Short Route to the Total Synthesis of Natural Muricadienin and Investigation of Its Cytotoxic Properties

J Nat Prod. 2016 Aug 26;79(8):2039-44. doi: 10.1021/acs.jnatprod.6b00335.

Usein M Dzhemilev ¹, Vladimir A D'yakonov ¹, Regina A Tuktarova ¹, Lilya U Dzhemileva ¹ ² ³, Svetlana R Ishmukhametova ¹, Milyausha M Yunusbaeva ³, Armin de Meijere ⁴

Affiliations

1 Laboratory of Catalytic Synthesis, Institute of Petrochemistry and Catalysis of RAS (IPC RAS) , Prospect Octyabrya, 141, 450075, Ufa, Russian Federation.
2 Department of Immunology and Human Reproductive Health, Bashkir State Medical University , Lenin Street, 3, 450003, Ufa, Russian Federation.
3 Institute of Biochemistry and Genetics, Ufa Scientific Centre of Russian Academy of Sciences , Prospect Octyabrya, 71, 450054, Ufa, Russian Federation.
4 Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen , Tammannstrasse 2, 37077 Göttingen, Germany.

PMID: 27533261 DOI: 10.1021/acs.jnatprod.6b00335

Abstract

An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cyclomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and IIα, key cell cycle Enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney Cancer cells (IC50 0.39 μM).

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