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Trilobin & Trilobacin

 

 

Both Trilobacin and trilobin are member of the annonaceous acetogenin family of compounds.  Typically they are comprised of a long aliphatic chain bearing a terminal methyl substituted butenolide with one, two or three tetrahydrofuran rings located along the hydrocarbon chain.

 

Trilobacin was first isolated in 1992 from the stem bark of Asimina triloba Dunal (pawpaw tree)  by McLaughlin.  Trilobacin was found to be the first annonaceous acetogenin with the erythro relative configuration between the bis(THF) rings.  Trilobacin shows biological activity in the three-day NCI human cancer cell line in vitro screen against certain cell lines.

 

Trilobin was first isolated in 1995 from the same source as trilobacin.  It also has the same erythro configuration of the bis(THF) rings.  Trilobin exhibited significant biological activities in human solid tumor cytotoxicity tests against lung cancer, breast cancer and colon cancer cell lines.

 

Due to their high toxicity against several cancer cell lines, both trilobacin and trilobin are attractive targets for total synthesis.