Naringin

Not to be confused with Naringenin.
Naringin
Names
IUPAC name
7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Naringin
Naringoside
4',5,7-Trihydroxyflavanone-7-rhamnoglucoside
Naringenin 7-O-neohesperidoside
Identifiers
10236-47-2 YesY
ChEBI CHEBI:28819 N
ChEMBL ChEMBL451512 N
ChemSpider 4447695 YesY
4738
Jmol interactive 3D Image
PubChem 442428
UNII N7TD9J649B YesY
Properties
C27H32O14
Molar mass 580.54 g/mol
Melting point 166 °C (331 °F; 439 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Naringin is a flavanone-7-O-glycoside between the flavanone Naringenin and the disaccharide neohesperidose. The flavonoids naringenin and hesperetin, which form the aglycones of naringin and hesperidin, occur naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans the naringin is metabolized to the flavanone naringenin.

Biological activity

Naringin inhibits some drug-metabolizing cytochrome P450 enzymes, including CYP3A4 and CYP1A2, which may result in drug-drug interactions.[1][2] Ingestion of naringin and related flavonoids can also affect the intestinal absorption of certain drugs, leading to either an increase or decrease in circulating drug levels. To avoid interference with drug absorption and metabolism, the consumption of citrus (especially grapefruit) and other juices with medications is contraindicated.[3]

A variety of other pharmacological effects have been observed in vitro or in animal studies, but their relevance to human health in unknown. These effects include:

Uses

When naringin is treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes a naringin dihydrochalcone, a compound roughly 300–1800 times sweeter than sugar at threshold concentrations.[8]

References

  1. ↑ Ho PC, Saville DJ, Wanwimolruk S (2001). "Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds". J Pharm Pharm Sci 4 (3): 217–227. PMID 11737987.
  2. ↑ Fuhr U, Kummert AL (1995). "The fate of naringin in humans: a key to grapefruit juice-drug interactions?". Clin Pharmacol Ther 58 (4): 365–373. doi:10.1016/0009-9236(95)90048-9. PMID 7586927.
  3. ↑ "BBC NEWS, Health, Fruit juice 'could affect drugs'". 2008-08-20. Retrieved 2008-08-25.
  4. ↑ Schindler R, Mentlein R (2006). "Flavonoids and Vitamin E Reduce the Release of the Angiogenic Peptide Vascular Endothelial Growth Factor from Human Tumor Cells". The Journal of Nutrition 136 (6): 1477–82. PMID 16702307.
  5. ↑ Kandhare AD, Raygude KS, Ghosh P, Ghule AE, Bodhankar SL (2012). "Neuroprotective Effect of Naringin by Modulation of Endogenous Biomarkers in Streptozotocin Induced Painful Diabetic Neuropathy". Fitoterapia 83 (4): 650–9. doi:10.1016/j.fitote.2012.01.010. PMID 22343014.
  6. ↑ Sachdeva AK, Kuhad A, Chopra K. Naringin ameliorates memory deficits in experimental paradigm of Alzheimer's disease by attenuating mitochondrial dysfunction. Pharmacology, biochemistry, and behavior. 2014;127:101-10
  7. ↑ Kumar A, Dogra S, Prakash A (2010). "Protective Effect of Naringin, a Citrus Flavonoid, against Colchicine-Induced Cognitive Dysfunction and Oxidative Damage in Rats". Journal of Medicinal Food 13 (4): 976–84. doi:10.1089/jmf.2009.1251. PMID 20673063.
  8. ↑ Tomasik P, ed. (2004). Chemical and Functional Properties of Food Saccharides. Boca Raton: CRC Press. p. 389. ISBN 0-84-931486-0. LCCN 2003053186.
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