Abstract
The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (2–5) as well as undescribed compounds of the same class, anverenes B–D (6–8). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy and negative chemical ionization mass spectrometry. Compounds 1–9 show moderate cytotoxicity against cervical cancer (HeLa) cells.
Highlights
Plocamium cartilagineum is a broadly distributed red alga that contributes to the structure of algal-dominated coastal benthic ecosystems of the Western Antarctic Peninsula [1]
Subtidal red algae currently lumped in the single species Plocamium cartilagineum have historically yielded a large and varied group of halogenated monoterpenes since chemical examination into its metabolome began several decades ago [6]
The results of our investigation indicate that certain chemotypes tend to produce acyclic polyhalogenated monoterpenes while others express primarily cyclic compounds, which may explain some of the variation seen in past inquiries
Summary
Plocamium cartilagineum is a broadly distributed red alga that contributes to the structure of algal-dominated coastal benthic ecosystems of the Western Antarctic Peninsula [1]. There is no currently accepted alternate species name, P. cartilagineum in Antarctica is known to be a distinct species from what is called P. cartilagineum in other parts of the world [2]. This rhodophyte is known to produce many different polyhalogenated monoterpenes, including anverene (1, Scheme 1), which has been shown to convey ecological relevance as a feeding deterrent toward sympatric macroalgal consumers [3,4]. Previous studies have shown that chemical diversity among phenotypes of this alga is high, with specific chemotypes (chemogroups [1]) displaying different halogenated terpenes with variable relative abundances.
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