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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O6.H2O
Molecular Weight 304.2516
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUTEOLIN MONOHYDRATE

SMILES

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

InChI

InChIKey=JGMZBVVOXURYRU-UHFFFAOYSA-N
InChI=1S/C15H10O6.H2O/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;1H2

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

Molecular Formula H2O
Molecular Weight 18.0153
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
Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells.
2000 Apr
Study of antioxidant effect of apigenin, luteolin and quercetin by DNA protective method.
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
Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality.
2001 Jan
In vitro absorption and metabolism of nobiletin, a chemopreventive polymethoxyflavonoid in citrus fruits.
2001 Jan
A distinctive flavonoid chemistry for the anomalous genus Biebersteinia.
2001 Jan
Aquiledine and isoaquiledine, novel flavonoid alkaloids from Aquilegia ecalcarata.
2001 Jan
Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages.
2001 Jan
Antioxidant principles from Bauhinia tarapotensis.
2001 Jul
Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments.
2001 Jul
Antioxidant effect of flavonoids after ascorbate/Fe(2+)-induced oxidative stress in cultured retinal cells.
2001 Jul 1
Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones.
2001 Jun
Inhibitory actions of luteolin on the growth and arylamine N-acetyltransferase activity in strains of Helicobacter pylori from ulcer patients.
2001 Jun
Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex.
2001 Mar
Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae).
2001 Mar-Apr
Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1.
2001 May 15
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
Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii.
2002 Aug
Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.
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
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002 Feb
O-Glucosyltransferase activities toward phenolic natural products and xenobiotics in wheat and herbicide-resistant and herbicide-susceptible black-grass (Alopecurus myosuroides).
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
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment.
2002 Jun
In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.
2002 Jun 4
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
Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases.
2002 May
Flavonoid compounds in the flowers of Abutilon indicum (L.) Sweet (Malvaceae).
2002 May-Jun
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
Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I.
2002 Sep 1
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 15:26:48 GMT 2023
Edited
by admin
on Sat Dec 16 15:26:48 GMT 2023
Record UNII
N79TPJ3DTD
Record Status Validated (UNII)
Record Version
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Name Type Language
LUTEOLIN MONOHYDRATE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-, HYDRATE (1:1)
Systematic Name English
LUTEOLIN MONOHYDRATE [MI]
Common Name English
FLAVONE, 3',4',5,7-TETRAHYDROXY-, MONOHYDRATE
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-, MONOHYDRATE
Systematic Name English
Code System Code Type Description
MERCK INDEX
m6945
Created by admin on Sat Dec 16 15:26:48 GMT 2023 , Edited by admin on Sat Dec 16 15:26:48 GMT 2023
PRIMARY
PUBCHEM
67110957
Created by admin on Sat Dec 16 15:26:48 GMT 2023 , Edited by admin on Sat Dec 16 15:26:48 GMT 2023
PRIMARY
FDA UNII
N79TPJ3DTD
Created by admin on Sat Dec 16 15:26:48 GMT 2023 , Edited by admin on Sat Dec 16 15:26:48 GMT 2023
PRIMARY
CAS
6113-16-2
Created by admin on Sat Dec 16 15:26:48 GMT 2023 , Edited by admin on Sat Dec 16 15:26:48 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE