Semi-Synthesis of Different Pyranoflavonoid Backbones and the Neurogenic Potential
Corinna Urmann,
Lara Bieler,
Michael Hackl,
Olivia Chia-Leeson,
Sebastien Couillard-Despres,
Herbert Riepl
Affiliations
Corinna Urmann
Organic-Analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, 94315 Straubing, Germany
Lara Bieler
Institute of Experimental Neuroregeneration, Spinal Cord Injury and Tissue Regeneration Center Salzburg, Paracelsus Medical University Salzburg, 5020 Salzburg, Austria
Michael Hackl
TUM Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, 94315 Straubing, Germany
Olivia Chia-Leeson
TUM Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, 94315 Straubing, Germany
Sebastien Couillard-Despres
Institute of Experimental Neuroregeneration, Spinal Cord Injury and Tissue Regeneration Center Salzburg, Paracelsus Medical University Salzburg, 5020 Salzburg, Austria
Herbert Riepl
Organic-Analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, 94315 Straubing, Germany
Flavonoids and chalcones are known for their manifold biological activities, of which many affect the central nervous system. Pyranochalcones were recently shown to have a great neurogenic potential, which is partly due to a specific structural motif-the pyran ring. Accordingly, we questioned if other flavonoid backbones with a pyran ring as structural moiety would also show neurogenic potential. Different semi-synthetic approaches starting with the prenylated chalcone xanthohumol, isolated from hops, led to pyranoflavanoids with different backbones. We identified the chalcone backbone as the most active backbone with pyran ring using a reporter gene assay based on the promoter activity of doublecortin, an early neuronal marker. Pyranochalcones therefore appear to be promising compounds for further development as a treatment strategy for neurodegenerative diseases.
