Antibacterial serrulatane diterpenes from the Australian native plant Eremophila microtheca

Emma C. Barnes, Angela M. Kavanagh, Soumya Ramu, Mark A. Blaskovich, Matthew A. Cooper, Rohan A. Davis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Chemical investigations of the aerial parts of the Australian plant Eremophila microtheca resulted in the isolation of three serrulatane diterpenoids, 3-acetoxy-7,8-dihydroxyserrulat-14-en-19-oic acid (1), 3,7,8-trihydroxyserrulat-14-en-19-oic acid (2) and 3,19-diacetoxy-8- hydroxyserrulat-14-ene (3) as well as the previously reported compounds verbascoside (4) and jaceosidin (5). Acetylation and methylation of the major serrulatane diterpenoid 2 afforded 3,8-diacetoxy-7-hydroxyserrulat-14-en-19-oic acid (6) and 3,7,8-trihydroxyserrulat-14-en-19-oic acid methyl ester (7), respectively. The antibacterial activity of 1-7 was assessed against a panel of Gram-positive and Gram-negative bacterial isolates. All of the serrulatane compounds exhibited moderate activity against Streptococcus pyogenes (ATCC 12344) with minimum inhibitory concentrations (MICs) ranging from 64-128 μg/mL. Serrulatane 1 demonstrated activity against all Gram-positive bacterial strains (MICs 64-128 μg/mL) except for Enterococcus faecalis and Enterococcus faecium. This is the first report of natural products from E. microtheca.

Original languageEnglish
Pages (from-to)162-169
Number of pages8
JournalPhytochemistry
Volume93
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • Antibacterial
  • Diterpenoid
  • Eremophila microtheca
  • Myoporaceae
  • Serrulatane

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