Journal articles: 'Glycosides'

1

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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8

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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10

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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11

Zheng, Yunfeng, Weiping Duan, Jie Sun, Chenguang Zhao, Qizhen Cheng, Cunyu Li, and Guoping Peng. "Structural Identification and Conversion Analysis of Malonyl Isoflavonoid Glycosides in Astragali Radix by HPLC Coupled with ESI-Q TOF/MS." Molecules 24, no. 21 (October 31, 2019): 3929. http://dx.doi.org/10.3390/molecules24213929.

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In this study, four malonyl isoflavonoid glycosides (MIGs), a type of isoflavonoid with poor structural stability, were efficiently isolated and purified from Astragali Radix by a medium pressure ODS C18 column chromatography. The structures of the four compounds were determined on the basis of NMR and literature analysis. Their major diagnostic fragment ions and fragmentation pathways were proposed in ESI/Q-TOF/MS positive mode. Using a target precursor ions scan, a total of 26 isoflavonoid compounds, including eleven malonyl isoflavonoid glycosides coupled with eight related isoflavonoid glycosides and seven aglycones were characterized from the methanolic extract of Astragali Radix. To clarify the relationship of MIGs and the ratio of transformation in Astragali Radix under different extraction conditions, two MIGs (calycosin-7-O-glycoside-6″-O-malonate and formononetin-7-O-glycoside-6″-O-malonate) coupled with related glycosides (calycosin-7-O-glycoside and formononetin-7-O-glycoside) and aglycones (calycosin and formononetin) were detected by a comprehensive HPLC-UV method. Results showed that MIGs could convert into related glycosides under elevated temperature conditions, which was further confirmed by the conversion experiment of MIGs reference compounds. Moreover, the total contents of MIGs and related glycosides displayed no obvious change during the long-duration extraction. These findings indicated that the quality of Astragali Radix could be evaluated efficiently and accurately by using the total content of MIGs and related glycosides as the quality index.

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12

Xie, Liangqin, Zeyuan Deng, Jie Zhang, Huanhuan Dong, Wei Wang, Banghuai Xing, and Xiaoru Liu. "Comparison of Flavonoid O-Glycoside, C-Glycoside and Their Aglycones on Antioxidant Capacity and Metabolism during In Vitro Digestion and In Vivo." Foods 11, no. 6 (March 20, 2022): 882. http://dx.doi.org/10.3390/foods11060882.

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Flavonoids are well known for their extensive health benefits. However, few studies compared the differences between flavonoid O-glycoside and C-glycoside. In this work, flavonoid O-glycoside (isoquercitrin), C-glycoside (orientin), and their aglycones (quercetin and luteolin) were chosen to compare their differences on antioxidant activities and metabolism during in vitro digestion and in vivo. In vitro digestion, the initial antioxidant activity of the two aglycones was very high; however, they both decreased more sharply than their glycosides in the intestinal phase. The glycosidic bond of flavonoid O-glycoside was broken in the gastric and intestinal stage, while the C-glycoside remained unchanged. In vivo, flavonoid O-glycoside in plasma was more elevated than C-glycoside on the antioxidant activity; however, flavonoid C-glycoside in urine was higher than O-glycoside. These results indicate that differences of flavonoid glycosides and their aglycones on antioxidant activity are closely related to their structural characteristics and metabolism in different samples. Aglycones possessed higher activity but unstable structures. On the contrary, the sugar substituents reduced the activity of flavonoids while improving their stability and helping to maintain antioxidant activities after digestion. Especially the C-glycoside was more stable because the stability of the C–C bond is higher than that of the C–O bond, which contributes to the difference between flavonoid O-glycoside and C-glycoside on the absorption and metabolism in vivo. This study provided a new perspective for comparing flavonoid O-glycoside, flavonoid C-glycoside, and their aglycones on their structure–activity relationship and metabolism.

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Ishikura, Nariyuki, Zhi-qing Yang, Kunijiro Yoshitama, and Kazu Kurosawa. "Flavonol Glycosides from Paederia scandens var. mairei." Zeitschrift für Naturforschung C 45, no. 11-12 (December 1, 1990): 1081–84. http://dx.doi.org/10.1515/znc-1990-11-1201.

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Abstract Four kaempferol glycosides and five quercetin glycosides have been isolated from a methanolic extract of Paederia scandens var. mairei leaves and stems, in which in addition four unknown glycosides of kaempferol and quercetin are present in a trace. Nine flavonol glycosides including a new glycoside quercetin 3-O-rutinoside-7-O-xylosylglucoside (paederinin) were identified by PC, HPLC, UV spectral and NMR studies.

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Silchenko, Alexandra S., Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok, Ekaterina A. Martyyas, and Vladimir I. Kalinin. "Triterpene Glycosides from the Sea Cucumber Eupentacta Fraudatrix. Structure and Biological Action of Cucumariosides I1, I3, I4, Three New Minor Disulfated Pentaosides." Natural Product Communications 8, no. 8 (August 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800805.

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Three new minor triterpene glycosides, cucumariosides I1 (1), I3 (2) and I4 (3) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–3 belong to the group of cucumariosides I, having branched pentasaccharide carbohydrate moieties with two sulfate groups and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit that is a characteristic feature of all the glycosides isolated from E. fraudatrix. Glycosides 1 and 2 differ from each other by the side chain structures in the holostane aglycone moieties, while cucumarioside I4 (3) has a 23,24,25,26,27-pentanorlanostane aglycone with an 18(16)-lactone. Cytotoxic activities of glycosides 1–3 against mouse spleen lymphocytes and ascite form of mouse Ehrlich carcinoma cells, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Glycoside 1, having an aglycone side chain with a 24(25)-double bond, possesses moderate activity in all the tests, while glycoside 2, having 23(24)-double bond and 25-hydroxy group in the side chain, and glycoside 3 with an aglycone with an 18(16)-lactone and shortened side chain have either low activity or are non-active.

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Zhang, Ruiqin, Ruiqi Tang, Jiahua Bi, Shanshan Shen, Qin Wu, Qihe Chen, and Yanjun Li. "Efficient Bioconversion of Stevioside and Rebaudioside A to Glucosylated Steviol Glycosides Using an Alkalihalobacillus oshimesis-Derived Cyclodextrin Glucanotransferase." Molecules 28, no. 3 (January 27, 2023): 1245. http://dx.doi.org/10.3390/molecules28031245.

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The enzymatic transglycosylation of steviol glycosides can improve the edulcorant quality of steviol glycosides. Cyclodextrin glucanotransferase (CGTase) is one of the most popular glucanotransferases applied in this reaction. Herein, the CGTase-producing strain Alkalihalobacillus oshimensis CGMCC 23164 was isolated from Stevia planting soil. Using mass spectrometry-based secretome profiling, a high-efficiency CGTase that converted steviol glycosides to glucosylated steviol glycosides was identified and termed CGTase-13. CGTase-13 demonstrated optimal transglycosylation activity with 10 g/L steviol glycoside and 50 g/L soluble starch as substrates at <40 °C. Under the above conditions, the conversion rate of stevioside and rebaudioside A, two main components of steviol glycosides, reached 86.1% and 90.8%, respectively. To the best of our knowledge, this is the highest conversion rate reported to date. Compared with Toruzyme® 3.0 L, the commonly used commercial enzyme blends, glucosylated steviol glycosides produced using CGTase-13 exhibited weaker astringency and unpleasant taste, faster sweetness onset, and stronger sweetness intensity. Thus, CGTase provides a novel option for producing high-quality glucosylated steviol glycoside products and has great potential for industrial applications.

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Shu, Penghua, Huiqing Zhu, Wanrong Liu, Lingxiang Zhang, Junping Li, Mengzhu Yu, Yingying Fei, et al. "Isolation and Characterization of Glycosidic Tyrosinase Inhibitors from Typhonium giganteum Rhizomes." Records of Natural Products 15, no. 5 (May 8, 2021): 380–87. http://dx.doi.org/10.25135/rnp.230.21.02.1965.

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A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (2–3), two cinnamoyl glycosides (4–5), six phenolic glycosides (6–11), one lignan glycoside (12) and four megastigmane glycosides (13–16) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 1–16 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).

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Méndez-Líter, Juan A., Ana Pozo-Rodríguez, Enrique Madruga, María Rubert, Andrés G. Santana, Laura I. de Eugenio, Cristina Sánchez, Ana Martínez, Alicia Prieto, and María Jesús Martínez. "Glycosylation of Epigallocatechin Gallate by Engineered Glycoside Hydrolases from Talaromyces amestolkiae: Potential Antiproliferative and Neuroprotective Effect of These Molecules." Antioxidants 11, no. 7 (July 5, 2022): 1325. http://dx.doi.org/10.3390/antiox11071325.

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Glycoside hydrolases (GHs) are enzymes that hydrolyze glycosidic bonds, but some of them can also catalyze the synthesis of glycosides by transglycosylation. However, the yields of this reaction are generally low since the glycosides formed end up being hydrolyzed by these same enzymes. For this reason, mutagenic variants with null or drastically reduced hydrolytic activity have been developed, thus enhancing their synthetic ability. Two mutagenic variants, a glycosynthase engineered from a β-glucosidase (BGL-1-E521G) and a thioglycoligase from a β-xylosidase (BxTW1-E495A), both from the ascomycete Talaromyces amestolkiae, were used to synthesize three novel epigallocatechin gallate (EGCG) glycosides. EGCG is a phenolic compound from green tea known for its antioxidant effects and therapeutic benefits, whose glycosylation could increase its bioavailability and improve its bioactive properties. The glycosynthase BGL-1-E521G produced a β-glucoside and a β-sophoroside of EGCG, while the thioglycoligase BxTW1-E495A formed the β-xyloside of EGCG. Glycosylation occurred in the 5″ and 4″ positions of EGCG, respectively. In this work, the reaction conditions for glycosides’ production were optimized, achieving around 90% conversion of EGCG with BGL-1-E521G and 60% with BxTW1-E495A. The glycosylation of EGCG caused a slight loss of its antioxidant capacity but notably increased its solubility (between 23 and 44 times) and, in the case of glucoside, also improved its thermal stability. All three glycosides showed better antiproliferative properties on breast adenocarcinoma cell line MDA-MB-231 than EGCG, and the glucosylated and sophorylated derivatives induced higher neuroprotection, increasing the viability of SH-S5Y5 neurons exposed to okadaic acid.

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Peng, Wenwen, Xiaoxiang Fu, Yuyan Li, Zhonghua Xiong, Xugen Shi, Fang Zhang, Guanghua Huo, and Baotong Li. "Phytochemical Study of Stem and Leaf of Clausena lansium." Molecules 24, no. 17 (August 28, 2019): 3124. http://dx.doi.org/10.3390/molecules24173124.

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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

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Hanessian, Stephen, Dongxu Qiu, Hubli Prabhanjan, Gurijala V. Reddy, and Boliang Lou. "Synthesis of clustered D-GalNAc (Tn) and D-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold." Canadian Journal of Chemistry 74, no. 9 (September 1, 1996): 1738–47. http://dx.doi.org/10.1139/v96-192.

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The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines. Key words: glycoside synthesis, 2-thiopyridyl carbonate, glycosyl donors and glycopeptide motifs

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Arnold, Ulrike W., Christian Zidorn, Ernst P. Ellmerer, and Hermann Stuppner. "Iridoid and Phenolic Glycosides from Wulfenia carinthiaca." Zeitschrift für Naturforschung C 57, no. 11-12 (December 1, 2002): 969–75. http://dx.doi.org/10.1515/znc-2002-11-1202.

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Two new phenylpropanoid glycosides (2′-O-acetylplantamajoside and 2′-O, 6″-O-diacetylplantamajoside), a new iridoid glycoside (10-O-(cinnamoyl)-6′-O-(desacetylalpinosidyl)-catalpol), the two known iridoid glycosides globularin and isoscrophularioside, and the known phenylpropanoid glycoside platamajoside were isolated from the methanolic extract of the underground parts of Wulfenia carinthiaca. Structure elucidations were based on high-resolution mass spectrometry and extensive 1-D and 2-D NMR spectroscopy.

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Silchenko, Alexandra S., Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok, Ekaterina A. Yurchenko, and Vladimir I. Kalinin. "Structure of Cucumariosides H5, H6, H7 and H8, Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix and Unprecedented Aglycone with 16,22-Epoxy-group." Natural Product Communications 6, no. 8 (August 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600806.

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Four new triterpene glycosides cucumariosides H5 (1), H6 (2), H7 (3) and H8 (4) along with the known cucumarioside H (5) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. The structures of glycosides 1–4 were elucidated on the basis of spectral data (2D NMR and MS). Glycosides 1–4 belong to the group of cucumariosides H, having branched rare pentasaccharide carbohydrate moieties with one sulfate group and 3- O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1–3 and 5 differ from each other in structures of side chains of the aglycones, while cucumarioside H8 (4) has a novel aglycone with unprecedented 16(22)-epoxy-group, never found in the sea cucumbers glycosides. Glycosides 1–3, and 5 were cytotoxic against mouse lymphocytes and hemolytic against mouse erythrocytes. Glycoside 2 was less active in comparison with others.

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22

Iguchi, Tomoki, Naoki Takahashi, and Yoshihiro Mimaki. "A Total of Eight Novel Steroidal Glycosides Based on Spirostan, Furostan, Pseudofurostan, and Cholestane from the Leaves of Cestrum newellii." Molecules 25, no. 19 (September 28, 2020): 4462. http://dx.doi.org/10.3390/molecules25194462.

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Previously, various steroidal glycosides were reported from plants of Cestrum species. However, phytochemical investigation has not been conducted on Cestrum newellii. A systematic phytochemical investigation of the leaves of C. newellii resulted in the isolation of eight novel steroidal glycosides (1–8), which were classified into three spirostanol glycosides (1–3), two furostanol glycosides (4 and 5), two pseudofurostanol glycosides (6 and 7), and one cholestane glycoside (8). In addition, three known cholestane glycosides (9–11) were isolated and identified. The structures of the new compounds were determined based on spectroscopic data and chemical transformations. Compounds 1 and 2 are spirostanol glycosides having hydroxy groups at C-2, C-3, C-12, and C-24 of the aglycone moiety. Although C. newellii is known to be a poisonous plant, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide assay exhibited that none of the isolated compounds were cytotoxic to HL-60 human promyelocytic leukemia cells.

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23

Riemann, I., W. D. Fessner, M. A. Papadopoulos, and M. Knorst. "C-Glycosides by Aqueous Condensation of β-Dicarbonyl Compounds with Unprotected Sugars." Australian Journal of Chemistry 55, no. 2 (2002): 147. http://dx.doi.org/10.1071/ch02012.

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Condensation of 1,3-diketones with unprotected aldoses in water, under mildly alkaline conditions, provides a�convenient and effective route to C-glycosidic ketones in high yields. Reactions usually proceed with high β`anomeric' stereoselectivity because product composition is determined by thermodynamic control. Mechanistically, the condensation follows a typical Knoevenagel scheme, after which an intramolecular oxa-Michael cyclization determines C-glycoside configuration by following an exo- or endo-trig pathway. With open-chain 1,3-diketones, an ensuing retro-Claisen fragmentation occurs to furnish simple glycosyl monoketones. The C-glycosides then slowly further dehydrate under the reaction conditions to give 2,5-disubstituted furans.

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24

Maldonado, Francisco, José A. Yuri, Amalia Neira, and Iván Razmilic. "Total phenolics, quercetin glycosides and antioxidant activity in organic and conventional orchards in three apple cultivars during fruit growth." Spanish Journal of Agricultural Research 20, no. 4 (November 11, 2022): e0805. http://dx.doi.org/10.5424/sjar/2022204-19549.

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Aim of study: To evaluate whether organic and conventional management practices, cultivar and fruit growth stage affect total phenolic content, antioxidant activity and quercetin glycosides in apples of three cultivars. Area of study: The trials were conducted in commercial orchards located in Chimbarongo, O’Higgins Region, Chile. Material and methods: Two types of orchard management (organic and conventional) were studied in three apple cultivars: Gala 'Brookfield', Granny Smith and Fuji 'Raku Raku'. Total phenolic content, antioxidant activity and quercetin glycosides were evaluated according to management practices, fruit growth stage, cultivar, fruit weight and skin surface. Data were analyzed statistically using a truncated multiple regression model. Main results: No differences were found between organic and conventional management regarding polyphenol concentration and antioxidant activity, except for specific quercetin glycosides. However, significant differences were observed between cultivars in both variables, as well as in fruit development throughout the season, which showed a significant dilution of polyphenols and antioxidant activity as the fruit grew. Research highlights: Cultivar and fruit growth stage were decisive in total phenolic content, glycosidic quercetins and apples antioxidant activity. Conventional and organic management practices were significant for quercetin glycoside concentration, which is the main polyphenol in apples.

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25

Aminin, Dmitry L., Alexandra S. Silchenko, Sergey A. Avilov, Vadim G. Stepanov, and Vladimir I. Kalinin. "Immunomodulatory Action of Monosulfated Triterpene Glycosides from the Sea Cucumber Cucumaria okhotensis: Stimulation of Activity of Mouse Peritoneal Macrophages." Natural Product Communications 5, no. 12 (December 2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501207.

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Six monosulfated triterpene glycosides, frondoside A1 (1), okhotoside B1 (2), okhotoside A1-1 (3), frondoside A (4), okhotoside A2-1 (5) and cucumarioside A2-5 (6), isolated from Cucumaria okhotensis Levin et Stepanov, stimulate spreading and lysosomal activity of mouse macrophages and ROS-formation in the macrophages. The highest macrophage spreading and stimulation of their lysosomal activity was induced by glycosides 1, 4 and 6. All glycosides similarly stimulate ROS formation in macrophages, but glycoside 2 caused minimal stimulation.

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26

Miller, Rebecca E., Roslyn M. Gleadow, and Ian E. Woodrow. "Cyanogenesis in tropical Prunus turneriana: characterisation, variation and response to low light." Functional Plant Biology 31, no. 5 (2004): 491. http://dx.doi.org/10.1071/fp03218.

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This study characterised three aspects of cyanogenesis in the late successional tropical rainforest species Prunus turneriana (F.M.Bailey) Kalkman. First, all tissues were found to be highly cyanogenic, containing combinations of the cyanogenic glycosides (R)-prunasin, (S)-sambunigrin, and amygdalin. Second, the progeny of a single parent tree varied markedly and continuously in their cyanogenic glycoside content, indicating that this variation is genetically based. Third, we investigated resource allocation to cyanogenic glycosides in light treatments representative of rainforest understorey and gap environments. Contrary to our hypothesis that under low light, photosynthetic gain would be maximised by the reallocation of nitrogen from defence to the photosynthetic system, we found no difference in cyanogenic glycoside concentration, or the proportion of nitrogen allocated to cyanogenic glycoside, between high and low light. However, within the plant, shade affected a significant change in distribution of cyanogenic glycosides between young and old leaves. There was an increased allocation of cyanogenic glycosides to old, expanded and photosynthetically productive leaves, a pattern which appears inconsistent with predictions of optimal defence theories, and the results of other studies. We suggest that such a strategy may be advantageous for seedlings of tree species that can only reach a reproductive stage following the creation of a canopy gap.

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27

Frański, R., P. Bednarek, D. Siatkowska, P. Wojtaszek, and M. Stobiecki. "Application of mass spectrometry to structural identification of flavonoid monoglycosides isolated from shoot of lupin (Lupinus luteus L.)." Acta Biochimica Polonica 46, no. 2 (June 30, 1999): 459–73. http://dx.doi.org/10.18388/abp.1999_4177.

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Flavonoid glycosides constitute important group of plant secondary metabolites. This class of natural products play significant role in different physiological processes. A new methodological approach where mass spectrometric techniques are applied to structural studies of this class of compounds is presented. Four flavonoid O-monoglycosides and one C-monoglycoside were isolated from green parts of lupin (Lupinus luteus L.). Several different mass spectrometric techniques were applied to structural elucidation of isolated compounds. Desorption ionization mass spectrometry was used for registration of mass spectra of intact and derivatized (permethylated) flavonoid glycosides. In some cases electron impact mass spectra of permethylated compounds were also recorded. Methylated samples after methanolysis and further derivatization of free hydroxyl groups (methylation or acetylation) were analyzed with gas chromatography-mass spectrometry. Combined information drawn from the registered mass spectra enabled us to define molecular mass, structure of aglycones and sugars, and positions of glycosidic bonds on the aglycon. Structures of four flavonoid monoglycosides were elucidated as follows: genistein 7-O-glucoside (1), genistein 4'-O-glucoside (2), 2'-hydroxygenistein 7-O-glucoside (3), and apigenin or genistein 8-C-glycoside (5). For the fourth O-glycoside (4) only molecular mass and masses of the aglycone and sugar were estimated.

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28

Terao, Junji. "Potential Role of Quercetin Glycosides as Anti-Atherosclerotic Food-Derived Factors for Human Health." Antioxidants 12, no. 2 (January 23, 2023): 258. http://dx.doi.org/10.3390/antiox12020258.

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Quercetin is a monomeric polyphenol of plant origin that belongs to the flavonol-type flavonoid subclass. Extensive studies using cultured cells and experimental model animals have demonstrated the anti-atherosclerotic effects of dietary quercetin in relation to the prevention of cardiovascular disease (CVD). As quercetin is exclusively present in plant-based foods in the form of glycosides, this review focuses on the bioavailability and bioefficacy of quercetin glycosides in relation to vascular health effects. Some glucose-bound glycosides are absorbed from the small intestine after glucuronide/sulfate conjugation. Both conjugated metabolites and deconjugated quercetin aglycones formed by plasma β-glucuronidase activity act as food-derived anti-atherogenic factors by exerting antioxidant, anti-inflammatory, and plasma low-density lipoprotein cholesterol-lowering effects. However, most quercetin glycosides reach the large intestine, where they are subject to gut microbiota-dependent catabolism resulting in deglycosylated aglycone and chain-scission products. These catabolites also affect vascular health after transfer into the circulation. Furthermore, quercetin glycosides may improve gut microbiota profiles. A variety of human cohort studies and intervention studies support the idea that the intake of quercetin glycoside-rich plant foods such as onion helps to prevent CVD. Thus, quercetin glycoside-rich foods offer potential benefits in terms of cardiovascular health and possible clinical applications.

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29

Avilov, Sergey A., Olga A. Drozdova, Vladimir I. Kalinin, Anatoly I. Kalinovsky, Valentin A. Stonik, Elena N. Gudimova, Ricardo Riguera, and Carlos Jiménez. "Article." Canadian Journal of Chemistry 76, no. 2 (February 1, 1998): 137–41. http://dx.doi.org/10.1139/v97-218.

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Frondoside C (1) is a new sulfated nonholostane triterpene glycoside obtained (with the glycosides closed by aglycone structure as impurities) from the sea cucumber Cucumaria frondosa. Its structure has been elucidated on the basis of spectral data (NMR and MS) of compound 1 and of its desulfated derivative (2) obtained by solvolysis. Frondoside C (1) is just the seventh glycoside reported from sea cucumbers, having a lanostane-type aglycone devoid of the typical 18(20)- lactone ring.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterepene glycosides, antitumor activity.

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30

Nazemiyeh, Hossein, Abbas Delazar, Mohammed-Ali Ghahramani, Amir-Hossein Talebpour, Lutfun Nahar, and Satyajit D. Sarker. "Phenolic Glycosides from Phlomis lanceolata (Lamiaceae)." Natural Product Communications 3, no. 1 (January 2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300112.

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Preparative reversed-phase HPLC analyses of the methanol extract of the aerial parts of Phlomis lanceolata afforded three phenolic glycosides including a flavonol glycoside, peterin (1), and two phenylethanoid glycosides, viridoside (2) and peteroside (3). Compounds 1 and 3 are novel natural products. The structures of all three compounds were elucidated by spectroscopic means.

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31

Silchenko, Alexandra S., Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok, Ekaterina A. Yurchenko, Igor Yu Dolmatov, Alexander M. Savchenko, and Vladimir I. Kalinin. "Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii. II. Structure and Biological Action of Cladolosides A1-A6." Natural Product Communications 9, no. 10 (October 2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901006.

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Six new triterpene glycosides, cladolosides A1–A6(1–6), have been isolated from the Vietnamese sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. All the glycosides have nonsulfated tetrasaccharide linear carbohydrate moieties. Glycoside 6 has a glucose residue as the third monosaccharide unit, while the rest of the compounds comprise a xylose in this postion of the carbohydrate chain. Glycosides 1–6 differ from each other in the structures of their holostane aglycones. Cytotoxic activities of glycosides 1–6 were studied against mouse spleenocytes, along with hemolytic activities against mouse erythrocytes. All the compounds, except cladoloside A5(5) posessing a hydroxy-group in the aglycone side chain, demonstrated rather strong cytotoxic and hemolytic effects. The most active glycosides were cladolosides A1(1) and A2(2) having two O-acetic groups and the xylose residue in the third position of the sugar chain.

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32

Kim, Jin-Man, Jong-Ho Koh, and Jung-Min Park. "Validation of an HPLC Method for Pretreatment of Steviol Glycosides in Fermented Milk." Foods 10, no. 10 (October 14, 2021): 2445. http://dx.doi.org/10.3390/foods10102445.

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Steviol glycosides are used in food and beverages worldwide as natural sweeteners, serving as a low-calorie sugar substitute. The acceptable daily intake of steviol is 0–4 mg/kg body weight. The rising demand for dairy products has led to a corresponding increase in the use of steviol glycosides in such products. Therefore, it is important to analyze the levels of steviol glycosides in dairy products. Dairy products have high fat contents and unique emulsion characteristics, conferred by a mixture of fat globules, casein micelles, whey proteins, and numerous other small molecules. These characteristics may interfere with the estimation of steviol glycoside levels; therefore, dairy samples require pretreatment. We aimed to develop an objective test for measuring the levels of steviol glycosides through the development of an efficient pretreatment method. In this study, the steviol glycoside content in dairy products was evaluated by using various methods, and an optimal pretreatment method was determined. We used high-performance liquid chromatography to assess the selectivity, linearity, limit of detection, limit of quantification, accuracy, precision, and recovery rate. Calibration curves were linear in the range of 1–50 mg/kg, with a coefficient of determination of ≥0.999. The limit of detection and limit of quantification were in the ranges of 0.11–0.56 and 0.33–1.69 mg/kg, respectively. The relative standard deviation (%) represents the precision of a measurement. The RSD relative standard deviationof recovery varied between 0.16% and 2.83%, and recovery of the analysis varied between 83.57% and 104.84%. These results demonstrate the reliability of the method for measuring the steviol glycoside content. This method can be used for the simple pretreatment of steviol glycosides and can provide an accurate determination of steviol glycoside content in emulsified food matrices, such as dairy products.

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33

Berin, A., and N. M. S. Sunyoto. "The effect of methods and drying temperature on glycoside content (Stevioside and Rebaudioside A) in Stevia (Stevia rebaudiana): A systematic review." IOP Conference Series: Earth and Environmental Science 924, no. 1 (November 1, 2021): 012044. http://dx.doi.org/10.1088/1755-1315/924/1/012044.

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Abstract The utilization of Stevia rebaudiana as an alternative sweetener in Indonesia is still low, this is caused by a lack of information about its processing from raw material until the extraction process to obtain the glycosides content. Glycosides are the sweetener compound in Stevia rebaudiana with a sweet taste up to 300 times of sucrose, which are stevioside and rebaudioside A. To obtain the glycosides content in stevia, stevia needs to be dried after harvest. Then, dried Stevia will be extracted to obtain the glycosides content. The research method used in this study was a systematic review of selected journals on a specific topic, then were analysed in both the theory and content. The purpose of this research is to analysing the effect of drying temperature on different drying methods on the glycoside compound of Stevia rebaudiana, observing drying temperature that is useful to obtain the optimal glycoside compound in Stevia rebaudiana, and to recommend the utilization of Stevia rebaudiana as an alternative sweetener in Indonesia. The result is the high temperature and low temperature can decrease the glycoside compound in Stevia rebaudiana. The dried temperature that is effective for drying stevia leaves to obtain the maximal glycosides is in the range of 40-60°C. The drying method that is effectively used is by an oven at 60°C as the suggested temperature. Stevia’s sweetener is potentially applied and developed in Indonesia and can be served in powder form because it is more efficient and decrease defect in dried condition and a much longer lifetime.

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34

Jizba, Josef V., Petr Sedmera, Věra Přikrylová, Jindřich Vokoun, Karel Mikulík, and Zdenko Vaněk. "New semisynthetic anthracycline glycosides." Collection of Czechoslovak Chemical Communications 54, no. 4 (1989): 1104–17. http://dx.doi.org/10.1135/cccc19891104.

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3-Trifluoroacetamido-4-O-trifluoroacetyl-2,3,6-trideoxy-α,β-L-lyxopyranosyl chloride (VII) was coupled under Koenigs-Knorr glycosidation conditions to (7S)-O-(2-hydroxyethyl)daunomycinone (IV), (7R)-O-(2-hydroxyethyl)daunomycinone (V), and (7S)-O-(4-hydroxy-2-butynyl)daunomycinone (VI). The deprotection of isolated N-trifluoroacetyl derivatives of α- and β-glycosides XVI, XVII, XX, XXI, and XXIV yielded free glycosides XVIII, XIX, XXII, XXIII, and XXV. Their anomeric configuration was determined by NMR spectroscopy. Reaction of 3,4-di-O-acetyl-2,6-dideoxy-α,β-L-arabinopyranosyl chloride (II) with IV gave glycosides XII and XIII. Their deacetylation provided free glycosides XIV and XV. An analogueous reaction with 3-acetamido-4-O-acetyl-2,3,6-trideoxy-α,β-L-lyxopyranosyl chloride (III) with IV lead to the N-acetyl glycoside IX only.

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35

Zou, Wei. "C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors." Current Topics in Medicinal Chemistry 5, no. 14 (November 1, 2005): 1363–91. http://dx.doi.org/10.2174/156802605774642999.

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36

Zelepuga, Elena A., Alexandra S. Silchenko, Sergey A. Avilov, and Vladimir I. Kalinin. "Structure-Activity Relationships of Holothuroid’s Triterpene Glycosides and Some In Silico Insights Obtained by Molecular Dynamics Study on the Mechanisms of Their Membranolytic Action." Marine Drugs 19, no. 11 (October 25, 2021): 604. http://dx.doi.org/10.3390/md19110604.

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The article describes the structure-activity relationships (SAR) for a broad series of sea cucumber glycosides on different tumor cell lines and erythrocytes, and an in silico modulation of the interaction of selected glycosides from the sea cucumber Eupentacta fraudatrix with model erythrocyte membranes using full-atom molecular dynamics (MD) simulations. The in silico approach revealed that the glycosides bound to the membrane surface mainly through hydrophobic interactions and hydrogen bonds. The mode of such interactions depends on the aglycone structure, including the side chain structural peculiarities, and varies to a great extent. Two different mechanisms of glycoside/membrane interactions were discovered. The first one was realized through the pore formation (by cucumariosides A1 (40) and A8 (44)), preceded by bonding of the glycosides with membrane sphingomyelin, phospholipids, and cholesterol. Noncovalent intermolecular interactions inside multimolecular membrane complexes and their stoichiometry differed for 40 and 44. The second mechanism was realized by cucumarioside A2 (59) through the formation of phospholipid and cholesterol clusters in the outer and inner membrane leaflets, correspondingly. Noticeably, the glycoside/phospholipid interactions were more favorable compared to the glycoside/cholesterol interactions, but the glycoside possessed an agglomerating action towards the cholesterol molecules from the inner membrane leaflet. In silico simulations of the interactions of cucumarioside A7 (45) with model membrane demonstrated only slight interactions with phospholipid polar heads and the absence of glycoside/cholesterol interactions. This fact correlated well with very low experimental hemolytic activity of this substance. The observed peculiarities of membranotropic action are in good agreement with the corresponding experimental data on hemolytic activity of the investigated compounds in vitro.

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Chen, Xiaochuan, and Qixiu Zhu. "Pregnane Glycoside, Lignan Glycosides, Triterpene Glycosyl Ester and Flavonoid Glycosides from Rubus amabilis." Planta Medica 67, no. 3 (2001): 270–73. http://dx.doi.org/10.1055/s-2001-11996.

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38

Asih, Ida Ayu Raka Astiti, Wiwik Susanah Rita, Wayan Suirta, and Ahmad Fudholi. "Antioxidant Activity of Flavonoid Glycoside Extract of Solanum Betaceum on the Kidney of Wistar Rats." International Journal of Design & Nature and Ecodynamics 17, no. 2 (April 27, 2022): 319–23. http://dx.doi.org/10.18280/ijdne.170220.

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Flavonoid glycosides are a type of secondary metabolite that is one of the active chemicals in plants. The antioxidant efficacy of solanum betaceum flavonoid glycosides extract on malondialdehyde levels and superoxide dismutase activity in Wistar rat kidneys with maximum physical activity is the focus of this investigation. The DPPH technique was used to conduct an in vitro activity test. The in vivo test includes four treatment groups: control, stress, ethanol extract, and flavonoid glycoside extract group. Swimming almost one and a half hours every day for five days and being fed and drinking ad libitum is the treatment for stress conditions. Ethanol and flavonoids glycosides extract were given at doses of 50 mg/kg/BW/day respectively. In vitro test result with DPPH technique glycoside flavonoid extract was categorized as a strong antioxidant with an IC50 of 69.89 ppm. The intake of ethanol extract and flavonoid glycoside extract at a dose of 50 mg / Kg BW significantly lower MDA levels (p < 0.05), and can prevent oxidative stress through SOD in Wistar rat kidneys.

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39

Utami, Prawesty Diah, Herin Setianingsih, and Dewi Ratih Tirto Sari. "In Silico Approach Triterpene Glycoside of H. atra Targeting Orotidine 5-Monophosphate Decarboxylase Protein (PfOMPDC) in P. falciparum Infection Mechanism." BioMed Research International 2024 (April 1, 2024): 1–14. http://dx.doi.org/10.1155/2024/5924799.

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This study accessed the potential antimalarial activity of triterpene glycoside of H. atra through targeting orotidine 5-monophosphate decarboxylase protein (PfOMPDC) in P. falciparum by molecular docking. Nine triterpene glycosides from H. atra extract modeled the structure by the Corina web server and interacted with PfOMPDC protein by using Hex 8.0.0. The docking results were visualized and analyzed by Discovery Studio version 21.1.1. 17-Hydroxyfuscocineroside B showed the lowest binding energy in PfOMPDC interaction, which was -1,098.13 kJ/mol. Holothurin A3, echinoside A, and fuscocineroside C showed low binding energy. Nine triterpene glycosides of H. atra performed interaction with PfOMPDC protein at the same region. Holothurin A1 posed interaction with PfOMPDC protein by 8 hydrogen bonds, 3 hydrophobic interactions, and 8 unfavorable bonds. Several residues were detected in the same active sites of other triterpene glycosides. Residue TYR111 was identified in all triterpene glycoside complexes, except holothurin A3 and calcigeroside B. In summary, the triterpene glycoside of H. atra is potentially a drug candidate for malaria therapeutic agents. In vitro and in vivo studies were required for further investigation.

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40

Everest, Michael A., Michael P. Gonella, Holly G. Bowler, and Joshua R. Waschak. "How Toxic is Milkweed when Harvested and Cooked according to Myaamia Tradition?" Ethnobiology Letters 10, no. 1 (August 6, 2019): 50–56. http://dx.doi.org/10.14237/ebl.10.1.2019.1487.

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Asclepias syriaca L. (common milkweed) is known to contain sufficient amounts of cardiac glycosides, which are known to be toxic to humans. Nonetheless, it is traditionally used for food by Native Americans, including the Myaamia people of Indiana and Oklahoma. In order to test the hypothesis that traditional horticultural and culinary practices prevent the Myaamia from ingesting toxic levels of cardiac glycosides, we have determined the level of glycosides (digitoxin equivalent) in A. syriaca 1) in various parts of the plant, 2) at various heights for pre-reproductive plants, and 3) before and after cooking according to traditional Myaamia procedures. Plants were grown, harvested, dried, ground, and extracted twice with ethanol. The amount of digitoxin-equivalent glycoside in plant extract was determined spectrophotometrically using 2,2’,4,4’-tetranitrodiphenyl, a selective derivatizing agent. We find that all parts of the plant contain significant levels of cardiac glycosides at all stages of growth. Plants harvested as young shoots for food, the common practice of the Myaamia, contain slightly lower levels of cardiac glycosides when compared to the leaves and stems of older, taller plants. Moreover, the toxicity is significantly reduced by the traditional Myaamia cooking procedure—a repeated boiling with several changes of water. Therefore, it appears as though the risk of glycoside poisoning from traditional Myaamia use of milkweed for food is moderated by their harvesting practice and traditional cooking procedure.

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41

Miyagawa, Yasuyuki, Takahito Mizukami, Hiroshi Kamitakahara, and Toshiyuki Takano. "Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)." Holzforschung 68, no. 7 (October 1, 2014): 747–60. http://dx.doi.org/10.1515/hf-2013-0164.

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Abstract Twelve monolignol (coniferyl alcohol, sinapyl alcohol and p-coumaryl alcohol) β-glycosides (β-glucosides, β-galactosides, β-xylosides and β-mannosides) were synthesised to obtain fundamental NMR data for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs). That is, the 1,2-trans glycosides (the β-glucosides, β-galactosides and β-xylosides) and the 1,2-cis glycosides (the β-mannosides) were synthesized by means of Koenig-Knorr glycosylation and β-selective Mitsunobu glycosylation strategies, respectively. In addition, dihydromonolignol and p-hydroxybenzaldehyde derivative β-glycosides were also prepared from the corresponding monolignol glycosides and their intermediates, respectively. The correlation observed for the C1β-H1β bonds of the sugar moieties in the HSQC spectra of the all β-glycosides varied and were in the range of δC/δH 96–104/4.7–5.4 ppm. Especially, it was found that the correlations derived from the C1β-H1β bonds of the guaiacyl and p-hydroxyphenyl β-mannosides were close to those derived from the C1α-H1α bonds of the 4-O-methyl-α-D-glucuronic acid moieties described in the literature.

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42

van Rantwijk, F., M. Woudenberg-van Oosterom, and R. A. Sheldon. "Glycosidase-catalysed synthesis of alkyl glycosides." Journal of Molecular Catalysis B: Enzymatic 6, no. 6 (June 1999): 511–32. http://dx.doi.org/10.1016/s1381-1177(99)00042-9.

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43

Kim, Tae, Young Cho, HoonGyu Park, Tae Lee, and Hakwon Kim. "Comparison of the Inhibitory Activities of 5,6-Dihydroergosterol Glycoside α- and β-Anomers on Skin Inflammation." Molecules 24, no. 2 (January 21, 2019): 371. http://dx.doi.org/10.3390/molecules24020371.

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Chronic skin inflammatory diseases, such as atopic dermatitis, are associated with a dysfunctional skin barrier due to an increase in various inflammatory stimuli, for instance inflammatory cytokines and chemokines. In particular, CCL17 and CCL22 expression is increased in patients with chronic skin inflammation. In this study, we synthesized several α- and β-anomers of dihydroergosterol (DHE)-glycosides and assessed their effects on CCL17 and CCL22 expression. We confirmed that the β-anomers of DHE-glycosides were superior to α-anomers of DHE-glycosides in inhibiting CCL17 and CCL22 mRNA and protein expression. In addition, we determined that DHE-glycoside β-anomers showed strong inhibitory activity towards pro-inflammatory cytokine mRNA and protein expression, including that of TNF-α, IL-6, and IL-1β- in stimulated HaCaT cells. These results imply that DHE-glycoside α- and β-anomers should be separated during synthesis of drugs for chronic skin inflammation. Our results also suggest that β-anomers of DHE-glycosides may play an important role as new drugs for chronic skin inflammation because of their ability to inhibit the skin inflammatory biomarker proteins CCL17 and CCL22.

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44

Shvets, Stepan, Irina Nedova, Pavel Kintia, Carla Bassarelo, Cosimo Pizza, and Sonia Piacente. "Steroidal Glycosides from the Roots of Solanum Melongena L." Chemistry Journal of Moldova 4, no. 2 (December 2009): 72–77. http://dx.doi.org/10.19261/cjm.2009.04(2).08.

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One new cholestane glycoside, six steroidal glycosides of spirostane series and one pregnane glycoside have been isolated from the roots of Solanum melongena L. for the first time. Their structures were determined by physico-chemical methods.

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45

Deng, Xuming, Hu Shang, Jiajia Chen, Jun Wu, Tao Wang, Yiqing Wang, Chensong Zhu, and Weijiang Sun. "Metabolomics Combined with Proteomics Provide a Novel Interpretation of the Changes in Flavonoid Glycosides during White Tea Processing." Foods 11, no. 9 (April 24, 2022): 1226. http://dx.doi.org/10.3390/foods11091226.

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In this study, nonvolatile metabolomics and proteomics were applied to investigate the change mechanism of flavonoid glycoside compounds during withering processing of white tea. With the extension of withering time, the content of the main flavonoid glycoside compounds significantly decreased, and then the flavonoid aglycones and water-soluble saccharides contents increased. However, the change trends of these compounds were inconsistent with the expression pattern of related biosynthesis pathway proteins, indicating that the degradation of flavonoid glycosides might exist in the withering process of white tea. One co-expression network that was highly correlated with variations in the flavonoid glycosides’ component contents during the withering process was identified via WGCNA. Further analysis revealed that the degradation of flavonoid glycosides may be related to the antioxidant action of tea leaves undergoing the withering process. Our results provide a novel characterization of white tea taste formation during processing.

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46

Deng, Xuming, Hu Shang, Jiajia Chen, Jun Wu, Tao Wang, Yiqing Wang, Chensong Zhu, and Weijiang Sun. "Metabolomics Combined with Proteomics Provide a Novel Interpretation of the Changes in Flavonoid Glycosides during White Tea Processing." Foods 11, no. 9 (April 24, 2022): 1226. http://dx.doi.org/10.3390/foods11091226.

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Abstract:

In this study, nonvolatile metabolomics and proteomics were applied to investigate the change mechanism of flavonoid glycoside compounds during withering processing of white tea. With the extension of withering time, the content of the main flavonoid glycoside compounds significantly decreased, and then the flavonoid aglycones and water-soluble saccharides contents increased. However, the change trends of these compounds were inconsistent with the expression pattern of related biosynthesis pathway proteins, indicating that the degradation of flavonoid glycosides might exist in the withering process of white tea. One co-expression network that was highly correlated with variations in the flavonoid glycosides’ component contents during the withering process was identified via WGCNA. Further analysis revealed that the degradation of flavonoid glycosides may be related to the antioxidant action of tea leaves undergoing the withering process. Our results provide a novel characterization of white tea taste formation during processing.

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47

Du, Ting, Yang Wang, Huan Xie, Dong Liang, and Song Gao. "Fragmentation Patterns of Phenolic C-Glycosides in Mass Spectrometry Analysis." Molecules 29, no. 13 (June 21, 2024): 2953. http://dx.doi.org/10.3390/molecules29132953.

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Background: Many phenolic C-glycosides possess nutritional benefits and pharmacological efficacies. However, the MS/MS fragmentation pattern of phenolic C-glycosides analysis is understudied. This paper aims to determine the MS/MS fragmentation patterns of phenolic C-glycosides. Method: Ten compounds with different sugar moieties, aglycones, and substitutes were analyzed to determine the impact of these structural features on MS/MS fragmentation using UPLC-QTOF-MS analysis. Results: The results showed that water loss followed by RDA reaction and alpha cleavage in the C-C bonded sugar moieties are the major fragmentation pathways. Additionally, the sugar cleavage was not affected by the skeleton and the substitute of the aglycones. These results suggested that the fragmentation patterns of phenolic C-glycosides differ from those in the O-glycosides, where the O-C glycosidic bond is the most cleavage-liable bond in MS/MS analysis. Conclusions: These MS/MS fragmentation patterns can be used for the identification of C-glycosides from dietary components and herbal medicine as well as developing robust methods using MRM methods to quantify C-glycosides.

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Pislyagin, Evgeny A., Dmitry L. Aminin, Alexandra S. Silchenko, Sergey A. Avilov, Pelageya V. Andryjashchenko, Vladimir I. Kalinin, and Krishna Padmakumar. "Immunomodulatory Action of Triterpene Glycosides Isolated from the Sea Cucumber Actinocucumis typica. Structure-Activity Relationships." Natural Product Communications 9, no. 6 (June 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900610.

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Stimulation of lysosomal activity and ROS formation in mouse peritoneal macrophages by five triterpene glycosides, typicosides A1 (1), A2 (2), B1 (3), C1 (4) and C2 (5) has been studied and compared with their cytotoxic activities. Glycosides 1–3 possess moderate activities, but the most cytotoxic glycoside 5 is not active. Typicoside C1 (4), with low toxicity, was proved to be the most active concerning stimulation of ROS formation. This is the first example of a triterpene glycoside from sea cucumbers with low cytotoxicity, but which demonstrates a strong immunostimulatory effect on mouse peritoneal macrophages in vitro.

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Ivanova, Antoaneta, Bozhanka Mikhova, Tatyana Stambolijska, and Ivanka Kostova. "Lignan and Coumarin Glycosides from Haplophyllum suaveolens." Zeitschrift für Naturforschung C 56, no. 5-6 (June 1, 2001): 329–33. http://dx.doi.org/10.1515/znc-2001-5-602.

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Two new lignan glycosides of dibenzylbutyrolactol type (haplomarin) and arylnaphthalene type (haploborin) were isolated from the aerial parts of Haplophyllum suaveolens together with the known arylnaphthalene lignan glycoside arabelline and hydroxycoumarin glycoside xeroboside. So far arabelline is found only in H. buxbaumii. This is the first report of the isolation of xeroboside from Haplophyllum.

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Silchenko, Alexandra S., Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok, Ekaterina A. Martyyas, and Vladimir I. Kalinin. "Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic Action of Cucumariosides A2, A7, A9, A10, A11, A13 and A14, Seven New Minor Non-Sulfated Tetraosides and an Aglycone with an Uncommon 18-Hydroxy Group." Natural Product Communications 7, no. 7 (July 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700710.

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Seven new minor triterpene glycosides, cucumariosides A2 (1), A7 (2), A9 (3), A10 (4), A11 (5), A13 (6) and A14 (7) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–7 belong to the group of cucumariosides A, having linear tetrasaccharide carbohydrate moieties without any sulfate group and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1, 2, 5-7 differ from each other in side chain structures in aglycone moieties, while cucumarioside A10 (4) has a 23,24,25,26,27-pentanorlanostane aglycone with 18(16)-lactone. Cucumarioside A9 (3), having an uncommon 18-hydroxy group, is the second representative of the unique metabolically active glycosides that are regarded as intermediates of glycoside biosynthesis in sea cucumbers. Cytotoxic activities of glycosides 1–7 and cucumarioside A8 (8) against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Cucumariosides A2 (1), A8 (8) and A13 (6) demonstrated high hemolytic activities. Glycosides 1, 4 and 6 showed moderate cytotoxic activity. Only cucumarioside A8 (8), having an 18-oxymethylene group and a 24(25)-double bond, was very active in all the tests.

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Journal articles on the topic 'Glycosides'

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