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Potent Cytotoxic Analogs of Amphidinolides from the Atlantic Octocoral Stragulum bicolor

1
Institute of Biomolecular Chemistry, National Research Council (CNR), 80078 Pozzuoli, Naples, Italy
2
Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza 60020-181, CE, Brazil
3
Stazione Zoologica Anton Dohrn, Villa Comunale, 80121 Napoli, Italy
4
Departamento de Farmacologia, Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo 11030-400, SP, Brazil
*
Authors to whom correspondence should be addressed.
These authors have equally contributed to this work.
Mar. Drugs 2019, 17(1), 58; https://doi.org/10.3390/md17010058
Received: 7 December 2018 / Revised: 9 January 2019 / Accepted: 12 January 2019 / Published: 16 January 2019
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Abstract

Amphidinolides are cytotoxic macrolides produced by symbiotic unicellular microalgae of the genus Amphidinium. Here we describe the identification of four related molecules belonging to this macrolide family isolated from the invertebrate Stragulum bicolor. The new molecules, named amphidinolide PX1-PX3 and stragulin A (14), show an unprecedented carbon skeleton whose complete stereochemistry has been determined by spectroscopic and computational methods. Differences in the structures of these molecules modulate their biological activity in a panel of tumor cell lines, but the opened derivative stragulin (4) shows a very potent and specific cytotoxic activity (IC50 0.18 µM) against the aggressive human melanoma cell A2058. View Full-Text
Keywords: amphidinolides; Stragulum bicolor; cytotoxic macrolides; stereochemistry amphidinolides; Stragulum bicolor; cytotoxic macrolides; stereochemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Nuzzo, G.; Gomes, B.A.; Gallo, C.; Amodeo, P.; Sansone, C.; Pessoa, O.D.L.; Manzo, E.; Vitale, R.M.; Ianora, A.; Santos, E.A.; Costa-Lotufo, L.V.; Fontana, A. Potent Cytotoxic Analogs of Amphidinolides from the Atlantic Octocoral Stragulum bicolor. Mar. Drugs 2019, 17, 58.

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