| In vivo: |
| J Agric Food Chem. 2009 Jul 22;57(14):6432-7. | | Identification and quantification of metabolites of orally administered naringenin chalcone in rats.[Pubmed: 19558184] | Naringenin chalcone is the main active component of tomato skin extract, which has an antiallergic activity.
METHODS AND RESULTS:
In this study, naringenin chalcone was orally administered to rats, and the chemical structures and levels of the major metabolites in the plasma and urine of rats were determined. HPLC analysis indicated the presence of three major metabolites in the urine. LC-MS and NMR analyses tentatively identified these as naringenin chalcone-2'-O-beta-D-glucuronide, Naringenin-7-O-beta-D-glucuronide, and naringenin-4'-O-beta-D-glucuronide. Naringenin chalcone-2'-O-beta-D-glucuronide was the only metabolite detected in the plasma, and its peak plasma level was observed 1 h after naringenin chalcone administration. Naringenin chalcone-2'-O-beta-D-glucuronide also inhibited histamine release from rat peritoneal mast cells stimulated with compound 48/80.
CONCLUSIONS:
This activity might contribute to the antiallergic activity of naringenin chalcone in vivo. To the best of the authors' knowledge, this study is the first to report determination of naringenin chalcone metabolites in rat plasma and urine. | | Int J Food Sci Nutr. 2013 Nov;64(7):843-9. | | Effects of naringenin and its phase II metabolites on in vitro human macrophage gene expression.[Pubmed: 23883170 ] | Naringenin, together with its glycosidic forms, is a flavanone abundant in grapefruit and orange. It has been detected in human plasma, following citrus juice intake, at sub-μmolar concentrations, and its main phase II conjugated metabolites (naringenin-7-O-glucuronide(Naringenin-7-O-beta-D-glucuronide) and narigenin-4'-O-glucuronide) have been identified in urine.
Recent evidence suggests a potential active anti-inflammatory role of flavonoids on macrophages, cells actively involved in atherogenesis.
The aim of this study was to evaluate the effects of naringenin and its phase II metabolites on the expression of specific genes in differently activated macrophages at concentrations coherent with dietary exposure.
METHODS AND RESULTS:
Results suggest that phase II metabolites, as well as the aglyconic form of naringenin, were able to perturb macrophage gene expression in directions that are not always consistent with anti-inflammatory effects. Moreover, the effects of metabolites were not always consistent with each other and with those of their aglycone, underlining the paramount importance of testing physiological forms of phytochemicals within in vitro experimental models.
In vivo studies are needed to further explore these observations and investigate their practical consequences. |
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