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[[File:Annonacin.png|thumb|right|Chemical structure of annonacin]]
[[File:Annonacin.png|thumb|right|Chemical structure of annonacin]]
'''Acetogenins''' are a class of [[polyketide]] [[natural product]]s found in plants of the family [[Annonaceae]]. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including [[hydroxyl]]s, [[ketone]]s, [[epoxide]]s, [[tetrahydrofuran]]s and [[tetrahydropyran]]s. They are often terminated with a [[lactone]] or [[butenolide]].<ref>{{cite journal | last1 = Li | first1 = N. | last2 = Shi | first2 = Z. | last3 = Tang | first3 = Y. | last4 = Chen | first4 = J. | last5 = Li | first5 = X. | title = Recent Progress on the Total Synthesis of Acetogenins from Annonaceae | journal = Beilstein Journal of Organic Chemistry | year = 2008 | volume = 4 | issue = 48 | pages = 1–62 | pmid = 19190742 | pmc = 2633664 | doi = 10.3762/bjoc.4.48 | url = http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-4-48.pdf }}</ref> Over 400 members of this family of compounds have been isolated from 51 different species of plants.<ref>{{cite journal | last1 = Bermejo | first1 = A. | last2 = Figadère | first2 = B. | last3 = Zafra-Polo | first3 = M.-C. | last4 = Barrachina | first4 = I. | last5 = Estornell | first5 = E. | last6 = Cortes | first6 = D. | title = Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action | journal = Natural Product Reports | year = 2005 | volume = 22 | issue = 2 | pages = 269–303 | pmid = 15806200 | doi = 10.1039/B500186M }} Erratum: {{ cite journal | title = Back Matter | journal = Natural Product Reports | year = 2005 | volume = 22 | issue = 3 | pages = 426 | doi = 10.1039/B503508M }}</ref>
'''Acetogenins''' are a class of [[polyketide]] [[natural product]]s found in plants of the family [[Annonaceae]]. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including [[hydroxyl]]s, [[ketone]]s, [[epoxide]]s, [[tetrahydrofuran]]s and [[tetrahydropyran]]s. They are often terminated with a [[lactone]] or [[butenolide]].<ref>{{cite journal | last1 = Li | first1 = N. | last2 = Shi | first2 = Z. | last3 = Tang | first3 = Y. | last4 = Chen | first4 = J. | last5 = Li | first5 = X. | title = Recent Progress on the Total Synthesis of Acetogenins from Annonaceae | journal = Beilstein Journal of Organic Chemistry | year = 2008 | volume = 4 | issue = 48 | pages = 1–62 | pmid = 19190742 | pmc = 2633664 | doi = 10.3762/bjoc.4.48 | url = http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-4-48.pdf }}</ref> Over 400 members of this family of compounds have been isolated from 51 different species of plants.<ref>{{cite journal | last1 = Bermejo | first1 = A. | last2 = Figadère | first2 = B. | last3 = Zafra-Polo | first3 = M.-C. | last4 = Barrachina | first4 = I. | last5 = Estornell | first5 = E. | last6 = Cortes | first6 = D. | title = Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action | journal = Natural Product Reports | year = 2005 | volume = 22 | issue = 2 | pages = 269–303 | pmid = 15806200 | doi = 10.1039/B500186M }} Erratum: {{ cite journal | title = Back Matter | journal = Natural Product Reports | year = 2005 | volume = 22 | issue = 3 | pages = 426 | doi = 10.1039/B503508M }}</ref> Many acetogenins are characterized by [[neurotoxicity]].<ref>{{cite journal | doi = 10.1007/978-3-319-22692-7_2}}</ref>


Examples include:
Examples include:

Revision as of 13:11, 8 February 2018

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.[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)
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.[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

Biological effects

Acetogenins have been investigated for their potential therapeutic use in treating cancer,[5] but this potential is tempered with concerns about neurotoxicity.[6][7][8][9][10]

Purified acetogenins and crude extracts of the common North American pawpaw (Asimina triloba) or the Brazilian pawpaw (Annona muricata) remain under basic research for their possible biological properties.[11][12]

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. ^ . doi:10.1007/978-3-319-22692-7_2. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  4. ^ a b c Alali, F. Q., Liu, X., & Mclaughlin, J. L. (1999). Annonaceous Acetogenins: Recent Progress. Journal of Natural Products, 62(3), 504-540. doi:10.1021/np980406d
  5. ^ Mangal, M; Khan, M. I.; Agarwal, S. M. (2015). "Acetogenins as Potential Anticancer Agents". Anti-cancer agents in medicinal chemistry. 16 (2): 138–59. doi:10.2174/1871520615666150629101827. PMID 26118710.
  6. ^ Ana V. Coria-Téllez; Efigenia Montalvo-Gónzalez; Elhadi M. Yahia; Eva N. Obledo-Vázquez (2016). "Annona muricata: A comprehensive review on its traditional medicinal uses, phytochemicals, pharmacological activities, mechanisms of action and toxicity". Arabian Journal of Chemistry. doi:10.1016/j.arabjc.2016.01.004.
  7. ^ Le Ven, J.; Schmitz-Afonso, I.; Touboul, D.; Buisson, D.; Akagah, B.; Cresteil, T.; Lewin, G.; Champy, P. (2011). "Annonaceae fruits and parkinsonism risk: Metabolisation study of annonacin, a model neurotoxin; evaluation of human exposure". Toxicology Letters. 205: S50. doi:10.1016/j.toxlet.2011.05.197.
  8. ^ Victor R. Preedy; Ronald Ross Watson; Vinood B. Patel, eds. (2011). Nuts and Seeds in Health and Disease Prevention. Academic Press. pp. 434–435.
  9. ^ 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. doi:10.1021/jf504500g. PMID 25594104. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  10. ^ 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. doi:10.1016/j.neuro.2011.10.009. PMID 22130466.
  11. ^ McLaughlin, J.L. (2008). "Paw paw and cancer: annonaceous acetogenins from discovery to commercial products". Journal of Natural Products. 71 (7): 1311–21. doi:10.1021/np800191t. PMID 18598079.
  12. ^ Coothankandaswamy, Veena; Liu, Yang; Mao, Shui-Chun; Morgan, J. Brian; Mahdi, Fakhri; Jekabsons, Mika B.; Nagle, Dale G.; Zhou, Yu-Dong (2010). "The Alternative Medicine Pawpaw and Its Acetogenin Constituents Suppress Tumor Angiogenesis via the HIF-1/VEGF Pathway". Journal of Natural Products. 73 (5): 956–961. doi:10.1021/np100228d. PMC 2890309. PMID 20423107.

External links

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