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 |
|||
Target ID: CHEMBL2095165 |
|||
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 |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation. | 2001 Dec |
|
| Inhibition of environmental estrogen-induced proliferation of human breast carcinoma MCF-7 cells by flavonoids. | 2001 May |
|
| [Constituents of the leaves of Holodiscus discolor (Pursh) Maxim]. | 2001 Nov |
|
| Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. | 2001 Oct |
|
| Antioxidative components from the aerial parts of Lactuca scariola L. | 2001 Oct |
|
| 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 |
|
| 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 |
|
| Antimicrobial activity of perilla seed polyphenols against oral pathogenic bacteria. | 2002 Apr |
|
| Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii. | 2002 Aug |
|
| Flavonoids suppress the cytotoxicity of linoleic acid hydroperoxide toward PC12 cells. | 2002 Aug |
|
| Inhibition of LPS-stimulated pathways in macrophages by the flavonoid luteolin. | 2002 Aug |
|
| Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. | 2002 Aug |
|
| Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds. | 2002 Aug 28 |
|
| Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L. | 2002 Feb |
|
| 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 Feb |
|
| 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 |
|
| 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 flavonoids on cell cycle progression in prostate cancer cells. | 2002 Feb 8 |
|
| Polyphenol increases in safflower and cucumber seedlings exposed to strong visible light with limited water. | 2002 Jan |
|
| Phytochemical and antimicrobial studies of Begonia malabarica. | 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 |
|
| Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. | 2002 Jul |
|
| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
|
| Involvement of the Sinorhizobium meliloti leuA gene in activation of nodulation genes by NodD1 and luteolin. | 2002 Jul |
|
| Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide. | 2002 Jul 17 |
|
| Antioxidative flavonoids from leaves of Carthamus tinctorius. | 2002 Jun |
|
| [Luteolin inhibits proliferation and collagen synthesis of hepatic stellate cells]. | 2002 Jun |
|
| Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment. | 2002 Jun |
|
| Phagnalon rupestre as a source of compounds active on contact hypersensitivity. | 2002 Jun |
|
| Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. | 2002 Jun |
|
| Biophenols in table olives. | 2002 Jun 19 |
|
| In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. | 2002 Jun 4 |
|
| Effects of extract from Angelica keiskei and its component, cynaroside, on the hepatic bromobenzene-metabolizing enzyme system in rats. | 2002 Mar |
|
| Thiol antioxidants inhibit the adjuvant effects of aerosolized diesel exhaust particles in a murine model for ovalbumin sensitization. | 2002 Mar 1 |
|
| Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L. | 2002 Mar-Apr |
|
| Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). | 2002 Mar-Apr |
|
| Effects of luteolin on the inhibition of proliferation and induction of apoptosis in human myeloid leukaemia cells. | 2002 May |
|
| 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 |
|
| Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells. | 2002 Oct |
|
| Analysis of flavonoids in Ginkgo biloba L. and its phytopharmaceuticals by capillary electrophoresis with electrochemical detection. | 2002 Sep |
|
| Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. | 2002 Sep |
|
| Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory. | 2002 Sep 11 |
|
| 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
by
admin
on
Edited
Sat Dec 16 20:13:06 GMT 2023
by
admin
on
Sat Dec 16 20:13:06 GMT 2023
|
| Record UNII |
KUX1ZNC9J2
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C68464
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
||
|
DSLD |
2388 (Number of products:95)
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
491-70-3
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
57545
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
DTXSID4074988
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
m6945
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | Merck Index | ||
|
DB15584
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
15864
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
D047311
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
KUX1ZNC9J2
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
5280445
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
100000170151
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
C68467
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
207-741-0
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
LUTEOLIN
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY | |||
|
SUB183951
Created by
admin on Sat Dec 16 20:13:07 GMT 2023 , Edited by admin on Sat Dec 16 20:13:07 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
SOLVATE->ANHYDROUS | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
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.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
37% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
|
||
|
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.
|
