Acetogenin


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. Over 400 members of this family of compounds have been isolated from 51 different species of plants. Many acetogenins are characterized by neurotoxicity.
Examples include:

Structure

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 rings. These THF rings are located along the hydrocarbon chain, along with a number of oxygenated moieties and/or double bonds.
CompoundR1R2R3R4R5
4-deoxyannoreticuinOHOHHHH
AnnonacinOHOHHOHH
Annopentocin AOHHHOHH
DispalinOAcOHHOHH
Donnaienin COHOHHOAcOH
GoniotetracinOHOHHOHH
MuricoreacinOHHHOHH
Tonkinin AOHOHOHH
UvaribononeOHOAcOHH

Research

Acetogenins have been investigated for their biological properties, but are a concern due to neurotoxicity. Purified acetogenins and crude extracts of the common North American pawpaw or the soursop remain under laboratory studies.

Mechanism of action

Acetogenins inhibit NADH dehydrogenase, a key enzyme in energy metabolism.