Characterization of the interaction of the antifungal and cytotoxic cyclic glycolipopeptide hassallidin with sterol-containing lipid membranes
Humisto, A., Jokela, J., Teigen, K., Wahlsten, M., Permi, P., Sivonen, K., & Herfindal, L. (2019). Characterization of the interaction of the antifungal and cytotoxic cyclic glycolipopeptide hassallidin with sterol-containing lipid membranes. Biochimica et Biophysica Acta : Biomembranes, 1861(8), 1510-1521. https://doi.org/10.1016/j.bbamem.2019.03.010
Published inBiochimica et Biophysica Acta : Biomembranes
© 2019 The Authors.
Hassallidins are cyclic glycolipopeptides produced by cyanobacteria and other prokaryotes. The hassallidin structure consists of a peptide ring of eight amino acids where a fatty acid chain, additional amino acids, and sugar moieties are attached. Hassallidins show antifungal activity against several opportunistic human pathogenic fungi, but does not harbor antibacterial effects. However, they have not been studied on mammalian cells, and the mechanism of action is unknown. We purified hassallidin D from cultured cyanobacterium Anabaena sp. UHCC 0258 and characterized its effect on mammalian and fungal cells. Ultrastructural analysis showed that hassallidin D disrupts cell membranes, causing a lytic/necrotic cell death with rapid presence of disintegrated outer membrane, accompanied by internalization of small molecules such as propidium iodide into the cells. Furthermore, artificial liposomal membrane assay showed that hassallidin D selectively targets sterol-containing membranes. Finally, in silico membrane modeling allowed us to study the interaction between hassallidin D and membranes in detail, and confirm the role of cholesterol for hassallidin-insertion into the membrane. This study demonstrates the mechanism of action of the natural compound hassallidin, and gives further insight into how bioactive lipopeptide metabolites selectively target eukaryotic cell membranes. ...
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Academy Project, AoF
Additional information about fundingThis work was supported by a Jane and Aatos Erkko Foundation (Finland) grant to K.S., the Academy of Finland grant 288235 to P.P., and the Norwegian Cancer Society and Western Norway Health Authorities to L.H. K.S. and L.H. also received funding from the NordForsk NCoE Programme “NordAqua” (project #82845). A.H. was funded by the Doctoral Programme in Microbiology and Biotechnology (University of Helsinki, Department of Microbiology). ...
Showing items with similar title or keywords.
Oxidative DNA cleavage mediated by a new unexpected [Pd(BAPP)][PdCl4] complex (BAPP = 1,4-bis(3-aminopropyl)piperazine) : crystal structure, DNA binding and cytotoxic behavior Ragab, Mona S.; Shehata, Mohamed R.; Shoukry, Mohamed M.; Haukka, Matti; Ragheb, Mohamed A. (Royal Society of Chemistry (RSC), 2022)A novel Pd(II) double complex, [Pd(BAPP)][PdCl4], containing the 1,4-bis(3-aminopropyl)piperazine (BAPP) ligand is investigated. X-ray crystallography of a single crystal confirmed the structure of the [Pd(BAPP)][PdCl4] ...
Salix spp. Bark Hot Water Extracts Show Antiviral, Antibacterial, and Antioxidant Activities : The Bioactive Properties of 16 Clones Tienaho, Jenni; Reshamwala, Dhanik; Sarjala, Tytti; Kilpeläinen, Petri; Liimatainen, Jaana; Dou, Jinze; Viherä-Aarnio, Anneli; Linnakoski, Riikka; Marjomäki, Varpu; Jyske, Tuula (Frontiers Media SA, 2021)Earlier studies have shown that the bark of Salix L. species (Salicaceae family) is rich in extractives, such as diverse bioactive phenolic compounds. However, we lack knowledge on the bioactive properties of the bark of ...
Zandi, Linda; Makungu, Marco; Munissi, Joan J. E.; Duffy, Sandra; Puttreddy, Rakesh; von der Heiden, Daniel; Rissanen, Kari; Avery, Vicky M.; Nyandoro, Stephen S.; Erdélyi, Máté (American Chemical Society (ACS), 2020)The new 2,3-secoiridoids morisecoiridoic acids A (1) and B (2), the new iridoid 8-acetoxyepishanzilactone (3), and four additional known iridoids (4–7) were isolated from the leaf and stem bark methanol extracts of Morinda ...
Toxicological and bioactivity evaluation of blackcurrant press cake, sea buckthorn leaves and bark from Scots pine and Norway spruce extracts under a green integrated approach Pap, Nora; Reshamwala, Dhanik; Korpinen, Risto; Kilpeläinen, Petri; Fidelis, Marina; Furtado, Marianna M.; Sant’Ana, Anderson S.; Wen, Mingchun; Zhang, Liang; Hellström, Jarkko; Marnilla, Pertti; Mattila, Pirjo; Sarjala, Tytti; Yang, Baoru; dos Santos Lima, Amanda; Azevedo, Luciana; Marjomäki, Varpu; Granato, Daniel (Elsevier, 2021)Aqueous extracts from blackcurrant press cake (BC), Norway spruce bark (NS), Scots pine bark (SP), and sea buckthorn leaves (SB) were obtained using maceration and pressurized hot water and tested for their bioactivities. ...
Field-Grown and In Vitro Propagated Round-Leaved Sundew (Drosera rotundifolia L.) Show Differences in Metabolic Profiles and Biological Activities Tienaho, Jenni; Reshamwala, Dhanik; Karonen, Maarit; Silvan, Niko; Korpela, Leila; Marjomäki, Varpu; Sarjala, Tytti (MDPI AG, 2021)Drosera rotundifolia L. is a carnivorous plant used in traditional medicine for its therapeutic properties. Because of its small size, its collection in nature is laborious and different cultivation methods have been studied ...