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Chembiochem. 2014 Dec 15;15(18):2689-91. doi: 10.1002/cbic.201402447. Epub 2014 Oct 24.

Bioactive derivatives of isopropylstilbene from mutasynthesis and chemical synthesis.

Author information

1
Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, 60438 Frankfurt am Main (Germany).

Abstract

Isopropylstilbene is a natural product from Photorhabdus luminescens TT01, with multiple biological activities. A mutant deficient in the production of both anthraquinones and cinnamic acid was constructed, thus giving a clean background according to UV detection. This anthraquinone and stilbene deficient (ASD) mutant was used in mutasynthesis experiments to obtain new stilbene derivatives, which were detected by GC-MS. The structures of the new derivatives were confirmed by detailed MS analysis and then chemically synthesised; all of the natural and synthetic compounds were tested against protozoa that cause tropical diseases. Two compounds obtained by mutasynthesis showed the highest activity against Trypanosoma cruzi, the causative agent of Chagas disease, and Leishmania donovani, which causes leishmaniasis.

KEYWORDS:

Photorhabdus; biological activity; biomimetic synthesis; mutasynthesis; natural products

PMID:
25346446
DOI:
10.1002/cbic.201402447
[Indexed for MEDLINE]

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