Annonacin

Annonacin

Names
IUPAC name (5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13- [(2R,5R)-5-[(1R)-1- hydroxytridecyl]-2-tetrahydrofuranyl] tridecyl]-5H-furan-2-one
Identifiers
CAS Number	111035-65-5
ChEMBL	ChEMBL476498
ChemSpider	314587
Jmol interactive 3D	Image Image
PubChem	354398
InChI InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1 Key: XNODZYPOIPVPRF-CGWDHHCXSA-N InChI=1/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1 Key: XNODZYPOIPVPRF-CGWDHHCXBQ
SMILES CCCCCCCCCCCCC(C1CCC(O1)C(CCCCC(CCCCCC(CC2=CC(OC2=O)C)O)O)O)O O=C\1O[C@H](/C=C/1C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCC)CC2)C
Properties
Chemical formula	C35H64O7
Molar mass	596.89 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Annonacin is a chemical found in some fruits such as the custard apple and soursop (and others from the family Annonaceae). It is a member of the class of compounds known as acetogenins. Some reports concluded that regular consumption in rats (3.8 and 7.6 mg per kg per day for 28 days) caused brain lesions consistent with Parkinson's disease.^[1][2]

Along with other acetogenins, annonacin is reported to block mitochondrial complex I (NADH-dehydrogenase), which is responsible for the conversion of NADH to NAD⁺ and the build-up of a proton gradient over the mitochondrial inner membrane. This effectively disables a cell's ability to generate ATP via an oxidative pathway, ultimately forcing a cell into apoptosis or necrosis.^[3]

References

1. Lannuzel, A.; Michel, P. P.; Höglinger, G. U.; Champy, P.; Jousset, A.; Medja, F.; Lombès, A.; Darios, F.; et al. (2003). "The Mitochondrial Complex I Inhibitor Annonacin is Toxic to Mesencephalic Dopaminergic Neurons by Impairment of Energy Metabolism". Neuroscience 121 (2): 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988.
2. Champy, P.; Höglinger, G. U.; Féger, J.; Gleye, C.; Hocquemiller, R.; Laurens, A.; Guérineau, V.; Laprévote, O.; et al. (2003). "Annonacin, a Lipophilic Inhibitor of Mitochondrial Complex I, induces Nigral and Striatal Neurodegeneration in Rats: Possible Relevance for Atypical Parkinsonism in Guadeloupe". Journal of Neurochemistry 88 (1): 63–69. doi:10.1046/j.1471-4159.2003.02138.x. PMID 14675150.
3. McLaughlin, J. L. (2008). "Paw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial Products". Journal of Natural Products 71 (7): 1311–1321. doi:10.1021/np800191t. PMID 18598079.

External links

• Pomper, K. W.; Lowe, J. D.; Crabtree, S. B.; Keller, W. (2009). "Identification of Annonaceous Acetogenins in the Ripe Fruit of the North American Pawpaw (Asimina triloba)" (pdf). Journal of Agricultural and Food Chemistry 57 (18): 8339–8343. doi:10.1021/jf9018239. PMID 19711911.