title: Structure of tyrolobibenzyl D and biological activity of tyrolobibenzyls from Scorzonera humilis.
abstract: A novel tyrolobibenzyl derivative, 1-->beta-D-apiosyl-beta-D-glucopyranosyl 4-[2-(4-hydroxyphenyl)ethyl]benzofuran-2-carboxylate 3 (tyrolobibenzyl D) was isolated from Scorzonera humilis L. and its structure established by mass spectrometry and 1D- and 2D-NMR spectroscopy. The biological activities of the new compound and related tyrolobibenzyls A-C (1-2, 4) and the semi-synthetic peracetyl derivatives of tyrolobibenzyls B (2a) and C (4a) were assessed. The results revealed no cytotoxic activity against P388 cells and neither anti-bacterial activity against Bacillus subtilis nor antifungal activity against Candida albicans and Trichophyton mentagrophytes for any of the investigated compounds. An evaluation of potential chemopreventive activity of 2, 2a, 4, and 4a also revealed no pronounced activity in any of the employed assaying systems.
authors.affiliation: Institut für Pharmazie, Abteilung Pharmakognosie, Universität Innsbruck, Austria. Christian.H.Zidorn@uibk.ac.at
authors.forename: Christian
authors.initials: C
authors.lastname: Zidorn
authors.forename: Renate
authors.initials: R
authors.lastname: Spitaler
authors.forename: Ernst-P
authors.initials: EP
authors.lastname: Ellmerer-Müller
authors.forename: Nigel B
authors.initials: NB
authors.lastname: Perry
authors.forename: Clarissa
authors.initials: C
authors.lastname: Gerhäuser
authors.forename: Hermann
authors.initials: H
authors.lastname: Stuppner
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001593:Benzyl Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects*; D019363:Cytochrome P-450 CYP1A1 / Q000037:antagonists & inhibitors; D004187:Disaccharides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007941:Leukemia P388; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000037:antagonists & inhibitors; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D001572:Benzofurans; D001593:Benzyl Compounds; D004187:Disaccharides; D004791:Enzyme Inhibitors; C466769:tryolobibenzyl D; D019363:Cytochrome P-450 CYP1A1; D016660:NAD(P)H Dehydrogenase (Quinone)