6533b7d6fe1ef96bd12671e8
RESEARCH PRODUCT
Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species
Abiy YenesewVincent Kam Wai WongMáté ErdélyiMáté ErdélyiPaolo CoghiSolomon DereseJiaying GaoArto ValkonenEric M. GuantaiSouaibou Yaoubasubject
Lung Neoplasms<i>Aspilia mossambicensis</i>Pharmaceutical ScienceCrystal structureAspilia plurisetaAsteraceaePlant Roots01 natural sciencesAnalytical Chemistryent-kaurane diterpenoid.Drug DiscoveryAspilia mossambicensisCytotoxicityEnt kauraneta116Organisk kemiMolecular StructurebiologyChemistryLiver NeoplasmsHep G2 CellsMass spectrometricterpeenitPhytochemicalChemistry (miscellaneous)solunsalpaajatMolecular MedicinecytotoxicityasterikasvitDiterpenes KauraneAspilia<i>ent</i>-kaurane diterpenoidCarcinoma HepatocellularCell SurvivalStereochemistry010402 general chemistryta3111Articlelcsh:QD241-441lcsh:Organic chemistryHumans<i>Aspilia pluriseta</i>Physical and Theoretical ChemistryIC50x-ray crystallography010405 organic chemistrycytostatic drugsOrganic Chemistryta1182Adenocarcinoma Bronchiolo-AlveolarPlant Components AerialAsteraceaebiology.organism_classificationluonnonaineetX-ray crystal structurenaturally occurring substances0104 chemical sciencesA549 Cellsent-kaurane diterpenoidröntgenkristallografiaterpenesdescription
A phytochemical investigation of the roots of Aspilia pluriseta led to the isolation of ent-kaurane-type diterpenoids and additional phytochemicals (1⁻23). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analyses. The absolute configurations of seven of the ent-kaurane-type diterpenoids (3⁻6, 6b, 7 and 8) were determined by single crystal X-ray diffraction studies. Eleven of the compounds were also isolated from the roots and the aerial parts of Aspilia mossambicensis. The literature NMR assignments for compounds 1 and 5 were revised. In a cytotoxicity assay, 12α-methoxy-ent-kaur-9(11),16-dien-19-oic acid (1) (IC50 = 27.3 ± 1.9 µM) and 9β-hydroxy-15α-angeloyloxy-ent-kaur-16-en-19-oic acid (3) (IC50 = 24.7 ± 2.8 µM) were the most cytotoxic against the hepatocellular carcinoma (Hep-G2) cell line, while 15α-angeloyloxy-16β,17-epoxy-ent-kauran-19-oic acid (5) (IC50 = 30.7 ± 1.7 µM) was the most cytotoxic against adenocarcinomic human alveolar basal epithelial (A549) cells.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-12-01 | Molecules |