TY - JOUR
T1 - Antibacterial profiling of abietane-type diterpenoids
AU - Helfenstein, Andreas
AU - Vahermo, Mikko
AU - Nawrot, Dorota A
AU - Demirci, Fatih
AU - İşcan, Gökalp
AU - Krogerus, Sara
AU - Yli-Kauhaluoma, Jari
AU - Moreira, Vânia M.
AU - Tammela, Päivi
N1 - Copyright © 2016 Elsevier Ltd. All rights reserved.
PY - 2017/1/1
Y1 - 2017/1/1
N2 - 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.
AB - 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.
KW - abietic acid
KW - dehydroabietic acid
KW - amino acid derivative
KW - bacteria
KW - fungi
KW - cytotoxicity
U2 - 10.1016/j.bmc.2016.10.019
DO - 10.1016/j.bmc.2016.10.019
M3 - Article
C2 - 27793449
SN - 0968-0896
VL - 25
SP - 132
EP - 137
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 1
ER -