Search results for "Annonacin"

showing 5 items of 5 documents

Acetogenins from Annonaceae: Recent Progress in Isolation, Synthesis and Mechanisms of Action

2005

Covering: the literature from 1998 to 2004 The aim of the present review is to summarise the knowledge about newly isolated acetogenins (ACGs) in the last six years. It will also report the total syntheses that have allowed either the confirmation or the revision of some structures, together with the biological activities and mechanism of action of such interesting natural products. In fact, of the 417 isolated compounds reviewed, over 176 have been added during the period from 1998 to 2004.

AcetogeninsIsolation (health care)StereochemistryAnnonacinAnnonaceaeComputational biologyBiochemistryLactoneschemistry.chemical_compoundDrug DiscoverymedicineMolecular StructureTraditional medicinebiologyChemistryOrganic ChemistryGeneral Medicinebiology.organism_classificationAntineoplastic Agents PhytogenicAction (philosophy)Mechanism of actionAnnonaceaeAcetogeninFatty AlcoholsAnnonaceous Acetogeninsmedicine.symptomBullatacinChemInform
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Inhibitory effects on mitochondrial complex I of semisynthetic mono-Tetrahydrofuran acetogenin derivatives

2003

Modifications in the terminal alpha,beta-unsaturated gamma-methyl-gamma-lactone moiety or in the alkyl chain that links this terminal gamma-lactone with the alpha,alpha'-dihydroxylated THF system of the natural mono-tetrahydrofuranic acetogenins, annonacin and annonacinone, led to the preparation of eight semisynthetic derivatives. Their inhibitory effects on mitochondrial complex I is discussed and compared with that of the classical complex I inhibitor, rotenone.

AcetogeninsStereochemistryClinical BiochemistryRespiratory chainAnnonacinPharmaceutical ScienceBiochemistryChemical synthesisLactoneschemistry.chemical_compoundMultienzyme ComplexesDrug DiscoveryMoietyNADH NADPH OxidoreductasesEnzyme InhibitorsFuransMolecular BiologyTetrahydrofuranchemistry.chemical_classificationElectron Transport Complex IOrganic ChemistryRotenoneKineticschemistryAcetogeninMolecular MedicineFatty AlcoholsLactoneBioorganic & Medicinal Chemistry Letters
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Cytotoxicity and antileishmanial activity of Annona muricata pericarp

2000

Abstract Hexane, ethyl acetate and methanol extracts of Annona muricata pericarp were tested in vitro against Leishmania braziliensis and L. panamensis promastigotes, and against cell line U-937. The ethyl acetate extract was more active than the other extracts and even of Glucantime® used as reference substance. Its fractionation led to the isolation of three acetogenins — annonacin, annonacin A and annomuricin A.

Chemical structureAntiprotozoal AgentsEthyl acetateAnnonacinFractionationCell LineLactoneschemistry.chemical_compound4-ButyrolactoneDrug DiscoveryAnimalsHumansFuransMedicinal plantsCytotoxicityAnnona muricataLeishmaniaPharmacologyPlants MedicinalbiologyTraditional medicinePlant ExtractsGeneral Medicinebiology.organism_classificationLeishmania braziliensischemistryBiochemistryFitoterapia
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Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I).

1994

Natural products from the plants of the family Annonaceae, collectively called Annonaceous acetogenins, are very potent inhibitors of the NADH-ubiquinone reductase (Complex I) activity of mammalian mitochondria. The properties of five of such acetogenins are compared with those of rotenone and piericidin, classical potent inhibitors of Complex I. Rolliniastatin-1 and rolliniastatin-2 are more powerful than piericidin in terms of both their inhibitory constant and the protein-dependence of their titre in bovine submitochondrial particles. These acetogenins could be considered therefore the most potent inhibitors of mammalian Complex I. Squamocin and otivarin also have an inhibitory constant …

StereochemistryPyridinesSubmitochondrial ParticlesAnnonacinRespiratory chainIn Vitro TechniquesBiochemistryMitochondria Heartchemistry.chemical_compoundRotenoneAnimalsNADH NADPH OxidoreductasesSubmitochondrial particleFuransMolecular BiologyNADH dehydrogenase complexchemistry.chemical_classificationElectron Transport Complex IPlants MedicinalbiologyMolecular StructureCell BiologyRotenonebiology.organism_classificationEnzymechemistryBiochemistryAnnonaceaeCattleBullatacinResearch Article
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Acetogenins from Annona glabra seeds

1998

Abstract From the cytotoxic ethanol extract of Annona glabra seeds, a new mono-tetrahydrofuranic (mono-THF) acetogenin, glabranin, as well as pair of 22-epimer bis-THF acetogenins, were isolated by semipreparative HPLC. Four known mono-THF acetogenins with an identical threo/trans/threo relative configuration, annonacin, annonacinone, corossolin and corossolone, were found to be potent inhibitors of complex I of the mitochondrial respiratory chain.

chemistry.chemical_classificationbiologyStereochemistryAnnonacinRespiratory chainPlant ScienceGeneral MedicineHorticultureCorossolonebiology.organism_classificationBiochemistrychemistry.chemical_compoundMitochondrial respiratory chainchemistryAnnona glabraAnnonaceaeAcetogeninMolecular BiologyLactonePhytochemistry
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