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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| Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
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| Induction of heme oxygenase-1 expression in macrophages by diesel exhaust particle chemicals and quinones via the antioxidant-responsive element. | 2000 Sep 15 |
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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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| Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex. | 2001 Mar |
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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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| Dietary flavonoids: bioavailability, metabolic effects, and safety. | 2002 |
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| Antiallergic effect of flavonoid glycosides obtained from Mentha piperita 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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| 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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| Phytochemical and antimicrobial studies of Begonia malabarica. | 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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| 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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| Phagnalon rupestre as a source of compounds active on contact hypersensitivity. | 2002 Jun |
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| Biophenols in table olives. | 2002 Jun 19 |
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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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| Flavonoid compounds in the flowers of Abutilon indicum (L.) Sweet (Malvaceae). | 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, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. | 2002 Sep 1 |
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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Edited
Thu Jul 06 01:53:22 UTC 2023
by
admin
on
Thu Jul 06 01:53:22 UTC 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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NCI_THESAURUS |
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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