LIPID MAPS

Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity.^1,2 Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects.³ Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 µM) and has also been shown to activate a PPARα promoter.⁴ Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis.⁵ Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 µM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 µM).^6,7

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References

1. Khan, S.I., Zhao, J., Khan, I.A., et al. Potential utility of natural products as regulators of breast cancer-associated aromatase promoters. Reprod. Biol. Endocrinol. 9:91, (2011).

2. Wang, L., Waltenberger, B., Pferschy-Wenzig, E.M., et al. Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review. Biochem. Pharmacol. 92(1), 73-89 (2014).

3. Thors, L., Burston, J.J., Alter, B.J., et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br. J. Pharmacol. 160(3), 549-560 (2010).

4. Medjakovic, S., and Jungbauer, A. Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor. J. Steroid Biochem. Mol. Biol. 108(1-2), 171-177 (2008).

5. Patisaul, H.B., and Jefferson, W. The pros and cons of phytoestrogens. Front. Neuroendocrinol. 31(4), 400-419 (2010).

6. Rasbach, K.A., and Schnellmann, R.G. Isoflavones promote mitochondrial biogenesis. J. Pharmacol. Exp. Ther. 325(2), 536-543 (2008).

7. Evans, B.A., Griffiths, K., and Morton, M.S. Inhibition of 5α-reductase in genital skin fibroblasts and prostate tissue by dietary lignans and isoflavonoids. J. Endocrinol. 147(2), 295-302 (1995).