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J Nat Prod. 1998 Jul;61(7):891-5.

The inhibition of the reverse transcriptase of HIV-1 by the natural sulfoglycolipids from cyanobacteria: contribution of different moieties to their high potency.

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  • 1Department of Cell Biology and Histology, Sackler School of Medicine and School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Ramat-Aviv, Tel-Aviv 69978, Israel.

Abstract

The potent in vitro inhibition of the enzymatic activity of the human immunodeficiency virus-1 (HIV-1) reverse transcriptase (RT) by the lipophilic extracts of cyanobacteria8 was primarily attributed to the sulfoquinovosylpranosyl lipids, compounds 1-4. These sulfolipids inhibit efficiently and selectively only the DNA polymerase activity of HIV-1 RT (and not the ribonuclease H function) with 50% inhibitory concentration value (IC50) as low as 24 nM exhibited by compound 1. The novel natural compound 4, in which two hydroxy groups on the sugar moiety are substituted by palmitoyl residues, exhibits a significant decrease in the maximal inhibition capacity. It is possible, therefore, that the contribution of acylated groups to the molecule at these positions interferes with inhibition, possibly, by steric hindrance. Both the sulfonic acid moiety and the fatty acid ester side chain have a substantial effect in potentiating the extent of inhibition. For one, the inhibitory effects of all the natural glycolipids tested (5-8) are markedly reduced, and the hydrolysis of the fatty acid side chain, as in derivative 9, has substantially abolished the inhibition of HIV RT.

PMID:
9677270
DOI:
10.1021/np970585j
[PubMed - indexed for MEDLINE]
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