Isolation of antifouling substances from the Palauan sponge Protophlitaspongia aga

Abstract

Fouling organisms cause serious problems by settling on ships’ hulls, and other marine infrastructures. Organotin compounds have been developed as effective antifoulants. However, environmental problems are associated with these compounds. It is necessary to find antifouling substances that exhibit a lower toxicity than those substances currently used. A new pyrimidine derivative, 3,4,5,6‐tetrahydro‐6‐hydroxymethyl‐3,6‐dimethyl‐4‐pyrimidinecarboxylic acid, (compound 1) and zooanemonin (compound 2) were isolated from the marine sponge Protophlitaspongia aga as antifouling substances against the barnacle Balanus amphitrite. We also found that α‐nicotinamide ribose (compound 3) inhibited germination and the attachment of Ulva spores.

Effects of water temperature and pH on growth and metabolite biosynthesis of coral reef sponges

“…Zooanemonin killed barnacles in a laboratory study at a concentration of 0.05 mg g −1 wet sponge (Hattori et al 2001); using wet-to-dry-weight conversions for sponges (Ricciardi & Bourget 1998) this corresponds to an estimated value of 0.3 mg g −1 sponge. In this study, final concentrations of zooanemonin in E. ferox varied significantly between temperatures, and were 1.9 and 1.5 mg g −1 sponge at 28 and 31°C, respectively.…”

“…Ecological roles are also suggested for several secondary metabolites isolated from these sponges. For example, zooanemonin and N-methyl-aerophobin 2 have antifouling properties (Hattori et al 2001, Diers et al 2004, fistularin 3 is likely a precursor molecule for hemifisturlarin 3, which prevents fouling (Diers et al 2004), while histamines deter fish predation (Lindel et al 2000). All 6 sponge species are commonly found on Caribbean coral reefs at shallow depths (< 20 m), including the north shore of Jamaica where this study occurred.…”

Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

“…So far, only three natural modified pyridine nucleosides have been discovered, namely, clitidine (3-carboxy-4-imino-l-(β-D-ribofuranosyl)-1,4-dihydropyridine) from the poisonous mushroom Clitocybe acromelalga, 17 1-α-D-ribofuranosyl-4-pyridone-3-carboxamide from the urine of normal human individuals and leukemic patients, 18 and α-nicotinamide riboside from the marine sponge Protophlitaspongia aga. 19 The occurrence of an oxidized nicotinamide adenine dinucleotide containing an α-riboside linkage in nature was first reported by Kaplan and co-workers. 20 A biological role for α-NAD + and α-NADP + , however, was not uncovered.…”

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

“…The storage of biologically active secondary metabolites by marine invertebrates is frequently related to their ecological success, in spite of their exposition to predation, infestation by microbial pathogens, overgrowth, fouling and competition for space and nutrients (reviewed in Amsler et al, 2001;Blunt et al, 2007;Faulkner et al, 2004;Lindquist, 2002;Paul, 1992;Pawlik, 1993;Stachowicz, 2001). Marine sponges, ascidians, soft-bodied cnidaria and bryozoans are representative groups of marine invertebrates which are chemically defended against predators (for selected examples, see Aceret et al, 2001;Becerro et al, 1998;Burns et al, 2003;Chanas et al, 1996;Epifanio et al, 1999a;Epifanio et al, 1999b;Kubanek et al, 2002;Lindel et al, 2000;Lindquist, 1996;Marin et al, 1998;McClintock and Baker, 1997;O'Neal and Pawlik, 2002;Pawlik et al, 1995;Pisut and Pawlik, 2002;Stachowicz and Lindquist, 1997;Van Alstyne et al, 1994;Vervoort et al, 1998;Waddell and Pawlik, 2000), fouling (Becerro et al, 1997;Bhosale et al, 2002;Hattori et al, 2001;Henrikson and Pawlik, 1995;Kelly et al, 2003;Wahl et al, 1994), larval settlement (reviewed in Davis et al, 1989;Fusetani, 1997;Martín and Uriz, 1993;Pawlik, 1992) and solar UV radiation (Bandaranayake et...…”