Coumarins from the Herb Cnidium monnieri and Chemically Modified Derivatives as Antifoulants against Balanus albicostatus and Bugula neritina Larvae

Abstract

In the search for new environmental friendly antifouling (AF) agents, four coumarins were isolated from the herbal plant Cnidium monnieri, known as osthole (1), imperatorin (2), isopimpinellin (3) and auraptenol (4). Furthermore, five coumarin derivatives, namely 8-epoxypentylcoumarin (5), meranzin hydrate (6), 2′-deoxymetranzin hydrate (7), 8-methylbutenalcoumarin (8), and micromarin-F (9) were synthesized from osthole. Compounds 1, 2, 4, 7 showed high inhibitory activities against larval settlement of Balanus albicostatus with EC50 values of 4.64, 3.39, 3.38, 4.67 μg mL−1. Compound 8 could significantly inhibit larval settlement of Bugula neritina with an EC50 value of 3.87 μg mL−1. The impact of functional groups on anti-larval settlement activities suggested that the groups on C-5′ and C-2′/C-3′ of isoamylene chian could affect the AF activities.

Antifouling activity of green-synthesized 7-hydroxy-4-methylcoumarin

“…As it has been indicated, there are few reports about the antifouling activity of coumarins, and in all cases the tests conducted were only at laboratory scale (Iyapparaj et al, 2012;Kim et al, 2013;Wang et al, 2013). In this sense, it was found that methanolic extract containing coumarins obtained from marine macroalgae, was able to inhibit completely the byssal thread production and attachment of brown mussel Perna indica (Iyapparaj et al, 2012).…”

“…neritina and the hard fouler Balanus albicostatus (Wang et al, 2013). Conversely, hard fouling species such as Balanus amphitrite have not been recruited in our field trials.…”

“…Little information is available on the activity of coumarins on fouling organisms referred only to laboratory tests (Iyapparaj et al, 2012;Kim et al, 2013;Wang et al, 2013). There are some investigations concerning to the use of coumarin in bioactive coatings in which it has been determined that coumarin moiety play a very important role as antimicrobial agent (Jaiswal et al, 2013;Patel et al, 2008Patel et al, , 2011Srivastava et al, 2012).…”

Protección antiincrustante de estructuras sumergidas mediante recubrimientos formulados con 7-hidroxi-4-metilcumarina

“…Existen muy pocos reportes [20][21] acerca de la actividad antifouling de las cumarinas y, en todos los casos, los tests fueron llevados a cabo solamente a escala de laboratorio. Se ha reportado que los extractos metanólicos conteniendo cumarinas obtenidas de macroalgas fueron capaces de inhibir completamente la producción de hilos del biso en el mejillón Perna indica [19].…”

“…y Hydroides elegans) y ascidias (Ciona intestinalis), manteniéndose el poder antiincrustante durante los 90 días de experimentación (p < 0.05) (Figuras 2 y 3). Los resultados de estos experimentos concuerdan con los hallados para cumarinas aisladas del árbol de canela que evitaron el asentamiento de algas [20] y de cumarinas de hierbas que mostraron efecto antiincrustante sobre briozoos y cirripedios [21]. Las propiedades de las cumarinas fueron intensamente estudiadas en relación con su estructura molecular.…”