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Denigrins and Dactylpyrroles, Arylpyrrole Alkaloids from a Dactylia sp. Marine Sponge

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posted on 05.11.2020, 21:52 by Unwoo Kang, Laura K. Cartner, Dongdong Wang, Chang-Kwon Kim, Cheryl L. Thomas, Girma M. Woldemichael, Berkley E. Gryder, John F. Shern, Javed Khan, Cristiana Castello-Branco, Edward C. Sherer, Xiao Wang, Erik L. Regalado, Kirk R. Gustafson
Seven new arylpyrrole alkaloids (17), along with four known compounds, were isolated from an extract of a Dactylia sp. nov. marine sponge, and their structures were elucidated by interpretation of NMR and MS spectroscopic data. Denigrins D–G (14) have highly substituted pyrrole or pyrrolone rings in their core structures, while dactylpyrroles A–C (57) have tricyclic phenanthrene cores. Due to the proton-deficient nature of these scaffolds, key heteronuclear correlations from 1H–15N HMBC and LR-HSQMBC NMR experiments were used in the structure assignment of denigrin D (1). Dictyodendrin F (8), a previously described co-metabolite, inhibited transcription driven by the oncogenic PAX3-FOXO1 fusion gene with an IC50 value of 13 μM.