Naringenin

Structure

Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4′, 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7.

Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable. Racemization of (S)-(−)-naringenin has been shown to occur fairly quickly.

Sources and bioavailability

Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit, oranges, and lemons, sour cherries, tomatoes, cocoa, Greek oregano, water mint, as well as in beans. Ratios of naringenin to naringin vary among sources, 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.

The enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2S)-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. The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound. Naringenin has been proposed as a potential nephroprotective agent in diabetic kidney disease.

References

References

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