Pinnatifidenyne-derived ethynyl oxirane acetogenins from laurencia viridis

Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C acetogenin medium-ring ethers. Here, we described the isolation of three new C acetogenins (3–5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compou...

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Bibliographic Details
Authors: Morales-Amador, Adrián, de Vera, Caterina R., Márquez-Fernández, Olivia, Hernández Daranas, Antonio, Padrón, José M., Fernández, José J., Souto, María L., Norte, Manuel
Format: article
Status:Published version
Publication Date:2018
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/181574
Online Access:http://hdl.handle.net/10261/181574
Access Level:Open access
Keyword:C15 acetogenins
Marine natural product
Laurencia
DFT calculations
Antiproliferative activity
Ethynyl oxiranes
Pinnatifidenyne
Description
Summary:Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C acetogenin medium-ring ethers. Here, we described the isolation of three new C 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.