LIPID MAPS

Common Name

Baicalein

Systematic Name

5,6,7-Trihydroxyflavone

Synonyms

Noroxylin

LM ID

LMPK12111095

Formula

C₁₅H₁₀O₅

Exact Mass

Calculate m/z

270.052825

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View NP-MRD ID(NMR) spectrum

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

Baicalein is a flavonoid originally isolated from the roots of S. baicalensis that has diverse biological activities.¹ It inhibits human platelet 12-lipoxygenase (12-LO) and human reticulocyte 15-LO-1 (IC50s = 0.64 and 1.6 µM, respectively) but is less potent at 15-LO-1 when the detergent Triton-X is present (IC50 = 38 µM).² Baicalein inhibits lipid peroxidation, as assessed by production of thiobarbituric acid (TBARS; IC50 = 5 µM), and inhibits growth of Huh-7, KIM-1, and HLF human hepatocellular carcinoma cells (IC50s = 17-70 µg/ml).^3,4 Baicalein increases intracellular calcium levels by increasing release from the endoplasmic reticulum and via PKC-dependent calcium channels in the plasma membrane, leading to increases in reactive oxygen species (ROS), caspase-9 and -3 activation, and apoptosis in ZR-75-1 human breast cancer cells.⁵ Baicalein increases levels of peroxisome proliferator-activated receptor β/δ (PPARβ/δ) in BV-2 microglia and primary microglia and decreases the level of 12- and 15-LO products.⁶ It also decreases symptoms of experimental autoimmune encephalomyelitis (EAE) in a mouse model of multiple sclerosis, when administered at a dose of 75 mg/kg per day.

This information has been provided by Cayman Chemical

References

1. Gao, D., Sakurai, K., Katoh, M., et al. Inhibition of microsomal lipid peroxidation by baicalein: A possible formation of an iron-baicalein complex. Biochem. Mol. Biol. Int. 39(2), 215-225 (1996).

2. Matsuzaki, Y., Korokawa, N., Terai, S., et al. Cell death induced by baicalein in human hepatocellular carcinoma cell lines. Jpn. J. Cancer Res. 87(2), 170-177 (1996).

3. Shibata, K., Iwata, S., and Nakamura, M. Baicalin, a new flavone-glucuronic acid compound from the roots of Scutellaria baicalensis. Acta Phytochimica 1, 105-139 (1923).

4. Deschamps, J.D., Kenyon, V.A., and Holman, T.R. Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases. Bioorg. Med. Chem. 14(12), 4295-4301 (2006).

5. Chang, H.-T., Chou, C.-F., Kuo, D.-H., et al. The mechanism of Ca2+ movement in the involvement of baicalein-induced cytotoxicity in ZR-75-1 human breast cancer cells. J. Nat. Prod. 78(7), 1624-1634 (2015).

6. Xu, J., Zhang, Y., Xiao, Y., et al. Inhibition of 12/15-lipoxygenase by baicalein induces microglia PPARβ/δ: A potential therapeutic role for CNS autoimmune disease. Cell Death Dis. 4(4), e569 (2013).