Chemistry and Physics of Lipids 2007-06-01

Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus.

Ewa Ciepichal, Jacek Wojcik, Tomasz Bienkowski, Magdalena Kania, Malgorzata Swist, Witold Danikiewicz, Andrzej Marczewski, Jozefina Hertel, Zdzislaw Matysiak, Ewa Swiezewska, Tadeusz Chojnacki

Index: Chem. Phys. Lipids 147(2) , 103-12, (2007)

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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.