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    Annonacin
    Annonacin
    Information
    CAS No. 111035-65-5 Price
    Catalog No.CFN97856Purity>=98%
    Molecular Weight596.89Type of CompoundLipids
    FormulaC35H64O7Physical DescriptionPowder
    Download Manual    COA    MSDS    SDFSimilar structuralComparison (Web)  (SDF)
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    Annonacin

    Annonacin
    Product Name Annonacin
    CAS No.: 111035-65-5
    Catalog No.: CFN97856
    Molecular Formula: C35H64O7
    Molecular Weight: 596.89 g/mol
    Purity: >=98%
    Type of Compound: Lipids
    Physical Desc.: Powder
    Targets: CDK | P21 | ERK | JNK | STAT | Bcl-2/Bax | Caspase | Estrogen receptor | Progestogen receptor
    Source: The herbs of Annona glabra
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price:
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  • Int Immunopharmacol.2019, 71:22-31
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  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
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  • Biological Activity
    Description: Annonacin is mitochondrial complex I inhibitor, reported to be more toxic than rotenone to mesencephalic neurons; can cause significant cell death in various cancer cell lines. Annonacin induces growth arrest and apoptosis in ERα-related pathways in MCF-7 cells, attenuates MCF-7 xenograft tumor growth while inhibiting ERα, cyclin D1 and Bcl-2 protein expressions in nude mice. Annonacin-induced ATP depletion causes the retrograde transport of mitochondria to the cell soma and induces changes in the intracellular distribution of tau in a way that shares characteristics with some neurodegenerative diseases.
    Targets: CDK | P21 | ERK | JNK | STAT | Bcl-2/Bax | Caspase | Estrogen receptor | Progestogen receptor
    In vitro:
    Neurotoxicology. 2012 Jan;33(1):53-8.
    Annonacin in Asimina triloba fruit: implication for neurotoxicity.[Pubmed: 22130466]
    The acetogenin, Annonacin, from the tropical annonaceous plant Annona muricata, is a lipophilic, mitochondrial complex I inhibitor reported to be more toxic than rotenone to mesencephalic neurons. The temperate annonaceous plant Asimina triloba (pawpaw) is native to the Eastern United States and products are available online. This study determined whether Annonacin is in the pawpaw fruit pulp and whether it or the crude ethyl acetate extract is toxic to cortical neurons.
    METHODS AND RESULTS:
    Pawpaw extract was prepared by pulp extraction with methanol and liquid-liquid partitioning with ethyl acetate (EtOAc). Annonacin was isolated from the crude EtOAc extract via column chromatography using a gradient solvent system of increasing polarity. Mass spectroscopy, nuclear magnetic resonance and infrared spectroscopy were used to compare isolated material with synthetic Annonacin data and a natural Annonacin sample. Toxicity of isolated Annonacin and the total EtOAc extract was determined in primary rat cortical neurons using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The average concentration of Annonacin in the fruit pulp was 0.0701±0.0305mg/g. Purified Annonacin (30.07μg/ml) and crude EtOAc extract (47.96μg/ml) induced 50% death of cortical neurons 48h post treatment. Annonacin toxicity was enhanced in the presence of crude extract.
    CONCLUSIONS:
    Pawpaw fruit contains a high concentration of Annonacin, which is toxic to cortical neurons. Crude fruit extract also induced neurotoxicity, highlighting the need for additional studies to determine the potential risks of neurodegeneration associated with chronic exposure to pawpaw products.
    J Neurosci. 2007 Jul 18;27(29):7827-37.
    Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons.[Pubmed: 17634376]
    A neurodegenerative tauopathy endemic to the Caribbean island of Guadeloupe has been associated with the consumption of anonaceous plants that contain acetogenins, potent lipophilic inhibitors of complex I of the mitochondrial respiratory chain.
    METHODS AND RESULTS:
    To test the hypothesis that Annonacin, a prototypical acetogenin, contributes to the etiology of the disease, we investigated whether Annonacin affects the cellular distribution of the protein tau. In primary cultures of rat striatal neurons treated for 48 h with Annonacin, there was a concentration-dependent decrease in ATP levels, a redistribution of tau from the axons to the cell body, and cell death. Annonacin induced the retrograde transport of mitochondria, some of which had tau attached to their outer membrane.
    CONCLUSIONS:
    Therefore, the Annonacin-induced ATP depletion causes the retrograde transport of mitochondria to the cell soma and induces changes in the intracellular distribution of tau in a way that shares characteristics with some neurodegenerative diseases.
    In vivo:
    Exp Neurol. 2014 Mar;253:113-25.
    Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice.[Pubmed: 24389273]
    Both genetic and environmental factors likely contribute to the neuropathology of tauopathies, but it remains unclear how specific genetic backgrounds affect the susceptibility towards environmental toxins. Mutations in the tau gene have been associated with familial tauopathies, while Annonacin, a plant-derived mitochondrial inhibitor, has been implicated in an environmental form of tauopathy.
    METHODS AND RESULTS:
    We therefore determined whether there was a pathogenic synergy between Annonacin exposure and the expression of the R406W-tau mutation in transgenic mice. We found that Annonacin exposure caused an increase in the number of neurons with phosphorylated tau in the somatodendritic compartment in several brain areas in R406W(+/+) mice as opposed to mice that had only the endogenous mouse tau (R406W(-/-)). Western blot analysis demonstrated a concomitant increase in total tau protein without increase in tau mRNA, but reduced proteasomal proteolytic activity in R406W(+/+), but not R406W(-/-) mice, upon Annonacin-treatment. Phosphorylated tau levels exceeded the increase in total tau protein, along with increased levels of different tau kinases, foremost a striking increase in the p25/p35 ratio, known to activate the tau kinase Cdk5.
    CONCLUSIONS:
    In summary, we observed a synergistic interaction between Annonacin exposure and the presence of the R406W-tau mutation, which resulted in reduced degradation, increased phosphorylation and redistribution of neuronal tau.
    Annonacin Description
    Source: The herbs of Annona glabra
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 1.6754 mL 8.3768 mL 16.7535 mL 33.507 mL 41.8838 mL
    5 mM 0.3351 mL 1.6754 mL 3.3507 mL 6.7014 mL 8.3768 mL
    10 mM 0.1675 mL 0.8377 mL 1.6754 mL 3.3507 mL 4.1884 mL
    50 mM 0.0335 mL 0.1675 mL 0.3351 mL 0.6701 mL 0.8377 mL
    100 mM 0.0168 mL 0.0838 mL 0.1675 mL 0.3351 mL 0.4188 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    J Ethnopharmacol. 2011 Oct 11;137(3):1283-90.
    Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells.[Pubmed: 21840388 ]
    Tamoxifen resistance is common in estrogen receptor-α (ERα)-positive breast cancers. Pawpaw and soursop are anticancer annonaceous plants in complementary medicine. Thus, we studied the effects of Annonacin, an annonaceous acetogenin, in breast cancer cells.
    METHODS AND RESULTS:
    Cell growth and ERα-related pathways were studied. The effects of Annonacin were tested in MCF-7 xenografts in nude mice. RESULTS: In ERα-positive MCF-7 cells, Annonacin (half-effective dose ED(50) = 0.31 μM) and 4-hydroxytamoxifen (ED(50) = 1.13 μM) decreased cell survival whereas Annonacin (0.5-1 μM) increased cell death at 48 h. Annonacin and 4-hydroxytamoxifen were additive in inhibiting cell survival. Annonacin (0.1 μM) induced G(0)/G(1) growth arrest while increasing p21(WAF1) and p27(kip1) and decreasing cyclin D1 protein expression. Annonacin (0.1μM) decreased cyclin D1 protein expression more than 4-hydroxytamoxifen (1 μM). Annonacin (0.1 μM) increased apoptosis while decreasing Bcl-2 protein expression. The combination of Annonacin (0.1 μM) and 4-hydroxytamoxifen (1 μM) decreased Bcl-2 protein expression and ERα transcriptional activity more than Annonacin (0.1 μM) did alone. Annonacin, but not 4-hydroxytamoxifen, decreased ERα protein expression. Moreover, Annonacin decreased phosphorylation of ERK1/2, JNK and STAT3. In nude mice, Annonacin decreased MCF-7 xenograft tumor size at 7-22 days. Moreover, Annonacin decreased ERα, cyclin D1 and Bcl-2 protein expression in the xenograft at 22 days.
    CONCLUSIONS:
    Annonacin induced growth arrest and apoptosis in ERα-related pathways in MCF-7 cells. Annonacin and 4-hydroxytamoxifen were additive in inhibiting cell survival and ERα transcriptional activity. Moreover, Annonacin attenuated MCF-7 xenograft tumor growth while inhibiting ERα, cyclin D1 and Bcl-2 protein expressions in nude mice.
    Cell Research:
    Life Sci. 2003 May 9;72(25):2853-61.
    Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway.[Pubmed: 12697268]
    Annonaceous acetogenins are a group of potential anti-neoplastic agents isolated from Annonaceae plants. In this study, we purified Annonacin, a cytotoxic mono-tetrahydrofuran acetogenin, from the seeds of Annona reticulata and analyzed its biological effects.
    METHODS AND RESULTS:
    Herein, we have shown that Annonacin caused significant cell death in various cancer cell lines. T24 bladder cancer cells at the S phase were more vulnerable to the cytotoxicity of Annonacin. Furthermore, Annonacin activated p21 in a p53-independent manner and arrested T24 cells at the G1 phase. It also induced Bax expression, enhanced caspase-3 activity, and caused apoptotic cell death in T24 cells.
    CONCLUSIONS:
    In summary, these results suggest that Annonacin is potentially a promising anti-cancer compound.
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