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.
Highlights
Kjellmaniella crassifolia is a brown alga that is widely distributed in the waters around the southern area of Hokkaido, Japan
The structural features of the polysaccharide from K. crassifolia have been previously analyzed by extracellular enzyme assays [3] and NMR [4]
For the determination of sugar composition, the acid-hydrolyzed glycoses were converted into their 1-phenyl-3-methyl-5-pyrazolone derivatives (PMP)
Summary
Kjellmaniella crassifolia is a brown alga that is widely distributed in the waters around the southern area of Hokkaido, Japan. K. crassifolia contains high levels of polysaccharides (fucoidan) and the water extract shows very high viscoelasticity. The polysaccharide extract from K. crassifolia is an effective immunomodulator and a potent immune adjuvant [1,2]. The structural features of the polysaccharide (fucoidan, not alginate) from K. crassifolia have been previously analyzed by extracellular enzyme assays [3] and NMR [4]. The former reported that the novel polysaccharide was fucoglucuronomannan, with a backbone consisting of alternating 4-linked. The latter study suggested that the polysaccharide was sulfated fucan, with a backbone of 3-linked fucopyranose sulfated at C-2 and C-4. Sensitivity and selectivity, mass spectroscopy (MS) with electrospray ionization (ESI-MS) is an important tool for the analysis of polysaccharides; this technique has been used to successfully elucidate the structures of other heteropolysaccharides [5,6,7]
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