GLPBio

Annonacin

Catalog No.: GC18203Purity:>98.00%
Annonacin is a mitochondrial complex I inhibitor that induces features of tau pathology.

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Annonacin
Cas No.: 111035-65-5
500ugIn Stock
$112.00
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1mgIn Stock
$202.00
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5mgIn Stock
$496.00
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10mgIn Stock
$693.00
1

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Description

Annonacin is a mitochondrial complex I inhibitor that induces features of tau pathology[1]. Annonacin elicits the redistribution of abnormally phosphorylated tau from neurites to cell bodies in striatal neuronal cultures and contributes to degenerative Caribbean atypical parkinsonism (CAP) by modulating the production of tau and α-synuclein pathogenic protein assemblies[2]. Annonacin has been widely used in preclinical models to regulate cellular energy metabolism and kill tumor cells[3].

In vitro, Annonacin treatment for 48 hours significantly inhibited the viability of ES2, A2780, IOSE-80, and liver MIHA cells, with IC50 values of 15.12µM, 10.21µM, 15.48µM, and 28.92µM, respectively[4]. Incubation with 10µg/ml Annonacin for 24 hours induced apoptosis in T24 cells, arrested the cells at the G1 phase, and markedly enhanced the expression of p21[5]. Treatment with 25nM Annonacin for 48 hours reduced the proliferation of LUHMES cells, leading to an increase in the mRNA expression of the tau protein 4R subtype and a decrease in the expression of the splicing factor SRSF2[6].

In vivo, Annonacin treatment via intraperitoneal injection at a dose of 50mg/kg/day for 21 days reduced tumor growth in the MCF-7 xenograft tumor mouse model, accompanied by decreased expression of ERα, cyclin D1, and Bcl-2 proteins[7]. Continuous subcutaneous injection of Annonacin at a dose of 9mg/kg/day for 3 consecutive days enhanced tau protein levels in the brains of R406W+/+ tau transgenic mice[8].

References:
[1] Costa M F D, Rösler T W, Höglinger G U. Exploring the neuroprotective potential of Nrf2-pathway activators against annonacin toxicity[J]. Scientific reports, 2024, 14(1): 20123.
[2] González‐Lizárraga F, Boluda S, Hidalgo J R, et al. Protein coaggregation in Caribbean atypical parkinsonism: The contribution of annonacin[J]. Neuropathology and applied neurobiology, 2025, 51(4): e70026.
[3] das Chagas Lima N N, Faustino D C, Allahdadi K J, et al. Acetogenins from Annonaceae plants: potent antitumor and neurotoxic compounds[J]. PharmaNutrition, 2022, 20: 100295.
[4] He Y, Tong J, Li Z, et al. Anticancer and chemo-sensitizing effects of annonacin via p53-mediated DNA damage in ovarian cancer[J]. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 2025, 1871(7): 167971.
[5] Yuan S S F, Chang H L, Chen H W, et al. Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax-and caspase-3-related pathway[J]. Life Sciences, 2003, 72(25): 2853-2861.
[6] Bruch J, Xu H, De Andrade A, et al. Mitochondrial complex 1 inhibition increases 4-repeat isoform tau by SRSF2 upregulation[J]. PloS one, 2014, 9(11): e113070.
[7] Ko Y M, Wu T Y, Wu Y C, et al. Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells[J]. Journal of ethnopharmacology, 2011, 137(3): 1283-1290.
[8] Yamada E S, Respondek G, Müssner S, et al. Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice[J]. Experimental neurology, 2014, 253: 113-125.

Protocol

Cell experiment [1]:

Cell lines

A2780 cells

Preparation Method

A2780 cells were cultured in RPMI 1640 medium, supplemented with 10% fetal bovine serum and 1% penicillin-streptomycin, at 37°C in an incubator with 5% CO2. Cells were seeded at a density of approximately 6×103 cells per well in 96-well plates overnight and were treated with different concentrations of Annonacin (0, 1.25, 2.5, 5, 10, 20, and 40µM). After 48h, cell proliferation was measured.

Reaction Conditions

0, 1.25, 2.5, 5, 10, 20, and 40µM; 48h

Applications

Annonacin treatment markedly reduced cell proliferation in A2780 cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

Female BALB/cA-nu mice

Preparation Method

Female BALB/cA-nu mice (4 weeks old) were housed in specific pathogen-free conditions and fed standard mouse chow and water ad libitum. MCF-7 cells (5×106 cells in 200μl PBS) were injected subcutaneously into the flanks, and tumors were allowed to develop for 30 days. Then eleven mice were randomly divided into two groups. Annonacin-treated mice (n=6) were intraperitoneally injected daily with Annonacin (50mg/kg/day) in 200μl of 25% polyethylene glycol for 21 days. Control mice (n=5) were intraperitoneally injected daily with 200μl of 25% polyethylene glycol. Tumor volume was measured using calipers at 0, 3, 7, 11, 15, 19, and 22 days.

Dosage form

50mg/kg/day; 21 days; i.p.

Applications

Annonacin treatment significantly inhibited tumor growth in mice with MCF-7 xenografts.

References:
[1] He Y, Tong J, Li Z, et al. Anticancer and chemo-sensitizing effects of annonacin via p53-mediated DNA damage in ovarian cancer[J]. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 2025, 1871(7): 167971.
[2] Ko Y M, Wu T Y, Wu Y C, et al. Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells[J]. Journal of ethnopharmacology, 2011, 137(3): 1283-1290.

Product Documents

Purity:>98.00%Appearance:A solid

Chemical Properties

CAS No.
111035-65-5
Chemical Name
5S-5-methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-tetrahydro-5-[(1R)-1-hydroxytridecyl]-2-furanyl]tridecyl]-2(5H)-furanone
SMILES
O=C1O[C@@H](C)C=C1C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@]2([H])CC[C@@]([C@H](O)CCCCCCCCCCCC)([H])O2
Molecular Formula
C35H64O7
Molecular Weight
596.9
Solubility
DMF: 10 mg/ml,DMSO: 20 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml,Ethanol: 1 mg/ml
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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