Identification of novel anti-Candida cassane type diterpenes from the roots bark of Swartzia simplex (Sw.) Spreng

Favre-Godal, Quentin and Dorsaz, Stephane and Queiroz, Emerson F. and Marcourt, Laurence and Ebrahimi, Samad Nejad and Allard, Pierre-Marie and Voinesco, Francine and Hamburger, Matthias and Gupta, Mahabir P. and Gindro, Katia and Sanglard, Dominique and Wolfender, Jean-Luc. (2015) Identification of novel anti-Candida cassane type diterpenes from the roots bark of Swartzia simplex (Sw.) Spreng. Journal of Natural Products, 78 (12). pp. 2994-3004.

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A dichloromethane extract of the roots from the Panamanian plant Swartzia simplex exhibited a strong antifungal activity in a bioautography assay against a genetically modified hypersusceptible strain of Candida albicans. At-line HPLC activity based profiling of the crude extract enabled a precise localization of the antifungal compounds, and dereplication by UHPLC-HRESIMS indicated the presence of potentially new metabolites. Transposition of the HPLC reversed-phase analytical conditions to medium-pressure liquid chromatography (MPLC) allowed an efficient isolation of the major constituents. Minor compounds of interest were isolated from the MPLC fractions using semipreparative HPLC. Using this strategy, 14 diterpenes (1–14) were isolated, with seven (5–10, 14) being new antifungal natural products. The new structures were elucidated using NMR spectroscopy and HRESIMS analysis. The absolute configurations of some of the compounds were elucidated by electronic circular dichroism spectroscopy. The antifungal properties of these compounds were evaluated as their minimum inhibitory concentrations in a dilution assay against both hypersusceptible and wild-type strains of C. albicans and by assessment of their antibiofilm activities. The potential cytological effects on the ultrastructure of C. albicans of the antifungal compounds isolated were evaluated on thin sections by transmission electron microscopy.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Pharmazeutische Biologie (Hamburger)
UniBasel Contributors:Hamburger, Matthias
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:28 Nov 2017 09:34
Deposited On:23 Aug 2016 08:39

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