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.
Highlights
Medium-ring haloethers of Laurencia, a significant subset of biologically active marine natural products [1,2], continue to challenge innovative efforts as attractive targets for the synthesis of stereochemically rich medium-sized oxacyclic compounds [3,4] or to explore biogenetic hypothesis [5,6].Z-Pinnatifidenyne and E-pinnatifidenyne (1–2) are representative and were reported in 1982 after isolation from the red algae Laurencia pinnatifida collected at Canary Islands [7]
Their structures were established by espectroscopic methods, X-ray diffraction analysis and chemical correlations, in 1991, the absolute configurations were reassigned based on a later X-ray analysis [8]
As part of our continuing interest on the chemistry of the genus Laurencia [11,12,13,14] and during the course of our anticancer drug discovery program, we report the isolation of three new C15 acetogenins and one truncated derivative from Laurencia viridis (Figure 1)
Summary
Medium-ring haloethers of Laurencia, a significant subset of biologically active marine natural products [1,2], continue to challenge innovative efforts as attractive targets for the synthesis of stereochemically rich medium-sized oxacyclic compounds [3,4] or to explore biogenetic hypothesis [5,6]. Z-Pinnatifidenyne and E-pinnatifidenyne (1–2) are representative and were reported in 1982 after isolation from the red algae Laurencia pinnatifida collected at Canary Islands [7]. Their structures were established by espectroscopic methods, X-ray diffraction analysis and chemical correlations, in 1991, the absolute configurations were reassigned based on a later X-ray analysis [8]. A detailed study of NMR chemical are variations on the pinnatifidenyne structure with biogenetic relevance. A detailed shifts calculations wasDFT alsocalculations undertaken and their was antiproliferative activity against studybyofDFT chemical analysis shifts by analysis undertaken and their human cancer cell lines.
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