Search results for "Lactones"

showing 10 items of 98 documents

Acetogenins from Annonaceae family. Their potential biological applications

2019

The aim of this contribution has been to continue with the knowledge about newly isolated acetogenins from Annonaceae family for the last fifteen years. This review will report classification, extraction, isolation, elucidation of the structure, biological activities and mechanism of action of such interesting natural products. In fact, out of the 532 compounds reviewed, 115 previously non-described annonaceous acetogenins have been added to the list of isolated compounds from 2005 to May 2019.

0106 biological sciencesBiological ProductsAcetogeninsbiology010405 organic chemistryStereochemistryAnnonaceaePlant ScienceGeneral MedicineHorticulturebiology.organism_classification01 natural sciencesBiochemistry0104 chemical sciencesLactonesAnnonaceaeAnnonaceous AcetogeninsFuransMolecular Biology010606 plant biology & botanyPhytochemistry
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Effect of acyl-CoA oxidase activity on the accumulation of gamma-decalactone by the yeast Yarrowia lipolytica: a factorial approach.

2007

International audience; beta-Oxidation is a cyclic pathway involved in the degradation of lipids. In yeast, it occurs in peroxisomes and the first step is catalyzed by an acyl-CoA oxidase (Aoxp). The yeast Yarrowia lipolytica possesses several genes (POX) coding for Aoxps. This study is based on the factorial analysis of results obtained with the many POX derivative strains that have been constructed previously. The effect of interactions between Aoxps on the acyl-CoA oxidase (Aox) activity was important even at the second order. We then investigated the effect of Aox activity on growth and lactone production. Aox activity was correlated with acidification of the medium by cells and with ce…

0106 biological sciencesYarrowia lipolyticaMESH: Enzyme ActivationMetabolic Clearance RateMESH: Factor Analysis StatisticalYarrowiaBiologymodèleModels Biological01 natural sciencesApplied Microbiology and BiotechnologyLactones03 medical and health sciencesEnzyme activatorSpecies SpecificityMESH: Computer Simulation010608 biotechnologyCombinatorial Chemistry TechniquesAcyl-CoA oxidaseMESH: Species SpecificityComputer Simulation030304 developmental biologychemistry.chemical_classificationMESH: Metabolic Clearance Rate0303 health sciencesOxidase testmétabolisme des acides grasAcyl-CoA oxidase activityMESH: Acyl-CoA OxidaseMESH: Models BiologicalYarrowia[SDV.BBM.BM]Life Sciences [q-bio]/Biochemistry Molecular Biology/Molecular biologyGeneral MedicinePeroxisomebiology.organism_classificationYeastEnzyme ActivationBiochemistrychemistrylactoneMolecular MedicineMESH: Combinatorial Chemistry TechniquesMESH: YarrowiaAcyl-CoA OxidaseFactor Analysis StatisticalLactoneMESH: Lactones
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Medium-size droplets of methyl ricinoleate are reduced by cell-surface activity in the gamma-decalactone production by Yarrowia lipolytica.

2000

International audience; Size of methyl ricinoleate droplets during biotransformation into gamma-decalactone by Yarrowia lipolytica was measured in both homogenized and non-homogenized media. In non-homogenized but shaken medium, droplets had an average volume surface diameter d32 of 2.5 microm whereas it was 0.7 microm in homogenized and shaken medium. But as soon as yeast cells were inoculated, both diameters became similar at about 0.7 microm and did not vary significantly until the end of the culture. The growth of Y. lipolytica in both media was very similar except for the lag phase which was lowered in homogenized medium conditions.

0106 biological sciences[SDV.BIO]Life Sciences [q-bio]/BiotechnologyTime FactorsCell01 natural sciencesApplied Microbiology and BiotechnologyLactonesBiotransformationMESH : Particle SizeYeastsMESH: Microscopy Confocal[INFO.INFO-BT]Computer Science [cs]/BiotechnologyComputingMilieux_MISCELLANEOUSBiotransformation0303 health sciencesMicroscopyMicroscopy ConfocalbiologyMESH: YeastsMESH : Lactones[SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitologymedicine.anatomical_structureBiochemistryConfocalSURFACE ACTIVERicinoleic Acids[ INFO.INFO-BT ] Computer Science [cs]/BiotechnologyMESH: LactonesMESH : Time Factors03 medical and health sciencesMESH : Biotransformation010608 biotechnologymedicine[SDV.BBM] Life Sciences [q-bio]/Biochemistry Molecular Biology[SDV.BBM]Life Sciences [q-bio]/Biochemistry Molecular BiologyMESH: Particle SizeParticle SizeMESH : Microscopy Confocal[ SDV.BBM ] Life Sciences [q-bio]/Biochemistry Molecular BiologyMethyl ricinoleateMESH: BiotransformationMESH : YeastsChromatography030306 microbiologyMESH: Time Factors[ SDV.BIO ] Life Sciences [q-bio]/BiotechnologyYarrowiabiology.organism_classificationYeastMESH: Ricinoleic AcidsCulture Media[SDV.BIO] Life Sciences [q-bio]/Biotechnology[INFO.INFO-BT] Computer Science [cs]/BiotechnologyMESH : Ricinoleic AcidsMESH: Culture MediaMESH : Culture Media
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Role of quercetin on Caco-2 cells against cytotoxic effects of alternariol and alternariol monomethyl ether.

2015

Molds of the genus Alternaria have been reported as contaminants of a variety of food and feed. Alternaria toxins such as alternariol (AOH) and its naturally occurring monomethyl ether (AME) produce cytotoxicity and oxidative stress in cell cultures. On the other hand, it has been proved that natural polyphenols have antioxidant effect. Quercetin (Quer) is a polyphenol present in berries and other commodities which exhibits these effects. The aims were to evaluate the cytotoxicity of AOH, AME and the binary combination of them, and the cytoprotective effect of Quer exposed simultaneously with AOH, AME and the mycotoxin mixture in human adenocarcinoma (Caco-2) cells. The cytotoxicity and the…

0301 basic medicineAntioxidantStereochemistrymedicine.medical_treatmentAlternariolToxicology03 medical and health scienceschemistry.chemical_compoundLactones0404 agricultural biotechnologymedicineHumansViability assayFood scienceMycotoxinCytotoxicity04 agricultural and veterinary sciencesGeneral Medicine040401 food science030104 developmental biologychemistryCaco-2PolyphenolQuercetinCaco-2 CellsQuercetinFood ScienceEthersFood and chemical toxicology : an international journal published for the British Industrial Biological Research Association
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Binary and tertiary combination of alternariol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol on HepG2 cells: Toxic effects and evaluation of …

2016

Fungi producers of mycotoxins are able to synthesize more than one toxin. Alternariol (AOH) is one of the mycotoxins produced by several Alternaria species, the most common one being Alternaria alternata. The toxins 3-Acetyl-deoxynivalenol (3-ADON) and 15-Acetyl-deoxynivalenol (15-ADON) are acetylated forms of deoxynivalenol (DON) produced by Fusarium graminearum. In the present work it is determined and evaluated the toxic effects of binary and tertiary combination treatment of HepG2 cells with AOH, 3-ADON and 15-ADON, by using the MTT assay (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide), to subsequently apply the isobologram method and elucidate if the mixtures of these m…

0301 basic medicineFusariumCell SurvivalAlternariolToxicologymedicine.disease_causeAlternaria alternata03 medical and health scienceschemistry.chemical_compoundLactones0404 agricultural biotechnologyLiquid chromatography–mass spectrometrymedicineHumansMTT assayMycotoxinChromatographybiologyToxinfood and beverages04 agricultural and veterinary sciencesGeneral MedicineHep G2 Cellsbiology.organism_classification040401 food science030104 developmental biologychemistryAntagonismTrichothecenesToxicology in vitro : an international journal published in association with BIBRA
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Structure-Activity Relationships of Cytotoxic Lactones as Inhibitors and Mechanisms of Action.

2020

Background: Some lactones prevent protein Myb-dependent gene expression. Objective: The object is to calculate inhibitors of Myb-brought genetic manifestation. Methods: Linear quantitative structure–potency relations result expanded, among sesquiterpene lactones of a variety of macrocycles (pseudoguaianolides, guaianolides, eudesmanolides and germacranolides), to establish which part of the molecule constitutes their pharmacophore, and predict their inhibitory potency on Myb-reliant genetic manifestation, which may result helpful as leads for antileukaemic therapies with a new mechanism of action. Results: Several count indices are connected with structure–activity. The α-methylene-γ-lacto…

0301 basic medicineGermacranolidePaclitaxelStereochemistrySesquiterpeneRing (chemistry)Ligands030226 pharmacology & pharmacy03 medical and health scienceschemistry.chemical_compoundLactonesStructure-Activity Relationship0302 clinical medicineTubulinNeoplasmsDrug DiscoverymedicinePotencyMoleculeHumansEtoposidechemistry.chemical_classification030102 biochemistry & molecular biologyAntineoplastic Agents PhytogenicTubulin ModulatorsMolecular Docking SimulationMechanism of actionchemistryStructural Homology ProteinDrug DesignPharmacophoremedicine.symptomTopotecanSesquiterpenesLactoneCurrent drug discovery technologies
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Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells

2015

Alternariol (AOH), a mycotoxin produced by Alternaria sp, appears as food contaminant in fruit, vegetables and cereal products. Its toxicity has been demonstrated, but the mechanisms involved have not been elucidated yet. In this study, the pathways triggered by AOH and degradation products generated on Caco-2 cells were evaluated. Cells were exposed to AOH sub-cytotoxic concentrations of 15, 30 and 60 μM. Cell cycle disruption, the induction of apoptosis/necrosis and changes in mitochondrial membrane potential (Δψm) after 24 and 48 h was asses by flow cytometry. Also, AOH and its degradation products were evaluated after 24 and 48 h by high-performance liquid chromatography with tandem mas…

0301 basic medicineProgrammed cell deathNecrosisAlternariolMitochondrionBiologyToxicologyLactones03 medical and health scienceschemistry.chemical_compound0404 agricultural biotechnologymedicineHumansCell ProliferationMembrane Potential MitochondrialCell DeathCell growthCell CycleAlternaria04 agricultural and veterinary sciencesGeneral MedicineCell cycle040401 food scienceMolecular biologyMitochondria030104 developmental biologychemistryBiochemistryApoptosisToxicityCaco-2 Cellsmedicine.symptomFood ScienceFood and Chemical Toxicology
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Evaluation of Alternaria mycotoxins in strawberries: quantification and storage condition

2016

Alternariol (AOH), alternariol methyl ether (AME) and tentoxin (TEN) are Alternaria mycotoxins produced by the most common post-harvest pathogens of fruits. The production of these metabolites depends on several environmental factors, mainly temperature, water activity, pH and the technological treatments that have been applied to the product. In this study, the occurrence of AOH, AME and TEN was evaluated in strawberries samples stored at different temperatures ranges (at 22 ± 2 or 6 ± 2°C) and different periods (up to 1 month) simulating the current practice of consumer's storage conditions. Sample extraction was performed using a liquid-liquid extraction method prior to LC-MS/MS analysis…

0301 basic medicineSpectrometry Mass Electrospray IonizationWater activityHealth Toxicology and MutagenesisLiquid-Liquid ExtractionFood storageAlternariolFood ContaminationToxicologyFragariaPeptides CyclicLactones03 medical and health scienceschemistry.chemical_compound0404 agricultural biotechnologyRefrigerationTandem Mass SpectrometryFood PreservationFood scienceMycotoxinChromatography High Pressure LiquidbiologyChemistryPublic Health Environmental and Occupational HealthFood preservationAlternaria04 agricultural and veterinary sciencesGeneral ChemistryGeneral MedicineHydrogen-Ion ConcentrationMycotoxinsFood InspectionAlternariabiology.organism_classificationFragaria040401 food scienceTeratogens030104 developmental biologyFood StorageSpainFruitEnvironmental chemistryMutagensFood ScienceFood contaminantFood Additives & Contaminants: Part A
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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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