Article · Wikipedia archive · Last revised Jul 5, 2026

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.

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Wikipedia ↗
Chemical structure of annonacin source ↗

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:

Structure

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

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

Examples of R-groups for selected acetogenins 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

Research

Acetogenins have been investigated for their biological properties, but are a concern due to neurotoxicity.56789 Purified acetogenins and crude extracts of the common North American pawpaw (Asimina triloba) or the soursop (Annona muricata) remain under laboratory studies.10

Mechanism of action

Acetogenins inhibit NADH dehydrogenase, a key enzyme in energy metabolism, disrupting mitochondrial function cumulatively.1112

References

References

  1. Li, N.; Shi, Z.; Tang, Y.; Chen, J.; Li, X. (2008). "Recent Progress on the Total Synthesis of Acetogenins from Annonaceae" (PDF). Beilstein Journal of Organic Chemistry. 4 (48): 1–62. doi:10.3762/bjoc.4.48. PMC 2633664. PMID 19190742.
  2. Bermejo, A.; Figadère, B.; Zafra-Polo, M.-C.; Barrachina, I.; Estornell, E.; Cortes, D. (2005). "Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action". Natural Product Reports. 22 (2): 269–303. doi:10.1039/B500186M. PMID 15806200. Erratum: "Back Matter". Natural Product Reports. 22 (3): 426. 2005. doi:10.1039/B503508M.
  3. Liaw, Chih-Chuang; Liou, Jing-Ru; Wu, Tung-Ying; Chang, Fang-Rong; Wu, Yang-Chang (2016). Acetogenins from Annonaceae. Progress in the Chemistry of Organic Natural Products. Vol. 101. pp. 113–230. doi:10.1007/978-3-319-22692-7_2. ISBN 978-3-319-22691-0. PMID 26659109.
  4. Alali, Feras Q; Liu, Xiao-Xi; McLaughlin, Jerry L (1999). "Annonaceous Acetogenins: Recent Progress". Journal of Natural Products. 62 (3): 504–40. Bibcode:1999JNAtP..62..504A. doi:10.1021/np980406d. PMID 10096871.
  5. Ana V. Coria-Téllez; Efigenia Montalvo-Gónzalez; Elhadi M. Yahia; Eva N. Obledo-Vázquez (2018). "Annona muricata: A comprehensive review on its traditional medicinal uses, phytochemicals, pharmacological activities, mechanisms of action and toxicity". Arabian Journal of Chemistry. 11 (5): 662–691. doi:10.1016/j.arabjc.2016.01.004.
  6. Le Ven, J.; Schmitz-Afonso, I.; Touboul, D.; Buisson, D.; Akagah, B.; Cresteil, T.; Lewin, G. (2011). "Annonaceae fruits and parkinsonism risk: Metabolisation study of annonacin, a model neurotoxin; evaluation of human exposure". Toxicology Letters. 205: S50–S51. doi:10.1016/j.toxlet.2011.05.197.
  7. Victor R. Preedy; Ronald Ross Watson; Vinood B. Patel, eds. (2011). Nuts and Seeds in Health and Disease Prevention. Academic Press. pp. 434–435.
  8. Robert A. Levine; Kristy M. Richards; Kevin Tran; Rensheng Luo; Andrew L. Thomas & Robert E. Smith (2015). "Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS". J. Agric. Food Chem. 63 (4): 1053–1056. Bibcode:2015JAFC...63.1053L. doi:10.1021/jf504500g. PMID 25594104.
  9. Potts, L. F.; Luzzio, F. A.; Smith, S. C.; Hetman, M; Champy, P; Litvan, I (2012). "Annonacin in Asimina triloba fruit: Implication for neurotoxicity". Neurotoxicology. 33 (1): 53–8. Bibcode:2012NeuTx..33...53P. doi:10.1016/j.neuro.2011.10.009. PMID 22130466.
  10. McLaughlin, J.L. (2008). "Paw paw and cancer: annonaceous acetogenins from discovery to commercial products". Journal of Natural Products. 71 (7): 1311–21. Bibcode:2008JNAtP..71.1311M. doi:10.1021/np800191t. PMID 18598079.
  11. Eposti, M (1 July 1994). "Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I)". Biochemical Journal. 301 (1): 161–167. doi:10.1042/bj3010161. PMC 1137156. PMID 8037664.
  12. de Langavant, LC (10 October 2022). "Annonaceae Consumption Worsens Disease Severity and Cognitive Deficits in Degenerative Parkinsonism". Movement Disorders. 37 (12): 2355–2366. doi:10.1002/mds.29222.
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