Tongalides, Halogenated Butenolides from an Antarctic Delisea sp. Rhodophyte

ABSTRACT: Six new halogenated butenolides, tongalides A-C (1-3) and their acetylated congeners (4-6), were isolated from an extract of the Antarctic rhodophyte Delisea sp. that displayed significant antibiotic activity. The structures of the compounds were determined by analysis of data acquired by spectroscopic and spectrometric techniques including NMR, HRESIMS, optical rotation, and X-ray diffraction studies. The newly isolated compounds were assayed for antibacterial activity, but exhibited no growth inhibition of ESKAPE pathogens. The extract bioactivity was attributed to the previously reported Z-acetoxyfimbrolide A also isolated from the extract, providing further evidence that the exocyclic double bond is essential to the antibacterial activity of the structurally related fimbrolide class of metabolite.

Automated summary

Six new halogenated butenolides, tongalides A-C (1-3) and their acetylated congeners (4-6), were isolated from an extract of the Antarctic rhodophyte Delisea sp. The structures of the compounds were determined by various analytical techniques. The newly isolated compounds showed no antibacterial activity, while the extract's bioactivity was attributed to another compound.