Antimycobacterial metabolites from Plectranthus: royleanone derivatives against Mycobacterium tuberculosis strains

Chem Biodivers. 2010 Apr;7(4):922-32. doi: 10.1002/cbdv.200900099.

Abstract

The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7alpha-acetoxy-6beta,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H(37)Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 microg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3 Cells
  • Abietanes / chemistry*
  • Abietanes / isolation & purification
  • Abietanes / toxicity
  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / toxicity
  • Chlorocebus aethiops
  • Drug Resistance, Multiple, Bacterial / drug effects
  • Mice
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects*
  • Plectranthus / chemistry
  • Plectranthus / metabolism*
  • Vero Cells

Substances

  • Abietanes
  • Anti-Bacterial Agents
  • royleanone