- New 3,4-seco-diterpene and coumarin derivative from the leaves of Trigonostemon flavidus Gagnep
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Two new compounds named trigoflavidus A (1) and trigoflavidus B (2), and eight known compounds, trigoflavidone (3), heterophypene (4), howpene C (5), 3,4-seco-sonderianol (6), trigonochinene C (7), fraxidin (8), isofraxidin (9), and isofraxetin (10) were isolated from the leaves of Trigonostemon flavidus Gagnep. by various chromatographic methods. Their chemical structures were elucidated via UV, IR, HR-ESI-MS and NMR spectroscopic methods and divided into two groups including six 3,4-seco-diterpenes (1, 3-7) and four coumarins (2, 8-10). Absolute configurations at stereocenters of compound 1 were confirmed by comparison of its CD spectra with those of the TD-DFT calculations. At a concentration of 30 μM, compounds 1–10 exhibited weak cytotoxic activity toward LU1, HepG2, MCF7, and SKMel2 human cell lines (cell viability all over 50%).
- Ban, Ninh Khac,Linh, Tran My,Mai, Nguyen Chi,Tai, Bui Huu,Nhiem, Nguyen Xuan,Hoang, Nguyen Huy,Kiem, Phan Van
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- Seven new glycosides from the leaves of Datura metel L.
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Seven new glycosides (1–7) and seventeen known analogues (8–24) were isolated from the leaves of Datura metel L. The structures of these compounds were all elucidated by detailed spectroscopic analyses and comparison with literature values. All isolates were evaluated for cytotoxicity against Hela, MGC-803, Ishikawa cell lines and compounds 6, 7, 14–17 and 24 exhibited different degrees of antiproliferative effects.
- Tan, Jin-Yan,Liu, Yan,Cheng, Yan-Gang,Sun, Yan-Ping,Li, Xiao-Mao,Guan, Wei,Pan, Juan,Yang, Bing-You,Kuang, Hai-Xue
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- Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia
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The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1-3). The structures of these compounds were determined to be (19R,23R)-5β, 19-epoxy-19-methoxycucurbita-6,24-diene-3β, 23-diol 3-O-β-D- allopyranoside (1), (23R)-5β, 19-epoxycucurbita-6,24-diene-3β, 23-diol 3-O-β-D-allopyranoside (2), and (19R)-5β, 19-epoxy-19,25- dihydroxycucurbita-6,23(E)-diene-3β-ol 3-O-β-D-glucopyranoside (3), by chemical and spectroscopic methods.
- Kim, Young Ho,Nhiem, Nguyen Xuan,Kiem, Phan Van,Minh, Chau Van,Ban, Ninh Khac,Cuong, Nguyen Xuan,Ha, Le Minh,Tai, Bui Huu,Quang, Tran Hong,Tung, Nguyen Huu
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- Two new compounds from Aconitum tanguticum
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A phytochemical investigation on the whole plant of Aconitum tanguticum (Ranunculaceae) resulted in the isolation and characterization of two new phenylpropanoid glycosides (1 and 2). Their structures were elucidated as 4-hydroxyphenethoxy-8-O-β-d-[6-O-(4-O-β-d-glucopyranosyl)-sinapoyl] -glucopyranoside (1) and 3,4-dimethoxy-trans-cinnamic acid-9-O-β-d- allopyranoside (2) on the basis of spectroscopic data (1D NMR, 2D NMR, and MS) and comparison with the literature data. 2014
- Li, Yan-Rong,Xu, Lu,Li, Chun,Wang, Zhi-Min,Yang, Li-Xin
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- Acute and sub-chronic toxicity of D-allose in rats
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We examined the acute and sub-chronic toxicity of D-allose in rats. In the acute toxicity test, the calculated LD50 value was 20.5 g/kg. In the sub-chronic toxicity test, no difference was found among the four groups in most of the serum chemical and hematological test results. These results suggest that D-allose is not toxic to rats.
- Iga, Yusuke,Nakamichi, Kazunori,Shirai, Yoko,Matsuo, Tatsuhiro
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- Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects
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Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1-5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC50 values of 200-409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1-5 for inhibitory effects against activation of (±)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1-3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.
- Akihisa, Toshihiro,Higo, Naoki,Tokuda, Harukuni,Ukiya, Motohiko,Akazawa, Hiroyuki,Tochigi, Yuichi,Kimura, Yumiko,Suzuki, Takashi,Nishino, Hoyoku
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- Chemical constituents from cimicifuga dahurica and their anti-proliferative effects on MCF-7 breast cancer cells
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This study was designed to search for novel anti-cancer compounds from natural plants. The 70% ethanolic extract from the rizhomes of Cimicifuga dahurica (Turcz.) Maxim. (Ranunculaceae) was found to possess significant in vitro anti-proliferative effects
- Thanh Huyen, Chu Thi,Thuy Luyen, Bui Thi,Khan, Ghulam Jilany,Oanh, Ha Van,Hung, Ta Manh,Li, Hui-Jun,Li, Ping
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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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- 5β,19-Epoxycucurbitane triterpenoids from momordica charantia and their anti-inflammatory and cytotoxic activity
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Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A-E (1 -5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70% EtOH extract of the fresh fruits of Momordica charantia. The
- Liaw, Chia-Ching,Huang, Hui-Chi,Hsiao, Ping-Chun,Zhang, Li-Jie,Lin, Zhi-Hu,Hwang, Syh-Yuan,Hsu, Feng-Lin,Kuo, Yao-Haur
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- HPLC-ESIMSn profiling, isolation, structural elucidation, and evaluation of the antioxidant potential of phenolics from Paepalanthus geniculatus
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The methanol extract of the flowers of Paepalanthus geniculatus Kunth. showed radical-scavenging activity in the TEAC assay. An analytical approach based on HPLC-ESIMSn was applied to obtain the metabolite profile of this extract and led to the rapid identification of 19 polyphenolic compounds comprising flavonoids and naphthopyranones. The new naphthopyranone (10, 16), quercetagetin (1, 5, 7, 13), and galetine derivatives (9, 11, 17, 19), and a flavonol glucoside cyclodimer in the truxillate form (12), were identified. Compounds 2, 6, and 7 showed the highest antioxidant capacity and ability to affect the levels of intracellular ROS in human prostate cancer cells (PC3).
- Pereira Do Amaral, Fabiano,Napolitano, Assunta,Masullo, Milena,Campaner Dos Santos, Lourdes,Festa, Michela,Vilegas, Wagner,Pizza, Cosimo,Piacente, Sonia
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- ISOLATION AND CHARACTERIZATION OF (E)-4-HYDROXY-2-(HYDROXYMETHYL)BUT-2-ENYL β-D-ALLOPYRANOSIDE, THE MAJOR SOLUBLE CARBOHYDRATE IN LEAVES OF THE FERN Cardiomanes reniforme
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A novel glycoside, (E)-4-hydroxy-2-(hydroxymethyl)but-2-enyl β-D-allopyranoside (1, cardiomanol) has been identified as the major soluble carbohydrate in the leaves of Cardiomanes reniforme.The structure of 1 was established by chemical and spectroscopic methods.
- Redgwell, Robert J.,Beever, Ross E.,Bieleski, Roderick L.,Laracy, Elaine P.,Benn, Michael H.
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- α-Glucosidase inhibition properties of cucurbitane-type triterpene glycosides from the fruits of Momordica charantia
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Fourteen cucurbitane-type triterpene glycosides (1-14) were isolated from a methanol extract of Momordica charantia fruits, including three new compounds, charantosides A-C (1, 5, 6). Their structures were elucidated by chemical and spectroscopic methods. All isolated compounds were evaluated for α-glucosidase inhibitory effect. Of which, 12 and 13 showed moderate inhibitory activity against α-glucosidase. Whereas, 2, 3, 6-11, and 14 showed weak inhibitory activity, and 1, 4, and 5 were inactive.
- Nhiem, Nguyen Xuan,Kiem, Phan Van,Minh, Chau Van,Ban, Ninh Khac,Cuong, Nguyen Xuan,Tung, Nguyen Huu,Ha, Le Minh,Ha, Do Thi,Tai, Bui Huu,Quang, Tran Hong,Ngoc, Tran Minh,Kwon, Young-In,Jang, Hae-Dong,Kim, Young Ho
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- Three new phenolic glycosides from the Tibetan medicinal plant Aconitum tanguticum
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Three new phenolic glycosides, such as (Z)-sinapic acid-4-O-β-d- allopyranoside (1), 3,4-dihydroxyphenethoxy-8-O-β-d-[6-O-(4-O-β-d- glucopyranosyl)-feruloyl]-glucopyranoside (2), and 4-dihydroxyphenethoxy-8-O- β-d-[6-O-(4-O-β-d-glucopyranosyl)-feruloyl]-g
- Xu, Lu,Luo, Ming,Lin, Li-Me,Zhang, Xiao,Li, Chun,Wang, Zhi-Min,Luo, Yong-Ming
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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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- Flavonoids from Stachys annua Growing in Azerbaijan
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The new acylated flavonoid bioside 4′-O-methylisoscutellarein-7-O-[4-O-acetyl]allopyranosyl-(1→2)-glucopyranoside (1) was isolated from the aerial parts of Stachys annua L. (Lamiaceae). Subterranean organs yielded for the first time 4′-O-methylisoscutella
- Movsumov,Garayev,Baghdikian,Mabrouki,Herbette,Ollivier,Suleimanov,Garayev
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p. 261 - 262
(2018/04/16)
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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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- 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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- Three new phenolic glycosides from the whole plant of Aconitum tanguticum (Maxim.) Stapf
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Three new phenolic glycosides 2-(3-O-β-d-glucopyranosyl-4-hydroxyphenyl) ethanol 1-O-β-d-glucopyranoside (1), 2-(4-O-β-d-fructopyranosylphenyl) ethanol 1-O-β-d-galactopyranoside (2) and 3-methoxy-4-O-β-d-allopyranosyl acetophenone (3), along with nine known compounds (4-12), were isolated from the ethanol extract of the whole plant of Aconitum tanguticum (Maxim.) Stapf. Their structures were elucidated by analysis of spectroscopic data including 1D-, 2D-NMR and HRESIMS, and the reported literature data comparison. All the compounds were evaluated for their potential anti-inflammatory effects by the inhibition of TNF-α production on LPS-stimulated RAW264.7 macrophages. Compounds 1, 3, 5 and 7-9 showed certain inhibition activity and their IC50 values were 38.18, 27.64, 3.25, 84.45, 12.76 and 18.44 μg/mL, respectively.
- Li, Yan-Rong,Liu, Ting,Yan, Ren-Yi,Hui, Lian-Qiang,Lin, Li-Mei,Cao, Chun-Yu,Guo, Shan-Shan,Yang, Li-Xin,Feng, Wei-Hong,Li, Chun,Wang, Zhi-Ming
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p. 311 - 315
(2015/03/04)
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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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- 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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- 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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- Benzoic acid allopyranosides and lignan glycosides from the twigs of Keteleeria evelyniana
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Seven new compounds, including three benzoic acid allopyranosides keteleeroside A (1), keteleeroside B (2) and keteleeroside C (3), and four lignan glycosides 3′-demethylicariside E3 (4), isocupressoside B (5), 3-methoxyisocupressoside B (6), and isomassonianoside B (7), along with five known compounds (8 - 12), were isolated from the n-butanol part of the methanolic extract of the twigs of Keteleeria evelyniana. The structures of these compounds were elucidated mainly by the analysis of their NMR and MS data. All compounds were isolated from this genus for the first time. The skeleton of lignan glycoside 4 was isolated from the Pinaceae family for the first time. All compounds were evaluated for antimicrobial activity against Candida albicans and Staphylococcus aureus, and their cytotoxic activity against K562, HT-29, B16, BGC-823, BEL-7402, SGC-7901, U251, and A549 cancer cell lines was studied. Results indicated that none of the compounds showed antimicrobial or cytotoxic activity.
- Wen, Jun He,Zhao, Hui Fu,Hong, Jin Han,He, Yan,Guang, Zhi Zeng,Chang, Jiu Ji,Hong, Biao Chu,Yu, Mei Zhang,Ning, Hua Tan
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experimental part
p. 733 - 739
(2011/09/16)
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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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- Method for preparing C-6 phosphorylated D-aldohexoses and C-6 phosphorylated D-aldohexose derivatives
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The present invention concerns a method for preparing C-6 phosphorylated D-aldohexoses and C-6 phosphorylated D-aldohexose derivatives, and uses thereof. The method comprises incubating polyphosphate as sole source of phosphate donor and a polyphosphate-glucose phosphotransferase (polyphosphate: D-glucose 6-phosphotransferase, EC 2.7.1.63) in an aqueous solution with a D-aldohexose or a D-aldohexose derivative.
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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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- The effect of microwave irradiation on Mo(VI) catalyzed transformations of reducing saccharides
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Efficient microwave-assisted Mo(VI)-catalyzed transformations of the 10 most common aldoses are described. Both pentoses and hexoses were converted to the corresponding epimers in considerably shorter reaction times. The yields were comparable, or better compared to conventional synthetic methods.
- Hricoviniova, Zuzana
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p. 2131 - 2134
(2007/10/03)
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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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- 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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- 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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- 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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- 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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- A PHENOL ALLOSIDE FROM VIBURNUM WRIGHTII
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A new phenol alloside, p-hydroxyphenyl β-D-alloside, has been isolated from the leaves of Viburnum wrightii in addition to several known compounds.The structures were elucidated by spectroscopic and chemical methods. - Keywords: Viburnum wrightii; Caprifoliaceae; phenol alloside.
- Iwagawa, Tetsuo,Takahashi, Hideo,Munesada, Kiyotaka,Hase, Tsunao
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p. 468 - 469
(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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- THE FORMOIN REACTION
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The formoin reaction, i.e., the autocondensation of formaldehyde in an aprotic solvent catalysed by the conjugate base of a thiazolium ion, has been studied in detail.Glucose, galactose, dihyroxyacetone dimer, xylose, and arabinose have been identified as products.The influence of catalysts, temperature, basicity, and reaction time is documented.N,N-Dimethylformamide is a more convenient solvent than ether, benzene, or diglyme.Ethyldi-isopropylamine affords better yields of carbohydrate material than triethylamine.At =60 deg, aldol condensations are reduced to a minimum.After 1-2 h of reaction (depending on the conditions), the yields begin to decrease and become zero after ca. 24 h.
- Castells, Josep,Lopez-Calahorra, Francisco,Geijo, Fernando
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p. 197 - 208
(2007/10/02)
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- Kinetics of reactions of manganese(III) pyrophosphate with some hexitols
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Alditols are acyclic, polyhydric alcohols that are derived from aldoses and ketoses by reduction.Their wide-spread occurance in Nature, particularly in the lower forms of life, points to their biological importance.Compared to studies of the metal-ion oxidation of sugars, it seems that the oxidation of alditols has received little attention.Earlier, the oxidation of hexitols with cerium(IV) (ref. 1), cobalt(III) (ref. 2), and vanadium(V) (ref. 3) was reported, and we now describe oxidations with manganese(III) pyrophosphate.
- Fadnis, Anand G.,Kulshrestha, Sudhir K.
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p. 137 - 140
(2007/10/02)
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- Syntheses of the Two Epimeric 5'-Methylcytidines, their 5'-Phosphates and 3H>-5'-Pyrophosphates, and the Two 5'-Methyldeoxycytidines. A Novel Cytosine Anhydro-nucleoside with Two Oxygen Bridges between the Base and the Sugar
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In a series of experiments the starting materials were methyl 2,3-O-isopropylidene-β-D-allo- and -α-L-talofuranosides.These were converted in two steps into the corresponding 2,3,5-tri-O-benzoyl esters, (5) and (11), which were coupled with N-acetylbis(trimethylsilyl)cytosine in the presence of tin(IV) chloride, to the protected nucleosides (19) and (20).Alkaline methanolysis gave the free cytidine homologues, 1-(6-deoxy-β-D-allo- and -α-L-talo-furanosyl)cytosine (23) and (28), which were converted into the crystalline 5'-phosphates (24) and (29), and hence to the dilithium salts of the 5'-pyrophosphates, (25) and (30), by standard procedures.These were labelled at C-5 by bromination, followed by catalytic reduction in tritium gas.The same methyl furanoside starting materials were converted into the 3,5-dibenzoates, (3) and (9), by deacetalation followed by monobenzoylation by the stannylene procedure.Substitution of iodine via the 2-trifluoromethanesulphonates gave iodides which were reduced by tributylstannane to methyl 3,5-di-O-benzoyl-2,6-dideoxy-β-D-ribo- and α-L-lyxo-hexofuranosides (7) ang (13).Coupling of these in the same way as above, followed by alkaline methanolysis, gave the two deoxycytidine homologues, 1-(2,6-dideoxy-β-D-ribo- and -α-L-lyxo-hexofuranosyl)cytosine, (16) and (17), together with their anomers (14) and (15).In another approach to these nucleosides, 4-N-acetyl-2',3'-O-isopropylidenecytidine was oxidized to the aldehyde (33) which was condensed with dimethylsulphoxonium methylide to a mixture of epoxides (34) and (35).Hydrogen bromide opening , followed by tributylstannane reduction, converted these epoxides into 4-N-acetyl-1-(2,3-O-isopropylidene-6-deoxy-β-D-allo- and -α-L-talo-furanosyl)-2H-pyrimidine (39), the first reported anhydro-nucleoside with two oxygen bridges between the base and the sugar, available in 18percent overall yield from protected cytidine.
- David, Serge,Sennyey, Gerard de
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p. 385 - 394
(2007/10/02)
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- CHRYSOERIOL 7-(2''-O-β-D-ALLOPYRANOSYL)-β-D-GLUCOPYRANOSIDE FROM SIDERITIS GRANDIFLORA
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The aerial parts of Sideritis grandiflora yielded a new flavone glycoside, identified as chrysoeriol 7-(2''-allosylglucoside).Key Word Index - Sideritis grandiflora; Labiatae; 13C-NMR; chrysoeriol 7-(2''-O-β-D-allopyranosyl-β-D-glucopyranoside)
- Rabanal, Rosa M.,Valverde, S.,Martin-Lomas, M.,Rodriguez, B.,Chari, V. M.
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p. 1830 - 1832
(2007/10/02)
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- STUDIES ON 3-EPIMERIC 2-HEXULOSE PHENYLOSAZONES. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-arabino- AND D-ribo-2-HEXULOSE PHENYLOSAZONE
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Dehydration of the 3-epimeric 2-hexulose phenylosazones D-arabino-hexulose phenylosazone or D-ribo-hexulose phenylosazone afforded 3,6-anhydro-D-ribo-hexulose phenylosazone (4) as the preponderant isomer from both.The identity of 4 was obtained by t.l.c., and by acylation followed by comparison of the products.Prolonged acetylation with acetic anhydride-pyridine, or by refluxing with acetic anhydride, afforded the same N-acetyldi-O-acetyl derivative.Refluxing 4 with copper sulfate, or the osotriazole with 20percent methanolic sulfuric acid, afforded the C-nucleoside analog, namely, 4-β-D-erythrofuranosyl-2-phenyl-1,2,3-osotriazole (7).The anomeric configurations of 4 and 7 were ascertained from the n.m.r. spectra of their isopropylidene derivatives.The mechanism of the dehydrative cyclization process and the mass spectra of two compounds were discussed.
- Sallam, Mohammed A. E.,Hegazy, Estrwah I. A.
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p. 177 - 188
(2007/10/02)
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- STRUCTURE D'UN NOUVEL HETEROSIDE D'ISOFLAVONE : LE SAROTHAMNOSIDE
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The structure of sarothamnoside (genistein 7,4'-di-O-4-O-β-D-glucopyranosyl-β-D-apiofuranoside), a new isoflavone glycoside from Sarothamnus scoparius and S. patens, has been established by spectral analysis, mainly 13C NMR.
- Brum-Bousquet, M.,Lallemand, Y.,Tillequin, F.,Delaveau, P.
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p. 1223 - 1226
(2007/10/02)
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- The "formoin reaction" : A promising entry to carbohydrates from formaldehyde
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Formaldehyde condensation catalyzed by the conjugate bases of thiazolium ions, leads to a complex mixture ("formoin mixture") of unbranched aldoses and ketoses, in which glucose, galactose, glyceraldehyde dimer, xylose and arabinose have been identified.
- Castells, Joseph,Geijo, Fernando,Lopez-Calahorra, Francisco
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p. 4517 - 4520
(2007/10/02)
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