ANTIHERPETIC AND ANTICOAGULANT PROPERTIES OF CARRAGEENANS FROM THE RED SEAWEED GIGARTINA-SKOTTSBERGII AND THEIR CYCLIZED DERIVATIVES - CORRELATION BETWEEN STRUCTURE AND BIOLOGICAL-ACTIVITY
Mj. Carlucci et al., ANTIHERPETIC AND ANTICOAGULANT PROPERTIES OF CARRAGEENANS FROM THE RED SEAWEED GIGARTINA-SKOTTSBERGII AND THEIR CYCLIZED DERIVATIVES - CORRELATION BETWEEN STRUCTURE AND BIOLOGICAL-ACTIVITY, International journal of biological macromolecules, 20(2), 1997, pp. 97-105
The antiviral activity against herpes simplex virus types 1 and 2 of k
appa/iota-, partially cyclized mu/nu-, and lambda-carrageenans isolate
d from the red seaweed Gigartina skottsbergii and their cyclized deriv
atives was analyzed. lambda-Carrageenans and the partially cyclized mu
/nu-carrageenan were the most potent inhibitors of herpes viruses (inc
luding acyclovir-resistant variants and clinical isolates), with IC50
values lower than I mu g ml(-1) against both serotypes and selectivity
indices higher than 10(3). kappa/iota-Carrageenans were slightly less
effective than the other two types with IC50 values in the range 1.6-
4.1 mu g ml(-1). Antiherpetic activity was directly correlated to the
amount of alpha-D-galactose 2,6-disulfate residues in the natural carr
ageenans. The cyclization of the alpha-D-galactose 6-sulfate and 2,6-d
isulfate units into 3,6-anhydro-alpha-D-galactose and 3,6-anhydro-alph
a-D-galactose 2-sulfate residues in these polysaccharides, in general,
lowers the antiherpetic activity of the derivatives with respect to t
he natural carrageenans. Some carrageenans showed a very reduced antic
oagulant activity only at concentrations that were considerably higher
than the IC50, whereas others were totally devoid of anticoagulant pr
operties. Among natural carrageenans, the mu/nu-type 1C(3) shows the b
est relationship between antiviral efficacy and lack of anticoagulant
action, resulting a Very promising compound. (C) 1997 Elsevier Science
B.V.