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 IC50 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 (IC50 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 (IC50 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 (IC50 = 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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Berteau O, Mulloy B (2003) Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. Glycobiol 13:29R–40R
Bilan MI, Grachev AA, Ustuzhanina NE, Shashkov AS, Nifant'ev NE, Usov AI (2002) Structure of a fucoidan from the brown seaweed Fucus evanescens C.Ag. Carbohydr Res 337:719–730
Bilan MI, Grachev AA, Ustuzhanina NE, Shashkov AS, Nifant'ev NE, Usov AI (2004) A highly regular fraction of a fucoidan from the brown seaweed Fucus distichus L. Carbohydr Res 339:511–517
Chizhov AO, Dell A, Morris HR, Haslam SM, McDowell RA, Shashkov AS, Nifant'ev NE, Khatuntseva EA, Usov AI (1999) A study of fucoidan from the brown seaweed Chorda filum. Carbohydr Res 320:108–119
Duarte MER, Cardoso MA, Noseda MD, Cerezo AS (2001) Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum. Carbohydr Res 333:281– 293
Dubois M, Gillies KA, Hamilton JK, Rebers PA, Smith F (1956) Colorimetric method for determination of sugars and related substances. Anal Chem 28:350–356
Falshaw R, Furneaux RH (1994) Carrageenan from the tetrasporic stage of Gigartina decipiens (Gigartinaceae, Rhodophyta). Carbohydr Res 252:171–182
Katsube T, Yamasaki Y, Iwamoto M, Oka S (2003) Hyaluronidase-inhibiting polysaccharide isolated and purified from hot water extract of sporophyll of Undaria pinnatifida. Food Sci. Technol Res 9:25–29
Lee JB, Hayashi K, Hashimoto M, Nakano T, Hayashi T (2004) Novel antiviral fucoidan from sporophyll of Undaria pinnatifida (Mekabu). Chem Pharm Bull 52:1091–1094
Majczak GAH, Richartz RRTB, Duarte MER, Noseda MD (2003) Antiherpetic activity of heterofucans isolated from Sargassum stenophyllum (Fucales, Phaeophyta). Proc. XVIIth Int Seaweed Symp: 169–174
Mori H, Kamei H, Nishide E, Nisizawa K (1982) Sugar constituents of some sulfated polysaccharides from the sporophylls of wakame (Undaria pinnatifida) and their biological activities. In: Marine Algae in Pharmaceutical Science. Walter de Gruyter, Berlin Vol 2:109–121 Need editor(s) of this book
Nishino T, Nishioka C, Ura H, Nagumo T (1994) Isolation and partial characterization of a novel amino sugar-containing fucan sulfate from commercial Fucus vesiculosus fucoidan. Carbohydr Res 255:213–224
Ponce NMA, Pujol CA, Damonte EB, Flores ML, Stortz CA (2003) Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. Carbohydr Res 338:153–165
Stanley RA, Lee SP, Roberton AM (1983) Heterogeneity in gastrointestinal mucins. Biochim Biophys Acta 760:262–269
Stevenson TT, Furneaux RH (1991) Chemical methods for the analysis of sulphated galactans from red algae. Carbohydr Res 210:277–298
Thompson KD, Drager C (2004) Antiviral activity of Undaria pinnatifida against herpes simplex virus. Phytother Res 18:551–555
Usov AI, Bilan MI, Klochkova NG (1995) Polysaccharides of algae. 48. Polysaccharide composition of several calcareous red algae: Isolation of alginate from Corallina pilulifera P. et R. (Rhodophyta, Corallinaceae). Bot Mar 38:43–51
Witvrouw M, De Clercq E (1997) Sulfated polysaccharides extracted from sea algae as potential antiviral drugs. Gen Pharmac 29:497–511
Zhu W, Ooi VEC, Chan PKS, Ang jr PO (2003) Isolation and characterization of a sulfated polysaccharide from the brown alga Sargassum patens and determination of its antiherpes activity. Biochem Cell Biol 81:25–33
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hemmingson, J.A., Falshaw, R., Furneaux, R.H. et al. Structure and Antiviral Activity of the Galactofucan Sulfates Extracted from Undaria Pinnatifida (Phaeophyta). J Appl Phycol 18, 185–193 (2006). https://doi.org/10.1007/s10811-006-9096-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10811-006-9096-9