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Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus |
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| Authors: | Ciepichal Ewa Wojcik Jacek Bienkowski Tomasz Kania Magdalena Swist Malgorzata Danikiewicz Witold Marczewski Andrzej Hertel Jozefina Matysiak Zdzislaw Swiezewska Ewa Chojnacki Tadeusz |
| Institution: | a Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawinskiego 5a, 02-106 Warsaw, Poland b Laboratory of Biological NMR, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawinskiego 5a, 02-106 Warsaw, Poland c Laboratory of Mass Spectrometry, Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland d Botanical Garden-CBDC, Polish Academy of Sciences, Prawdziwka 2, 02-976 Warsaw, Poland |
| Abstract: | A novel type of polyprenols, alloprenols, with an α-trans-isoprenoid unit was found in the leaves of Allophylus caudatus (Sapindaceae) besides typical α-cis-polyprenols. The polyprenol family (Prenol-11-13, Prenol-12 dominating) was accompanied by traces of dolichols of the same chain-length. Prenol α-cis- and α-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 α-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. |
| Keywords: | Polyprenol Trans-isomer Chemical isomerization Nuclear magnetic resonance spectroscopy Electrospray mass spectrometry |
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