title: Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers.
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.
authors.affiliation: Institut für Lebensmittelchemie, Westfälische Wilhelms-Universität Münster, Corrensstrasse 45, 48149 Münster, Germany. cramerb@uni-muenster.de
authors.forename: Benedikt
authors.initials: B
authors.lastname: Cramer
authors.forename: Henning
authors.initials: H
authors.lastname: Harrer
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Nakamura
authors.forename: Daisuke
authors.initials: D
authors.lastname: Uemura
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Humpf
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D009793:Ochratoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D003603:Cytotoxins; D009793:Ochratoxins; C025589:ochratoxin A