title: Isolation, characterization, and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae.
abstract: Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9α-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.
authors: Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors: Snežana
authors: S
authors: Trifunović
authors: Institute of Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Belgrade, Serbia.
authors: Anđelka M
authors: AM
authors: Isaković
authors: Institute of Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Belgrade, Serbia.
authors: Aleksandra
authors: A
authors: Isaković
authors: Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors: Ivan
authors: I
authors: Vučković
authors: Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors: Boris
authors: B
authors: Mandić
authors: Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors: Miroslav
authors: M
authors: Novaković
authors: Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors: Vlatka
authors: V
authors: Vajs
authors: Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors: Slobodan
authors: S
authors: Milosavljević
authors: Institute of Microbiology and Immunology, School of Medicine, University of Belgrade, Belgrade, Serbia.
authors: Vladimir
authors: V
authors: Trajković
mesh_terms: D031162:Achillea / Q000737:chemistry*; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D017209:Apoptosis; D045744:Cell Line, Tumor; D005910:Glioma / Q000188:drug therapy*; D006801:Humans; D006830:Hydralazine / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000737:chemistry / Q000302:isolation & purification; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D011422:Propionates / Q000737:chemistry / Q000302:isolation & purification; D051381:Rats; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*
chemical_list: C000592851:9-acetoxy-3-O-methyl-iso-seco-tanapartholide; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D011422:Propionates; D045789:Sesquiterpenes, Guaiane; C499736:sintenin; D006830:Hydralazine; D009828:Oleanolic Acid