Acetogenin - Wikipedia, the free encyclopedia

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Acetogenin
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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]
Examples include:
Annonacin
Annonins
Bullatacin
Uvaricin

Biological effects[edit]
Acetogenins have been investigated for their potential therapeutic use in treating cancer,[3] but this
potential is tempered with concerns about neurotoxicity.[4][5][6][7][8] Well over half of all cancer patients
pursue some sort of complementary and alternative medical treatments.[9] Neither purified acetogenins
nor crude extracts of the pawpaw or the Brazilian pawpaw (Asimina triloba, Annonaceae) have been
approved by the FDA for cancer treatment, but they have exhibited antitumor efficacy both in animal
models and in a limited number of clinical studies.[10] There is a lack of rigorously controlled clinical
trials, casting doubt of the efficacy of acetogenins.[11]
Both the Pawpaw extract and acetogenins appear to inhibit HIF-1 activation by blocking the hypoxic
induction of nuclear HIF-1 protein.[11]

References[edit]
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): 162.

doi:10.3762/bjoc.4.48. PMC 2633664 .

PMID 19190742.
2. ^ Bermejo, A.; Figadre, B.; Zafra-Polo,
M.-C.; Barrachina, I.; Estornell, E.; Cortes,
D. (2005). "Acetogenins from Annonaceae:
Recent Progress in Isolation, Synthesis and

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Acetogenin - Wikipedia, the free encyclopedia

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Mechanisms of Action". Natural Product

Reports. 22 (2): 269303.
doi:10.1039/B500186M. PMID 15806200.
Erratum: "Back Matter". Natural Product
Reports. 22 (3): 426. 2005.
doi:10.1039/B503508M.
3. ^ Mangal, M; Khan, M. I.; Agarwal, S. M.
(2015). "Acetogenins as Potential Anticancer
Agents". Anti-cancer agents in medicinal
chemistry. 16 (2): 13859.
doi:10.2174/1871520615666150629101827.
PMID 26118710.
4. ^ Ana V. Coria-Tllez, Efigenia MontalvoGnzalez, Elhadi M. Yahia, Eva N. ObledoVzquez (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.
5. ^ 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.
6. ^ Victor R. Preedy; Ronald Ross Watson;
Vinood B. Patel, eds. (2011). Nuts and Seeds
in Health and Disease Prevention. Academic
Press. pp. 434435.
7. ^ Robert A. Levine, Kristy M. Richards,
Kevin Tran, Rensheng Luo, Andrew L.

https://en.wikipedia.org/wiki/Acetogenin

Thomas, and Robert E. Smith (2015).

"Determination of Neurotoxic Acetogenins in
Pawpaw (Asimina triloba) Fruit by
LC-HRMS". J. Agric. Food Chem. 63 (4):
10531056. doi:10.1021/jf504500g.
8. ^ 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): 538.
doi:10.1016/j.neuro.2011.10.009.
PMID 22130466.
9. ^ Richardson, M. A.; Sanders, T.; Palmer, J.
L.; Greisinger, A.; Singletary, S. E. (2000).
"Complementary/alternative medicine use in
a comprehensive cancer center and the
implications for oncology.". Journal of
Clinical Oncology. 18 (13): 250514.
PMID 10893280.
10. ^ McLaughlin, J.L. (2008). "Paw paw and
cancer: annonaceous acetogenins from
discovery to commercial products.". Journal
of Natural Products. 71 (7): 131121.
doi:10.1021/np800191t. PMID 18598079.
11. ^ a b 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): 956961.
doi:10.1021/np100228d. PMC 2890309 .
PMID 20423107.

External links[edit]
Media related to Acetogenins at Wikimedia Commons
Retrieved from "https://en.wikipedia.org/w/index.php?title=Acetogenin&oldid=735094394"
Categories:
Fatty alcohols
Polyketides
Hidden categories:
CS1 maint: Uses authors parameter
Commons category with local link same as on Wikidata

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