LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Galangin

Systematic Name

3,5,7-Trihydroxyflavone

Synonyms

Norizalpinin

LM ID

LMPK12111653

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

Classification

Biological Context

Galangin is a flavonoid naturally found in herbs used in traditional medicine. Like many flavonoids, it has potent antioxidant properties.¹ It also has anti-inflammatory actions related to suppression of signaling through NF-κB in mice.² Galangin acts as an antagonist of the aryl hydrocarbon receptor, inducing apoptosis in cancer cells.^3,4,5 It also inhibits cytochrome P450 isoform 1A1 with an IC50 value of less than 1 µM.⁶

This information has been provided by Cayman Chemical

References

1. Duthie, G., and Morrice, P. Antioxidant capacity of flavonoids in hepatic microsomes is not reflected by antioxidant effects in vivo. Oxid. Med. Cell. Longev. 2012, 1-7 (2012).

2. Forbes, A.M., Lin, H., Meadows, G.G., et al. Synthesis and anticancer activity of new flavonoid analogs and inconsistencies in assays related to proliferation and viability measurements. Int. J. Oncol. 45(2), 831-842 (2014).

3. Quadri, S.A., Qadri, A.N., Hahn, M.E., et al. The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis. Mol. Pharmacol. 58(3), 515-525 (2000).

4. Zha, W.J., Qian, Y., Shen, Y., et al. Galangin abrogates ovalbumin-induced airway inflammation via negative regulation of NF-κB. Evid. Based Complementary Altern. Med. 2013, 1-15 (2013).

5. Zhang, W., Lan, Y., Huang, Q., et al. Galangin induces B16F10 melanoma cell apoptosis via mitochondrial pathway and sustained activation of p38 MAPK. Cytotechnology 65(3), 447-455 (2013).

6. Ciolino, H.P., and Yeh, G.C. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br. J. Cancer 79(9-10), 1340-1346 (1999).