Abstract
A comprehensive review on the chemistry of Spongia sp. is here presented, together with the biological activity of the isolated compounds. The compounds are grouped in sesquiterpene quinones, diterpenes, C21 and other linear furanoterpenes, sesterterpenes, sterols (including secosterols), macrolides and miscellaneous compounds. Among other reports we include studies on the intraspecific diversity of a Mediterranean species, compounds isolated from associated sponge and nudibranch and compounds isolated from S. zimocca and the red seaweed Laurentia microcladia. Under biological activity a table of the reported biological activities of the various compounds and the biological screening of extracts are described. The present review covers the literature from 1971 to 2015.
Highlights
Marine sponges have been considered as a very remarkable field for the discovery of bioactive natural products, being so far the most studied source of marine natural products [1]
From a Spongia sp. collected in Australia, the isolation of the unusual cyclosmenospongine 6 was reported by Utkina et al [11], together with the already known metabolites smenospongiarine 7, ilimaquinone 8 and smenospongine 9 (Figure 3)
For 178 the main difference in respect to the 1H NMR data of was the H-16 resonance, consistent with being the C-16 epimer. Both compounds underwent decomposition before absolute stereochemistry, optical rotation and biological activity could be determined. He et al [73] reported the isolation of the new spongianolides A–F 180–185 (Figure 53) from a SMpaor.nDgriuagssp2.01c6o, l1l4e,c1t3e9d in Florida in a bioguided study of protein kinase C (PKC) inhibitors. 35 of 74
Summary
Marine sponges have been considered as a very remarkable field for the discovery of bioactive natural products, being so far the most studied source of marine natural products [1]. SSeessqquuitieterrppeenneeQQuuiinnoonneess UUrrbbaann aanndd CCaappoonn [[99]] rreeppoorrtteedd tthhee iissoollaattiioonn ooff 55--eeppii--iissoossppoonnggiiaaqquuiinnoonnee 11,, ttooggeetthheerr wwiitthh. X-ray fluorescence spectroscopy confirmed potassium as the main counter ion (sodium was presFeignutrien2t.rSatcruecatumreosuonftcso).mTphoeunisdo3la, tdeedhycdormocpyocluonspdosnpgriaoqvueidnotnoe-b1e4raensdpospnosnibglieaqfuoirnotohnnee 5a5..ntibiotic activity of the extract against a range of test microorganisms. Collected in Australia, the isolation of the unusual cyclosmenospongine 6 was reported by Utkina et al [11], together with the already known metabolites smenospongiarine 7, ilimaquinone 8 and smenospongine 9 (Figure 3). Comparison with the known metachromin G sho5wofe7d1 that the main differences were the presence of a substituted double bond bearing a methyl group in epxlaocmeeothf yalneneex.oAmepthheynletnhey. [[2244]] rreeepppoorrtteedd tthhee iissoollaattiioonn ooff tthhee nneeww ssppoonnggiiaa--1133((1166)),,1144--ddiieenn--1199--ooiiccc aacciiddd 4411,, ssppoonnggiiaaC--1a13p3((e11l6l6e)),,11e4t4--dadlii.eenn[n2---4111]999---raaaelllp4o42r2teaadnndtdhessppisooonnlgagtiiiaao--n1133o((11f666t)))h,,,111e444--n-dddeiiwieeennneesep4o443n33gffiraroo-1mm3(1aa6)S,S1..4-oodffffiifieiccniinn-1aa9llii-ssoicccooallllceeicdcttee4dd, iinn PPaappspuuoaan--NNgieeaww-13GG(1uu6ii)nn,1ee4aa-d((FFieiiggnu-u1rr9eee-a999l)))...42 and spongia-13(16),14-diene 43 from a S. officinalis collected in. TThhee iiddeennttiifificcaattiioonn ooff 5599 wwaass aaccccoommpplliisshheedd bbyy ccoommppaarriissoonn wwiitthh lliitteerraattuurree ddaattaa,, aalltthhoouugghh ssoommee ccoommmmeennttss wweerreemmadade.eC. Compound 100 showed no anti viral activity but was cytotoxic to HeLa (human cervix epithelioid carcinoma-CC100 30 μg/mL), Hep-2 (human larynx epidermoid carcinoma-CC100 40 μg/mL), CHO (Cricetulus griseus Chinese hamster ovary cells ATCC CCL-61-CC100 30 μg/mL) and Bon-Fib (primary culture of bovine ear subcutaneous fibroblasts-CC100 40 μg/mL) cells
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