• Food Science and Biotechnology
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• v.18 no.1
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• pp.271-274
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• 2009

Cereal $\beta$-glucans, linked essentially by mixed $\beta$-(1,4/1,3) glycosidic bonds, were extracted, purified, and structurally identified. Previously chemical structure of barley $\beta$-glucans was characterized from 3 varieties of 'Gang', 'Ohl', and 'Gwangan', and the (1,4)/(1,3) linkage ratio of the $\beta$-glucans was identical. In this study, $\beta$-glucans from 1 barley ('Chal') and 3 oat ('Ohl', 'Samhan', and 'Donghan') varieties were structurally scrutinized, and the linkage pattern of total 7 cereal $\beta$-glucans was compared. The amount of 2 major 3-O-$\beta$-cellobiosyl-D-glucose (DP3) and 3-O-$\beta$-cellotriosyl-D-glucose (DP4) from barley and oat accounted for only 66.6-73.3 and 68.12-81.89% of water-extractable $\beta$-glucan fractions, and the (1,4)/(1,3) linkage ratios of both barley and oat $\beta$-glucans were within very narrow range of 2.27-2.31 and 2.38-2.39, respectively, among the cultivars tested. Structural difference in the cereal $\beta$-glucans was evident when DP3:DP4 ratio in the $\beta$-glucan structure was compared. As a result, this ratio was significantly greater for barley $\beta$-glucan (2.26-2.74) than for oat (1.54-1.66). Chal-B had the greatest DP3 to DP4 ratio among the samples, which in turn reflected the least amount of (1,4)-linkages.

• Journal of the Korean Chemical Society
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• v.42 no.1
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• pp.78-83
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• 1998

It's necessary to develope a facile methodology forming ${\alpha}$-altropyranosidic linkage, for the synthesis of trisaccharide repeating unit of O-antigenic part of Campylobacter jejuni gram negative bacteria. In this paper, the effective synthesis of disaccharides containing ${\alpha}$-altropyranosidic linkage by 1,2-trans glycosidation of allal derivatives was discussed. 4, 6-O-Benzylidene-3-O-(t-butyldimethylsilyl)-D-allal was treated with DMDO (3,3-dimethy ldioxirane) to yield 1,2-anhydro-4, 6-O-benzylidene-3-O-(t-butyldimethylsilyl)-${\beta}$-D-altropyranose. The reaction of 1,2-anhydro-4, 6-O-benzylidene-3-O-(t-butyldimethylsilyl)-${\beta}$-D-altropyranose with allyl alcohol gave allyl 4, 6-O-benzylidene-3-(t-butyldimethylsilyl)-${\alpha}$-D-altropyranoside quantitatively, and reactions with glucals were also successful to prepare ${\alpha}$-altropyranosodic disaccharides. It is convinced that 1,2-trans glycosidation of allal derivatives should be an attractive choice for preparing oligosaccharides containing ${\alpha}$-altropyranosidic linkages.

• Journal of Forest and Environmental Science
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• v.12 no.1
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• pp.37-44
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• 1996

Two dilignols composed of ${\beta}$-O-4 structure, a important substructure compound in lignin, was synthesized in high yield in a series of the synthetic studies of lignin model compounds. The dimers were identified with $^1H$ and $^{13}C$-NMR and Mass spectroscopy. The important compound of among them, the final synthetic compound [IV].is called 1-(3,4-dimethoxyphenyl)-2-(2'-methoxy-4'-hydroxymethylphenoxy)-propanediol-l,3. This dimeric lignin model compounds should be usefull for the studies of lignin reactions such as pulping, bleaching, pyrolysis, hydrogenolysis, oxidation, reduction, biodegradation, and chemical utilization.

• Journal of the Korean Wood Science and Technology
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• v.38 no.3
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• pp.223-229
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• 2010

In this study diverse dehydrogenative polymers (DHPs) were synthesized with three precursors of native lignin [p-coumaryl alcohol (PCA), coniferyl alcohol (CA), sinapyl alcohol (SA)] in the presence of horseradish peroxidase (HRP, EC. 1.11.1.7)/$H_2O_2$. To compare the structural features between DHPs and native lignin, the DHPs as well as pine/poplar milled wood lignins were simultaneously subjected to gel permeation chromatography (GPC) to determine average molecular weights and derivatization followed by reductive cleavage (DFRC) to investigate the frequency of ${\beta}$-O-4 linkage. The highest yield of DHP was measured to 71% when CA was solely injected (G-DHP) and the yield of H-DHP was 42%. However, single injection of SA could not form any polymer in this system. The average molecular weights of DHPs were ranged between 3,000~4,700, which were only 1/2 fold compared with that of pine MWL (G-type lignin: Mw 7,340) and 1/3 scale compared with that of poplar MWL (GS-type lignin: Mw 13,250). DFRC analysis revealed that the formation of ${\beta}$-O-4 linkage during dehydrogenative polymerization was the highest in the GS-DHP with ca. 502 ${\mu}mol$/g, which was, however, remained to only 50% compared to that in poplar MWL (1107 ${\mu}mol$/g). The ${\beta}$-O-4 linkage was estimated to ca. 286 ${\mu}mol$/g In the G-DHP, which was twice as much as that of H-DHP(127 ${\mu}mol$/g). Similar to GS-DHP, only half amount of ${\beta}$-O-4 linkage, compared to pine MWL, was formed during in vitro polymerization of CA by horseradish peroxidase/$H_2O_2$.

• Applied Biological Chemistry
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• v.17 no.2
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• pp.125-137
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• 1974

The chemical structure of glycolipid of Selenomonas ruminantium cell wall was to be elucidated. The bacterial cells were treated in hot TCA and the glycolipid fractions were extracted by the solvent $CHCl_3\;:\;CH_3OH$ (1 : 3). The extracted glycolipids fraction was further separated by acetone extraction. The acetone soluble fraction was named as the spot A-compound. The acetone insoluble but ether soluble fraction was named as the spot B-compound. These two compounds were examined for elucidation of their chemical structure. The results were as follows: 1. The IR spectral analysis showed that O-acyl and N-acyl fatty acids were linked to glucosamine moiety in the spot A-compound. However in the spot B-compound in addition to O and N-acyl acids phosphorus was shown to be attached to glucosamine. 2. It was recognized by gas liquid chromatography that spot A compound contained beta-OH $C_{13:0}$ fatty acid in predominance in addition to the fatty acid with beta-OH $C_{9:0}$, whereas the spot B compound was composed of the predominant fatty acid of beta-OH $C_{13:0}$ with small amount of beta-OH $C_{9:0}$. 3. According to the paper chromatographic analysis of hydrazinolysis products of the spot A compound, a compound of a similar Rf value as the chitobiose was recognized, which indicated a structure of two molecules glucosamine condensed. The low Rf value of the hydrazinolysis product of the spot B-compound confirmed the presence of phosphorus attached to glucosamine. 4. The appearance of arabinose resulting from. ninhydrin decomposition of the acid hydrolyzate of the spot A compound indicated that the amino group is attached to $C_2$ of glucosamine. 5. The amount of glucosamine in the N-acetylated spot A compound decreased in half of the original content by the treatment. with $NaBH_4$, indicating that there are two molecules of glucosamines in the spot A compound. The presence of 1, 6-linkage between two molecules of glucosamine was suggested by the Morgan-Elson reaction and confirmed by the periodate decomposition test. 6. By the action of ${\beta}-N-acetyl$ glucosaminidase the N-acetylated spot A compound was completely decomposed into N-acetyl glucosamine, whereas the spot B compound was not. This indicated the spot A compound has a beta-linkage. 7. When phosphodiesterase or phosphomonoesterase acted on $^{32}P-labeled$ spot B compound, $^{32}P$ was not released by phosphodiesterase, but completely released by phosphomonoesterase. This indicated that one phosphorus is linked to glucosamine moiety. 8. The spot A compound is assumed to have the following chemical structure: That is glucosaminyl, ${\beta}-1$, 6-glucosamine to which O-acyl and N-acyl fatty acids are linked, of which the predominant fatty acid is beta-OH $C_{13:0}$ fatty acid in addition to beta-OH $C_{9:0}$ fatty acid 9. The spot B compound is likely to have the linkage of $glucosaminyl-{\beta}-1$, 6-glucosamine to which phosphorus is linked in monoester linkage. Furthermore both O-acyl and N-acyl fatty acids contained beta-OH $C_{13:0}$ fatty acid predominantly in addition to beta-OH $C_{9:0}$ fatty acid.

• Archives of Pharmacal Research
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• v.25 no.3
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• pp.270-274
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• 2002

Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

• Journal of Korea Foresty Energy
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• v.20 no.1
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• pp.35-41
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• 2001

Lignin model compounds I-lV were pyrolyzed at 315$^{\circ}C$. The mixture compounds pyrolized were analyzed by GC-MS spectrometry. The results were summarized as follows : 1. From the pyrolysis of lignin model compound I and II, 0.45mo1 of guaiacol, 0.5mol of dimethoxyphenol(DMP), and 0.12 and 0.23mo1 of dimethoxyacetonphenone(DMAP) were produced respectively. 2. In the pyrolysis of lignin model compound III and IV, 0.26mol of guaiacol, 0.30mo1 of DMP, and 0.09 and 0.15mo1 of trimethoxyaretonphenone(TMAP) were produced respectively 3. Pyrolysis mechanism of lignin model compounds are dehydrated at first, and $\beta$-04 linkage cleavaged, and then guaiacol, DMP, DMAP and TMAP were produced. The above results show that lignin model compound I and II produce more aromatic compounds than lignin model compound III and IV. This is reason that veratryl unit structures may pyrolize easier than trimethoxyphenol unit structures. The closer research is proceeding.

• Journal of the Korean Wood Science and Technology
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• v.17 no.3
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• pp.28-44
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• 1989

This experiment was carried out to contribute to the synthetic methods of ligin model compounds. The ligin model compounds of arylglycerol-${\beta}$-arylether structure were synthesized in high yield through three or four reaction steps. The starting compound was commercial 3, 4, 5-trimethoxyace tophenone and the final compounds were 1-(2-methoxyphenoxy)-2 - (3, 4, 5 - trimethoxyphenyl)-ethanol(IV), 1-(3, 4, 5-trimethoxyphenyl)-2-(2-methoxy-phenoxy)-propandiol-1,3 (VI), 1-(2, 6-dimethoxyphenoxy)-2-(3, 4, 5-trimethoxyphenyl)-ethanol (VIII), and 1-(3, 4, 5-trimethoxyphenyl)-2-(2, 6-dimethoxyphenoxy)-propandiol-1, 3 (X). The structures of synthetic compounds were identified by IR, $^1H$-NMR spectroscopy and Mass spectrometry.

• Journal of the Korean Wood Science and Technology
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• v.37 no.4
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• pp.372-380
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• 2009

After supercritical water treatment of poplar wood meals (passed through 60 mesh) for 60s between 325 and $425^{\circ}C$ at the fixed pressure at $220{\pm}10atm$, some solid residues were present in the degradation products. They mainly consisted of chemically modified lignin and fibrous materials. Glucose and xylose were identified as main sugar components of fibrous materials, and the highest ratio of glucose/xylose was achieved at the highest reaction temperature. As reaction temperature was elevated, the portion of fibrous materials decreased in the solid residues, while lignin was further accumulated. The H : G : S ratio of lignin in solid residues was estimated by analytical pyrolysis. Irrespective of reaction temperatures, the H:G:S ratios were not significantly changed in the lignin in solid residues. Compared to poplar milled wood lignin (MWL), it was remarkable that H type monomers were further lowered, while portion of S type monomers increased. The amount of G type monomers were relative stable. In presence of HCl catalyst, lowering H type as well as enhancing S type was further distinguishable. According to the result of nitrobenzene oxidation (NBO), ca. 265 mg of vanillin and syringaldehyde was yielded from poplar MWL as main products. However, remarkably reduced amount of NBO products were determined from solid residues by raising operating temperature as well as by the addition of HCl catalyst. These results strongly indicate that $\beta$-O-4 linkage could be easily cleaved during supercritical water treatment, so that the lignins in the solid residues seem to be condensed phenol polymers, which are mainly formed by carbon-carbon linkages rather than $\beta$-O-4 linkage.

• Journal of the Korean Wood Science and Technology
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• v.43 no.3
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• pp.344-354
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• 2015

To investigate the effects of ionic liquid pretreatment on biomass, giant miscanthus was treated with 1-ethyl-3-methylimidazolium acetate ([Emim][OAc]) and 1-butyl-3-methylimidazolium acetate ([Bmim][OAc]) at three temperature conditions ($90^{\circ}C$, $110^{\circ}C$, and $130^{\circ}C$). As temperature condition increased, yield of the cellulose-rich product (CP) was reduced from 87.2% to 67.6%, while yield of the ionic liquid lignin (ILL) increased from 2.2% to 9.9%. Compared to the ILL, CP had lower carbon contents and higher oxygen contents. Enzymatic hydrolysis of CPs showed that conversion ratio of CP treated with [Emim][OAc] at $110^{\circ}C$ was 56.7%, the highest digestibility. Thermogravimetric analysis indicated that the maximum degradation rate decreased as temperature condition increased. In addition, maximum degradation temperature of ILL treated with [Emim][OAc] ranged from 274 to $279^{\circ}C$ which was lower than that of ILL treated with [Bmim][OAc]. Analytical date for ${\beta}$-O-4 linkage frequency in the ILL revealed that ${\beta}$-O-4 linkage frequency in the ILL decreased as the temperature rose. Furthermore, the highest S/G ratio of the ILL was determined to ca. 1.2 obtained from [Bmim][OAc] treatment at $110^{\circ}C$.