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Annonacin
AOB34570
CAS 111035-65-5
Chemical Name: 5S-5-methyl-3-
704 Items
Quantity Discount Table - Order More To Get More Price Discount
| Quantity | mg | Unit Price ($/mg or $/Unit) | Final Price |
|---|---|---|---|
| 1 | 5 | $109.65 | Total: $548.25 |
| 1 | 10 | $92.88 | Total: $928.80 |
| 1 | 25 | $78.69 | Total: $1,967.25 |
| 1 | 50 | $67.08 | Total: $3,354.00 |
| 1 | 100 | $58.05 | Total: $5,805.00 |
Overview
Annonacin is a potent and lipophilic acetogenin from A. muricata that inhibits mitochondrial complex I (IC50 = 54.8 nM).1,2 Annonacin induces ATP depletion, tau pathologies, and dopaminergic cell death in rats (EC50s = 134, 44.1, and 60.8 nM, respectively). Quantities of annonacin in the fruit and teas made from leaves of A. muricata are such that a cumulative dose sufficient to induce murine neurodegeneration can be attained in humans by regular consumption within one year. This implicates annonacin in the etiology of taupathologies identified in regions of A. muricata consumption. Annonacin also reduces cell survival (ED50 = 0.31 µM in MCF-7 cells) and decreases MCF-7 xenograft tumor size in nude mice at a dose of 50 mg/kg per day.
Chemical Properties
| Molecular Formula | C35H64O7 |
| Molecular Weight | 596.89 |
| CAS Numbers | 111035-65-5 |
| Solubility | DMSO |
| Purity | 98% by HPLC |
| IUPAC/Chemical Name | (2S)-2-Methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one |
| InChl Key | XNODZYPOIPVPRF-CGWDHHCXSA-N |
| InChl Code | 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 |
| SMILES Code | O=C1C(C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCC)CC2)=C[C@H](C)O1 |
Storage and Handling
0°C (short term), -20°C (long term), desiccated
References
1) Salama M, et. siRNA Blocking of Mammalian Target of Rapamycin (mTOR) Attenuates Pathology in Annonacin-Induced Tauopathy in Mice. Neurotox Res. 2018 Oct 25. doi: 10.1007/s12640-018-9974-3. [Epub ahead of print] PubMed PMID: 30362086.
2) Monsen PJ, Luzzio FA. Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba. J Nat Prod. 2018 Aug 24;81(8):1905-1909. doi: 10.1021/acs.jnatprod.8b00284. Epub 2018 Jul 20. PubMed PMID: 30028612.
3) Yiallouris A, et Annonacin promotes selective cancer cell death via NKA-dependent and SERCA-dependent pathways. Cell Death Dis. 2018 Jul 9;9(7):764.
