Patrick Still - Synthesis and Antitumor Activity of Ellagic Acid Peracetate.

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      Publication Details (including relevant citation   information):

    Yulin Ren, Min Wei, Patrick C. Still, Shunzong Yuan, Youcai Deng, Xiaozhuo Chen, Klaus Himmeldirk, A. Douglas Kinghorn, and Jianhua Yu (2012). Synthesis and Antitumor Activity of Ellagic Acid Peracetate.ACS Medicinal Chemistry Letters 3: 631-636.


      Ellagic acid (1) was synthesized for the first   time from methyl gallate through α-pentagalloylglucose (α-PGG),   and ellagic acid peracetate   (3,4,3′,4′-tetra-O-acetylellagic acid,   2) was derived from 1 by   acetylation. Oral administration of 2 suppressed   melanoma growth significantly in C7BL/6 immunocompetent mice   without having any effect on natural killer (NK) cell activity.   Comparison of the immunoenhancing activities of   1 and 2 indicated that the   latter compound increased white blood cell quantities in   peripheral blood and immune cells enriched from the bone marrow   and liver of mice. Therefore, both the antitumor efficacy and the   immunity enhancement by 2 were greater than   those by 1. In addition, on oral administration,   neither 1 nor 2 resulted in   whole body, liver, or spleen weight changes of normal, tumor-free   mice, indicating that these compounds are potentially nontoxic to   mice. It was shown that ellagic acid peracetate   (2) inhibits B16 melanoma cell growth in vitro   and induces B16 cell apoptosis, corresponding to BCL-2   down-regulation. Collectively, the present data imply that   2 can suppress tumor growth by enhancing mouse   immunity and inducing tumor cell apoptosis without apparent side   effects.

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