LIPID MAPS

Common Name

Tectorigenin

Systematic Name

5,7,4'-Trihydroxy-6-methoxyisoflavone

Synonyms

LM ID

LMPK12050385

Formula

C₁₆H₁₂O₆

Exact Mass

Calculate m/z

300.06339

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View NP-MRD ID(NMR) spectrum

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Isoflavonoids [PK1205]

Tectorigenin is an isoflavonoid that has been found in B. chinensis and has diverse biological activities and is an active metabolite of the flavonoid glycoside and phytoestrogen tectoridin .^1,2,3,4,5 It is formed from tectoridin by gut microbiota.¹ Tectorigenin scavenges hydroxyl and superoxide radicals in cell-free assays (IC50s = 87 and 46.62 µg/ml, respectively) and inhibits the formation of thiobarbituric acid reactive substances (TBARS) in egg yolk (IC50 = 23 µg/ml).² It inhibits the production of prostaglandin E2 (PGE2) induced by the PKC activator 12-O-tetradecanoylphorbol 13-acetate (TPA) or the sarcoplasmic/endoplasmic reticulum Ca2+-ATPase (SERCA) and endoplasmic reticulum (ER) stress inducer thapsigargin in isolated rat peritoneal macrophages when used at concentrations of 3, 10, or 30 µM.³ Tectorigenin (10 µg/ml) reduces cell death induced by hydrogen peroxide (H2O2) and increases catalase levels and activity in V79-4 Chinese hamster lung fibroblasts.⁴ In vivo, tectorigenin (100 mg/kg per day) prevents increases in hepatic levels of malondialdehyde (MDA) and blood levels of alanine transaminase (ALT) and aspartate aminotransferase (AST) and decreases in hepatic superoxide dismutase (SOD), catalase, and glutathione peroxidase (GPX) activities in a rat model of liver injury induced by carbon tetrachloride (CCl4).⁵

This information has been provided by Cayman Chemical

References

1. Han, T., Cheng, G., Liu, Y., et al. In vitro evaluation of tectoridin, tectorigenin and tectorigenin sodium sulfonate on antioxidant properties. Food Chem. Toxicol. 50(2), 409-414 (2012).

2. Kim, Y.P., Yamada, M., Lim, S.S., et al. Inhibition by tectorigenin and tectoridin of prostaglandin E2 production and cyclooxygenase-2 induction in rat peritoneal macrophages. Biochim. Biophys. Acta 1438(3), 399-407 (1999).

3. Chen, Y., Song, W., Peng, Z.H., et al. Identification of metabolites of tectoridin in-vivo and in-vitro by liquid chromatography-tandem mass spectrometry. J. Pharm. Pharmacol. 60(6), 709-716 (2008).

4. Zhang, R., Piao, M.J., Oh, M.C., et al. Protective effect of an isoflavone, tectorigenin, against oxidative stress-induced cell death via catalase activation. J. Cancer Prev. 21(4), 257-263 (2016).

5. Jung, S.H., Lee, Y.S., Lim, S.S., et al. Antioxidant activities of isoflavones from the rhizomes of Belamcanda chinensis on carbon tetrachloride-induced hepatic injury in rats. Arch. Pharm. Res. 27(2), 184-188 (2004).