Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus.
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.
Ciepichal
Ewa
E
Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawinskiego 5a, 02-106 Warsaw, Poland. eciepichal@ibb.waw.pl
Wojcik
Jacek
J
Bienkowski
Tomasz
T
Kania
Magdalena
M
Swist
Malgorzata
M
Danikiewicz
Witold
W
Marczewski
Andrzej
A
Hertel
Jozefina
J
Matysiak
Zdzislaw
Z
Swiezewska
Ewa
E
Chojnacki
Tadeusz
T
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
D045782:Hemiterpenes; D000439:Pentanols; C009034:prenol