Abstract
Brown algae of the Family Dictyotaceae produce an array of structurally diverse terpenoids, whose biomedical potential in the anti-inflammatory area has been scarcely explored. Herein, the chemical study of the alga Rugulopteryx okamurae has led to the isolation of ten new diterpenoids: rugukadiol A (1), rugukamurals A–C (2–4), and ruguloptones A–F (6–10). The structures of the new compounds were established by spectroscopic means. Compound 1 exhibits an unprecedented diterpenoid skeleton featuring a bridged tricyclic undecane system. Compounds 2–10 belong to the secospatane class of diterpenoids and differ by the oxygenated functions that they contain. In anti-inflammatory assays, the new diterpenoid 1 and the secospatanes 5 and 10 significantly inhibited the production of the inflammatory mediator NO in LPS-stimulated microglial cells Bv.2 and macrophage cells RAW 264.7. Moreover, compounds 1 and 5 were found to strongly inhibit the expression of Nos2 and the pro-inflammatory cytokine Il1b in both immune cell lines.
Highlights
Algae of the Family Dictyotaceae are a prolific source of natural products, which account for almost 40% of the metabolites isolated from brown algae [1]
As a part of our research project aimed to study new anti-inflammatory compounds from algae, examined specimens of the to brown okamuraecompounds (DicAs a we parthave of our research project aimed studyalga newRugulopteryx anti-inflammatory tyotaceae) collected in the okamurae, first known as Dilophus okamurae from algae, we have examined specimens of the brown alga Rugulopteryx okamurae
Our results have shown that R. okamurae contains an array of compounds, some which could be of interest for pharmacological purposes in the anti-inflammatory area
Summary
Algae of the Family Dictyotaceae are a prolific source of natural products, which account for almost 40% of the metabolites isolated from brown algae [1]. Most of the isolated compounds are terpenoids, including sesquiterpenoids, diterpenoids, and meroterpenoids [1,2,3,4]. Species of the genera Dictyota, Canistrocarpus, Stoechospermum, Spatoglosum and Rugulopteryx, are characterized by producing a wide series of cyclic diterpenoids. These metabolites display a variety of carbon skeletons, which differ significantly among genera and may be useful chemotaxonomic markers [2,3,4]. From the biomedical point of view, properties such as antimicrobial [5,6,7] and cytotoxic [8,9,10] activities of some diterpenoids were already described during the first studies of this family of algae, and more recently antiviral [11,12,13], antileishmaniosis [14], antithrombotic [15], and further antibacterial [16] and anticancer activities [16,17] have been reported
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