Novel Aeruginosin-865 from Nostoc sp. as a potent anti-inflammatory agent
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- NMR spectroscopy, anti-inflammatory, cyanobacteria, drug discovery, peptides,
- MeSH
- Active Transport, Cell Nucleus drug effects MeSH
- Anti-Inflammatory Agents, Non-Steroidal chemistry isolation & purification pharmacology MeSH
- Cell Line MeSH
- Down-Regulation drug effects MeSH
- Glycopeptides chemistry isolation & purification pharmacology MeSH
- Interleukin-8 biosynthesis MeSH
- Humans MeSH
- Lipopeptides chemistry isolation & purification pharmacology MeSH
- Intercellular Adhesion Molecule-1 biosynthesis MeSH
- Molecular Structure MeSH
- NF-kappa B metabolism MeSH
- Nostoc chemistry growth & development MeSH
- Protein Transport drug effects MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- aeruginosin-865 MeSH Browser
- Anti-Inflammatory Agents, Non-Steroidal MeSH
- Glycopeptides MeSH
- Interleukin-8 MeSH
- Lipopeptides MeSH
- Intercellular Adhesion Molecule-1 MeSH
- NF-kappa B MeSH
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-α-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL(-1) ((4.0±1.7) μM) and (50.0±13.4) μg mL(-1) ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-κB translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.
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