Anti-human immunodeficiency virus-1 protease activity of new lanostane-type triterpenoids from Ganoderma sinense

Chem Pharm Bull (Tokyo). 2009 Oct;57(10):1076-80. doi: 10.1248/cpb.57.1076.

Abstract

Five new highly oxygenated lanostane-type triterpenoids [ganoderic acid GS-1 (1), ganoderic acid GS-2 (2), ganoderic acid GS-3 (3), 20(21)-dehydrolucidenic acid N (4) and 20-hydroxylucidenic acid A (5)] were isolated from the fruiting body of Ganoderma sinense, together with known compounds including 6 triterpenoids and 3 sterols. The structures of the new triterpenoids determined by spectroscopic means including 2D NMR were 7beta-hydroxy-3,11,15-trioxo-lanosta-8,24(E)-dien-26-oic acid (1), 7beta,15alpha-dihydroxy-3,11-dioxo-lanosta-8,24(E)-dien-26-oic acid (2), 12beta-acetoxy-3beta,7beta-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid (3), 3beta,7beta-dihydroxy-11,15-dioxo-25,26,27-trinorlanosta-8,20-dien-24-oic acid (4), and 7beta,20xi-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid (5), respectively. Among these, ganoderic acid GS-2, 20-hydroxylucidenic acid N, 20(21)-dehydrolucidenic acid N and ganoderiol F inhibited human immunodeficiency virus-1 protease with IC(50) values of 20-40 microM.

MeSH terms

  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology
  • Ganoderma / chemistry*
  • HIV Protease / chemistry*
  • HIV Protease / metabolism
  • HIV Protease Inhibitors / chemistry*
  • HIV Protease Inhibitors / isolation & purification
  • HIV Protease Inhibitors / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Anti-HIV Agents
  • HIV Protease Inhibitors
  • Triterpenes
  • HIV Protease
  • p16 protease, Human immunodeficiency virus 1