Volume 7 Issue 4
Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis
Adrián Morales-Amador, Caterina R. De Vera, Olivia Márquez-Fernández, Antonio Hernández Daranas, José M. Padrón, José J. Fernández, María L. Souto and Manuel Norte
1Instituto Universitario de Bio-Orgánica Antonio González (IUBO AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna (ULL), Avenida Astrofísico Francisco Sánchez 2, 38206 Tenerife, Spain
2Departamento de Química Orgánica, Universidad de La Laguna (ULL), Avenida Astrofísico Francisco Sánchez s/n, 38206 Tenerife, Spain
3Facultad de Ciencias Biológicas-Universidad Veracruzana, Circuito Gonzalo Aguirre Beltrán s/n, Zona Universitaria C.P., Xalapa 91090, Veracruz, Mexico
4Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, Avenida Astrofísico Francisco Sánchez 2, 38206 Tenerife, Spain
*Authors to whom correspondence should be addressed.
Abstract
Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C15 acetogenin medium-ring ethers. Here, we described the isolation of three new C15 acetogenins (3–5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives (3–4). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J-based configuration analysis and DFT (Density Functional Theory) calculations. Their antiproliferative activity against six human solid tumor cell lines was evaluated.
Keywords:pinnatifidenyne; ethynyl oxiranes; C15 acetogenins; marine natural product; Laurencia; DFT calculations; antiproliferative activity