Effects of prenylflavonoids from hops against sodium nitroprusside-induced cell viability reduction in SH-SY5Y cells: Role of side chain length

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 %).