Acetogenin

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:

Use in treating cancer

Well over half of all cancer patients pursue some sort of complementary and alternative medical treatments.[3] 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.[4]

Both the Pawpaw extract and acetogenins appear to inhibit HIF-1 activation by blocking the hypoxic induction of nuclear HIF-1α protein.[5]

There is, in the opinion of Coothankandaswamy, a lack of rigorously controlled clinical trials, casting a shadow on the observation that the administration of pawpaw capsules rich in acetogenins decreased tumor size, reduced tumor blood flow, suppressed metastasis, and improved survival in cancer patients.

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. ↑ 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): 2505–14. PMID 10893280.
  4. ↑ 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.
  5. ↑ 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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