Search results for "Echinocystic acid"

showing 5 items of 5 documents

Unusual oleanane-type saponins from Arenaria montana

2010

Three oleanane-type saponins, 3-O-β-d-glucopyranosylechinocystic acid 28-O-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-α-l-rhamnopyranosyl ester (1), 3-O-β-d-glucopyranosylechinocystic acid 28-O-α-l-arabinopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-α-l-rhamnopyranosyl ester (2), 3-O-β-d-glucopyranosylcaulophyllogenin 28-O-β-d-apiofuranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[β-d-apiofuranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-α-l-rhamnopyranosyl ester (3) were isolated from the whole plant of Arenaria montana. Their unusual structures for the Caryophyllaceae family were established mainly by 2D NMR techniques and mass spectrometry.

Arenaria montanaMagnetic Resonance SpectroscopyStereochemistryChemical structureArenaria PlantSaponinCaryophyllaceaeAntineoplastic AgentsPlant ScienceHorticultureMass spectrometryBiochemistryMass Spectrometrychemistry.chemical_compoundCell Line TumorBotanyHumansOleanolic AcidMolecular BiologyOleananeCell Proliferationchemistry.chemical_classificationDose-Response Relationship DrugMolecular StructurebiologyStereoisomerismGeneral MedicineSaponinsbiology.organism_classificationchemistryDrug Screening Assays AntitumorEchinocystic acidTwo-dimensional nuclear magnetic resonance spectroscopyPhytochemistry
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A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents.

2003

The aim of this review is to update current knowledge on the betulinic, ursolic and echinocystic acids and their natural and semisynthetic analogs, focussing on their cytotoxic and anti-HIV activities. Then, the last results of the authors' team on unusual semisynthetic derivatives of these triterpenoids will be presented in order to establish structure/activity relationships.

PharmacologyMolecular StructureAnti hivChemistryAnti-HIV AgentsTumor cellsAntineoplastic AgentsGeneral MedicinePharmacologyTriterpenesStructure-Activity RelationshipTriterpenoidDrug DiscoveryHIV-1Tumor Cells CulturedStructure–activity relationshipHumansEchinocystic acidOleanolic AcidBetulinic AcidPentacyclic TriterpenesHT29 CellsMini reviews in medicinal chemistry
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In vivo anti-inflammatory activity of saponins from Bupleurum rotundifolium

2001

Seven oleanane-type triterpene saponins were isolated from the methanolic extract of the aerial parts of Bupleurum rotundifolium. They were identified on the basis of their spectral data as 3-O-[alpha-L-rhamnopyranosyl (1--2)-beta-D-glucopyranosyl (1--2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl (1--2)-beta-D-glucopyranosyl] echinocystic acid (saponin 1), 3-O-[alpha-L-rhamnopyranosyl (1--2)-beta-D-glucopyranosyl (1--2)-beta-D-fucopyranosyl] 11-methoxy-primulagenin A (saponin 2), rotundioside E (saponin 3), rotundioside F (saponin 4), 3beta-sulfate, 28-O-[beta-D-glucopyranosyl (1--6)-beta-D-glucopyranosyl (1--2)-beta-D-glucopyranosyl (1--2)-beta-D-glucopyranosyl] ester of primulagen…

chemistry.chemical_classificationPlants MedicinalTraditional medicineChemistrymedicine.drug_classAnti-Inflammatory AgentsSaponinGeneral MedicineSaponinsGeneral Biochemistry Genetics and Molecular BiologyAnti-inflammatoryMiceTriterpeneIn vivoBupleurum rotundifoliummedicineAnimalsTetradecanoylphorbol AcetateFemaleGeneral Pharmacology Toxicology and PharmaceuticsEchinocystic acidSpectral dataEar edemaLife Sciences
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Foetidissimosides C–F, Novel Glycosides from the Roots ofCucurbita foetidissima

2004

Two novel echinocystic acid (=(3β,16α)-3,16-dihydroxyolean-12-en-28-oic acid) glycosides, foetidissimosides C (1), and D (2), along with new cucurbitane glycosides, i.e., foetidissimosides E/F (3/4) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB-MS. The new compounds were characterized as (3β,16α)-28-{[O-β-D-glucopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-6-deoxy-α-L-mannopyranosyl-(12)-α-L-arabinopyranosyl]oxy}-16-hydroxy-28-oxoolean -12-en-3-yl β-D-glucopyranosiduronic acid (1…

chemistry.chemical_classificationbiologyChemistryStereochemistryOrganic ChemistryGlycosideCucurbitanebiology.organism_classificationBiochemistryCatalysisInorganic Chemistrychemistry.chemical_compoundHeteronuclear moleculeDrug DiscoveryEpimerCucurbita foetidissimaPhysical and Theoretical ChemistryEchinocystic acidTwo-dimensional nuclear magnetic resonance spectroscopyHeteronuclear single quantum coherence spectroscopyHelvetica Chimica Acta
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Foetidissimosides C—F, Novel Glycosides from the Roots of Cucurbita foetidissima.

2004

Two novel echinocystic acid (=(3β,16α)-3,16-dihydroxyolean-12-en-28-oic acid) glycosides, foetidissimosides C (1), and D (2), along with new cucurbitane glycosides, i.e., foetidissimosides E/F (3/4) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB-MS. The new compounds were characterized as (3β,16α)-28-{[O-β-D-glucopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-6-deoxy-α-L-mannopyranosyl-(12)-α-L-arabinopyranosyl]oxy}-16-hydroxy-28-oxoolean -12-en-3-yl β-D-glucopyranosiduronic acid (1…

chemistry.chemical_classificationbiologyStereochemistryGlycosideGeneral Medicinebiology.organism_classificationCucurbitanechemistry.chemical_compoundchemistryHeteronuclear moleculeCucurbita foetidissimaEpimerEchinocystic acidTwo-dimensional nuclear magnetic resonance spectroscopyHeteronuclear single quantum coherence spectroscopyChemInform
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