Naringin
| Naringin | |
|---|---|
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| 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 | |
| Identifiers | |
| CAS number | 10236-47-2  |
| PubChem | 442428 |
| ChemSpider | 4447695 |
| UNII | N7TD9J649B |
| ChEBI | CHEBI:28819  |
| Jmol-3D images | {{#if:O=C4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C)cc5O[C@H](c3ccc(O)cc3)C4|Image 1 |
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| Properties | |
| Molecular formula | C27H32O14 |
| Molar mass | 580.53 g mol−1 |
| Melting point | 166 °C; 331 °F; 439 K |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Naringin is a flavanone glycoside. It is a major flavonoid in grapefruit and gives the grapefruit juice its bitter taste. It is metabolized to the flavanone naringenin in humans. Both naringenin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. In commercial grapefruit juice production, the enzyme naringinase is used to remove the bitterness created by naringin.
Biological activity
Naringin inhibits some drug-metabolizing cytochrome P450 enzymes, including CYP3A4 and CYP1A2, which may result in drug-drug interactions.[1] 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.[2]
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:
- Naringin is an inhibitor of vascular endothelial growth factor (VEGF) release, which causes angiogenesis.[3]
- Naringin reduced diabetes-induced neuropathy in rats.[4]
- Naringin has shown protective effects on cognition and oxidative damage in rats.[5]
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.[6]
References
- ↑ Grapefruit Juice and Medications
- ↑ "BBC NEWS, Health, Fruit juice 'could affect drugs'". 2008-08-20. Retrieved 2008-08-25.
- ↑ Schindler R, Mentlein R (June 2006). "Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells". J. Nutr. 136 (6): 1477–82. PMID 16702307.
- ↑ Kandhare AD, Raygude KS, Ghosh P, Ghule AE, Bodhankar SL (June 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.
- ↑ 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): 976–984. doi:10.1089/jmf.2009.1251. PMID 20673063.
- ↑ Tomasik, Piotr (2004). Chemical and functional properties of food saccharides. Boca Raton: CRC Press. p. 389. ISBN 0-8493-1486-0.
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