title: Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus.
abstract: A novel type of polyprenols, alloprenols, with an alpha-trans-isoprenoid unit was found in the leaves of Allophylus caudatus (Sapindaceae) besides typical alpha-cis-polyprenols. The polyprenol family (Prenol-11-13, Prenol-12 dominating) was accompanied by traces of dolichols of the same chain-length. Prenol alpha-cis- and alpha-trans-isomers were chromatographically separated and their structure was analyzed by HPLC/ESI-MS, HR-ESI-MS and 1H and 13C NMR spectroscopy. Model compounds, semi-synthetic alpha-isomers of all-trans-Pren-9 and mainly-cis-Pren-11, were obtained using an oxidation-reduction procedure. Comparison of their NMR spectra confirmed the structure of the newly identified polyprenols. The observed pattern of NMR signal shifts may be applied for elucidation of isoprenoid structure.
authors.affiliation: Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawinskiego 5a, 02-106 Warsaw, Poland. eciepichal@ibb.waw.pl
authors.forename: Ewa
authors.initials: E
authors.lastname: Ciepichal
authors.forename: Jacek
authors.initials: J
authors.lastname: Wojcik
authors.forename: Tomasz
authors.initials: T
authors.lastname: Bienkowski
authors.forename: Magdalena
authors.initials: M
authors.lastname: Kania
authors.forename: Malgorzata
authors.initials: M
authors.lastname: Swist
authors.forename: Witold
authors.initials: W
authors.lastname: Danikiewicz
authors.forename: Andrzej
authors.initials: A
authors.lastname: Marczewski
authors.forename: Jozefina
authors.initials: J
authors.lastname: Hertel
authors.forename: Zdzislaw
authors.initials: Z
authors.lastname: Matysiak
authors.forename: Ewa
authors.initials: E
authors.lastname: Swiezewska
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Chojnacki
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D045782:Hemiterpenes; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000439:Pentanols / Q000737:chemistry*; D029631:Sapindaceae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D045782:Hemiterpenes; D000439:Pentanols; C009034:prenol