Annonacin

Catalog No. BCN4734
CAS RN 111035-65-5
Molecular Weight 596.89
Molecular Formula C35H64O7
Database [PubChem]:382153334
[ChEBI]:
[PCIDB]:43268

Definition

Standard 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

Biological Activity

Annonacin, a natural lipophilic mitochondrial complex I inhibitor, can increase phosphorylation of tau in the brain of FTDP-17 transgenic mice, and induce nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe.[1,2]
Annonacin in Asimina triloba fruit has neurotoxicity, more toxic than rotenone to mesencephalic neurons.[3]
Annonacin has cytotoxicity , it can activate p21 in a p53-independent manner and arrested T24 cells at the G1 phase, induce Bax expression, enhance caspase-3 activity, and cause apoptotic cell death in T24 cells, suggests that annonacin is potentially a promising anti-cancer compound.[4]
Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells.[5]

Product information

English website: Annonacin
Japanese website: Annonacin
Chinese website: Annonacin

References

[1] Yamada E S, Respondek G, Müssner S, et al. Exp Neurol, 2014, 253:113-25.
[2] Champy P, Höglinger G U, Féger J, et al. J Neurochem, 2004, 88(1):63–9.
[3] Potts L F, Luzzio F A, Smith S C, et al. Neurotoxicology, 2012, 33(1):53-8.
[4] Yuan S S F, Chang H L, Chen H W, et al. Life Sci, 2003, 72(25):2853-61.
[5] Ko Y M, Wu T Y, Wu Y C, et al. J Ethnopharmacol, 2011, 137(3):1283-90.
[6] Sun L, Yu J G, Li D Y,et al. Pharm J, 2001, 36 (09): 153-8.