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:
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]
Compound | R1 | R2 | R3 | R4 | R5 |
---|---|---|---|---|---|
4-deoxyannoreticuin | OH | OH | H | H | H |
Annonacin | OH | OH | H | OH | H |
Annopentocin A | OH | H | H | OH | H |
Dispalin | OAc | OH | H | OH | H |
Donnaienin C | OH | OH | H | OAc | OH |
Goniotetracin | OH | OH | H | OH | H |
Muricoreacin | OH | H | H | OH | H |
Tonkinin A | OH | OH | O | H | H |
Uvaribonone | OH | OAc | O | H | H |
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]
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:
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]
Compound | R1 | R2 | R3 | R4 | R5 |
---|---|---|---|---|---|
4-deoxyannoreticuin | OH | OH | H | H | H |
Annonacin | OH | OH | H | OH | H |
Annopentocin A | OH | H | H | OH | H |
Dispalin | OAc | OH | H | OH | H |
Donnaienin C | OH | OH | H | OAc | OH |
Goniotetracin | OH | OH | H | OH | H |
Muricoreacin | OH | H | H | OH | H |
Tonkinin A | OH | OH | O | H | H |
Uvaribonone | OH | OAc | O | H | H |
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]