Relevant bibliographies by topics / Glycosides

Academic literature on the topic 'Glycosides'

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Published: 4 June 2021
Last updated: 29 July 2024

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Journal articles on the topic "Glycosides"

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Ati, Jihen, Pierre Lafite, and Richard Daniellou. "Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides." Beilstein Journal of Organic Chemistry 13 (September 5, 2017): 1857–65. http://dx.doi.org/10.3762/bjoc.13.180.

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Carbohydrate related enzymes, like glycosyltransferases and glycoside hydrolases, are nowadays more easily accessible and are thought to represent powerful and greener alternatives to conventional chemical glycosylation procedures. The knowledge of their corresponding mechanisms has already allowed the development of efficient biocatalysed syntheses of complex O-glycosides. These enzymes can also now be applied to the formation of rare or unnatural glycosidic linkages.
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Kim, Young Soo, and Jin Yeul Ma. "Insight into the Hydrolytic Selectivity of β-Glucosidase to Enhance the Contents of Desired Active Phytochemicals in Medicinal Plants." BioMed Research International 2018 (December 27, 2018): 1–10. http://dx.doi.org/10.1155/2018/4360252.

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Most glycosides in herbal medicines become pharmacologically active after hydrolysis or subsequent metabolism to respective aglycones. Hence, the hydrolytic efficiency of glycosidase is a crucial determinant of the pharmacological efficacy of herbal glycosides. In this study, we investigated the enzymatic conversion of the four herbal extracts and their glycosides using the glycoside hydrolase family 3 β-glucosidase from Lactobacillus antri (rBGLa). We show that β-glucosidase substrate specificity depends on the arrangements and linkage types of sugar residues in glycosides. The enzyme rBGLa showed higher hydrolytic selectivity for glucopyranoside than for glucuronide and rhamnopyranoside, and specificity for 1→6 rather than 1→2 linkages. In addition, in silico 3D structural models suggested that D243 and E426 of rBGLa act as catalytic nucleophile and acid/base residues, respectively. These experiments also suggested that substrate specificity is determined by interactions between the C6 residue of the sugar moiety of the substrate glycoside and the oxygen OD1 of D56 in rBGLa. Therefore, despite the broad substrate spectrum of β-glucosidase, differences in hydrolytic selectivity of β-glucosidases for glycoside structures could be exploited to enhance the hydrolysis of the desired medicinal glycosides in herbs using tailored β-glucosidases, allowing for improvement of specific potencies of herbal medicines.
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Perez-Rizquez, Carlos, David Lopez-Tejedor, Laura Plaza-Vinuesa, Blanca de las Rivas, Rosario Muñoz, Jose Cumella, and Jose M. Palomo. "Chemical Modification of Novel Glycosidases from Lactobacillus plantarum Using Hyaluronic Acid: Effects on High Specificity against 6-Phosphate Glucopyranoside." Coatings 9, no. 5 (May 9, 2019): 311. http://dx.doi.org/10.3390/coatings9050311.

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Three novel glycosidases produced from Lactobacillus plantarum, so called Lp_0440, Lp_2777, and Lp_3525, were isolated and overexpressed on Escherichia coli containing a His-tag for specific purification. Their specific activity was evaluated against the hydrolysis of p-nitrophenylglycosides and p-nitrophenyl-6-phosphate glycosides (glucose and galactose) at pH 7. All three were modified with hyaluronic acid (HA) following two strategies: A simple coating by direct incubation at alkaline pH or direct chemical modification at pH 6.8 through preactivation of HA with carbodiimide (EDC) and N-hydroxysuccinimide (NHS) at pH 4.8. The modifications exhibited important effect on enzyme activity and specificity against different glycopyranosides in the three cases. Physical modification showed a radical decrease in specific activity on all glycosidases, without any significant change in enzyme specificity toward monosaccharide (glucose or galactose) or glycoside (C-6 position free or phosphorylated). However, the surface covalent modification of the enzymes showed very interesting results. The glycosidase Lp_0440 showed low glycoside specificity at 25 °C, showing the same activity against p-nitrophenyl-glucopyranoside (pNP-Glu) or p-nitrophenyl-6-phosphate glucopyranoside (pNP-6P-Glu). However, the conjugated cHA-Lp_0440 showed a clear increase in the specificity towards the pNP-Glu and no activity against pNP-6P-Glu. The other two glycosidases (Lp_2777 and Lp_3525) showed high specificity towards pNP-6P-glycosides, especially to the glucose derivative. The HA covalent modification of Lp_3525 (cHA-Lp_3525) generated an enzyme completely specific against the pNP-6P-Glu (phosphoglycosidase) maintaining more than 80% of the activity after chemical modification. When the temperature was increased, an alteration of selectivity was observed. Lp_0440 and cHA-Lp_0440 only showed activity against p-nitrophenyl-galactopyranoside (pNP-Gal) at 40 °C, higher than at 25 °C in the case of the conjugated enzyme.
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Ortiz-Ramírez, Jorge A., Mayra Cuéllar-Cruz, Julio C. Villagómez-Castro, and Everardo López-Romero. "Fungal Glycosidases in Sporothrix Species and Candida albicans." Journal of Fungi 9, no. 9 (September 12, 2023): 919. http://dx.doi.org/10.3390/jof9090919.

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Glycoside hydrolases (GHs) are enzymes that participate in many biological processes of fungi and other organisms by hydrolyzing glycosidic linkages in glycosides. They play fundamental roles in the degradation of carbohydrates and the assembly of glycoproteins and are important subjects of studies in molecular biology and biochemistry. Based on amino acid sequence similarities and 3-dimensional structures in the carbohydrate-active enzyme (CAZy), they have been classified in 171 families. Members of some of these families also exhibit the activity of trans-glycosydase or glycosyl transferase (GT), i.e., they create a new glycosidic bond in a substrate instead of breaking it. Fungal glycosidases are important for virulence by aiding tissue adhesion and colonization, nutrition, immune evasion, biofilm formation, toxin release, and antibiotic resistance. Here, we review fungal glycosidases with a particular emphasis on Sporothrix species and C. albicans, two well-recognized human pathogens. Covered issues include a brief account of Sporothrix, sporotrichosis, the different types of glycosidases, their substrates, and mechanism of action, recent advances in their identification and characterization, their potential biotechnological applications, and the limitations and challenges of their study given the rather poor available information.
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Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides." Pure and Applied Chemistry 91, no. 9 (September 25, 2019): 1451–70. http://dx.doi.org/10.1515/pac-2019-0306.

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Abstract Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups.
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Slámová, Kristýna, Jana Kapešová, and Kateřina Valentová. "“Sweet Flavonoids”: Glycosidase-Catalyzed Modifications." International Journal of Molecular Sciences 19, no. 7 (July 21, 2018): 2126. http://dx.doi.org/10.3390/ijms19072126.

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Natural flavonoids, especially in their glycosylated forms, are the most abundant phenolic compounds found in plants, fruit, and vegetables. They exhibit a large variety of beneficial physiological effects, which makes them generally interesting in a broad spectrum of scientific areas. In this review, we focus on recent advances in the modifications of the glycosidic parts of various flavonoids employing glycosidases, covering both selective trimming of the sugar moieties and glycosylation of flavonoid aglycones by natural and mutant glycosidases. Glycosylation of flavonoids strongly enhances their water solubility and thus increases their bioavailability. Antioxidant and most biological activities are usually less pronounced in glycosides, but some specific bioactivities are enhanced. The presence of l-rhamnose (6-deoxy-α-l-mannopyranose) in rhamnosides, rutinosides (rutin, hesperidin) and neohesperidosides (naringin) plays an important role in properties of flavonoid glycosides, which can be considered as “pro-drugs”. The natural hydrolytic activity of glycosidases is widely employed in biotechnological deglycosylation processes producing respective aglycones or partially deglycosylated flavonoids. Moreover, deglycosylation is quite commonly used in the food industry aiming at the improvement of sensoric properties of beverages such as debittering of citrus juices or enhancement of wine aromas. Therefore, natural and mutant glycosidases are excellent tools for modifications of flavonoid glycosides.
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Muradova, Mariam, Alena Proskura, Francis Canon, Irina Aleksandrova, Mathieu Schwartz, Jean-Marie Heydel, Denis Baranenko, Liudmila Nadtochii, and Fabrice Neiers. "Unlocking Flavor Potential Using Microbial β-Glucosidases in Food Processing." Foods 12, no. 24 (December 14, 2023): 4484. http://dx.doi.org/10.3390/foods12244484.

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Aroma is among of the most important criteria that indicate the quality of food and beverage products. Aroma compounds can be found as free molecules or glycosides. Notably, a significant portion of aroma precursors accumulates in numerous food products as nonvolatile and flavorless glycoconjugates, termed glycosidic aroma precursors. When subjected to enzymatic hydrolysis, these seemingly inert, nonvolatile glycosides undergo transformation into fragrant volatiles or volatiles that can generate odor-active compounds during food processing. In this context, microbial β-glucosidases play a pivotal role in enhancing or compromising the development of flavors during food and beverage processing. β-glucosidases derived from bacteria and yeast can be utilized to modulate the concentration of particular aroma and taste compounds, such as bitterness, which can be decreased through hydrolysis by glycosidases. Furthermore, oral microbiota can influence flavor perception by releasing volatile compounds that can enhance or alter the perception of food products. In this review, considering the glycosidic flavor precursors present in diverse food and beverage products, we underscore the significance of glycosidases with various origins. Subsequently, we delve into emerging insights regarding the release of aroma within the human oral cavity due to the activity of oral microbial glycosidases.
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Weignerová, Lenka, Yukio Suzuki, Zdenka Huňková, Petr Sedmera, Vladimír Havlíček, Radek Marek, and Vladimír Křen. "Pyridoxine as a Substrate for Screening Synthetic Potential of Glycosidases." Collection of Czechoslovak Chemical Communications 64, no. 8 (1999): 1325–34. http://dx.doi.org/10.1135/cccc19991325.

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The reactions of glycosidases with pyridoxine were used for testing their ability to make new glycosidic bonds. Of 35 glycosidases examined, some exhibited regiospecificity towards one primary alcoholic group; glycosylation of phenolic hydroxyl group was not observed. A series of new glycosides of pyridoxine, 2-acetamido-2-deoxy-β-D-glucopyranosides, α-D-manno- pyranosides, and one α-D-galactopyranoside were prepared and completely characterized by MS and NMR.
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Caffrey, Andrew, and Susan E. Ebeler. "The Occurrence of Glycosylated Aroma Precursors in Vitis vinifera Fruit and Humulus lupulus Hop Cones and Their Roles in Wine and Beer Volatile Aroma Production." Foods 10, no. 5 (April 24, 2021): 935. http://dx.doi.org/10.3390/foods10050935.

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Volatile aroma compounds found in grapes and hops may be present as both free volatiles and bound glycosides. Glycosides found in the raw materials are transferred to their respective fermented beverages during production where the odorless compounds may act as a reservoir of free volatiles that may be perceived by the consumer if hydrolyzed. A review of the literature on grape and wine glycosides and the emerging literature for glycosides in hops is presented in order to demonstrate the depth of history in grape glycoside research and may help direct new research on hop glycosides. Focus is brought to the presence of glycosides in the raw materials, the effect that winemaking and brewing have on glycoside levels, and current methods for the analysis of glycosidically linked aroma compounds.
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Rakić, Bojana, and Stephen G. Withers. "Recent Developments in Glycoside Synthesis with Glycosynthases and Thioglycoligases." Australian Journal of Chemistry 62, no. 6 (2009): 510. http://dx.doi.org/10.1071/ch09059.

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Glycosynthases are hydrolytically incompetent engineered glycosidases that catalyze the high-yielding synthesis of glycoconjugates from glycosyl fluoride donor substrates and appropriate acceptors. Glycosynthases from more than 10 glycoside hydrolase families have now been generated, allowing the synthesis of a wide range of oligosaccharides. Recent examples include glycosynthase-mediated syntheses of xylo-oligosaccharides, xyloglucans, glycolipids, and aryl glycosides. Glycosynthases have also now been generated from inverting glycosidases, increasing the range of enzyme scaffolds. Improvement of glycosynthase activity and broadening of specificity has been achieved through directed evolution approaches, and several novel high-throughput screens have been developed to allow this. Finally, metabolically stable glycoside analogues have been generated using another class of mutant glycosidases: thioglycoligases. Recent developments in all these aspects are discussed.
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Dissertations / Theses on the topic "Glycosides"

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Ahn, Young Ock. "A new class of glycosidases specific to disaccharide glycosides." Kyoto University, 2005. http://hdl.handle.net/2433/145447.

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Kyoto University (京都大学)
0048
新制・課程博士
博士(農学)
甲第11237号
農博第1452号
新制||農||901(附属図書館)
学位論文||H17||N3982(農学部図書室)
22846
UT51-2004-U442
京都大学大学院農学研究科応用生命科学専攻
(主査)教授 坂田 完三, 教授 江崎 信芳, 教授 矢崎 一史
学位規則第4条第1項該当
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DONG, DONG XIA-CATHERINE. "Synthese de glycosides d'aryle et de glycosides d'ether d'enol d'interet biologique." Paris 11, 1990. http://www.theses.fr/1990PA112319.

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Les phenyl 2-o-(3-amino-2,3,6-tridesoxy-alpha-l-arabino et alpha-l-ribohexopyranosyl)-beta-d-glucopyranosides sont prepares en tant que modeles representatifs d'un fragment structural commun aux antibiotiques du groupe de la vancomycine (actinoidine, avoparcine, vancomycine). La synthese de ces chaines laterales heterosaccharidiques est basee sur le couplage de derives du beta-d-glucopyranoside de phenyle avec les glycals totalement proteges de la l-acosamine et de la l-ristosamine, ces derniers etant les precurseurs des fragments 3-amino-2,3,6-tridesoxy-, respectivement de configuration l-arabino et l-ribo. La deprotection partielle ou totale de ces disaccharides fournit les molecules-cibles. La synthese de prodrogues d'anthracyclines antitumorales, comme la daunorubicine, a ete entreprise. Elle comprend la synthese de glycosides d'aryle et d'ether d'enol. Une fois verifiee l'absence de cytotoxicite de ces derives, l'hydrolyse enzymatique a ete etudiee de facon a controler si la liberation de la daunorubicine elle-meme se produisait de facon satisfaisante
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Åberg, Per-Mikael. "Synthesis of blood group A and B determinants and studies towards catalytic glycosidations." Lund : Organic Chemistry 2, Lund Institute of Technology, Lund University, 1994. http://books.google.com/books?id=3J1qAAAAMAAJ.

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Fleury, Adeline. "Synthèse de c-glycosides et daminoacides glycosyles trifluoromethyles." Thesis, Cergy-Pontoise, 2011. http://www.theses.fr/2011CERG0509/document.

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L’objectif de nos travaux consiste en la préparation de C-glycosides et d’aminoacides glycosylés trifluorométhylés dans le but d'obtenir des structures biologiquement actives stabilisées. L'intérêt des C-glycosides est lié à leur stabilité autorisant une pharmacocinétique plus appropriée pour un usage thérapeutique. La 1ière partie de mon travail a été de créer une liaison C-C en position anomérique d'un sucre par différentes méthodes d’alkylation, d’alcynylation à l’indium et par la réaction de Réformatsky. Ensuite après avoir fonctionnalisé les C-glycosides synthétisés, une étude tournée vers la synthèse d’aminoacides C-glycosylés par le biais d’alkylations énantiosélectives a été réalisée. Ensuite nous avons étudié la synthèse d’aminoacides glycosylés stabilisés par l’introduction d’un groupement trifluorométhylé en une position stratégique. D’abord nous avons étudié la synthèse d’aminoacides N-glycosylés obtenus par la réaction entre un aminoacide trifluorométhylé et un sucre. Le groupe fluoré, en  de l’azote, diminue la basicité de l’amine et empêche sa protonation. Ainsi, l’hydrolyse du lien anomérique est très défavorisée. Plusieurs conditions réactionnelles ont été étudiées. Le milieu acide protonique a montré des résultats encourageant notamment entre le 2-déoxy-glucose et un dipeptide trifluorométhylé. Ensuite nous avons travaillé sur la synthèse de O-glycosides. 2 stratégies ont été développé à partir d’un sucre trifluorométhylé. D’abord l’éthérification de Williamson a été étudié entre un sucre trifluorométhylé et différents dérivés halogénés. Cette voie a donné des résultats satisfaisant avec des dérivés halogénés linéaires uniquements. Puis la réaction de Mitsunobu a été étudié entre un sucre trifluorométhylé et différents alcools. La réaction donne des résultats variés dépendant de l’alcool. Cette voie nous a aussi permis de synthétiser des aminoacides O-glycosylés trifluorométhylé en utilisant la sérine comme alcool
The aim of our work consists in the preparation of C-glycosides and trifluorinated glycosylated aminoacids in order to obtain biogically active structures. The interest of such C-glycosides, is due to its stability. It allows a better pharmacokinetics to a therapeutic use. The first part of my work was to create a C-C bond at the anomeric position of a carbohydrate by different methods such as alkylation, alcynylation and Reformatsky reaction. Then, after functionalized these C-glycosides, a study on C-glycosylated aminoacids synthetized by an enantioselectiv alkylation way was made. The second part of my work was to synthesized stabilized glycoaminoacidsby the introduction of a trifluoromethylated group at a strategic position: at the anomeric position of the carbohydtare or at  position of the anomeric position of the carbohydtare. We first studied the synthesis of N-glycosides with a trifluoromethylated group at  position of the anomeric position of the carbohydtare. This strategy is based on the reaction of a protected sugar with a trifluoromethylated amine catalysed by an acid. Then we studied the synthesis of O-glycoaminoacids with a trifluoromethylated group at the anomeric position of the carbohydtare. Two strategies have been developed. The first one is the alkylation of Williamson. The second one is the reaction of Mitsunobu
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Korkashvili, Tamar. "Steroidal Glycosides of Cordyline australis." The University of Waikato, 2006. http://hdl.handle.net/10289/2237.

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The n-butanol extract of aerial parts of Cordyline australis demonstrated antifungal activity. n-Butanol and chloroform extracts of dried or fresh leaves of C. australis afforded a steroidal glycoside, which was identified as 5α-spirost-25(27)-en-3β-ol 3-O{O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside}, saponin 1. This spirostanol glycoside showed strong antifungal activity towards Trichophyton mentagrophytes and some aspecific activity and cytotoxicity against MRC5 cell. The chloroform extract of fresh leaves of C. australis yielded a second new spirostanol glycoside which was identified as 5α-spirost-25(27)-ene-1β,3β-diol 1-{O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside}, saponin 2. The n-butanol extracts of senescent leaves of C. australis afforded a third new spirostanol glycoside that was identified as 5α-spirost-25(27)-ene-1β,3β-diol 1-{O-β-D- fucopyranoside, saponin 3. A mixture of two isomeric flavonoid glycosides was isolated from dried leaves of C. australis and shown to be a ca 1:1 mixture of isorhamnetin-3-O-{O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside}, 4 and isorhamnetin-3-O-{O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside}, 5. Three other known steroidal glycosides, β-sitosterol glucoside, 6, prosapogenin A of dioscin, 7, and trillin, 8 were also isolated from the leaves of C. australis. The n-butanol extract of dried stems of C. australis afforded (25S)-5α-spirostane-1β,3α-diol 1-{O-β-D-glucopyranoside}, 9. This spirostanol glycoside showed moderate cytotoxicity against Herpes simplex type I virus (ATCC VR733) and Polio Virus Type I (Pfiser vaccine strain).
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Ibrahim, Jamal. "Hydroxylysine glycosides of corneal collagen." Thesis, University of Oxford, 1986. http://ora.ox.ac.uk/objects/uuid:2442f75c-6a1c-4575-98b0-a4475a3df1f2.

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These findings are discussed with respect to the possible role of hydroxylysine glycosides in limiting collagen fibril diameter. Comparisons of the amino acid sequences around the seven glycoside sites however gave no clues as to what makes some lysyl residues more susceptible to modification than others. The possible reasons for the high extent of lysyl modification in the cornea are also discussed.
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Hindle, Neil. "Amino sugars and their glycosides." Thesis, University of Oxford, 1995. http://ora.ox.ac.uk/objects/uuid:78ab400f-4a4c-47bb-9d18-1b3bef205044.

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This thesis describes approaches to the transformation of simple carbohydrates into a polyhydroxylated pyrrolidine and the formation of its glucosides. Chapter one describes the synthesis of the naturally occurring pyrrolidine 2,5-dideoxy-2,5-imino-D-mannitol. Synthesised from di-O-isopropylidene-D-glucose, the key steps are the introduction of nitrogen at C-5 with retention of configuration. Then cyclisation of the nitrogen onto the C-2 position with inversion to form the pyrrolidine ring. Reduction of the aldehyde furnished the polyhydroxylated heterocycle in 3.4% yield over 16 steps. The synthetic compound matched the naturally occurring compound in all respects. Chapter two contains a review of commonly used glycosylation methods. It also describes the glycosylation of di-O-isopropylidene-α-D-glucose as a model system comparing the Koenig-Knorr method to the trichloroacetimidate method using several reaction conditions. Glycosylation of 2,5-dideoxy-2,5-imino-D-mannitol was carried out using the trichloroacetimidate method to synthese all four glucosides. Boron trifluoride etherate and trimethylsilyl trifluoromethanesulphonate were used as catalysts in dichloromethane, diethyl ether and acetonitrile under strictly anhydrous conditions. All four glucosides were prepared 1-O-(αβ-D-glucopyranosyl)-2,5-dideoxy-2,5-imino-D-mannitol and 3-O-(αβ-D-glucopyranosyl)-2,5-dideoxy-2,5-imino-D-mannitol. Biological screening carried out against a wide range of glycosidases and glycosyl transferases indicated that the glucosides showed little inhibition in comparison to 2,5-dideoxy-2,5-imino-D-mannitol. Chapter three describes the isolation and identification of 1-O-(β-D-glucopyranosyl)- 2,5-dideoxy-2,5-imino-D-mannitol from Nephthytis poisonii N.E.Br. a member of the Araceae family found in tropical Africa. Identification was made by comparison with the previously synthesised glucosides of 2,5-dideoxy-2,5-imino-Dmannitol. Investigations of Hyacinthoides non-scriptus (L.) chouard ex Rothm are also discussed. Chapter four describes the synthesis of a diazidolactone that could be used to form a 1,5 disubstituted tetrazole. This would have a second nitrogen functionality in the molecule allowing the possibility of the inclusion of the tetrazole into a peptide sequence. The synthesis was carried out from L-gulono-1,4-lactone. An azido group was introduced selectively at C-2, this unexpectedly occurred with retention of configuration. A second azide was then introduced at C-5, this occurring with the more commonly observed inversion of configuration to afford the 2,5-diazido-2,5-dideoxy-D-manno-1,4-lactone.
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Lacy, Christopher. "The syntheses of morphine glycosides." Thesis, University of Bath, 1995. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.760686.

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JEGOU, ANNE. "Nouvelles syntheses de c-glycosides." Rennes 1, 1998. http://www.theses.fr/1998REN10128.

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Les c-glycosides sont des analogues de sucres dans lesquels un atome de carbone remplace l'atome d'oxygene anomerique. En tant qu'analogue, un c-glycoside, de surcroit stable a l'hydrolyse chimique ou enzymatique, peut interferer dans le metabolisme des glucides en inhibant les enzymes (glycosidases ou glycosyltransferases) qui sont necessaires a l'elaboration d'un glycoconjugue fonctionnel. Les acetals bicycliques 2:2:1 derivent du 6-o-pivaloyl-d-galactal via une reaction d'iodocyclisation. Leur ouverture regioselective par des c-nucleophiles nous a permis d'exploiter la geometrie particuliere de ces molecules pour synthetiser stereoselectivement des motifs c-furanosides. L'allyltrimethylsilane et le 2-(trimethylsilyloxy)furane ont ete en particulier utilises. La reactivite du 2-(trimethylsilyloxy)furane, ainsi que celle du 3-trimethylsilylmethyl-but-3-enoate de methyle, derive du dicetene, vis-a-vis de donneurs de glycopyranosyle, ont ete egalement etudiees. Ces deux nucleophiles permettent d'introduire, des l'etape de c-glycosylation, une chaine fonctionnalisee en position anomerique.
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Tan, Jingjun. "Dietary isoflavones : aglycones and glycosides." Thesis, University of Leeds, 2011. http://etheses.whiterose.ac.uk/2092/.

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Flavonoids are non-nutrient secondary metabolites ubiquitous in plants, associated with protection against various diseases, such as cancer and cardiovascular diseases. Dietary flavonoids are normally found as conjugated glycosides except, notably, in fermented foods where although there may be losses in total flavonoid content, levels of liberated aglycones can be relatively high. There has been considerable interest in the relationship between the form and structure of the ingested flavonoids and the consequences for efficiency of absorption. The research focused firstly on β-D-glucosidases (β-D-glycoside glucohydrolase, EC 3.2.1.21) extracted from different plant sources and characterised. The enzyme was found at the highest levels in almond and apple seeds. The optimum reaction conditions of the enzyme from apple seeds were determined to be pH 5.5 at 65ºC, and the enzyme extract was stable at 4ºC for at least 12 weeks. Kinetic characterisation of the enzyme from selected materials was carried out by using para-nitrophenyl-β-D-glucopyranoside (p-NP-Glc) as substrate. The Km and Vmax of the enzyme from apple seed extract were determined, for the first time, to be 5.48 ± 0.34 mM and 15.60 ± 0.95 U/mg protein (n = 8), respectively, with the protein content of the extract being 0.728 ± 0.019 mg/ml. Secondly, isoflavone contents from different sources were investigated. Soy bean and its products are were found to be good sources of daidzin and genistin; kudzu was the best source of puerarin; red clover and chickpea were good sources of formononetin and biochanin A. Passion fruit was found to be an interesting source of isoflavones outside the legume family. By using selected enzyme sources and isoflavone sources, a novel natural style soy-based food was developed in which isoflavones existed predominately as aglycones. The food, derived using soya and enzymes from waste sources, may have further potential.
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Books on the topic "Glycosides"

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Levy, D. E. The chemistry of C-glycosides. Oxford, OX, U.K: Pergamon, 1995.

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Wölwer-Rieck, Ursula, ed. Steviol Glycosides. Cambridge: Royal Society of Chemistry, 2018. http://dx.doi.org/10.1039/9781788010559.

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1936-, Smith Thomas Woodward, ed. Digitalis glycosides. Orlando: Grune & Stratton, 1986.

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1927-, Ikan Raphael, ed. Naturally occurring glycosides. Chichester: John Wiley, 1999.

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Erdmann, Erland, K. Greef, and J. C. Skou, eds. Cardiac Glycosides 1785–1985. Heidelberg: Steinkopff, 1986. http://dx.doi.org/10.1007/978-3-662-11292-2.

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Yukihiro, Shoyama, ed. Analysis of natural glycosides. Trivandrum: Research Signpost, 2007.

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E, Stütz Arnold, ed. Iminosugars as glycosidase inhibitors: Nojirimycin and beyond. Weinheim: Wiley-VCH, 1999.

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Brito-Arias, Marco. Synthesis and Characterization of Glycosides. Cham: Springer International Publishing, 2022. http://dx.doi.org/10.1007/978-3-030-97854-9.

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Brito-Arias, Marco. Synthesis and Characterization of Glycosides. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-32310-7.

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Isles, Stephen John. Vinyl glycosides in oligosaccharide synthesis. Birmingham: University of Birmingham, 1996.

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Book chapters on the topic "Glycosides"

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Takahashi, Daisuke, and Kazunobu Toshima. "Complex Oligosaccharides Synthesis—Challenges and Tactics." In Modern Natural Product Synthesis, 299–318. Singapore: Springer Nature Singapore, 2024. http://dx.doi.org/10.1007/978-981-97-1619-7_14.

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Abstract1,2-cis glycoside structures exist as constituents of biologically active natural products, pharmaceuticals, and functional materials. Therefore, there is a pressing need for the development of novel and efficient 1,2-cis-glycosylation methods to understand their specific roles and to create new lead compounds for pharmaceutical and functional materials by derivatization of these glycosides. In this context, we have developed a conceptually new glycosylation method called boron-mediated aglycon delivery (BMAD), which utilizes organoboron catalysis for simultaneously controlling the 1,2-cis stereoselectivity of the glycosidic bond formed and regioselectivity of the reaction site in the glycosyl acceptor. The method has been applied to synthesize useful glycosides including complex oligosaccharides found in pathogenic bacteria. We recently extended the BMAD method to the reaction of partially protected and unprotected glycosides for the late-stage modification of natural glycosides with interesting biological activities, and synthesized complex oligosaccharides using minimal protecting groups. Furthermore, we developed a diastereoselective desymmetric BMAD reaction of meso-diols as a new synthetic tactic for complex glycosides. Herein, we discuss the abovementioned BMAD methods and their use in the synthesis of useful glycosides.
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Ribeiro, Maria Henriques L. "Glycosides." In Biotechnology of Bioactive Compounds, 301–44. Chichester, UK: John Wiley & Sons, Ltd, 2015. http://dx.doi.org/10.1002/9781118733103.ch13.

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Pengelly, Andrew. "Glycosides." In The constituents of medicinal plants, 59–72. 3rd ed. Wallingford: CABI, 2021. http://dx.doi.org/10.1079/9781789243079.0004.

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Abstract Glycosides are a group of compounds consisting of a sugar portion (or moiety) attached by a special bond to one or more non-sugar portions. Chemically, they are hydroxyls of a sugar capable of forming ethers with other alcohols, or esters with acids. This chapter provides information on glycosides, including their distribution throughout the plant kingdom, medicinal properties, and toxicity.
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Deepak, D., S. Srivastav, and A. Khare. "Pregnane Glycosides." In Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, 169–325. Vienna: Springer Vienna, 1997. http://dx.doi.org/10.1007/978-3-7091-6529-4_3.

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Deepak, D., S. Srivastava, N. K. Khare, and A. Khare. "Cardiac Glycosides." In Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, 71–155. Vienna: Springer Vienna, 1996. http://dx.doi.org/10.1007/978-3-7091-6578-2_2.

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Mégarbane, Bruno. "Digitalis Glycosides." In Critical Care Toxicology, 1–14. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-20790-2_185-1.

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Kelly, Ralph A., and Thomas W. Smith. "Digitalis Glycosides." In Congestive Heart Failure, 354–79. New York, NY: Springer New York, 1994. http://dx.doi.org/10.1007/978-1-4613-8315-4_22.

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Mégarbane, Bruno. "Digitalis Glycosides." In Critical Care Toxicology, 807–19. Cham: Springer International Publishing, 2017. http://dx.doi.org/10.1007/978-3-319-17900-1_185.

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Banik, Bimal Krishna, Biswa Mohan Sahoo, and Abhishek Tiwari. "Terpene Glycosides." In Terpenoids, 229–53. Boca Raton: CRC Press, 2022. http://dx.doi.org/10.1201/9781003008682-7.

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Liu, Dongyou. "Cyanogenic Glycosides." In Handbook of Foodborne Diseases, 1081–87. Boca Raton : Taylor & Francis, [2019] | Series: Food microbiology series | “A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc.”: CRC Press, 2018. http://dx.doi.org/10.1201/b22030-101.

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Conference papers on the topic "Glycosides"

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Mazeyka, A. N., N. M. Sanina, L. A. Pomazenkova, and E. A. Barsova. "METHOD FOR PREPARATION THE SUM OF TRITERPENE GLYCOSIDES - IMPORTANT BIOLOGICALL ACTIVE COMPOUNS FROM THE FAR EASTERN EDIBLE HOLOTHURIA - Apostichopus japonicas." In I International Congress “The Latest Achievements of Medicine, Healthcare, and Health-Saving Technologies”. Kemerovo State University, 2023. http://dx.doi.org/10.21603/-i-ic-78.

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Description of a method for preparation the sum of triterpene glycosides of the Far Eastern edible holothuria - Apostichopus japonicus is given. The method utilize a food production waste as a feedstock. The method includes a description of the procedures of procurement and storage of feedstock, extraction and purification of triterpene glycosides. The characteristic of the resulting is given.
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Couto, Túlio R., Juliano C. R. Freitas, João R. Freitas Filho, Silvia R. C. P. Andrade, Ivani Malvestiti, and Paulo H. Menezes. "Synthesis of O-Glycosides 1,3-Diynes." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0218-1.

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Pertuit, D., AC Mitaine-Offer, T. Miyamoto, C. Tanaka, C. Delaude, and MA Lacaille-Dubois. "New terpenoid glycosides from Eriocoelum microspermum." In GA 2017 – Book of Abstracts. Georg Thieme Verlag KG, 2017. http://dx.doi.org/10.1055/s-0037-1608240.

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Rodríguez-Ramírez, Juan, Beatriz Noyola-Altamirano, Luis Gerardo Barriada-Bernal, and Lilia L. Méndez-Lagunas. "Effects of drying conditions on the content of glycosides and antioxidants of packed bed of stevia leaves." In 21st International Drying Symposium. Valencia: Universitat Politècnica València, 2018. http://dx.doi.org/10.4995/ids2018.2018.7519.

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The commercial value of stevia dehydrated leaves is related to the content of glycocides and their appearance. The present work approaches the effect of packed bed drying conditions (temperature, flow rate and solid loading) on glycosides and antioxidants activity of stevia leaves of Morita II variety. Diffusion coefficient was calculated. The drying times ranged between 34 and 160 minutes, the temperature was the most significant factor followed by solid loading and flow rate. Drying increases the concentration of antioxidants, stevioside and reduces rebaudioside A. Keywords: drying, packed bed, stevia rebaudiana, glycosides, antioxidants
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Sprenger, Friedrich K. (Fitz), Frederik Diness, Inge Lundt, and Arnold E. Stutz. "C-GLYCOSIDES OF 4-AMINO-4-DEOXY-D-ARABINOFURANOSE: PRECURSORS EN ROUTE TO GLYCOSIDASE INHIBITING BROUSSONETINES." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.638.

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MOROTTI, A. L. M., L. A. ZIMMERMANN, V. R. MACHADO, E. P. SCHENKEL, and L. S. C. BERNARDES. "Selective semi-synthesis of dihydrocucurbitacin B glycosides." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013101412589.

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Svistova, I. D., and N. M. Kuvshinova. "Phytosanitary effect of the plants – producers of sweet glycosides." In 2nd International Scientific Conference "Plants and Microbes: the Future of Biotechnology". PLAMIC2020 Organizing committee, 2020. http://dx.doi.org/10.28983/plamic2020.241.

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In the root zone of plants that accumulate sweet glycosides (honey stevia and naked licorice), a sharp decrease in the phytopathogenic potential of the soil was revealed without increasing its phytotoxic activity.
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Freitas, Juliano C. R., Wagner C. C. dos Santos, Bruna L. da Silva, Paulo H. Menezes, and Roberta A. Oliveira. "Stereoselective Synthesis of C-Glycosides using Potassium Aryltrifluoroborates." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0220-1.

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Riemann, Ingo, and Wolf-Dieter Fessner. "C-GLYCOSIDES FROM UNPROTECTED SUGARS (1) MECHANISTIC STUDIES." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.632.

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Iskandarova, S. F., and N. A. Dzhabbarov. "QUANTITATIVE ANALYZING TRITERPENE GLYCOSIDES IN SOPHORA JAPONICA DRY EXTRACT." In VI International Youth Conference "Perspectives of Science and Education". Prague: Premier Publishing s.r.o., 2019. http://dx.doi.org/10.29013/vi-conf-usa-6-17-18.

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Reports on the topic "Glycosides"

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Tian, Huichuan, Jiajun Ren, and Meilan Zhang. Alprostadil Combined with Tripterygium Glycosides in the Treatment of Diabetic nephropathy：A Systematic Review and Meta-analysis. INPLASY - International Platform of Registered Systematic Review and Meta-analysis Protocols, August 2020. http://dx.doi.org/10.37766/inplasy2020.8.0063.

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Li, Zifeng, Xiaolan Fu, Long Yin, Xiaoqiang Hou, and Caiyun Chang. Clinical effect of Tripterygium Glycosides in the treatment of connective tissue disease-related interstitial lung disease：Meta analysis. INPLASY - International Platform of Registered Systematic Review and Meta-analysis Protocols, August 2021. http://dx.doi.org/10.37766/inplasy2021.8.0028.

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He, Mingyu, Tianying Chang, and Shoulin Zhang. Efficacy and safety of Tripterygium wilfordii glycosides in treatment of IgA nephropathy：A systematic review and meta-analysis. INPLASY - International Platform of Registered Systematic Review and Meta-analysis Protocols, January 2022. http://dx.doi.org/10.37766/inplasy2022.1.0037.

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Shi, Hongshuo, Pin Deng, Lei Wang, Wenbin Liu, Yinghao Li, Chengda Dong, Yanfang Wang, Guomin Si, and Tiantian Yang. The Efficacy and Safety of Tripterygium Glycosides for Diabetic Kidney Disease: An Overview of Systematic Reviews and Meta-Analyses. INPLASY - International Platform of Registered Systematic Review and Meta-analysis Protocols, March 2022. http://dx.doi.org/10.37766/inplasy2022.3.0065.

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Koch, Lisa M., Casey Crooks, and Franz St. John. Development of a high-performance gel filtration chromatography polysaccharide sizing method to facilitate glycoside hydrolase functional analysis. Madison, WI: U.S. Department of Agriculture, Forest Service, Forest Products Laboratory, 2024. http://dx.doi.org/10.2737/fpl-rn-427.

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Brenchly, Jean E. The Characterization of Psychrophilic Microorganisms and their potentially useful Cold-Active Glycosidases Final Progress Report. Office of Scientific and Technical Information (OSTI), June 2008. http://dx.doi.org/10.2172/959114.

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Davis, M. NREL Support for a Functional Genomics Approach to Investigate Regulation of Phenolic Glycoside: Cooperative Research and Development Final Report, CRADA number CRD-07-00218. Office of Scientific and Technical Information (OSTI), July 2010. http://dx.doi.org/10.2172/985572.

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Borch, Thomas, Yitzhak Hadar, and Tamara Polubesova. Environmental fate of antiepileptic drugs and their metabolites: Biodegradation, complexation, and photodegradation. United States Department of Agriculture, January 2012. http://dx.doi.org/10.32747/2012.7597927.bard.

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Many pharmaceutical compounds are active at very low doses, and a portion of them regularly enters municipal sewage systems and wastewater-treatment plants following use, where they often do not fully degrade. Two such compounds, CBZ and LTG, have been detected in wastewater effluents, surface waters, drinking water, and irrigation water, where they pose a risk to the environment and the food supply. These compounds are expected to interact with organic matter in the environment, but little is known about the effect of such interactions on their environmental fate and transport. The original objectives of our research, as defined in the approved proposal, were to: Determine the rates, mechanisms and products of photodegradation of LTG, CBZ and selected metabolites in waters exposed to near UV light, and the influence of DOM type and binding processes on photodegradation. Determine the potential and pathways for biodegradation of LTG, CBZ and selected metabolites using a white rot fungus (Pleurotusostreatus) and ADP, and reveal the effect of DOM complexation on these processes. Reveal the major mechanisms of binding of LTG, CBZ and selected metabolites to DOM and soil in the presence of DOM, and evaluate the effect of this binding on their photodegradation and/or biodegradation. We determined that LTG undergoes relatively slow photodegradation when exposed to UV light, and that pH affects each of LTG’s ability to absorb UV light, the efficiency of the resulting reaction, and the identities of LTG’sphotoproducts (t½ = 230 to 500 h during summer at latitude 40 °N). We observed that LTG’sphotodegradation is enhanced in the presence of DOM, and hypothesized that LTG undergoes direct reactions with DOM components through nucleophilic substitution reactions. In combination, these data suggest that LTG’s fate and transport in surface waters are controlled by environmental conditions that vary with time and location, potentially affecting the environment and irrigation waters. We determined that P. ostreatusgrows faster in a rich liquid medium (glucose peptone) than on a natural lignocellulosic substrate (cotton stalks) under SSF conditions, but that the overall CBZ removal rate was similar in both media. Different and more varied transformation products formed in the solid state culture, and we hypothesized that CBZ degradation would proceed further when P. ostreatusand the ᵉⁿᶻʸᵐᵃᵗⁱᶜ ᵖʳᵒᶠⁱˡᵉ ʷᵉʳᵉ ᵗᵘⁿᵉᵈ ᵗᵒ ˡⁱᵍⁿⁱⁿ ᵈᵉᵍʳᵃᵈᵃᵗⁱᵒⁿ. ᵂᵉ ᵒᵇˢᵉʳᵛᵉᵈ ¹⁴C⁻Cᴼ2 ʳᵉˡᵉᵃˢᵉ ʷʰᵉⁿ ¹⁴C⁻ᶜᵃʳᵇᵒⁿʸˡ⁻ labeled CBZ was used as the substrate in the solid state culture (17.4% of the initial radioactivity after 63 days of incubation), but could not conclude that mineralization had occurred. In comparison, we determined that LTG does not degrade in agricultural soils irrigated with treated wastewater, but that P. ostreatusremoves up to 70% of LTG in a glucose peptone medium. We detected various metabolites, including N-oxides and glycosides, but are still working to determine the degradation pathway. In combination, these data suggest that P. ostreatuscould be an innovative and effective tool for CBZ and LTG remediation in the environment and in wastewater used for irrigation. In batch experiments, we determined that the sorption of LTG, CBZ and selected metabolites to agricultural soils was governed mainly by SOM levels. In lysimeter experiments, we also observed LTG and CBZ accumulation in top soil layers enriched with organic matter. However, we detected CBZ and one of its metabolites in rain-fed wheat previously irrigated with treated wastewater, suggesting that their sorption was reversible, and indicating the potential for plant uptake and leaching. Finally, we used macroscale analyses (including adsorption/desorption trials and resin-based separations) with molecular- level characterization by FT-ICR MS to demonstrate the adsorptive fractionation of DOM from composted biosolids by mineral soil. This suggests that changes in soil and organic matter types will influence the extent of LTG and CBZ sorption to agricultural soils, as well as the potential for plant uptake and leaching.
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Morrison, Mark, Joshuah Miron, Edward A. Bayer, and Raphael Lamed. Molecular Analysis of Cellulosome Organization in Ruminococcus Albus and Fibrobacter Intestinalis for Optimization of Fiber Digestibility in Ruminants. United States Department of Agriculture, March 2004. http://dx.doi.org/10.32747/2004.7586475.bard.

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Improving plant cell wall (fiber) degradation remains one of the highest priority research goals for all ruminant enterprises dependent on forages, hay, silage, or other fibrous byproducts as energy sources, because it governs the provision of energy-yielding nutrients to the host animal. Although the predominant species of microbes responsible for ruminal fiber degradation are culturable, the enzymology and genetics underpinning the process are poorly defined. In that context, there were two broad objectives for this proposal. The first objective was to identify the key cellulosomal components in Ruminococcus albus and to characterize their structural features as well as regulation of their expression, in response to polysaccharides and (or) P AA/PPA. The second objective was to evaluate the similarities in the structure and architecture of cellulosomal components between R. albus and other ruminal and non-ruminal cellulolytic bacteria. The cooperation among the investigators resulted in the identification of two glycoside hydrolases rate-limiting to cellulose degradation by Ruminococcus albus (Cel48A and CeI9B) and our demonstration that these enzymes possess a novel modular architecture specific to this bacterium (Devillard et al. 2004). We have now shown that the novel X-domains in Cel48A and Cel9B represent a new type of carbohydrate binding module, and the enzymes are not part of a ceiluiosome-like complex (CBM37, Xu et al. 2004). Both Cel48A and Cel9B are conditionally expressed in response to P AA/PPA, explaining why cellulose degradation in this bacterium is affected by the availability of these compounds, but additional studies have shown for the first time that neither PAA nor PPA influence xylan degradation by R. albus (Reveneau et al. 2003). Additionally, the R. albus genome sequencing project, led by the PI. Morrison, has supported our identification of many dockerin containing proteins. However, the identification of gene(s) encoding a scaffoldin has been more elusive, and recombinant proteins encoding candidate cohesin modules are now being used in Israel to verify the existence of dockerin-cohesin interactions and cellulosome production by R. albus. The Israeli partners have also conducted virtually all of the studies specific to the second Objective of the proposal. Comparative blotting studies have been conducted using specific antibodies prepare against purified recombinant cohesins and X-domains, derived from cellulosomal scaffoldins of R. flavefaciens 17, a Clostridium thermocellum mutant-preabsorbed antibody preparation, or against CbpC (fimbrial protein) of R. albus 8. The data also suggest that additional cellulolytic bacteria including Fibrobacter succinogenes S85, F. intestinalis DR7 and Butyrivibrio fibrisolvens Dl may also employ cellulosomal modules similar to those of R. flavefaciens 17. Collectively, our work during the grant period has shown that R. albus and other ruminal bacteria employ several novel mechanisms for their adhesion to plant surfaces, and produce both cellulosomal and non-cellulosomal forms of glycoside hydrolases underpinning plant fiber degradation. These improvements in our mechanistic understanding of bacterial adhesion and enzyme regulation now offers the potential to: i) optimize ruminal and hindgut conditions by dietary additives to maximize fiber degradation (e.g. by the addition of select enzymes or PAA/PPA); ii) identify plant-borne influences on adhesion and fiber-degradation, which might be overcome (or improved) by conventional breeding or transgenic plant technologies and; iii) engineer or select microbes with improved adhesion capabilities, cellulosome assembly and fiber degradation. The potential benefits associated with this research proposal are likely to be realized in the medium term (5-10 years).
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