Naringeninのソースを表示

{{Short description|Main polyphenol in grapefruit}}
{{Distinguish|naringin}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 414759730
<!-- Images -->
| ImageFile = Naringenin.svg
| ImageSize = 200
| ImageFile2 = Naringenin 3D BS.png
| ImageSize2 = 200
<!-- Names -->
| IUPACName = (2''S'')-4′,5,7-Trihydroxyflavan-4-one
| SystematicName = (2''S'')-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4''H''-1-benzopyran-4-one
| OtherNames = Naringetol; Salipurol; Salipurpol
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 480-41-1
| CASNo_Ref = {{cascite|correct|??}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB03467
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 50202
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = HN5425SBF2
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00509
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 9352
| PubChem = 439246
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 388383
| SMILES = O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FTVWIRXFELQLPI-ZDUSSCGKSA-N
  }}
| Section2 = {{Chembox Properties
| C=15 | H=12 | O=5
| Appearance = 
| Density = 
| MeltingPtC = 251
| MeltingPt_ref =<ref>{{HMDB|0002670}}</ref>
| BoilingPt = 
| Solubility = 475 mg/L{{citation needed|date=January 2024}}
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}

'''Naringenin''' is a [[flavanone]] from the [[flavonoid]] group of [[polyphenol]]s.<ref name="lpi">{{cite web |title=Flavonoids |url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/flavonoids |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University |access-date=9 May 2024 |date=2024}}</ref> It is commonly found in citrus fruits, especially as the predominant flavonone in [[grapefruit]].<ref name=lpi/> 

The fate and biological functions of naringenin [[in vivo]] are unknown, remaining under preliminary research, as of 2024.<ref name=lpi/> High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.<ref name=lpi/> Taking [[dietary supplement]]s or consuming grapefruit excessively may impair the action of [[anticoagulant]]s and increase the toxicity of various [[prescription drug]]s.<ref name=lpi/> 

Similar to [[furanocoumarin]]s present in citrus fruits, naringenin may evoke [[CYP3A4]] suppression in the liver and intestines, possibly resulting in adverse [[Grapefruit–drug interactions|interactions]] with common medications.<ref name=lpi/><ref>{{Cite journal |last1=Lohezic-Le Devehat |first1=F. |last2=Marigny |first2=K. |last3=Doucet |first3=M. |last4=Javaudin |first4=L. |date=2002 |title=[Grapefruit juice and drugs: a hazardous combination?]|journal=Therapie |volume=57 |issue=5 |pages=432–445 |issn=0040-5957 |pmid=12611197}}</ref><ref>{{Cite journal |last=Singh |first=B. N. |date=September 1999 |title=Effects of food on clinical pharmacokinetics |journal=Clinical Pharmacokinetics |volume=37 |issue=3 |pages=213–255 |doi=10.2165/00003088-199937030-00003 |issn=0312-5963 |pmid=10511919}}</ref><ref>{{Cite journal |last=Fuhr |first=U. |date=April 1998 |title=Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance |url=https://pubmed.ncbi.nlm.nih.gov/9565737/ |journal=Drug Safety |volume=18 |issue=4 |pages=251–272 |doi=10.2165/00002018-199818040-00002 |issn=0114-5916 |pmid=9565737}}</ref>