Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.
The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs.
Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications. |
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InChI=1S/C15H12O5/c16- 9- 3- 1- 8(2- 4- 9) 13- 7- 12(19) 15- 11(18) 5- 10(17) 6- 14(15) 20- 13/h1- 6,13,16- 18H,7H2/t13- /m0/s1 |
FTVWIRXFELQLPI-ZDUSSCGKSA-N |
Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O)cc(O)cc2O1 |
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Pittocaulon velatum
(IPNI:238587-1)
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Found in
root
(BTO:0001188).
Methanol extract of dried and ground stems and roots
See:
PubMed
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Pittocaulon velatum
(IPNI:238587-1)
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Found in
stem
(BTO:0001300).
Methanol extract of dried and ground stems and roots
See:
PubMed
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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expectorant
Compounds that are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing. Compare with mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration, and antitussives, which suppress the cough reflex.
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View more via ChEBI Ontology
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
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(−)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
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IUBMB
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(−)-(2S)-naringenin
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IUBMB
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(-)-(2S)-Naringenin
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KEGG COMPOUND
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(2S)-Naringenin
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KEGG COMPOUND
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(2S)-naringenin
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UniProt
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(S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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IUBMB
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4',5,7-trihydroxyflavanone
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ChEBI
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4',5,7-Trihydroxyflavanone
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KEGG COMPOUND
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Naringenin
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KEGG COMPOUND
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NARINGENIN
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PDBeChem
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naringetol
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HMDB
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pelargidanon
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HMDB
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salipurpol
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HMDB
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480-41-1
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CAS Registry Number
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ChemIDplus
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90699
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Reaxys Registry Number
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Reaxys
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Lin BQ, Li PB, Wang YG, Peng W, Wu Z, Su WW, Ji H (2008) The expectorant activity of naringenin. Pulmonary pharmacology & therapeutics 21, 259-263 [PubMed:17664077] [show Abstract] The expectorant activity of naringenin was studied. Mucus secretion was evaluated in mice by measuring the tracheal output of phenol red. Mucociliary movement function was investigated using a migration method of carbon granules in unanesthetized pigeons. And the effect of naringenin on the secretion of mucin and lysozyme was performed in the rat tracheal ring explants. Naringenin could significantly increase the secretion of phenol red from mouse tracheas at the doses of 30-67 mg/kg (i.g.) (P<0.05). Naringenin, at the dose of 90 mg/kg, increased the tracheal mucociliary velocity (TMV) to 144.4% of control (P<0.01). 100 microM naringenin could enhance the basal lysozyme secretion, but had no effect on the basal mucin secretion from the rat tracheal ring explants. Treatment with naringenin at higher concentration (10 micromol/l) could inhibit the 100 ng/ml lipopolysaccharide (LPS)-induced mucin increase. These data suggest, therefore, that naringenin has the expectorant activity. | Felgines C, Texier O, Morand C, Manach C, Scalbert A, Régerat F, Rémésy C (2000) Bioavailability of the flavanone naringenin and its glycosides in rats. American journal of physiology. Gastrointestinal and liver physiology 279, G1148-54 [PubMed:11093936] [show Abstract] Naringenin, the predominant flavanone in grapefruit, mainly occurs as glycosides such as naringenin-7- rhamnoglucoside or naringenin-7-glucoside. This study compared kinetics of absorption of naringenin and its glycosides in rats either after a single flavanone-containing meal or after adaptation to a diet for 14 days. Regardless of the diet, circulating metabolites were glucurono- and sulfoconjugated derivatives of naringenin. The kinetics of absorption of naringenin and naringenin-7-glucoside were similar, whereas naringenin-7-rhamnoglucoside exhibited a delay in its intestinal absorption, resulting in decreased bioavailability. After naringenin-7-glucoside feeding, no glucoside was found in the cecum. However, after feeding naringenin-7-rhamnoglucoside, some naringenin-7-rhamnoglucoside accumulated in cecum before being hydrolyzed by intestinal microflora. Adaptation to flavanone diets did not induce accumulation of plasma naringenin. Moreover, flavanone cecal content markedly decreased after adaptation, and almost no naringenin-7-rhamnoglucoside was recovered after naringenin-7-rhamnoglucoside feeding, suggesting that an adaptation of cecal microflora had occurred. Overall, these data indicate that flavanones are efficiently absorbed after feeding to rats and that their bioavailability is related to their glycosidic moiety. |
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