The flavonoid class encompasses over 700 distinct structural variants, all of which have been demonstrated to confer a multitude of beneficial effects on human health. Given the correlation between oxidative stress and over 100 diseases, including neurodegenerative, cardiovascular, and inflammatory diseases, it is a valuable target for the development of therapeutic agents. This study examined the effects of prenylated chalcones and flavanones derived from hops (Humulus lupulus L.), including xanthohumol, xanthohumol A, and C, as well as isoxanthohumol, 6- and 8-prenylnaringenin, and 8-geranylnaringenin, on cell viability and on revising the effect of sodium nitroprusside (SNP) on cell viability in the neuroblastoma cell line SH-SY5Y. The lowest IC50 (10.14–20.42 µM) was observed in treatment with chalcones. With regard to the protective effect against SNP, a structure-activity relationship of prenylated and geranylated flavanones indicated that the extension of the prenyl side chain is beneficial for the protective effect of prenylated flavanones against SNP treatment. In accordance with the aforementioned methodology, 8-farnesylnaringenin, comprising a chain of three isoprene units, was synthesized and the effect on cell viability and protection against SNP-induced reduction of cell viability was subsequently evaluated. The strongest impact on cell viability (IC50) was observed for 8-farnesylnaringenin, which also demonstrated the most robust protective effect (25 %).
Chalcones represent a privileged scaffold in medicinal chemistry, with pyranochalcones, featuring an additional chromane-like ring, identified as neurogenic and neuroprotective. Reporter gene assays, often used to study these and other effects, can produce false positives due to firefly luciferase stabilisation by inhibitors. The present study demonstrates that pyranochalcones inhibit firefly luciferase activity, with inhibition levels ranging from none to 100% and IC50 values of 7.82 µM to 92.99 µM. Furthermore, molecular docking offers potential structure-based explanations for the observed selectivity of compounds towards firefly luciferase inhibition. Even slight modifications in the molecular structure lead to significant changes in luciferase inhibition, underscoring the importance of these findings for understanding structure-activity relationships in reporter gene assays. Accordingly, caution is advised when using reporter gene assays based on firefly luciferase and pyranochalcones, as the IC50 values are within the range of concentrations commonly used in both in vivo and in vitro assays.
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Jennifer Baas,
Sebastian Bieringer,
Corazon Frias,
Jerico Frias,
Carolina Soehnchen,
Corinna Urmann,
Stefanie Ritter,
Herbert Riepl,
Aram Prokop
Jan Hájek,
Sebastian Bieringer,
Kateřina Voráčová,
Markéta Macho,
Kumar Saurav,
Kateřina Delawská,
Petra Divoká,
Radovan Fišer,
Gabriela Mikušová,
José Cheel,
David P. Fewer,
Dai Long Vu,
Jindřiška Paichlová,
Herbert Riepl,
Pavel Hrouzek
Lara Bieler,
Michael Vogl,
Michael Kirchinger,
Corinna Urmann,
Herbert Riepl,
Christine Bandtlow,
Lars Klimaschewski,
Ludwig Aigner,
Sébastien Couillard-Després
Berechtigungen: Open Access
Berechtigungen: Peer Reviewed
The Prenylflavonoid ENDF1 Overrules Central Nervous System Growth Inhibitors and Facilitates Regeneration of DRG Neurons (2019) Frontiers in Cellular Neuroscience 13 , S. 332.
DOI: 10.3389/fncel.2019.00332
Herbert Riepl
Berechtigungen: Peer Reviewed
Synthesis of Ether-Diols with Low Polarity from Long-Chained Fatty Alcohols for Use in Block Copolymers (2019) Journal of the American Oil Chemists' Society 96 (4), S. 433-442.
DOI: 10.1002/aocs.12197
Synthesis of Terpene Diamines Based on Camphor-Derived Dinitriles (2015) Helvetica Chimica Acta 98 (4), S. 447-452.
DOI: 10.1002/hlca.201400346
K. Doll,
Herbert Riepl,
G. Dirksen
Pathophysiological significance of steatorrhea as well as of hydroxystearic acids in the feces of calves with diarrhea (2004) Deutsche tierärztliche Wochenschrift 111 (1), S. 22-28.
K. Doll,
Herbert Riepl,
W. Eichhorn,
G. Dirksen
Bile acid concentrations in serum, bile and feces of healthy calves and calves with diarrhea (1999) Deutsche tierärztliche Wochenschrift 106 (1), S. 35-40.
Buchbeiträge
Reinhard A. Diller,
Herbert Riepl,
Oliver Rose,
Corazon Frias,
Günter Henze,
Aram Prokop
Berechtigungen: Peer Reviewed
Chapter 71: Desmethylxanthohumol from Hops, Chemistry and Biological Effects (2009) Beer in Health and Disease Prevention , S. 703-709.
DOI: 10.1016/B978-0-12-373891-2.00071-7
Reinhard A. Diller,
Herbert Riepl,
Oliver Rose,
Corazon Frias,
Günter Henze,
Aram Prokop
Desmethylxanthohumol from hops, chemistry and biological effects (2008) Enzylopaedic Handbook of Hop and Beer .
Konferenzbeiträge
Agnes Emberger-Klein,
Kristin Werner,
Corinna Urmann,
Herbert Riepl,
Klaus Menrad
This report gives details about the medical use and technology of neuroregenerative hop ingredients as well as conumer interest in related new plant-derived medicinal products.
Mehr
Agnes Emberger-Klein,
Kristin Werner,
Corinna Urmann,
Herbert Riepl,
Klaus Menrad
Refining process for separation of prenylated polyphenols (2012) DE 102012105613 A1 .
Ludwig Aigner,
Eleni Oberbauer,
Sébastien Couillard-Després,
Francisco Javier Rivera,
Herbert Riepl,
Corinna Urmann,
Martin Biendl
Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders (2011) WO/2012/172090 .
Aram Prokop,
Herbert Riepl,
Thomas Wieder
8-nitro-tryptanthrin and other tryptanthrin derivatives used for the treatment of diseases caused by highly proliferating cells (2004) WO/2004/087164 .
Wolfgang Anton Herrmann,
Jürgen A. Kulpe,
Jürgen Kellner,
Herbert Riepl
Synthetische oder mithilfe von Palmöl gewonnene Myristinsäure soll durch Ölsäure ersetzt werden, dazu wird ein Katalysator entwickelt, der die in Ölsäure vorhandene Doppelbindung zu verschieben …
Vor dem Hintergrund hoher Umweltbelastungen und eines starken Energieinputs im Baugewerbe sollen innovative Produkte wie Lehmbauplatten für den Innenausbau entwickelt und deren Akzeptanz untersucht …
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