title: In vitro anti-proliferation/cytotoxic activity of epingaione and its derivatives on the human SH-SY5Y neuroblastoma and TE-671 sarcoma cells.
abstract: Epingaione (4-Methyl-1-(5-methyl-2, 3,4,5-tetrahydro-[2,3']bifuranyl-5-yl)-pentan-2-one) was isolated as one of the major lipophilic secondary metabolites from the leaves and stems of Bontia daphnoides L. The compound gave 79.24% and 50.83% anti-proliferation/cytotoxic activity on the human SH-SY5Y neuroblastoma and TE-671 sarcoma cells in vitro at 50 pg/mL, respectively. Epingaione was transformed into eleven derivatives under laboratory conditions using ethanol, some gave greater anti-proliferation/cytotoxic activity on the cancer cell lines tested. One of the derivatives (compound 2) with enhanced cytotoxic activity was elucidated as 5'-Ethoxy-5-methyl-5-(4-methyl-2-oxo-pentyl)-2,3,4,5-tetrahydro-5'H-[2,3']bifuranyl-2'-one. Both epingaione and compound 2 caused an accumulation of arrested or dead SH-SY5Y neuroblastoma in the m-phase of the cell cycle as revealed by the m-phase specific marker KE 67.
authors.affiliation: The University of Hohenheim, Institutes for Bio-organic Chemistry , Garbenstr 30, D-70593 Stuttgart, Germany. lawrencew@src-jamaica.org
authors.forename: L A D
authors.initials: LA
authors.lastname: Williams
authors.forename: J
authors.initials: J
authors.lastname: Conrad
authors.forename: B
authors.initials: B
authors.lastname: Vogler
authors.forename: H
authors.initials: H
authors.lastname: Rösner
authors.forename: R B R
authors.initials: RB
authors.lastname: Porter
authors.forename: W
authors.initials: W
authors.lastname: Setzer
authors.forename: E N
authors.initials: EN
authors.lastname: Barton
authors.forename: H G
authors.initials: HG
authors.lastname: Levy
authors.forename: S
authors.initials: S
authors.lastname: Mika
authors.forename: I
authors.initials: I
authors.lastname: Klaiber
authors.forename: J P
authors.initials: JP
authors.lastname: Nkurunziza
authors.forename: W
authors.initials: W
authors.lastname: Kraus
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D031642:Myoporaceae; D009447:Neuroblastoma / Q000188:drug therapy*; D010422:Pentanones / Q000737:chemistry / Q000494:pharmacology*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018515:Plant Leaves; D018547:Plant Stems; D012509:Sarcoma / Q000188:drug therapy*
chemical_list: C522126:4-methyl-1-(5-methyl-2, 3,4,5-tetrahydro-(2,3')bifuranyl-5-yl)-pentan-2-one; D005663:Furans; D010422:Pentanones; D010936:Plant Extracts