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Common Name

Isorhamnetin

Systematic Name

3,4?,5,7-Tetrahydroxy-3?-methoxyflavone

Synonyms

3-methylquercetin

LM ID

LMPK12110002

Formula

C₁₆H₁₂O₇

Exact Mass

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316.058305

Status

Curated

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Classification

Biological Context

Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 µM).¹ Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 µM), which has an important role in the excretion of xenobiotics at the kidney and liver.² It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.^3,4,5,6

This information has been provided by Cayman Chemical

References

1. Kawasaki, T., Ito, H., and Omote, H. Components of foods inhibit a drug exporter, human multidrug and toxin extrusion transporter 1. Biol. Pharm. Bull. 37(2), 292-297 (2014).

2. Xu, S.L., Choi, R.C.Y., Zhu, K.Y., et al. Isorhamnetin, a flavonol aglycone from Ginkgo biloba L., induces neuronal differentiation of cultured PC12 cells: Potentiating the effect of nerve growth factor. Evid. Based Complement. Alternat. Med. 278273 (2012).

3. Sun, J., Sun, G., Meng, X., et al. Isorhamnetin protects against doxorubicin-induced cardiotoxicity in vivo and in vitro. PLoS One 8(5), 1-14 (2014).

4. Saud, S.M., Young, M.R., Jones-Hall, Y.L., et al. Chemopreventive activity of plant flavonoid isorhamnetin in colorectal cancer is mediated by oncogenic Src and β-catenin. Cancer Res. 73(17), 5473-5484 (2013).

5. Ramachandran, L., Manu, K.A., Shanmugam, M.K., et al. Isorhamnetin inhibits proliferation and invasion and induces apoptosis through the modulation of peroxisome proliferator-activated receptor γ activation pathway in gastric cancer. J. Biol. Chem. 287(45), 38028-38040 (2012).

6. Nagao, A., Seki, M., and Kobayashi, H. Inhibition of xanthine oxidase by flavonoids. Biosci. Biotechnol. Biochem. 63(10), 1787-1790 (1999).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ginkgo biloba (#3311)

Ginkgoopsida (#29811)

Isorhamnetin, A Flavonol Aglycone from Ginkgo biloba L., Induces Neuronal Differentiation of Cultured PC12 Cells: Potentiating the Effect of Nerve Growth Factor.,
Evid Based Complement Alternat Med, 2012

Pubmed ID: 22761636