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

J Nat Prod. 2020 Nov 25;83(11):3464-3470. doi: 10.1021/acs.jnatprod.0c01103. Epub 2020 Nov 5.

Abstract

Seven new arylpyrrole alkaloids (1-7), 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 (1-4) have highly substituted pyrrole or pyrrolone rings in their core structures, while dactylpyrroles A-C (5-7) 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.

Publication types

  • Research Support, N.I.H., Intramural

MeSH terms

  • Alkaloids / chemistry*
  • Animals
  • Carbon-13 Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Porifera / chemistry*
  • Proton Magnetic Resonance Spectroscopy / methods
  • Pyrroles / chemistry*

Substances

  • Alkaloids
  • Pyrroles