Three New Scalarane Sesterterpenoids from the Okinawan Sponge Hyrtios erectus

Abstract

Three new scalarane sesterterpenoids-hyrtiolide (1), 16-hydroxyscalarolide (2), and 12-deacetyl-Delta(17)-hyrtial (3), were isolated from Okinawan sponge Hyrtios erectus, along with scalarolide (4) and 12-deacetylhyrtial (5). The structures of new compounds 1-3 were determined by spectroscopic analysis and chemical conversions. Compounds 3 and 5 showed antiproliferative activity toward KB cells.

Indole alkaloid from the Red Sea sponge Hyrtios erectus

“…While the MeOH-soluble residue was subjected to vacuum-liquid chromatography eluting with gradient CH 2 Cl 2 -MeOH followed by silica gel column chromatography and semipreparative HPLC to afford five compounds (1)(2)(3)(4)(5) (Figure 2), showed correlations which identified an indole-3-carbaldehyde structure. The NMR data were identical to those reported in literature 14 , but this is the first isolation of 2 from genus Hyrtios.…”

“…The secondary metabolites from the genus Hyrtios particularly Hertios erectus (synonym H. erecta) have been investigated extensively [1][2][3][4][5] . Previous chemical investigations of different Hyrtios sp.…”

Scalarane Sesterterpenoids

“…Both compounds showed antimicrobial activity using the standard disk assay against Staphylococcus aureus (25 μg/disk) and Bacillus subtilis (50 μg/disk) [29]. 12-Deacetylhyrtial (20) has also been isolated from the Okinawan sponge Hyrtios erectus (also called H. erecta) along with its 17 isomer (12-deacetyl-17 -hyrtial, 22) and both compounds showed cytotoxic activity against KB cells with IC 50 values of 10.0 and 2.82 μg/mL, respectively [38]. Norscalarals A-C (23)(24)(25) were isolated from the sponge Cacospongia scalaris collected at Tarifa Island (Spain).…”

Bioactive Compounds from the Red Sea Marine Sponge Hyrtios Species

“…Prominent reported classes from this genus include sesterterpenes [2,3,4,5,6], sesquiterpenes [7,8,9], macrolides [10,11], indole and β-carboline alkaloids [12,13,14,15,16]. Indole derivatives possess different biological activities including anticancer, antibiotic, anti-inflammatory and antioxidant activities [17,18].…”