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Acetogenins are a class of polyketide natural products found in plants of the family Annonaceae. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including hydroxyls, ketones, epoxides, tetrahydrofurans and tetrahydropyrans. They are often terminated with a lactone or butenolide.[1] Over 400 members of this family of compounds have been isolated from 51 different species of plants.[2] Many acetogenins are characterized by neurotoxicity.[3]
Examples include:
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Structurally, acetogenins are a series of C-35/C-37 compounds usually characterized by a long aliphatic chain bearing a terminal methyl-substituted α,β-unsaturated γ-lactone ring, as well as one to three tetrahydrofuran (THF) rings.[4] These THF rings are located along the hydrocarbon chain, along with a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) and/or double bonds.[4]
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Acetogenins have been investigated for their biological properties, but are a concern due to neurotoxicity.[5][6][7][8][9] Purified acetogenins and crude extracts of the common North American pawpaw (Asimina triloba) or the soursop (Annona muricata) remain under laboratory studies.[10]
Acetogenins inhibit NADH dehydrogenase, a key enzyme in energy metabolism.[11]
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