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=CC2=C(C(=O)C=C(O2)C3=CC=C(O)C(O)=C3)C(O)=C1
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 |
|---|---|---|
| Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L. | 2002-10-09 |
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| Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). | 2002-10-09 |
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| Effects of estrogenic compounds on immunoglobulin production by mouse splenocytes. | 2002-10 |
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| Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells. | 2002-10 |
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| Flavonoid compounds in the flowers of Abutilon indicum (L.) Sweet (Malvaceae). | 2002-09-17 |
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| Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory. | 2002-09-11 |
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| Identification of nuclear type II [(3)H]estradiol binding sites as histone H4. | 2002-09-06 |
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| Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. | 2002-09-01 |
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| Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection. | 2002-09 |
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| Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. | 2002-09 |
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| Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds. | 2002-08-28 |
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| Blockade of the epidermal growth factor receptor tyrosine kinase activity by quercetin and luteolin leads to growth inhibition and apoptosis of pancreatic tumor cells. | 2002-08-10 |
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| Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii. | 2002-08 |
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| Flavonoids suppress the cytotoxicity of linoleic acid hydroperoxide toward PC12 cells. | 2002-08 |
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| Inhibition of LPS-stimulated pathways in macrophages by the flavonoid luteolin. | 2002-08 |
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| Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. | 2002-08 |
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| Flavonoids from Ficaria verna Huds. | 2002-07-23 |
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| Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide. | 2002-07-17 |
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| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | 2002-07 |
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| Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. | 2002-07 |
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| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002-07 |
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| Involvement of the Sinorhizobium meliloti leuA gene in activation of nodulation genes by NodD1 and luteolin. | 2002-07 |
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| Biophenols in table olives. | 2002-06-19 |
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| In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. | 2002-06-04 |
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| Antioxidative flavonoids from leaves of Carthamus tinctorius. | 2002-06 |
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| [Luteolin inhibits proliferation and collagen synthesis of hepatic stellate cells]. | 2002-06 |
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| Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment. | 2002-06 |
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| Phagnalon rupestre as a source of compounds active on contact hypersensitivity. | 2002-06 |
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| Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. | 2002-06 |
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| LC determination of flavonoids: separation of quercetin, luteolin and 3-O-methylquercetin in Achyrocline satureioides preparations. | 2002-05-15 |
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| Effects of luteolin on the inhibition of proliferation and induction of apoptosis in human myeloid leukaemia cells. | 2002-05 |
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| Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. | 2002-05 |
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| In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. | 2002-05 |
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| Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements. | 2002-05 |
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| Antimicrobial activity of perilla seed polyphenols against oral pathogenic bacteria. | 2002-04 |
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| Effects of several flavonoids on the growth of B16F10 and SK-MEL-1 melanoma cell lines: relationship between structure and activity. | 2002-04 |
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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. | 2002-03-27 |
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| Antinociceptive and anti-inflammatory effects of Crocus sativus L. stigma and petal extracts in mice. | 2002-03-15 |
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| Luteolin reduces lipopolysaccharide-induced lethal toxicity and expression of proinflammatory molecules in mice. | 2002-03-15 |
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| Thiol antioxidants inhibit the adjuvant effects of aerosolized diesel exhaust particles in a murine model for ovalbumin sensitization. | 2002-03-01 |
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| Luteolin, a flavone, does not suppress postprandial glucose absorption through an inhibition of alpha-glucosidase action. | 2002-03 |
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| Effects of extract from Angelica keiskei and its component, cynaroside, on the hepatic bromobenzene-metabolizing enzyme system in rats. | 2002-03 |
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| The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. | 2002-03 |
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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.). | 2002-02 |
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| Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L. | 2002-02 |
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| 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. | 2002-02 |
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| Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats. | 2002-01 |
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| Polyphenol increases in safflower and cucumber seedlings exposed to strong visible light with limited water. | 2002-01 |
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| Dietary flavonoids: bioavailability, metabolic effects, and safety. | 2002 |
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| In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves. | 2001-10 |
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
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KUX1ZNC9J2
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Validated (UNII)
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C68464
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2388 (Number of products:95)
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m6945
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DB15584
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15864
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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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