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Structure and in vitro antitumor activity evaluation of brominated diterpenes from the red alga Sphaerococcus coronopifolius
Authors:Vangelis Smyrniotopoulos  Constantinos Vagias  Céline Bruyère  Delphine Lamoral-Theys  Robert Kiss  Vassilios Roussis
Affiliation:1. Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece;2. Université Libre de Bruxelles, Laboratoire de Toxicologie, Toxicologie et Chimie Physique Appliquée, Institut de Pharmacie, Boulevard du Triomphe, 1050 Bruxelles, Belgium;3. Université Libre de Bruxelles, Laboratoire de Chimie Analytique, Toxicologie et Chimie Physique Appliquée, Institut de Pharmacie, Boulevard du Triomphe, 1050 Bruxelles, Belgium
Abstract:
A novel bromoditerpene methyl ketone (1), two new bromoditerpene alcohols featuring a neodolastane (2), and a bromocorodienol skeleton (3), along with 13 previously reported metabolites (416) were isolated from the organic extract of Sphaerococcus coronopifolius collected from the rocky coasts of Corfu island in the Ionian Sea. The structures of the new natural products, as well as their relative stereochemistry, were elaborated on the basis of extensive spectral analysis, including 2D NMR experiments. The absolute stereochemistry of metabolite 3 was determined using the modified Mosher’s method. The isolated metabolites were evaluated for their antitumoral activity against four human apoptosis-resistant (U373, A549, SKMEL-28, OE21) and two human apoptosis-sensitive (PC-3, LoVo) cancer cell lines with IC50 in vitro growth inhibitory concentrations in the range 3–100 μM.
Keywords:
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