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L9283

Sigma-Aldrich

Luteolin

≥98% (TLC), powder, antioxidant

Synonyme(s) :

3′,4′,5,7-Tetrahydroxyflavone

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About This Item

Formule empirique (notation de Hill):
C15H10O6
Numéro CAS:
Poids moléculaire :
286.24
Numéro Beilstein :
292084
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Luteolin, ≥98% (TLC), powder

Niveau de qualité

Pureté

≥98% (TLC)

Forme

powder

Durée de conservation

3 yr

Couleur

yellow

Pf

~330 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

Oc1cc(O)c2C(=O)C=C(Oc2c1)c3ccc(O)c(O)c3

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

Clé InChI

IQPNAANSBPBGFQ-UHFFFAOYSA-N

Informations sur le gène

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Description générale

Luteolin (3′,4′,5′,7′-tetrahydroxyflavone), a polyphenolic compound belongs to flavones subclass of flavonoids. Luteolin is commonly found in plants like celery, green peppers and chamomile tea. Luteolin is one of the major flavonoids present in the flower extract of Hieracium pannosum Boiss, aerial part of Dracocephalum kotschyi, and contributes to the antioxidant potential of the plant. Luteolin possesses antioxidant, anti-inflammatory properties, and exerts anti-tumor potential primarily through apoptosis. Luteolin exerts its apoptotic activity through downregulation of protein kinase B (Akt) pathway leading to caspase mediated apoptosis. Luteolin also resensitizes cancer cells to therapeutics. Luteolin regulates the inflammatory genes and reduces nitric oxide and inflammatory cytokine production. The anti-inflammatory property of luteolin implicates it as a potential therapeutic agent for the neurodegenerative disease like Alzheimer′s disease. In plants, luteolin induces nodulation protein F (nodF) gene.

Application

Luteolin has been used:
  • to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cells
  • as an additive in M9 minimal medium to induce nodF gene expression
  • as a reference standard to qualitatively and quantitatively analyse luteolin using reverse phase-high performance liquid chromatography with diode array detector (RP-HPLC-DAD)
  • as a reaction supplement for β-galactosidase assay
  • to elucidate the anti-inflammatory efficacy of luteolin in pseudorabies virus infected RAW264.7 cell line by measuring the anti-inflammatory mediators production and also cell viability and cytotoxicity assay

Actions biochimiques/physiologiques

Hydroxylated flavone derivative, a strong antioxidant and radical scavenger. Suggested to play a role in prevention of cancer, possibly via the inhibition of fatty acid synthase activity.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


Certificats d'analyse (COA)

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Tian CF, et al.
Proceedings of the National Academy of Sciences of the USA, 201120260-201120260 (2012)
Luteolin inhibits viral-induced inflammatory response in RAW264. 7 cells via suppression of STAT1/3 dependent NF-kappaB and activation of HO-1
Liu CW, et al.
Free Radical Biology & Medicine, 95, 180-189 (2016)
Optimization of phenolic and flavonoid content and antioxidants capacity of pressurized liquid extraction from Dracocephalum kotschyi via circumscribed central composite
Kamali H, et al.
Journal of Supercritical Fluids, 107, 307-314 (2016)
Luteolin as a potential preventive and therapeutic candidate for Alzheimer's disease
Kwon Y.
Experimental Gerontology, 95, 39-43 (2017)
Crosstalk between jasmonic acid, ethylene and Nod factor signaling allows integration of diverse inputs for regulation of nodulation
Sun J, et al.
The Plant Journal, 46(6), 961-970 (2006)

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