Bioactive kaurane diterpenoids from Annona glabra

J Nat Prod. 1998 Apr;61(4):437-9. doi: 10.1021/np970497z.

Abstract

Phytochemical analysis of the fruits of Annona glabra yielded two new kaurane diterpenoids, annoglabasin A (methyl-16 beta-acetoxy-19-al-ent-kauran-17-oate)(1) and annoglabasin B (16 alpha-hydro-19-acetoxy-ent-kauran-17-oic acid)(2), along with 11 known kaurane derivatives (3-13). The structures of the new compounds were established by spectral and chemical evidence. Among these, methyl-16 alpha-hydro-19-al-ent-kauran-17-oate (11) exhibited mild activity against HIV replication in H9 lymphocyte cells, and 16 alpha-17-dihydroxy-ent-kauran-19-oic acid (4) showed significant inhibition of HIV-reverse transcriptase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology
  • Carbohydrate Sequence
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • HIV / enzymology
  • Humans
  • Lymphocytes / drug effects
  • Lymphocytes / virology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Sequence Data
  • Plants, Medicinal / chemistry*
  • Reverse Transcriptase Inhibitors / isolation & purification
  • Reverse Transcriptase Inhibitors / pharmacology
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Anti-HIV Agents
  • Diterpenes
  • Reverse Transcriptase Inhibitors