The discovery and characterization of marine natural products have long provided sources of rich structural and biological diversity. We report the identification and characterization of a previously unknown pyrroloiminoquinone natural product, Macrophilone A, whose structure was assigned utilizing various long-range NMR couplings and confirmed by a concise five-step total synthesis. Macrophilone A and a synthetic analog were found to have potent biological activity, including an increase in intracellular reactive oxygen species (ROS) levels and submicromolar cytotoxicity toward lung adenocarcinoma cells.

Isolation, functional evaluation, and total synthesis of Macrophilone A: A biologically active iminoquinone from the marine hydroid <i>Macrorhynchia philippina</i>

254th National Meeting (2017)

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Isolation, functional evaluation, and total synthesis of Macrophilone A: A biologically active iminoquinone from the marine hydroid Macrorhynchia philippina