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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O6
Molecular Weight 286.2363
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUTEOLIN

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C3=CC=C(O)C(O)=C3

InChI

InChIKey=IQPNAANSBPBGFQ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H10O6
Molecular Weight 286.2363
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Luteolin, 3',4',5,7-tetrahydroxyflavone, is a common flavonoid that exists in many types of plants including fruits, vegetables, and medicinal herbs. Plants rich in luteolin have been used in Chinese traditional medicine for treating various diseases such as hypertension, inflammatory disorders, and cancer. Luteolin possesses a variety of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial and anticancer activities. Numerous studies have shown that luteolin possesses beneficial neuroprotective effects both in vitro and in vivo.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Structure activity relationships for the chemical behaviour and toxicity of electrophilic quinones/quinone methides.
2001
A new flavone derivative from Ehretia ovalifolia leaves.
2001 Aug
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.
2001 Dec
Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation.
2001 Dec
Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L.
2001 Jul
Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae).
2001 Mar-Apr
Inhibition of environmental estrogen-induced proliferation of human breast carcinoma MCF-7 cells by flavonoids.
2001 May
Flavonoids and urate antioxidant interplay in plasma oxidative stress.
2001 May
[Constituents of the leaves of Holodiscus discolor (Pursh) Maxim].
2001 Nov
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.
2001 Oct
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.
2001 Oct
Antioxidative components from the aerial parts of Lactuca scariola L.
2001 Oct
Effect of oral treatment of Perilla frutescens and its constituents on type-I allergy in mice.
2001 Oct
Glycosides and xanthine oxidase inhibitors from Conyza bonariensis.
2001 Oct
Purification and characterization of nuclear type II [(3)H]estradiol binding sites from the rat uterus: covalent labeling with [(3)H]luteolin.
2001 Sep
Effect of three flavonoids, 5,7,3',4'-tetrahydroxy-3-methoxy flavone, luteolin, and quercetin, on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophil.
2001 Sep 1
Effects of several flavonoids on the growth of B16F10 and SK-MEL-1 melanoma cell lines: relationship between structure and activity.
2002 Apr
Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii.
2002 Aug
Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds.
2002 Aug 28
Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.).
2002 Feb
Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.
2002 Feb
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.
2002 Feb
Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms.
2002 Feb
Antinociceptive effect of the aqueous extract of Balbisia calycina.
2002 Feb
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002 Feb
Effect of flavonoids on cell cycle progression in prostate cancer cells.
2002 Feb 8
O-Glucosyltransferase activities toward phenolic natural products and xenobiotics in wheat and herbicide-resistant and herbicide-susceptible black-grass (Alopecurus myosuroides).
2002 Jan
Phytochemical and antimicrobial studies of Begonia malabarica.
2002 Jan
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.
2002 Jul
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Antioxidative flavonoids from leaves of Carthamus tinctorius.
2002 Jun
Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment.
2002 Jun
Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves.
2002 Jun
In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.
2002 Jun 4
Luteolin, a flavone, does not suppress postprandial glucose absorption through an inhibition of alpha-glucosidase action.
2002 Mar
Effects of extract from Angelica keiskei and its component, cynaroside, on the hepatic bromobenzene-metabolizing enzyme system in rats.
2002 Mar
Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method.
2002 Mar 27
Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L.
2002 Mar-Apr
Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae).
2002 Mar-Apr
Effects of luteolin on the inhibition of proliferation and induction of apoptosis in human myeloid leukaemia cells.
2002 May
Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases.
2002 May
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
2002 May
Flavonoid compounds in the flowers of Abutilon indicum (L.) Sweet (Malvaceae).
2002 May-Jun
Flavonoids from Ficaria verna Huds.
2002 May-Jun
Effects of estrogenic compounds on immunoglobulin production by mouse splenocytes.
2002 Oct
Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection.
2002 Sep
Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens.
2002 Sep
Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory.
2002 Sep 11
Identification of nuclear type II [(3)H]estradiol binding sites as histone H4.
2002 Sep 6
Patents

Sample Use Guides

An open-label pilot study: assessment the effectiveness and tolerability in white children with autism spectrum disorders of a dietary supplement containing 2 flavonoids (>95% pure), luteolin (100 mg/capsule, from chamomile) and quercetin (70 mg/capsule), and the quercetin glycoside rutin (30 mg/capsule) from the Sophora japonica leaf, formulated in olive kernel oil to increase oral absorption.
Route of Administration: Oral
17.5 uM luteolin inhibits MCF-7 cell proliferation by about 50% at 48 hours following treatment and appears cytostatic but non toxic
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:13:06 UTC 2023
Edited
by admin
on Sat Dec 16 20:13:06 UTC 2023
Record UNII
KUX1ZNC9J2
Record Status Validated (UNII)
Record Version
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Name Type Language
LUTEOLIN
INCI   MI  
INCI  
Official Name English
LUTEOLIN [INCI]
Common Name English
FLACITRAN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-
Systematic Name English
LUTEOLIN [MI]
Common Name English
CYANIDENON-1470
Common Name English
Luteolin [WHO-DD]
Common Name English
YAMA KARIYASU
Common Name English
WELD LAKE
Common Name English
SALIFAZIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68464
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
DSLD 2388 (Number of products:95)
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
Code System Code Type Description
CAS
491-70-3
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
CHEBI
57545
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID4074988
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
MERCK INDEX
m6945
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB15584
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
CHEBI
15864
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
MESH
D047311
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
FDA UNII
KUX1ZNC9J2
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
PUBCHEM
5280445
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
SMS_ID
100000170151
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
NCI_THESAURUS
C68467
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-741-0
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
WIKIPEDIA
LUTEOLIN
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
EVMPD
SUB183951
Created by admin on Sat Dec 16 20:13:07 UTC 2023 , Edited by admin on Sat Dec 16 20:13:07 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
ORAC value expressed as umol TE/g for this compound was 7870 +/- 350. ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH. CAP-e value expressed as GAE/g was 5040 +/- 260.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
37% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
PARENT -> CONSTITUENT ALWAYS PRESENT
Luteolin all significantly inhibited p38 and JNK phosphorylation at 5 and 10 uM. The SEAP reporter assay was conducted to evaluate the inhibitory effects of luteolin in inhibiting NF-.KAPPA.B activation in our previous report. The IC50 value of this compound was estimated at 12.4 uM for luteolin.