p-Terphenyl derivatives from the mushroom Thelephora aurantiotincta
suppress the proliferation of human hepatocellular carcinoma cells via
iron chelation.
Norikura T, Fujiwara K, Yanai T, Sano Y, Sato T, Tsunoda T, Kushibe K,
Todate A, Morinaga Y, Iwai K, Matsue H.
J Agric Food Chem. 2013 Jan 22.

Abstract
We isolated a novel 2',3'-dihydoroxy-p-terphenyl derivatives 2',3'-
dihydoroxy-p-terphenyl derivative, thelephantin O (TO), which has
cancer-selective cytotoxicity.
In this study, we investigated the underlying basis of the
cytotoxicity of 2',3'-dihydroxy-p-terphenyl compounds in view of their
ability to chelate metal ions.
FeCl(2) significantly reduced TO-induced cytotoxicity, while several
other salts of transition metals and alkaline-earth metals did not.
A structure-activity relationship study using newly synthesized p-
terphenyl derivatives revealed that ortho-dihydroxy substitution of
the central benzene ring was necessary for both the cytotoxicity and
Fe(2+) chelation of the compounds.
Real-time PCR array and cell cycle analysis revealed that TO-induced
cytotoxicity was attributed to cell cycle arrest at the G1 phase via
well-known cell cycle-mediated genes.
The TO-induced changes in the cell cycle and gene expression were
completely reversed by the addition of FeCl(2).
Thus, we conclude that Fe(2+) chelation occurs upstream in the pivotal
pathway of 2',3'-dihydroxy-p-terphenyl-induced inhibition of cancer
cell proliferation.

PMID:23339435


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