Naringin

Structural formula
General
Surname	Naringin
other names	Aurantiin; 7 - {[2- O - (α- L -Rhamnopyranosyl) -β- D -glucopyranosyl] oxy} -2,3-dihydro-5-hydroxy-2- (4-hydroxyphenyl) -4 H -1-benzopyran- 4-on; 4 ', 5,7-trihydroxyflavanone-7-rhamnoglucoside; 4 ', 5,7-trihydroxyflavanone-7-neohesperidoside;
Molecular formula	C 27 H 32 O 14
Brief description	beige solid
External identifiers / databases
EC number	233-566-4
ECHA InfoCard	100.030.502
PubChem	442428
ChemSpider	390868
Wikidata	Q418469
properties
Molar mass	580.54 g mol −1
Physical state	firmly
Melting point	171 ° C (dihydrate)
solubility	heavy in water (1 g l −1 at 40 ° C); soluble in ethanol and acetone;
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 .

Naringin is a glycoside found in grapefruit , grapefruit and pomelos, which gives them their bitter taste. Naringin and its aglycon Naringenin belong to the group of natural polyphenols . These mainly have antioxidant and lipid-lowering effects.

Occurrence

The bitter-tasting naringin is the quantitatively most important Flavanonglycosid addition to a variety of other flavan - derivatives of grapefruit ( Citrus paradisi ) and their varieties.

Grapefruit, here with red pulp
Grapefruit with white pulp
Pomelo

The quantities given for grapefruit are in the range of 100–800 ppm ; in oranges, lemons and limes, however, naringin is only detectable in traces.

Drug interactions

In the body, naringin is metabolized by bacterial enzymes to the aglycon naringenin and naringin glucuronides . Naringin has no direct influence on the effectiveness of drugs . The breakdown products can - together with other ingredients of grapefruit, such as 6 ', 7'-dihydroxybergamottine and bergamottine - increase the effects and side effects of some drugs, since it inhibits various subtypes of cytochrome P450 ( CYP3A4 , CYP1A2 and CYP2A6 ). This slows down the breakdown of the active substances in the body by the cytochrome P450. Other drugs can also be less effective.

Individual evidence

↑ ^a ^b ^c Datasheet Naringin from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
↑ ^a ^b ^c Entry on Naringin. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
↑ Peterson, J., Beecher, GR, Bhagwat, SA, Dwyer, J., Eldridge, A., Gebhardt, SE, Haytowitz, DB, Holden, JM 2006. Flavanones in oranges, tangerines (mandarins), tangors, and tangelos : a compilation and review of the data from the analytical literature. In: J. Food Comp. Anal. 19: S66-S73.
↑ B. Staub: Medicines and Grapefruit Juice , January 7, 1997.

[Sigma-1] Datasheet Naringin from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).

[Römpp-2] Entry on Naringin. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.

[3] Peterson, J., Beecher, GR, Bhagwat, SA, Dwyer, J., Eldridge, A., Gebhardt, SE, Haytowitz, DB, Holden, JM 2006. Flavanones in oranges, tangerines (mandarins), tangors, and tangelos : a compilation and review of the data from the analytical literature. In: J. Food Comp. Anal. 19: S66-S73.

[Grapefruitsaft-4] B. Staub: Medicines and Grapefruit Juice , January 7, 1997.