Abstract
As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1 [(-)-(5E,7Z)-348-trichloro-7-dichloromethyl-3-methyl-157-octatriene] in addition to three known compounds (2, 3 and 4) from the red alga Plocamium cartilagineum collected by hand from the eastern coast of South Africa. Compound 1 was found to be active as a cytotoxic agent in human lung cancer (NCI-H460) and mouse neuro-2a cell lines (IC50 4 μg/mL). Two of these compounds (3 and 4) were found to have cytotoxic activity in other cell line assays, especially against human leukaemia and human colon cancers (IC50 1.3 μg/mL). None of these metabolites were active as sodium channel blockers or activators. All structures were determined by spectroscopic methods (UV, IR, LRMS, HRMS, 1D NMR and 2D NMR). 1D and 2D NOE experiments were carried out on these compounds to confirm the geometry of the double bonds.
Highlights
As a result of their predominant growth in temperate and tropical locations, red algae are among the most frequently investigated sources for marine natural products
Plocamium cartilagineum is a species of red algae
This species is characterized by its interesting secondary metabolites, being a rich source of diverse polyhalogenated monoterpenes, with a surprising degree of halogen incorporation (Young et al, 2013; Inés et al, 2004, Palma et al, 2004, Gao et al, 2001, Norton et al, 1977; Capon et al, 1984; Wright et al, 1990; Mynderse and Faulkner, 1975)
Summary
As a result of their predominant growth in temperate and tropical locations, red algae are among the most frequently investigated sources for marine natural products. Polyhalogenated monoterpenes vary for the given species depending on collection, location and season (Fuller et al, 1992) Research on this genus has yielded a number of halogenated metabolites that display considerable biological activities such as cytotoxic activity (Naylor et al, 1983; Ortega et al, 1997; Wessels et al, 2000; Vogel et al, 2014), anti-feedant activity (Argandona et al, 2002), anti-fungal activity, molluscicidal activity and insecticidal activity (Watanabe et al, 1989). These secondary metabolites can be categorized into two predominant skeletal types, the 2,6-dimethyloctanes and cyclohexanes (Mynderse and Faulkner, 1975; Crews 1977)
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