Abstract
The Red Sea specimen of the marine sponge Hyrtios erectus (order Dictyoceratida) was found to contain scalarane-type sesterterpenes. 12-O-deacetyl-12,19-di-epi-scalarin (14), a new scalarane sesterterpenoid, along with fourteen previously-reported scalarane-type sesterterpenes (1–13 and 15) have been isolated. The chemical structures of the isolated compounds were elucidated on the basis of detailed 1D and 2D NMR spectral data and mass spectroscopy, as well as by comparison with reported data. The anti-Helicobacter pylori, antitubercular and cytotoxic activities of all fifteen compounds were evaluated to reveal the potency of Compounds 1, 2, 3, 4, 6, 7 and 10. Amongst these, Compounds 1, 3, 4, 6 and 10 displayed a promising bioactivity profile, possessing potent activities in the antitubercular and anti-H. pylori bioassay. Compounds 2 and 7 showed the most promising cytotoxic profile, while Compounds 1 and 10 showed a moderate cytotoxic profile against MCF-7, HCT-116 and HepG2 cell lines.
Highlights
Marine sponges of the genus Hyrtios, order Dictyoceratida, family Thorectidae, occur often in tropical and subtropical sea waters and frequently form the dominant habitat on coral reefs
In the course of our ongoing efforts to identify drugs from the sea [2,3,52], we have studied and investigated the extract of the Red Sea marine sponge Hyrtios erectus (Figure 1)
Successive fractionation of the lipophilic fraction obtained from the methanolic extract of the sponge using silica gel column chromatography followed by final purification on semipreparative reversed phase HPLC column afforded fifteen pure isolated compounds (1–15) containing a scalarane-type framework, of which Compound 14 was assigned as a new scalarane sesterterpenoid
Summary
Marine sponges of the genus Hyrtios, order Dictyoceratida, family Thorectidae, occur often in tropical and subtropical sea waters and frequently form the dominant habitat on coral reefs. Previous biological and chemical investigations of the genus Hyrtios and their derived microbial symbionts have showed the presence of numerous natural products possessing a variety of important biological activities and unique structure including scalarane-type sesterterpenes [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21], sesquiterpenes [22,23,24], acyclic triterpenoids [25], macrolides [26,27,28,29], steroids [30], indole and β-carboline alkaloids [24,31,32,33,34,35,36,37,38]. Other biological activities of scalaranes include cytotoxic [3,4,5,13,18,19,20,41,42], antifeedant [43,44], antitubercular [6], antimicrobial [45,46], ichthyotoxic [47], anti-inflammatory [14,48], platelet aggregation inhibition [49,50] and nerve growth factor synthesis-stimulation [21,51].
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