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Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers.

Bioorganic & medicinal chemistry (2009-11-19)
Benedikt Cramer, Henning Harrer, Kazuhiko Nakamura, Daisuke Uemura, Hans-Ulrich Humpf
ABSTRACT

The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the l-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ochratoxin A−BSA conjugate from Aspergillus ochraceus
Supelco
Ochratoxin A, from Aspergillus ochraceus, reference material
Sigma-Aldrich
Ochratoxin A, from Petromyces albertensis, ≥98% (HPLC)