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
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
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
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Target ID: CHEMBL2095165 |
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Target ID: CHEMBL2185 |
0.357 µM [IC50] | ||
Target ID: CHEMBL262 |
1.5 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. | 2000 Jun 20 |
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| Structure activity relationships for the chemical behaviour and toxicity of electrophilic quinones/quinone methides. | 2001 |
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| Study of antioxidant effect of apigenin, luteolin and quercetin by DNA protective method. | 2001 |
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| A new flavone derivative from Ehretia ovalifolia leaves. | 2001 Aug |
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| Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens. | 2001 Dec |
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| Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation. | 2001 Dec |
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| Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L. | 2001 Jul |
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| Antioxidant principles from Bauhinia tarapotensis. | 2001 Jul |
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| 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 |
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| Luteolin-inhibited arylamine N-acetyltransferase activity and DNA-2-aminofluorene adduct in human and mouse leukemia cells. | 2001 Jul |
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| Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. | 2001 Jun |
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| Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex. | 2001 Mar |
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| Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae). | 2001 Mar-Apr |
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| Inhibition of environmental estrogen-induced proliferation of human breast carcinoma MCF-7 cells by flavonoids. | 2001 May |
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| Flavonoids and urate antioxidant interplay in plasma oxidative stress. | 2001 May |
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| Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. | 2001 Oct |
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| Antioxidative components from the aerial parts of Lactuca scariola L. | 2001 Oct |
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| Effect of oral treatment of Perilla frutescens and its constituents on type-I allergy in mice. | 2001 Oct |
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| Glycosides and xanthine oxidase inhibitors from Conyza bonariensis. | 2001 Oct |
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| 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 |
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| Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. | 2002 Aug |
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| Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds. | 2002 Aug 28 |
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| Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.). | 2002 Feb |
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| 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 |
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| Antinociceptive effect of the aqueous extract of Balbisia calycina. | 2002 Feb |
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| Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils. | 2002 Feb |
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| Effect of flavonoids on cell cycle progression in prostate cancer cells. | 2002 Feb 8 |
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| Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats. | 2002 Jan |
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| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
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| Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment. | 2002 Jun |
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| In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. | 2002 Jun 4 |
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| The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. | 2002 Mar |
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| Antinociceptive and anti-inflammatory effects of Crocus sativus L. stigma and petal extracts in mice. | 2002 Mar 15 |
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| Luteolin reduces lipopolysaccharide-induced lethal toxicity and expression of proinflammatory molecules in mice. | 2002 Mar 15 |
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| 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 |
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| Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L. | 2002 Mar-Apr |
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| Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. | 2002 May |
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| LC determination of flavonoids: separation of quercetin, luteolin and 3-O-methylquercetin in Achyrocline satureioides preparations. | 2002 May 15 |
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| Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. | 2002 Sep 1 |
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| Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory. | 2002 Sep 11 |
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
| Substance Class |
Chemical
Created
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admin
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| Record UNII |
KUX1ZNC9J2
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| Record Status |
Validated (UNII)
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C68464
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2388 (Number of products:95)
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491-70-3
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57545
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m6945
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DB15584
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15864
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100000170151
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C68467
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LUTEOLIN
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SUB183951
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| Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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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.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
37% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
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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.
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