Cytotoxic Lignans from
Fruits of <i>Cleistanthus
indochinensis</i>: Synthesis of Cleistantoxin Derivatives
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Abstract
Two new aryl-tetralin lignans, <b>1</b> and <b>2</b>, were isolated from the fruits of <i>Cleistanthus indochinensis</i> by bioassay-guided purification. Their structures were determined
by spectroscopic analysis including MS and 2D NMR. The absolute configurations
of <b>1</b> and <b>2</b> were established from examination
of their CD spectra. Compound <b>1</b> was cytotoxic against
KB cells with an IC<sub>50</sub> value of 0.022 μM, while compound <b>2</b> had weaker cytotoxicity, with an IC<sub>50</sub> value of
1.4 μM. When tested against other cancer cell lines (MCF-7,
MCF-7R, and HT29), <b>1</b> showed an IC<sub>50</sub> of 0.014
against MCF-7R cells and an IC<sub>50</sub> of 0.036 μM against
MCF-7 cells. A series of amide derivatives of a new lactone, homoderivatives
of <b>1</b>, were prepared. Of these derivatives, only compound <b>3</b> had weak cytotoxicity against KB cells