Structure of tyrolobibenzyl D and biological activity of tyrolobibenzyls from Scorzonera humilis.
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.
Zidorn
Christian
C
Institut für Pharmazie, Abteilung Pharmakognosie, Universität Innsbruck, Austria. Christian.H.Zidorn@uibk.ac.at
Spitaler
Renate
R
Ellmerer-Müller
Ernst-P
EP
Perry
Nigel B
NB
Gerhäuser
Clarissa
C
Stuppner
Hermann
H
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
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)