Abstract
As part of an ongoing program to identify new bioactive compounds from Irish marine bioresources, we selected the subtidal sponge Spongosorites calcicola for chemical study, as fractions of this species displayed interesting cytotoxic bioactivities and chemical profiles. The first chemical investigation of this marine species led to the discovery of two new bisindole alkaloids of the topsentin family, together with six other known indole alkaloids. Missing the usual central core featured by the representatives of these marine natural products, the new metabolites may represent key biosynthetic intermediates for other known bisindoles. These compounds were found to exhibit weak cytotoxic activity against HeLa tumour cells, suggesting a specificity towards previously screened carcinoma and leukaemia cells.
Highlights
Marine sponges are well-recognised as producers of a diverse array of bioactive metabolites for defence, competition, and communication [1]
With the 2D structure of 1 solved, the absolute configuration of the unique C-8 chiral centre was assigned through the comparison between experimental and predicted electronic circular dichroism (ECD) spectra (Figure 2)
Members of the bisindole alkaloid family have been previously reported with a large array of study noted that the cytotoxicity of Spongosorites bisindoles is cell-line dependent with only weak activity reported against other cell lines screened [10]
Summary
Marine sponges are well-recognised as producers of a diverse array of bioactive metabolites for defence, competition, and communication [1] For this reason, these invertebrates have been the subjects of extensive chemical study over the past half century. The sponge genus Spongosorites has been reported to produce many brominated bisindole alkaloids belonging to four classes that differ in the linkage between the indole moieties [3,4] These bisindoles include topsentin and spongotine derivatives with imidazole or dihydroimidazole linkages [5,6], and dragmacidin and hamacanthin derivatives characterised by a pyrazine or piperazine. S. calcicola forfeaturing, the first time, an absence of activity two newalkaloids bisindolefrom alkaloids from the Irish spongefeaturing, S. calcicola for the first time, cycle between the two indolethe rings They could represent key intermediates the biosynthesis an absence of cycle between twoAs indole.
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