title: Antibacterial profiling of abietane-type diterpenoids.
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 MIC90of 60μg/mL against Staphylococcus aureus ATCC 25923, and 8μg/mL against methicillin-resistant S. aureus, Staphylococcus epidermidis and Streptococcus mitis. The IC50value for compound 10 against Balb/c 3T3 cells was 45μg/mL.
authors: Centre for Drug Research, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland.
authors: Andreas
authors: A
authors: Helfenstein
authors: Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland.
authors: Mikko
authors: M
authors: Vahermo
authors: Centre for Drug Research, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland.
authors: Dorota A
authors: DA
authors: Nawrot
authors: Pharmacognosy Department, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey.
authors: Fatih
authors: F
authors: Demirci
authors: Pharmacognosy Department, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey.
authors: Gökalp
authors: G
authors: İşcan
authors: Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland.
authors: Sara
authors: S
authors: Krogerus
authors: Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland.
authors: Jari
authors: J
authors: Yli-Kauhaluoma
authors: Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland. Electronic address: vania.moreira@helsinki.fi.
authors: Vânia M
authors: VM
authors: Moreira
authors: Centre for Drug Research, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, Viikinkaari 5 E (PO Box 56), FI-00014 University of Helsinki, Helsinki, Finland. Electronic address: paivi.tammela@helsinki.fi.
authors: Päivi
authors: P
authors: Tammela
mesh_terms: D045784:Abietanes / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D041702:BALB 3T3 Cells; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D009181:Mycoses / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects
chemical_list: D045784:Abietanes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; C013913:dehydroabietic acid; C023710:abietic acid
keywords: Abietic acid; Amino acid derivative; Bacteria; Cytotoxicity; Dehydroabietic acid; Fungi