title: Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol.
abstract: The biotransformation of xanthohumol (1), a prenylated chalcone isolated from hops by selected fungi, was investigated. Microbial regioselective glycosylation at the C-4' position led to xanthohumol 4'-O-β-d-glucopyranoside (2) and xanthohumol 4'-O-β-d-(4'''-O-methyl)-glucopyranoside (3). The subsequent cyclization of 2 resulted in isoxanthohumol 7-O-β-glucopyranoside (4). The structures of the products were identified based on spectroscopic methods. The biological activity of isolated metabolites has been evaluated. Compared to xanthohumol (1), metabolite 2 is a better 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenger, while 2 and 3 have stronger antiproliferative activity against the human HT-29 colon cancer cell line.
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. tomasz.tronina@up.wroc.pl
authors: Tomasz
authors: T
authors: Tronina
authors: Agnieszka
authors: A
authors: Bartmańska
authors: Magdalena
authors: M
authors: Milczarek
authors: Joanna
authors: J
authors: Wietrzyk
authors: Jarosław
authors: J
authors: Popłoński
authors: Edward
authors: E
authors: Rój
authors: Ewa
authors: E
authors: Huszcza
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001711:Biotransformation; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006031:Glycosylation; D019073:HT29 Cells; D006801:Humans; D015394:Molecular Structure; D011427:Propiophenones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D005419:Flavonoids; D006027:Glycosides; D011427:Propiophenones; C104536:xanthohumol