Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

Bioorg Med Chem. 2001 Feb;9(2):347-56. doi: 10.1016/s0968-0896(00)00253-4.

Abstract

Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6beta-hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 microg/mL of MIC against MRSA and 4-16 microg/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 microg/mL of MIC against both MRSA and VRE.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Combinatorial Chemistry Techniques
  • Diterpenes / chemical synthesis
  • Diterpenes / pharmacology*
  • Drug Resistance, Microbial
  • Enterococcus / drug effects
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Oxidation-Reduction
  • Phenanthrenes / chemical synthesis
  • Phenanthrenes / pharmacology*
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Vancomycin Resistance

Substances

  • Anti-Bacterial Agents
  • Diterpenes
  • Phenanthrenes