title: Guaianolides and a seco-Eudesmane from the Resinous Exudates of Cushion Bush (Leucophyta brownii) and Evaluation of Their Cytostatic and Anti-inflammatory Activity.
abstract: A detailed phytochemical investigation of a dichloromethane extract of the resinous exudates of the cushion bush plant (Leucophyta brownii) resulted in the isolation of the new 8,12-guaianolides leucophytalins A (5) and B (6), the new 1,10-seco-eudesmane leucophytalin C (10), six rare 8,12-guaianolides (1-4, 7, and 8), and the xanthanolide tomentosin (9). The structures of all isolated compounds were elucidated on the basis of spectroscopic and spectrometric analyses. The structures of compounds isolated in crystalline form, including leucophytalins A and C, were further confirmed by X-ray crystallography. The crude extract exhibited moderate cytostatic activity against a breast cancer (MCF-7) and human colon cancer (HT-29) cell line with IC₅₀ values of 9.3 and 18 μg/mL, respectively, and anti-inflammatory activity against the macrophage-like cell line RAW 264.7 with IC₅₀ values of 3.9 and 6.1 μg/mL for thromboxane B2 and prostaglandin E2 production, respectively. The isolated compounds were evaluated for their cytostatic activity against MCF-7 and HT-29 cells (1, 3-10) and their anti-inflammatory activity against RAW 264.7 cells (1-10). All isolated compounds are most likely derived from (+)-germacrene A, and a biosynthetic pathway is proposed for these sesquiterpenoids.
authors.affiliation: Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark.
authors.forename: Mette G
authors.initials: MG
authors.lastname: Hyldgaard
authors.affiliation: Department of Animal Science, Aarhus University , Blichers Allé 20, 8830 Tjele, Denmark.
authors.forename: Stig
authors.initials: S
authors.lastname: Purup
authors.affiliation: Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Bond
authors.affiliation: Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark.
authors.forename: Xavier C
authors.initials: XC
authors.lastname: Fretté
authors.affiliation: Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark.
authors.forename: Haiyan
authors.initials: H
authors.lastname: Qu
authors.affiliation: Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark.
authors.forename: Katrine T
authors.initials: KT
authors.lastname: Jensen
authors.affiliation: Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark.
authors.forename: Lars P
authors.initials: LP
authors.lastname: Christensen
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D018360:Crystallography, X-Ray; D054697:Cytostatic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D007783:Lactones / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D012116:Resins, Plant / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry; D045787:Sesquiterpenes, Eudesmane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D054697:Cytostatic Agents; D007783:Lactones; D012116:Resins, Plant; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; D045789:Sesquiterpenes, Guaiane; C454646:tomentosin; C015872:eudesmane