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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O6
Molecular Weight 286.2369
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUTEOLIN

SMILES

c1cc(c(cc1-c2cc(=O)c3c(cc(cc3o2)O)O)O)O

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 286.2369
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
[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
Antioxidative components from the aerial parts of Lactuca scariola L.
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
Flavonoids suppress the cytotoxicity of linoleic acid hydroperoxide toward PC12 cells.
2002 Aug
Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit.
2002 Aug
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
Flavonoid concentrations in three grass species and a sedge grown in the field and under controlled environment conditions in response to enhanced UV-B radiation.
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
Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats.
2002 Jan
Polyphenol increases in safflower and cucumber seedlings exposed to strong visible light with limited water.
2002 Jan
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
Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease.
2002 Jan 15
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
Involvement of the Sinorhizobium meliloti leuA gene in activation of nodulation genes by NodD1 and luteolin.
2002 Jul
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.
2002 Jul 17
[Luteolin inhibits proliferation and collagen synthesis of hepatic stellate cells].
2002 Jun
Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment.
2002 Jun
Phagnalon rupestre as a source of compounds active on contact hypersensitivity.
2002 Jun
Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves.
2002 Jun
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
The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent.
2002 Mar
Thiol antioxidants inhibit the adjuvant effects of aerosolized diesel exhaust particles in a murine model for ovalbumin sensitization.
2002 Mar 1
Antinociceptive and anti-inflammatory effects of Crocus sativus L. stigma and petal extracts in mice.
2002 Mar 15
Luteolin reduces lipopolysaccharide-induced lethal toxicity and expression of proinflammatory molecules in mice.
2002 Mar 15
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
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
2002 May
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
2002 May
Blockade of the epidermal growth factor receptor tyrosine kinase activity by quercetin and luteolin leads to growth inhibition and apoptosis of pancreatic tumor cells.
2002 May-Jun
Flavonoids from Ficaria verna Huds.
2002 May-Jun
Effects of estrogenic compounds on immunoglobulin production by mouse splenocytes.
2002 Oct
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002 Oct
Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection.
2002 Sep
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 Jun 26 10:57:19 UTC 2021
Edited
by admin
on Sat Jun 26 10:57:19 UTC 2021
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
LUTEOLIN [WHO-DD]
Common Name English
CYANIDENON-1470
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 Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
DSLD 2388 (Number of products:95)
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
Code System Code Type Description
CAS
491-70-3
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
EPA CompTox
491-70-3
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
MERCK INDEX
M6945
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB15584
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
MESH
D047311
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
FDA UNII
KUX1ZNC9J2
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
PUBCHEM
5280445
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
NCI_THESAURUS
C68467
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-741-0
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
WIKIPEDIA
LUTEOLIN
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
EVMPD
SUB183951
Created by admin on Sat Jun 26 10:57:19 UTC 2021 , Edited by admin on Sat Jun 26 10:57:19 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
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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.