Search results for "Terpenoid"

showing 10 items of 221 documents

Anti-HIV Agents Derived from the ent-Kaurane Diterpenoid Linearol

2002

Twenty-six semisynthetic ent-kaurane derivatives of linearol (1) have been investigated for their anti-HIV effects. Five compounds (4, 7, 11, 25, and 26) showed significant activity against HIV replication in H9 lymphocyte cells with EC(50) values in the range <0.1-3.11 microg/mL. With TI values of 163 and 184, compounds 4 and 25 are especially promising for further development as potential anti-HIV agents.

Magnetic Resonance SpectroscopyAnti-HIV AgentsStereochemistryLymphocyteEnt kaurane diterpenoidHuman immunodeficiency virus (HIV)Pharmaceutical ScienceBiologymedicine.disease_causeAnalytical Chemistrychemistry.chemical_compoundDrug DiscoverymedicineCombinatorial Chemistry TechniquesHumansLymphocytesPharmacologyMolecular StructureAnti hivOrganic ChemistryHIVbiology.organism_classificationIn vitroTerpenoidmedicine.anatomical_structureComplementary and alternative medicinechemistryLentivirusSideritisMolecular MedicineDiterpenesDiterpeneJournal of Natural Products
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3-Oxo-rhazinilam:  A New Indole Alkaloid from Rauvolfia serpentina × Rhazya stricta Hybrid Plant Cell Cultures

2000

A new monoterpenoid indole alkaloid, 3-oxo-rhazinilam (1), was isolated from intergeneric somatic hybrid cell cultures of Rauvolfia serpentina and Rhazya stricta, and the structure was determined by detailed 1D and 2D NMR analysis. It was also proved that 3-oxo-rhazinilam (1) is a natural constituent of the hybrid cells.

Magnetic Resonance SpectroscopyLactamsPharmaceutical SciencePharmacognosyRhazya strictaRhazinilamMass SpectrometryRauwolfiaAnalytical Chemistrychemistry.chemical_compoundAlkaloidsRauvolfia serpentinaDrug DiscoveryBotanyCells CulturedPharmacologyPlants MedicinalIndole alkaloidbiologyApocynaceaeOrganic ChemistryIndolizinesbiology.organism_classificationCoculture TechniquesTerpenoidSomatic fusionComplementary and alternative medicinechemistryMolecular MedicineSpectrophotometry UltravioletJournal of Natural Products
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Effects of ajugarins and related neoclerodane diterpenoids on feeding behaviour of Leptinotarsa decemlineata and Spodoptera exigua larvae

2001

Three naturally occurring ajugarins and seven semisynthetic derivatives of them, possessing different functionalities in the decalin part, together with two natural furoneoclerodane diterpenes, have been assessed as feeding behavior modifying agents of larvae of the generalist Spodoptera exigua and a specialist like Leptinotarsa decemlineata. Ajugarin I and some of its derivatives exhibited a significant antifeedant activity against larvae of S. exigua in both choice and no-choice assays. Conversely, the furoneoclerodane diterpenes only presented antifeedant activity against larvae of L. decemlineata. These results indicate that the biological action of the tested substances is strongly mod…

Magnetic Resonance SpectroscopyPlant ScienceSpodopteraHorticultureSpodopteraBiochemistryLepidoptera genitaliachemistry.chemical_compoundExiguaBotanyAnimalsMolecular BiologyLeptinotarsaLarvabiologyfungiFeeding BehaviorGeneral Medicinebiology.organism_classificationTerpenoidColeopterachemistryBiochemistryLarvaNoctuidaeDiterpenesDiterpenePhytochemistry
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Two new biologically active triterpene saponins from Acanthophyllum squarrosum.

2000

Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect …

Magnetic Resonance SpectroscopySpectrophotometry InfraredStereochemistryChemical structureMolecular Sequence DataSaponinPharmaceutical SciencePharmacognosySpectrometry Mass Fast Atom BombardmentPlant RootsAnalytical Chemistrychemistry.chemical_compoundTriterpeneAdjuvants ImmunologicDrug DiscoveryLymphocytesOleanolic AcidOleanolic acidPharmacologychemistry.chemical_classificationPlants MedicinalPlant ExtractsHydrolysisOrganic ChemistryGlycosideNuclear magnetic resonance spectroscopySaponinsTerpenoidComplementary and alternative medicinechemistryCarbohydrate SequenceMolecular MedicineCell DivisionJournal of natural products
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A new biologically active acylated triterpene saponin from Silene fortunei.

1998

A new acylated triterpene-saponin (1), together with a mixture of the known jenisseensosides C and D, has been isolated from the roots of Silene fortunei. The structure of the new compound was established by chemical means and spectroscopic methods as 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28 -O- [[alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl- (1-->3)-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)]-[beta-D- glucopyranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranosyl]quillaic acid. This saponin showed a significant enhancement of granulocyte phagocytosis in vitro.

Magnetic Resonance SpectroscopyStereochemistryChemical structureT-LymphocytesMolecular Sequence DataSaponinPharmaceutical ScienceUronic acidPharmacognosySpectrometry Mass Fast Atom BombardmentLymphocyte ActivationAnalytical Chemistrychemistry.chemical_compoundTriterpenePhagocytosisDrug DiscoveryCarbohydrate ConformationOleanolic AcidPharmacologychemistry.chemical_classificationSilenePlants MedicinalbiologyChemistryOrganic ChemistryGlycosideSaponinsbiology.organism_classificationTerpenoidTriterpenesComplementary and alternative medicineCarbohydrate SequenceMolecular MedicineGranulocytesJournal of natural products
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Three new acylated triterpene saponins from Acanthophyllum squarrosum.

2001

Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--3)-beta-D-xylopyranosyl-(1--4)-beta-D-xylopyranosyl-(1--4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1--2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--4)-alpha-L-rhamnopyranosyl-(1--2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1--3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta…

Magnetic Resonance SpectroscopyStereochemistryMolecular Sequence DataSaponinPharmaceutical SciencePlant RootsAcanthophyllum squarrosumMass SpectrometryAnalytical ChemistryTriterpenoidTriterpeneDrug DiscoveryOleanolic AcidPharmacologychemistry.chemical_classificationMolecular StructureTerpenesOrganic ChemistryGlycosidePlantsSaponinsTerpenoidTriterpenesComplementary and alternative medicinechemistryCarbohydrate SequenceMolecular MedicineJournal of natural products
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Isolation and Structure Elucidation of a New Indole Alkaloid from Rauvolfia serpentina Hairy Root Culture: The First Naturally Occurring Alkaloid of …

2002

A new monoterpenoid indole alkaloid, 10-hydroxy- N(alpha)-demethyl-19,20-dehydroraumacline ( 1), was isolated as a mixture of E- and Z-isomers from hairy root culture of Rauvolfia serpentina Benth. ex Kurz (Apocynaceae) and the structure was determined by 1D and 2D NMR analyses. The new indole alkaloid represents the first naturally occurring alkaloid of the raumacline group and its putative biosynthetical pathway is discussed.

Magnetic Resonance SpectroscopyStereochemistryMonoterpenePharmaceutical SciencePharmacognosyPlant RootsRauwolfiaIndole AlkaloidsAnalytical ChemistryRauvolfia serpentinaDrug DiscoveryBotanyCells CulturedPharmacologyCarbon IsotopesMolecular StructurebiologyApocynaceaeIndole alkaloidPlant ExtractsAlkaloidOrganic ChemistryStereoisomerismbiology.organism_classificationSecologanin Tryptamine AlkaloidsTerpenoidComplementary and alternative medicineHairy root cultureMolecular MedicinePlanta Medica
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Triterpene Saponins from Tupidanthus calyptratus

2001

Five new bisdesmosidic saponins (1--5) were isolated from the aerial parts of Tupidanthus calyptratus. Their structures were determined by (1)H--(1)H correlation spectroscopy (COSY, TOCSY, ROESY) and (1)H--(13)C correlation (HSQC, HMBC) NMR experiments, FABMS, and chemical data.

Magnetic Resonance SpectroscopyStereochemistrySaponinOligosaccharidesPharmaceutical ScienceSpectrometry Mass Fast Atom BombardmentPharmacognosyAnalytical ChemistryTriterpeneDrug DiscoveryHumansPharmacologychemistry.chemical_classificationPlants MedicinalChemistryOrganic ChemistryGlycosideSaponinsAntineoplastic Agents PhytogenicTriterpenesTerpenoidXylosideItalyComplementary and alternative medicineTriterpene SaponinsArialiaceae plantsMolecular MedicineDrug Screening Assays AntitumorTwo-dimensional nuclear magnetic resonance spectroscopyHeteronuclear single quantum coherence spectroscopy
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Bidentatoside I, a New Triterpene Saponin from Achyranthes bidentata

2001

Bidentatoside I (1) is a new triterpene saponin bearing an unusual dioxopropionic acid unit, isolated from the roots of Achyranthes bidentata. Structural elucidation was performed mainly by chemical and homo- and heteronuclear 2D NMR techniques. This compound did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.

Magnetic Resonance SpectroscopyStereochemistrySaponinPharmaceutical ScienceAntineoplastic AgentsUronic acidPharmacognosyAnalytical ChemistryMagnoliopsidachemistry.chemical_compoundTriterpeneDrug DiscoveryTumor Cells CulturedHumansAchyranthes bidentataPharmacologychemistry.chemical_classificationbiologyOrganic ChemistryGlycosideSaponinsbiology.organism_classificationTriterpenesTerpenoidModels ChemicalComplementary and alternative medicinechemistryBiochemistryHeteronuclear moleculeColonic NeoplasmsMolecular MedicineDrug Screening Assays AntitumorJournal of Natural Products
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Two New Glycosides from Astragalus caprinus

2001

A new glycoside of flavonol (1) and a new glycoside of a cycloartane-type triterpene (2) were isolated from the leaves and the roots of Astragalus caprinus, respectively. Their structures were elucidated in turn by spectroscopic data interpretation as 3-O-[[beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->6)][beta-D-apiofuranosyl(1-->2)]]-beta-D-galactopyranosyl kaempferol (1) and 3-O-(beta-D-xylopyranosyl)-24-O-(beta-D-glucopyranosyl)-20,25-epoxycycloartane-3beta,6alpha,16beta,24alpha-tetrol (2).

Magnetic Resonance SpectroscopyTunisiaSpectrophotometry InfraredStereochemistryFlavonoidSaponinPharmaceutical ScienceSpectrometry Mass Fast Atom BombardmentPharmacognosyPlant RootsAnalytical Chemistrychemistry.chemical_compoundTriterpeneDrug DiscoveryTetrasaccharideGlycosidesKaempferolsFlavonoidsPharmacologychemistry.chemical_classificationPlants MedicinalHydrolysisOrganic ChemistryGlycosideSaponinsTriterpenesTerpenoidPlant LeavesComplementary and alternative medicinechemistryMolecular MedicineSpectrophotometry UltravioletKaempferolJournal of Natural Products
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