title: Cytotoxic prenylated flavanones from Monotes engleri.
abstract: From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. There of these substances are novel, namely, 6-(1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O-methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6-[(2RS)-hydroxy-3-methyl-3-butenyl]-8-prenyleriodictyol and 5,4'-dihydroxy-4",4"-dimethyl-5"-methyl-5"H-dihydrofurano[2",3": 6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
authors.forename: E K
authors.initials: EK
authors.lastname: Seo
authors.forename: G L
authors.initials: GL
authors.lastname: Silva
authors.forename: H B
authors.initials: HB
authors.lastname: Chai
authors.forename: T E
authors.initials: TE
authors.lastname: Chagwedera
authors.forename: N R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: G A
authors.initials: GA
authors.lastname: Cordell
authors.forename: J M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: A D
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000633:toxicity*; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000302:isolation & purification* / Q000633:toxicity*; D005910:Glioma / Q000188:drug therapy; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000302:isolation & purification* / Q000633:toxicity*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005419:Flavonoids; D010936:Plant Extracts