Search results for "Acanthophyllum"

showing 6 items of 6 documents

Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum

2010

From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-β-D-galactopyranosylgypsogenic acid-28-O-β-D-glucopyranosyl-(13)-[β-D-glucopyranosyl-(16)]-β-D-galactopyranoside (1) and gypsogenic acid-28-O-β-D-glucopyranosyl-(13)-[β-D-glucopyranosyl-(16)]-β-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116). Copyr…

chemistry.chemical_classificationfood.ingredientbiologyStereochemistryGlycosideCaryophyllaceaeGeneral Chemistrybiology.organism_classificationAcanthophyllumHuman colon cancerchemistry.chemical_compoundfoodchemistryGeneral Materials ScienceCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyOleananeMagnetic Resonance in Chemistry
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ChemInform Abstract: Two New Triterpene Saponins from Acanthophyllum laxiusculum

2015

Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-β-D-galactopyranosylgypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (1) and gypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (2).

chemistry.chemical_classificationAcanthophyllum laxiusculumTerpenechemistryTriterpeneStereochemistryGlycosideGeneral MedicineChemInform
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Two New Triterpene Saponins fromAcanthophyllum laxiusculum

2015

Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-β-D-galactopyranosylgypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (1) and gypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (2).

Inorganic Chemistrychemistry.chemical_classificationTerpeneAcanthophyllum laxiusculumTriterpenechemistryStereochemistryOrganic ChemistryDrug DiscoveryGlycosidePhysical and Theoretical ChemistryBiochemistryCatalysisHelvetica Chimica Acta
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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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New Triterpene Saponins fromAcanthophyllum pachystegium

2004

Four new triterpenoid saponins, pachystegiosides A (1), B (2), C (3), and D (4), were isolated from the roots of Acanthophyllum pachystegium K. H. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FAB-MS. The new compounds were characterized as 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-β-D-xylopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[3,4-di-O-acetyl-β-D-quinovopyranosyl-(14)]-β-D-fucopyranosyl}ester (1), 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-…

chemistry.chemical_classificationStereochemistryOrganic ChemistryBiochemistryCatalysisInorganic ChemistryQuillaic acidTriterpenoidTriterpenechemistryHeteronuclear moleculeAcanthophyllum pachystegiumDrug DiscoveryPhysical and Theoretical ChemistryTwo-dimensional nuclear magnetic resonance spectroscopyHeteronuclear single quantum coherence spectroscopyHelvetica Chimica Acta
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Squarroside A, a biologically active triterpene saponin from Acanthophyllum squarrosum.

1993

A new bioactive saponin has been isolated from the roots of Acanthophyllum squarrosum. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis, and on chemical transformations, the structure of this new compound was elucidated as 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)-[alpha-L-arabinofuranosyl-(1--3)]-beta-D-4-O- acetylfucopyranoside for which we proposed the name squarroside A. This molecule showed a concentration dependent immunomodulatory effect in the in vitro lymphocyte transformation test.

Magnetic Resonance SpectroscopyStereochemistryMolecular Sequence DataSaponinPlant ScienceHorticultureBiologyBiochemistryAcanthophyllum squarrosumTriterpeneCarbohydrate ConformationMoleculeHumansLymphocytesOleanolic AcidMolecular Biologychemistry.chemical_classificationBiological activityGeneral MedicinePlantsSaponinsIn vitroTriterpeneschemistryHeteronuclear moleculeCarbohydrate SequenceTwo-dimensional nuclear magnetic resonance spectroscopyPhytochemistry
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