Naringenin

Structural formula
General
Surname	Naringenin
other names	( S ) -5,7-dihydroxy-2- (4-hydroxyphenyl) chroman-4-one
Molecular formula	C 15 H 12 O 5
Brief description	beige solid
External identifiers / databases
EC number	207-550-2
ECHA InfoCard	100.006.865
PubChem	439246
ChemSpider	388383
DrugBank	DB03467
Wikidata	Q418374
properties
Molar mass	272.26 g mol −1
Physical state	firmly
Melting point	251 ° C
solubility	poor in water (475 mg l −1 at 25 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naringenin is a flavonoid that is found mainly in citrus plants , especially grapefruit . It is the aglycon of the glycoside naringin , a bitter substance that is responsible for the bitter taste of grapefruit. After splitting in the stomach, naringenin is produced.

Grapefruit, here with red pulp

Grapefruit with white pulp

effect

This substance can affect the way drugs work because it has an inhibitory effect on the degrading enzymes . This increases the effectiveness of the drugs. Even small amounts of fruit, juice and other preparations made from grapefruit can trigger this reaction. Affected are u. a. Calcium antagonists , ciclosporin , protease inhibitors , terfenadine , midazolam , estrogens and caffeine .

Naringenin inhibits, among other things, an isoform of cytochrome P450 , CYP1A2 .

Individual evidence

↑ Naringenin data sheet (PDF) from Carl Roth , accessed on December 14, 2010.

↑ ^a ^b Entry on naringenin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ ^a ^b data sheet (±) -Naringenin from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).

^ Petra Zagermann-Muncke: Grapefruit and Medicines . In: Pharmaceutical newspaper. Volume 31, 2005.

↑ Beat Staub: Medicines and Grapefruit Juice . In: pharma criticism. Year 18, 1997, number 7, PK417.

↑ drove. U. et al. (1993): Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. In: Br. J. Clin. Pharmacol. Vol. 35, pp. 431-436. PMID 8485024 .

[ROTH-1] Naringenin data sheet (PDF) from Carl Roth , accessed on December 14, 2010.

[ChemIDplus-2] Entry on naringenin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] ta sheet (±) -Naringenin from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).

[4] Petra Zagermann-Muncke: Grapefruit and Medicines . In: Pharmaceutical newspaper. Volume 31, 2005.

[5] Beat Staub: Medicines and Grapefruit Juice . In: pharma criticism. Year 18, 1997, number 7, PK417.

[6] rove. U. et al. (1993): Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. In: Br. J. Clin. Pharmacol. Vol. 35, pp. 431-436. PMID 8485024 .