Extension of Prenyl Side Chain of Flavanones as Tool to Prevent Cell Death due to Oxidative Stress

Recently, a unique class of flavonoids, characterized by the presence of prenylated side chains, called prenylated flavanones, gain more and more attention in research. Since this group defines the second most abundant class of flavonoids, they may have a huge potential as therapeutic agents against multiple diseases [1]. Possibly prenylation of those substances could be related to an improved neuro-regenerative potential [2]. Anti-oxidative activity is a major issue related to neuroprotection. Therefore, the influence of the substitution of a prenyl, geranyl, or farnesyl group at position C-8 of the flavanone naringenin concerning cytotoxic and neuroprotective effects against oxidative stress in neuronal SH-SY5Y cells was investigated. Extension of the prenyl side chain revealed an increasing cytotoxic effect against SH-SY5Y cells. However, a neuroprotective effect was determined, when cells were preconditioned with those flavanones four hours before oxidative stress was induced by NO, released from sodium nitroprusside (SNP). Since neither pretreatment with naringenin nor 8-prenylnaringenin, but treatment with 10 µM 8-geranylnaringenin and 5 µM 8-farnesylnaringenin could prevent cell death after oxidative insult, the anti-oxidative effect of prenylated Flavanones may be related to the length of prenyl side chain. Consequently, the extension of the prenyl side chain of prenylated Flavanones is supposed to have major effects on the biological activity, which could be explained by changes in the substances lipophilicity, membrane attachment and transmembrane transport capability [3], [4].

• References

• 1 Santos CMM, Silva AMS. The Antioxidant Activity of Prenylflavonoids. Molecules 2020; 25
• 2 Urmann C, Oberbauer E, Couillard-Despres S. et al. Neurodifferentiating potential of 8-prenylnaringenin and related compounds in neural precursor cells and correlation with estrogen-like activity. Planta Med 2015; 81: 305-311
• 3 Venturelli S, Burkard M, Biendl M. et al. Prenylated chalcones and flavonoids for the prevention and treatment of cancer. Nutrition 2016; 32: 1171-1178
• 4 Diller RA, Riepl HM, Rose O. et al. Ability of prenylflavanones present in hops to induce apoptosis in a human Burkitt lymphoma cell line. Planta Med 2007; 73: 755-761

Publikationsverlauf

Artikel online veröffentlicht:
12. Dezember 2022