2 research outputs found
Total Synthesis of Thelephantin O, Vialinin A/Terrestrin A, and Terrestrins B–D
The first total synthesis of natural, unsymmetrical 2′,3′-diacyloxy-<i>p</i>-terphenyls, thelephantin O (<b>1</b>) and terrestrins
C and D (<b>2</b> and <b>3</b>, respectively), was achieved
via a practical route which was also applicable to the synthesis of
the symmetrical diesters vialinin A/terrestrin A (<b>4</b>)
and terrestrin B (<b>5</b>). Compounds <b>1</b>–<b>5</b> exhibited cytotoxicity against cancer cells (HepG2 and Caco2)
with IC<sub>50</sub> values of 13.6–26.7 μmol/L
<i>p</i>‑Terphenyl Derivatives from the Mushroom Thelephora aurantiotincta Suppress the Proliferation of Human Hepatocellular Carcinoma Cells via Iron Chelation
A novel 2′,3′-dihydroxy-<i>p</i>-terphenyl
derivative, thelephantin O (TO), which has cancer-selective cytotoxicity,
was isolated. This study investigated the underlying basis of the
cytotoxicity of 2′,3′-dihydroxy-<i>p-</i>terphenyl
compounds in view of their ability to chelate metal ions. FeCl<sub>2</sub> significantly reduced TO-induced cytotoxicity, whereas several
other salts of transition metals and alkaline-earth metals did not.
A structure–activity relationship study using newly synthesized <i>p</i>-terphenyl derivatives revealed that <i>o</i>-dihydroxy substitution of the central benzene ring was necessary
for both the cytotoxicity and Fe<sup>2+</sup> chelation of the compounds.
Real-time PCR array and cell cycle analysis revealed that the 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<sub>2</sub>. Thus, it was concluded that Fe<sup>2+</sup> chelation
occurs upstream in the pivotal pathway of 2′,3′-dihydroxy-<i>p</i>-terphenyl-induced inhibition of cancer cell proliferation