title: A cytotoxic meroterpenoid benzoquinone from roots of Cordia globosa.
abstract: (1a S*,1b S*,7a S*,8a S*)-4,5-Dimethoxy-1a,7a-dimethyl-1,1a,1b,2,7, 7a,8,8a-octahydrocyclopropa cyclopenta[1,2-b]naphthalene-3,6-dione (1), a new meroterpenoid benzoquinone, and microphyllaquinone (2), a known naphthoquinone, have been isolated from roots of Cordia globosa. Both structure determinations were performed by conventional spectroscopic methods, including inverse detection NMR techniques, and by comparison with data from the literature for related compounds. Compound 1 displayed considerable cytotoxic activity against several cancer cell lines with IC50 values in the range of 1.2 to 5.0 microg/mL. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2'-deoxyuridine incorporation, and apoptosis induction, as indicated by the acridine orange/ethidium bromide assay and morphological changes after 24 h of incubation on leukemic cells.
authors.affiliation: Curso de Pós-Graduação em Química Orgânica, Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, Fortaleza, Ceará, Brazil.
authors.forename: Jane Eire
authors.initials: JE
authors.lastname: Alencar de Menezes
authors.forename: Telma Leda
authors.initials: TL
authors.lastname: Lemos
authors.forename: Otília Deusdênia
authors.initials: OD
authors.lastname: Pessoa
authors.forename: Raimundo
authors.initials: R
authors.lastname: Braz-Filho
authors.forename: Raquel C
authors.initials: RC
authors.lastname: Montenegro
authors.forename: Diego Veras
authors.initials: DV
authors.lastname: Wilke
authors.forename: Letícia V
authors.initials: LV
authors.lastname: Costa-Lotufo
authors.forename: Cláudia
authors.initials: C
authors.lastname: Pessoa
authors.forename: Manoel Odorico
authors.initials: MO
authors.lastname: de Moraes
authors.forename: Edilberto R
authors.initials: ER
authors.lastname: Silveira
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D016227:Benzoquinones / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D045744:Cell Line, Tumor / Q000187:drug effects; D031213:Cordia; D004273:DNA, Neoplasm / Q000187:drug effects; D004317:Doxorubicin / Q000494:pharmacology; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D018517:Plant Roots
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D016227:Benzoquinones; D004273:DNA, Neoplasm; D010936:Plant Extracts; D004317:Doxorubicin