Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone

Asmaa Boufridi; Sylvain Petek; Laurent Evanno; Mehdi A. Beniddir; Cécile Debitus; Didier Buisson; Erwan Poupon

doi:10.1016/j.tetlet.2016.09.075

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Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone

Journal article

Peer reviewed

Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone

Asmaa Boufridi, Sylvain Petek, Laurent Evanno, Mehdi A. Beniddir, Cécile Debitus, Didier Buisson and Erwan Poupon

Tetrahedron Letters, Vol.57(44), pp.4922-4925

2016

DOI: https://doi.org/10.1016/j.tetlet.2016.09.075

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Abstract

Natural products and bioactive compounds

Organic chemistry

ilimaquinone

biotransformation

epoxidation

marine sponge

marine natural substance

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.

Details

Title: Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone
Authors: Asmaa Boufridi (Author) - University of Paris-Saclay
Sylvain Petek (Author) - European Institute for Marine Studies
Laurent Evanno (Author) - University of Paris-Saclay
Mehdi A. Beniddir (Author) - University of Paris-Saclay
Cécile Debitus (Author) - European Institute for Marine Studies
Didier Buisson (Author) - Muséum national d'Histoire naturelle
Erwan Poupon (Author) - Institut des Neurosciences Paris-Saclay
Publication details: Tetrahedron Letters, Vol.57(44), pp.4922-4925
Publisher: Elsevier Ltd.
DOI: 10.1016/j.tetlet.2016.09.075
ISSN: 1873-3581
Organisation Unit: School of Science, Technology and Engineering; University of the Sunshine Coast, Queensland; Centre for Bioinnovation; School of Health - Biomedicine
Language: English
Record Identifier: 99650998402621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Organic

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