Antibacterial profiling of abietane-type diterpenoids. Issue 1 (1st January 2017)

• Record Type: Journal Article
• Authors: Helfenstein, Andreas; Vahermo, Mikko; Nawrot, Dorota A.; Demirci, Fatih; İşcan, Gökalp; Krogerus, Sara; Yli-Kauhaluoma, Jari; Moreira, Vânia M.; Tammela, Päivi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 25:Issue 1(2017)
• Page Start: 132
• Page End: 137
• Publication Date: 2017-01-01
• Subjects: Abietic acid -- Dehydroabietic acid -- Amino acid derivative -- Bacteria -- Fungi -- Cytotoxicity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.10.019
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: Novel derivatives of abietic and dehydroabietic acid were synthesized. Biological activity was evaluated against a panel of bacteria and fungi. Compound10 is active against certain Gram-positive bacteria, including MRSA. 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 was10 [methyl N -(abiet-8, 11, 13-trien-18-yl)-d -serinate], with an MIC90 of 60 μg/mL against Staphylococcus aureus ATCC 25923, and 8 μg/mL against methicillin-resistant S. aureus, Staphylococcus epidermidis and Streptococcus mitis . The IC50 value for compound10 against Balb/c 3T3 cells was 45 μg/mL.