J u m p t o c o n t e n t
M a i n m e n u
M a i n m e n u
N a v i g a t i o n
● M a i n p a g e
● C o n t e n t s
● C u r r e n t e v e n t s
● R a n d o m a r t i c l e
● A b o u t W i k i p e d i a
● C o n t a c t u s
● D o n a t e
C o n t r i b u t e
● H e l p
● L e a r n t o e d i t
● C o m m u n i t y p o r t a l
● R e c e n t c h a n g e s
● U p l o a d f i l e
S e a r c h
Search
A p p e a r a n c e
● C r e a t e a c c o u n t
● L o g i n
P e r s o n a l t o o l s
● C r e a t e a c c o u n t
● L o g i n
P a g e s f o r l o g g e d o u t e d i t o r s l e a r n m o r e
● C o n t r i b u t i o n s
● T a l k
( T o p )
1
S t r u c t u r e
2
S o u r c e s a n d b i o a v a i l a b i l i t y
3
B i o s y n t h e s i s a n d m e t a b o l i s m
4
M e t a b o l i c f a t e a n d r e s e a r c h
5
R e f e r e n c e s
T o g g l e t h e t a b l e o f c o n t e n t s
N a r i n g e n i n
1 8 l a n g u a g e s
● C a t a l à
● D e u t s c h
● Ε λ λ η ν ι κ ά
● E s p a ñ o l
● E s p e r a n t o
● ف ا ر س ی
● F r a n ç a i s
● 한 국 어
● I t a l i a n o
● ע ב ר י ת
● N e d e r l a n d s
● 日 本 語
● P o l s k i
● Р у с с к и й
● С р п с к и / s r p s k i
● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и
● S u o m i
● 中 文
E d i t l i n k s
● A r t i c l e
● T a l k
E n g l i s h
● R e a d
● E d i t
● V i e w h i s t o r y
T o o l s
T o o l s
A c t i o n s
● R e a d
● E d i t
● V i e w h i s t o r y
G e n e r a l
● W h a t l i n k s h e r e
● R e l a t e d c h a n g e s
● U p l o a d f i l e
● S p e c i a l p a g e s
● P e r m a n e n t l i n k
● P a g e i n f o r m a t i o n
● C i t e t h i s p a g e
● G e t s h o r t e n e d U R L
● D o w n l o a d Q R c o d e
● W i k i d a t a i t e m
P r i n t / e x p o r t
● D o w n l o a d a s P D F
● P r i n t a b l e v e r s i o n
I n o t h e r p r o j e c t s
● W i k i m e d i a C o m m o n s
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Other names
Naringetol; Salipurol; Salipurpol
100.006.865
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 N
Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N N
O=C2c3c(O[C@H](c1ccc(O )cc1)C2)cc(O )cc3O
C 15 H 12 O 5
272.256 g·mol−1
251 °C (484 °F; 524 K )[1]
475 mg/L[citation needed ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Naringenin is a flavanone from the flavonoid group of polyphenols .[2] It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit .[2]
The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024.[2] High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.[2] Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs .[2]
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.[2] [3] [4] [5]
Structure [ edit ]
Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4′, 5, and 7 carbons.[2] It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin , which has the addition of the disaccharide neohesperidose attached via a 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.[6] [7] Racemization of (S )-(−)-naringenin has been shown to occur fairly quickly.[8]
Sources and bioavailability [ edit ]
Naringenin and its glycoside has been found in a variety of herbs and fruits , including grapefruit , oranges, and lemons,[2] sour orange ,[9] sour cherries ,[10] tomatoes ,[11] cocoa ,[12] Greek oregano ,[13] water mint ,[14] as well as in beans .[15] Ratios of naringenin to naringin vary among sources,[2] as do enantiomeric ratios .[7]
The naringenin-7-glucoside form seems less bioavailable than the aglycol form.[16]
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[17]
Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste.[18]
Biosynthesis and metabolism [ edit ]
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[2] Naringenin is derived from malonyl-CoA and 4-coumaroyl-CoA .[2] 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.[19]
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 .[20]
Metabolic fate and research [ edit ]
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.[2] [21] The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound.[2] [21]
References [ edit ]
^ a b c d e f g h i j k l m "Flavonoids" . Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024 .
^ Lohezic-Le Devehat, F.; Marigny, K.; Doucet, M.; Javaudin, L. (2002). "[Grapefruit juice and drugs: a hazardous combination?]". Therapie . 57 (5 ): 432–445. ISSN 0040-5957 . PMID 12611197 .
^ Singh, B. N. (September 1999). "Effects of food on clinical pharmacokinetics". Clinical Pharmacokinetics . 37 (3 ): 213–255. doi :10.2165/00003088-199937030-00003 . ISSN 0312-5963 . PMID 10511919 .
^ Fuhr, U. (April 1998). "Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance" . Drug Safety . 18 (4 ): 251–272. doi :10.2165/00002018-199818040-00002 . ISSN 0114-5916 . PMID 9565737 .
^ Yáñez JA, Andrews PK, Davies NM (April 2007). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences . 848 (2 ): 159–181. doi :10.1016/j.jchromb.2006.10.052 . PMID 17113835 .
^ a b Yáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM (March 2008). "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices". Biopharmaceutics & Drug Disposition . 29 (2 ): 63–82. doi :10.1002/bdd.588 . PMID 18058792 . S2CID 24051610 .
^ Krause M, Galensa R (July 1991). "Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase". Chromatographia . 32 (1–2): 69–72. doi :10.1007/BF02262470 . ISSN 0009-5893 . S2CID 95215634 .
^ Gel-Moreto N, Streich R, Galensa R (August 2003). "Chiral separation of diastereomeric flavanone-7-O -glycosides in citrus by capillary electrophoresis". Electrophoresis . 24 (15 ): 2716–2722. doi :10.1002/elps.200305486 . PMID 12900888 . S2CID 40261445 .
^ Wang H, Nair MG, Strasburg GM, Booren AM, Gray JI (March 1999). "Antioxidant polyphenols from tart cherries (Prunus cerasus )". Journal of Agricultural and Food Chemistry . 47 (3 ): 840–844. doi :10.1021/jf980936f . PMID 10552377 .
^ Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P, Martín Belloso O (September 2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields". Journal of Agricultural and Food Chemistry . 60 (38 ): 9667–9672. doi :10.1021/jf302791k . PMID 22957841 .
^ Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM (January 2003). "Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao )". Journal of Mass Spectrometry . 38 (1 ): 35–42. Bibcode :2003JMSp...38...35S . doi :10.1002/jms.395 . PMID 12526004 .
^ Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (November 2003). "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". Analytical Chemistry . 75 (22 ): 6288–6294. doi :10.1021/ac0347819 . PMID 14616013 .
^ Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK (May 2008). "Isolation of the MAO-inhibitor naringenin from Mentha aquatica L". Journal of Ethnopharmacology . 117 (3 ): 500–502. doi :10.1016/j.jep.2008.02.015 . PMID 18372132 .
^ Hungria M, Johnston AW, Phillips DA (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris ) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli ". Molecular Plant-Microbe Interactions . 5 (3 ): 199–203. doi :10.1094/mpmi-5-199 . PMID 1421508 .
^ Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA (November 1999). "Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation". Biochemical and Biophysical Research Communications . 265 (2 ): 410–415. doi :10.1006/bbrc.1999.1695 . PMID 10558881 .
^ Erlund I, Meririnne E, Alfthan G, Aro A (February 2001). "Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice" . The Journal of Nutrition . 131 (2 ): 235–241. doi :10.1093/jn/131.2.235 . PMID 11160539 .
^ Bugianesi R, Catasta G, Spigno P, D'Uva A, Maiani G (November 2002). "Naringenin from cooked tomato paste is bioavailable in men" . The Journal of Nutrition . 132 (11 ): 3349–3352. doi :10.1093/jn/132.11.3349 . PMID 12421849 .
^ Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea ) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli ". Journal of Agricultural and Food Chemistry . 65 (8 ): 1659–1668. doi :10.1021/acs.jafc.6b05212 . PMID 28168876 .
^ Ibrahim AR (January 2000). "Sulfation of naringenin by Cunninghamella elegans ". Phytochemistry . 53 (2 ): 209–212. Bibcode :2000PChem..53..209I . doi :10.1016/S0031-9422(99 )00487-2 . PMID 10680173 .
^ a b Rothwell JA, Urpi-Sarda M, Boto-Ordoñez M, Llorach R, Farran-Codina A, Barupal DK, Neveu V, Manach C, Andres-Lacueva C, Scalbert A (January 2016). "Systematic analysis of the polyphenol metabolome using the Phenol-Explorer database" . Molecular Nutrition & Food Research . 60 (1 ): 203–11. doi :10.1002/mnfr.201500435 . PMC 5057353 . PMID 26310602 .
Eriodictyol
Naringenin
Pinocembrin
Hesperetin
Homoeriodictyol
Isosakuranetin
Pinostrobin (Pinocembrin-7-methylether)
Sakuranetin
Sterubin
Neoeriocitrin
Hesperidin
Liquiritin
Naringin (Narigenin 7-O-neohesperidoside)
Narirutin (Naringenin 7-O-rutinoside)
Poncirin
Prunin (Naringenin-7-O-glucoside)
Sakuranin
Isoxanthohumol
Sophoraflavanone G
Pinocembrin
7,8-Dihydroxyflavone
Mirificin
6-Prenylnaringenin
8-Geranylnaringenin
6,8-Diprenylnaringenin
Icaritin
Daidzein
Daidzin
Formononetin
Genistein
Genistin
Glycitein
Ononin
Prunetin
Puerarin
Tectorigenin
Glabridin
Phlorizin
Coumestrol
Desmethylwedelolactone
Wedelolactone
Enterolactone
Cinchonain-Ib
Miroestrol
Resveratrol
α-Isosparteine
Zearalenone
α-Zearalanol (zeranol)
α-Zearalenol
β-Zearalanol
β-Zearalenol
Atrazine
BHA
Bisphenol A
Bisphenol F
Bisphenol S
DDE
DDT
Dieldrin
Dioxins
Endosulfan
Enzacamene
Erythrosine
Heptachlor
Lindane
Methoxychlor
Nonylphenol
Parabens
PBBs
PCBs
Pentachlorophenol
PHBA
Phthalates
Propyl gallate
Perfluorinated compound
Antimony
Arsenite
Barium
Cadmium
Chromium
Cobalt
Copper
Lead
Mercury
Nickel
Selenite
Tin
Vanadate
ER Tooltip Estrogen receptor
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators )
2-Phenylbenzothiophene
4'-Hydroxynorendoxifen
27-Hydroxycholesterol
Acefluranol
Acolbifene
Afimoxifene
Anordiol
Anordrin
Arzoxifene
Bazedoxifene
Brilanestrant
Broparestrol
Camizestrant
Chlorotrianisene
Clomifene
Clomifenoxide
CN-55945-27
Cyclofenil
D-15413
Desmethylchlorotrianisene
Droloxifene
Enclomifene
Endoxifen
Etacstil (GW-5638, DPC-974)
Ethamoxytriphetol (MER-25)
Femarelle
Fispemifene
GW-7604
ICI-55548
Idoxifene
Lasofoxifene
Levormeloxifene
LN-1643
LN-2299
LY-117018
Menerba
Miproxifene
Miproxifene phosphate
MRL-37
Nafoxidine
Nitromifene
NNC 45-0095
NNC 45-0320
NNC 45-0781
NNC 45-1506
Ormeloxifene
Ospemifene
Panomifene
Pipendoxifene
Promensil
Raloxifene
Rimostil (P-081)
Spironolactone
SS1010
Tamoxifen
TAS-108 (SR-16234)
Toremifene
Trioxifene
TZE-5323
U-11555A
U-11634
Y-134
Zindoxifene
Zuclomifene
7β-Hydroxy-DHEA
Chloroindazole
Cytestrol acetate
EM-800 (SCH-57050)
Epitiostanol
ERA-90
ERB-88
Fulvestrant (ICI-182780)
Glyceollins (I , II , III , IV )
ICI-164384
MDL-101906
Mepitiostane
Methylepitiostanol
Methylpiperidinopyrazole
MIBE
Oxabicycloheptene sulfonate
Phenytoin
PHTPP
Prochloraz
RU-39411
RU-58668
SS1020
TAS-108 (SR-16234)
ZB716
ZK-164015
ZK-191703
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Aldosterone
Atrazine
Bisphenol A
Daidzein
DDT (p,p'-DDT , o',p'-DDE )
Diarylpropionitrile
Equol
Estradiol
Ethinylestradiol
Fulvestrant (ICI-182780)
G-1
Genistein
GPER-L1
GPER-L2
Hydroxytyrosol
Kepone
Niacin
Niacinamide
Nonylphenol
Oleuropein
PCBs (2,2',5'-PCB-4-OH )
Propylpyrazoletriol
Quercetin
Raloxifene
Resveratrol
STX
Tamoxifen
Tectoridin
Estriol
G-15
G-36
MIBE
Zearalenone
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
ψ-Akuammigine
α-Chlornaltrexamine
α-Narcotine
Acetyldihydrocodeine
Acetylfentanyl
Acrylfentanyl
Adrenorphin (metorphamide)
AH-7921
Akuammicine
Akuammidine
Alfentanil
Anileridine
Apparicine
β-Endorphin
BAM-12P
BAM-18P
BAM-22P
Benzhydrocodone
Benzylmorphine
Bezitramide
Biphalin
BU08070
Buprenorphine
Butorphan
Butorphanol
Butyrfentanyl
BW373U86
Carfentanil
Casokefamide
Cebranopadol
Chloroxymorphamine
Codeine
DADLE
DAMGO (DAGO)
Dermorphin
Desmetramadol (desmethyltramadol)
Desomorphine
Dextromoramide
Dextropropoxyphene (propoxyphene)
Dezocine
Dimenoxadol
Dimethylaminopivalophenone
Eluxadoline
Diamorphine (heroin)
Dihydrocodeine
Dihydroetorphine
Dihydromorphine
Dinalbuphine sebacate
Diphenoxylate
Dipipanone
Dynorphin A
Embutramide
Endomorphin-1
Endomorphin-2
Eseroline
Ethylmorphine
Etorphine
Fentanyl
Fluorophen
Frakefamide
Furanylfentanyl
Hemorphin-4
Herkinorin
Hodgkinsine
Hydrocodone
Hydromorphinol
Hydromorphone
IBNtxA
Ketamine
Ketobemidone
Kratom
Laudanosine
Lefetamine
Leu-enkephalin
Levacetylmethadol
Levomethorphan
Levorphanol
Lexanopadol
Loperamide
Loxicodegol
LS-115509
Matrine
Meptazinol
Met-enkephalin (metenkefalin)
Methadone
Metkefamide
Metopon
Mitragynine
Mitragynine pseudoindoxyl
Morphiceptin
Morphine
Nalbuphine
NalBzOH
Nalmexone
Naltalimide
Neopine
NFEPP
Nicocodeine
Nicodicodine
Nicomorphine
Norketamine
Nufenoxole
Octreotide
Oliceridine
Oxycodegol
OM-3-MNZ
Oripavine
Oxycodone
Oxymorphazone
Oxymorphonazine
Oxymorphone
Oxymorphone phenylhydrazone
OxyPNPH
Papaver somniferum (opium )
Pentazocine
Pericine
Pethidine (meperidine)
Phenazocine
Phencyclidine
Piminodine
Piritramide
PL-017
Prodine
Propiram
PZM21
Racemethorphan
Racemorphan
Remifentanil
Salsolinol
SC-17599
Sinomenine
Sufentanil
Tapentadol
Tetrahydropapaveroline
TH-030418
Thebaine
Thienorphine
Tianeptine
Tilidine
Tramadol
Trimebutine
TRIMU 5
TRV734
Tubotaiwine
U-47700
Valorphin
Viminol
Xorphanol
2-(S )-N,N-(R )-Viminol
3CS-nalmefene
4-Caffeoyl-1,5-quinide
4 ′-Hydroxyflavanone
4',7-Dihydroxyflavone
6β-Naltrexol
6β-Naltrexol-d4
18-MC
α-Gliadin
β-Chlornaltrexamine
β-Funaltrexamine
Akuammine
Alvimopan
AM-251
Apigenin
AT-076
Axelopran
Bevenopran
Catechin
Catechin gallate
Clocinnamox
CTAP
CTOP
Cyclofoxy
Cyprodime
Diacetylnalorphine
Diprenorphine
ECG
EGC
Epicatechin
Eptazocine
Gemazocine
Ginsenoside R
Hyperoside
Ibogaine
JDTic
Levallorphan
Lobeline
LY-255582
LY-2196044
Methocinnamox
Methylnaltrexone
Methylsamidorphan chloride
Naldemedine
Nalmefene
Nalodeine (N-allylnorcodeine)
Nalorphine
Nalorphine dinicotinate
Naloxazone
Naloxegol
Naloxol
Naloxonazine
Naloxone
Naltrexazone
Naltrexonazine
Naltrexone
Naltrindole
Naringenin
Noribogaine
Oxilorphan
Pawhuskin A
Rimonabant
Quadazocine
Samidorphan
Taxifolin
ADL-5747 (PF-04856881)
ADL-5859
Alazocine (SKF-10047)
Amoxapine
AR-M100390 (ARM390)
AZD2327
β-Endorphin
BAM-18P
Biphalin
BU-48
Butorphan
Butorphanol
BW373U86
Casokefamide
Cebranopadol
Codeine
Cyclazocine
DADLE
Deltorphin A
Deltorphin I
Deltorphin II
Desmethylclozapine
Desmetramadol (desmethyltramadol)
Dezocine
Diamorphine (heroin)
Dihydroetorphine
Dihydromorphine
DPDPE
DPI-221
DPI-3290
DSLET
Ethylketazocine
Etorphine
Fentanyl
FIT
Fluorophen
Hemorphin-4
Hydrocodone
Hydromorphone
Ibogaine
Isomethadone
JNJ-20788560
KNT-127
Kratom
Laudanosine
Leu-enkephalin
Levomethorphan
Levorphanol
Lexanopadol
Lofentanil
Met-enkephalin (metenkefalin)
Metazocine
Metkefamide
Mitragynine
Mitragynine pseudoindoxyl
Morphine
N-Phenethyl-14-ethoxymetopon
Norbuprenorphine
NalBzOH
Oripavine
Oxycodone
Oxymorphone
Pethidine (meperidine)
Proglumide
Racemethorphan
Racemorphan
RWJ-394674
Samidorphan
SB-235863
SNC-80
SNC-162
TAN-67 (SB-205,607)
TH-030418
Thebaine
Thiobromadol (C-8813)
Tonazocine
Tramadol
TRV250
Xorphanol
Zenazocine
5'-NTII
6β-Naltrexol
6β-Naltrexol-d4
α-Santolol
β-Chlornaltrexamine
Apigenin
AT-076
Axelopran
Bevenopran
BNTX
Catechin
Catechin gallate
Clocinnamox
Diacetylnalorphine
Diprenorphine
ECG
EGC
Eluxadoline
Epicatechin
ICI-154129
ICI-174864
LY-255582
LY-2196044
Methylnaltrexone
Methylnaltrindole
N-Benzylnaltrindole
Nalmefene
Nalorphine
Naltrexone
Naltriben
Naltrindole
Naloxone
Naringenin
Noribogaine
Pawhuskin A
Quadazocine
SDM25N
SoRI-9409
Taxifolin
Thienorphine
18-MC
14-Methoxymetopon
β-Chlornaltrexamine
β-Funaltrexamine
Adrenorphin (metorphamide)
Akuammicine
Alazocine (SKF-10047)
Allomatrine
Apadoline
Asimadoline
BAM-12P
BAM-18P
BAM-22P
Big dynorphin
Bremazocine
BRL-52537
Butorphan
Butorphanol
BW373U86
Cebranopadol
Ciprefadol
CR665
Cyclazocine
Cyclorphan
Cyprenorphine
Desmetramadol (desmethyltramadol)
Diamorphine (heroin)
Diacetylnalorphine
Difelikefalin
Dihydroetorphine
Dihydromorphine
Dinalbuphine sebacate
Diprenorphine
Dynorphin A
Dynorphin B (rimorphin)
Eluxadoline
Enadoline
Eptazocine
Erinacine E
Ethylketazocine
Etorphine
Fedotozine
Fentanyl
Gemazocine
GR-89696
GR-103545
Hemorphin-4
Herkinorin
HS665
Hydromorphone
HZ-2
Ibogaine
ICI-199,441
ICI-204,448
Ketamine
Ketazocine
Laudanosine
Leumorphin (dynorphin B-29)
Levallorphan
Levomethorphan
Levorphanol
Lexanopadol
Lofentanil
LPK-26
Lufuradom
Matrine
MB-1C-OH
Menthol
Metazocine
Metkefamide
Mianserin
Mirtazapine
Morphine
Moxazocine
MR-2034
N-MPPP
Nalbuphine
NalBzOH
Nalfurafine
Nalmefene
Nalodeine (N-allylnorcodeine)
Nalorphine
Naltriben
Niravoline
Norbuprenorphine
Norbuprenorphine-3-glucuronide
Noribogaine
Norketamine
Oripavine
Oxilorphan
Oxycodone
Pentazocine
Pethidine (meperidine)
Phenazocine
Proxorphan
Racemethorphan
Racemorphan
RB-64
Salvinorin A (salvia )
Salvinorin B ethoxymethyl ether
Salvinorin B methoxymethyl ether
Samidorphan
Spiradoline (U-62,066)
TH-030418
Thienorphine
Tifluadom
Tricyclic antidepressants (e.g., amitriptyline , desipramine , imipramine , nortriptyline )
U-50488
U-54,494A
U-69,593
Xorphanol
4',7-Dihydroxyflavone
5'-GNTI
6'-GNTI
6β-Naltrexol
6β-Naltrexol-d4
β-Chlornaltrexamine
Buprenorphine/samidorphan
Amentoflavone
ANTI
Apigenin
Arodyne
AT-076
Aticaprant
Axelopran
AZ-MTAB
Binaltorphimine
BU09059
Buprenorphine
Catechin
Catechin gallate
CERC-501 (LY-2456302)
Clocinnamox
CVL-354
Cyclofoxy
Dezocine
DIPPA
EGC
ECG
Epicatechin
Hyperoside
JDTic
LY-255582
LY-2196044
LY-2444296
LY-2459989
LY-2795050
MeJDTic
Methylnaltrexone
ML190
ML350
MR-2266
N-Fluoropropyl-JDTic
Naloxone
Naltrexone
Naltrindole
Naringenin
Navacaprant
Norbinaltorphimine
Noribogaine
Pawhuskin A
PF-4455242
RB-64
Quadazocine
Taxifolin
UPHIT
Zyklophin
Ac-RYYRWK-NH2
Ac-RYYRIK-NH2
BU08070
Buprenorphine
Cebranopadol
Dihydroetorphine
Etorphine
JNJ-19385899
Levomethorphan
Levorphanol
Lexanopadol
MCOPPB
MT-7716
NNC 63-0532
Nociceptin (orphanin FQ)
Nociceptin (1-11)
Nociceptin (1-13)NH2
Norbuprenorphine
Racemethorphan
Racemorphan
Ro64-6198
Ro65-6570
SCH-221510
SCH-486757
SR-8993
SR-16435
Sunobinop (S-117957)
TH-030418
AT-076
BAN-ORL-24
BTRX-246040 (LY-2940094)
J-113,397
JTC-801
NalBzOH
Nociceptin (1-7)
Nocistatin
SB-612,111
SR-16430
Thienorphine
Trap-101
UFP-101
BL-2401
Candoxatril
D -Phenylalanine
Dexecadotril (retorphan)
Ecadotril (sinorphan)
Kelatorphan
Racecadotril (acetorphan)
RB-101
RB-120
RB-3007
Opiorphan
Selank
Semax
Spinorphin
Thiorphan
Tynorphin
Ubenimex (bestatin)
Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
PR Tooltip Progesterone receptor
9α-Bromo-11-ketoprogesterone
11-Dehydroprogesterone
11-Deoxycorticosterone
16α-Hydroxyprogesterone
17α-Methyl-11-deoxycorticosterone acetate
20α-Dihydroprogesterone
20β-Dihydroprogesterone
Dimepregnen
Diosgenin
P1-185
Progesterone
Progesterone 3-acetyl enol ether
Quingestrone
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (SPRMs Tooltip Selective progesterone receptor modulators )
5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone
Asoprisnil
Asoprisnil ecamate
Guggulsterone
J1042
LG-120838
Metapristone (RU-42633)
Mifepristone (RU-486)
ORF-9371
ORF-9326
ORG-31710
ORG-33628
RMI-12936
Telapristone
Ulipristal acetate
Vilaprisan
ZK-137316
Lilopristone
Lonaprisan
Onapristone
ORG-31710
ORG-31806
ORG-33628
RTI 3021–022
Toripristone
Zanoterone
mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )
11-Deoxycortisol (17α,21-dihydroxyprogesterone)
17α-Hydroxyprogesterone
Allopregnanolone
Mifepristone
Pregnenolone
Progesterone
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Naringenin&oldid=1223139972 "
C a t e g o r i e s :
● A r o m a t a s e i n h i b i t o r s
● D e l t a - o p i o i d r e c e p t o r a n t a g o n i s t s
● F l a v a n o n e s
● R e s o r c i n o l s
● K a p p a - o p i o i d r e c e p t o r a n t a g o n i s t s
● M u - o p i o i d r e c e p t o r a n t a g o n i s t s
● P r o g e s t o g e n s
● P h y t o e s t r o g e n s
● H i s t i d i n e d e c a r b o x y l a s e i n h i b i t o r s
● 3 - H y d r o x y p r o p e n a l s
H i d d e n c a t e g o r i e s :
● A r t i c l e s w i t h o u t I n C h I s o u r c e
● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d C h e m S p i d e r i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d D r u g B a n k i d e n t i f i e r
● E C H A I n f o C a r d I D f r o m W i k i d a t a
● A r t i c l e s w i t h c h a n g e d K E G G i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d F D A i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d I n C h I i d e n t i f i e r
● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s
● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m J a n u a r y 2 0 2 4
● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s
● C h e m b o x i m a g e s i z e s e t
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 1 0 M a y 2 0 2 4 , a t 0 4 : 3 6 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
● P r i v a c y p o l i c y
● A b o u t W i k i p e d i a
● D i s c l a i m e r s
● C o n t a c t W i k i p e d i a
● C o d e o f C o n d u c t
● D e v e l o p e r s
● S t a t i s t i c s
● C o o k i e s t a t e m e n t
● M o b i l e v i e w