Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone. Issue 44 (2nd November 2016)

• Record Type: Journal Article
• Authors: Boufridi, Asmaa; Petek, Sylvain; Evanno, Laurent; Beniddir, Mehdi A.; Debitus, Cécile; Buisson, Didier; Poupon, Erwan
• Is Part Of: Tetrahedron letters. Volume 57:Issue 44(2016)
• Page Start: 4922
• Page End: 4925
• Publication Date: 2016-11-02
• Subjects: Ilimaquinone -- Biotransformation -- Epoxidation -- Marine sponge -- Marine natural substance; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.075
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An intrinsically cytotoxic natural product was chosen for bioconversion studies. Original transformations were observed with a Mucor sp. strain. Stereoselectivity of epoxidation differs from classic epoxidation reagents. New analogs are also cytotoxic. Abstract: Highly biologically active marine sesquiterpene ilimaquinone was selected for chemical modifications. Its biotransformation was investigated using a combinatorial approach as an original way to screen different strains of microorganisms. Mucor circinelloides ATCC 8541 was able to structurally modify ilimaquinone into three different compounds. A stereospecific epoxidation was observed and compared to chemical epoxidation. A hydroxylation of the decalin ring was also observed as well as an unexpected substitution on the quinone ring by ethanolamine. Compounds were evaluated against several cell lines.