title: Endogenous enzyme-hydrolyzed fruit of Cirsium brachycephalum: optimal source of the antiproliferative lignan trachelogenin regulating the Wnt/β-catenin signaling pathway in the SW480 colon adenocarcinoma cell line.
abstract: The molecular constituents of Cirsium brachycephalum fruits were identified, quantified and isolated for the first time. The lignan glycoside tracheloside was the main compound, which was transformed quantitatively into its aglycone trachelogenin by endogenous enzymatic treatment of the fruit. Following this transformation by high performance liquid chromatography (HPLC) hyphenated with UV and mass spectrometry (MS) detections on a quantitative basis, the enzyme-hydrolyzed fruit was found to be the richest raw material containing trachelogenin (17.2mg/g) reported to date. Thus, the enzyme-hydrolyzed fruit was used to isolate trachelogenin using preparative HPLC in order to (1) unambiguously confirm its identity by gas chromatography-MS, nuclear magnetic resonance spectroscopy and optical rotation, and (2) investigate its in vitro antiproliferative activities against the SW480 colon adenocarcinoma cell line. Trachelogenin significantly affected the phosphorylation of key proteins such as β-Catenin, c-Myc and GSK3 in the β-Catenin signaling pathway in a concentration-dependent manner. These changes account for the antiproliferative effects of trachelogenin.
authors.affiliation: 1st Department of Pathology and Experimental Cancer Research, Semmelweis University, Üllői út 26, Budapest 1085, Hungary.
authors.forename: Zsolt
authors.initials: Z
authors.lastname: Mervai
authors.affiliation: Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, Budapest 1117, Hungary.
authors.forename: Anna
authors.initials: A
authors.lastname: Sólyomváry
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre utca 7, Budapest 1092, Hungary.
authors.forename: Gergő
authors.initials: G
authors.lastname: Tóth
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre utca 7, Budapest 1092, Hungary.
authors.forename: Béla
authors.initials: B
authors.lastname: Noszál
authors.affiliation: Department of Analytical Chemistry, Institute of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, Budapest 1117, Hungary.
authors.forename: Ibolya
authors.initials: I
authors.lastname: Molnár-Perl
authors.affiliation: 1st Department of Pathology and Experimental Cancer Research, Semmelweis University, Üllői út 26, Budapest 1085, Hungary.
authors.forename: Kornélia
authors.initials: K
authors.lastname: Baghy
authors.affiliation: 1st Department of Pathology and Experimental Cancer Research, Semmelweis University, Üllői út 26, Budapest 1085, Hungary.
authors.forename: Ilona
authors.initials: I
authors.lastname: Kovalszky
authors.affiliation: Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, Budapest 1117, Hungary. Electronic address: boldizsarimi@gmail.com.
authors.forename: Imre
authors.initials: I
authors.lastname: Boldizsár
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000494:pharmacology; D000230:Adenocarcinoma / Q000473:pathology; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D045744:Cell Line, Tumor; D031180:Cirsium / Q000737:chemistry*; D003110:Colonic Neoplasms / Q000473:pathology; D005638:Fruit / Q000737:chemistry; D038362:Glycogen Synthase Kinase 3 / Q000378:metabolism; D006801:Humans; D017705:Lignans / Q000494:pharmacology; D015394:Molecular Structure; D016271:Proto-Oncogene Proteins c-myc / Q000378:metabolism; D060449:Wnt Signaling Pathway / Q000187:drug effects*; D051176:beta Catenin / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C495270:CTNNB1 protein, human; D017705:Lignans; C489427:MYC protein, human; D016271:Proto-Oncogene Proteins c-myc; D051176:beta Catenin; C560586:trachelogenin; D038362:Glycogen Synthase Kinase 3; D015107:4-Butyrolactone
keywords: Antiproliferative; Cirsium; Lignan; Trachelogenin; β-Catenin