Luteolin
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Luteolin
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Names
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IUPAC name
2-(3,4-Dihydroxyphenyl)- 5,7-dihydroxy-4-chromenone
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Other names
Luteolol Digitoflavone Flacitran Luteoline 3′,4′,5,7-Tetrahydroxyflavone
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Identifiers
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CAS Number
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491-70-3 Y
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3D model (JSmol)
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ChEBI
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CHEBI:15864 N
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ChEMBL
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ChEMBL151 N
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ChemSpider
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4444102 N
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ECHA InfoCard
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100.007.038
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IUPHAR/BPS
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UNII
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KUX1ZNC9J2 N
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InChI InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H NKey: IQPNAANSBPBGFQ-UHFFFAOYSA-N N
InChI=1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H Key: IQPNAANSBPBGFQ-UHFFFAOYAY
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SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
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Properties
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Chemical formula
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C15H10O6 |
Molar mass
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7002286239000000000♠286.239 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is Y N ?)
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Infobox references
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Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.[1]
Natural occurrences[edit]
Luteolin is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen.[1] It has also been isolated from the aromatic flowering plant, Salvia tomentosa in the mint family, Lamiaceae.[2]
Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano.[3][4] It can also be found in the seeds of the palm Aiphanes aculeata.[5]
References[edit]
^ ab Mann, John (1992). Secondary Metabolism (2nd ed.). Oxford, UK: Oxford University Press. pp. 279–280. ISBN 978-0-19-855529-2..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
^ A. Ulubelen; M. Miski; P. Neuman; T. J. Mabry (1979). "Flavonoids of Salvia tomentosa (Labiatae)". Journal of Natural Products. 42 (4): 261–3. doi:10.1021/np50003a002.
^ Kayoko Shimoi; Hisae Okada; Michiyo Furugori; Toshinao Goda; Sachiko Takase; Masayuki Suzuki; Yukihiko Hara; Hiroyo Yamamoto; Naohide Kinae (1998). "Intestinal absorption of luteolin and luteolin 7-O-[beta]-glucoside in rats and humans". FEBS Letters. 438 (3): 220–4. doi:10.1016/S0014-5793(98)01304-0. PMID 9827549.
^ López-Lázaro M. (2009). "Distribution and biological activities of the flavonoid luteolin". Mini Rev Med Chem. 9 (1): 31–59. doi:10.2174/138955709787001712. PMID 19149659.
^ Lee, D; Cuendet, M; Vigo, JS; Graham, JG; Cabieses, F; Fong, HH; Pezzuto, JM; Kinghorn, AD (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic Letters. 3 (14): 2169–71. doi:10.1021/ol015985j. PMID 11440571.
External links[edit]
Media related to Luteolin at Wikimedia Commons
Flavones and their conjugates
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| Aglycones |
| Monohydroxyflavone |
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| Dihydroxyflavones |
- Chrysin
- 4',7-Dihydroxyflavone
- 7,8-Dihydroxyflavone
|
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| Trihydroxyflavones |
- Apigenin
- Baicalein
- Norwogonin
|
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| Tetrahydroxyflavones |
- Isoscutellarein
- Luteolin
- Norartocarpetin
- Scutellarein
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| Pentahydroxyflavones |
- Nortangeretin
- 6-Hydroxyluteolin
- Norwightin
- Hypolaetin
- Tricetin
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| O-methylated flavones |
- Acacetin
- Alnetin
- Artocarpetin
- Chrysoeriol
- Cirsilineol
- Cirsiliol
- Cirsimaritin
- Diosmetin
- Eupatilin
- Genkwanin
- Hispidulin
- Nepetin
- Nobiletin
- Oroxylin A
- Pratol
- Salvigenin
- Sinensetin
- Tangeretin
- Techtochrysin
- Tricin
- Wogonin
- Zapotin
|
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| Glycosides |
| of apigenin |
- Apiin
- Apigetrin
- Isovitexin
- Rhoifolin
- Saponarin
- Schaftoside
- Vicenin-2
- Vitexin
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| of baicalein |
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| of hypolaetin |
- Hypolaetin 8-glucoside
- Hypolaetin 8-glucuronide
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| of luteolin |
- Cynaroside
- Isoorientin
- Orientin
- Veronicastroside
- Luteolin-7-O-glucuronide
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Giraldiin A and B
- Nepitrin
- Oroxindin
- Scutellarin
|
|---|
| Acetylated |
Artocarpetin A Artoindonesianin P
|
|---|
| Sulfated glycosides |
Theograndin I and II
|
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| Polymers |
|
|---|
| Drugs |
|
|---|
Dopamine receptor modulators
|
|---|
| D1-like |
| Agonists |
Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959
- Trepipam
- Zelandopam
Ergolines: Cabergoline
- CY-208,243
- Dihydroergocryptine
- LEK-8829
- Lisuride
- Pergolide
- Terguride
Dihydrexidine derivatives: A-77636
- A-86929
- Adrogolide (ABT-431, DAS-431)
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine
Phenethylamines: BCO-001
- Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
- Melevodopa
L-Phenylalanine
L-Tyrosine
- XP21279
Others: A-68930
- Apomorphine
- Isocorypalmine
- Nuciferine
- PF-6649751
- PF 6669571
- Propylnorapomorphine
- Rotigotine
- SKF-89,145
- SKF-89,626
- Stepholidine
- Tetrahydropalmatine
|
|---|
| Antagonists |
Typical antipsychotics: Butaclamol
- Chlorpromazine
- Chlorprothixene
Flupentixol (flupenthixol) (+melitracen)
- Fluphenazine
- Loxapine
Perphenazine (+amitriptyline)
- Pifluthixol
- Thioridazine
- Thiothixene
Trifluoperazine (+tranylcypromine)
- Zuclopenthixol
Atypical antipsychotics: Asenapine
- Clorotepine
- Clotiapine
- Clozapine
- DHA-clozapine
- Fluperlapine
- Iloperidone
- Norclozapine
- Norquetiapine
Olanzapine (++fluoxetine)
- Paliperidone
- Quetiapine
- Risperidone
- Tefludazine
- Zicronapine
- Ziprasidone
- Zotepine
Others: Berupipam
- Ecopipam
- EEDQ
- Metitepine (methiothepin)
- Odapipam
- Perlapine
- SCH-23390
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|---|
|
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| D2-like |
| Agonists |
Adamantanes: Amantadine
- Memantine
- Rimantadine
Aminotetralins: 5-OH-DPAT
- 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232
Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Ergocornine
- Lergotrile
- Lisuride
- LSD
- Pergolide
- Terguride
Dihydrexidine derivatives: 2-OH-NPA
- Ciladopa
- Dihydrexidine
- Dinoxyline
- N,N-Propyldihydrexidine
Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
- Melevodopa
- XP21279
Atypical antipsychotics: Alentemol (U-66444B)
Aripiprazole (+sertraline)
- Aripiprazole lauroxil
- Bifeprunox
- Brexpiprazole
- Cariprazine
- F-15063
- Lumateperone
- Norclozapine
- RP-5063
Others: 3-PPP
- A-412997
- ABT-670
- ABT-724
- Adrafinil
- Aplindore
- Apomorphine
- Arketamine
- Armodafinil
- BP-897
- Captodiame
- CP-226,269
- Dizocilpine
- Esketamine
- Flibanserin
- GSK-789,472
- Ketamine
- Mesulergine
- Modafinil
- OSU-6162
- Pardoprunox
- PD-128,907
- PD-168,077
- PF-219,061
- PF-592,379
- Phencyclidine
- Piribedil
- Pramipexole
- Preclamol
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Roxindole
- Salvinorin A
- SKF-83,959
- Sumanirole
- Talipexole
- Umespirone
- WAY-100,635
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| Antagonists |
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- See also: Receptor/signaling modulators
- Adrenergics
- Serotonergics
- Monoamine reuptake inhibitors
- Monoamine releasing agents
- Monoamine metabolism modulators
- Monoamine neurotoxins
|
GABAA receptor positive modulators
|
|---|
| Alcohols |
- Brometone
- Butanol
- Chloralodol
- Chlorobutanol (cloretone)
Ethanol (alcohol) (alcoholic drink)
- Ethchlorvynol
- Isobutanol
- Isopropanol
- Menthol
- Methanol
- Methylpentynol
- Pentanol
- Petrichloral
- Propanol
tert-Butanol (2M2P)
tert-Pentanol (2M2B)
- Tribromoethanol
- Trichloroethanol
- Triclofos
- Trifluoroethanol
|
|---|
| Barbiturates |
- (-)-DMBB
- Allobarbital
- Alphenal
- Amobarbital
- Aprobarbital
- Barbexaclone
- Barbital
- Benzobarbital
- Benzylbutylbarbiturate
- Brallobarbital
- Brophebarbital
- Butabarbital/Secbutabarbital
- Butalbital
- Buthalital
- Butobarbital
- Butallylonal
- Carbubarb
- Crotylbarbital
- Cyclobarbital
- Cyclopentobarbital
- Difebarbamate
- Enallylpropymal
- Ethallobarbital
- Eterobarb
- Febarbamate
- Heptabarb
- Heptobarbital
- Hexethal
- Hexobarbital
- Metharbital
- Methitural
- Methohexital
- Methylphenobarbital
- Narcobarbital
- Nealbarbital
- Pentobarbital
- Phenallymal
- Phenobarbital
- Phetharbital
- Primidone
- Probarbital
- Propallylonal
- Propylbarbital
- Proxibarbital
- Reposal
- Secobarbital
- Sigmodal
- Spirobarbital
- Talbutal
- Tetrabamate
- Tetrabarbital
- Thialbarbital
- Thiamylal
- Thiobarbital
- Thiobutabarbital
- Thiopental
- Thiotetrabarbital
- Valofane
- Vinbarbital
- Vinylbital
|
|---|
| Benzodiazepines |
|
|---|
| Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
|
|---|
| Flavonoids |
- 6-Methylapigenin
- Ampelopsin (dihydromyricetin)
- Apigenin
- Baicalein
- Baicalin
- Catechin
- EGC
- EGCG
- Hispidulin
- Linarin
- Luteolin
- Rc-OMe
Skullcap constituents (e.g., baicalin)
- Wogonin
|
|---|
| Imidazoles |
- Etomidate
- Metomidate
- Propoxate
|
|---|
Kava constituents |
- 10-Methoxyyangonin
- 11-Methoxyyangonin
- 11-Hydroxyyangonin
- Desmethoxyyangonin
- 11-Methoxy-12-hydroxydehydrokavain
- 7,8-Dihydroyangonin
- Kavain
- 5-Hydroxykavain
- 5,6-Dihydroyangonin
- 7,8-Dihydrokavain
- 5,6,7,8-Tetrahydroyangonin
- 5,6-Dehydromethysticin
- Methysticin
- 7,8-Dihydromethysticin
- Yangonin
|
|---|
| Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Carbromal
- Capuride
- Ectylurea
|
|---|
| Neuroactive steroids |
- Acebrochol
- Allopregnanolone (brexanolone)
- Alfadolone
- Alfaxalone
- 3α-Androstanediol
- Androstenol
- Androsterone
- Certain anabolic-androgenic steroids
- Cholesterol
- DHDOC
- 3α-DHP
- 5α-DHP
- 5β-DHP
- DHT
- Etiocholanolone
- Ganaxolone
- Hydroxydione
- Minaxolone
- ORG-20599
- ORG-21465
- P1-185
- Pregnanolone (eltanolone)
- Progesterone
- Renanolone
- SAGE-105
- SAGE-324
- SAGE-516
- SAGE-689
- SAGE-872
- Testosterone
- THDOC
- Zuranolone
|
|---|
| Nonbenzodiazepines |
β-Carbolines: Abecarnil
- Gedocarnil
- Harmane
- SL-651,498
- ZK-93423
Cyclopyrrolones: Eszopiclone
- Pagoclone
- Pazinaclone
- Suproclone
- Suriclone
- Zopiclone
Imidazopyridines: Alpidem
- DS-1
- Necopidem
- Saripidem
- Zolpidem
Pyrazolopyrimidines: Divaplon
- Fasiplon
- Indiplon
- Lorediplon
- Ocinaplon
- Panadiplon
- Taniplon
- Zaleplon
Others: Adipiplon
- CGS-8216
- CGS-9896
- CGS-13767
- CGS-20625
- CL-218,872
- CP-615,003
- CTP-354
- ELB-139
- GBLD-345
- Imepitoin
- JM-1232
- L-838,417
- Lirequinil (Ro41-3696)
- NS-2664
- NS-2710
- NS-11394
- Pipequaline
- ROD-188
- RWJ-51204
- SB-205,384
- SX-3228
- TGSC01AA
- TP-003
- TPA-023
- TP-13
- U-89843A
- U-90042
- Viqualine
- Y-23684
|
|---|
| Phenols |
- Fospropofol
- Propofol
- Thymol
|
|---|
| Piperidinediones |
- Glutethimide
- Methyprylon
- Piperidione
- Pyrithyldione
|
|---|
| Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
|
|---|
| Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
|
|---|
Volatiles/gases
|
- Acetone
- Acetophenone
- Acetylglycinamide chloral hydrate
- Aliflurane
- Benzene
- Butane
- Butylene
- Centalun
- Chloral
- Chloral betaine
- Chloral hydrate
- Chloroform
- Cryofluorane
- Desflurane
- Dichloralphenazone
- Dichloromethane
- Diethyl ether
- Enflurane
- Ethyl chloride
- Ethylene
- Fluroxene
- Gasoline
- Halopropane
- Halothane
- Isoflurane
- Kerosine
- Methoxyflurane
- Methoxypropane
- Nitric oxide
- Nitrogen
- Nitrous oxide
- Norflurane
- Paraldehyde
- Propane
- Propylene
- Roflurane
- Sevoflurane
- Synthane
- Teflurane
- Toluene
- Trichloroethane (methyl chloroform)
- Trichloroethylene
- Vinyl ether
|
|---|
| Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
Avermectins (e.g., ivermectin)
Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- DEABL
Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
- DS2
- Efavirenz
- Etazepine
- Etifoxine
Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
- Fluoxetine
- Flupirtine
- Hopantenic acid
- Lanthanum
- Lavender oil
Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Niacin
- Nicotinamide (niacinamide)
- Org 25,435
- Phenytoin
- Propanidid
- Retigabine (ezogabine)
- Safranal
- Seproxetine
- Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
Terpenoids (e.g., borneol)
- Topiramate
Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)
Unsorted benzodiazepine site positive modulators: α-Pinene
- MRK-409 (MK-0343)
- TCS-1105
- TCS-1205
|
|---|
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators |

Categories:
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