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MedKoo Cat#: 564543 | Name: Annonacin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Annonacin is a naturally occurring acetogenin found in several species of the Annonaceae family, particularly in fruits like soursop (Annona muricata). It exhibits potent neurotoxic and cytotoxic bioactivity, primarily through the inhibition of mitochondrial complex I (NADH:ubiquinone oxidoreductase), leading to ATP depletion and cell death. Due to its ability to cross the blood-brain barrier and accumulate in neural tissues, annonacin has been implicated in neurodegenerative disorders, particularly atypical parkinsonism observed in regions with high consumption of Annona fruits.

Chemical Structure

Annonacin
Annonacin
CAS#111035-65-5

Theoretical Analysis

MedKoo Cat#: 564543

Name: Annonacin

CAS#: 111035-65-5

Chemical Formula: C35H64O7

Exact Mass: 596.4652

Molecular Weight: 596.89

Elemental Analysis: C, 70.43; H, 10.81; O, 18.76

Price and Availability

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1mg USD 600.00 2 Weeks
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Related CAS #
No Data
Synonym
Annonacin
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
InChi Key
XNODZYPOIPVPRF-CGWDHHCXSA-N
InChi 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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 596.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Salama M, El-Desouky S, Alsayed A, El-Hussiny M, Magdy K, Fekry E, Shabka O, El-Khodery SA, Youssef MA, Sobh M, Mohamed W. 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, Patrikios I, Johnson EO, Sereti E, Dimas K, De Ford C, Fedosova NU, Graier WF, Sokratous K, Kyriakou K, Stephanou A. Annonacin promotes selective cancer cell death via NKA-dependent and SERCA-dependent pathways. Cell Death Dis. 2018 Jul 9;9(7):764. doi: 10.1038/s41419-018-0772-x. PubMed PMID: 29988040; PubMed Central PMCID: PMC6037677. 4: Yap CV, Subramaniam KS, Khor SW, Chung I. Annonacin Exerts Antitumor Activity through Induction of Apoptosis and Extracellular Signal-regulated Kinase Inhibition. Pharmacognosy Res. 2017 Oct-Dec;9(4):378-383. doi: 10.4103/pr.pr_19_17. PubMed PMID: 29263632; PubMed Central PMCID: PMC5717791. 5: Bonneau N, Schmitz-Afonso I, Brunelle A, Touboul D, Champy P. Validation data for the quantification of the Annonaceous acetogenin annonacin in Rat brain by UPLC-MS/MS. Data Brief. 2016 May 4;7:1633-8. doi: 10.1016/j.dib.2016.04.067. eCollection 2016 Jun. PubMed PMID: 27222866; PubMed Central PMCID: PMC4866534. 6: Bonneau N, Schmitz-Afonso I, Brunelle A, Touboul D, Champy P. Quantification of the environmental neurotoxin annonacin in Rat brain by UPLC-MS/MS. Toxicon. 2016 Aug;118:129-33. doi: 10.1016/j.toxicon.2016.03.015. Epub 2016 Apr 4. PubMed PMID: 27058514. 7: Bonneau N, Schmitz-Afonso I, Brunelle A, Touboul D, Champy P. Method development for quantification of the environmental neurotoxin annonacin in Rat plasma by UPLC-MS/MS and application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Nov 1;1004:46-52. doi: 10.1016/j.jchromb.2015.09.039. Epub 2015 Sep 30. PubMed PMID: 26444335. 8: Yamada ES, Respondek G, Müssner S, de Andrade A, Höllerhage M, Depienne C, Rastetter A, Tarze A, Friguet B, Salama M, Champy P, Oertel WH, Höglinger GU. Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice. Exp Neurol. 2014 Mar;253:113-25. doi: 10.1016/j.expneurol.2013.12.017. Epub 2014 Jan 3. PubMed PMID: 24389273. 9: Potts LF, Luzzio FA, Smith SC, Hetman M, Champy P, Litvan I. Annonacin in Asimina triloba fruit: implication for neurotoxicity. Neurotoxicology. 2012 Jan;33(1):53-8. doi: 10.1016/j.neuro.2011.10.009. Epub 2011 Nov 23. PubMed PMID: 22130466. 10: Ko YM, Wu TY, Wu YC, Chang FR, Guh JY, Chuang LY. Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells. J Ethnopharmacol. 2011 Oct 11;137(3):1283-90. doi: 10.1016/j.jep.2011.07.056. Epub 2011 Aug 4. PubMed PMID: 21840388. 11: Oasa M, Hattori Y, Konno H, Makabe H. Synthesis of annonacin isolated from Annona densicoma. Biosci Biotechnol Biochem. 2010;74(6):1274-5. Epub 2010 Jun 7. PubMed PMID: 20530895. 12: Lannuzel A, Ruberg M, Michel PP. Atypical parkinsonism in the Caribbean island of Guadeloupe: etiological role of the mitochondrial complex I inhibitor annonacin. Mov Disord. 2008 Nov 15;23(15):2122-8. doi: 10.1002/mds.22300. Review. PubMed PMID: 18816693. 13: Escobar-Khondiker M, Höllerhage M, Muriel MP, Champy P, Bach A, Depienne C, Respondek G, Yamada ES, Lannuzel A, Yagi T, Hirsch EC, Oertel WH, Jacob R, Michel PP, Ruberg M, Höglinger GU. Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons. J Neurosci. 2007 Jul 18;27(29):7827-37. PubMed PMID: 17634376. 14: Champy P, Höglinger GU, Féger J, Gleye C, Hocquemiller R, Laurens A, Guérineau V, Laprévote O, Medja F, Lombès A, Michel PP, Lannuzel A, Hirsch EC, Ruberg M. Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe. J Neurochem. 2004 Jan;88(1):63-9. PubMed PMID: 14675150. 15: Lannuzel A, Michel PP, Höglinger GU, Champy P, Jousset A, Medja F, Lombès A, Darios F, Gleye C, Laurens A, Hocquemiller R, Hirsch EC, Ruberg M. The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism. Neuroscience. 2003;121(2):287-96. PubMed PMID: 14521988. 16: Yuan SS, Chang HL, Chen HW, Yeh YT, Kao YH, Lin KH, Wu YC, Su JH. Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. Life Sci. 2003 May 9;72(25):2853-61. PubMed PMID: 12697268. 17: Kim DH, Son JK, Woo MH. Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds. Arch Pharm Res. 2001 Aug;24(4):300-6. PubMed PMID: 11534761. 18: Hu TS, Yu Q, Wu YL, Wu Y. Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J Org Chem. 2001 Feb 9;66(3):853-61. PubMed PMID: 11430104. 19: Hu TS, Wu YL, Wu Y. The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins. Org Lett. 2000 Apr 6;2(7):887-9. PubMed PMID: 10768178. 20: Woo MH, Chung SO, Kim DH. cis-Annonacin and (2,4)-cis-and trans-isoannonacins: cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds of Annona cherimolia. Arch Pharm Res. 1999 Oct;22(5):524-8. PubMed PMID: 10549583.