Antibacterial profiling of abietane-type diterpenoids

Andreas Helfenstein, Mikko Vahermo, Dorota A Nawrot, Fatih Demirci, Gökalp İşcan, Sara Krogerus, Jari Yli-Kauhaluoma, Vânia M. Moreira, Päivi Tammela

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Abstract

Abietic and dehydroabietic acid are interesting diterpenes with a highly diverse repertoire of associated bioactivities. They have, among others, shown antibacterial and antifungal activity, potentially valuable in the struggle against the increasing antimicrobial resistance and imminent antibiotic shortage. In this paper, we describe the synthesis of a set of 9 abietic and dehydroabietic acid derivatives containing amino acid side chains and their in vitro antimicrobial profiling against a panel of human pathogenic microbial strains. Furthermore, their in vitro cytotoxicity against mammalian cells was evaluated. The experimental results showed that the most promising compound was 10 [methyl N-(abiet-8,11,13-trien-18-yl)-d-serinate], with an MIC90 of 60μg/mL against Staphylococcus aureus ATCC 25923, and 8μg/mL against methicillin-resistant S. aureus, Staphylococcus epidermidis and Streptococcus mitis. The IC50 value for compound 10 against Balb/c 3T3 cells was 45μg/mL.

Original languageEnglish
Pages (from-to)132-137
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume25
Issue number1
Early online date17 Oct 2016
DOIs
Publication statusPublished - 1 Jan 2017

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Keywords

  • abietic acid
  • dehydroabietic acid
  • amino acid derivative
  • bacteria
  • fungi
  • cytotoxicity

Cite this

Helfenstein, A., Vahermo, M., Nawrot, D. A., Demirci, F., İşcan, G., Krogerus, S., ... Tammela, P. (2017). Antibacterial profiling of abietane-type diterpenoids. Bioorganic and Medicinal Chemistry, 25(1), 132-137. https://doi.org/10.1016/j.bmc.2016.10.019