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Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives.

Journal of natural products (2012-09-04)
Van Trinh Thi Thanh, Van Cuong Pham, Huong Doan Thi Mai, Marc Litaudon, Françoise Guéritte, Pascal Retailleau, Van Hung Nguyen, Van Minh Chau
ABSTRACT

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

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Picropodophyllotoxin, ≥96% (HPLC), powder
Sigma-Aldrich
Podophyllotoxin