An HIV RNase H inhibitory 1,3,4,5-tetragalloylapiitol from the African plant Hylodendron gabunensis

J Nat Prod. 2007 Oct;70(10):1647-9. doi: 10.1021/np0702279. Epub 2007 Oct 13.

Abstract

A new compound, 1,3,4,5-tetragalloylapiitol ( 1), was isolated from the aqueous extract of the plant Hylodendron gabunensis and was found to be a potent inhibitor of RNase H enzymatic activity. The structure of 1 was elucidated by NMR analyses to be an apiitol ( 2) sugar moiety substituted with four gallic acid residues. Optical rotation measurements of the free sugar following basic hydrolysis indicated that the 3 S absolute configuration was the same as that of d-apiitol. Compound 1 inhibited HIV-1, HIV-2, and human RNase H with IC 50 values of 0.24, 0.13, and 1.5 microM, respectively, but it did not show inhibition of E. coli RNase H at 10 microM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology*
  • Cameroon
  • Erythritol / analogs & derivatives*
  • Erythritol / chemistry
  • Erythritol / isolation & purification
  • Erythritol / pharmacology
  • Fabaceae / chemistry*
  • HIV-1 / drug effects
  • HIV-2 / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Ribonuclease H / antagonists & inhibitors*

Substances

  • 1,3,4,5-tetragalloylapiitol
  • Anti-HIV Agents
  • 3-(hydroxymethyl)erythritol
  • Ribonuclease H
  • Erythritol