annonacin
Identification
| Name | annonacin |
| CAS Number | 111035-65-5 |
| FDA UNII | 40372ET6TM |
| Molecular Formula | C35 H64 O7 |
| Molecular Weight | 596.88948000 |
| Nikkaji Number | J246.239G |
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 Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for annonacin usage levels up to | not for fragrance use. |
| Recommendation for annonacin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.