Bioactive Compounds from the Red Sea Marine Sponge Hyrtios Species

Abstract

In continuation of our search for drug leads from Red Sea sponges we have investigated the ethyl acetate fraction of the organic extract of the Red Sea sponge Hyrtios species. Bioassay-directed fractionation of the active fraction resulted into the identification of three new alkaloids, hyrtioerectines D–F (1–3). Hyrtioerectines D–F belong to the rare marine alkaloids in which the indole and β-carboline fragments of the molecule are linked through C-3/C-3 of both moieties. The structures of the isolated compounds were established based on different spectroscopic data including UV, IR, 1D and 2D NMR (COSY, HSQC, and HMBC) and high-resolution mass spectral studies. The antimicrobial activity against several pathogens and the free radical scavenging activity of the compounds using DPPH reagent were evaluated. In addition, the growth inhibitory activity of the compounds against three cancer cell lines was also evaluated. Hyrtioerectines D–F (1–3) displayed variable antimicrobial, free radical scavenging and cancer growth inhibition activities. Generally, compounds 1 and 3 were more active than compound 2.

Composition and Predictive Functional Analysis of Bacterial Communities in Seawater, Sediment and Sponges in the Spermonde Archipelago, Indonesia

“…Tyrosine is an amino acid that occurs in proteins belonging to signal transduction processes, plays a role in photosynthesis and is a precursor to alkaloids and phenols [89,90]. Enrichment in the tyrosine and phenylalanine metabolic pathways and the importance of these pathways for the biosynthesis of alkaloids and phenols are in line with the numerous bioactive compounds that have been isolated from X. testudinaria and H. erectus [91][92][93][94][95]. Numerous bioactive compounds have also been isolated from Stylissa species including dimeric alkaloids (e.g., dibromophakellin and sceptrin), brominated pyrrole alkaloids and other brominated alkaloids.…”

Marine Indole Alkaloids

“…1-Carboxy-6-hydroxy-3,4-dihydro-β-carboline ( 774 ) [ 330 ] and hyrtioerectines D–F ( 775 – 777 ) [ 331 ] have been isolated from the marine sponge Hyrtios sp. ( Figure 143 ).…”

“…Hyrtioerectines D–F ( 775 – 777 ) displayed antimicrobial activity against C. albicans and Staphylococcus aureus , as well as free radical scavenging and anticancer (A549, HT-29, MDA-MB-231) activities. Diphenolic compounds ( 775 ) and ( 777 ) showed higher activities than ( 776 ) [ 331 ]. Hyrtiocarboline ( 778 ) was obtained from the marine sponge Hyrtios reticulatus (Papua New Guinea) and exhibited selective antiproliferative activity towards the tumor cell lines H522-T1, MDA-MB-435 and U937 [ 332 ].…”

Marine Spongia collagens: Protein characterization and evaluation of hydrogel films

“…Marine sponges synthesize a variety of specialized bioactive compounds, some of which are being investigated for nutraceutical or pharmaceutical applications as reported elsewhere . Raw sponges or collagens extracted from sponge skeletons were used to develop tissue engineering scaffolds and dermal drug delivery systems .…”

“…15,17 Marine sponges synthesize a variety of specialized bioactive compounds, some of which are being investigated for nutraceutical or pharmaceutical applications as reported elsewhere. [18][19][20][21] Raw sponges or collagens extracted from sponge skeletons were used to develop tissue engineering scaffolds and dermal drug delivery systems. 14,15,[22][23][24] In addition, sea sponges are used worldwide for their numerous industrial, medical, household, and cultural uses.…”