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 |
|---|---|---|
| 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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| Inhibitory effect of decoction of Perilla frutescens on cultured murine mesangial cell proliferation and quantitative analysis of its active constituents. | 2001 Feb |
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| Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts. | 2001 Feb |
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| Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation. | 2001 Feb 15 |
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| Antioxidant effect of flavonoids after ascorbate/Fe(2+)-induced oxidative stress in cultured retinal cells. | 2001 Jul 1 |
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| Inhibitory actions of luteolin on the growth and arylamine N-acetyltransferase activity in strains of Helicobacter pylori from ulcer patients. | 2001 Jun |
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| Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1. | 2001 May 15 |
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| [Constituents of the leaves of Holodiscus discolor (Pursh) Maxim]. | 2001 Nov |
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| In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves. | 2001 Oct |
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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 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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| Effects of several flavonoids on the growth of B16F10 and SK-MEL-1 melanoma cell lines: relationship between structure and activity. | 2002 Apr |
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| Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii. | 2002 Aug |
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| Flavonoids suppress the cytotoxicity of linoleic acid hydroperoxide toward PC12 cells. | 2002 Aug |
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| Inhibition of LPS-stimulated pathways in macrophages by the flavonoid luteolin. | 2002 Aug |
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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 flavonoids on cell cycle progression in prostate cancer cells. | 2002 Feb 8 |
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| O-Glucosyltransferase activities toward phenolic natural products and xenobiotics in wheat and herbicide-resistant and herbicide-susceptible black-grass (Alopecurus myosuroides). | 2002 Jan |
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| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | 2002 Jul |
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| Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. | 2002 Jul |
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| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
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| Involvement of the Sinorhizobium meliloti leuA gene in activation of nodulation genes by NodD1 and luteolin. | 2002 Jul |
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| Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide. | 2002 Jul 17 |
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| Antioxidative flavonoids from leaves of Carthamus tinctorius. | 2002 Jun |
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| [Luteolin inhibits proliferation and collagen synthesis of hepatic stellate cells]. | 2002 Jun |
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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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| Phagnalon rupestre as a source of compounds active on contact hypersensitivity. | 2002 Jun |
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| Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. | 2002 Jun |
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| Luteolin, a flavone, does not suppress postprandial glucose absorption through an inhibition of alpha-glucosidase action. | 2002 Mar |
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| The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. | 2002 Mar |
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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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| Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). | 2002 Mar-Apr |
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| Effects of luteolin on the inhibition of proliferation and induction of apoptosis in human myeloid leukaemia cells. | 2002 May |
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| Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements. | 2002 May |
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| Flavonoid compounds in the flowers of Abutilon indicum (L.) Sweet (Malvaceae). | 2002 May-Jun |
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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 May-Jun |
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| Flavonoids from Ficaria verna Huds. | 2002 May-Jun |
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| Effects of estrogenic compounds on immunoglobulin production by mouse splenocytes. | 2002 Oct |
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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 Oct |
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| Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection. | 2002 Sep |
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| Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. | 2002 Sep |
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| Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory. | 2002 Sep 11 |
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| 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
| Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 20:13:06 GMT 2023
by
admin
on
Sat Dec 16 20:13:06 GMT 2023
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| Record UNII |
KUX1ZNC9J2
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| Record Status |
Validated (UNII)
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| Record Version |
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C68464
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DSLD |
2388 (Number of products:95)
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491-70-3
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57545
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DTXSID4074988
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m6945
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DB15584
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15864
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D047311
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KUX1ZNC9J2
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5280445
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100000170151
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C68467
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207-741-0
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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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