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Open AccessArticle

Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis

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Instituto 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
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Departamento de Química Orgánica, Universidad de La Laguna (ULL), Avenida Astrofísico Francisco Sánchez s/n, 38206 Tenerife, Spain
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Facultad de Ciencias Biológicas-Universidad Veracruzana, Circuito Gonzalo Aguirre Beltrán s/n, Zona Universitaria C.P., Xalapa 91090, Veracruz, Mexico
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Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, Avenida Astrofísico Francisco Sánchez 2, 38206 Tenerife, Spain
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Authors to whom correspondence should be addressed.
Mar. Drugs 2018, 16(1), 5; https://doi.org/10.3390/md16010005
Received: 2 October 2017 / Revised: 5 December 2017 / Accepted: 13 December 2017 / Published: 29 December 2017
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 (35), 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 (34). 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. View Full-Text
Keywords: pinnatifidenyne; ethynyl oxiranes; C15 acetogenins; marine natural product; Laurencia; DFT calculations; antiproliferative activity pinnatifidenyne; ethynyl oxiranes; C15 acetogenins; marine natural product; Laurencia; DFT calculations; antiproliferative activity
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Morales-Amador, A.; De Vera, C.R.; Márquez-Fernández, O.; Hernández Daranas, A.; Padrón, J.M.; Fernández, J.J.; Souto, M.L.; Norte, M. Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis. Mar. Drugs 2018, 16, 5.

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