Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis

Abstract

This paper reports the antifouling properties of the dichloromethane crude extract (DC) and 3 pure compounds isolated from the Brazilian brown seaweed Canistrocarpus cervicornis against establishment of the mussel Perna perna. DC extract showed a strong inhibition activity against byssal threads. Two natural dolastanes and one seco-dolastane diterpene, namely (4R, 9S, 14S)-4α-acetoxy-9β,14α-dihydroxydolast-1(15),7-diene (1), (4R,7R,14S)-4α,7α-diacetoxy-14-hydroxydolast-1(15),8-diene (2) and isolinearol (3), were isolated from DC extract. Dolastane (1) inhibited 60% of byssal fixation, while compound 2 and the seco-dolastane (3) strongly inhibited (82%) the establishment of P. perna. This is the first report of this type of chemical skeleton in three powerful compounds that could be further explored for the development of antifouling technology.

Anti-snake venom effect of secodolastane diterpenes isolated from Brazilian marine brown alga Canistrocarpus cervicornis against Lachesis muta venom

“…These molecules are the products of secondary metabolism and display pharmacological properties (Mayer et al, 2007;Cirne-Santos et al, 2008;Abrantes et al, 2010) as well as ecological functions (Bianco et al, 2009). A previous study demonstrated that L. muta venom displayed phospholipase A 2 (indirect hemolytic activity), hemorrhagic, clotting and proteolytic activities (Fuly et al, 1993).…”

“…The brown seaweed Canistrocarpus cervicornis (Kützing) De Paula & De Clerck (formely Dictyota cervicornis Kützing) possesses a biosynthetic pathway that produces dolastane and seco-dolastane diterpenes, encompassing a total of more than 25 compounds (Teixeira et al, 1986;de Oliveira et al, 2008). Not surprisingly, some of these diterpenes are biologicallyactive molecules (Bianco et al, 2009;Moura et al, 2010).…”

Extracts of seaweeds as potential inhibitors of quorum sensing and bacterial growth

“…It is known that this alga produces mainly dolastane and secodolastane diterpenes, which exhibit antiviral (Vallim et al 2010), antiophidian (Santos et al 2011), and antileishmanial (Moura et al 2011) activities. Furthermore, C. cervicornis produces diterpenes capable of inhibiting mussel byssal formation (Bianco et al 2009). In our study, Padina sp.…”

Induction of Antifouling Diterpene Production byStreptomyces cinnabarinusPK209 in Co-Culture with Marine-DerivedAlteromonassp. KNS-16

“…Dolabelane, isolated from the Brazilian brown alga Canistrocarpus cervicornis, inhibits mussel byssus formation, whereas pachydictiane, from the brown alga Dictyota sp., inhibits the growth of biofilm-forming bacteria. 22,23) Briarane diterpenes discovered in the South China Sea gorgonian Junceella juncea have antifouling activity against barnacle cyprids. 24,25) The literature indicates that diterpenes have promising antifouling activity.…”