title: Further constituents of Galianthe thalictroides (Rubiaceae) and inhibition of DNA topoisomerases I and IIα by its cytotoxic β-carboline alkaloids.
abstract: A new cytotoxic β-carboline alkaloid, 1-methyl-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol (1), was isolated from roots of Galianthe thalictroides, together with the alkaloid 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol (2), the anthraquinones 1-methyl-alizarin and morindaparvin-A, the coumarin scopoletin, homovanillic alcohol, (-)-epicatechin, and the steroids stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, 6-β-hydroxy-stigmast-4-en-3-one, stigmasterol, campesterol, β-sitosterol, and β-sitosterol-3-O-β-D-glucopyranoside. Among the previously known compounds, homovanillic alcohol is a novel finding in Rubiaceae, while 1-methyl-alizarin, morindaparvin-A, scopoletin, stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, and 6-β-hydroxy-stigmast-4-en-3-one is reported for the first time in the genus Galianthe. The cytotoxic β-carboline alkaloids 1 and 2 exhibited potent antitopoisomerase I and IIα activities and strong evidence is provided for their action as topoisomerase IIα poisons and redox-independent inhibitors.
authors: Instituto de Química, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS 79074-460, Brazil. Electronic address: paty_ms@yahoo.com.br.
authors: Patrícia
authors: P
authors: de Oliveira Figueiredo
authors: Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS 79070-900, Brazil. Electronic address: renataperdomo@gmail.com.
authors: Renata Trentin
authors: RT
authors: Perdomo
authors: Instituto de Química, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS 79074-460, Brazil. Electronic address: fernandargarcez@gmail.com.
authors: Fernanda Rodrigues
authors: FR
authors: Garcez
authors: Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS 79070-900, Brazil. Electronic address: fatinha99@yahoo.com.br.
authors: Maria
authors: M
authors: de Fatima Cepa Matos
authors: Centro Pluridisciplinar de Pesquisas Químicas Biológicas e Agrícolas, Universidade Estadual de Campinas, Campinas, SP 13081-970, Brazil. Electronic address: carvalho@cpqba.unicamp.br.
authors: João Ernesto
authors: JE
authors: de Carvalho
authors: Instituto de Química, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS 79074-460, Brazil. Electronic address: walmir.garcez@ufms.br.
authors: Walmir Silva
authors: WS
authors: Garcez
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D000818:Animals; D000951:Antigens, Neoplasm / Q000378:metabolism*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004264:DNA Topoisomerases, Type I / Q000737:chemistry / Q000378:metabolism*; D004250:DNA Topoisomerases, Type II / Q000378:metabolism*; D004268:DNA-Binding Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism*; D006801:Humans; D007785:Lactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics; D061986:MCF-7 Cells; D051379:Mice; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D018517:Plant Roots / Q000737:chemistry / Q000378:metabolism; D019666:Rubiaceae / Q000737:chemistry* / Q000378:metabolism; D059003:Topoisomerase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity
chemical_list: D000470:Alkaloids; D000951:Antigens, Neoplasm; D004268:DNA-Binding Proteins; D009842:Oligopeptides; D059003:Topoisomerase Inhibitors; D004264:DNA Topoisomerases, Type I; D004250:DNA Topoisomerases, Type II; D007785:Lactose
keywords: Galianthe; Galianthe thalictroides; SRB assay; Topoisomerase; β-Carboline alkaloids