Abstract
Naringenin is a flavanone present in citrus fruit as a mixture of chiral isomers. The numerous biological properties attributed to this compound include antioxidant and anti-inflammatory activities, even though the molecular mechanisms of these remain unknown. This study aims to evaluate the effects of racemic and enantiomeric naringenin on the expression levels of miR-17-3p, miR-25-5p and relative mRNA targets, to elucidate the mechanisms underlying these antioxidant and anti-inflammatory properties. Caco-2 cells, a well characterized in vitro model which mimics the intestinal barrier, were treated with subtoxic concentrations of racemate and enantiomers. The expression levels of miR-17-3p and miR-25-5p were determined by Real-Time PCR and were found to be decreased for both miRNAs. miR-17-3p behavior was in agreement with the increased levels of target mRNAs coding for two antioxidant enzymes, manganese-dependent superoxide dismutase (MnSOD) and glutathione peroxidase 2 (GPx2), while expression levels of miR-25-5p were not in agreement with its target mRNAs, coding for two pro-inflammatory cytokines, Tumor necrosis factor-alpha (TNF-α) and Interleukin-6 (IL-6). These results lead to the conclusion that naringenin could exert its antioxidant activity through epigenetic regulation operated by miRNAs, while anti-inflammatory activity is regulated by other miRNAs and/or mechanisms.
Highlights
Naringenin (5,7,4-thihydroxyflavanone) is a chiral flavonoid belonging to the class of flavanones.It is widely distributed in fruits of Citrus species, especially in grapefruit (Citrus paradisi Macfad.) and oranges (Citrus sinensis (L.) Osbeck), as well as tomatoes (Solanum lycopersicum L.) [1,2]
PCR and were found to be decreased for both miRNAs. miR-17-3p behavior was in agreement with the increased levels of target mRNAs coding for two antioxidant enzymes, manganese-dependent superoxide dismutase (MnSOD) and glutathione peroxidase 2 (GPx2), while expression levels of miR-25-5p were not in agreement with its target mRNAs, coding for two pro-inflammatory cytokines, Tumor necrosis factor-alpha (TNF-α) and Interleukin-6 (IL-6)
In order to dispose of both naringenin enantiomers, the resolution of commercially available (R/S) naringenin was accomplished via preparative enantioselective chromatography employing
Summary
Naringenin (5,7,4-thihydroxyflavanone) is a chiral flavonoid belonging to the class of flavanones. It is widely distributed in fruits of Citrus species, especially in grapefruit (Citrus paradisi Macfad.) and oranges (Citrus sinensis (L.) Osbeck), as well as tomatoes (Solanum lycopersicum L.) [1,2]. Naringin content depends on the variety and ranges from 115 to. Naringenin is mainly found in its free form (ranging from 0.8 to 4.2 mg/100 g of whole red tomato) [2]. When naringenin is present as an aglycone, it occurs as a mixture of enantiomers whose ratio depends on the ripeness of the fruit and the purification methods used to isolate the isomers [6,7]
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