A sulfated galactofucan from the brown alga Hormophysa cuneiformis (Fucales, Sargassaceae).

The brown alga Hormophysa cuneiformis collected from the coastal waters of Vietnam was used to isolate a mixture of sulfated polysaccharides FHC, which was fractionated further by anion-exchange chromatography on DEAE-Sephacel. The main fraction F3 eluted with 1.5 M NaCl contained essentially l-fucose, d-galactose and sulfate and has very complex NMR spectra. Desulfation to obtain F3deS followed by Smith degradation to obtain F3deS-Sm was used to simplify the structure of F3, and all these preparations were characterized by methylation analysis and NMR spectra. A linear (1 → 3)-linked backbone built up of α-l-fucopyranose residues was identified as the main structural motif of molecules. Some fucose residues attached to position 4 of its 3-linked neighbor were found as branches. Galactose residues having both α- and ß-configurations were found mostly at the periphery of molecules. They are present as (1 → 6)-linked disaccharide of two ß-d-Galp attached to position 4 of the backbone or as single α-d-Galp attached to the same position. Sulfate groups in F3 may probably occupy any positions of the molecule. F3 acts as anticoagulant and is about half as active as the standard low-molecular mass heparin (enoxaparin). FHC was practically inactive in cytotoxicity test against six human cancer cell lines.

Sulfated polysaccharides of the Vietnamese brown alga Sargassum aquifolium (Fucales, Sargassaceae).

A fucoidan preparation named FSA was isolated from the brown alga Sargassum aquifolium collected from the coastal waters of Vietnam. l-Fucose, d-galactose, d-mannose, d-glucuronic acid, d-xylose, and sulfate were found to be the main constituents of FSA. The preparation was fractionated by anion-exchange chromatography on DEAE-Sephacel eluted stepwise with 0.5, 1.0, 1.5, and 2.0 M NaCl to give four fractions differing in monosaccharide composition and degree of sulfation. Their NMR spectra were too complex to be completely interpreted. Fractions 1.0 M and 1.5 M were analyzed by methylation before and after desulfation. In addition, desulfated 1.0 M was fractionated by anion-exchange chromatography into six fractions according to the uronic acid content. They were characterized by methylation and NMR spectral data, and three structurally different polysaccharides were identified. One of them has a core of alternating 2-linked α-d-Manp and 4-linked ß-d-GlcpA residues, about a half of the former bearing single α-l-Fucp or ß-d-Xylp at position 3. The second polymer is a (1 â†’ 3)-ß-d-glucopyranuronan partially substituted with single ß-d-Xylp or single α-l-Fucp at position 4. The third polysaccharide is a xylo(fuco)galactan having a linear core of alternating 4-linked α-d-Gal and 3-linked ß-d-Gal residues. The latter bear single ß-d-Xylp or a short chain of 4-linked ß-d-Xyl, 6-linked ß-d-Gal, and variously linked α-l-Fuc. In FSA, these polysaccharides are sulfated at different positions and devoid of regularity. Fractions of FSA possess anticoagulant, cytotoxic, and antitumor activities, which increase with the degree of sulfation. The most sulfated fraction 2.0 M that contains mainly a sulfated fucogalactan, is about half as active as anticoagulant as the standard low-molecular mass heparin (enoxaparin).