process using 2-methyl-2-propanol were : moral ratio of methyl glycoside to fatty acid 1:3: initial concentration of methyl glycoside 50g/l:enzyme(immodilized lipase Novozym 435 from Candidia antarctica) content 1%(w/v) : desiccant content 9%(w/v); reaction temperature $60^{\circ}C$: reaction time 10hrs. The yield of 99% was obtained. Solvent-free process was carried out in total absence of solvent at $70^{\circ}C$ under reduced pressure, 5-20mmHg. To give meximum yield of 99% at the optimum condition of molar ratio of methyl glycoside to fatty acid 1:3, enzyme content 10%(w/w), and reaction time 10hrs. The glycosylation reactivity of different glycosylation agents were sequent to $Methyl-{\beta}-D-fructofuranoside$. $Methyl-{\beta}-D-glucopyranoside$. $Methyl-{\beta}-D-fructofuranosi$ de, and $Methyl-{\alpha}-D-glucopyranoside$.

Isolation and Characterization of Antioxidative Compounds from the Aerial Parts of Angelica keiskei

  • Kim, So-Joong;Cho, Jeong-Yong;Wee, Ji-Hyang;Jang, Mi-Young;Kim, Cheol;Rim, Yo-Sup;Shin, Soo-Cheol;Ma, Seung-Jin;Moon, Jae-Hak;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.14 no.1
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    • pp.58-63
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    • 2005
  • Ethyl acetate-soluble neutral fraction of hot water extracts from the aerial parts of Angelica keiskei showed a 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Six antioxidative compounds were purified and isolated by various chromatographic procedures. Based on the analyses of FAB-MS and NMR, the isolated compounds were structurally elucidated as luteolin 7-O-${\beta}$-D-glucopyranoside (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2), quercetin 3-O-${\beta}$-D-glucopyranoside (3), quercetin 3-O-${\alpha}$-D-arabinopyranoside (4), kaempferol 3-O-${\alpha}$-D-arabinopyranoside (5), and luteolin 7-O-rutinoside (6). The glycosides of flavonols and luteolin showed DPPH radical-scavenging activity. One molecule of 2, 3, 4, 6, 1, and 5 scavenged 4.2, 4.2, 4.1, 2.5, 2.2, and 1.4 molecules of DPPH radical, respectively.

Inhibitory Effect of Aqueous Extracts from the Fruit Body of Lentinus edodes on Rat Intestinal Mucosa $\alpha$-glucosidase Activity and Reducing the Increase of Blood Glucose after Streptozotocin-induced Diabetic Rats

  • Lee, In-Soon;Chae, Heui-Jun;Moon, Hae-Yeon
    • Biomedical Science Letters
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    • v.14 no.1
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    • pp.63-68
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    • 2008
  • The aqueous extract from the fruit body of Lentinus edodes was evaluated for inhibitory activities against $\alpha$-glucosidase isolated from Spargue-Dawley male rats. A aqueous extract of Lentinus edodes exhibited 13.8% inhibitory activity on using 2 mM p-nitrophenyl $\alpha$-D-glucopyranoside as a substrate ($IC_{50}$ 75.3 mg/ml). The aqueous extract of Lentinus edodes inhibition type on $\alpha$-glucosidase was determined to be competitive inhibition. When it was oral administered to increase of blood glucose levels after STZ-induced in a dose dependent dietary. These results suggest that aqueous extract of Lentinus edodes effect a metabolism of intestine, and thereby reducing the increase of blood glucose after STZ-induced.

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Improvement of Transglycosylation Efficiency using a Glycosynthase Mutant derived from Thermoplasma acidophilum ${\alpha}$-Glucosidase (Thermoplasma acidophilum 유래 ${\alpha}$-glucosidase로 부터 생산된 glycosynthase 돌연변이 단백질의 개선된 당전이 효율)

  • Hwang, Sung-Min;Seo, Seong-Hwa;Park, In-Myoung;Choi, Kyoung-Hwa;Kim, Do-Man;Cha, Jae-Ho
    • Microbiology and Biotechnology Letters
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    • v.40 no.2
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    • pp.104-110
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    • 2012
  • Glycosynthase is an active site nucleophile mutant enzyme, prepared from glycosidase, which is capable of synthesizing oligosaccharide derivatives without the hydrolysis of the product. Thermoacidophilic ${\alpha}$-glucosidase of Thermoplasma acidophilum (AglA) exhibits a transglycosylating activity yielding various glycosides. AglA was converted to glycosynthase by the substitution of the catalytic nucleophile Asp-408 residue into non-nucleophile glycine in order to increase its ability to synthesize various glycosides by transglycosylation. The glycosynthase mutant was purified by Ni-NTA chromatography and its glycoside-synthesizing activity was measured by using an external nucleophile, sodium formate buffer, providing maltose as a donor and p-nitrophenyl-${\alpha}$-D-glucopyranoside ($pNP{\alpha}G$) as an acceptor, respectively. In addition, $pNP{\alpha}G$ was examined for its feasibility to act as both a donor and an acceptor, and products were compared with those of the wildtype enzyme. The mutant enzyme was found to catalyze the formation of a specific product from $pNP{\alpha}G$ with a yield of 42.5% without further hydrolysis, while the wild-type enzyme produced two $pNP{\alpha}G$ products at low yields. The results demonstrate the possibility of satisfactory yields for the reactions in the presence of small amounts of acceptor, and demonstrate that the high activity of the mutant, at pHs below neutrality, was applicable in the transfer of glucose from the natural donor.