Naringenin is a flavanone from the flavonoid group of .[
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The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024.[ High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.][ Taking dietary supplements or consuming grapefruit excessively may impair the action of and increase the toxicity of various prescription drugs.][
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Similar to present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications.
Structure
Naringenin has the skeleton structure of a flavanone with three at the 4′, 5, and 7 carbons.[ It may be found both in the Aglycone form, naringenin, or in its Glycoside form, naringin, which has the addition of the disaccharide neohesperidose attached via a Glycosidic bond linkage at carbon 7.
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Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.
Sources and bioavailability
Naringenin and its glycoside has been found in a variety of and , including grapefruit, oranges, and lemons,[ Bitter orange,][ as do enantiomeric ratios.]
The naringenin-7-glucoside form seems less bioavailable than the aglycol form.
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.
Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste.
Biosynthesis and metabolism
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[ Naringenin is derived from malonyl-CoA and Coumaroyl-CoA.][ The latter is derived from phenylalanine. The resulting tetraketide is acted on by chalcone synthase to give the chalcone that then undergoes ring-closure to naringenin.]
The enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2 S)-naringenin to produce diphosphate and 8-prenylnaringenin. Cunninghamella elegans, a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation.
Metabolic fate and research
The fate and biological roles of naringenin are difficult to study because naringenin is rapidly metabolized in the intestine and liver, and its metabolites are destined for excretion.[
Naringenin has been proposed as a potential nephroprotective agent in diabetic kidney disease.][Valle-Velázquez, E.; Zambrano-Vásquez, O.R.; Cortés-Camacho, F.; Sánchez-Lozada, L.G.; Guevara-Balcázar, G.; Osorio-Alonso, H. (2024). "Naringenin – a potential nephroprotective agent for diabetic kidney disease: A comprehensive review of scientific evidence". Biomolecules and Biomedicine. 24 (6): 1441–1451.]
