annonacin

CAS: 111035-65-5 C35 H64 O7 MW: 596.88948000

Identification

Nameannonacin
CAS Number111035-65-5
FDA UNII40372ET6TM
Molecular FormulaC35 H64 O7
Molecular Weight596.88948000
Nikkaji NumberJ246.239G

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 7.712e-005 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for annonacin usage levels up tonot for fragrance use.
Recommendation for annonacin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

guanabana fruit

Synonyms

(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 PubMed: Annonacin Exerts Antitumor Activity through Induction of Apoptosis and Extracellular Signal-regulated Kinase Inhibition. PubMed: Characterization of interactions of eggPC lipid structures with different biomolecules. PubMed: Acetogenins and alkaloids during the initial development of Annona muricata L. (Annonaceae). PubMed: Annona muricata leaves extracts prevent DMBA/TPA-induced skin tumorigenesis via modulating antioxidants enzymes system in ICR mice. PubMed: Structural Characterisation of Acetogenins from Annona muricata by Supercritical Fluid Chromatography Coupled to High-Resolution Tandem Mass Spectrometry. PubMed: The Value of Caspase-3 after the Application of Annona muricata Leaf Extract in COLO-205 Colorectal Cancer Cell Line. PubMed: The fruit of Annona squamosa L. as a source of environmental neurotoxins: From quantification of squamocin to annotation of Annonaceous acetogenins by LC-MS/MS analysis. PubMed: PERK activation mitigates tau pathology in vitro and in vivo PubMed: Chronic consumption of Annona muricata juice triggers and aggravates cerebral tau phosphorylation in wild-type and MAPT transgenic mice. PubMed: Validation data for the quantification of the Annonaceous acetogenin annonacin in Rat brain by UPLC-MS/MS. PubMed: Quantification of the environmental neurotoxin annonacin in Rat brain by UPLC-MS/MS. PubMed: Method development for quantification of the environmental neurotoxin annonacin in Rat plasma by UPLC-MS/MS and application to a pharmacokinetic study. PubMed: Acetogenins as Potential Anticancer Agents. PubMed: Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS. PubMed: Mitochondrial complex 1 inhibition increases 4-repeat isoform tau by SRSF2 upregulation. PubMed: Styryllactones and acetogenins from the fruits of Goniothalamus macrocalyx. PubMed: Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice. PubMed: Natural toxins implicated in the development of Parkinson's disease. PubMed: Annonacin in Asimina triloba fruit: implication for neurotoxicity. PubMed: Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells. PubMed: Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23). PubMed: Synthesis of annonacin isolated from Annona densicoma. PubMed: The alternative medicine pawpaw and its acetogenin constituents suppress tumor angiogenesis via the HIF-1/VEGF pathway. PubMed: Complex I: inhibitors, inhibition and neurodegeneration. PubMed: Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies. PubMed: Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I. PubMed: Atypical parkinsonism in the Caribbean island of Guadeloupe: etiological role of the mitochondrial complex I inhibitor annonacin. PubMed: Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons. PubMed: Atypical parkinsonism in Guadeloupe: a common risk factor for two closely related phenotypes? PubMed: Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae? PubMed: Acetogenins in Annona muricata L. (annonaceae) leaves are potent molluscicides. PubMed: Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe. PubMed: Montacin and cis-montacin, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona montana. PubMed: In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I. PubMed: Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe. PubMed: Inhibitory effects on mitochondrial complex I of semisynthetic mono-tetrahydrofuran acetogenin derivatives. PubMed: The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism. PubMed: Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. PubMed: Selective action of acetogenin mitochondrial complex I inhibitors. PubMed: [Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins]. PubMed: New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata. PubMed: Cytotoxic compounds from Annonaceus species as DNA topoisomerase I poisons. PubMed: Annonaceous acetogenins from the leaves of Annona montana. PubMed: Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana. PubMed: Murihexol, a linear acetogenin from Annona muricata. PubMed: Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds. PubMed: Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. PubMed: Three novel monotetrahydrofuran annonaceous acetogenins from Annona montana. PubMed: Insecticidal and mutagenic evaluation of two annonaceous acetogenins. PubMed: The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins. PubMed: Cytotoxicity and antileishmanial activity of Annona muricata pericarp. PubMed: cis-Annonacin and (2,4)-cis-and trans-isoannonacins: cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds of Annona cherimolia. PubMed: Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba. PubMed: A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii. PubMed: The localisations in liposomal membranes of the tetrahydrofuran ring moieties of the annonaceous acetogenins, annonacin and sylvaticin, as determined by 1H NMR spectroscopy. PubMed: Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea. PubMed: In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins. PubMed: [Studies on the chemical constituents of Annona muricata]. PubMed: Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba. PubMed: Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata. PubMed: Determination of structure-activity relationships of Annonaceous acetogenins by inhibition of oxygen uptake in rat liver mitochondria. PubMed: Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata. PubMed: Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia. PubMed: Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata. PubMed: Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata. PubMed: Bioactive annonaceous acetogenins from the bark of Xylopia aromatica. PubMed: Biologically active acetogenins from stem bark of Asimina triloba. PubMed: [Annomonysvin: a new cytotoxic gamma-lactone-monotetrahydrofuranyl acetogenin from Annona montana]. PubMed: [Annonacins and Annonastatin from Annona squamosa]. PubMed: Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae). PubMed: Annonacin, a novel, biologically active polyketide from Annona densicoma.