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Revision as of 08:42, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wiki← Previous edit		Latest revision as of 07:14, 22 June 2024 edit undoWOSlinker (talk | contribs)Administrators858,302 editsm remove nowiki
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			{{Distinguish|Naringenin}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 444021803
			| Watchedfields = changed
⚫	| Name = Naringin
		⚫	| verifiedrevid = 444022951
⚫	| ImageFile = Naringin.svg
	| ImageSize = 250px		| Name = Naringin
	| ImageName = Naringin		| ImageFile = Naringin.svg
			| ImageSize = 250px
	| IUPACName = 7-]oxy]-2,3-dihydro-5-hydroxy-<br />2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
		⚫	| ImageName = Naringin
⚫	| OtherNames = Naringin<br>Naringoside<br>4',5,7-Trihydroxyflavanone-7-rhamnoglucoside<br>4',5,7-Trihydroxyflavanone-7-]
			| ImageFile2 = Naringin 3D BS.png
⚫	| Section1 = {{Chembox Identifiers
	| PubChem = 442428		| ImageSize2 = 250px
		⚫	| ImageName2 = Naringin 3D
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| IUPACName = (2''S'')-4′,5-Dihydroxy-7-flavan-4-one
			| SystematicName = (2''S'')-7-{oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4''H''-1-benzopyran-4-one
		⚫	| OtherNames = Naringin<br>Naringoside<br>4′,5,7-Trihydroxyflavanone-7-rhamnoglucoside<br><!-- 4′,5,7-Trihydroxyflavanone-7-] -->Naringenin 7-''O''-neohesperidoside
		⚫	|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 4738
			| PubChem = 442428
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 28819
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 451512
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4447695		| ChemSpiderID = 4447695
	| InChI = 1/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1		| InChI = 1/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = DFPMSGMNTNDNHN-CSIAVLANSA-N		| StdInChIKey = DFPMSGMNTNDNHN-CSIAVLANSA-N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 10236-47-2		| CASNo = 10236-47-2
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = N7TD9J649B		| UNII = N7TD9J649B
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C09789
	| SMILES = O=C4c5c(O)cc(O2O(CO)(O)(O)2O1O((O)(O)1O)C)cc5O(c3ccc(O)cc3)C4		| SMILES = O=C4c5c(O)cc(O2O(CO)(O)(O)2O1O((O)(O)1O)C)cc5O(c3ccc(O)cc3)C4
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=27 | H=32 | O=14
	| Formula = C<sub>27</sub>H<sub>32</sub>O<sub>14</sub>
	| MolarMass = 580.54 g/mol		| MolarMass = 580.54 g/mol
			| Density =
	| ExactMass = 580.179206
			| MeltingPtC = 166
	| Density = <!-- ? g/cm<sup>3</sup> -->
	| MeltingPt = 166 °C
	}}		}}
	}}		}}
			'''Naringin''' is a ]-7-''O''-] between the flavanone ] and the ] ]. The ] naringin occurs naturally in ]s, especially in ], where naringin is responsible for the fruit's bitter taste. In commercial ] production, the enzyme ] can be used to remove the bitterness ('''debittering''') created by naringin.<ref>{{cite journal |doi=10.1039/c3cs35506c |title=Industrial use of immobilized enzymes |date=2013 |vauthors=Dicosimo R, McAuliffe J, Poulose AJ, Bohlmann G |journal=Chemical Society Reviews |volume=42 |issue=15 |pages=6437–6474 |pmid=23436023 }}</ref> In humans naringin is metabolized to the aglycone naringenin (not bitter) by naringinase present in the gut.
	'''Naringin''' is a ]. It is a major flavonoid in ] and gives the ] its bitter taste. It is metabolized to the ] ] in humans. Both ] and ], which are the ]s of naringin and ], occur naturally in ].
	==Activity==		==Structure==
			Naringin belongs to the ] family. Flavonoids consist of 15 carbon atoms in 3 rings, 2 of which must be ] rings connected by a 3 carbon chain. Naringin contains the basic flavonoid structure along with one ] and one ] unit attached to its ] portion, called ], at the 7-carbon position. The ] provided by the two sugar units makes naringin less potent than its ] counterpart, naringenin.<ref name=":0">{{Cite journal|vauthors=Alam MA, Subhan N, Rahman MM, Uddin SJ, Reza HM, Sarker SD|date=July 2014|title=Effect of Citrus Flavonoids, Naringin and Naringenin, on Metabolic Syndrome and Their Mechanisms of Action|url=http://advances.nutrition.org/content/5/4/404|journal=Advances in Nutrition|language=en|volume=5|issue=4|pages=404–417|doi=10.3945/an.113.005603|issn=2156-5376|pmc=4085189|pmid=25022990}}</ref>
⚫	Naringin exerts a variety of pharmacological effects such as ] activity, blood ] lowering, ] activity, and ] of selected drug-metabolizing ] ]s, including ] and ], which may result in drug-drug interactions ''in vivo''.<ref></ref> Ingestion of naringin and related flavonoids can also affect the intestinal absorption of certain drugs, leading to either an increase or decrease in circulating drug levels. To avoid interference with drug absorption and metabolism, the consumption of citrus (esp. grapefruit) and other juices with medications is contraindicated.
	<ref>
	{{Cite web
	| title = BBC NEWS, Health, Fruit juice 'could affect drugs'
	| accessdate = 2008-08-25
	| url = http://newsvote.bbc.co.uk/mpapps/pagetools/print/news.bbc.co.uk/2/hi/health/7572500.stm
	| date=2008-08-20}}
	</ref>
			]
	Naringin, followed by ], was the most potent flavonoid inhibitor of ] release, which causes ], out of 21 flavonoids.<ref>{{cite journal |author=Schindler R, Mentlein R |title=Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells |journal=J. Nutr. |volume=136 |issue=6 |pages=1477–82 |year=2006 |month=June |pmid=16702307 |url=http://jn.nutrition.org/cgi/content/full/136/6/1477}}</ref>
	== Use ==		===Metabolism===
			In humans, ] is found in the liver and rapidly metabolizes naringin into ]. This happens in two steps: first, naringin is hydrolyzed by α-<small>L</small>-rhamnosidase activity of naringinase to ] and ]. The prunin formed is then hydrolyzed by β-<small>D</small>-glucosidase activity of naringinase into naringenin and ].<ref name=":1" /> ] is an enzyme that has a wide occurrence in nature and can be found in plants, yeasts, and fungi. It is commercially attractive due to its debittering properties.<ref name=":1">{{Cite journal|vauthors=Ribeiro MH|date=June 2011|title=Naringinases: occurrence, characteristics, and applications|journal=Applied Microbiology and Biotechnology|language=en|volume=90|issue=6|pages=1883–1895|doi=10.1007/s00253-011-3176-8|pmid=21544655|s2cid=1653069 |issn=0175-7598}}</ref>
⚫	When naringin is treated with ] or another strong base, and then ] ], it becomes a ], a compound roughly 300-1800 times sweeter than sugar at threshold concentrations<ref name=Tomasik-2003>{{cite book |author=Tomasik, Piotr |title=Chemical and functional properties of food saccharides |publisher=CRC Press |location=Boca Raton |year=2004 |page=389 |isbn=0-8493-1486-0 }}<!--Please fix the quote if you have it--></ref>.
			==Toxicity==
			The typical concentration of naringin in grapefruit juice is around 400&nbsp;mg/L.<ref>{{Cite journal|title=Naringin content in local citrus fruits |language=en|doi=10.1016/0308-8146(90)90085-I|volume=37|issue=2|journal=Food Chemistry|pages=113–121 | vauthors = Yusof S|date=January 1990 }}</ref> The reported ] of naringin in rodents in 2000&nbsp;mg/kg.<ref>{{Cite web|url=https://www.mdidea.com/products/herbextract/naringin/data07.html|title=Naringin: Safety and Acute toxicity.|website=www.mdidea.com|language=en|access-date=2017-05-08}}</ref>
		⚫	Naringin ] some drug-metabolizing ] ]s, including ] and ], which may result in drug-drug interactions.<ref>{{cite journal|date=1995|title=The fate of naringin in humans: a key to grapefruit juice-drug interactions?|journal=Clinical Pharmacology & Therapeutics|volume=58|issue=4|pages=365–373|doi=10.1016/0009-9236(95)90048-9|pmid=7586927|vauthors=Fuhr U, Kummert AL|s2cid=21372946 }}</ref> Ingestion of naringin and related flavonoids can also affect the intestinal absorption of certain drugs, leading to either an increase or decrease in circulating drug levels. To avoid interference with drug absorption and metabolism, the consumption of citrus (especially grapefruit) and other juices with medications is advised against.<ref>{{Cite news|url=http://news.bbc.co.uk/1/hi/health/7572500.stm|website=BBC News |title=Fruit juice 'could affect drugs'|date=August 20, 2008|accessdate=2022-05-28}}</ref>
			However, ] studies have also shown that naringin in grapefruit is not what causes the inhibitory effects associated with grapefruit juice. Naringin solution when compared to grapefruit solution produced much less inhibition of ].<ref name=":2">{{Cite journal|vauthors=Edwards DJ, Bernier SM|date=January 1996|title=Naringin and naringenin are not the primary CYP3A inhibitors in grapefruit juice|journal=Life Sciences|volume=59|issue=13|pages=1025–1030|issn=0024-3205|pmid=8809221|doi=10.1016/0024-3205(96)00417-1}}</ref> Furthermore, ] juice, which contains considerably less naringin content than grapefruit juice, was found to produce the same level of inhibition of CYP3A4 as grapefruit juice. This would suggest that an inhibitor other than naringin, such as ], which is also found in Seville oranges, may be at work.<ref name=":2" /> At the same time, naringenin is known to be a more potent inhibitor of CYP3A4/5 than naringin <ref>{{Cite journal|vauthors=Lundahl J, Regårdh CG, Edgar B, Johnsson G|date=January 1997|title=Effects of grapefruit juice ingestion—pharmacokinetics and haemodynamics of intravenously and orally administered felodipine in healthy men|journal=European Journal of Clinical Pharmacology|volume=52|issue=2|pages=139–145|issn=0031-6970|pmid=9174684|doi=10.1007/s002280050263|s2cid=22705973 }}</ref> and in vitro studies have been unable to effectively convert naringin into naringenin. This leaves open the possibility that in vivo, naringin converted into naringenin by naringinase is what causes the inhibitory effect on CYP3A4.<ref name=":2" /> Due to the contradictory results of the effect of naringin it is hard to tell whether it is naringin itself or other components of grapefruit juice that cause ] and lead to its toxicity.
			== Uses==
			===Commercial===
		⚫	When naringin is treated with ] or another strong base, and then ] ], it becomes a ], a compound roughly 300–1800 times sweeter than sugar at threshold concentrations.<ref name=Tomasik-2003>{{ cite book | editor = Tomasik P | title = Chemical and Functional Properties of Food Saccharides | publisher = CRC Press | location = Boca Raton | year = 2004 | page = 389 | isbn = 978-0-84-931486-5 | lccn = 2003053186 }}<!--Please fix the quote if you have it--></ref>
	==References==		==References==
	{{reflist}}		{{reflist}}
			==External links==
			*{{Commons category-inline}}
	{{Flavanone}}		{{Flavanone}}
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			]
	]		]
	]
	]
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	]
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	]
	]
	]