title: Secondary metabolites from two species of Pulicaria and their cytotoxic activity.
abstract: Two new compounds, the sesquiterpene (1E,5E)-8β-acetoxy-4α-hydroxy-7βH-germacra-1(10),5-dien-14-oic acid (2), and a nor-sesquiterpene, (5E)-8β-acetoxy-4α-hydroxy-7βH-germacr-5-en-10-one (3), were isolated from Pulicaria canariensis ssp. lanata, along with ten known compounds, including the flavonoid 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (4). From Pulicaria burchardii, we isolated seven known compounds; the physical and spectroscopic data of the triterpenoid 3β-hydroxytaraxaster-20-en-30-al (1) are reported. The structures of compounds 1-3 were determined on the basis of HR-MS, and 1D- and 2D-NMR studies. The structure of 2 was corroborated by X-ray crystal diffraction. Cell viability experiments revealed that the semisynthetic flavonoid 4b was the most cytotoxic compound against human leukemia cells, and the cytotoxicity was caused by induction of apoptosis, as determined by microscopy of nuclear changes.
authors.affiliation: Departamento de Química, Universidad de Las Palmas de Gran Canaria, Unidad Asociada al CSIC, Campus de Tafira, SP, Las Palmas de Gran Canaria.
authors.forename: Jorge
authors.initials: J
authors.lastname: Triana
authors.forename: Mariana
authors.initials: M
authors.lastname: López
authors.forename: Francisco Javier
authors.initials: FJ
authors.lastname: Pérez
authors.forename: Francisco
authors.initials: F
authors.lastname: León
authors.forename: José
authors.initials: J
authors.lastname: Quintana
authors.forename: Francisco
authors.initials: F
authors.lastname: Estévez
authors.forename: Juan C
authors.initials: JC
authors.lastname: Hernández
authors.forename: Javier
authors.initials: J
authors.lastname: González-Platas
authors.forename: Ignacio
authors.initials: I
authors.lastname: Brouard
authors.forename: Jaime
authors.initials: J
authors.lastname: Bermejo
mesh_terms: D000970:Antineoplastic Agents / Q000302:isolation & purification / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002855:Chromatography, Thin Layer; D018360:Crystallography, X-Ray; D005419:Flavonoids / Q000302:isolation & purification / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000166:cytology / Q000254:growth & development / Q000378:metabolism; D052587:Pulicaria / Q000737:chemistry* / Q000254:growth & development / Q000378:metabolism*; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D005419:Flavonoids; D012717:Sesquiterpenes; D014315:Triterpenes