Antifouling Diterpenoids from the Sponge Dendrilla antarctica.

Two nor-diterpenes, 9,11-dihydrogracilin A (1) and the previously unreported 9,11-dihydrogracillinone A (2), were isolated from the sponge Dendrilla antarctica. The sponge was collected by trawling at a depth of 49 m, from the research vessel Puerto Deseado, near the coast of Tierra del Fuego, farther north than the reported habitat for this species. Since these compounds were particularly abundant and the sponge was free from epibionts, both 1 and 2 were included in soluble-matrix paints and tested for antifouling activity in the ocean. The results obtained from these experiments clearly indicated a potent antifouling activity for both compounds against a variety of colonizing organisms, and established a probable role as natural antifoulants for these abundant secondary metabolites and other structurally related compounds previously isolated from Dendrilla spp.

Isolation and Antimacrofouling Activity of Indole and Furoquinoline Alkaloids from 'Guatambú' Trees (Aspidosperma australe and Balfourodendron riedelianum).

In this work, the antifouling activity of five alkaloids, isolated from trees of the Atlantic rainforest, was studied. The tested alkaloids were olivacine (1), uleine (2) and N-methyltetrahydroellipticine (3) from Aspidosperma australe ('yellow guatambú') and the furoquinoline alkaloids kokusaginine (4) and flindersiamine (5) from Balfourodendron riedelianum ('white guatambú'). All these compounds can be isolated from their natural sources in high yields in a sustainable way. The five compounds were subjected to laboratory tests (attachment test of the mussel Mytilus edulis platensis) and field trials, by incorporation into soluble matrix paints, and 45 days of exposure of the painted panels in the sea. The results show that compound 3 is a very potent antifoulant, and that compounds 4 and 5 are also very active, while compounds 1 and 2 did not show any significant antifouling activity. These results open the way for the development of environmentally friendly antifouling agents, based on abundant and easy-to-purify compounds that can be obtained in a sustainable way.