Isolation and characterization of a sulfated polysaccharide from the brown alga Sargassum patens and determination of its anti-herpes activity.

Bioactivity-guided fractionation of the hot water extract from the brown alga Sargassun patens led to the isolation of a polysaccharide as an antiviral component against herpes simplex viruses which are the cause of cold sores (HSV-1) and genital herpes (HSV-2). The polysaccharide contained a sulfur group that could be present as a sulfate ester. It is thus a sulfated polysaccharide with a molecular mass of about 424 kDa, and is designated SP-2a. Gas chromatographic assay showed that the polysaccharide consisted of fucose, galactose, mannose, xylose, glucose, and galactosamine. The fucose is the major constituent sugar (35.3%), followed by galactose (18.4%). The 50% effective concentration (EC50) against HSV-2, HSV-1, and HSV-1 acyclovir resistant strain was 1.3, 5.5, and 4.1 microg/mL, respectively. The 50% cytotoxic concentration (CC50) of SP-2a on the growth of normal Vero cell line was more than 4000 microg/mL. Therefore SP-2a of S. patens may be a potent agent for treating HSV infections.

[1]  I. Karube,et al.  A comparison of screening methods for antioxidant activity in seaweeds , 1997, Journal of Applied Phycology.

[2]  U. Sankawa,et al.  A novel antivirally active fucan sulfate derived from an edible brown alga, Sargassum horneri. , 2001, Chemical & pharmaceutical bulletin.

[3]  J. Blay,et al.  Isolation and characterization of an anti-HSV polysaccharide from Prunella vulgaris. , 1999, Antiviral research.

[4]  E. Damonte,et al.  Antiherpetic activity and mode of action of natural carrageenans of diverse structural types. , 1999, Antiviral research.

[5]  Yong-Ki Hong,et al.  MULTIPLE ANTIVIRAL ACTIVITIES IN EXTRACTS OF SEAWEEDS FROM BRITISH COLUMBIA , 1999 .

[6]  Jung-Bum Lee,et al.  An antivirally active sulfated polysaccharide from Sargassum horneri (TURNER) C. AGARDH. , 1998, Biological & pharmaceutical bulletin.

[7]  Yong-Ki Hong,et al.  Biological activities of seaweed extracts from British Columbia, Canada, and Korea. I. Antiviral activity , 1997 .

[8]  E. Clercq,et al.  Sulfated polysaccharides extracted from sea algae as potential antiviral drugs. , 1997, General pharmacology.

[9]  E. Damonte,et al.  Antiviral activity of natural sulphated galactans on herpes virus multiplication in cell culture. , 1997, Planta medica.

[10]  H. Harada,et al.  Selective antitumor activity in vitro from marine algae from Japan coasts. , 1997, Biological & pharmaceutical bulletin.

[11]  E. Damonte,et al.  Herpes simplex virus-inhibitory sulfated xylogalactans from the red seaweed Nothogenia fastigiata. , 1996, Chemotherapy.

[12]  B. Herold,et al.  Differences in the susceptibility of herpes simplex virus types 1 and 2 to modified heparin compounds suggest serotype differences in viral entry , 1996, Journal of virology.

[13]  G. Painter,et al.  The Effect of Absolute Configuration on the Anti-HIV and Anti-HBV Activity of Nucleoside Analogues , 1995 .

[14]  E. De Clercq,et al.  Antiviral Portrait Series: 4. Polysuifates as Inhibitors of HIV and Other Enveloped Viruses , 1994 .

[15]  E. De Clercq,et al.  Activity of a Sulfated Polysaccharide Extracted from the Red Seaweed Aghardhiella Tenera against Human Immunodeficiency Virus and Other Enveloped Viruses , 1994 .

[16]  T. Nishino,et al.  Study on antihypertensive and antihyperlipidemic effects of marine algae , 1994 .

[17]  T. Mizuno,et al.  Antitumor activity and immunological properties of marine algal polysaccharides, especially fucoidan, prepared from Sargassum thunbergii of Phaeophyceae. , 1993, Anticancer research.

[18]  J. Esko,et al.  Cell surface receptors for herpes simplex virus are heparan sulfate proteoglycans , 1992, The Journal of cell biology.

[19]  B. Herold,et al.  Heparan sulfate glycosaminoglycans as primary cell surface receptors for herpes simplex virus. , 1992, Advances in experimental medicine and biology.

[20]  C. Che.  Marine products as a source of antiviral drug leads , 2004, Drug Development Research.

[21]  E. De Clercq,et al.  Differential inhibitory effects of sulfated polysaccharides and polymers on the replication of various myxoviruses and retroviruses, depending on the composition of the target amino acid sequences of the viral envelope glycoproteins , 1991, Antimicrobial Agents and Chemotherapy.

[22]  E. Lycke,et al.  Binding of herpes simplex virus to cellular heparan sulphate, an initial step in the adsorption process. , 1991, The Journal of general virology.

[23]  B. Herold,et al.  Glycoprotein C of herpes simplex virus type 1 plays a principal role in the adsorption of virus to cells and in infectivity , 1991, Journal of virology.

[24]  E. De Clercq,et al.  Sulphated Polymers are Potent and Selective Inhibitors of Various Enveloped Viruses, Including Herpes Simplex Virus, Cytomegalovirus, Vesicular Stomatitis Virus, Respiratory Syncytial Virus, and Toga-, Arena- and Retroviruses , 1990 .

[25]  E. Telford,et al.  Stability of the Herpesvirus Ribonucleotide Reductase-Inhibiting Nonapeptide YAGAVVNDL in Extracts of HSV-1-Infected Cells , 1990 .

[26]  E. De Clercq,et al.  Sulfated polysaccharides are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, and human immunodeficiency virus , 1988, Antimicrobial Agents and Chemotherapy.

[27]  H. Mitsuya,et al.  Dextran sulfate suppression of viruses in the HIV family: inhibition of virion binding to CD4+ cells. , 1988, Science.

[28]  J. van der Meer,et al.  Interspecific, Intraspecific and Nutritionally-Determined Variations in the Composition of. Agars from Gracilaria spp. , 1984 .

[29]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[30]  R. Henry,et al.  A SIMPLE AND RAPID PREPARATION OF ALDITOL ACETATES FOR MONOSACCHARIDE ANALYSIS , 1983 .

[31]  G. Vlachogiannis,et al.  Determination of the molecular weight of clinical dextran by gel permeation chromatography on TSK PW type columns , 1982 .

[32]  R. T. Walker,et al.  Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus. , 1980, The Journal of infectious diseases.

[33]  E. Kern,et al.  Antiviral Activity of Extracts from Marine Algae , 1978, Antimicrobial Agents and Chemotherapy.

[34]  A. Nahmias,et al.  INHIBITORY EFFECT OF HEPARIN ON HERPES SIMPLEX VIRUS , 1964, Journal of bacteriology.

[35]  F. Smith,et al.  COLORIMETRIC METHOD FOR DETER-MINATION OF SUGAR AND RELATED SUBSTANCE , 1956 .