Regioselective sulfation of Artemisia sphaerocephala polysaccharide: Characterization of chemical structure

In this work, selenylation of Artemisia sphaerocephala polysaccharide (SeASP) was studied by using HSeO/HNO/BaCl reaction system in microwave field. SeASP exhibited the Se content range of 111-264μg/g with high yields (72.1-94.9%). C NMR results indicated that the weak C-6 substitution was occurred. The decrease (from 7.348×10g/mol to 1.736-4.667×10g/mol) in weight average molecular mass (M) of SeASP was observed in size exclusion chromatography combined with multi angle laser light scattering (SEC-MALLS) analysis. SeASP 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 showed short chains and island-like topography. In anti-tumor activity assays, SeASP 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 200μg/mL, respectively. The relatively weak inhibition effect of SeASP 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.

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“…1B-1D. The assignment of the chemical shifts of ASP was shown in our previous study [29]. As shown in Fig.…”

Section: C Nmr Analysismentioning

confidence: 63%

Microwave-assisted synthesis, structure and anti-tumor activity of selenized Artemisia sphaerocephala polysaccharide

Wang

Yang

Bao

et al. 2017

International Journal of Biological Macromolecules

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“…A dramatically decrease in Man content was likely due to the acid hydrolysis of backbone during selenylation (Section 3.1). It had been shown by our earlier reports that the acidic hydrolysis with esterification reagent such as chlorosulfuric acid could be observed with the detection by means of SEC analysis (Wang et al, 2010;Wang et al, 2015).…”

Section: Analysis Of Monosaccharide Compositionmentioning

confidence: 91%

Synthesis of selenium-containing Artemisia sphaerocephala polysaccharides: Solution conformation and anti-tumor activities in vitro

Wang

Bao

et al. 2016

Carbohydrate Polymers

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It has been reported in our previous work that selenized Artemisia sphaerocephala polysaccharides (SeASPs) with the Se content range of 168-1703μg/g were synthesized by using Na2SeO3/HNO3/BaCl2 system. In the present work, the solution property of SeASP was studied by using size exclusion chromatography combined with multi angle laser light scattering (SEC-MALLS). A decrease in df values indicated that SeASPs with different conformational features that were highly dependent on MW. SeASPs exhibited a more rigid conformation (df value of 1.29-1.52) in low molecular weight range (MW of 1.026-1.426×10(4)g/mol) and compact spherical conformation in high molecular weight range (MW of 2.268-4.363×10(4)g/mol). It could be due to the degradation of polysaccharide chains in HNO3, which was supported in monosaccharide composition analysis. Congo red (CR) spectrophotometric method and atomic force microscopy (AFM) results also confirmed the conformational transition and the evidence on the shape of the rigid chains. In vitro anti-tumor assays, SeASP2 displayed greater anti-proliferative effects against three tumor cell lines (hepatocellular carcinoma HepG-2 cells, lung adenocarcinom A549 cells and cervical squamous carcinoma Hela cells) in a dose-dependent manner. This suggested that selenylation could significantly enhance the anti-tumor activities of polysaccharide derivatives in vitro.

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“…Monosaccharide composition analysis showed that ASP consists of arabinose, xylose, mannose, glucose and galactose (molar ratio of 1:4.2:45.9:9.7:11.4). The weight average molecular weight (M W ) and polydispersity (PD) of ASP was measured to be 7.348×10 4 Da and 3.184, respectively (Wang, et al, 2015). Sulfated Artemisia sphaerocephala polysaccharide (SASP) was prepared using chlorosulfuric acid/pyridine method.…”

Section: Artemisia Sphaerocephala Krasch Is Widely Distributed In Ganmentioning

confidence: 99%

“…The DS of S RS ASP varied from 0.44 to 0.63 with the substitution positions at C-2 and C-3. The chemical structure was characterized by FT-IR, XPS, 13 C NMR, GC-MS (monosaccharide composition) and size-exclusion chromatograph combined with multi-angle laser photometer (SEC-MALLS) analysis (Wang et al, 2015).…”

Section: Artemisia Sphaerocephala Krasch Is Widely Distributed In Ganmentioning

confidence: 99%

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Regioselective sulfation of Artemisia sphaerocephala polysaccharide: Solution conformation and antioxidant activities in vitro

Wang

Yang

Tang

et al. 2016

Carbohydrate Polymers

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Regioselective modification is an effective approach to synthesize polysaccharides with different structure features and improved properties. In this study, regioselective sulfation of Artemisia sphaerocephala polysaccharide (SRSASP) was prepared by using triphenylchloromethane (TrCl) as protecting precursor. The decrease in fractal dimension (df) values (1.56-2.04) of SRSASP was observed in size-exclusion chromatography combined with multi angle laser light scattering (SEC-MALLS) analysis. Compared to sample substituted at C-6, SRSASP showed a more expanded conformation of random coil, which was attributed to the breakup of hydrogen bonds and elastic contributions. Circular dichroism (CD), methylene blue (MB) and congo red (CR) spectrophotometric method and atomic force microscopy (AFM) results confirmed the conformational transition and stiffness of the chains after sulfation. SRSASP exhibited enhanced antioxidant activities in the DPPH, superoxide and hydroxyl radical scavenging assay. Sulfation at C-2 or C-3 was favorable for the chelation which might prevent the generation of hydroxyl radicals. It concluded that the degree of substitution and substitution position were the factors influencing biological activities of sulfated polysaccharides.

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Regioselective sulfation of Artemisia sphaerocephala polysaccharide: Characterization of chemical structure

Cited by 30 publications

References 27 publications

Microwave-assisted synthesis, structure and anti-tumor activity of selenized Artemisia sphaerocephala polysaccharide

Microwave-assisted synthesis, structure and anti-tumor activity of selenized Artemisia sphaerocephala polysaccharide

Synthesis of selenium-containing Artemisia sphaerocephala polysaccharides: Solution conformation and anti-tumor activities in vitro

Regioselective sulfation of Artemisia sphaerocephala polysaccharide: Solution conformation and antioxidant activities in vitro

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