title: Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.
abstract: Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E (4), and a new benzanthrone natural product, 6,8-dihydroxy-10-methyl-7H-benz[de]anthracen-7-one (5), together with 10 known compounds, 6,8-dihydroxy-4-methyl-7H-benz[de]anthracen-7-one (6), nataloe-emodin (7), chrysophanein, chrysophanol, 1,5-dihydroxy-7-methoxy-3-methylanthraquinone, pulmatin, 7-hydroxycoumarin, 7-hydroxy-6-methoxycoumarin, beta-sitosterol, and beta-sitosterol glucoside. The structures of 1-5 were established by spectroscopic methods, including 1D and 2D NMR, HRMS, and CD data interpretation. The cytotoxic activity of all isolates was evaluated in a small panel of human cancer cell lines. Compound 7 exhibited significant in vitro cytotoxic activity in the tested cell lines, but no significant activity was observed with an in vivo hollow fiber model at doses of 6.25, 12.5, 25, and 50 mg/kg/injection.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
authors.forename: Fredyc
authors.initials: F
authors.lastname: Diaz
authors.forename: Hee-Byung
authors.initials: HB
authors.lastname: Chai
authors.forename: Qiuwen
authors.initials: Q
authors.lastname: Mi
authors.forename: Bao-Ning
authors.initials: BN
authors.lastname: Su
authors.forename: Jose Schunke
authors.initials: JS
authors.lastname: Vigo
authors.forename: James G
authors.initials: JG
authors.lastname: Graham
authors.forename: Fernando
authors.initials: F
authors.lastname: Cabieses
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: Geoffrey A
authors.initials: GA
authors.lastname: Cordell
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000873:Anthracenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured; D000095322:Anthrones
chemical_list: D000873:Anthracenes; D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; C483984:mayoside D; C483985:mayoside E; C483982:picramnioside G; C483983:picramnioside H; C004522:anthrone; D000095322:Anthrones