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Structural analysis and anti-complement activity of polysaccharides from Kjellmaniella crsaaifolia.

Zhang W, Jin W, Sun D, Zhao L, Wang J, Duan D, Zhang Q - Mar Drugs (2015)

Bottom Line: The activity of KCA was found to be similar to KCW, suggesting that the method of extraction did not influence the activity.In addition, the degraded polysaccharides (DKCA and DKCW) displayed lower activity levels than the crude polysaccharides (KCA and KCW), indicating that molecular weight had an effect on activity.In conclusion, polysaccharides from K. crassifolia may be good candidates for the treatment of diseases involving the complement pathway.

View Article: PubMed Central - PubMed

Affiliation: Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China. wenjingwing@126.com.

ABSTRACT
Two polysaccharides, named KCA and KCW, were extracted from Kjellmaniella crassifolia using dilute hydrochloric acid and water, respectively. Composition analysis showed that these polysaccharides predominantly consisted of fucose, with galactose, mannose and glucuronic acid as minor components. After degradation and partial desulfation, electrospray ionization mass spectrometry (ESI-MS) was performed, which showed that the polysaccharides consisted of sulfated fucooligosaccharides, sulfated galactofucooligosaccharides and methyl glycosides of mono-sulfated/multi-sulfated fucooligosaccharides. The structures of the oligomeric fragments were further characterized by electrospray ionization collision-induced dissociation tandem mass spectrometry (ESI-CID-MS2 and ESI-CID-MS3). Moreover, the activity of KCA and KCW against the hemolytic activity of both the classical and alternative complement pathways was determined. The activity of KCA was found to be similar to KCW, suggesting that the method of extraction did not influence the activity. In addition, the degraded polysaccharides (DKCA and DKCW) displayed lower activity levels than the crude polysaccharides (KCA and KCW), indicating that molecular weight had an effect on activity. Moreover, the desulfated fractions (ds-DKCA and ds-DKCW) showed less or no activity, which confirmed that sulfate was important for activity. In conclusion, polysaccharides from K. crassifolia may be good candidates for the treatment of diseases involving the complement pathway.

No MeSH data available.


Related in: MedlinePlus

Negative ion mode ESI-CID-MS2 spectrum of the ion [MeFuc5(SO3Na)2-2Na]2− at m/z 460.120 (−2).
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marinedrugs-13-01360-f005: Negative ion mode ESI-CID-MS2 spectrum of the ion [MeFuc5(SO3Na)2-2Na]2− at m/z 460.120 (−2).

Mentions: The fragmentation for the doubly charged ion at m/z 460.120 (−2), corresponding to the ion [MeFuc5(SO3Na)2-2Na]2−, was shown in Figure 5. Five types of fragments ions were found: (1) doubly charged fragment ions at m/z 225.014 (B2), 298.075 (B3), 371.063 (B4) and 444.106 (B5) corresponded to [Fuc2(SO3Na)2-2Na]2−, [Fuc3(SO3Na)2-2Na]2−, [Fuc4(SO3Na)2-2Na]2− and [Fuc5(SO3Na)2-2Na]2−, respectively. No fragment ion at m/z 152 ([Fuc(SO3Na)2-2Na]2−) was observed, suggesting that one isomer of MeFuc5(SO3Na)2 was Fuc(SO3Na)→Fuc(SO3Na)→Fuc→Fuc→Fuc-OMe; (2) Less intense, doubly charged fragment ions at m/z 314.058 (Y3') and 387.089 (Y4') were determined to be [MeFuc3(SO3Na)2-2Na]2− and [MeFuc4(SO3Na)2-2Na]2−, most likely having arisen from glycosidic bond cleavage at the non-reducing terminus. Thus, it was hypothesized that MeFuc5(SO3Na)2 contained Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (3) Singly charged fragment ions at m/z 225.014, 371.063, 517.136 and 663.198 (namely, B1'', B2'', B3'' and B4'', respectively) arose from the loss of a methyl glycoside of sulfated fucose (257 Da) from the reducing terminus, suggesting that MeFuc5(SO3Na)2 might consist of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe or Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (4) A singly-charged fragment ion at m/z 695.225 (namely, Y4''), assigned as [MeFuc4SO3Na-Na]−, arose from the loss of a sulfated fucopyranose residue (225 Da) from the side chain or from the non-reducing terminus. A singly-charged fragment ion at 549.163 (namely, Y3''), corresponding to [MeFuc3SO3Na-Na]−, arose from the loss of fucopyranose after the loss of the sulfated fucopyranose. Thus it was hypothesized that MeFuc5(SO3Na)2 was made up of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe, Fuc(SO3Na)→Fuc(SO3Na)→ Fuc→Fuc→Fuc-OMe and Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (5) Singly-charged fragment ions at m/z 243.025 and 389.086 (namely, C1''and C2'') arose from the loss of sulfated fucose from the non-reducing terminus, suggesting that MeFuc5(SO3Na)2 might consist of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe. Thus, it was hypothesized that MeFuc5(SO3Na)2 was made up of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe, Fuc(SO3Na)→Fuc(SO3Na)→Fuc→Fuc→Fuc-OMe and Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe.


Structural analysis and anti-complement activity of polysaccharides from Kjellmaniella crsaaifolia.

Zhang W, Jin W, Sun D, Zhao L, Wang J, Duan D, Zhang Q - Mar Drugs (2015)

Negative ion mode ESI-CID-MS2 spectrum of the ion [MeFuc5(SO3Na)2-2Na]2− at m/z 460.120 (−2).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4377988&req=5

marinedrugs-13-01360-f005: Negative ion mode ESI-CID-MS2 spectrum of the ion [MeFuc5(SO3Na)2-2Na]2− at m/z 460.120 (−2).
Mentions: The fragmentation for the doubly charged ion at m/z 460.120 (−2), corresponding to the ion [MeFuc5(SO3Na)2-2Na]2−, was shown in Figure 5. Five types of fragments ions were found: (1) doubly charged fragment ions at m/z 225.014 (B2), 298.075 (B3), 371.063 (B4) and 444.106 (B5) corresponded to [Fuc2(SO3Na)2-2Na]2−, [Fuc3(SO3Na)2-2Na]2−, [Fuc4(SO3Na)2-2Na]2− and [Fuc5(SO3Na)2-2Na]2−, respectively. No fragment ion at m/z 152 ([Fuc(SO3Na)2-2Na]2−) was observed, suggesting that one isomer of MeFuc5(SO3Na)2 was Fuc(SO3Na)→Fuc(SO3Na)→Fuc→Fuc→Fuc-OMe; (2) Less intense, doubly charged fragment ions at m/z 314.058 (Y3') and 387.089 (Y4') were determined to be [MeFuc3(SO3Na)2-2Na]2− and [MeFuc4(SO3Na)2-2Na]2−, most likely having arisen from glycosidic bond cleavage at the non-reducing terminus. Thus, it was hypothesized that MeFuc5(SO3Na)2 contained Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (3) Singly charged fragment ions at m/z 225.014, 371.063, 517.136 and 663.198 (namely, B1'', B2'', B3'' and B4'', respectively) arose from the loss of a methyl glycoside of sulfated fucose (257 Da) from the reducing terminus, suggesting that MeFuc5(SO3Na)2 might consist of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe or Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (4) A singly-charged fragment ion at m/z 695.225 (namely, Y4''), assigned as [MeFuc4SO3Na-Na]−, arose from the loss of a sulfated fucopyranose residue (225 Da) from the side chain or from the non-reducing terminus. A singly-charged fragment ion at 549.163 (namely, Y3''), corresponding to [MeFuc3SO3Na-Na]−, arose from the loss of fucopyranose after the loss of the sulfated fucopyranose. Thus it was hypothesized that MeFuc5(SO3Na)2 was made up of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe, Fuc(SO3Na)→Fuc(SO3Na)→ Fuc→Fuc→Fuc-OMe and Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe; (5) Singly-charged fragment ions at m/z 243.025 and 389.086 (namely, C1''and C2'') arose from the loss of sulfated fucose from the non-reducing terminus, suggesting that MeFuc5(SO3Na)2 might consist of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe. Thus, it was hypothesized that MeFuc5(SO3Na)2 was made up of Fuc(SO3Na)→Fuc→Fuc→Fuc→Fuc(SO3Na)-OMe, Fuc(SO3Na)→Fuc(SO3Na)→Fuc→Fuc→Fuc-OMe and Fuc→Fuc→Fuc→Fuc(SO3Na)→Fuc(SO3Na)-OMe.

Bottom Line: The activity of KCA was found to be similar to KCW, suggesting that the method of extraction did not influence the activity.In addition, the degraded polysaccharides (DKCA and DKCW) displayed lower activity levels than the crude polysaccharides (KCA and KCW), indicating that molecular weight had an effect on activity.In conclusion, polysaccharides from K. crassifolia may be good candidates for the treatment of diseases involving the complement pathway.

View Article: PubMed Central - PubMed

Affiliation: Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China. wenjingwing@126.com.

ABSTRACT
Two polysaccharides, named KCA and KCW, were extracted from Kjellmaniella crassifolia using dilute hydrochloric acid and water, respectively. Composition analysis showed that these polysaccharides predominantly consisted of fucose, with galactose, mannose and glucuronic acid as minor components. After degradation and partial desulfation, electrospray ionization mass spectrometry (ESI-MS) was performed, which showed that the polysaccharides consisted of sulfated fucooligosaccharides, sulfated galactofucooligosaccharides and methyl glycosides of mono-sulfated/multi-sulfated fucooligosaccharides. The structures of the oligomeric fragments were further characterized by electrospray ionization collision-induced dissociation tandem mass spectrometry (ESI-CID-MS2 and ESI-CID-MS3). Moreover, the activity of KCA and KCW against the hemolytic activity of both the classical and alternative complement pathways was determined. The activity of KCA was found to be similar to KCW, suggesting that the method of extraction did not influence the activity. In addition, the degraded polysaccharides (DKCA and DKCW) displayed lower activity levels than the crude polysaccharides (KCA and KCW), indicating that molecular weight had an effect on activity. Moreover, the desulfated fractions (ds-DKCA and ds-DKCW) showed less or no activity, which confirmed that sulfate was important for activity. In conclusion, polysaccharides from K. crassifolia may be good candidates for the treatment of diseases involving the complement pathway.

No MeSH data available.


Related in: MedlinePlus