Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides.

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  • Additional Information
    • Source:
      Publisher: Elsevier Country of Publication: England NLM ID: 0151434 Publication Model: Print Cited Medium: Print ISSN: 0031-9422 (Print) Linking ISSN: 00319422 NLM ISO Abbreviation: Phytochemistry Subsets: MEDLINE
    • Publication Information:
      Publication: 2003- : London : Elsevier
      Original Publication: 1961-2003: Oxford : Pergamon Press.
    • Subject Terms:
      Antiviral Agents/*chemical synthesis ; Antiviral Agents/*pharmacology ; Diglycerides/*chemical synthesis ; Diglycerides/*pharmacology ; Herpesvirus 1, Human/*drug effects ; Herpesvirus 2, Human/*drug effects; Diglycerides/chemistry ; Glycosylation ; Inhibitory Concentration 50 ; Nuclear Magnetic Resonance, Biomolecular ; Structure-Activity Relationship
    • Abstract:
      Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types 1 and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5+/-0.5 and 18.5+/-1.5 microg/ml, respectively.
    • Accession Number:
      0 (Antiviral Agents)
      0 (Diglycerides)
    • Publication Date:
      Date Created: 20031106 Date Completed: 20040205 Latest Revision: 20190901
    • Publication Date:
      20240829
    • Accession Number:
      10.1016/j.phytochem.2003.09.008
    • Accession Number:
      14599523