Structure and Antiviral Activity of the Galactofucan Sulfates Extracted from Undaria Pinnatifida (Phaeophyta)

Abstract

The galactofucan sulfate extract (GFS) obtained from the brown seaweed Undaria pinnatifida by extraction with dilute acid is a potent inhibitor of the herpes viruses HSV-1, HSV-2 and HCMV, with IC 50 values determined in vitro of 1.1, 0.2 and 0.5 μgmL −1 , respectively. Fractionation of GFS by anion exchange chromatography gave three fractions which differed in their uronic acid and sulfate contents and in their antiviral activity, as well as in having somewhat reduced molecular weights compared to GFS. The low uronic acid/high sulfate fraction (F2M), obtained in 63% yield, had similar molar proportions of galactopyranosyl and fucopyranosyl residues, little associated protein and was equipotent with GFS (IC 50 values of 1.1, 0.1 and 0.5 μgmL −1 , respectively). The high uronic acid/low sulfate fraction (F1M), obtained in 18% yield, had a much lower proportion of galactopyranosyl residues and was less active (IC 50 values of 4.6, 1.0 and 4.0 μgmL −1 , respectively). The minor low uronic acid/high sulfate fraction (F4M) had a significant amount of associated protein and was also less active (IC 50 = 3.1, 1.0 and 2.0 μgmL −1 , respectively). The structure of the major fraction (F2M) was shown to be complex by glycosyl linkage analysis before and after solvolytic desulfation, with many component sugar residues being identified, although 3-linked fucopyranosyl 2,4-disulfate residues were a prominent feature.

Free radical scavenging activity of extracts from seaweeds Macrocystis pyrifera and Undaria pinnatifida: applications as functional food in the diet of prawn Artemesia longinaris

“…Our data showed that the water-soluble extracts isolated from M. pyrifera and U. pinnatifida have different relation fucose/galactose. This relation corresponds with fucoidan content which was higher in U. pinnatifida and the values were similar to those reported in previous studies (Synytsya et al, 2010;Hemmingson et al, 2006). The kinetic of the DPPH reaction of polysacharides extract showed that the highest activity was determined in U. pinnatifida.…”

Bioactive potential and possible health effects of edible brown seaweeds

“…Furthermore it was suggested that fucan activity was not only dependent on the ionic changes but also on the sugar rings that act to spatially orientate the charges in a configuration that recognizes the enzyme, thus determining the specificity of the binding (Queiroz et al, 2008). Hemmingson et al (2006) studied the anti-viral activity of a galactofucan sulfate extract from U. pinnatifida collected from east coast of Tasmania, Australia. It was found to be a potent inhibitor of the herpes viruses HSV-1, HSV-2 and HCMV, with IC 50 values of 1.1, 0.2 and 0.5 mg/mL, respectively.…”

“…This fact suggests that marine algae, like photosynthesizing plants, have anti-oxidative mechanisms and compounds which act as anti-oxidant agents. At the same time, several species of seaweeds have also been found to produce or contain polysaccharides, glycoproteins or other secondary metabolites with antimicrobial (Cox et al, 2009;Q1 Gupta, Rajauria, & Abu-Ghannam, 2010a), antitumoral (Koyanagi, Tanigawa, Nakagawa, Soeda, & Shimeno, 2003;Zubia et al, 2009) or anti-viral activity (Artan et al, 2008;Hemmingson, Falshaw, Furneaux, & Thompson, 2006;Zhu, Chiu, Ooi, Chan, & Angjr, 2004;. Among all the three types highest phytochemical content have been reported from brown seaweeds (Seafoodplus, 2008).…”

Inhibitory activities of microalgal extracts against Epstein-Barr virus DNA release from lymphoblastoid cells

“…Carrageenan, a type of sulfated polysaccharide from red seaweeds, is a potent inhibitor of human papillomavirus (HPV) that acts by preventing the binding of HPV virions to cells (Buck et al, 2006). In addition, the galactofucan sulfate extract from the brown seaweed Undaria pinnatifida is a potent inhibitor of the herpes viruses HSV-1, HSV-2, and human cytomegalovirus (HCMV) (Hemmingson et al, 2006).…”