Difference Between Naringin and Naringenin

The key difference between naringin and naringenin is that naringin has a bitter taste, whereas naringenin is tasteless and colorless.

Naringin is a type of flavonoid that occurs naturally in citrus fruits. Naringenin is a flavorless and colorless flavanone substance.

CONTENTS

1. Overview and Key Difference
2. What is Naringin 
3. What is Naringenin
4. Similarities Between Naringin and Naringenin
5. Side by Side Comparison – Naringin vs Naringenin in Tabular Form
6. Summary

What is Naringin?

Naringin is a type of flavonoid that occurs naturally in citrus fruits. We can name it as a flavanone-7-O-glycoside that comes in between naringenin and disaccharide neohesperidose. We can find this flavonoid specifically in grapefruit. In grapefruits, it is responsible for the bitter taste of the fruit. Therefore, when commercially producing the grapefruit juice, we are using the naringinase enzyme in order to remove the bitterness of the juice. However, the human body can metabolize this substance into aglycone naringenin which is not bitter tasting, and this metabolism can be observed in the gut.

Generally, a flavonoid compound consists of 15 carbon atoms arranged in 3 ring structures. Among these ring structures, 2 rings are benzene rings where that are connected to each other through a 3-carbon chain. Naringin contains this basic flavonoid structure where there is one rhamnose and one glucose unit that is attached to the aglucone portion of this substance (also named as naringenin), which occurs at the carbon-7 position.

When considering the uses of this substance, it is mainly useful as a sweetener because when this substance is treated with KOH (potassium hydroxide), followed by the catalytical hydrogenation, it gives a naringin dihydrochalcone. This resulting product is roughly 300 to 1800 times sweeter than normal sugar.

However, due to the inhibition of some drug-metabolizing cytochrome P450 enzymes by this substance, it is considered a toxic compound at high concentrations. The toxic dose of naringin in rodents is around 2000 mg/kg. Usually, grapefruit juice contains about 400 mg/L.

What is Naringenin?

Naringenin is a flavorless and colorless flavanone substance. It is a type of flavonoid and occurs as the predominant flavanone in grapefruit. We can also find this substance in various fruits and herbs, including grapefruit, bergamot, sour orange, tart cherries, tomatoes, etc. The metabolism of this substance occurs in the presence of naringenin 8-dimethylallyltranferase enzyme.

If we look at the chemical structure of naringenin, it has a skeleton structure of a typical flavanone having three -OH groups at the 4, 5 and 7 carbon positions. We can find this substance in two forms: in its aglycol form or in its glycosidic form.

When considering the biological activity of naringenin, it has antimicrobial effects on some microbes; can reduce hepatitis C virus production by the infected hepatocyte cells in cell culture; have significant antioxidant properties and anticancer properties, etc.

What are the Similarities Between Naringin and Naringenin?

• Naringin and Naringenin are flavanone substances.
• Both are organic compounds containing three-ring structures per molecule.

What is the Difference Between Naringin and Naringenin?

Naringin is a type of flavonoid that occurs naturally in citrus fruits. Naringenin is a flavorless and colorless flavanone substance. The key difference between naringin and naringenin is that naringin has a bitter taste, whereas naringenin is tasteless and colorless. Moreover, naringin mainly occurs in citrus fruits, including grapefruit, whereas naringenin occurs in many fruits and herbs, including grapefruit, bergamot, sour orange, tart cherries, tomatoes, etc.

Below is a summary of the difference between naringin and naringenin in tabular form.

Summary – Naringin vs Naringenin

Naringin is a type of flavonoid that occurs naturally in citrus fruits, while naringenin is a flavorless and colorless flavanone substance. The key difference between naringin and naringenin is that naringin has a bitter taste whereas naringenin is tasteless and colorless.

Reference:

1. “Naringin.” Wikipedia, Wikimedia Foundation, 23 Mar. 2021, Available here.

Image Courtesy:

1. “Naringin” By Yikrazuul – Own work (Public Domain) via Commons Wikimedia
2. “Naringenin” By Yikrazuul – Own work (Public Domain) via Commons Wikimedia