Acetogenin Explained

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

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
Compound R1 R2 R3 R4 R5
4-deoxyannoreticuin OH OH H H H
AnnonacinOH OH H OH H
Annopentocin AOH H H OH H
DispalinOAc OH H OH H
Donnaienin COH OH H OAc OH
GoniotetracinOH OH H OH H
MuricoreacinOH H H OH H
Tonkinin AOH OH O H H
UvaribononeOH OAc O H H

Research

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]

Mechanism of action

Acetogenins inhibit NADH dehydrogenase, a key enzyme in energy metabolism.[11]

Notes and References

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

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