Denigrins H–L: Sulfated Derivatives of Denigrins D and E from a New Zealand <i>Dictyodendrilla</i> c.f. <i>dendyi</i> Marine Sponge

Abstract

Five new sulfated arylpyrrole and arylpyrrolone alkaloids, denigrins H–L (1–5), along with two known compounds, dictyodendrin B and denigrin G, were isolated from an extract of a New Zealand Dictyodendrilla c.f. dendyi marine sponge. Denigrins H–L represent the first examples of sulfated denigrins, with denigrins H and I (1–2), as derivatives of denigrin D, containing a pyrrolone core, and denigrins J–L (3–5), as derivatives of denigrin E (6), containing a pyrrole core. Their structures were elucidated by interpretation of 1D and 2D NMR spectroscopic data, ESI, and HR-ESI-MS spectrometric data, as well as comparison with literature data. Compounds 1–5, along with six known compounds previously isolated from the same extract, showed minimal cytotoxicity against the HeLa cervical cancer cell line.

Keywords

• denigrin
• sponge
• pyrrole
• pyrrolone
• sodium sulfate
• alkaloids