Antiproliferative Scalarane-Based Metabolites from the Red Sea Sponge Hyrtios erectus

Abstract

Two new sesterterpenes analogs, namely, 12-acetoxy,16-epi-hyrtiolide (1) and 12β-acetoxy,16β-methoxy,20α-hydroxy-17-scalaren-19,20-olide (2), containing a scalarane-based framework along with seven previously reported scalarane-type sesterterpenes (3–9) have been isolated from the sponge Hyrtios erectus (order Dictyoceratida) collected from the Red Sea, Egypt. The structures of the isolated compounds were elucidated on the basis of their spectroscopic data and comparison with reported NMR data. Compounds 1–9 exhibited considerable antiproliferative activity against breast adenocarcinoma (MCF-7), colorectal carcinoma (HCT-116) and hepatocellular carcinoma cells (HepG2). Compounds 3, 5 and 9 were selected for subsequent investigations regarding their mechanism of cell death induction (differential apoptosis/necrosis assessment) and their influence on cell cycle distribution.

Marine Invertebrate Extracts Induce Colon Cancer Cell Death via ROS-Mediated DNA Oxidative Damage and Mitochondrial Impairment

“…Nevertheless, the semiquantitative analysis (as determined by the larger normalized area percentage) of the compounds present in the marine extracts utilized revealed that the observed antiproliferative effects might be associated with particular families of compounds (Tables 3-6). For instance, the main candidates to account for the antiproliferative effects of the CR extract might be diterpenes such as spongian-16-one [40], polyoxygenated marine steroids such as punicinol D [52], sesquiterpenes such as dendronephthol C [37], or sesterterpenes such as deoxoscalarin [38]. In the PS extract, furanocembranolide lopholide [56,64] seems to be the most abundant compound with a reported antiproliferative capacity in cancer cells.…”

Bioactive Natural Products of Marine Sponges from the Genus Hyrtios

“…Two new sesterterpene analogs, 12-acetoxy,16- epi -hyrtiolide ( 60 ) and 12β-acetoxy,16β-methoxy,20α-hydroxy-17-scalaren-19,20-olide ( 61 ), together with seven previously reported scalarane-type sesterterpenes, 23 , 25 , and 62 – 66 , were isolated from the sponge H. erectus collected from the Red Sea, Egypt ( Figure 16 ). The isolated compounds 25 and 60 – 66 showed considerable in vitro anticancer activity against breast adenocarcinoma (MCF-7), colorectal carcinoma (HCT-116) and hepatocellular carcinoma cells (HepG2), with IC 50 values of 0.7–57.5 µM [ 42 ].…”

“…Genus Hyrtios attracted scientists’ attention and sparked high synthetic efforts for the synthesis of the isolated compounds from its members [ 37 , 38 ]. Several compounds have been synthesized such as Salmahyrtisol A from Hyrtios erecta [ 39 , 40 ], Similan A from the Thai sponge Hyrtios gumininae [ 41 , 42 ], sesterstatin 1 from Hyrtios erecta [ 43 , 44 ], Spongistatins 1 (Altohyrtin A ) from Hyrtios erecta [ 45 , 46 ], (−)-Hyrtiosal and its C-16 epimer have been synthetized from sclareol [ 47 ] which was previously isolated from the sponge Hyrtios erectus [ 48 ].…”

LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

“…In the course of our ongoing efforts to isolate and identify drug leads from marine metabolites [22][23][24][25][26][27], we have investigated the extract of the Red Sea deep-sediment isolated fungus Penicillium chrysogenum strain S003.…”