Reaction Pattern and Mechanistic Aspects of Iodine and Iodine-Based Reagents in Selenylation of Aliphatic, Aromatic, and (Hetero)Cyclic Systems.

Organoselenium compounds have been the subject of extensive research since the discovery of the biologically active compound ebselen. Ebselen has recently been found to show activity against the main protease of the virus responsible for COVID-19. Other organoselenium compounds are also well-known for their diverse biological activities, with such compounds exhibiting interesting physical properties relevant to the fields of electronics, materials, and polymer chemistry. In addition, the incorporation of selenium into various organic molecules has garnered significant attention due to the potential of selenium to enhance the biological activity of these molecules, particularly in conjunction with bioactive heterocycles. Iodine and iodine-based reagents play a prominent role in the synthesis of organoselenium compounds, being valued for their cost-effectiveness, non-toxicity, and ease of handling. These reagents efficiently selenylate a broad range of organic substrates, encompassing alkenes, alkynes, and cyclic, aromatic, and heterocyclic molecules. They serve as catalysts, additives, inducers, and oxidizing agents, facilitating the introduction of different functional groups at alternate positions in the molecules, thereby allowing for regioselective and stereoselective approaches. Specific iodine reagents and their combinations can be tailored to follow the desired reaction pathways. Here, we present a comprehensive review of the progress in the selenylation of organic molecules using iodine reagents over the past decade, with a focus on reaction patterns, solvent effects, heating, microwave, and ultrasonic conditions. Detailed discussions on mechanistic aspects, such as electrophilic, nucleophilic, radical, electrochemical, and ring expansion reactions via selenylation, multiselenylation, and difunctionalization, are included. The review also highlights the formation of various cyclic, heterocyclic, and heteroarenes resulting from the in situ generation of selenium intermediates, encompassing cyclic ketones, cyclic ethers, cyclic lactones, selenophenes, chromones, pyrazolines, pyrrolidines, piperidines, indolines, oxazolines, isooxazolines, lactones, dihydrofurans, and isoxazolidines. To enhance the reader's interest, the review is structured into different sections covering the selenylation of aliphatic sp2/sp carbon and cyclic sp2 carbon, and then is further subdivided into various heterocyclic molecules.

Bioinspired Selenium-Nitrogen Exchange (SeNEx) Click Chemistry Suitable for Nanomole-Scale Medicinal Chemistry and Bioconjugation.

Click chemistry is a powerful molecular assembly strategy for rapid functional discovery. The development of click reactions with new connecting linkage is of great importance for expanding the click chemistry toolbox. We report the first selenium-nitrogen exchange (SeNEx) click reaction between benzoselenazolones and terminal alkynes (Se-N to Se-C), which is inspired by the biochemical SeNEx between Ebselen and cysteine (Cys) residue (Se-N to Se-S). The formed selenoalkyne connection is readily elaborated, thus endowing this chemistry with multidimensional molecular diversity. Besides, this reaction is modular, predictable, and high-yielding, features fast kinetics (k2≥14.43 M-1 s-1), excellent functional group compatibility, and works well at miniaturization (nanomole-scale), opening up many interesting opportunities for organo-Se synthesis and bioconjugation, as exemplified by sequential click chemistry (coupled with ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) and sulfur-fluoride exchange (SuFEx)), selenomacrocycle synthesis, nanomole-scale synthesis of Se-containing natural product library and DNA-encoded library (DEL), late-stage peptide modification and ligation, and multiple functionalization of proteins. These results indicated that SeNEx is a useful strategy for new click chemistry developments, and the established SeNEx chemistry will serve as a transformative platform in multidisciplinary fields such as synthetic chemistry, material science, chemical biology, medical chemistry, and drug discovery.

Longan Polysaccharides with Covalent Selenylation Combat the Fumonisin B1-Induced Cell Toxicity and Barrier Disruption in Intestinal Epithelial (IEC-6) Cells.

In this study, the soluble, but non-digestible, longan (Dimocarpus longan Lour.) polysaccharides (LP) were extracted from dried longan fruits and then chemically selenylated to produce two selenylated products, namely SeLP1 and SeLP2, with different selenylation extents. The aim was to investigate their protective effects on rat intestinal epithelial (IEC-6) cells exposed to the food toxin fumonisin B1 (FB1). LP only contained total Se content of less than 0.01 g/kg, while SeLP1 and SeLP2 were measured with respective total Se content of up to 1.46 and 4.79 g/kg. The cell viability results showed that these two selenylated products were more efficient than LP in the IEC-6 cells in alleviating FB1-induced cell toxicity, suppressing lactate dehydrogenase (LDH) release, and decreasing the generation of intracellular reactive oxygen species (ROS). These two selenylated products were also more effective than LP in combating FB1-induced barrier disruption via increasing the transepithelial electric resistance (TEER), reducing the paracellular permeability, decreasing the mitochondrial membrane potential (MMP) loss, and maintaining cell barrier integrity by upregulating the tight-junction-related genes and proteins. FB1 caused cell oxidative stress and barrier dysfunction by activating the MAPK and mitochondrial apoptosis signaling pathways, while SeLP1 and SeLP2 could regulate the tMAPK- and apoptosis-related proteins to suppress the FB1-mediated activation of the two pathways. Overall, SeLP2 was observed to be more active than SeLP1 in the IEC-6 cells. In conclusion, the chemical selenylation of LP caused an activity enhancement to ameliorate the FB1-induced cell cytotoxicity and intestinal barrier disruption. Meanwhile, the increased selenylation of LP would endow the selenylated product SeLP2 with more activity.

Converting commercial Bi2O3 particles into Bi2O2Se@Bi4O8Se nanosheets for "rocking chair" zinc-ion batteries.

The development of a low-cost, high-capacity, and insertion-type anode is key for promoting "rocking chair" zinc-ion batteries. Herein, commercial Bi2O3 (BiO) particles are transformed into Bi2O2Se@Bi4O8Se (BiOSe) nanosheets through a simple selenylation process. The change in morphology from commercial BiO particle to BiOSe nanosheet leads to an increased specific surface area of the material. The enhanced electronic/ionic conductivity results in its excellent electrochemical kinetics. Ex situ XRD and XPS tests prove the intercalation-type mechanism of BiO and BiOSe as well as the superior electrochemical reversibility of BiOSe compared to BiO. Furthermore, the H+/Zn2+ co-insertion mechanism of BiOSe is revealed. This makes BiOSe to have low discharge plateaus of 0.38/0.68 V, a high reversible capacity of 182 mA h g-1 at 0.1 A g-1, and a long cyclic life of 500 cycles at 1 A g-1. Besides, the BiOSe//MnO2 "rocking chair" zinc-ion battery offers a high capacity of ≈90 mA h g-1 at 0.2 A g-1. This work provides a reference for turning commercial material into high-performance anode for "rocking chair" zinc-ion batteries.

Electro-Oxidative C3-Selenylation of Pyrido[1,2-a]pyrimidin-4-ones.

In this work, we achieved a C3-selenylation of pyrido[1,2-a]pyrimidin-4-ones using an electrochemically driven external oxidant-free strategy. Various structurally diverse seleno-substituted N-heterocycles were obtained in moderate to excellent yields. Through radical trapping experiments, GC-MS analysis and cyclic voltammetry study, a plausible mechanism for this selenylation was proposed.

Stepping Up the Kinetics of Li-O2 Batteries by Shrinking Down the Li2O2 Granules through Concertedly Enhanced Catalytic Activity and Photoactivity of Se-Doped LaCoO3.

Owing to their structural tunability for furnishing high catalytic activity and photoactivity, perovskite oxides are a class of promising materials for high-performance photocathode catalysts in a photoassisted lithium oxygen battery (LOB), which is still in its infancy. Herein, single-crystalline LaCoO3 (LCO) is successfully synthesized through a microwave-assisted approach and selenylated to simultaneously introduce anionic doping and oxygen vacancies, boosting not only the electrocatalytic activity toward reversible Li2O2 formation/decomposition, but also the photoactivity to further reduce the charge/discharge polarization. As a result, LOBs utilizing Se-doped LCO as the photocathode catalyst demonstrate a superior performance under illumination in all aspects of energy efficiency, specific capacity, and cycling stability, ranking among the best reported in the literature for perovskite oxides. The photoenhanced charge kinetics is found to be correlated with the accelerated Li2O2 nucleation with lowered granule size, which is key to both the improved charge/discharge capacity and reversibility. The results underscore the tailoring of perovskite structure to aggrandize both the catalytic activity and photoactivity for concertedly promoting the kinetics of LOBs.

Preparation, characterization and bioactivities of selenized polysaccharides from Lonicera caerulea L. fruits.

Native polysaccharide was obtained from Lonicera caerulea L. fruits (PLP). Two selenized polysaccharides (PSLP-1 and PSLP-2) were synthesized by the microwave-assisted HNO3-Na2SeO3 method, where the selenium (Se) contents were 228 ± 24 and 353 ± 36 µg/g, respectively. The molecular weights of PLP, PSLP-1, and PSLP-2 were 5.9 × 104, 5.6 × 104, and 5.1 × 104 kDa, respectively. PSLP-1 and PSLP-2 contained the same type of monosaccharides as PLP but with different molar ratios. The main chain structure of the native polysaccharide was not changed after selenization. PLP, PSLP-1, and PSLP-2 contained the same six types of glycosidic bonds. Bioactivity assays revealed that the two selenized polysaccharides possessed better antioxidant activities than PLP, but their bile acid-binding abilities and inhibitory activities on acetylcholinesterase (AChE) had weakened. In summary, PLP, PSLP-1, and PSLP-2 may be promising Se supplements in functional foods and inhibitors for the treatment of AChE.

Monosaccharide Composition and In Vitro Activity to HCT-116 Cells of Purslane Polysaccharides after a Covalent Chemical Selenylation.

The anti-cancer effects of selenylated plant polysaccharides are a focus of research. As a natural plant with extensive biological effects, there have been few studies related to edible purslane (Portulaca oleracea L.). Thus, in this study, soluble P. oleracea polysaccharides (PPS) were extracted from the dried P. oleracea and then selenylated chemically using the HNO3-Na2SeO3 method to obtain two selenylated products, namely, SePPS1 and SePPS2. Compared with the extracted PPS, SePPS1 and SePPS2 had much higher Se contents (840.3 and 1770.5 versus 66.0 mg/kg) while also showing lower contents in three saccharides-arabinose, fucose, and ribose-and higher contents in seven saccharides including galactose, glucose, fructose, mannose, rhamnose, galacturonic acid, and glucuronic acid, but a stable xylose content demonstrated that the performed chemical selenylation of PPS led to changes in monosaccharide composition. Moreover, SePPS1 and SePPS2 shared similar features with respect to monosaccharide composition and possessed higher bioactivity than PPS in human colon cancer HCT-116 cells. Generally, SePPS1 and SePPS2 were more active than PPS with respect to cell growth inhibition, the alteration of cell morphology, disruption of mitochondrial membrane potential, intracellular reactive oxygen species (ROS) generation, the induction of cell apoptosis, and upregulation or downregulation of five apoptosis-related genes and proteins such as Bax, Bcl-2, caspases-3/-9, and cytochrome C, that cause cell apoptosis and growth suppression via the ROS-mediated mitochondrial pathway. SePPS2 consistently showed the highest capacity to exert these observed effects on the targeted cells, suggesting that the performed chemical selenylation of PPS (in particular when higher degrees of selenylation are reached) resulted in an increase in activity in the cells. It can thus be concluded that the performed selenylation of PPS was able to incorporate inorganic Se into the final PPS products, changing their monosaccharide composition and endowing them with enhanced nutraceutical and anti-cancer effects in the colon.

The Barrier-Enhancing Function of Soluble Yam (Dioscorea opposita Thunb.) Polysaccharides in Rat Intestinal Epithelial Cells as Affected by the Covalent Se Conjugation.

The non-starch yam polysaccharides (YP) are the bioactive substances of edible yam, while Se is an essential nutrient for the human body. Whether a covalent conjugation of Se to YP might cause bioactivity change for the resultant selenylated YP in the intestine is still insufficiently studied, including the critical intestinal barrier function. In this study, two selenylated YP products, namely, YPSe-I and YPSe-II, with corresponding Se contents of 795 and 1480 mg/kg, were obtained by the reaction of YP and Na2SeO3 in the presence of HNO3 and then assessed for their bioactivities to a cell model (i.e., rat intestinal epithelial IEC-6 cells). The results showed that YP, YPSe-I, and YPSe-II at 5-80 µg/mL dosages could promote cell growth with treatment times of 12-24 h. The three samples also could improve barrier integrity via increasing cell monolayer resistance and anti-bacterial activity against E. coli or by reducing paracellular permeability and bacterial translocation. Additionally, the three samples enhanced F-actin distribution and promoted the expression of the three tight junction proteins, namely, zonula occluden-1, occludin, and claudin-1. Meanwhile, the expression levels of ROCK and RhoA, two critical proteins in the ROCK/RhoA singling pathway, were down-regulated by these samples. Collectively, YPSe-I and, especially, YPSe-II were more potent than YP in enhancing the assessed bioactivities. It is thus concluded that this chemical selenylation of YP brought about enhanced activity in the cells to promote barrier integrity, while a higher selenylation extent of the selenylated YP induced much activity enhancement. Collectively, the results highlighted the important role of the non-metal nutrient Se in the modified polysaccharides.

Monosaccharide composition and in vivo immuno-stimulatory potential of soluble yam (Dioscorea opposita Thunb.) polysaccharides in response to a covalent Se incorporation.

The present study aimed to investigate whether selenylation modification could affect compositional features and in vivo immuno-stimulatory potential of yam polysaccharides. In this study, the soluble yam mucilage polysaccharides (YPS) were prepared and selenylated in the HNO3-Na2SeO3 system, and two selenylated polysaccharide products, namely SeYPS-1 and SeYPS-2 with respective Se contents of 719 and 1585 mg/kg, were thus obtained. GC-MS analysis demonstrated that the compositional features of SeYPS-1 and SeYPS-2 were similar to those of YPS. Meanwhile, the immuno-stimulatory potential of the selenylated products, especially SeYPS-2, in the BALB/c mice model was higher than that of YPS, reflected by the elevated contents of serum immunoglobins and increased percentage of CD4+ splenic lymphocytes. It was thus confirmed that the selenylation did not change the composition of monosaccharides but endowed YPS with greater immuno-stimulation in the mice, while the higher extent of selenylation also caused a much enhanced immuno-stimulatory potential of SeYPS-2.

[Synthesis of seleno-polysaccharides from Lonicerae Japonicae Flos via microwave and its immunological activity].

In this study, the microwave-assisted method was used to synthesize seleno-polysaccharides from Lonicerae Japonicae Flos, and the optimal process conditions were optimized.Meanwhile, the immunological activity of seleno-polysaccharides from Lonicerae Japonicae Flos was investigated.The results showed that under the conditions of nitric acid concentration of 0.512%, reaction temperature of 70.0 ℃, microwave power of 600 W, reaction time of 44.0 min, and m(Na_2SeO_3)∶m(polysaccharides)=1.0, the selenium content of Lonicerae Japonicae Flos seleno-polysaccharides was 3.89 mg·g~(-1).The results of in vitro immunoassay showed that polysaccharides and seleno-polysaccharides from Lonicerae Japonicae Flos could promote the proliferation of mouse RAW264.7 macrophages as compared with the conditions in the normal group.Compared with Lonicerae Japonicae Flos polysaccharides, Lonicerae Japonicae Flos seleno-polysaccharides could significantly facilitate the proliferation of mouse RAW264.7 macrophages and promote the production of IL-1ß and TNF-α at the concentration of 20-160 µg·mL~(-1).This study provided references for broadening the application of polysaccharides from Lonicerae Japonicae Flos.

Activities of the soluble and non-digestible longan (Dimocarpus longan Lour.) polysaccharides against HCT-116 cells as affected by a chemical selenylation.

The soluble and non-digestible longan (Dimocarpus longan Lour.) polysaccharides (LP) with Se content less than 0.01 g/kg were extracted and selenylated chemically with the HNO3-Na2SeO3 system, to prepare two selenylated products namely SeLP1 and SeLP2 with enhanced Se contents of 1.46 and 4.79 g/kg, respectively. LP, SeLP1, and SeLP2 were then measured and compared for their saccharide features and bioactivity in human colon carcinoma HCT-116 cells. Compared with LP, both SeLP1 and SeLP2 contained more neutral saccharides, but showed reduced uronic acid content and undetectable sulfate. Moreover, SeLP1 and especially SeLP2 in the cells showed higher activities than LP, reflected by their enhanced capacity to inhibit cell growth, alter cell morphology, and suppress cell colony formation. Compared with LP, SeLP1 and especially SeLP2 were also more capable of promoting intracellular reactive oxygen species and Ca2+ levels, causing mitochondrial membrane potential loss, or inducing cell apoptosis via up- and down-regulating the eight apoptosis-related genes and proteins. Overall, the performed chemical selenylation of LP resulted in obvious changes in these saccharide features and simultaneously enhanced the anti-cancer activity of the selenylated products against the cells clearly, while a higher selenylation extent of the selenylated products consistently caused higher activity towards the cells. The results of this study thus highlighted that this chemical selenylation is applicable when aiming to enhance the bioactivities of natural polysaccharides.

Flower-like MOF-74 nanocomposites directed by selenylation towards high-efficient oxygen evolution.

Sluggish kinetics of the oxygen evolution reaction during the water splitting requires high-performance electrocatalysts with low cost and good stability. Metal-organic frameworks (MOFs) have attracted much attention as electrocatalysts owing to their unique properties. To improve their electrocatalytic activity and stability, we report a selenylation method to modulate the morphology and interfaces by forming flower-like MOF-selenide nanocomposites. The optimal sample exhibits high activity with an overpotential of 260 mV at 10 mA cm-2, much better than commercial RuO2 and the control samples. Moreover, the optimal sample has the lowest Tafel slope of 54.3 mV dec-1, indicating the fast reaction kinetics, which can be attributed to the lower charge-transfer resistance and high intrinsic activity. Chronoamperometry shows that the optimal sample can maintain the current density for 60 h at 10 mA cm-2 after the initial surface reconstruction, demonstrating good stability. This study provides a new perspective on the development of highly efficient electrocatalysts based on polymetallic MOFs.

Selenylation Chemistry Suitable for On-Plate Parallel and On-DNA Library Synthesis Enabling High-Throughput Medicinal Chemistry.

Click chemistry is a concept wherein modular synthesis is used for rapid functional discovery. To this end, continuous discovery of clickable chemical transformations is the pillar to support the development of this field. This report details the development of a clickable C3-H selenylation of indole that is suitable for on-plate parallel and DNA-encoded library (SeDEL) synthesis via bioinspired LUMO activation strategy. This reaction is modular, robust and highly site-selective, and it features a simple and mild reaction system (catalyzed by nonmetallic B(C6 F5 )3 at room temperature), high yields and excellent functional group compatibility. Using this method, a library of 1350 indole-selenides was parallel synthesized in an efficient and practical manner, enabling the rapid identification of 3 ai as a promising compound with nanomolar antiproliferative activity in cancer cells via in situ phenotypic screening. These results indicate the great potential of this new clickable selenylation reaction in high-throughput medicinal chemistry and chemical biology.

Enhanced Growth Inhibition and Apoptosis Induction in Human Colon Carcinoma HT-29 Cells of Soluble Longan Polysaccharides with a Covalent Chemical Selenylation.

The selenylated polysaccharides chemically belong to the organic Se-conjugated macromolecules and have recently been attracting more and more attention due to their potential to promote body health or prevent cancers. Longan (Dimocarpus longan L.), as a subtropical fruit, contains soluble and non-digestible polysaccharides that are regarded with health care functions in the body. In this study, the longan polysaccharides (LP) were obtained via enzyme-assisted water extraction, and then chemically selenylated using a reaction system composed of HNO3-Na2SeO3 to yield two selenylated products, namely, SeLP1 and SeLP2, with Se contents of 1.46 and 4.79 g/kg, respectively. The anti-cancer effects of the three polysaccharide samples (LP, SeLP1, and SeLP2) were thus investigated using the human colon cancer HT-29 cells as the cell model. The results showed that SeLP1 and SeLP2 were more able than LP to inhibit cell growth, alter cell morphology, cause mitochondrial membrane potential loss, increase intracellular reactive oxygen and [Ca2+]i levels, and induce apoptosis via regulating the eight apoptosis-related genes and proteins including Bax, caspases-3/-8/-9, CHOP, cytochrome c, DR5, and Bcl-2. It was thereby proven that the selenylated polysaccharides could induce cell apoptosis via activating the death receptor, mitochondrial-dependent, and ER stress pathways. Collectively, both SeLP1 and SeLP2 showed higher activities than LP in HT-29 cells, while SeLP2 was consistently more active than SeLP1 in exerting these assessed anti-cancer effects on the cells. In conclusion, this chemical selenylation covalently introduced Se into the polysaccharide molecules and caused an enhancement in their anti-cancer functions in the cells, while higher selenylation extent was beneficial to the activity enhancement of the selenylated products.

Immunostimulatory and antioxidant activities of the selenized polysaccharide from edible Grifola frondosa.

Grifola frondosa polysaccharide (GFP2) was extracted and purified by anion-exchange chromatography. A selenized G. frondosa polysaccharide, SeGFP2, was modified in selenylation by nitric acid-sodium selenite (HNO3-Na2SeO3) method. Structural features were investigated, and the lymphocyte proliferation and antioxidant activities were compared taking GFP2 as control. SeGFP2 with a molecular weight of 2.12 × 104 Da was composed of mannose, glucose, and galactose with a ratio of 3.5:11.8:1.0. A typical absorption of selenium ester was observed in SeGFP2 molecule. SeGFP2 was proposed as a branched polysaccharide, which consisted of 1,3-D-Glcp, 1,6-D-Glcp, 1,4,6-D-Galp, and 1,3,6-D-Manp. SeGFP2 showed a linear filamentous structure with some branches. SeGFP2 could significantly promote T- or B-lymphocyte proliferation and the enhancement was higher than GFP2. The in vitro antioxidant activities of SeGFP2 were more potent than GFP2. These present data suggested that selenylation could significantly improve the lymphocyte proliferation and in vitro antioxidant activities of GFP2.

Characterization, antioxidant, antineoplastic and immune activities of selenium modified Sagittaria sagittifolia L. polysaccharides.

This study proposed an optimal way to supplement organic selenium, boost polysaccharides solubility, antioxidant, anticancer, immune responses. A purified polysaccharide fraction of Sagittaria sagittifolia L. (PSSP) was successfully modified with selenium (Se-PSSP), and its characteristics, antioxidant, antineoplastic and immune activities were studied. The structure and the monosaccharide composition were determined by means of UV-visible spectrometry, FT-IR spectra, NMR spectra, X-ray diffraction spectroscopy (XRD), scanning electron microscope (SEM) and atomic force microscope (AFM). The results showed that both PSSP and Se-PSSP contained a pyranoid polysaccharide linked by α-glycosidic bonds in the main chain. In addition, PSSP and Se-PSSP were amorphous morphology without three-helix conformation. PSSP (47.12 kDa) was mainly composed of glucose, mannose and xylose with molar percentages of 55.82%, 14.86% and 14.35%, respectively. Se-PSSP (16.82 kDa) is mainly composed of glucose, xylose and galactose with molar percentages of 26.49%, 18.76% and 18.14%, respectively. Compared with PSSP, Se-PSSP showed stronger water-solubility, antioxidant activity, cytotoxicity and immunomodulatory activity than that of PSSP. These results suggested that Se-PSSP is a promising novel Se-supplement and may be served as an excellent potential antioxidant, antineoplastic, and immunomodulatory agents in the field of functional foods and medicine industry.

Effects of selenylation modification on the antioxidative and immunoregulatory activities of polysaccharides from the pulp of Rose laevigata Michx fruit.

Selenylation modification has been widely utilized to improve the activity of polysaccharides and to develop novel sources of selenium (Se) supplements. A purified pulp polysaccharide of Rose laevigata Michx fruit (PPRLMF-2) was selenized into Se-PPRLMF-2 in this study. PPRLMF-2 + Se was formulated by Na2SeO3 according to the Se content of Se-PPRLMF-2. To investigate the effects of selenylation modification on the structure and functions of PPRLMF-2, the characteristics, antioxidative and immunoregulatory activities of PPRLMF-2 before and after selenylation were compared. The results showed that compared with PPRLMF-2, Se-PPRLMF-2 became an irregular fibrous network, and its Mw decreased and C-6 substitution predominated in 13C NMR spectra. Se-PPRLMF-2 significantly increased chemical antioxidant activity and reduced the oxidative damage of erythrocytes, which was not due to Se alone. Se-PPRLMF-2 significantly increased immunomodulatory activity on macrophages, which was related to Se alone. Se-PPRLMF-2 could be a good potential source of antioxidants, immune enhancers and dietary Se supplements.

Preparation and structural properties of selenium modified heteropolysaccharide from the fruits of Akebia quinata and in vitro and in vivo antitumor activity.

Cancer is a complex disease, and blocking tumor angiogenesis has become one of the most promising approaches in cancer therapy. Here, an exopoly heteropolysaccharide (AQP70-2B) was firstly isolated from Akebia quinata. Monosaccharide composition indicated that the AQP70-2B was composed of rhamnose, glucose, galactose, and arabinose. The backbone of AQP70-2B consisted of →1)-l-Araf, →3)-l-Araf-(1→, →5)-l-Araf-(1→, →3,5)-l-Araf-(1→, →2,5)-l-Araf-(1→, →4)-d-Glcp-(1→, →6)-d-Galp-(1→, and →1)-d-Rhap residues. Based on the close relationship between selenium and anti-tumor activity, AQP70-2B was modified with selenium to obtain selenized polysaccharide Se-AQP70-2B. Then, a series of methods for analysis and characterization, especially scanning electron microscopy coupled with energy dispersive spectrometry (SEM-EDS), indicated that Se-AQP70-2B was successfully synthesized. Furthermore, zebrafish xenografts and anti-angiogenesis experiments indicated that selenization could improve the antitumor activity by inhibiting tumor cell proliferation and migration and blocking angiogenesis.

Supplementary selenium in the form of selenylation α-D-1,6-glucan ameliorates dextran sulfate sodium induced colitis in vivo.

The deficiency of selenium has been found in clinical IBD patients and supplementation selenium is recognized as beneficial for colitis treatment. In this study, an organic selenium compound-selenylation α-D-1,6-glucan (sCPA) was prepared, and the effect of sCPA on DSS induced colitis mice was investigated. The results suggested that sCPA prevented the weight loss, colon length shortening, and stool loose of colitis mice. It protected colon mucosal barrier by promoting tight junction protein ZO-1 and Occludin expression. Moreover, sCPA reduced oxidative stress via regulating SOD and MDA levels, and decreased the contents of inflammatory proteins NF-κB and NLRP3 and adjusted TNF-α, IFN-γ, IL-1ß, and IL-10 inflammatory cytokines. Furthermore, sCPA repaired intestinal microbiota composition especially Bacteroidetes, Firmicutes, Proteobacteria, and Actinobacteria that altered by DSS in colitis mice. Meanwhile, SCFAs produced by gut microbiota were restored by sCPA close to the level in the normal group. In conclusion, these findings indicated that the sCPA might be a potential dietary selenium supplementation for the prevention and treatment of colitis.