- Structure of cycloquivinoside a from the aerial part of Astragalus chivensis
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The new cycloartane glycoside cycloquivinoside A, 24S-25-methoxycycloartan- 3β,6α,16β,24,25-pentaol 3-O-β-D-glucopyranoside, was isolated from the aerial part of Astragalus chivensis Bunge (Leguminosae). The structure was established based on chemical transformations and 2D spectra (TOCSY, ROESY, HMBC, HSQC, COSY).
- Naubeev,Uteniyazov,Isaev,Kachala,Shashkov
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- A new picrotoxane sesquiterpene from the berries of Baccaurea ramiflora with antifungal activity against Colletotrichum gloeosporioides
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(Image Presented) Three picrotoxane sesquiterpenes including one new glycoside and two known constituents, sapidolide A (2) and picrotoximaesin (3), were isolated from the berries of Baccaurea ramiflora. The structure of the new sesquiterpene glycoside, ramifloside (1), was elucidated as 2-one-6α-hydroxy-13-nor-11-picrotoxen-3(15β)-olide 10-O-β-d-glucopyranoside on the basis of extensive spectroscopic analysis. Compounds 1-3 exhibited antifungal activity against Colletotrichum gloeosporioides with MICs of 12.5, 12.5 and 50 g/mL.
- Pan, Zheng-Hong,Ning, De-Sheng,Huang, Si-Si,Wu, Yun-Fei,Ding, Tao,Luo, Lei
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- Steroidal saponins from Smilax excelsa rhizomes
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From the n-butanol soluble fraction of the methanol extract of the rhizomes of Smilax excelsa, three new furostanol saponins 3-O-[4-O-acetyl-α-L- rhamnopyranosyl-(1 → 2)-{α-L-rhamnopyranosyl-(1 → 4)}-β-D-glucopyranosyl]-26-O-[β-D-glucopyranosyl]-22α-hydro
- Ivanova, Antoaneta,Mikhova, Bozhanka,Klaiber, Iris,Dinchev, Dragomir,Kostova, Ivanka
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- Two new oleanane-type triterpenoids from platycodi radix and anti-proliferative activity in HSC-T6 Cells
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Two new oleanane-type triterpenoids, named platycodonoids A and B (1, 2), together with five known saponins, including platycodin D (3), deapioplatycodin D (4), 3-O-β-D-glucopyranosyl polygalacic acid (5), 3-O-β-D- glucopyranosyl platycodigenin (6) and polygalacin D (7), were isolated from the roots of Platycodon grandiflorum. On the basis of spectral data and chemical evidence, the structures of the new compounds were elucidated as 2β,3β,23,24-tetrahydroxy-28-nor-olean-12-en-16-one (1) and 2β,3β,23,24- tetrahydroxy-28-nor-olean-12-en-16-one-3-O-β-D- glucopyranoside (2). Compounds 1-7 were evaluated for their in vitro anti-proliferative activity against the HSC-T6 cell line.
- Zhan, Qin,Zhang, Feng,Sun, Lianna,Wu, Zhijun,Chen, Wansheng
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- Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling
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The phenolic content of the ethanol extract of the stem bark of the Brazilian plant Schinopsis brasiliensis Engl. (Anacardiaceae) has been evaluated together with the antioxidant activity. The good antioxidant activity exhibited in the Trolox Equivalent A
- Santos, Clisiane Carla de Souza,Masullo, Milena,Cerulli, Antonietta,Mari, Angela,Estevam, Charles Dos Santos,Pizza, Cosimo,Piacente, Sonia
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- Steroidal saponins from the leaves of Yucca de-smetiana and their in vitro antitumor activity: Structure activity relationships through a molecular modeling approach
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Four steroidal saponins were isolated from the leaves of Yucca de-smetiana Baker. Their structures were established using one- and two- dimensional NMR spectroscopy and mass spectrometry. The structure of the new steroidal saponin was identified as: (25R)-3β-hydroxy-5α-spirostan-3-O-β-d- xylopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (desmettianoside C) along with three known spirostanol and furostanol saponins. The isolated saponins were evaluated for their antitumor activity against HCT116, MCF7, HepG2, and A549 cell lines. Saponins 3 and 4 showed potent activity against HCT116, MCF7, and HepG2 cell lines in comparison with the positive control doxorubicin. A molecular modeling approach was performed to establish conformational criteria that could affect the biological activity of the isolated saponins.
- Eskander, Jacqueline,Sakka, Ola K.,Harakat, Dominique,Lavaud, Catherine
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- Molecular basis of the 14-3-3 protein-dependent activation of yeast neutral trehalase Nth1
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The 14-3-3 proteins, a family of highly conserved scaffolding proteins ubiquitously expressed in all eukaryotic cells, interact with and regulate the function of several hundreds of partner proteins. Yeast neutral trehalases (Nth), enzymes responsible for the hydrolysis of trehalose to glucose, compared with trehalases from other organisms, possess distinct structure and regulation involving phosphorylation at multiple sites followed by binding to the 14-3-3 protein. Here we report the crystal structures of yeast Nth1 and its complex with Bmh1 (yeast 14-3-3 isoform), which, together with mutational and fluorescence studies, indicate that the binding of Nth1 by 14-3-3 triggers Nth1’s activity by enabling the proper 3D configuration of Nth1’s catalytic and calcium-binding domains relative to each other, thus stabilizing the flexible part of the active site required for catalysis. The presented structure of the Bmh1:Nth1 complex highlights the ability of 14-3-3 to modulate the structure of a multidomain binding partner and to function as an allosteric effector. Furthermore, comparison of the Bmh1:Nth1 complex structure with those of 14-3-3:serotonin N-acetyltransferase and 14-3-3:heat shock protein beta-6 complexes revealed similarities in the 3D structures of bound partner proteins, suggesting the highly conserved nature of 14-3-3 affects the structures of many client proteins.
- Alblova, Miroslava,Smidova, Aneta,Docekal, Vojtech,Vesely, Jan,Herman, Petr,Obsilova, Veronika,Obsil, Tomas
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- Studies on absorption and hydrolysis of ethyl α-D-glucoside in rat intestine
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Ethyl α-D-glucoside (α-EG) is normally contained in Sake, which has been taken by Japanese people since ancient times. In this study, the intestinal absorption of α-EG was investigated using rat everted intestinal sac. Furthermore, the α-EG hydrolytic activity in rat intestine was compared with disaccharides hydrolytic activities, and the effects of α-EG on disaccharides hydrolysis were examined using crude enzyme preparation from rat intestinal acetone powder. Glucose liberated from α-EG was detected in a serosal solution of everted rat intestinal sac, but it was only less than 4% of absorbed intact α-EG. α-EG absorption into small intestinal tissue was reduced by elimination of sodium ion from the mucosal solution or under the presence of phlorizin. The hydrolytic activity for α-EG was detected in crude enzyme preparation from rat intestinal acetone powder, but it showed a low value as compared to those for disaccharides. α-EG showed mixed type inhibition for maltose and sucrose hydrolysis, but inhibitory concentrations of α-EG required for 50% inhibition for the maltose and sucrose hydrolysis were higher than those of arabinose and acarbose. In conclusion, a small amount of α-EG was hydrolyzed and most of it was absorbed via SGLT1 as an intact form in the rat small intestine, and the inhibitory effect of α-EG on disaccharides hydrolysis was weak.
- Mishima, Tomoyuki,Tanaka, Keiko,Tsuge, Haruhito,Sugita, Jun,Nakahara, Michio,Hayakawa, Takashi
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- Composition of the fresh leaves and stems of Melissa officinalis and evaluation of skin irritation in a reconstituted human epidermis model
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The composition of a centrifuged product obtained from the fresh leaves and stems of Melissa officinalis and skin irritation in the reconstituted human epidermis (Episkin model) have been investigated in comparison to the EtOH-H2O (1:1) extract
- Mencherini, Teresa,Picerno, Patrizia,Russo, Paola,Meloni, Marisa,Aquino, Rita
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- A new flavonoid glycoside from mistletoe transformed by Rhodobacter sphaeroides
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A new flavonoid glycoside, rhamnazin-3-O-β-D-apiosyl-(1→2)- β-D-[6″-(3-hydroxy-3-methylglutaric methyl ester)]-glucoside (1), was isolated together with seven known flavonoid compounds from mistletoe transformed by Rhodobacter sphaeroides (PSBT). Its structure was elucidated on the basis of MS, 1D, and 2D NMR techniques. All of the eight compounds were subjected to antioxidant activity screening.
- Li, Rui Juan,Yang, Guan E.,Bai, Hong Juan,Zhang, Qiong,Li, Jian Kuan,Li, Qing Shan,Zhang, Zhao Ming
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- An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain
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The distribution of pyrrolidine-type iminosugars with a long-side chain appears to be restricted to the relatively unrelated plant families Moraceae, Campanulaceae, and Hyacinthaceae. In a search for glycosidase inhibitors in these plant families, we isolated the 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) glucoside bearing the 1,2,11-trihydroxyundec-4-ene side chain at the C-1α position from the roots of Adenophora triphylla. This iminosugar was a powerful and selective inhibitor of coffee bean α-galactosidase, with an IC 50 value of 8 μM.
- Kato, Atsushi,Hollinshead, Jackie,Yamashita, Yukiko,Nakagawa, Shinpei,Koike, Yuriko,Adachi, Isao,Yu, Chu-Yi,Fleet, George W.J.,Nash, Robert J.
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- Polygalins D-G, four new flavonol glycosides from the aerial parts of Polygala sibirica L. (Polygalaceae)
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Four new flavonol glycosides (1-4), polygalins D-G, together with 12 known flavonoids (5-16) were isolated from the aerial parts of Polygala sibirica L. The chemical structures of these compounds were characterised by NMR and ESI-MS spectroscopic data and acid hydrolysis results. This report is a continuous research work on the systematic chemical investigations of plants of the genus Polygala in our laboratory.
- Song, Yue-Lin,Zhou, Guan-Shen,Zhou, Si-Xiang,Jiang, Yong,Tu, Peng-Fei
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- Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases
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Small molecule irreversible inhibitors are valuable tools for determining catalytically important active-site residues and revealing key details of the specificity, structure, and function of glycoside hydrolases (GHs). β-glucans that contain backbone β(1,3) linkages are widespread in nature, e.g., mixed-linkage β(1,3)/β(1,4)-glucans in the cell walls of higher plants and β(1,3)glucans in yeasts and algae. Commensurate with this ubiquity, a large diversity of mixed-linkage endoglucanases (MLGases, EC 3.2.1.73) and endo-β(1,3)-glucanases (laminarinases, EC 3.2.1.39 and EC 3.2.1.6) have evolved to specifically hydrolyze these polysaccharides, respectively, in environmental niches including the human gut. To facilitate biochemical and structural analysis of these GHs, with a focus on MLGases, we present here the facile chemo-enzymatic synthesis of a library of active-site-directed enzyme inhibitors based on mixed-linkage oligosaccharide scaffolds and N-bromoacetylglycosylamine or 2-fluoro-2-deoxyglycoside warheads. The effectiveness and irreversibility of these inhibitors were tested with exemplar MLGases and an endo-β(1,3)-glucanase. Notably, determination of inhibitor-bound crystal structures of a human-gut microbial MLGase from Glycoside Hydrolase Family 16 revealed.
- Jain, Namrata,Tamura, Kazune,Déjean, Guillaume,Van Petegem, Filip,Brumer, Harry
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p. 1968 - 1984
(2021/05/26)
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- Anti-inflammatory active components of the roots of Datura metel
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One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we
- Qin, Ze,Zhang, Jin,Chen, Liang,Liu, Shu-Xiang,Zhao, Hai-Feng,Mao, Hui-Min,Zhang, Hong-Yang,Li, De-Fang
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p. 392 - 398
(2020/03/30)
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- Method for preparing lactic acid through catalytically converting carbohydrate
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The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.
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Paragraph 0029-0040
(2020/11/01)
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- Formation of Chiral Structures in Photoinitiated Formose Reaction
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The possibility to synthesize biologically important sugars and other chiral compounds without any initiators in the UV-initiated reaction of formaldehyde in aqueous solution has been shown for the first time. An optically active condensed phase due to an
- Stovbun,Skoblin,Zanin,Tverdislov,Taran,Parmon
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p. 108 - 116
(2018/04/05)
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- Cyprotuoside C and cyprotuoside D, two new cycloartane glycosides from the rhizomes of Cyperus rotundus
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Cyprotuoside C (1) and cyprotuoside D (2), two new cycloartane glycosides were isolated from the ethanol extract of the rhizomes of Cyperus rotundus. Their structures were identified as 24R-9,10-seco-cycloartan- 1(10),9(11)-dien-3β,7β,24,25-tetraol 3-O-β-
- Lin, San-Qing,Zhou, Zhong-Liu,Li, Chun-Yan
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- Shape-selective Valorization of Biomass-derived Glycolaldehyde using Tin-containing Zeolites
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A highly selective self-condensation of glycolaldehyde to different C4 molecules has been achieved using Lewis acidic stannosilicate catalysts in water at moderate temperatures (40–100 °C). The medium-sized zeolite pores (10-membered ring framework) in Sn-MFI facilitate the formation of tetrose sugars while hindering consecutive aldol reactions leading to hexose sugars. High yields of tetrose sugars (74 %) with minor amounts of vinyl glycolic acid (VGA), an α-hydroxyacid, are obtained using Sn-MFI with selectivities towards C4 products reaching 97 %. Tin catalysts having large pores or no pore structure (Sn-Beta, Sn-MCM-41, Sn-SBA-15, tin chloride) led to lower selectivities for C4 sugars due to formation of hexose sugars. In the case of Sn-Beta, VGA is the main product (30 %), illustrating differences in selectivity of the Sn sites in the different frameworks. Under optimized conditions, GA can undergo further conversion, leading to yields of up to 44 % of VGA using Sn-MFI in water. The use of Sn-MFI offers multiple possibilities for valorization of biomass-derived GA in water under mild conditions selectively producing C4 molecules.
- Tolborg, S?ren,Meier, Sebastian,Saravanamurugan, Shunmugavel,Fristrup, Peter,Taarning, Esben,Sádaba, Irantzu
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p. 3054 - 3061
(2016/11/17)
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- Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d -Gulose, 6-Deoxy- d -gulose, l -Glucose, 6-Deoxy- l -glucose, and Related Sugars
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Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.
- Liu, Zilei,Yoshihara, Akihide,Jenkinson, Sarah F.,Wormald, Mark R.,Estévez, Ramón J.,Fleet, George W.J.,Izumori, Ken
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p. 4112 - 4115
(2016/08/30)
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- Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides
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Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre-treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n-butanol has only a slight effect on the recrystallization of ball-milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a pivotal aspect with respect to energy consumption. This process was successfully transposed to wheat straw from which butyl glycosides and xylosides were produced in good yields. Butyl glycosides and xylosides are important chemicals as they can be used as hydrotropes but also as intermediates in the production of valuable amphiphilic alkyl glycosides.
- Boissou, Florent,Sayoud, Nassim,De Oliveira Vigier, Karine,Barakat, Abdellatif,Marinkovic, Sinisa,Estrine, Boris,Jér?me, Fran?ois
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p. 3263 - 3269
(2015/10/19)
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- Catalytic effect of aluminium chloride on the example of the conversion of sugar model compounds
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Abstract In this work, the catalytic effect of the Bronsted acid hydrochloric acid, the Bronsted base sodium hydroxide and the Lewis acid AlCl3 on the conversion of biomass derived carbohydrates is investigated. On the example of the glycolaldehyde conversion, it is shown that the Lewis acid catalyses the ketol-endiol-tautomerism, the dehydration, the retro-aldol-reaction and the benzilic-acid-rearrangement. The main products are C4- and C6-carbohydrates as well as their secondary products 2-hydroxybut-3-enoic acid 1 and several furans. Under the same reaction conditions hydrochloric acid catalyzes mainly the dehydration and sodium hydroxide the tautomerism and subsequent aldolization.
- Schwiderski, Martin,Kruse, Andrea
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- Effects of polysaccharide on chicks co-infected with Bordetella avium and Avian leukosis virus
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Chicks' co-infection with immunosuppressive virus and bacteria seriously threaten the development of the poultry industry. In this study, a model was established in which chicks were injected with either subgroup B ALV (ALV-B) + Bordetella avium (B. avium), or ALV-B + B. avium + Taishan Pinus massoniana pollen polysaccharide (TPPPS), or B. avium only, or B. avium + TPPPS. The data showed that the group injected with ALV-B and B. avium exhibited significant inhibition of the immune function and therefore increased pathogenicity compared with the group injected with B. avium-only. Application of TPPPS effectively alleviated immunosuppression, and body weights increased sharply in the TPPPS groups compared with non-TPPPS groups. To some extent, TPPPS may reduce the proliferation of ALV-B. These results suggest that Pinus pollen polysaccharides are beneficial treating co-infections with immunosuppressive virus and bacteria and therefore have potential for development into safe and effective immunoregulator.
- Guo, Fanxia,Xue, Cong,Wu, Cun,Zhao, Xue,Qu, Tinghe,He, Xiaohua,Guo, Zhongkun,Zhu, Ruiliang
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- Studies on the flavone glycosides from Fructus Kochiae
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A series of flavone glycosides were isolated from Fructus Kochiae for the first time, including two new flavone glycosides. The structures were established by interpretation of their spectroscopic data. Two new flavone glycosides are quercetin 3-O-β-d-apiofuranosyl-(1 → 2)-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (1) and quercetin 3-O-l-rhamnopyranosyl-(1 → 6)-β-d-galactopyranosyl-7-O-β-d- sophoroside (2). The others are quercetin 7-O-β-d-glucopyranoside (3), quercetin 3-O-β-d-apiofuranosyl-(1 → 2)-β-d-galactopyranoside (4), quercetin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (5), and quercetin 7-O-β-d-sophoroside (6).
- Xu, Yun-Hui,Huang, Hao,Zhang, Nian,Kong, De-Yun,Hua, Mo-Li
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p. 141 - 147
(2014/02/14)
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- Three new triterpene glycosides from Ilex asprella
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Three new sulfated triterpene glycosides, asprellanosides C-E (1-3), were isolated from the roots of Ilex asprella. Their structures were elucidated as 3β-[(2-O-sulfo-β-D-xylopyranosyl)oxy]urs-12,19(29)-diene-28-oic acid 28-β-D-glucopyranoside (1), 3β-[(2
- Zhang, Zhen-Xia,Fu, Qiang,Zheng, Ken Yu-Zhong
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p. 453 - 458
(2013/09/02)
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- Productive sugar isomerization with highly active Sn in dealuminated β zeolites
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A water-tolerant Lewis acid catalyst was synthesized by grafting Sn IV in isopropanol under reflux onto dealuminated zeolites with the BEA (β) topology. This synthesis method allows the production of highly active Snβ-type catalysts without the need for long hydrothermal syntheses or hydrogen fluoride, while using cheap Sn-precursors, industrially available β zeolites and standard catalyst synthesis unit operations. Extensive characterization of the best catalyst shows highly dispersed Sn in the zeolite matrix (XRD, 29Si MAS NMR and 1H MAS NMR) without the formation of SnO2 (XRD and UV-Vis). The catalyst was tested for the model isomerization of sugars such as glucose to fructose. The catalytic activity proved to be purely heterogeneous and the catalyst was recycled and reused without significant loss in activity. Isomerization productivities above 4 kg product per kg of catalyst per hour are reported with appreciably low Sn loadings, corresponding to exceptionally high turnover frequencies, viz. 500 cycles per Sn per hour at 110 °C, which surpass the activity per Sn of the original hydrothermally synthesized Snβ.
- Dijkmans, Jan,Gabriels, Dries,Dusselier, Michiel,De Clippel, Filip,Vanelderen, Pieter,Houthoofd, Kristof,Malfliet, Annelies,Pontikes, Yiannis,Sels, Bert F.
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p. 2777 - 2785
(2013/10/08)
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- Acyl glycosides with rare β-d-apiofuranosyl-β-d-glucopyranosyl- β-d-apiofuranosyl from Erycibe hainanesis
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Three new acyl glycosides with rare β-d-apiofuranosyl-(1 → 2)-[β-d-apiofuranosyl-(1 → 6)]-β-d-glucopyranosyl moieties, 2-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranosyl)-β-d-glucopyranosyl] -isopropyl alcohol (1), 1-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranos
- Feng, Zi-Ming,Song, Shuang,He, Jun,Yang, Ya-Nan,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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- Reactivity of poly-, di-, and monosaccharides in their hydrolysis in subcritical water
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The reactivity of the water-soluble sodium salt of carboxymethyl cellulose (CMC), sucrose, glucose, and fructose in subcritical water at 120-320°C is reported. A mathematical model is suggested to describe the variation of the CMC molar mass during hydrolysis at various temperatures and reaction times. Kinetic parameters of the conversions of CMC, sucrose, glucose, and fructose in subcritical water are presented. High temperatures and short reaction times are favorable for the formation of monosaccharides from CMC. Pleiades Publishing, Ltd., 2012.
- Khudoshin,Goryainov,Lunin,Bogdan
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scheme or table
p. 19 - 24
(2012/07/02)
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- Development of a chemical strategy to produce rare aldohexoses from ketohexoses using 2-aminopyridine
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Rare sugars are monosaccharides that are found in relatively low abundance in nature. Herein, we describe a strategy for producing rare aldohexoses from ketohexoses using the classical Lobry de Bruyn-Alberda van Ekenstein transformation. Upon Schiff-base formation of keto sugars, a fluorescence-labeling reagent, 2-aminopyridine (2-AP), was used. While acting as a base catalyst, 2-AP efficiently promoted the ketose-to-aldose transformation, and acting as a Schiff-base reagent, it effectively froze the ketose-aldose equilibrium. We could also separate a mixture of Sor, Gul, and Ido in their Schiff-base forms using a normal-phase HPLC separation system. Although Gul and Ido represent the most unstable aldohexoses, our method provides a practical way to rapidly obtain these rare aldohexoses as needed.
- Hasehira, Kayo,Miyanishi, Nobumitsu,Sumiyoshi, Wataru,Hirabayashi, Jun,Nakakita, Shin-Ichi
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experimental part
p. 2693 - 2698
(2011/12/21)
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- Phenolic glycosides from the Chinese liverwort reboulia hemisphaerica
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Four new phenolic glycosides, named rebouosides A-D (1-4, resp.), along with three known ones 2-(3,4-dihydroxyphenyl)ethyl 2-O-α-L- rhamnopyranosyl-β-D-allopyranoside (5), 2-(3,4-dihydroxyphenyl)ethyl β-D-allopyranoside (6), 2-(3,4-dihydroxyphenyl)ethyl β-D- glucopyranoside (7), and a nucleoside, inosine (8), were isolated from Chinese liverwort Reboulia hemisphaerica. Their structures were elucidated by acidic hydrolysis and extensive spectroscopic methods, including 2D-NMR techniques.
- Wang, Li-Ning,Guo, Dong-Xiao,Wang, Shu-Qi,Wu, Chang-Sheng,Rehman, Mujeeb Ur,Lou, Hong-Xiang
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experimental part
p. 1146 - 1152
(2011/08/05)
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- Phyteumosides A and B: New saponins with unique triterpenoid aglycons from Phyteuma orbiculare L.
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Phyteumosides A (1) and B (2), two saponins with unprecedented triterpenoid aglycons, were isolated from the aerial parts of Phyteuma orbiculare (Campanulaceae). Their structures were elucidated by spectroscopic and chemical methods and corroborated by X-ray diffraction analyses of the aglycons obtained through enzymatic hydrolysis. The aglycon of 1 can be considered as an incompletely cyclized onoceroid or gammaceroid triterpene with two additional tetrahydropyran rings arising from oxygen bridges. Compound 2 possesses a new 17-polypodene aglycon.
- Abbet, Christian,Neuburger, Markus,Wagner, Trixie,Quitschau, Melanie,Hamburger, Matthias,Potterat, Olivier
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supporting information; experimental part
p. 1354 - 1357
(2011/05/15)
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- Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa
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Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.
- Morikawa, Toshio,Pan, Yingni,Ninomiya, Kiyofumi,Imura, Katsuya,Yuan, Dan,Yoshikawa, Masayuki,Hayakawa, Takao,Muraoka, Osamu
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experimental part
p. 1403 - 1407
(2010/11/19)
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- HYBRID COMPOUNDS BASED ON POLYOL(S) AND AT LEAST ONE OTHER MOLECULAR ENTITY, POLYMERIC OR NON-POLYMERIC, IN PARTICULAR OF THE POLYORGANOSILOXANE TYPE, PROCESS FOR THE PREPARATION THEREOF, AND APPLICATIONS THEREOF
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The invention relates to novel hybrid compounds comprising at least one polyon entity (Po)—for example oligomer or polymer—in which at least one of the hydroxyl functions of Po is substituted by at least one entity A that can be of a variable nature, for example polymer (e.g. polyorganosiloxane-POS), hydrocarbonated or mineral. The bond Ro between the entity Po and the entity A is obtained by means of “click chemistry” and corresponds to formula (II.1) or (II.2), Z representing —CH— or —N—. A is an entity selected from the group comprising the various polyols of Po, polyorganosiloxanes (POS), polyalkylene glycols, polyamides, polyesters, polystyrenes, alkyls, alkenyls, alkynyls, aryls, and combinations thereof, in addition to mineral materials such as silica and the combinations thereof. Said hybrid components can be used as emulsifiers, especially for cosmetics.
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- Syntheses of mucin-type O-glycopeptides and oligosaccharides using transglycosylation and reverse-hydrolysis activities of Bifidobacterium endo-α-N-acetylgalactosaminidase
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Endo-α-N-acetylgalactosaminidase catalyzes the release of Galβ1-3GalNAc from the core 1-type O-glycan (Galβ1-3GalNAcα1- Ser/Thr) of mucin glycoproteins and synthetic p-nitrophenyl (pNP) α-linked substrates. Here, we report the enzymatic syntheses of core 1 disaccharide-containing glycopeptides using the transglycosylation activity of endo-α-N-acetylgalactosaminidase (EngBF) from Bifidobacterium longum. The enzyme directly transferred Galβ1-3GalNAc to serine or threonine residues of bioactive peptides such as PAMP-12, bradykinin, peptide-T and MUC1a when Galβ1-3GalNAcα1-pNP was used as a donor substrate. The enzyme was also found to catalyze the reverse-hydrolysis reaction. EngBF synthesized the core 1 disaccharide-containing oligosaccharides when the enzyme was incubated with either glucose or lactose and Galβ1-3GalNAc prepared from porcine gastric mucin using bifidobacterial cells expressing endo-α-N- acetylgalactosaminidase. Synthesized oligosaccharides are promising prebiotics for bifidobacteria.
- Ashida, Hisashi,Ozawa, Hayato,Fujita, Kiyotaka,Suzuki, Shun'Ichi,Yamamoto, Kenji
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body text
p. 125 - 132
(2011/10/09)
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- Diterpene glycosides from the seeds of Pharbitis nil
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Six new ent-kaurane diterpene glycosides, pharbosides A-F (1-6), and a new ent-gibbane diterpene glycoside, pharboside G (7), together with three known ent-kaurane diterpenoids, 7β,16β,17-trihydroxy-ent-kauran-6α,19- olide (8), 6β,7β,16α,17-tetrahydroxy-ent-kauranoic acid (9), and 6β,7β,16β,17-tetrahydroxy-ent-kauranoic acid (10), were isolated from an ethanolic extract of the seeds of Pharbitis nil. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR analysis. The absolute configurations of the compounds were clarified by CD spectroscopic studies. Full NMR data assignments of the three known compounds (8-10) are reported. The isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines.
- Ki, Hyun Kim,Sang, Un Choi,Kang, Ro Lee
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experimental part
p. 1121 - 1127
(2011/04/22)
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- COSMETIC COMPOSITION CONTAINING HYDROLYSATES OF ICARIIN
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The present invention relates to a cosmetic composition containing hydrolysates of icariin, and more particularly, a cosmetic composition containing hydrolysates of icariin including icaritin, icariside I and icariside II. The hydrolysates of icariin is prepared by a method comprising the steps of: (a) obtaining an extract from a plant containing icariin using water or an organic solvent; and (b) hydrolyzing the plant extract with an acid, a base, an enzyme or a microorganism producing the enzyme. The cosmetic composition according to the present invention is employed for anti-oxidant, anti-aging, whitening or anti-wrinkling effects.
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Page/Page column 15
(2008/06/13)
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- ACCELERATOR FOR MINERAL ABSORPTION AND USE THEREOF
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The present invention has an object to provide an accelerator for mineral absorption and a composition containing the accelerator. The object is solved by providing an accelerator for mineral absorption comprising cyclic tetrasaccharide and/or saccharide derivatives thereof and a composition containing the accelerator.
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Page/Page column 14
(2008/06/13)
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- Mitochondrially targeted antioxidants
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The invention provides mitochondrially targeted antioxidant compounds comprising a lipophilic cation moiety covalently coupled to a glutathione peroxidase mimetic. These compounds can be used to treat patients who would benefit from the reduction of oxidative stress.
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- Kinetic and chemical studies on the isomerization of monosaccharides in N-methylmorpholine-N-oxide (NMMO) under Lyocell conditions
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The Lyocell process is a modern and environmentally fully compatible industrial fiber-making technology. Cellulosic pulp is dissolved without chemical derivatization in a melt of N-methylmorpholine-N-oxide monohydrate (NMMO). In the present work, the reactions of monosaccharides under Lyocell conditions were investigated in detail, using capillary zone electrophoresis as the analytical technique to clarify the composition of reaction mixtures and to follow the kinetics. Under Lyocell conditions, xylose and glucose undergo two competitive reactions: rapid conversion to nonreducing products, and complete isomerization involving the whole carbohydrate backbone, via ketose intermediates. Sugar acids are present in minor amounts only, as demonstrated by employing isotopically labeled material for NMR techniques.
- Adorjan, Immanuel,Sjoeberg, John,Rosenau, Thomas,Hofinger, Andreas,Kosma, Paul
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p. 1899 - 1906
(2007/10/03)
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- Methods for treating plants and enhancing plant growth using polyacylglycosides and/or polyalkylglycosides and formulations for same
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Methods and formulations for treating plants and enhancing plant growth and for safening high concentrations of one or more phytocatalysts, wherein one or more formulations, comprising, a high concentration of one or more phytocatalysts, and an effective amount of one or more polyacylglycosides and polyalkylglycosides; and isomers, and metabolites, salts, hydrates, esters, amines, and derivatives of the polyacylglycosides and polyalkylglycosides, and combinations thereof, is applied to the plants.
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- A new convergent route to aldohexoses from a common chiral building block.
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[reaction in text] A diastereocontrolled route to the eight aldohexoses has been developed starting from a common cyclohexanoid chiral building block.
- Honzumi,Taniguchi,Ogasawara
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p. 1355 - 1358
(2007/10/03)
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- Saponins isolated from Allium chinense G. DON and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug
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Investigation of the Chinese crude drug 'Xiebai,' the bulbs of Allium chinense G. DON (Liliaceae), led to the isolation of 2 saponins, xiebai- saponin I (laxogenin 3-O-β-xylopyranosyl (1→4)-[α-arabinopyranosyl (1→6)]-β-glucopyranoside) (1) and laxogenin 3-O-α-arabinopyranosyl (1→6)- β-glucopyranoside (2), and the aglycone, laxogenin (3), together with 2 chalcones, isoliquiritigenin (4) and isoliquiritigenin-4-O-glucoside (5), and β-sitosterol glucoside (6). Compounds 15 were tested in vitro for their inhibitory effect on the 12-O-tetradecanoylphorbol-13-acetate (TPA)- stimulated 32Pi-incorporation into phospholipids of HeLa cells. In addition to this, laxogenin (3) was proven to have an antitumor-promoting activity in a two-stage lung carcinogenesis experiment.
- Baba, Masaki,Ohmura, Masayoshi,Kishi, Naoki,Okada, Yoshihito,Shibata, Shoji,Peng, Jeng,Yao, Shin-Sen,Nishino, Hoyoku,Okuyama, Toru
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p. 660 - 662
(2007/10/03)
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- Back to the sugars: A new enantio and diastereocontrolled route to hexoses from furfural
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An integrated enantio and diastereocontrolled route to both enantiomers of the eight possible hexoses has been explored starting from furfural, by employing the Sharpless asymmetric dihydroxylation as a key step. At the present, a route to six of the eight possible hexoses has been established. The present synthesis may be taken as a reversion of the sugar-originated furfural to the sugars via a levoglucosenone, a pyrolysate of cellulose, type intermediate.
- Takeuchi, Miwako,Taniguchi, Takahiko,Ogasawara, Kunio
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p. 341 - 354
(2007/10/03)
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- Use of wastewater sludge as a raw material for production of L-lactic acid
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This study utilizes wastewater sludges to produce L-lactic acid, a precursor of biodegradable plastic. The high concentrations of cellulose contained in the sludge, derived from a paper manufacturing facility, have been found to be convertible to L-lactic acid at a rate as high as 6.91 g/L. To achieve such a high conversion rate, the sludge must be pretreated with cellulase. This pretreatment includes inoculation of the sludge with lactic acid bacteria, strain LA1, after the sludge has been subjected to enzymatic hydrolysis. This study utilizes wastewater sludges to produce L-lactic acid, a precursor of biodegradable plastic. The high concentrations of cellulose contained in the sludge, derived from a paper manufacturing facility, have been found to be convertible to L-lactic acid at a rate as high as 6.91 g/L. To achieve such a high conversion rate, the sludge must be pretreated with cellulase. This pretreatment includes inoculation of the sludge with lactic acid bacteria, strain LA1, after the sludge has been subjected to enzymatic hydrolysis.
- Nakasaki, Kiyohiko,Akakura, Naoki,Adachi, Tomohiko,Akiyama, Tetsuo
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p. 198 - 200
(2007/10/03)
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- Process for isomerization of compound of aldose structure into compound of ketose structure, and isomerization agent or accelerator used therein
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A process is provided which comprises isomerizing a compound having a ketose structure by the use of or in the presence of an organogermanium compound having a structural portion represented by formula (I): STR1 Due to the use or presence of the organogermanium compound, the process is free from the problems of the prior art, and is capable of isomerizing a compound having an aldose structure into a compound having a ketose structure at a high isomerization ratio without requiring any special apparatus or any complicated operation.
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- Total synthesis of the L-hexoses
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Enantiomerically pure polyhydroxylated natural products are synthesized by using a reiterative two-carbon extension cycle consisting of four key transformations. The generality and efficiency of this methodology are demonstrated in the total synthesis of all eight L-hexoses.
- Ko, Soo Y.,Lee, Albert W. M.,Masamune, Satoru,Reed III, Lawrence A.,Sharpless, K. Barry,Walker, Frederick J.
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p. 245 - 264
(2007/10/02)
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- STUDY OF THE EFFECT OF ORGANIC SOLVENTS ON THE SYNTHESIS OF LEVAN AND THE HYDROLYSIS OF SUCROSE BY Bacillus subtilis LEVANSUCRASE
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The equilibrium between the hydrolase and synthetase activities of levansucrase was determined by progressively substituting water with various organic solvents in the enzymic reaction medium.In the presence of high concentrations of these solvents, the enzyme displayed anly synthetase activity.The levan obtained under such conditions had Mr-106 and presented a low molecular dipersity.In the presence of solvent, the Km values for sucrose and raffinose remained unchanged, but the kcat values were five times higher in comparison to the same constants determined for an aqueous medium.
- Chambert, Regis,Petit-Glatron, Marie-Francoise
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p. 117 - 124
(2007/10/02)
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- EVIDENCE OF STABLE HYDROGEN-BONDED IONS DURING ISOMERZATION OF HEXOSES IN ALKALI
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Epimeric pairs of aldohexoses and related ketohexose were isomerized in aqueous KOH at various temperatures and pH values, and the mixtures then analyzed by h.p.l.c. on either a cation-exchange resin or a reversed-phase column.It was found that the propertions of starting aldohexoses remaining after several days often exceeded those of the same that were formed from the epimeric aldoses and the corresponding ketoses.The difference with allose, gulose, and mannose was much larger than with other aldohexoses.These differences are rationalized by assuming that anomers having the OH groups attached to C-1, C-2, and C-3 in an axial-equatorial-axial or an equatorial-axial-equatorial arrangement form especially stable, hydrogen-bonded ions or molecular complexes that disturb the equilibrium state and affect the isomerization and mutarotation reactions.
- El Khadem, Hassan S.,Ennifar, Sofiane,Isbell, Horace S.
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- Glycosyl Nervogenic Acid Esters of Carbohydrates from Anodendron affine (Anodendron. VI)
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Esters of p-O-glucosyl- and p-O-primverosylnervogenic acid with some carbohydrates (including dambonitol, glucose, and sucrose) were isolated from the seeds, unripened fruits, and caules of Anodendron affine DRUCE.The locations of the nervogenic acid moiety on dambonitol and sucrose were determined on the basis of spectral and chemical evidence.Keywords--Anodendron affine; Apocynacea; 3,5-diprenyl-4-hydroxybenzoic acid; nervogenic acid; 1,3-di-O-methyl-myo-inositol; dambonitol; 5-acyldambonitol; 6-acyldambonitol; 6glc-O-(p-O-glucosyl)nervogenoylsucrose; anodendrosin
- Abe, Fumiko,Yamauchi, Tatsuo
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p. 2712 - 2720
(2007/10/02)
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- Kinetics, Catalysis, and Mechanism of the Secondary Reaction in the Final Phase of the Formose Reaction
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In the final phase of the formose reaction sugars are formed by the reaction of glycolaldehyde, glyceraldehyde and dihydroxyacetone.The application of high-pressure liquid chromatography allows for the first time to investigate intermediate and final products quantitatively.The results of kinetical investigations allow to suggest a reaction mechanism for the secondary reaction in the final phase of the formose reaction.This mechanism is compared with that of the starting phase and other known mechanisms.From the results metal ion-catalyzed aldol reactions have to be assumed.
- Harsch, Guenther,Bauer, Hermann,Voelter, Wolfgang
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p. 623 - 635
(2007/10/02)
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