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The structure and function of naringenin

Views: 0     Author: Site Editor     Publish Time: 2022-06-17      Origin: Site

Basics of flavonoid naringenin 

Naringenin is an odorless, white to yellowish flavanone that is a flavonoid. It is the main flavanone in grapefruit and is found in many fruits and herbs.

Structure of naringenin flavonoid 

Naringenin has the skeleton structure of flavanone with three hydroxyl groups at the 4', 5 and 7 carbon atoms. Naringenin can exist as a monomer, and also has a glycoside form, naringin, which has the added disaccharide neohesperidin and is connected to the 7th carbon atom.

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

Source and bioavailability of naringenin

Naringenin and its glycosides are found in a variety of herbs and fruits, including grapefruit, bergamot, lime, sour cherries, and beans. The ratio of naringenin to naringenin varies by source, as does the enantiomeric ratio.

The bioavailability of the naringin-7-glucoside form appears to be lower than that of the polyethylene glycol form.

After taking grapefruit juice, naringenin plasma concentration was higher than taking orange juice. A related compound, kaempferol, is also found in grapefruit, with the hydroxyl group next to the keto group.

Naringenin can be absorbed from cooked tomato paste. There are 253 mg of naringenin per 10 grams of tomato paste.

Naringenin's biosynthesis and metabolism

It is derived from malonyl-CoA and 4-coumaroyl-CoA. The latter is derived from phenylalanine. The obtained butenone is acted on chalcone synthase to obtain chalcone. Chalcone then undergoes ring closure to generate naringenin.

Naringenin-8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2S)-naringenin to produce diphosphate and 8-pentylnaringenin. Cunninghamella elegans, a fungal model organism for mammalian metabolism, can be used to study the sulfation of Naringenin -Jiahe

Efficacy and role of naringenin flavonoid 

1. Antibacterial, antifungal and antiviral

Naringenin has antibacterial effects on Staphylococcus epidermidis, Staphylococcus aureus, Bacillus subtilis, Xanthococcus and Escherichia coli. Further research added studies on Lactococcus lactis, Lactobacillus acidophilus, Actinomyces naesli, Prevotella oral Lactobacillus acidophilus, Propionibacterium melanin, Porphyromonas gingivalis, and Candida albicans, tropical and Grams. Evidence for antibacterial drugs such as Candida rubis. Although naringin has not been demonstrated to have any inhibitory effect on the urease activity of microorganisms, there is evidence of its antibacterial effect against Helicobacter pylori.

Naringenin can reduce the production of HCV-infected hepatocellular virus in cultured in vitro. This may be secondary to the effect of naringenin on VLDL secretion. The antiviral effect of naringin is currently under clinical research. Reports have also been published on the antiviral effects of poliovirus, HSV-1 and HSV-2, although viral replication is not inhibited.

2. Anti-inflammatory

Despite the evidence of anti-inflammatory activity of naringin, [33] it has been observed that the anti-inflammatory activity of naringin is poor or non-existent.

3. Antioxidants

Naringenin has been shown to have significant antioxidant properties. It has been shown to reduce oxidative damage to DNA in in vitro and animal studies.

4. Anti-tumor

Naringenin has been reported to induce cytotoxicity in breast, gastric, liver, cervical, pancreatic and colon cancer cells, as well as in leukemia cells. The mechanism by which naringenin inhibits the growth of human breast cancer has been confirmed. The first hypothesis is that naringenin inhibits aromatase, thereby reducing tumor growth. The second hypothesis proposes that the interaction with the estrogen receptor is responsible for its regulation of tumor growth. Novel derivatives of naringin are active against multidrug-resistant cancers.

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