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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

Negative-ion ESI-CID-MS2 product-ion spectra of the tetrasaccharide Api4 from ZCMP-S. (a) Sequence analysis of the tetrasaccharide Api4 at m/z 545; (b) Sequence analysis of the tetrasaccharide alditol at m/z 547.
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marinedrugs-13-03710-f004: Negative-ion ESI-CID-MS2 product-ion spectra of the tetrasaccharide Api4 from ZCMP-S. (a) Sequence analysis of the tetrasaccharide Api4 at m/z 545; (b) Sequence analysis of the tetrasaccharide alditol at m/z 547.

Mentions: A series of Api-oligosaccharides was released from ZCMP after CH3COOH hydrolysis and the ESI-CID-MS2 spectra of di-, tri- and hexa-saccharides were detected. The results demonstrated that all of them possessed the same fragment ion pattern. Taking the product-ion spectrum of Api4 (m/z 545) as an example (Figure 4), a series of ions of glycosidic bond cleavage at m/z 263 (B2/Y2), 281 (C2/Z2), 395 (B3/Y3) and 413 (C3/Z3) indicated a linear chain. In addition, a series of notably 2,3A type ions (m/z 191, 323, 455) were generated by cross-cleavage of the C2-C3 and C3-C4 bonds of Api, which in turn led to the loss of C3H6O3 of m/z 90. The ion at m/z 485 was deduced as 1,3A4 or 0,2A4 cleavage. Similarly, the ion at m/z 353 was deduced as 1,3A3 or 0,2A3 cleavage. Guo et al. [25] also determined a series of linear oligo-galatofuranoses by negative-ion ESI-CID-MS2. Cross-ring fragment ions of 3,4A and 0,3A-type fragment ions were observed as well and used in the identification of linkages between the β-D-(1→5)-linked Galf oligosaccharides. Based on the proposed similar ion pattern of fragments, the linkage between Api residues was deduced to be 3′-linked. After reduction (Figure 4b), four glycosidic ions of tetrasaccharide Api4 shifted to m/z 415 (Z3), 397 (Y3), 283 (Z2) and 265 (Y2) from m/z 413, 395, 281 and 263, respectively. No cross-ring cleavage ions shifted after reduction, suggesting that all of these were produced from the non-reducing end.


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)

Negative-ion ESI-CID-MS2 product-ion spectra of the tetrasaccharide Api4 from ZCMP-S. (a) Sequence analysis of the tetrasaccharide Api4 at m/z 545; (b) Sequence analysis of the tetrasaccharide alditol at m/z 547.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-03710-f004: Negative-ion ESI-CID-MS2 product-ion spectra of the tetrasaccharide Api4 from ZCMP-S. (a) Sequence analysis of the tetrasaccharide Api4 at m/z 545; (b) Sequence analysis of the tetrasaccharide alditol at m/z 547.
Mentions: A series of Api-oligosaccharides was released from ZCMP after CH3COOH hydrolysis and the ESI-CID-MS2 spectra of di-, tri- and hexa-saccharides were detected. The results demonstrated that all of them possessed the same fragment ion pattern. Taking the product-ion spectrum of Api4 (m/z 545) as an example (Figure 4), a series of ions of glycosidic bond cleavage at m/z 263 (B2/Y2), 281 (C2/Z2), 395 (B3/Y3) and 413 (C3/Z3) indicated a linear chain. In addition, a series of notably 2,3A type ions (m/z 191, 323, 455) were generated by cross-cleavage of the C2-C3 and C3-C4 bonds of Api, which in turn led to the loss of C3H6O3 of m/z 90. The ion at m/z 485 was deduced as 1,3A4 or 0,2A4 cleavage. Similarly, the ion at m/z 353 was deduced as 1,3A3 or 0,2A3 cleavage. Guo et al. [25] also determined a series of linear oligo-galatofuranoses by negative-ion ESI-CID-MS2. Cross-ring fragment ions of 3,4A and 0,3A-type fragment ions were observed as well and used in the identification of linkages between the β-D-(1→5)-linked Galf oligosaccharides. Based on the proposed similar ion pattern of fragments, the linkage between Api residues was deduced to be 3′-linked. After reduction (Figure 4b), four glycosidic ions of tetrasaccharide Api4 shifted to m/z 415 (Z3), 397 (Y3), 283 (Z2) and 265 (Y2) from m/z 413, 395, 281 and 263, respectively. No cross-ring cleavage ions shifted after reduction, suggesting that all of these were produced from the non-reducing end.

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