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
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| 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>

== Structure ==
Naringenin has the skeleton structure of a flavanone with three [[hydroxy group]]s at the 4′, 5, and 7 carbons.<ref name=lpi/> It may be found both in the [[Aglycone|aglycol]] form, naringenin, or in its [[Glycoside|glycosidic]] form, [[naringin]], which has the addition of the [[disaccharide]] [[neohesperidose]] attached via a [[Glycosidic bond|glycosidic]] linkage at carbon 7.

Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.<ref name="Yáñez 159–181">{{cite journal | vauthors = Yáñez JA, Andrews PK, Davies NM | title = Methods of analysis and separation of chiral flavonoids | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 848 | issue = 2 | pages = 159–181 | date = April 2007 | pmid = 17113835 | doi = 10.1016/j.jchromb.2006.10.052 }}</ref><ref name=":0">{{cite journal | vauthors = Yáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM | title = Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices | journal = Biopharmaceutics & Drug Disposition | volume = 29 | issue = 2 | pages = 63–82 | date = March 2008 | pmid = 18058792 | doi = 10.1002/bdd.588 | s2cid = 24051610 }}</ref> [[Racemization]] of (''S'')-(−)-naringenin has been shown to occur fairly quickly.<ref name="Krause 69–72">{{Cite journal| vauthors = Krause M, Galensa R |date = July 1991 |title=Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase|journal=Chromatographia|language=en|volume=32|issue=1–2|pages=69–72|doi=10.1007/BF02262470|s2cid=95215634|issn=0009-5893}}</ref>

== Sources and bioavailability==
Naringenin and its glycoside has been found in a variety of [[herb]]s and [[fruit]]s, including [[grapefruit]], oranges, and lemons,<ref name=lpi/> [[Bitter orange|sour orange]],<ref>{{cite journal | vauthors = Gel-Moreto N, Streich R, Galensa R | title = Chiral separation of diastereomeric flavanone-7-''O''-glycosides in citrus by capillary electrophoresis | journal = Electrophoresis | volume = 24 | issue = 15 | pages = 2716–2722 | date = August 2003 | pmid = 12900888 | doi = 10.1002/elps.200305486 | s2cid = 40261445 }}</ref> [[Prunus cerasus|sour cherries]],<ref name=":4">{{cite journal | vauthors = Wang H, Nair MG, Strasburg GM, Booren AM, Gray JI | title = Antioxidant polyphenols from tart cherries (''Prunus cerasus'') | journal = Journal of Agricultural and Food Chemistry | volume = 47 | issue = 3 | pages = 840–844 | date = March 1999 | pmid = 10552377 | doi = 10.1021/jf980936f }}</ref> [[tomato]]es,<ref>{{cite journal | vauthors = Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P, Martín Belloso O | title = Changes in the polyphenol profile of tomato juices processed by pulsed electric fields | journal = Journal of Agricultural and Food Chemistry | volume = 60 | issue = 38 | pages = 9667–9672 | date = September 2012 | pmid = 22957841 | doi = 10.1021/jf302791k | author-link6 = Olga Martín-Belloso }}</ref> [[Cocoa bean|cocoa]],<ref>{{cite journal | vauthors = Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM | title = Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (''Theobroma cacao'') | journal = Journal of Mass Spectrometry | volume = 38 | issue = 1 | pages = 35–42 | date = January 2003 | pmid = 12526004 | doi = 10.1002/jms.395 | bibcode = 2003JMSp...38...35S }}</ref> [[Salvia fruticosa|Greek oregano]],<ref>{{cite journal | vauthors = Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J | title = LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano | journal = Analytical Chemistry | volume = 75 | issue = 22 | pages = 6288–6294 | date = November 2003 | pmid = 14616013 | doi = 10.1021/ac0347819 }}</ref> [[Mentha aquatica|water mint]],<ref>{{cite journal | vauthors = Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK | title = Isolation of the MAO-inhibitor naringenin from Mentha aquatica L | journal = Journal of Ethnopharmacology | volume = 117 | issue = 3 | pages = 500–502 | date = May 2008 | pmid = 18372132 | doi = 10.1016/j.jep.2008.02.015 }}</ref> as well as in [[bean]]s.<ref>{{cite journal | vauthors = Hungria M, Johnston AW, Phillips DA | title = Effects of flavonoids released naturally from bean (''Phaseolus vulgaris'') on nodD-regulated gene transcription in ''Rhizobium leguminosarum'' bv. ''phaseoli'' | journal = Molecular Plant-Microbe Interactions | volume = 5 | issue = 3 | pages = 199–203 | date = 1992-05-01 | pmid = 1421508 | doi = 10.1094/mpmi-5-199 }}</ref> Ratios of naringenin to naringin vary among sources,<ref name=lpi/> as do [[enantiomeric ratio]]s.<ref name=":0" />

The naringenin-7-glucoside form seems less bioavailable than the [[aglycol]] form.<ref name="pmid10558881">{{cite journal | vauthors = Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA | title = Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation | journal = Biochemical and Biophysical Research Communications | volume = 265 | issue = 2 | pages = 410–415 | date = November 1999 | pmid = 10558881 | doi = 10.1006/bbrc.1999.1695 }}</ref>

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.<ref name="pmid11160539">{{cite journal | vauthors = Erlund I, Meririnne E, Alfthan G, Aro A | title = Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice | journal = The Journal of Nutrition | volume = 131 | issue = 2 | pages = 235–241 | date = February 2001 | pmid = 11160539 | doi = 10.1093/jn/131.2.235 | doi-access = free }}</ref>

Naringenin can be absorbed from cooked tomato paste. There are 3.8&nbsp;mg of naringenin in 150 grams of tomato paste.<ref name="pmid12421849">{{cite journal | vauthors = Bugianesi R, Catasta G, Spigno P, D'Uva A, Maiani G | title = Naringenin from cooked tomato paste is bioavailable in men | journal = The Journal of Nutrition | volume = 132 | issue = 11 | pages = 3349–3352 | date = November 2002 | pmid = 12421849 | doi = 10.1093/jn/132.11.3349 | doi-access = free }}</ref>

== Biosynthesis and metabolism ==
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.<ref name=lpi/> Naringenin is derived from [[malonyl-CoA]] and [[Coumaroyl-CoA|4-coumaroyl-CoA]].<ref name=lpi/> The latter is derived from [[phenylalanine]]. The resulting tetraketide is acted on by [[chalcone synthase]] to give the chalcone that then undergoes ring-closure to naringenin.<ref name="pmid2450022">{{cite journal | vauthors = Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, Ren Y, Li Z, Yu M | display-authors = 6 | title = Characterization of Stilbene Synthase Genes in Mulberry (''Morus atropurpurea'') and Metabolic Engineering for the Production of Resveratrol in ''Escherichia coli'' | journal = Journal of Agricultural and Food Chemistry | volume = 65 | issue = 8 | pages = 1659–1668 | date = March 2017 | pmid = 28168876 | doi = 10.1021/acs.jafc.6b05212 }}</ref>

The enzyme [[naringenin 8-dimethylallyltransferase]] uses [[dimethylallyl diphosphate]] and (−)-(2''S'')-naringenin to produce diphosphate and [[8-prenylnaringenin]]. ''[[Cunninghamella elegans]]'', a fungal model organism of the mammalian metabolism, can be used to study the naringenin [[sulfation]].<ref name="pmid10680173">{{cite journal | vauthors = Ibrahim AR | title = Sulfation of naringenin by ''Cunninghamella elegans'' | journal = Phytochemistry | volume = 53 | issue = 2 | pages = 209–212 | date = January 2000 | pmid = 10680173 | doi = 10.1016/S0031-9422(99)00487-2 | bibcode = 2000PChem..53..209I }}</ref>

==Metabolic fate and research==
The fate and biological roles of naringenin are difficult to study because naringenin is rapidly metabolized in the intestine and liver, and its metabolites are destined for excretion.<ref name=lpi/><ref name="roth">{{cite journal |vauthors=Rothwell JA, Urpi-Sarda M, Boto-Ordoñez M, Llorach R, Farran-Codina A, Barupal DK, Neveu V, Manach C, Andres-Lacueva C, Scalbert A |title=Systematic analysis of the polyphenol metabolome using the Phenol-Explorer database |journal=Molecular Nutrition & Food Research |volume=60 |issue=1 |pages=203–11 |date=January 2016 |pmid=26310602 |pmc=5057353 |doi=10.1002/mnfr.201500435}}</ref> The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound.<ref name=lpi/><ref name=roth/>

== References ==
{{Reflist}}

{{Flavanone}}
{{Phytoestrogens}}
{{Estrogen receptor modulators}}
{{Opioid receptor modulators}}
{{Progesterone receptor modulators}}

[[Category:Aromatase inhibitors]]
[[Category:Delta-opioid receptor antagonists]]
[[Category:Flavanones]]
[[Category:Resorcinols]]
[[Category:Kappa-opioid receptor antagonists]]
[[Category:Mu-opioid receptor antagonists]]
[[Category:Progestogens]]
[[Category:Phytoestrogens]]
[[Category:Histidine decarboxylase inhibitors]]
[[Category:3-Hydroxypropenals]]