Three New Cytotoxic Sesterterpenes from a Marine Sponge Spongia sp.

Abstract

Three new sesterterpenes (1-3) were isolated from a marine sponge of the genus Spongia, and their structures were determined on the basis of spectroscopic analysis. The compounds 1-3 exhibited cytotoxicity against HeLa cells with IC(50) values of 19.5, 15.0, and 5.3 microg/mL, respectively.

Indole alkaloid from the Red Sea sponge Hyrtios erectus

“…The structural assignments of 8 were based on an accurate study of the 1D and 2D (COSY, HMQC, HMBC) NMR spectra. The 1 H and 13 C NMR spectral data of 8 were consistent with the data for 12-episcalarin 18,19 and suggested that 8 was a deacetyl derivative of 12-episcalarin and identical with the previously published 12-Odeacetyl-12-epi-scalarin which isolated from Spongia sp.…”

Scalarane Sesterterpenoids

“…Later, it has been found in the Tongan sponge Hyrtios erecta [28], in the sponge Spongia agaricina collected near Tarifa Island (Spain) [30], in a sponge Hyrtios sp. collected at American Samoa [32], in the sponges Hyrtios erecta collected at Setouchi (Japan) [75] and collected from Hainan Island in the South China Sea [76], in sponges of the genus Spongia collected at the Japan Sea [77,78] and collected at the South Sea of Korea [79], and in the nudibranch Chromodoris funerea collected at Kaibakku Lake, Palau [80]. 12-Epi-scalarin (85) 12-Epi-scalaradial, 5 PLA2 inhibition and antiinflammarory [25] 12-Epi-scalaradial, 5…”

“…Antimicrobial [29] 12-Deacetyl-12,18-diepi-scalaradial, 10 Antitubercular, antimicrobial and cytotoxic [31,32] 12-Deacetyl-12,18-diepi-scalaradial, 10 Antifeedant [34,35] 12-Deacetyl-18-epi-12-oxoscalaradial, 11 Antimicrobial and cytotoxic [32] 12-Deacetyl-12-oxoscalaradial, 12 Ichthyotoxic [19] and antitubercular [31] 12-Deacetyl-12-oxoscalaradial, 12 Antimicrobial and cytotoxic [32] Mooloolabenes A (13), B (14) and C (15) Cytotoxic [36] Compounds RCE-protease inhibition and antitumour [68] epidermoid carcinoma KB, IC 50 = 18.5 μg/mL) [77], as well as neurotrophic activity in pheochromocytoma (PC-12) cells at the concentration of 50 μg/mL [78]. Compound 85 also showed inhibition of farnesoid Xactivated receptor (FXR) transactivation, which is related to potential drugs for hypercholesterolemia in humans, with IC 50 value of 60.4 μM [79].…”

“…12-O-Deacetyl-12-epi-scalarin (87) has been isolated from sponges of the genus Spongia collected at the Japan Sea [77,78] and collected at the South Sea of Korea [79], and sponges Hyrtios erecta collected at the Red Sea (Egypt) [82], and collected near Kavieng, Papua New Guinea [83]. 12-O-Deacetyl-12-epi-scalarin (87) 25-Dehydroxy-scalarin (89) has been found in the sponge Cacospongia scalaris collected at the Southern Coast of Spain [14], Meanwhile its epimer at C-12, 25dehydroxy-12-epi-scalarin (90), was isolated from the Pacific nudibranch Glossodoris dalli extract, after acetylation [47], and also from the sponges Hyrtios erecta collected at the South China Sea [76] and Brachiaster sp.…”

Anti-angiogenic activity of sesterterpenes; natural product inhibitors of FGF-2-induced angiogenesis

“…Compound 1 is a new addition to the Introduction Sesterterpenes are a large and diverse group of naturally occurring polyisoprene compounds found in plants, marine organisms and vertebrates [5]. Members of the family have moderate antibacterial activity against Mycobacterium tuberculosis strain H(37)Rv [28,29], anti-tumour activity and inhibit DNA replication [3] are cytotoxic against tumour cell lines [25] and have potent antiplasmodial properties [10].…”