Abstract
Meroterpenes are compounds of mixed biogenesis, isolated from plants, microorganisms and marine invertebrates. We have previously isolated and determined the structure for a series of meroterpenes extracted from the ascidian Aplidium aff. densum. Here, we demonstrate the chemical synthesis of three of them and their derivatives, and evaluate their biological activity on two bacterial strains, on sea urchin eggs, and on cancerous and healthy human cells.
Highlights
Meroterpenes are compounds of mixed biosynthesis, mostly quinone or hydroquinones bonded with a terpenoid portion ranging from one to nine isoprene units
Considering the severe cell cycle disruption produced by methoxyconidiol treatment in sea urchin eggs, we directly evaluated the cytotoxicity of these new compounds on a panel of murine and human cells, both healthy and cancerous
As previously described by Cruz-Almanza et al, the natural meroterpene 3a and the methoxy derivatives 3b–5b were synthesized starting from compounds 2a and 2b, respectively, using acidic conditions (Scheme 1) [13]
Summary
Meroterpenes are compounds of mixed biosynthesis, mostly quinone or hydroquinones bonded with a terpenoid portion ranging from one to nine isoprene units. One of these compounds, methoxyconidiol, when tested on sea urchin embryos during cell division, disturbs mitotic spindle assembly leading to a cell cycle arrest during metaphase/anaphase transition [12]. Methoxyconidiol, when tested on sea urchin embryos during cell division, disturbs mitotic spindle assembly leading to a cell cycle arrest during metaphase/anaphase transition [12] These promising results led us to synthesize compound 5a, and the natural analogs 3a and 4a, as well as the methoxylated derivatives 3b–5b, in order to determine the role of the phenol functions. Considering the severe cell cycle disruption produced by methoxyconidiol treatment in sea urchin eggs, we directly evaluated the cytotoxicity of these new compounds on a panel of murine and human cells, both healthy and cancerous
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