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Extraction, Isolation, Structural Characterization and Anti-Tumor Properties of an Apigalacturonan-Rich Polysaccharide from the Sea Grass Zostera caespitosa Miki.

Lv Y, Shan X, Zhao X, Cai C, Zhao X, Lang Y, Zhu H, Yu G - Mar Drugs (2015)

Bottom Line: The anti-angiogenesis assay showed that ZCMP inhibited the migratory activity of human umbilical vein endothelial cell (HUVECs), with no influence on endothelial cells growth.ZCMP also promoted macrophage phagocytosis.These findings of the present study demonstrated the potential anti-tumor activity of ZCMP through anti-angiogenic and immunoregulatory pathways.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. lvyoujing1988@163.com.

ABSTRACT
An apigalacturonan (AGA)-rich polysaccharide, ZCMP, was isolated from the sea grass Zostera caespitosa Miki. The depolymerized fragments derived from ZCMP were obtained by either acidic degradation or pectinase degradation, and their structures were characterized by electrospray ionization collision-induced-dissociation mass spectrometry (ESI-CID-MS2) and nuclear magnetic resonance (NMR) spectroscopy. The average molecular weight of ZCMP was 77.2 kD and it consisted of galacturonic acid (GalA), apiosefuranose (Api), galactose (Gal), rhamnose (Rha), arabinose (Ara), xylose (Xyl), and mannose (Man), at a molar ratio of 51.4꞉15.5꞉6.0꞉11.8꞉4.2꞉4.4꞉4.2. There were two regions of AGA (70%) and rhamnogalacturonan-I (RG-Ι, 30%) in ZCMP. AGA was composed of an α-1,4-D-galactopyranosyluronan backbone mainly substituted at the O-3 position by single Api residues. RG-Ι possessed a backbone of repeating disaccharide units of →4GalAα1,2Rhaα1→, with a few α-L-arabinose and β-D-galactose residues as side chains. The anti-angiogenesis assay showed that ZCMP inhibited the migratory activity of human umbilical vein endothelial cell (HUVECs), with no influence on endothelial cells growth. ZCMP also promoted macrophage phagocytosis. These findings of the present study demonstrated the potential anti-tumor activity of ZCMP through anti-angiogenic and immunoregulatory pathways.

No MeSH data available.


Related in: MedlinePlus

1D NMR spectra of ZCMP-SS. Spectral analysis was performed at 25 °C on a JEOL ECP 600 MHz spectrometer using acetone as internal standard. (a) 1H NMR spectrum and (b) 13C NMR and DEPT spectra.
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marinedrugs-13-03710-f008: 1D NMR spectra of ZCMP-SS. Spectral analysis was performed at 25 °C on a JEOL ECP 600 MHz spectrometer using acetone as internal standard. (a) 1H NMR spectrum and (b) 13C NMR and DEPT spectra.

Mentions: The structural features of ZCMP-SS were also characterized by using a combination of one-dimensional 1H NMR, 13C NMR, and Distortionless Enhancement by Polarization Transfer (DEPT) experiments (Figure 8), as well as heteronuclear two-dimensional 1H-13C Heteronuclear Multiple Quantum Coherence (HMQC) experiment. The proton-carbon correlation was assigned based on the HMQC spectrum (Figure 9), and seven cross peaks corresponding to the anomeric signals were clearly detected. Correlations between H1 at 5.24 ppm and C1 at 104.70 ppm, H1 at 5.33 ppm and C1 at 97.60 ppm, H1 at 5.54 ppm and C1 at 99.18 ppm, and H1 at 5.27 ppm and C1 at 103.08 ppm were assigned to α-l-Apif, α-d-Apif, β-l-Apif, and β-d-Apif respectively [10,31]. Its molar ratio was determined to be 1.0:3.0:4.0:1.3, based on the integral area ratio detected in 1H-NMR. No correlations of Api oligosaccharides in the side chains were detected due to its instability under acidic conditions. The anomeric proton signals of linked α-l-Ara and terminal α-l-Ara residues at 5.05 ppm and 5.02 ppm were correlated to the anomeric carbon signals at 110.1 ppm and 109.80 ppm, respectively. The correlation of H1 at 4.76 ppm with C1 at 101.44 ppm was assigned to β-d-Gal residues.


Extraction, Isolation, Structural Characterization and Anti-Tumor Properties of an Apigalacturonan-Rich Polysaccharide from the Sea Grass Zostera caespitosa Miki.

Lv Y, Shan X, Zhao X, Cai C, Zhao X, Lang Y, Zhu H, Yu G - Mar Drugs (2015)

1D NMR spectra of ZCMP-SS. Spectral analysis was performed at 25 °C on a JEOL ECP 600 MHz spectrometer using acetone as internal standard. (a) 1H NMR spectrum and (b) 13C NMR and DEPT spectra.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4483652&req=5

marinedrugs-13-03710-f008: 1D NMR spectra of ZCMP-SS. Spectral analysis was performed at 25 °C on a JEOL ECP 600 MHz spectrometer using acetone as internal standard. (a) 1H NMR spectrum and (b) 13C NMR and DEPT spectra.
Mentions: The structural features of ZCMP-SS were also characterized by using a combination of one-dimensional 1H NMR, 13C NMR, and Distortionless Enhancement by Polarization Transfer (DEPT) experiments (Figure 8), as well as heteronuclear two-dimensional 1H-13C Heteronuclear Multiple Quantum Coherence (HMQC) experiment. The proton-carbon correlation was assigned based on the HMQC spectrum (Figure 9), and seven cross peaks corresponding to the anomeric signals were clearly detected. Correlations between H1 at 5.24 ppm and C1 at 104.70 ppm, H1 at 5.33 ppm and C1 at 97.60 ppm, H1 at 5.54 ppm and C1 at 99.18 ppm, and H1 at 5.27 ppm and C1 at 103.08 ppm were assigned to α-l-Apif, α-d-Apif, β-l-Apif, and β-d-Apif respectively [10,31]. Its molar ratio was determined to be 1.0:3.0:4.0:1.3, based on the integral area ratio detected in 1H-NMR. No correlations of Api oligosaccharides in the side chains were detected due to its instability under acidic conditions. The anomeric proton signals of linked α-l-Ara and terminal α-l-Ara residues at 5.05 ppm and 5.02 ppm were correlated to the anomeric carbon signals at 110.1 ppm and 109.80 ppm, respectively. The correlation of H1 at 4.76 ppm with C1 at 101.44 ppm was assigned to β-d-Gal residues.

Bottom Line: The anti-angiogenesis assay showed that ZCMP inhibited the migratory activity of human umbilical vein endothelial cell (HUVECs), with no influence on endothelial cells growth.ZCMP also promoted macrophage phagocytosis.These findings of the present study demonstrated the potential anti-tumor activity of ZCMP through anti-angiogenic and immunoregulatory pathways.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. lvyoujing1988@163.com.

ABSTRACT
An apigalacturonan (AGA)-rich polysaccharide, ZCMP, was isolated from the sea grass Zostera caespitosa Miki. The depolymerized fragments derived from ZCMP were obtained by either acidic degradation or pectinase degradation, and their structures were characterized by electrospray ionization collision-induced-dissociation mass spectrometry (ESI-CID-MS2) and nuclear magnetic resonance (NMR) spectroscopy. The average molecular weight of ZCMP was 77.2 kD and it consisted of galacturonic acid (GalA), apiosefuranose (Api), galactose (Gal), rhamnose (Rha), arabinose (Ara), xylose (Xyl), and mannose (Man), at a molar ratio of 51.4꞉15.5꞉6.0꞉11.8꞉4.2꞉4.4꞉4.2. There were two regions of AGA (70%) and rhamnogalacturonan-I (RG-Ι, 30%) in ZCMP. AGA was composed of an α-1,4-D-galactopyranosyluronan backbone mainly substituted at the O-3 position by single Api residues. RG-Ι possessed a backbone of repeating disaccharide units of →4GalAα1,2Rhaα1→, with a few α-L-arabinose and β-D-galactose residues as side chains. The anti-angiogenesis assay showed that ZCMP inhibited the migratory activity of human umbilical vein endothelial cell (HUVECs), with no influence on endothelial cells growth. ZCMP also promoted macrophage phagocytosis. These findings of the present study demonstrated the potential anti-tumor activity of ZCMP through anti-angiogenic and immunoregulatory pathways.

No MeSH data available.


Related in: MedlinePlus