Synthesis and initial biological evaluation of myxocoumarin BElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ob02273a

• Main Authors: Müller, Jonas I, Kusserow, Kalina, Hertrampf, Gesa, Pavic, Aleksandar, Nikodinovic-Runic, Jasmina, Gulder, Tobias A. M
• Format: Journal Article
• Published: 13.02.2019
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c8ob02273a

The myxocoumarins A and B from Stigmatella aurantiaca MYX-030 are natural products featuring unusual nitro- and long-chain alkyl substitution. While myxocoumarin A was shown to exhibit strong antifungal properties, the antifungal potential of myxocoumarin B was not yet assessed due to low production titers during initial isolation. We therefore developed a total synthesis of myxocoumarin B that involves a late-stage Pd-catalyzed nitration of the coumarin core. The availability of synthetic material facilitated the initial evaluation of the bioactivity of myxocoumarin B, which revealed a lack of activity against medically relevant Candida sp. and low cytotoxicity in vitro against human fibroblasts (MRC-5) and in vivo (zebrafish). The first total synthesis of myxocoumarin B along with its initial biological evaluation in antifungal and cytotoxicity assays are reported.