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

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Summary

Introduction

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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