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Acetogenin

Group of chemical compounds

Acetogenin

Group of chemical compounds

Chemical structure of annonacin

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:

  • Annonacin
  • Annonins
  • Bullatacin
  • Uvaricin

Structure

Acetogenin core unit (mono-THF)
Acetogenin terminal lactone ring core unit (unsaturated)

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. These THF rings are located along the hydrocarbon chain, along with a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) and/or double bonds.

CompoundR1R2R3R4R54-deoxyannoreticuinAnnonacinAnnopentocin ADispalinDonnaienin CGoniotetracinMuricoreacinTonkinin AUvaribonone
OHOHHHH
OHOHHOHH
OHHHOHH
OAcOHHOHH
OHOHHOAcOH
OHOHHOHH
OHHHOHH
OHOHOHH
OHOAcOHH

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 (Asimina triloba) or the soursop (Annona muricata) remain under laboratory studies.

Mechanism of action

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

References

References

  1. (2008). "Recent Progress on the Total Synthesis of Acetogenins from Annonaceae". Beilstein Journal of Organic Chemistry.
  2. (2005). "Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action". Natural Product Reports.
  3. (2016). "Acetogenins from Annonaceae".
  4. (1999). "Annonaceous Acetogenins: Recent Progress". Journal of Natural Products.
  5. Ana V. Coria-Téllez. (2018). "Annona muricata: A comprehensive review on its traditional medicinal uses, phytochemicals, pharmacological activities, mechanisms of action and toxicity". Arabian Journal of Chemistry.
  6. (2011). "Annonaceae fruits and parkinsonism risk: Metabolisation study of annonacin, a model neurotoxin; evaluation of human exposure". Toxicology Letters.
  7. (2011). "Nuts and Seeds in Health and Disease Prevention". Academic Press.
  8. Robert A. Levine. (2015). "Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS". J. Agric. Food Chem..
  9. (2012). "Annonacin in ''Asimina triloba'' fruit: Implication for neurotoxicity". Neurotoxicology.
  10. (2008). "Paw paw and cancer: annonaceous acetogenins from discovery to commercial products.". Journal of Natural Products.
  11. (1 July 1994). "Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I).". Biochemical Journal.
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fatty-alcohols polyketides nadh-dehydrogenase-inhibitors plant-toxins
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