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Plants are known to be a great source of phytochemicals for centuries. Medicago, belonging to the Family Fabaceae, is a large and well spread genus comprising about 83 cosmopolitan species, of which one-third are annuals and span diverse ecological niches. Medicago species are rich in saponins mainly classified into three classes, namely, steroid alkaloid glycosides, triterpene glycosides, and steroid glycosides. These saponins are important compounds having diverse pharmacological and biological activities. As a whole, 95 of saponins are reported to date occurring in Medicago species using various latest extraction/isolation techniques. Considering the multiple biological and pharmacological potential of Medicago species due to saponins along with structural diversity, we compiled this review article to sum up the recent reports for the pharmacological potential of the Medicago's derived saponins in modern as well as traditional medication systems. The current manuscript produces data of chemical structures and molecular masses of all Medicago species saponins simultaneously. The toxicity of certain pure saponins (aglycones) has been reported in vitro; hederagenin appeared highly toxic in comparison to medicagenic acid and bayogenin against X. index, while soyasaponin I, containing soyasapogenol B as a glycone, appeared as the least toxic saponin. The diversity in the structural forms shows a close relationship for its biological and pharmacological actions. Moreover, saponins showed antioxidant properties and the mechanism behind antimicrobial potential also elaborated in this review article is mainly because of the side sugar groups on these compounds. The collected data presented herein include chemical structures and molecular masses of all saponins so far. Their biological activity and therapeutic potential are also discussed. This information can be the starting point for future research on this important genus. [ABSTRACT FROM AUTHOR]

Phosphorylation is a key route to achieve varieties of biological activities for polysaccharides. Currently, conventional phosphorylation reagents are characterized by long processing times and high reaction temperatures. Here, we reported phosphorylation of Artemisia sphaerocephala polysaccharides (PASP) with the degrees of substitution (DS) of 0.34-0.54 in mild reaction conditions (3–4 h and 25 °C) by employing POCl 3 /pyridine technique. FT-IR spectroscopy and X-ray photoelectron spectroscopy (XPS) analysis confirmed the appearance of phosphate ester (P 5+ ) groups in PASP. Size exclusion chromatography combined with multi-angle laser light scattering (SEC-MALLS) result clearly showed temperature-dependent increment of weight average molecular mass ( M W ). High temperature facilitated the reaction of phosphoryl chloride with primary and secondary hydroxyl groups, favoring the crosslinking of polysaccharide chains by phosphate di-esters as further confirmed in 13 C NMR determination. Our results provide insight into the relationship between the structure and reaction conditions of phosphorylated polysaccharide, which is important for understanding and exploiting these derivatives in a wide range of applications. [ABSTRACT FROM AUTHOR]

In this work, selenylation of Artemisia sphaerocephala polysaccharide (SeASP MW ) was studied by using H 2 SeO 3 /HNO 3 /BaCl 2 reaction system in microwave field. SeASP MW exhibited the Se content range of 111–264 μg/g with high yields (72.1–94.9%). 13 C NMR results indicated that the weak C-6 substitution was occurred. The decrease (from 7.348 × 10 4 g/mol to 1.736–4.667 × 10 4 g/mol) in weight average molecular mass ( M W ) of SeASP MW was observed in size exclusion chromatography combined with multi angle laser light scattering (SEC-MALLS) analysis. SeASP MW exhibited a more rigid solution conformation which might be due to the degradation of polysaccharide chains in acidic reaction reagent. This was also supported by atomic force microscopy (AFM) result that SeASP MW showed short chains and island-like topography. In anti-tumor activity assays, SeASP MW6 exhibited the inhibition rates of 32.381% and 39.776% against human non-small cell lung cancer cell line (H1650) at the concentration of 100 and 200 μg/mL, respectively. The relatively weak inhibition effect of SeASP MW was not related to cell apoptosis and cell cycle arrest, suggesting Se content might be a key factor to influence the anti-tumor activities of selenized polysaccharides in vitro . [ABSTRACT FROM AUTHOR]

Sulfated derivatives of galactomannan from locust bean gum (LBG) with the degree of substitution (DS) of 0.34–1.07 were synthesized using chlorosulfonic acid/pyridine (CSA/Py) method. Box–Behnken design (BBD) of response surface methodology (RSM) was employed to optimize the reaction conditions. Results of FT-IR and X-ray photoelectron spectroscopy (XPS) indicated that SO 3 H groups were widely present in sulfated LBG (SLBG). 13 C NMR result revealed that sulfation had occurred and C-6 substitution was predominant in SLBG. All sulfated samples showed a decrease in M w and more broad molar mass distribution in size exclusion chromatography combined with laser light scattering (SEC-LLS) analysis. Results of M W – 〈 S 2 〉 z 1 / 2 showed a decrease in fractal dimension ( d f ) value. Laser light scattering results also showed a conformation transition from a compact chain conformation of branched clusters to a random coil conformation of SLBG. Compared to LBG and SLBG with low DS and molecular weight, SLBG 2 exhibited an internal structure of random coil with a DS of 1.07. DS and molecular weight had great influence on its conformation in aqueous solution. Our results confirmed that the degradation of polysaccharide and SO 3 H groups improved significantly the stiffness of the chains due to the electrostatic effect. [ABSTRACT FROM AUTHOR]

Abstract: We reported here a new synthesis of C-2 and C-3 sulfated guar gum (SRSGG) with low degree of substitution (DSS) of 0.58, employing triphenylchloromethane (TrCl) as a protected precursor. The yield and DSTr (calculated from the weight of triphenylmethanol) of triphenylmethylated GG (GGTr) was 165.6% and 0.71, respectively. In addition, low ratio (1:4) of chlorosulfuric acid to pyridine (1:4) was chosen in sulfation reaction since the protecting group was slightly sensitive to acid. Results of FT-IR and 13C NMR spectroscopy indicated that C-2 and C-3 substitution was predominant but not fully sulfated in SRSGG. Size-exclusion chromatograph combined with multi-angle laser photometer (SEC-LLS) showed a decrease in molecular weight in the reaction. This might be due to the degradation in sulfation and deprotection process. Finally, we investigated the effect of structure features on the antioxidant activities in vitro. Vitro antioxidant experiments revealed that the regioselective sulfation at C-2 and C-3 and low molecular weight afforded strong antioxidant activities showing a much higher scavenging abilities of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical than that by the known C-6-sulfated derivative. The antioxidant activities of sulfated polysaccharides were not a function of a single factor but a combination of molecular weight, DSS and substitution positions. [Copyright &y& Elsevier]

Abstract: It was essential to understand the chemical structure of polysaccharides for further research and biochemical or medical application of this natural biopolymer. In the present study, sulfated derivatives of guar gum with high degree of sulfation (DS) were synthesized using 4-dimethylaminopyridine (DMAP)/dimethylcyclohexylcarbodiimide (DCC) as catalyst in homogeneous conditions. The effects of the ratio of chlorosulfuric acid to pyridine, the content of catalyst and reaction temperature were investigated. Results of FT-IR, 1H and 13C NMR indicated that C-6 substitution was predominant in sulfated polysaccharide. In the sulfation reaction, a sharp decrease in M W was observed. The enhanced antioxidant activities of sulfated polysaccharides were not a function of a single factor but a combination of high DS and low molecule weight. [Copyright &y& Elsevier]

Abstract: Sulfated polysaccharides exerted potent biological property which was relative to degree of sulfation (DS), M w, substitution position and chain conformation. In the present study, sulfated derivatives of Artemisia sphaerocephala polysaccharide (ASP) with different DS were synthesized by chlorosulfuric acid/pyridine method. FT-IR and 13C NMR analysis indicated that C-6 substitution was predominant in sulfated ASP (SASP) compared with other positions at C-2. In the sulfation reaction, a sharp decrease in M w was observed in SASP. The d f values from 1.96 to 2.77 indicated that the –SO3H groups leading to the relatively expanded conformation of SASP. Antioxidant assays showed that SASP had better antioxidant activities. The data obtained in vitro models indicated that high DS and moderate M w showed the best antioxidant capacities. [Copyright &y& Elsevier]

Abstract: A water-soluble polysaccharide isolated from Cynomorium songaricum which is a traditional Chinese food was purified by Ultrahydrogel 500 gel filtration chromatography. The structural characterisation and hypoglycaemic activity of the purified polysaccharide fraction (CSPA) were evaluated. CSPA (Mw of 1.394×105 Da) was a heteropolysaccharide consisting of Ara, Glu and Gal. The conformation of CSPA was characterised as a compact chain of sphere-like structure in aqueous solution with a df value of 2.86. Linkage analysis and NMR (1D and 2D) revealed the presence of the following unit:. Pharmaceutical experiments showed that the administration of CSPA could significantly decrease blood glucose levels, glutamic oxaloacetic transaminase, glutamic pyruvic transaminase, blood urea nitrogen, creatinine activities, and effectively increase serum insulin level and the content of liver glycogen in streptozotocin-induced diabetic rats. Histopathology studies showed that the reduced islet cells were restored to near normal upon treatment with CSPA. The results suggest CSPA could be considered as a potential candidate for developing a new anti-diabetic agent. [Copyright &y& Elsevier]

Abstract: Sulfated polysaccharides exerted potential biological property which was relative to degree of sulfation (DS), M w, substitution position and chain conformation. In the present study, commercial guar gum was purified and its sulfated derivates with different DS and M w were synthesized. FT-IR and 13C NMR analysis indicated that C-6 substitution was predominant in sulfated samples compared with other positions. In the sulfation reaction, a sharp decrease in M w was observed. The d f values from 1.92 to 2.85 indicated that the –SO3H groups led to the relatively expanded conformation of sulfated polysaccharides. Antioxidant assays showed that sulfated polysaccharides had better antioxidant activities. The data obtained in in vitro models indicated that high DS and low M w showed the best antioxidant capacities. [Copyright &y& Elsevier]

Abstract: The conventional extraction methods for polysaccharides were time-consuming, laborious and energy-consuming. Microwave-assisted extraction (MAE) technique was employed for the extraction of Artemisia sphaerocephala polysaccharides (ASP), which is a traditional Chinese food. The extracting parameters were optimized by Box-Behnken design. In microwave heating process, a decrease in molecular weight (M w) was detected in SEC-LLS measurement. A d f value of 2.85 indicated ASP using MAE exhibited as a sphere conformation of branched clusters in aqueous solution. Furthermore, it showed stronger antioxidant activities compared with hot water extraction. The data obtained showed that the molecular weights played a more important role in antioxidant activities. [Copyright &y& Elsevier]

[Display omitted] • Surface modifying MIL-125(Ti) with functional organic molecular is a useful way. • The adsorption and visible light catalytic properties of the nanocomposite is obviously enhanced. • Calcination further improves the adsorption and photocatalytic performance. • TPE-2Py@DSMIL-125(Ti) has great applicability, reproducibility and stability. A multi-nitrogen conjugated organic molecule (TPE-2Py) was selected to surface modify the calcined MIL-125(Ti) to prepare a nanocomposite (TPE-2Py@DSMIL-125(Ti)) for adsorption and photodegradation of organic pollutant (tetracycline hydrochloride) under visible light. A novel reticulated surface layer was formed on the nanocomposite, and the adsorption capacity of TPE-2Py@DSMIL-125(Ti) for tetracycline hydrochloride can reach 157.7 mg/g under neutral conditions, which is higher than that of most other reported materials. Kinetic and thermodynamic studies show that the adsorption is a spontaneous heat absorption process, dominated by chemisorption, in which electrostatic interaction, π-π conjugation and Ti-N covalent bonds played dominant roles. The photocatalytic study shows that the visible photo-degradation efficiency of TPE-2Py@DSMIL-125(Ti) for tetracycline hydrochloride can further reach 89.1% after adsorption. Mechanism studies reveal that •O 2 − and h+ play a major role in the degradation process, and the separation and transfer rate of photo-generated carriers increase, improving its visible photocatalytic performance. This study revealed the relationship between the adsorption/photocatalytic properties of the nanocomposite and the structure of the molecular as well as the calcination, providing a convenient strategy to regulate the removal efficiency of MOFs materials towards organic pollutants. Furthermore, TPE-2Py@DSMIL-125(Ti) exhibits good reusability and even better removal efficiency for tetracycline hydrochloride in real water samples, indicating its sustainable treatment of pollutants in contaminated water. [ABSTRACT FROM AUTHOR]

Galactomannan stands as a promising heteropolysaccharide, yet its randomly distributed non-linear structures and high molecular mass remain a huge challenge in solubilization and wide range of chemical modifications. This work develops a task specific approach for efficient dissolve of galactomannan in ionic liquids (ILs) by destructing and reconstructing intermolecular/intramolecular hydrogen bonds of galactomannan. Combining density functional theory calculations and experimental results, a reasonable mechanism of polysaccharide dissolution is proposed that the hydrogen bond networks of polysaccharide are broken, thus the hydroxyl groups are fully exposed and activated to facilitate functionalization. In view of the enhanced solubilization, an excellent effect in selenylation of galactomannan is notably improved by employing ILs with dual roles as solvents and catalysts. Typically, the introduction of -SO 3 H in ILs (SFILs) effectively enhances the protonation ability of selenium donor and thus further improves the functionalization efficiency. Furthermore, a surprising finding is observed that selenium content and average molecular mass of functionalized polysaccharide can be manipulated by the anions-cations synergistic effect which is highly dependent on SFILs acidity strength. This work proposed an integrated and promising strategy for improving the solubilization and functionalization manipulating by ILs, showing a great referential value for the widespread application in polysaccharide-rich resources. [Display omitted] [ABSTRACT FROM AUTHOR]