Luteolin (CAS 491-70-3)

5.0(1)

Alternate Names: Luteolin is also known as 3′,4′,5,7-Tetrahydroxyflavone.

Application: Luteolin is an inhibitor of LPS-induced TNF-α, IL-6 and inducible nitric oxide production and blocker of NF-κB and AP-1 activation.

CAS Number: 491-70-3

Purity: ≥98%

Molecular Weight: 286.24

Molecular Formula: C₁₅H₁₀O₆

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

* Refer to Certificate of Analysis for lot specific data (including water content).

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Luteolin is an antioxidant flavonoid and a free radical scavenger. Luteolin inhibits rat liver cytosolic glutathione S-transferase activity and soybean and reticulocyte 15-LO (15-lipoxygenases). Luteolin also shows cytotoxic effects on Raji lymphoma cells. Incubation of the non-tumor cell line C3H10T½CL8 with Luteolin results in induction of p53 accumulation and apoptosis, with apoptosis occurring at the G2/M phase of the cell cycle.

References

1. Korkina, L.G., and Afanasev, I.B. 1997. Adv. Pharmacol. 38, 151.
2. Plaumann, B., et al. 1996. Oncogene 13, 1605.
3. Ramanathan, R., et al. 1994. Free Radic. Biol. Med. 16, 43.
4. Shimoi, L., et al. 1994. Carcinogenesis 15, 2669.
5. Ueda, H., Yamazaki, C., and Yamazaki, M.Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. Biological and Pharmaceutical Bullentin 25(9), 1197-1202 (2002).
6. Sadik, C.D., Sies, H., and Schewe, T.Inhibition of 15-lipoxygenases by flavonoids: Structure-activity relations and mode of action. Biochemical Pharmacology 65(5), 773-781 (2003).
7. Sartor, L., Pezzato, E., Dell′Aica, I., et al.Inhibition of matrix-proteases by polyphenols: Chemical insights for anti-inflammatory and anti-invasion drug design. Biochemical Pharmacology 64(2), 229-237 (2002).

Appearance :

Powder

Physical State :

Solid

Solubility :

Soluble in aqueous alkaline solutions (1.4 mg/ml), ethanol (~5 mg/ml), DMSO, 1eq. NaOH (5 mM), DMF (~20 mg/ml), 1:5 solution of DMF:PBS(pH7.2) (`~1 mg/ml), water (1 mg/ml at 25° C), and methanol.

Storage :

Store at 4° C

Melting Point :

330° C (lit.)

Boiling Point :

~616.1° C at 760 mmHg (Predicted)

Density :

~1.7 g/cm³ (Predicted)

Refractive Index :

n²⁰_D 1.77 (Predicted)

IC50 :

soybean and reticulocyte 15-lipoxygenases: IC₅₀ = 0.6 µM; HIV-1(IIIB): IC₅₀ = 16 µM (H9); HIV-1(IIIB): EC₅₀50 = 10 µM (H9); Cyclooxygenase-2: IC₅₀ = 2.5 ug.mL-1 (human); Cytochrome P450 1B1: IC₅₀ = 79 nM (human); Xanthine dehydrogenase: IC₅₀ = 550 nM (human); Dopamine transporter: EC₅₀50 = 1450 nM (rat); H9c2 : EC₅₀50 = 5530 nM (rat)

Ki Data :

Cytochrome P450 1B1: K_i= 56 nM (human); 3-oxoacyl-acyl-carrier protein reductase: K_i= 800 nM (Plasmodium falciparum); Cytochrome P450 1A1: K_i= 890 nM (human); Adenosine A1 receptor: K_i= 1550 nM (rat); Xanthine dehydrogenase: K_i= 1900 nM (Bos taurus)

pK Values :

pK_a: 6.50

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

RTECS :

LK9275210

PubChem CID :

5280445

Merck Index :

14: 5614

MDL Number :

MFCD00017309

EC Number :

207-741-0

Beilstein Registry :

292084

SMILES :

C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O

Download SDS (MSDS)

Certificate of Analysis

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